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Небесная энциклопедия

Космические корабли и станции, автоматические КА и методы их проектирования, бортовые комплексы управления, системы и средства жизнеобеспечения, особенности технологии производства ракетно-космических систем

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Мониторинг СМИ

Мониторинг СМИ и социальных сетей. Сканирование интернета, новостных сайтов, специализированных контентных площадок на базе мессенджеров. Гибкие настройки фильтров и первоначальных источников.

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Поддерживает ввод нескольких поисковых фраз (по одной на строку). При поиске обеспечивает поддержку морфологии русского и английского языка
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Применить Всего найдено 2312. Отображено 100.
27-12-2012 дата публикации

Bis-phosphate compound and asymmetric reaction using the same

Номер: US20120330038A1
Автор: Masahiro Terada, Norie Momiyama, Tohru Konno
Принадлежит: API Corp, Tohoku University NUC

A novel bis-phosphate compound is provided which can be applied to a wide range of reactive substrates and reactions as an asymmetric reaction catalyst and can realize an asymmetric reaction affording a high yield and a high enantiomeric excess. The bis-phosphate compound has a tetraaryl skeleton represented by General Formula (1). In an asymmetric reaction, an amidodiene and an unsaturated aldehyde compound are reacted with each other in the presence of the optically active bis-phosphate compound to give an optically active amidoaldehyde. The invention allows a reaction such as an asymmetric Diels-Alder reaction to proceed efficiently, which has been difficult with conventional mono-phosphate compounds. Thus, the invention enables an industrially feasible method for the production of optically active amidoaldehydes, optically active β-amino acid derivatives, optically active diamine compounds, optically active pyrrolidine derivatives and optically active dihydropyran derivatives which are useful as products such as medicines, agricultural chemicals and chemical products as well as synthesis intermediates for such products.

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Номер записи: 1
28-03-2013 дата публикации

METHOD FOR PRODUCING CARBAMATE, METHOD FOR PRODUCING ISOCYANATE, CARBAMATE PRODUCTION SYSTEM, AND ISOCYANATE PRODUCTION SYSTEM

Номер: US20130079546A1
Автор: Fukuda Takeshi, Kato Satoshi, NAKANO Tetsuya, SASAKI Masaaki, TAKAMATSU Koji
Принадлежит: MITSUI CHEMICALS, INC

A method for producing carbamate including a urea production step; a carbamate-forming step: an ammonia separation step of absorbing the gas with water in the presence of carbonate to produce a gas absorption water, and separating ammonia; an aqueous alcohol solution separation step of separating an aqueous alcohol solution from the gas absorption water; an ammonia/carbon dioxide separation step of separating carbon dioxide gas from the aqueous ammonia solution in the gas absorption water from which the aqueous alcohol solution is separated; an aqueous ammonia solution reusing step of mixing the aqueous ammonia solution and carbonate with the water to be used for production of the gas absorption water. 1. A method for producing carbamate , the method comprising the steps of:a urea production step of producing urea by reaction between ammonia and carbon dioxide gas,a carbamate-forming step of producing carbamate by carbamate-forming reaction between amine, the urea, and alcohol, and by-producing a gas containing alcohol, ammonia, and carbon dioxide,an ammonia separation step of absorbing the gas with water to produce a gas absorption water, and separating ammonia,an aqueous alcohol solution separation step of separating an aqueous alcohol solution from the gas absorption water,an ammonia/carbon dioxide separation step of separating carbon dioxide gas from the aqueous ammonia solution in the gas absorption water from which the aqueous alcohol solution is separated, andan aqueous ammonia solution reusing step of using the aqueous ammonia solution along with the water for production of the gas absorption water.2. The method for producing carbamate according to claim 1 , whereinin the ammonia separation step, the gas is absorbed with the water in the presence of carbonate,in the ammonia/carbon dioxide separation step, carbon dioxide gas is separated from the aqueous ammonia solution in the presence of the carbonate, andin the aqueous ammonia solution reusing step, along ...

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Номер записи: 2
18-04-2013 дата публикации

Process for Preparation of Optically Active Compounds using Transfer Hydrogenation

Номер: US20130096337A1
Автор: Foulkes Michael, Kesselgruber Martin, Mathes Christian
Принадлежит: NOVARTIS AG

A catalytic process for the preparation of optically active compounds and their conversion thereafter to desired drug substances. In particular, the process relates to the preparation of (S)-3-(1-Dimethylamino-ethyl)-phenol using asymmetric catalytic reduction and transfer hydrogenation, thereby providing an improved route to forming drug substances such as rivastigimine and rivastigimine hydrogen tartrate. 139-. (canceled)42. The process of claim 41 , wherein the asymmetric catalytic reduction forms an enantiomeric excess of compound (III) to compound (IV) of from about 96%:4% or higher claim 41 , about 98%:2% or higher claim 41 , or about 99%:1% or higher.43. The process of claim 41 , wherein after a crystallization step the enantiomeric excess of compound (III) to compound (IV) is from about 97%:3% or higher claim 41 , about 98%:2% or higher claim 41 , about 99%:1% or higher claim 41 , or about >99.5%:about <0.5% claim 41 , or about >99.7%:about <0.03.%.44. The process of claim 41 , wherein n=1 in general formulas (I)-(IV).45. The process of claim 41 , wherein n=1 in general formulas (I)-(IV) and a hydroxyl group occurs at position 3 on the aromatic ring.46. The process of claim 40 , wherein Ris a Calkyl claim 40 , Calkenyl claim 40 , Calkynyl claim 40 , or Corganohalide.47. The process of claim 40 , wherein Ris selected from any of methyl claim 40 , ethyl claim 40 , propyl and butyl.49. The process of claim 40 , wherein the transfer hydrogenation is performed using a chiral transition metal based catalyst.50. The process of claim 40 , wherein the transfer hydrogenation is performed using a complexed transition metal based chiral catalyst containing multiple aryl claim 40 , mono- bi- claim 40 , or poly-dentate ligands.51. The process of claim 40 , wherein the transfer hydrogenation is performed using a Ru claim 40 , Rh or Ir based catalyst.52. The process of claim 40 , wherein the transfer hydrogenation is performed using a chiral (diphenylethylenediamine) based ...

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Номер записи: 3
25-04-2013 дата публикации

TRANSITION METAL-CATALYZED PROCESSES FOR THE PREPARATION OF N-ALLYL COMPOUNDS AND USE THEREOF

Номер: US20130102780A1
Автор: GIGUERE Joshua Robert, MCCARTHY Keith Edward, REISCH Helge Alfred, SANDOVAL Sergio, STYMIEST Jake Larry
Принадлежит: Rhodes Technologies

The present disclosure provides processes for the N-dealkylation of tertiary amines and the use of transition metal catalysts to prepare tertiary N-allyl amine derivatives and secondary amine derivatives thereof. The tertiary amines can be alkaloids and, more particularly, the tertiary amines can be opioids. In specific embodiments, the present disclosure provides methods for use in processes for the synthesis of naloxone and naltrexone from oripavine. 3. The method of claim 1 , wherein the transition metal catalyst comprises a transition metal selected from the group consisting of Pd[0] claim 1 , Pd[II] claim 1 , Ni[0] claim 1 , Ni[II] claim 1 , Mo[0] claim 1 , Ru[II] claim 1 , Rh[I] claim 1 , and combinations of two or more thereof.4. The method of claim 3 , wherein the transition metal catalyst is selected from the group consisting of Pd(PPh) claim 3 , Pd(PhP(CH)PPh) claim 3 , Ni(PPh) claim 3 , Ni(PhP(CH)PPh) claim 3 , ((pentamethylcyclopentadienyl)RuCl) claim 3 , [Pd(DBA)]/PPh claim 3 , [Pd(OAc)]/PPh claim 3 , [Ni(COD)]/PPh claim 3 , NiCl/PPh claim 3 , Ni[P(OEt)] claim 3 , [Mo(CO)-DPPE] claim 3 , RhH(PPh)-P(n-Bu) claim 3 , and combinations of two or more thereof.6. The method of claim 5 , wherein the solvent is selected from the group consisting of ether solvents claim 5 , acetonitrile claim 5 , benzene claim 5 , N claim 5 ,N-dimethylformamide claim 5 , dimethyl sulfoxide claim 5 , N claim 5 ,N-dimethylpropionamide claim 5 , 1 claim 5 ,3-dimethyl-3 claim 5 ,4 claim 5 ,5 claim 5 ,6-tetrahydro-2(1H)-pyrimidinone claim 5 , 1 claim 5 ,3-dimethyl-2-imidazolidinone claim 5 , 1 claim 5 ,2-dimethoxyethane claim 5 , N claim 5 ,N-dimethylacetamide claim 5 , N-methylpyrrolidinone claim 5 , ethyl acetate claim 5 , ethyl formate claim 5 , ethyl-methyl ketone claim 5 , iso-butylmethylketone claim 5 , formamide claim 5 , hexamethylphosphoramide claim 5 , methyl acetate claim 5 , N-methylacetamide claim 5 , N-methylformamide claim 5 , nitrobenzene claim 5 , nitromethane claim 5 ...

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Номер записи: 4
02-05-2013 дата публикации

METHOD FOR PRODUCING TOLUENEDICARBAMATE, METHOD FOR PRODUCING TOLUENEDIISOCYANATE, AND TOLUENEDICARBAMATE

Номер: US20130109881A1
Автор: Kanno Takashi, KOTAKI Yasushi, MURAYAMA Koichi, SASAKI Masaaki, Shimokawatoko Yoshiki, TAKAMATSU Koji, TAKEUCHI Hiroshi
Принадлежит:

A method for producing toluenedicarbamate includes a carbamate production process of producing toluenedicarbamate by reaction between toluenediamine, urea, and/or N-unsubstituted carbamic acid ester, and alcohol; and a benzoyleneurea reduction process of reducing a disubstituted benzoyleneurea and a derivative thereof to 10 mol or less relative to 100 mol of toluenedicarbamate, wherein the disubstituted benzoyleneurea is represented by formula (1) below and has a methyl group and an amino group: 3. The method for producing toluenedicarbamate according to claim 2 , wherein the biuret compound reduction process comprises a first biuret compound reduction process of reducing a first biuret compound represented by formula (2) above where Xand Xare amino groups.4. The method for producing toluenedicarbamate according to claim 3 , further comprising a urea feeding process of feeding urea to the carbamate production process claim 3 ,wherein in the first biuret compound reduction process,when the urea feeding process includes a fluid feeding process, in which urea is melted by heating to be in a fluid state, and to be fed to the carbamate production process, the time after the melting of urea to the completion of its feeding is set to within 2 hours,in the urea feeding process, urea is fed as a slurry to the carbamate production process, orin the urea feeding process, urea is fed in a solid state to the carbamate production process.5. The method for producing toluenedicarbamate according to claim 2 , wherein the biuret compound reduction process comprises a second biuret compound reduction process of reducing a second biuret compound represented by formula (2) above where Xis an amino group or an alkoxy group and Xis an alkoxy group.6. The method for producing toluenedicarbamate according to claim 5 , further comprising an N-unsubstituted carbamic acid ester production process of producing N-unsubstituted carbamic acid ester by reaction between urea and alcohol claim 5 , ...

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Номер записи: 5
16-05-2013 дата публикации

Process for preparation of lacosamide and some n-benzyl-propanamide intermediate derivatives

Номер: US20130123522A1
Автор: Aditi Milind Panandikar, Mangesh Narayan Rajadhyaksha, Nilesh Balkrishna Shrigadi, Ranjeet Nair
Принадлежит: Indoco Remedies Ltd

The present invention discloses novel process for the preparation of (2R)-2-acetamido-N-benzyl-3-methoxypropanamide of Formula I involving novel intermediates of Formula-XIX and Formula-XX.

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Номер записи: 6
20-06-2013 дата публикации

NEW PROCESS FOR THE PREPARATION OF INTERMEDIATES USEFUL FOR THE MANUFACTURE NEP INHIBITORS

Номер: US20130158275A1
Автор: Bappert Erhard, Hook David, Li Yunzhong, Riss Bernhard, ZHOU Jianguang
Принадлежит: NOVARTIS AG

The invention relates to a new process for producing useful intermediates for the manufacture of NEP inhibitors or prodrugs thereof, in particular NEP inhibitors comprising -amino- -biphenyl- -methylalkanoic acid, or acid ester, backbone, such as N-(3-carboxyl-1-oxopropyl)-(4S)-(p-phenylphenylmethyl)-4-amino-(2R)-methyl butanoic acid ethyl ester or salt thereof. 2. A process according to wherein the transition metal catalyst comprises Palladium (Pd).5. A process according to claim 4 , wherein the reduction reaction is carried out with hydrogen in the presence of a transition metal catalyst.8. A process according to claim 7 , wherein the reduction reaction is carried out with hydrogen in the presence of a transition metal catalyst.11. The compound according to whereinR1 is hydrogen;R2 is BOC; andR3 is a carboxyl group; orR1 and R2 are hydrogen; andR3 is a carboxyl group13. The use of a compound according to claim 9 , in the synthesis of an NEP-inhibitor or a prodrug thereof claim 9 , such as a NEP inhibitor or prodrug thereof comprising a -amino- -biphenyl- -methylalkanoic acid claim 9 , or acid ester claim 9 , backbone14. The use according to claim 13 , wherein the NEP-inhibitor is N-(3-carboxy-1-oxopropyl)-(4S)-(p-phenylphenylmethyl)-4-amino-(2R)-methylbutanoic acid or a salt or a prodrug thereof.15. The use according to claim 14 , wherein the NEP-inhibitor prodrug is N-(3-carboxyl-1-oxopropyl)-(4S)-(p-phenylphenylmethyl)-4-amino-(2R)-methyl butanoic acid ethyl ester or salt thereof.16. A process for preparing N-(3-carboxyl-1-oxopropyl)-(4S)-(p-phenylphenylmethyl)-4-amino-(2R)-methyl butanoic acid ethyl ester claim 9 , or a salt thereof claim 9 , comprising the manufacture of compound of formula (4) claim 9 , or salt thereof claim 9 , as defined in . The invention relates to a new process for producing useful intermediates for the manufacture of NEP inhibitors or prodrugs thereof, in particular NEP inhibitors comprising a γ-amino-δ-biphenyl-α-methylalkanoic acid, ...

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Номер записи: 7
20-06-2013 дата публикации

PROCESS FOR THE PREPARATION OF INTERMEDIATES FOR THE MANUFACTURE OF NEP INHIBITORS

Номер: US20130158285A1
Автор: Hook David, Li Yunzhong, ZHOU Jianguang
Принадлежит: NOVARTIS AG

The invention relates to a new process for producing useful intermediates for the manufacture of NEP inhibitors or prodrugs thereof, in particular NEP inhibitors comprising a γ-amino-δ-biphenyl-α-methylalkanoic acid, or acid ester, backbone, such as N-(3-carboxyl-1-oxopropyl)-(4S)-(p-phenylphenylmethyl)-4-amino-(2R)-methyl butanoic acid ethyl ester or salt thereof. 2. A process according to wherein the transition metal catalyst comprises Palladium (Pd).3. A process according to wherein the transition metal catalyst is Pd(PPh).4. A process according to whereinR1 is hydrogen;R2 is BOC; andR3 is a carboxyl group.5. A process for preparing N-(3-carboxyl-1-oxopropyl)-(4S)-(p-phenylphenylmethyl)-4-amino-(2R)-methyl butanoic acid ethyl ester claim 1 , or a salt thereof claim 1 , comprising the manufacture of compound of formula (3) claim 1 , or salt thereof claim 1 , as defined in .6. A process for preparing N-(3-carboxyl-1-oxopropyl)-(4S)-(p-phenylphenylmethyl)-4-amino-(2R)-methyl butanoic acid claim 1 , or a salt thereof claim 1 , or a prodrug thereof claim 1 , comprising the manufacture of compound of formula (3) claim 1 , or salt thereof claim 1 , as defined in . The invention relates to a new process for producing useful intermediates for the manufacture of NEP inhibitors or prodrugs thereof, in particular NEP inhibitors comprising a γ-amino-δ-biphenyl-α-methylalkanoic acid, or acid ester, backbone.Endogenous atrial natriuretic peptides (ANP), also called atrial natriuretic factors (ANF) have diuretic, natriuretic and vasorelaxant functions in mammals. The natural ANF peptides are metabolically inactivated, in particular by a degrading enzyme which has been recognized to correspond to the enzyme neutral endopeptidase (NEP, EC 3.4.24.11), also responsible for e.g. the metabolic inactivation of enkephalins.In the art biaryl substituted phosphonic acid derivatives are known which are useful as neutral endopeptidase (NEP) inhibitors, e.g. as inhibitors of the ANF- ...

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Номер записи: 8
11-07-2013 дата публикации

Method for Producing Carbonyl Compund

Номер: US20130178645A1
Автор: Miyake Nobuhisa, Shinohata Masaaki
Принадлежит: ASAHI KASEI CHEMICALS CORPORATION

A method for producing a carbonyl compound of the present invention comprises a step (X) of reacting a specific compound having a urea bond with a carbonic acid derivative having a carbonyl group (—C(═O)—) under heating at a temperature equal to or higher than the thermal dissociation temperature of the urea bond to obtain the carbonyl compound. 2. The method for producing the carbonyl compound according to claim 1 , wherein the step (X) is carried out in the coexistence of a hydroxy compound.3. The method for producing the carbonyl compound according to claim 1 , wherein the carbonyl compound comprises an N-substituted carbamic acid ester.4. The method for producing the carbonyl compound according to claim 1 , wherein the carbonic acid derivative is urea or an N-unsubstituted carbamic acid ester.5. The method for producing the carbonyl compound according to claim 1 , wherein the carbonic acid derivative is a carbonic acid ester.7. The method for producing the carbonyl compound according to claim 1 , wherein the compound having the urea bond is a polyurethane-urea copolymer.9. The method for producing the carbonyl compound according to claim 8 , wherein the compound having the urea bond is a compound produced from an organic primary amine and a phosgene.10. The method for producing the carbonyl compound according to claim 1 , wherein the step (X) is carried out in a distillation column.11. A method for producing an isocyanate claim 1 , comprising a step of subjecting a carbonyl compound obtained by the production method according to claim 1 , to a pyrolytic reaction to produce the isocyanate.12. The method for producing the carbonyl compound according to claim 1 , whereinthe step (X) is carried out using a distillation column comprising a supply port A, a supply port B, and a discharge port C;the step (X) comprises steps of:supplying raw material ingredients containing the compound having the urea bond, or raw material ingredients containing a precursor of the ...

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Номер записи: 9
05-09-2013 дата публикации

METAL CARBAMATES FORMED FROM TOLYLENEDIAMINES

Номер: US20130231495A1
Автор: Baumann Robert, LEITNER Andreas, SIEGEL Wolfgang
Принадлежит: BASF SE

The invention provides metal carbamates of the general formula (I) 1. (canceled)3. The process according to claim 2 , wherein the alkyl groups R1 and R2 each comprise 2-18 carbon atoms in the chain.4. The process according to claim 2 , wherein the alkyl groups R1 and R2 each comprise 2-7 carbon atoms in the chain.5. The process according to claim 2 , wherein the alkyl groups R1 and R2 are selected from the group consisting of an ethyl claim 2 , propyl claim 2 , butyl claim 2 , 2-methylpropyl claim 2 , 3-methylbutyl claim 2 , n-pentyl claim 2 , 2-methoxyethyl claim 2 , 2-ethoxyethyl and a 2 claim 2 ,2 claim 2 ,2-trifluoroethyl group.6. The process according to claim 2 , wherein the alkyl groups comprise one or more heteroatoms.7. The process according to claim 2 , wherein the alkyl groups comprise one or more oxygen atoms.8. The process according to claim 2 , wherein no heteroatoms are present in R1 and R2.9. The process according to claim 2 , wherein R1 and R2 are identical.10. The process according to claim 2 , wherein R1 and R2 are branched or unbranched.11. The process according to claim 2 , wherein the metal carbamate is solid at room temperature. This application is a divisional of U.S. application Ser. No. 12/920,224 filed Aug. 30, 2010, which is a National Stage of PCT/EP2009/053170 filed Mar. 18, 2009, both of which are incorporated herein by reference. This application also claims the benefit of EP 08152943.0 filed Mar. 18, 2008.The invention provides metal carbamates formed from tolylenediamines and a process for preparing them.Carbamates have been known for a long time. They are prepared typically by reacting aromatic amines with stoichiometric amounts of a base and an organic carbonate.For the preparation of carbamates, a series of processes is known.In these processes, for example, Lewis acids, such as uranium salts (U.S. Pat. No. 3,763,217), aluminum turnings with iodine and Hg promoters (U.S. Pat. No. 4,550,188), zinc salts, iron salts, antimony salts ...

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Номер записи: 10
19-09-2013 дата публикации

PREPARATION OF PET PRECURSOR

Номер: US20130245307A1
Автор: Berg Tom Christian, Nilsen Anne
Принадлежит: GE HEALTHCARE LIMITED

The invention relates to a process for preparation of radiopharmaceutical precursors, and in particular protected amino acid derivatives which are used as precursors for production of radiolabeled amino acids for use in in vivo imaging procedures such as positron emission tomography (PET). Particularly, the invention relates to a process for preparation of a precursor of the [F]-1-amino-3- fluorocyclobutanecarboxylic acid ([F] FACBC) PET agent and particularly to the work-up process of this precursor removing generated salts from the intermediate composition. 2. A process as claimed in wherein X is benzyl.3. A process as claimed in either or wherein R is ethyl.4. A process as claimed in any one of to wherein Y is tent-butyl carbamate (Boc).6. A process as claimed in any one of to wherein in step iii) the amount of water added is about half the amount of ethyl acetate added in step ii).7. A process as claimed in any one of to wherein in step iv) the acid added is HCl.8. A process as claimed in any one of to wherein in step iv) the washing includes washing with pure water claim 1 , with an aqueous solution of sodium hydrogen carbonate and with brine.9. A process as claimed in any one of to further including the steps of concentrating the composition from step iv) under reduced pressure claim 1 , drying and purifying.10. A process as claimed in any one of to wherein the crude reaction product includes a mixture of the syn- and anti-enantiomer of the compound of formula IIIa.12. A process as defined in wherein said leaving group is a halogen substituent or a group represented by —ORwherein Ris either a fluorosulfonic acid substituent or an aromatic sulfonic acid substituent.13. A process as defined in wherein said leaving group is selected from a toluenesulfonic acid substituent claim 12 , a nitrobenzenesulfonic acid substituent claim 12 , a benzenesulfonic acid substituent claim 12 , a trifluoromethanesulfonic acid substituent claim 12 , a fluorosulfonic acid ...

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Номер записи: 11
10-10-2013 дата публикации

Purificiation of precursor compound by crystallisation

Номер: US20130267730A1
Автор: Anne Nilsen, Sondre NILSEN
Принадлежит: GE Healthcare Ltd

The invention relates to a process for preparation of radiopharmaceutical precursors, and in particular protected amino acid derivatives which are used as precursors for production of radiolabelled amino acids for use in vivo imaging procedures such as positron emission tomography (PET). Particularly, the invention relates to a process for preparation of a precursor useful in the preparation of the [ 18 F]-1-amino-3-fluorocyclobutanecarboxylic acid ([ 18 F] FACBC) PET tracer.

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Номер записи: 12
24-10-2013 дата публикации

METAL CARBAMATES FORMED FROM DIAMINOPHENYLMETHANE

Номер: US20130281727A1
Автор: Baumann Robert, LEITNER Andreas, SIEGEL Wolfgang
Принадлежит:

The invention provides metal carbamates of the general formula (I) 1. (canceled)3. The process of claim 2 , wherein claim 2 , in formula (I) claim 2 , the alkyl groups Rand Reach comprise 2-18 carbon atoms in the chain.4. The process of claim 2 , wherein claim 2 , in formula (I) claim 2 , the alkyl groups Rand Reach comprise 2-7 carbon atoms in the chain.5. The process of claim 2 , wherein claim 2 , in formula (I) claim 2 , the alkyl groups Rand Rare each independently an ethyl claim 2 , propyl claim 2 , butyl claim 2 , 2-methylpropyl claim 2 , 3-methylbutyl claim 2 , n-pentyl claim 2 , 2-methoxyethyl claim 2 , 2-ethoxyethyl claim 2 , or a 2 claim 2 ,2 claim 2 ,2-trifluoroethyl group.6. The process of claim 2 , wherein claim 2 , in formula (I) claim 2 , the alkyl groups Rand Rcomprise heteroatoms.7. The process of claim 6 , wherein the heteroatoms are halogen atoms.8. The process of claim 6 , wherein the heteroatoms are fluorine atoms.9. The process of claim 6 , wherein the heteroatoms are chlorine atoms.10. The process of claim 6 , wherein the heteroatoms are oxygen atoms.11. The process of claim 6 , wherein the heteroatoms are oxygen atoms present in the form of ether groups.12. The process of claim 2 , wherein claim 2 , in formula (I) claim 2 , the alkali metal ion is lithium.13. The process of claim 2 , wherein claim 2 , in formula (I) claim 2 , the alkali metal ion is sodium.14. The process of claim 2 , wherein claim 2 , in formula (I) claim 2 , the alkali metal ion is potassium.15. The process of claim 2 , wherein claim 2 , in formula (I) claim 2 , wherein Rand Rare identical.16. The process of claim 3 , wherein claim 3 , in formula (I) claim 3 , Rand Rare identical.17. The process of claim 4 , wherein claim 4 , in formula (I) claim 4 , Rand Rare identical.18. The process of claim 5 , wherein claim 5 , in formula (I) claim 5 , Rand Rare identical.19. The process of claim 6 , wherein claim 6 , in formula (I) claim 6 , Rand Rare identical. This application is a ...

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Номер записи: 13
26-12-2013 дата публикации

PROCESS FOR THE PREPARATION OF RETIGABINE

Номер: US20130345465A1
Автор: Fitzgerald Russ N., Millar Alan, Toczko Jennifer Fell
Принадлежит: Glaxo Group Limited

This invention relates to a novel chemical process for the synthesis of 2-ethyoxycarbonylamino-5-(4-fluorobenzylamino)-nitrobenzene and its use in the preparation of 2-amino-4-(4-fluorobenzylamino)-1-ethoxycarbonylaminobenzene (retigabine/ezogabine) and its polymorphic forms thereof. 2. A process as claimed in for the preparation of a compound of formula (I) or a salt thereof claim 1 , which further comprises reaction of 4-fluorobenzaldehyde and 4-amino-2-nitroaniline followed by reduction using standard procedures to produce a compound of formula (II).3. A process for the preparation of retigabine claim 1 , or a salt thereof claim 1 , which comprises the following steps:(i) reacting a compound of formula (II) with diethylcarbonate in the presence of a base to produce a compound of formula (I), or a salt thereof; and(ii) reduction of compound of formula (I) using standard procedures to produce retigabine;(iii) and optionally preparing a salt thereof.4. A process as claimed in for the preparation of retigabine claim 3 , or a salt thereof claim 3 , which further comprises reaction of 4-fluorobenzaldehyde and 4-amino-2-nitroaniline followed by reduction using standard procedures to produce a compound of formula (II).5. A process as claimed in wherein the base is selected from sodium ethoxide claim 1 , sodium hydride claim 1 , potassium tert-butoxide claim 1 , n-butyl lithium claim 1 , potassium hexamethyldisilylazide (KHMDS) claim 1 , cesium carbonate claim 1 , potassium hydroxide claim 1 , sodium pentoxide claim 1 , sodium tert-butoxide claim 1 , lithium ethoxide claim 1 , sodium hydroxide claim 1 , potassium ethoxide claim 1 , diisopropyl ethyl amine (DIPEA) claim 1 , 1 claim 1 ,8-diazabicylco[5.4.0]undec-7-ene (DBU) claim 1 , 1 claim 1 ,4-diazabicyclo[2.2.2]octane (DABCO) or lithium tert-butoxide.6. A process as claimed in wherein the base is sodium ethoxide.7. A process as claimed in wherein the base is present in range of 1.8 to 2.2 molar equivalents.8. A process ...

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Номер записи: 14
20-02-2014 дата публикации

PREPARING METHOD OF SOLID CARBAMIC ACID DERIVATIVES

Номер: US20140051858A1
Автор: HUR Nam Hwi, LEE Byeong No
Принадлежит: SOGANG UNIVERSITY RESEARCH FOUNDATION

The present disclosure relates to a preparation method for powder of a carbamic acid derivative, which includes reacting a liquid amine derivative with carbon dioxide at a temperature in a range of from about −30° C. to about 500° C. at a pressure in a range of from about 0.3 MPa to about 100 MPa. In addition, the present disclosure relates to a reduction method for powder of a carbamic acid derivative to a liquid amine derivative and carbon dioxide, which includes dissolving powder of the carbamic acid derivative prepared in a solvent; refluxing the carbamic acid derivative at a temperature in a range of from about 30° C. to about 100° C.; and evaporating the solvent. The preparation method for a carbamic acid derivative powder according to the present disclosure enables easy conversion into pure powder of solid carbamic acid derivative without by-products and can remarkably reduce time and energy required for solidification by reacting carbon dioxides and amines with carbon dioxides in high pressure conditions without the use of a solvent. In addition, the prepared solid compounds can be used as a liquid amine substitute or used in a carbamic acid derivative form as necessary. 1. A preparation method for powder of a carbamic acid derivative , the method comprising:reacting a liquid amine derivative with carbon dioxide at a temperature in a range of from about −30° C. to about 500° C. at a pressure in a range of from about 0.3 MPa to about 100 MPa.4. The preparation method of claim 1 ,wherein a content of an amine group (—NH) in the amine derivative is from about 50 wt % to about 99 wt %.5. The preparation method of claim 1 ,wherein the temperature is in a range of from about 0° C. to about 300° C.6. The preparation method of claim 1 ,wherein the pressure is in a range of from about 1 MPa to about 50 MPa.7. The preparation method of claim 1 , the method including:reacting a mixed solution of the liquid amine derivative with ethers, alcohols, aliphatic hydrocarbons, ...

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Номер записи: 15
11-01-2018 дата публикации

LOW BY-PRODUCT CONTENT POLYPHENYLENE POLYMETHYLENE POLYISOCYANATES

Номер: US20180009742A1
Автор: Baumann Robert, Bock Michael, Franzke Axel, Janssens Geert, Lorenz Michael
Принадлежит: BASF SE

The invention relates to polyphenyl polymethylene polyisocyanates having an NCO number of at least 29% comprising less than 2% by weight ureas, less than 8% by weight carbodiimides or uretonimines and less than 1000 ppm organic chlorine compounds. 1. A method for preparing a polyphenyl polymethylene polyisocyanate having an NCO number , determined according to DIN EN ISO 14896 , of at least 29% comprising less than 2% by weight ureas , determined by NMR , less than 8% by weight carbodiimides or uretonimines , determined by NMR , and less than 1000 ppm organic chlorine compounds , determined by high-resolution mass spectrometry or according to ASTM D4663-10 , the method comprising:reacting a polyphenyl polymethylene polyamine with an organic carbonate to give a corresponding polyphenyl polymethylene polycarbamate,thermally cleaving the polyphenyl polymethylene polycarbamate to give the polyphenyl polymethylene polyisocyanate; andprior to the thermally cleaving, reacting free amino groups or urea groups present in a carbamate crude mixture comprising the polyphenyl polymethylene polycarbamate with a derivatizing reagent to give amide groups or urethane groups.2. The method according to claim 1 , wherein the derivatizing reagent comprises at least one selected from the group consisting of an ester claim 1 , an acid anhydride claim 1 , and an acyl chloride of an aliphatic carboxylic acid having 1 to 10 carbon atoms or an aromatic carboxylic acid having 7 to 14 carbon atoms.3. The method according to claim 1 , wherein the derivatizing reagent comprises at least one of acetic anhydride and acetyl chloride.4. The method according to claim 1 , wherein the derivatizing reagent comprises at least one of a chloroformic ester and a pyrocarbonate of C-C-alkanols5. The method according to claim 1 , wherein the reacting of the free amino groups or the urea groups with the derivatizing reagent is carried out in a solvent.6. The method according to claim 5 , wherein the solvent is ...

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Номер записи: 16
10-01-2019 дата публикации

METHOD FOR CLEAVING AMIDE BONDS

Номер: US20190010113A1
Автор: HARRIS Craig Steven, JING JING Laura, Olsson Johan
Принадлежит: GALDERMA S.A.

A method for cleaving amide bonds, comprising: 130-. (canceled)31. A method for cleaving amide bonds , comprising:a) providing a molecule comprising an amide group, wherein the amide group is a primary, secondary or tertiary amide group;{'sub': '2', 'b) reacting the molecule comprising an amide group with hydroxylamine (NHOH) or a salt thereof to cleave the amide bond of the amide group.'}32. The method according to claim 31 , wherein the method further comprises:c) recovering a product formed by the reaction of step b).33. The method according to claim 31 , wherein the amide group is an N-acyl amide group.34. The method according to claim 31 , wherein the molecule comprising an amide group further comprises a pH sensitive chiral center.35. The method according to claim 31 , wherein the molecule comprising an amide group further comprises a pH sensitive protecting group.36. The method according to claim 31 , wherein step b) comprises reacting the molecule comprising an amide group with the hydroxylamine or salt thereof at a temperature of 100° C. or less.37. The method according to claim 31 , wherein step b) comprises reacting the molecule comprising an amide group with the hydroxylamine or salt thereof for 2-200 hours.38. The method according to claim 31 , wherein step b) comprises reacting the molecule comprising an amide group with hydroxylamine in water.39. The method according to claim 31 , wherein the molar concentration of hydroxylamine in step b) is in the range of 5-20 M.40. The method according to claim 31 , wherein step b) comprises reacting the molecule comprising an amide group with a hydroxylamine salt.41. The method according to claim 40 , wherein the hydroxylamine salt is a salt of hydroxylamine and hydroiodic acid or trifluoroacetic acid.42. The method according to claim 31 , wherein the concentration of the hydroxylamine salt in step b) is in the range of 0.1-5 M.43. The method according to claim 31 , wherein the reaction in step b) is performed in ...

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Номер записи: 17
09-01-2020 дата публикации

PROCESS FOR THE PREPARATION OF MONO-PROTECTED ALPHA,OMEGA-DIAMINO ALKANES

Номер: US20200010408A1
Автор: MENGE Wiro Michael Petrus Bernardus
Принадлежит:

The present invention relates to a process for the synthesis of mono-protected α,ω-diamino alkanes, the use of said process in a process for the synthesis of a linker drug comprising an α,ω-diamino alkane moiety and the use of the process of the present invention in a process for preparing an antibody-drug conjugate comprising an α,ω-diamino alkane moiety. 2. The process according to claim 1 , wherein R is Calkyl and Ris selected from H claim 1 , (CH)OCH claim 1 , (CHCHO)H claim 1 , (CHCHO)CH claim 1 , (CH)NHP claim 1 , (CH)N(CH) claim 1 , (CH)NHCONH claim 1 , (CH)NHSOCH claim 1 , (CH)SONH claim 1 , optionally substituted Calkyl claim 1 , optionally substituted Ccycloalkyl and optionally substituted Cheterocycloalkyl.3. The process according to claim 1 , wherein R is CHand Ris selected from (CH)OCH claim 1 , (CHCHO)H claim 1 , (CHCHO)CHand optionally substituted Calkyl.4. The process according to claim 1 , wherein the coupling reagent is selected from the group consisting of carbodiimide reagents claim 1 , phosphonium reagents and aminium reagents.5. The process according to claim 1 , wherein the borane reagent is borane claim 1 , diborane or a borane-ligand complex.6. The process according to claim 5 , wherein the borane reagent is a borane-ligand complex selected from borane tetrahydrofuran or borane dimethyl sulfide.7. The process according to claim 1 , wherein the protective group P is selected from the group consisting of 1 claim 1 ,1-dimethyl-2-haloethyl carbamate claim 1 , 1 claim 1 ,1-dimethyl-2 claim 1 ,2-dibromoethyl carbamate claim 1 , t-butyl carbamate claim 1 , 1-adamantyl carbamate claim 1 , N-(2-pivaloylamino)-1 claim 1 ,1-dimethylethyl carbamate claim 1 , 2-[(2-nitrophenyl)dithio]-1-phenylethyl carbamate claim 1 , 9-anthrylmethyl carbamate claim 1 , methyl carbamate claim 1 , ethyl carbamate claim 1 , p-methoxybenzyl carbamate claim 1 , N-hydroxypiperidinyl claim 1 , p-nitrobenzyl carbamate claim 1 , diphenylmethyl carbamate claim 1 , m-chloro-p- ...

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Номер записи: 18
19-01-2017 дата публикации

Two-step and one-pot processes for preparation of aliphatic diisocyanates

Номер: US20170015621A1
Автор: Shenghong A. Dai, Wei Hsing LIN, Yi-Syuan GUO
Принадлежит: Great Eastern Resins Industrial Co Ltd

The present invention relates to using a two-step (thermolysis) or one-pot process to prepare aliphatic diisocyanates from aliphatic diamines and diaryl carbonates. Polyisocyanates can also be prepared from polyamines and diaryl carbonates. The present synthetic processes do not apply phosgene or highly toxic reagents and chloro-solvents during the entire procedure.

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Номер записи: 19
19-01-2017 дата публикации

CYCLOPROPENE AMINO ACIDS AND METHODS

Номер: US20170015623A1
Автор: Elliott Thomas
Принадлежит:

The invention relates to a polypeptide comprising an amino acid having a cyclopropene group wherein said cyclopropene group is joined to the amino acid via a carbamate group. Suitably the cyclopropene group is a 1,3-disubstituted cyclopropene such as a 1,3-dimethylcyclopropene. Suitably the cyclopropene group is present as a residue of a lysine amino acid. The invention also relates to methods of making the polypeptides. The invention also relates to an amino acid comprising cyclopropene wherein said cyclopropene group is joined to the amino acid moiety via a carbamate group. 1. A polypeptide comprising an amino acid having a cyclopropene group wherein said cyclopropene group is joined to the amino acid via a carbamate group.2. A polypeptide according to wherein said cyclopropene group is a 1 claim 1 ,3-disubstituted cyclopropene.3. A polypeptide according to wherein said cyclopropene is a 1 claim 2 ,3-dimethylcyclopropene.4. A polypeptide according to wherein said cyclopropene group is present as a residue of a lysine amino acid.5. A polypeptide according to further comprising a tetrazine compound linked to said cyclopropene group.6. An amino acid comprising cyclopropene wherein said cyclopropene group is joined to the amino acid moiety via a carbamate group.7. An amino acid according to wherein said cyclopropene is a 1 claim 6 ,3-disubstituted cyclopropene.8. An amino acid according to wherein said cyclopropene is a 1 claim 7 ,3-dimethylcyclopropene.9. An amino acid according to wherein said amino acid is a lysine amino acid.10. An amino acid according to which comprises N-[((2-methylcycloprop-2-en-1-yl)methoxy)carbonyl]-1-lysine.12. A method of producing a polypeptide comprising a cyclopropene group wherein said cyclopropene group is joined to an amino acid moiety of the polypeptide via a carbamate group claim 9 , said method comprising genetically incorporating said amino acid comprising said cyclopropene group joined to said amino acid moiety via said carbamate ...

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Номер записи: 20
17-01-2019 дата публикации

ORGANIC AMINE SALT COMPOUNDS HAVING CO2-DONATING ANIONS AND THEIR USE AS FOAMING AGENT

Номер: US20190016673A1
Автор: BI Gehua, BI Yusui
Принадлежит: Shandong University of Technology

An organic amine salt compounds of general formula A[B](I) is disclosed, wherein A is a CO-donating anion with a valence of −n, wherein n=1, 2 or 3; each B comprises: ammonium ion, hydrazinium ion and/or organic amine B cation; wherein 49. The foaming agent according to claim 48 , wherein (1a) H[OCH(R)CH(R)]— is H(OCHCH)— claim 48 , H(OCHCH(CH))— claim 48 , H(OCH(CH)CH)— claim 48 , H(OCHCH(CH))— claim 48 , H(OCH(CH)CH)— claim 48 , H(OCHCH(CHCl))— claim 48 , H(OCH(CHCl)CH)— or H(OCHCH(CBr))—.50. The foaming agent according to claim 48 , wherein: the water content in the foaming agent is from >0 wt % to 40 wt %; and/orthe pH of the foaming agent is 7.5-10.51. The foaming agent according to claim 50 , wherein: the water content in the foaming agent is 5-35 wt %; and/orthe pH of the foaming agent is 7.8-9.5.52. The foaming agent according to claim 51 , wherein: the water content in the foaming agent is 10-30 wt %; and/orthe pH of the foaming agent is 8-9.5.53. The foaming agent according to claim 52 , wherein: the water content in the foaming agent is 15-25 wt %.54. The foaming agent according to claim 48 , wherein: the total content of the compounds of the general formula (I) and water in the foaming agent is 70-100 wt % claim 48 , based on the total weight of the foaming agent.55. The foaming agent according to claim 54 , wherein: the total content of the compounds of the general formula (I) and water in the foaming agent is 80-99.999% claim 54 , based on the total weight of the foaming agent.56. The foaming agent according to claim 55 , wherein: the total content of the compounds of the general formula (I) and water in the foaming agent is 85-99.0% claim 55 , based on the total weight of the foaming agent.58. The foaming agent according to claim 57 , wherein the organic amine compound (B) is an organic amine compound having N—R group(s) claim 57 , and the organic amine compound (B) having N—R group(s) is formed by substitution on ammonia or on at least one N atom of ...

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Номер записи: 21
23-01-2020 дата публикации

PRODUCING AMMONIUM CARBAMATE AND REDUCING NITROGEN OXIDES

Номер: US20200023312A1
Автор: HARGRAVE Graham, Wilson Jonathan
Принадлежит:

A process for reducing nitrogen oxides in an exhaust stream, such as a vehicle exhaust stream, and apparatus for carrying out the process. The process comprises providing a first composition comprising aqueous urea, a second composition comprising ammonium carbamate and an exhaust stream comprising nitrogen oxides. A process for producing the ammonium carbamate is also provided. The second composition may be introduced into the exhaust stream () when the exhaust stream has a temperature below a threshold temperature and the first composition may be introduced into the exhaust stream when the exhaust stream has a temperature at or above the threshold temperature. 1. A process for reducing nitrogen oxides in an exhaust stream , the process comprisingproviding a first reservoir having the first composition therein, the first composition comprising aqueous urea;transferring a portion of the first composition along a flow path, the flow path being in communication with a second reservoir;heating the portion of the first composition to produce a mixture comprising ammonia, carbon dioxide and water; the heating taking place in the flow path or in the second reservoir;cooling the mixture to generate a second composition, the second composition comprising aqueous ammonium carbamate and the cooling taking place in the flow path or in the second reservoir;introducing the second composition from the second reservoir into an exhaust stream comprising nitrogen oxides.2. The process of claim 1 , wherein the first composition is not introduced into the exhaust stream.3. The process of claim 1 , wherein the second composition is introduced into the exhaust stream when the exhaust stream has a temperature below a threshold temperature and the first composition is introduced into the exhaust stream when the exhaust stream has a temperature at or above the threshold temperature.4. The process of claim 3 , wherein (i) the threshold temperature is at least 250° C.; and/or (ii) the ...

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Номер записи: 22
04-02-2016 дата публикации

Methods of Producing Cancer Compounds

Номер: US20160030589A1
Автор: Fu Xiong, Hutchison Jeff, Kunnen Kevin, Lynch John K
Принадлежит: Genspera, Inc.

Provided is a method for making the compound of Formula 1: 2. The method of claim 1 , wherein step (a) is performed using sodium ethoxide in ethanol.3. The method of claim 1 , wherein step (b) is performed using 4-dimethylaminopyridine (4-DMAP) claim 1 , the compound of Formula 4 claim 1 , dichloromethane and diisopropylcarbodiimide (DIC).4. The method of claim 1 , wherein the dissolution in step (c) is performed using dichloromethane (CHCl).5. The method of claim 1 , wherein step (e) is performed using dichloromethane claim 1 , triethylsilane (EtSiH) and trifluoroacetic acid.6. The method of any of claim 1 , wherein step (f) is performed using C18 reverse-phase chromatography.7. The method of claim 6 , wherein step (f) further comprises using a concentration column.9. A method for making a compound having the formula Boc-(CH)—NH claim 8 , wherein n is an integer greater than 2 claim 8 , using the method of claim 8 , wherein the starting material for such method is a compound having the formula (CH)—NH claim 8 , wherein n is an integer greater than 2.10. A compound having a formula selected from: Formula 1 claim 8 , Formula 2 claim 8 , Formula 3 claim 8 , Formula 4 claim 8 , Formula 5 claim 8 , Formula 6 claim 8 , Formula 7 claim 8 , Formula 8 claim 8 , Formula 9 claim 8 , Formula 10 claim 8 , Formula 11; and Formula 12.11. A compound having the formula of the compound shown in .12. A compound having the formula Boc-(CH)—NH claim 8 , wherein n is an integer greater than 2.13. A compound produced by the method of .15. The method of claim 14 , wherein step (a) is performed using sodium ethoxide in ethanol.16. The method of claim 14 , wherein step (b) is performed using 4-dimethylaminopyridine (4-DMAP) claim 14 , the compound of Formula 4 claim 14 , dichloromethane and diisopropylcarbodiimide (DIC).17. The method of wherein the dissolution in step (c) is performed using dichloromethane (CHCl).18. A compound produced by the method of .19. The method of claim 14 , ...

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Номер записи: 23
24-04-2014 дата публикации

PROCESS FOR THE PREPARATION OF 6-(7-((1-AMINOCYCLOPROPYL)METHOXY)-6-METHOXYQUINOLIN-4-YLOXY)-N-METHYL-1-NAPHTHAMIDE AND SYNTHETIC INTERMEDIATES THEREOF

Номер: US20140114075A1
Автор: LIVI Valeria, SPINELLI Silvano
Принадлежит: EOS ETHICAL ONCOLOGY SCIENCE S.p.A. in abbreviated form EOS S.p.A.

A process for the preparation in high yields and purity of the compound 6-(7-((1-aminocyclopropyl)methoxy)-6-methoxyquinolin-4-yloxy)-N-methyl-1-naphthamide of formula (I) and of the pharmaceutically acceptable salts thereof is described. The process has various advantages over those previously described, in particular it avoids the use of acyl azide intermediates and their Curtius rearrangement. Novel intermediates useful for the preparation of compound (I) are also described. 2. The process of wherein R′ is hydrogen and R is selected from the group consisting of benzyl optionally substituted on the aromatic ring with up to three substituents selected from the group consisting of halogen claim 1 , cyano claim 1 , trifluoromethyl; C-Cacyl claim 1 , C-Caroyl claim 1 , C-Calkylsulfonyl claim 1 , C-Carylsulfonyl claim 1 , C-Calkoxycarbonyl claim 1 , benzyloxycarbonyl optionally substituted on the aromatic ring with up to three substituents selected from the group consisting of halogen claim 1 , cyano claim 1 , trifluoromethyl.3. The process of wherein R is selected from the group consisting of benzyl claim 2 , acetyl claim 2 , benzoyl claim 2 , trifluoromethanesulfonyl claim 2 , benzenesulfonyl claim 2 , p-toluenesulfonyl claim 2 , methoxycarbonyl claim 2 , ethoxycarbonyl claim 2 , tert-butoxycarbonyl claim 2 , allyloxycarbonyl claim 2 , benzyloxycarbonyl.4. The process of wherein R′ is tri (C-Calkyl)silyl and R is C-Calkoxycarbonyl or benzyloxycarbonyl optionally substituted on the aromatic ring with up to three substituents selected from the group consisting of halogen claim 1 , cyano claim 1 , trifluoromethyl.5. The process of wherein R′ is trimethylsilyl and R is tert-butoxycarbonyl.6. The process of wherein R and R′ together with the nitrogen atom they are linked to form a phthalimido group.12. A compound as claimed in claim 7 , wherein said compound is:1-[(4-Acetyl-2-methoxyphenoxy)methyl]-N-benzyloxycarbonyl-1-aminocyclopropane.13. Method of synthesizing a ...

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Номер записи: 24
01-02-2018 дата публикации

Process for making lysine-glutamic acid dipeptide derivatives

Номер: US20180029978A1
Автор: Kurt Puentener
Принадлежит: Hoffmann La Roche Inc

The invention relates to compounds of the formula and to a process for making same and to the use of the products in the solid phase peptide synthesis. The compounds of formula I are versatile peptide intermediates for the solid phase peptide synthesis (SPPS) of peptide drugs which comprise a Glu-fatty alkyl side chain building block attached to a Lys-part of the peptide chain.

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Номер записи: 25
31-01-2019 дата публикации

PROCESS TO PREPARE HIGHER ETHYLENE AMINES AND ETHYLENE AMINE DERIVATIVES

Номер: US20190031597A1
Автор: EDVINSSON Rolf Krister, KANTZER Eike Nicolas, LAKE Karl Fredrik, LARSSON Per Fredrik Olmo, TEN KATE Antoon Jacob Berend
Принадлежит: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.

The present invention relates to a process to prepare ethyleneamines of the formula NH—(CH—NH—)H wherein p is at least 3 or derivatives thereof wherein one or more units —NH—CH—NH— may be present as a cyclic ethylene urea unit or between two units —NH—CH—NH— a carbonyl moiety is present, by reacting an ethanolamine-functional compound, an amine-functional compound in the presence of a carbon oxide delivering agent, wherein the molar ratio of ethanolamine-functional compound to amine-functional compound is at least 0.7:1 and the molar ratio of carbon oxide delivering agent to amine-functional compound is at least 0.05:1. 2. Process of wherein the molar ratio of ethanolamine-functional compound to amine-functional compound is between 0.8 and 5:1 and the molar ratio of carbon oxide delivering agent to amine functional compound is between 0.2:1 and 20:1.3. Process of wherein the molar ratio of ethanolamine-functional compound to amine-functional compound is between 1:1 and 2:1 and the molar ratio of carbon oxide delivering agent to amine-functional compound is between 0.7:1 and 3:14. Process of wherein the ethanolamine-functional compound and the carbon oxide delivering agent are at least partly added as one compound by using a carbamate adduct.5. Process of wherein the amine-functional compound and the carbon oxide delivering agent are at least partly added as one compound by using an urea adduct.6. Process of wherein the ethanolamine-functional compound is of the formula OH—(CH—NH—)H wherein q is at least 1 and the amine-functional compound is of the formula NH—(CH—NH—)H wherein r is at least 1 claim 1 , wherein the sum of q+r is at least 3 and wherein optionally one or more q or r units may be present as a cyclic ethylene urea claim 1 , or cyclic ethylene carbamate unit.7. Process of wherein next a step is performed to convert the obtained cyclic ethylene urea into its corresponding ethylene amine.8. Process of wherein the ethanolamine-functional compound is AEEA ( ...

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Номер записи: 26
05-02-2015 дата публикации

METHOD FOR SYNTHESIZING RAMALIN AND RAMALIN PRECURSOR BY USING GLUTAMIC ACID DERIVATIVE AND HYDROXY ANILINE OR HYDROXY ANILINE HAVING PROTECTED HYDROXY GROUP

Номер: US20150038733A1
Автор: Bhattarai Hari Datta, Han Se Jong, KIM DOCKYU, Kim Il Chan, Kim Keun Sik, Kim Tai Kyoung, Lee Hyoung Seok, Yim Joung Han
Принадлежит: Korea Institute of Ocean Science and Technology

Disclosed is a method of the synthesis of ramalin. It comprises reacting a glutamic acid derivative, which is prepared using alkylchloroformate, with a hydrazine salt compound, which is prepared from hydroxy aniline, whether protected or not. The synthesis method allows ramalin, excellent in antioxidant and anti-inflammatory activity, to be simply synthesized at stable yield even without use of a highly toxic solvent such as DMF. In addition, the method is cost competitive, and provides ramalin at high efficiency, thus enabling the mass production of ramalin. 3. The method of claim 2 , wherein the glutamic acid derivative represented by Chemical Formula 5 is prepared by protecting an amino acid group of the glutamic acid with a carbobenzyloxy group claim 2 , and esterifying an alpha carboxyl group with a benzyl group.4. The method of claim 1 , wherein the hydrazine salt compound represented by Chemical Formula 3 is prepared by reducing azo compound from 2-hydroxy aniline or an acid salt of protected hydroxy aniline5. The method of claim 1 , wherein Ris selected from the group consisting of methyl claim 1 , ethyl claim 1 , propyl claim 1 , isopropyl claim 1 , butyl claim 1 , isobutyl claim 1 , pentyl claim 1 , hexyl claim 1 , heptyl claim 1 , octyl claim 1 , 2-ethylhexyl claim 1 , substituted alkyl claim 1 , and cycloalkyl.6. The method of claim 1 , wherein Ris ethyl.7. The method of claim 1 , wherein Ris hydrogen.8. The method of claim 1 , wherein Ris a benzyl group for protecting hydroxy.9. The method of claim 1 , wherein the acid is hydrochloric acid claim 1 , bromic acid claim 1 , iodic acid claim 1 , or P-toluenesulfonic acid. The present invention relates to a method of the synthesis of ramalin. More particularly, the present invention relates to a method of synthesizing ramalin by reacting a glutamic acid derivative which is prepared using alkylchloroformate, with hydroxy aniline, or protected hydroxy aniline.A lichen, resembling a non-flowering plant, is a ...

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Номер записи: 27
03-03-2022 дата публикации

HIGH PRESSURE STRIPPERS FOR USE IN UREA PLANTS

Номер: US20220064109A1
Автор: PORRO Lino Giovanni
Принадлежит:

Shell-and-tube strippers for stripping a urea/carbamate mixture, related systems, methods, and uses. The stripper includes a shell, a plurality of tubes disposed within the shell, and a heating fluid distributor for homogenizing the flow of a heating fluid near a heating fluid inlet. The heating fluid distributor includes an edge wall and a laterally disposed heating fluid distribution plate. Related systems, methods, and uses are also provided.

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Номер записи: 28
23-02-2017 дата публикации

METHOD USING TITANIUM CATALYST FOR PRODUCING CARBAMATE-FUNCTIONAL MATERIALS

Номер: US20170051092A1
Автор: JADHAV Abhijit
Принадлежит: BASF COATINGS GMBH

A carbamate-functional material is prepared by reacting a carbamate compound with a hydroxy-functional material using titanium (IV) alkoxide as catalyst. 1. A method of preparing a carbamate-functional material , the method comprising:reacting a carbamate compound with a hydroxy-functional material in the presence of a titanium (IV) alkoxide catalyst to form a carbamate-functional material.2. The method according to claim 1 , wherein the titanium (IV) alkoxide catalyst comprisesn alkoxide groups, and4−n groups selected from the group consisting of halogen groups, acetylacetonate groups, ethanolaminato groups, and mixtures thereof,wherein n is an integer from one to four.3. The method according to claim 2 , wherein the n alkoxide groups comprise one to eight carbon atoms.4. The method according to claim 1 , wherein the titanium (IV) alkoxide catalyst comprises titanium (IV) isopropoxide.5. The method according to claim 1 , wherein the carbamate compound is an alkyl carbamate.6. The method according to claim 5 , wherein the carbamate compound is at least one selected from the group consisting of methyl carbamate claim 5 , ethyl carbamate claim 5 , n-propyl carbamate claim 5 , isopropyl carbamate claim 5 , n-butyl carbamate claim 5 , isobutyl carbamate claim 5 , tert-butyl carbamate claim 5 , n-hexyl carbamate claim 5 , 2-ethylhexyl carbamate claim 5 , cyclohexyl carbamate claim 5 , and phenyl carbamate.7. The method according to claim 1 , wherein the hydroxy-functional material is a monomeric compound comprising from 1 to 160 carbon atoms.8. The method according to claim 1 , wherein the hydroxy-functional material comprises from 12 to 72 carbon atoms and at least two hydroxyl groups.9. The method according to claim 1 , wherein the hydroxy-functional material is obtained by a reduction of an addition product of unsaturated fatty acids.10. The method according to claim 1 , wherein the hydroxy-functional material is a hyperbranched polyol.11. The method according to ...

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Номер записи: 29
02-03-2017 дата публикации

PROCESS FOR MAKING LYSINE-GLUTAMIC ACID DIPEPTIDE DERIVATIVES

Номер: US20170057912A1
Автор: Puentener Kurt
Принадлежит: Hoffmann-La Roche Inc.

The invention relates to compounds of the formula 2. The process of claim 1 , wherein the ester protecting group is selected from C-alkyl claim 1 , optionally substituted with phenyl claim 1 , C-alkenyl claim 1 , piperidinyl or dimethylaminoboranyl.3. The process of claim 1 , wherein Ris hydrogen or C-alkyl.4. The process of claim 1 , wherein Ris C-alkyl.5. The process of claim 1 , wherein Ris hydrogen.6. The process of claim 1 , wherein Ris 9H-fluoren-9-ylmethoxycarbonyl7. The process of claim 1 , wherein Ris t-butyl.8. The process of claim 1 , wherein Ris C-alkyl.9. The process of claim 1 , wherein Ris C-alkyl.10. The process of claim 1 , wherein Ris pentadecyl.11. The process of claim 1 , wherein Ris 9H-fluoren-9-ylmethoxycarbonyl and Ris C-alkyl.12. The process of claim 1 , wherein Ris 9H-fluoren-9-ylmethoxycarbonyl and Ris pentadecyl.15. The process of claim 1 , wherein the coupling of the glutamic acid derivative of formula II with the lysine derivative of formula III is carried out by solid phase synthesis.16. The process of claim 1 , wherein the coupling of the glutamic acid derivative of formula II with the lysine derivative of formula III is carried out by FMOC solid phase synthesis. This application is a divisional of U.S. application Ser. No. 14/539,126 filed on Nov. 12, 2014, which is a continuation of PCT/EP2013/059759 filed on May 13, 2013, which claims priority to EP Patent Application No. 12168119.1 filed on May 15, 2012, the disclosures of which are all incorporated herein by reference in their entiretyThe invention relates to compounds of the formulawherein,Rand Rare the same or different and denote hydrogen or an ester protecting group,Ris hydrogen or an amino protecting group andRis C-alkyl,and its enantiomers, diastereomers and salts.The invention in a further embodiment relates to a process for the preparation of the compounds of the formula I and to the use of the compounds of formula I in the solid phase peptide synthesis.The compounds of ...

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Номер записи: 30
04-03-2021 дата публикации

PROCESS FOR THE SYNTHESIS OF OPTICALLY ACTIVE BETA-AMINO ALCOHOLS

Номер: US20210061757A1
Автор: Bertolini Giorgio, BERTUOLO Stefania, Colli Corrado, Di Fabio Romano, GARIS Faris, MAIORANA Stefano, NISIC Filippo, RONZONI Silvano, SADA Mara
Принадлежит:

Subject-matter of the present invention is a process for the preparation of optically active phenyl-beta-amino alcohols by means of a specific reduction of the corresponding phenyl-beta-amino ketones. Further subject-matter of the invention are said novel synthesis intermediates and their use for the preparation of active pharmaceutical ingredients. 2. The process according to claim 1 , wherein said protecting groups may be removed by hydrogenation or alkaline hydrolysis.3. The process according to claim 2 , wherein said protecting groups are selected from benzyl and carbobenzyloxy.4. The process according to claim 2 , wherein said protecting groups are removed by hydrogenation with a maximum hydrogen pressure of 3.0±0.2 bar claim 2 , in the presence of a carboxylic acid which has at least one chiral center and is in enantiomerically pure form.5. The process according to wherein said acid is selected from D-tartaric acid claim 4 , L-tartaric acid claim 4 , D-benzoyltartaric acid claim 4 , L-benzoyltartaric acid claim 4 , D-camphor-10-sulfonic acid claim 4 , L-camphor-10-sulfonic acid claim 4 , D-mandelic acid claim 4 , L-mandelic acid.6. The process according to claim 1 , wherein Rand Rare the same; and/or Rand Rdo not both represent hydrogen; and/or Rand Rare the same and each represents a benzyl group.78-. (canceled)9. The process according to claim 1 , wherein Rrepresents a carbobenzyloxy group.10. The process according to claim 1 , wherein Rand Rare the same and each represents a benzyl group and Rrepresents a carbobenzyloxy group.11. The process according to claim 1 , wherein R claim 1 , Rand Rare the same and each represents a carbobenzyloxy group.12. The process according to claim 1 , wherein Ris a carbobenzyloxy group and Ris hydrogen.13. The process according to claim 1 , wherein said alkyl group is selected from methyl and isopropyl.14. The process according to claim 1 , wherein R claim 1 , Rand Rare the same and each represents a carbobenzyloxy group and ...

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Номер записи: 31
27-02-2020 дата публикации

ZINC-IMIDAZOLE COMPLEX MIXED CATALYST AND METHOD FOR PRODUCING METHYL N-PHENYL CARBAMATE USING THE SAME

Номер: US20200061596A1
Автор: Cho Shinhye, Dahnum Deliana, JAE Jungho, KIM Hong Gon, Lee Hyun Joo
Принадлежит: KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY

Disclosed is a zinc-imidazole complex mixed catalyst. Also disclosed are a method for preparing the zinc-imidazole complex mixed catalyst and a method for producing a methyl N-phenyl carbamate in high yield with high selectivity in the presence of the catalyst. The zinc-imidazole complex mixed catalyst can be reused due to its high reaction stability. In addition, the use of the zinc-imidazole complex mixed catalyst leads to a marked improvement in the production yield of a methyl N-phenyl carbamate with high selectivity. 2: The method according to claim 1 , wherein claim 1 , in step (a) claim 1 , the zinc precursor is mixed with [the [an]]imidazole precursor in a first solvent and the reaction mixture is reactgd at a temperature of 100 to 150° C. for 12 to 48 hours.3: The method according to claim 2 , wherein the zinc precursor is a zinc salt and the zinc salt is zinc acetate.4: The method according to claim 3 , wherein the imidazole precursor is selected from the group consisting of imidazole claim 3 , 2-chloromethylimidazole claim 3 , imidazole-2-carboxylic acid claim 3 , 2-phenylimidazole claim 3 , benzimidazole claim 3 , 2-methylimidazole claim 3 , and mixtures thereof.5: The method according to claim 4 , wherein the zinc precursor is reacted with the imidazole precursor in a molar ratio of zinc precursor:imidazole precursor of 1:1 to 1:4.6: The method according to claim 5 , wherein claim 5 , in step (b) claim 5 , the reaction mixture is precipitated in a second solvent and the precipitate is collected and dried at a temperature of 180 to 200° C. for 1 to 5 hours.7: The method according to claim 6 , wherein the first solvent and the second solvent are the same as or different from each other and are each independently selected from the group consisting of N claim 6 ,N-dimethylformamide claim 6 , N claim 6 ,N-dimethylacetamide claim 6 , N-methyl-2-pyrrolidone claim 6 , N-ethyl-2-pyrrolidone claim 6 , vinylpyrrolidone claim 6 , 1 claim 6 ,3-dimethyl-2- ...

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Номер записи: 32
27-02-2020 дата публикации

PROCESSES FOR THE PREPARATION OF PYRIMIDINYLCYCLOPENTANE COMPOUNDS

Номер: US20200062717A1
Автор: Gosselin Francis, Iding Hans, Reents Reinhard, Scalone Michelangelo
Принадлежит: Genentech, Inc.

The present invention relates to a process for the preparation of a compound of formula (I) 2. The process according to claim 1 , wherein the oxidoreductase catalyzes the asymmetric reduction of a compound of formula (V) to a compound of formula (III) with a diastereoselectivity of at least 95% diastereomeric excess (de).3. The process according to claim 1 , wherein the oxidoreductase catalyzes the asymmetric reduction of a compound of formula (V) to a compound of formula (III) with a diastereoselectivity of at least at least 98% de.4. The process according to claim 1 , wherein the asymmetric reduction of a compound of formula (V) to a compound of formula (III) is catalyzed by an oxidoreductase in the presence of a cofactor.5. The process according to claim 4 , the cofactor which is oxidized in the asymmetric reduction of a compound of formula (V) to a compound of formula (III) is NADH or NADPH.6. The process according to claim 4 , wherein the cofactor is in situ regenerated by enzyme-coupled cofactor regeneration using glucose and glucose dehydrogenase as cosubstrate.7. The process according to claim 4 , wherein the cofactor is in situ regenerated by substrate coupled regeneration using a secondary alcohol as cosubstrate.8. The process according to claim 7 , wherein the secondary alcohol as cosubstrate for the substrate coupled regeneration is selected from the group consisting of 2-propanol claim 7 , 2-butanol claim 7 , 2-pentanol claim 7 , pentan-1 claim 7 ,4-diol claim 7 , 4-methyl-2-pentanol claim 7 , 2-hexanol claim 7 , hexan-1 claim 7 ,5-diol claim 7 , 2-heptanol claim 7 , and 2-octanol.9. The process according to claim 7 , wherein the secondary alcohol as cosubstrate for the substrate-coupled cofactor regeneration is 2-propanol.10. The process according to claim 1 , wherein the oxidoreductase is a diastereoselective NADPH-dependent oxidoreductase selected from the group consisting of KRED-NADPH-111 claim 1 , KRED-NADPH-112 claim 1 , KRED-NADPH-113 claim 1 , ...

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Номер записи: 33
08-03-2018 дата публикации

Manufacture of 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3-ol

Номер: US20180065984A1
Автор: DE FAVERI Carla, Huber Florian Anton Martin
Принадлежит: H. Lundbeck A/S

The present invention relates to a process for synthesis of 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3-ol abbreviated THIP, having the INN name gaboxadol, starting from pyrrolidin-2-one. The process comprises a new direct process to obtain the intermediate dimethyl 5-hydroxy-3,6-dihydropyridine-1,4(2H)-5 dicarboxylate or the intermediate diethyl 5-hydroxy-3,6-dihydropyridine-1,4(2H)-dicarboxylate. 127-. (canceled)29. The process according to claim 28 , wherein step (e) is carried out in toluene.30. The process according to claim 28 , wherein the reaction in step (e) is carried out at either a reflux temperature or at a temperature between 70° C. and 85° C.33. The process according to claim 31 , wherein the steps (b) claim 31 , (c) and (d) are carried out in toluene.34. The process according to claim 31 , wherein the base used in step (b) is triethylamine.35. The process according to claim 31 , wherein the compound of formula V is purified by washing with acidified water or by distillation or by a combination of these two purification strategies.36. The process according to claim 31 , wherein the compound of formula V is purified by thin-film distillation.39. The process according to claim 38 , wherein the compound of formula IIb is obtained by a one-pot synthesis. The present invention relates to a process for synthesis of 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3-ol abbreviated THIP, having the INN name gaboxadol, starting from pyrrolidin-2-one. The process comprises a new direct process to obtain the intermediate dimethyl 5-hydroxy-3,6-dihydropyridine-1,4(2H)-dicarboxylate or the intermediate diethyl 5-hydroxy-3,6-dihydropyridine-1,4(2H)-dicarboxylate.The compound 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3-ol abbreviated THIP, having the INN name gaboxadol, was disclosed for the first time in EP Patent No. 0000338 and has the molecular structure depicted below.Gaboxadol is a GABAA receptor agonist with functional selectivity for the delta containing GABAA ...

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Номер записи: 34
12-03-2015 дата публикации

LYSINE-GLUTAMIC ACID DIPEPTIDE DERIVATIVES

Номер: US20150073173A1
Автор: Puentener Kurt
Принадлежит: Hoffmann-La Roche Inc.

The invention relates to compounds of the formula 2. The compound of wherein claim 1 , the ester protecting group is selected from C-alkyl claim 1 , optionally substituted with phenyl claim 1 , C-alkenyl claim 1 , piperidinyl or dimethylaminoboranyl.3. The compound of claim 1 , wherein Ris hydrogen or C-alkyl and Ris hydrogen or C-alkenyl.4. The compound of claim 1 , wherein Ris t-butyl and Ris hydrogen or allyl.5. The compound of claim 1 , wherein Ris 9H-fluoren-9-ylmethoxycarbonyl.6. The compound of claim 1 , wherein Ris C-alkyl.7. (canceled)9. The compound of claim 7 , wherein claim 7 ,{'sup': 1', '2', '3', '4, 'sub': '15', 'Ris t-butyl, Ris hydrogen, Ris 9H-fluoren-9-ylmethoxycarbonyl and Ris C-alkyl;'}{'sup': 1', '2', '3', '4, 'sub': '15', 'Ris t-butyl and Ris allyl, Ris 9H-fluoren-9-ylmethoxycarbonyl and Ris C-alkyl.'}10. The compound of claim 9 , wherein claim 9 ,{'sup': 1', '2', '3', '4, 'Ris t-butyl and Ris hydrogen, Ris 9H-fluoren-9-ylmethoxycarbonyl and Ris pentadecyl;'}{'sup': 1', '2', '3', '4, 'Ris t-butyl and Ris allyl, Ris 9H-fluoren-9-ylmethoxycarbonyl and Ris pentadecyl.'}12. (canceled)13. (canceled) The invention relates to compounds of the formulawherein,Rand Rare the same or different and denote hydrogen or an ester protecting group,Ris hydrogen or an amino protecting group andRis C-alkyl,and its enantiomers, diastereomers and salts.The invention in a further embodiment relates to a process for the preparation of the compounds of the formula I and to the use of the compounds of formula I in the solid phase peptide synthesis.The compounds of the present invention have been found to be versatile peptide intermediates for the solid phase peptide synthesis (SPPS) of peptide drugs which comprise a Glu-fatty alkyl side chain building block attached to a Lys-part of the peptide chain. For example Liraglutide can be mentioned, which is a GLP-1 analog diabetes-2 peptide drug. Liraglutide carries a Glu-hexadecanoyl side chain building block at the ...

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Номер записи: 35
24-03-2022 дата публикации

Synthesis Method for Candesartan Cilexetil Intermediate

Номер: US20220089526A1
Автор: Huang Jiansheng, LIANG Zunjun, Tu Guoliang, Yang Tao, Zhang Lu
Принадлежит:

A synthesis method for a candesartan cilexetil intermediate represented by formula (II) is provided. The method includes (1) dissolving a compound represented by formula (IV) to an aprotic solvent to obtain a first mixed solution, and dissolving a phase transfer catalyst and an azidation reagent to water to obtain a second mixed solution; (2) dropping the first mixed solution to the second mixed solution for azidation reaction, and after the reaction is ended, standing and layering same to obtain an organic phase containing a compound represented by formula (V); (3) dropping the obtained organic phase containing the compound represented by formula (V) to tertiary butyl alcohol for rearrangement reaction, and after the reaction is ended, concentrating same to obtain a solid or oily material, then adding a crystallizing solvent to the obtained solid or oily material for recrystallization, and separating same to obtain a crystal. 2. The method according to claim 1 , wherein the aprotic solvent is selected from the group consisting of toluene claim 1 , chlorobenzene claim 1 , xylene claim 1 , chloroform claim 1 , 1 claim 1 ,2-dichloroethane and 1 claim 1 ,2-dibromoethane claim 1 , or any combination thereof.3. The method according to claim 1 , wherein the phase transfer catalyst is selected from the group consisting of tetrabutylammonium bromide claim 1 , tetrabutylammonium chloride claim 1 , tetrabutylammonium hydrogen sulfate claim 1 , tetrabutylammonium fluoride and tetrabutylammonium iodide claim 1 , or any combination thereof.4. The method according to claim 1 , wherein a molar ratio of the phase transfer catalyst to the compound represented by formula (IV) is 0.01-0.08:1.5. The method according to claim 1 , wherein the azidation reaction is carried out at −3° C. to 10° C.6. The method according to claim 1 , wherein the rearrangement reaction is carried out at 75° C. to 95° C.7. The method according to claim 1 , wherein a molar ratio of tertiary butyl alcohol to ...

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Номер записи: 36
05-06-2014 дата публикации

NOVEL [F-18]-LABELLED L-GLUTAMIC ACID AND L-GLUTAMINE DERIVATIVES (I), THEIR USE AND PROCESSES FOR THEIR PREPARATION

Номер: US20140154183A1
Автор: BERNDT Matthias, DINKELBORG Ludger, FRIEBE Matthias, Graham Keith, Koglin Norman, Schmitt-Willich Heribert
Принадлежит:

What is described are the compounds and the synthesis of [F-18]-labelled L-glutamic acid, [F-18]-labelled L-glutamate, their derivatives of the formula (I) and their use. 2) Compounds according to claim 1 , characterized in that Ris selected from the group consisting of F-methoxy claim 1 , F-ethoxy claim 1 , F-propoxy claim 1 , F-ethyl and F-propyl claim 1 , and Ris hydrogen.5) Compounds according to claim 4 , characterized in that Ris selected from the group consisting of F-ethoxy claim 4 , F-propoxy claim 4 , F-ethyl claim 4 , and F-propyl claim 4 , and Ris hydrogen.7) Process for preparing compounds of the general formula (I) according to claim 1 , said process comprising:{'claim-ref': [{'@idref': 'CLM-00004', 'claims 4'}, {'@idref': 'CLM-00006', '6'}], 'removing one or more protective groups present in a compound of the formula (II) according to any of to .'}8) Process for preparing compounds of the general formula (II) according to claim 4 , said process comprising:{'claim-ref': {'@idref': 'CLM-00012', 'claim 12'}, 'reacting a compound of the formula (III) according to with F-18 fluoride.'}9) Compounds according to for use as medicaments.10) Compounds according to for use for imaging in tumour disorders.11) A method of imaging a patient for tumor disorders comprising imaging a patient who has been administered a compound according to .14) Imaging kit claim 1 , comprising compounds of the general formula III or IV.15) Pharmaceutical composition claim 1 , comprising compounds of the general formula I claim 1 , II claim 1 , III or IV and suitable pharmaceutical carrier substances.16) Compounds according to claim 1 , and compounds of the general formula IV claim 1 , characterized in that the compounds are suitable for imaging in a dosage range of 37-600 MBq.17) Compounds according to claim 16 , characterized in that the compounds are particularly suitable in a dosage range of 150 MBq-370 MBq. The invention relates to the subject matter referred to in the claims, i. ...

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Номер записи: 37
14-03-2019 дата публикации

MICRO/NANO MATERIALS, PRODUCTS OBTAINED BY COVALENTLY MODIFYING SURFACE OF MICRO/NANO MATERIALS WITH HYDROPHILIC MATERIALS, AND METHOD FOR MAKING SAME

Номер: US20190077746A1
Автор: Feng Hu, LIAO Fei, LONG Gaobo, Yang Hai
Принадлежит:

Micro-nano materials, products obtained by covalently modifying the surfaces of micro/nano materials with hydrophilic materials, and methods for making the same. The micro/nano materials on the surfaces have carboxyl groups or/and pro-carboxyl groups which are converted into their active esters. The products are covalently modified by forming amide bonds between the active esters on the surfaces and the modification agents; where the modification agents are hydrophilic compounds and/or hydrophilic polymers bearing primary and/or secondary aliphatic amines. Monomers bearing carboxyl groups and/or pro-carboxyl groups are used to produce an adequate number of carboxyl groups and/or pro-carboxyl groups on the surface of a polymer material to be modified. The carboxyl groups and/or pro-carboxyl groups are converted into active esters. A reasonably-sized modification agent bearing primary and/or secondary amines, zwitterions and hydrophilic linear spacer arms is used to form amide bonds and obtain a covalently modified surface layer. 1. A method for preparing a product obtained by covalently modifying the surface of a micro/nano material with a hydrophilic material , wherein the micro/nano material to be modified on the surface comprises a functional group selected from one or more of a carboxyl group , a pro-carboxyl group , an active ester , a cation , an anion , a neutral hydrophilic group , a metal ion chelating group or a protein-disulfide-selective modification group; wherein the functional group on the surface of the micro/nano material to be modified is derived from organic monomers used in making the micro/nano material through polymerization reaction , or produced through derivatization of the carboxyl group and/or the pro-carboxyl group of the organic monomers used in the polymerization reaction;wherein the covalently-modified product comprises a product of mono-layer covalent modification and a product bearing multilayer covalent modification;the carboxyl ...

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Номер записи: 38
22-03-2018 дата публикации

NOVEL CONFIGURATION AND ITS USE IN PROCESS FOR SYNTHESIS OF ALKYL CARBAMATES FROM ALKYL ALCOHOL AND UREA IN A TUBULAR REACTOR

Номер: US20180079714A1
Автор: KELKAR Ashutosh Anant, KINAGE Anil Kisan, MOTE Dhananjay Ravindra, RANADE Vivek Vinayak, RANE Vilas Hari, ROY Lalita Sanjib, SHINGOTE Savita Kiran
Принадлежит:

The present invention discloses an improved catalyst free process for synthesis of alkyl carbamates in an integrated system comprising a tubular reactor and a striper. The process comprises reacting urea and an alcohol in said tubular reactor under autogeneous pressure; wherein said process provides >90% selectivity towards alkyl carbamate. The mixture of urea and alcohol is N fed to the tubular reactor at a particular feed rate. The tubular reactor is heated externally under autogeneous pressure to carry out a synthesis reaction producing alkyl carbamate and ammonia. The ammonia is removed from the tubular reactor by the striper. The tubular reactor and the stripper are arranged in series to reduce the equilibrium limitations of the reaction and drive the reaction in forward direction. 1. A catalyst free process for synthesis of alkyl carbamate within an integrated system of at least one tubular reactor and a stripper in series , comprising reacting urea and an alcohol in said tubular reactor under autogeneous pressure; wherein said process provides >90% selectivity towards alkyl carbamate.2. The catalyst free process according to claim 1 , wherein the alcohol is selected from methanol claim 1 , ethanol claim 1 , 1-propanol claim 1 , 2-propanol claim 1 , 1-butanol claim 1 , 2-butanol claim 1 , tert-butanol claim 1 , pentanol and its isomers claim 1 , hexanol and its isomers claim 1 , their higher homologues or their isomers.3. The catalyst free process according to claim 1 , wherein the temperature of the reaction mixture is in the range of 150-250 C.4. The catalyst free process according to claim 1 , wherein urea and alcohol in mole ratio 10 to 50 are fed in to the tubular reactor at a feed rate of 5-25 ml/min.5. The catalyst free process according to claim 1 , wherein said process can be carried out continuously claim 1 , semi continuously or batch wise.6. The catalyst free process according to claim 1 , wherein the process further comprises reacting said alkyl ...

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Номер записи: 39
26-03-2015 дата публикации

NITROGEN-CONTAINING INORGANIC CARRIER MATERIALS

Номер: US20150087700A1
Автор: Böttcher Andreas, Uhr Hermann
Принадлежит:

The invention relates to nitrogen-containing inorganic carrier materials, more particularly to inorganic carrier materials containing organically bonded nitrogen, to their preparation and also to their use for stabilizing iodine-containing compounds, and also to binder formulations comprising them and to the use thereof for protecting industrial materials. 1. A processes for stabilizing iodine-containing compounds , the process comprising adding a nitrogen-containing inorganic carrier material to an iodine-containing compound , wherein the nitrogen-containing inorganic carrier material comprises an inorganic carrier material comprising at least one adsorptively or covalently bonded nitrogen-containing compound.2. The process according to claim 1 , wherein the nitrogen-containing compound is selected from the following: {'br': None, 'sup': 1', '2', '3, 'RRRN\u2003\u2003(Ia)'}, 'A) compounds of the formula (Ia)'}in which{'sup': 1', '2', '3, 'R, Rand Reach independently of one another are hydrogen, alkyl, alkenyl or aryl or in pairs together form a 3- to 7-membered N-heterocyclic, aliphatic, unsaturated or aromatic ring,'}the radicals alkyl, alkenyl or aryl or the 3- to 7-membered N-heterocyclic, aliphatic, unsaturated or aromatic ring being either unsubstituted or substituted one or more times by radicals selected from the group consisting of hydroxyl, fluoro, chloro, bromo, iodo, carboxyl, alkylsulphonyl, arylsulphonyl, nitrile and isonitrile,{'sup': 1', '2', '3, 'but at least one of the radicals R, Rand Ris not hydrogen'}B) polyamines, andC) aziridines.3. The process according to claim 2 , wherein the nitrogen-containing inorganic carrier material has a nitrogen content of 0.01% to 10% by weight.4. The process according to claim 3 , wherein the inorganic carrier material is selected from the group consisting of silica claim 3 , fumed silicas claim 3 , diatomite claim 3 , porosils claim 3 , clathrasils claim 3 , dealuminated zeolites claim 3 , aluminosilicates claim ...

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Номер записи: 40
12-06-2014 дата публикации

PROCESS FOR THE PREPARATION OF AN ANTICONVULSANT COMPOUND

Номер: US20140163252A1
Автор: ARTICO Marco, Attolino Emanuele, ROSSI Roberto
Принадлежит: DIPHARMA FRANCIS S.r.I

The invention provides a novel method for the preparation of intermediates useful in a process designed to obtain known 1,2,4-triaminobenzene compounds, and in particular a specific compound thereof having known anticonvulsant activity. Unlike known methods, the novel method does not require advance protection of the amino groups present on the substrate. 3) A process according to wherein in a compound of formula (II) claim 1 , (III) or (IIIa) the substituent R is ethyl.4) A process according to claim 1 , wherein the nitrating reaction is carried out by using a nitrating agent claim 1 , typically nitric acid having a concentration from about 30% w/w to about 100% w/w.5) Process according to wherein nitric acid has a concentration of about 65% w/w.6) A process according to wherein the nitrating reaction is carried out in the presence of a solvent.7) A process according to claim 6 , wherein the solvent is a polar aprotic solvent claim 6 , a chlorinated solvent claim 6 , a polar protic solvent claim 6 , typically an aqueous organic or a mineral acid.8) A process according to wherein the mineral acid is acetic acid or concentrated sulfuric acid.9) A process according to wherein the mineral acid is sulfuric acid having a concentration of about 95% w/w.10) A process according to claim 1 , wherein the nitrating reaction is carried out at a temperature ranging from about −10° C. and the solvent reflux temperature claim 1 , preferably between about 0° C. and 25° C.12) A process according to wherein in a compound of formula (II) or a salt thereof R is ethyl and Ris H.15) A process according to wherein in a compound of formula (VI) R is ethyl. The present invention relates to a process for the preparation of intermediates of known 1,2,4-triaminobenzene compounds with anticonvulsant activity, and in particular of a specific compound.The compound ethyl N-[2-amino-4-[(4-fluorophenyl)methylamino] phenyl]carbamate of formula (I), also known as retigabine, is a voltage-dependent ...

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Номер записи: 41
29-03-2018 дата публикации

PROCESSES FOR THE PREPARATION OF PYRIMIDINYLCYCLOPENTANE COMPOUNDS

Номер: US20180086722A1
Автор: Gosselin Francis, Iding Hans, Reents Reinhard, Scalone Michelangelo
Принадлежит: Genentech, Inc.

The present invention relates to a process for the preparation of a compound of formula (I) 2. The compound of claim 1 , wherein M is an alkali metal ion.3. The compound of claim 1 , wherein M is Li claim 1 , K or Na.4. The compound of claim 1 , wherein M is Na.5. The compound of claim 1 , wherein Ris tert-butoxycarbonyl (BOC).6. The compound of that is sodium (S)-3-(tert-butoxycarbonyl(isopropyl)amino)-2-(4-chlorophenyl)propanoate.8. The process according to claim 7 , wherein metal complex catalyst (C) is a ruthenium complex catalyst.9. The process according to claim 7 , wherein the metal complex catalyst (C) is a ruthenium complex catalyst selected from a compound of formula (C1) claim 7 , (C2) or (C3):{'br': None, 'sub': '2', 'Ru(Z)D\u2003\u2003(C1)'}{'br': None, 'sub': 2-p', 'm', 'p, '[Ru(Z)(D)(L)](Y)\u2003\u2003(C2)'}{'br': None, 'Ru(E)(E′)(D)(F)\u2003\u2003(C3)'}wherein:D is a chiral phosphine ligand;{'sub': '2-7', 'L is a neutral ligand selected from Calkene, cyclooctene, 1,3-hexadiene, norbornadiene, 1,5-cyclooctadiene, benzene, hexamethylbenzene, 1,3,5-trimethylbenzene, p-cymene, tetrahydrofuran, dimethylformamide, acetonitrile, benzonitrile, acetone, toluene and methanol;'}{'sup': 5', '5', '−, 'Z is an anionic ligand selected from hydride, fluoride, chloride, bromide, η-2,4-pentadienyl, η-2,4-dimethyl-pentadienyl or the group A-COO,'}with the proviso that when two Z are attached to the Ru atom they can either be the same or different;{'sub': 1-7', '1-7, 'A is Calkyl, Chaloalkyl, aryl, or haloaryl;'}{'sub': 4', '4', '6', '6', '4', '4', '3', '3', '6', '5', '3, 'sup': −', '−', '−', '−', '−', '−', '−', '−, 'Y is a non-coordinating anion selected from fluoride, chloride, bromide, BF, ClO, SbF, PF, B(phenyl), B(3,5-di-trifluoromethyl-phenyl), CFSO, and CHSO;'}F is an optionally chiral diamine;{'sub': '4', 'sup': '−', 'E and E′ are both halogen ions, or E is hydride and E′ is BH;'}m is 1, 2, 3 or 4; andp is 1 or 2.10. The process according to claim 7 , wherein ...

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Номер записи: 42
09-04-2015 дата публикации

PREPARATION METHOD FOR SOLID POWDER OF A CARBAMIC ACID DERIVATIVE

Номер: US20150099886A1
Автор: HUR Nam Hwi, LEE Byeong No
Принадлежит:

The present application relates to a preparation method for solid powder of a carbamic acid derivative, which includes reacting an amine derivative with carbon dioxide at a temperature in a range of from about −30° C. to about 500° C. and at a pressure in a range of from about 0.3 MPa to about 100 MPa. In addition, the present disclosure relates to a reduction method for solid powder of a carbamic acid derivative to an amine derivative and carbon dioxide, which includes dissolving solid powder of the carbamic acid derivative prepared in a solvent; refluxing the carbamic acid derivative at a temperature in a range of from about 30° C. to about 100° C.; and evaporating the solvent. 1. A preparation method for solid powder of a carbamic acid derivative , the method comprising:reacting an amine derivative with carbon dioxide at a temperature in a range of from about −30° C. to about 500° C. and at a pressure in a range of from about 0.3 MPa to about 100 MPa.4. The preparation method of claim 1 ,wherein the temperature is in a range of from about 0° C. to about 300° C.5. The preparation method of claim 1 ,wherein the pressure is in a range of from about 1 MPa to about 50 MPa.6. The preparation method of claim 1 , the method includingreacting a mixed solution of the amine derivative and one or more selected from the group consisting of ethers, alcohols, aliphatic hydrocarbons, carbocycles, heterocycles, aromatics, and substituted heteroaromatic cycles, with the carbon dioxide.7. The preparation method of claim 6 ,wherein a content of the amine derivative in the mixed solution is from about 1 wt % to about 99 wt %.8. The preparation method of claim 1 , further comprising:after the reaction with the carbon dioxide, reducing the pressure to be in a range of from about 0.01 MPa to about 0.1 MPa so as to evaporate excess carbon dioxide.9. The preparation method of claim 1 , further comprising:{'sub': 1', '12, 'washing the prepared solid powder of the carbamic acid derivative ...

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Номер записи: 43
26-03-2020 дата публикации

SYNTHESIS OF NOVEL INTERMEDIATE(S) FOR PREPARING RIVASTIGMINE

Номер: US20200095195A1
Автор: Bhavsar Chetan Umeshbhai, Eppa Gyanchander, Khamar Bakulesh Mafatlal, Modi Rajiv Indravadan, Vachharajani Pranav Rameshbhai, Vekariya Nutan Bharatbhai, YADAV Jhillu Singh
Принадлежит: Cadila Pharmaceuticals, Ltd.

The present invention relates to novel intermediate(s), which are useful for the preparation of Rivastigmine compound of formula (I) and its pharmaceutically acceptable salts. The present invention further relates to the processes for the preparation of such novel intermediate(s) and preparation of Rivastigmine using such novel intermediate(s). 2. The process according to claim 1 , wherein R claim 1 , Rand Rare selected from hydrogen claim 1 , Calkyl claim 1 , Caryl and Calkylaryl which are substituted with one or more methyl or methoxy.3. The process according to claim 1 , wherein the chiral resolving agent of formula (VI) is selected from 1-phenylethylamine claim 1 , 1-Phenylpropylamine claim 1 , α-Methyl-1-naphthalenemethylamine claim 1 , N-benzyl-1-phenylethylamine claim 1 , N claim 1 ,N-bis[α-methyl benzyl]amine claim 1 , 1-(3-methoxyphenyl)ethylamine claim 1 , 1-(3 claim 1 ,4-dimethoxy-phenyl)ethyl amine claim 1 , α-phenyl-β-(p-tolyl)ethylamine and 1-methyl-3-phenylpropylamine.4. The process according to claim 1 , wherein the chiral resolving agent of formula (VI) is (R)-1-phenylethylamine claim 1 , (R)-(+)-1-Phenylpropylamine and (R)-(+)-α-Methyl-1-naphthalenemethylamine. This application claims the benefit of and priority to the Indian Application Number 201821036203, filed on Sep. 26, 2018, which is incorporated by reference herein in its entirety.The present invention relates to novel intermediate(s) useful for the preparation of Rivastigmine or its pharmaceutically acceptable salts. The present invention further relates to processes for the preparation of the said novel intermediate(s).Rivastigmine which is chemically known as (S)—N-Ethyl-3-[(1-dimethylamino)ethyl]-N-methylphenylcarbamate or Ethylmethylcarbamic acid 3-[(1S)-1-(dimethylamino) ethyl]phenyl ester is represented by a compound of formula (I):Rivastigmine hydrogen tartrate is a reversible cholinesterase inhibitor and is useful in the treatment of Alzheimer's disease.U.S. Pat. No. 4,948,807 ...

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Номер записи: 44
03-07-2014 дата публикации

TELECHELIC MACROMER, METHOD FOR PRODUCING TELECHELIC MACROMER AND COMPOSITION CONTAINING TELECHELIC MACROMER

Номер: US20140187663A1
Автор: EL FRAY Miroslawa, Skrobot Jedrzej
Принадлежит: Zachodniopomorski Uniwersytet Technologiczny w Szczecinie

A telechelic macromer is disclosed having (meth)acrylic end-groups and a core. The macromer defined by Formula 1 comprises a core Y (Formulas 2 to 9) that is linked to (meth)acrylic groups by urethane, ester or anhydride bonds and has iodine value ranging from 5 to 75. The method involves a chemical reaction carried out in solvent, ranging 6-24 hours, wherein the precursor of a core (Formulas 2 and 3) reacts in two stages with compounds forming urethane bonds, or wherein the precursor of a core (Formulas 4 to 8) reacts in one stage with compounds forming ester bonds, or wherein the precursor of a core defined by Formula 9 reacts in one stage with compounds forming anhydride bonds. The urethane, ester and anhydride moieties comprise groups capable of free radical polymerization isolating the final product by evaporation. The composition disclosed provides the macromer, a photoinitiator and possibly a reactive diluent. 1. A telechelic macromer comprising (meth)acrylic end-groups and a core , wherein the macromer defined by Formula 1 comprises a core Y defined by Formulas 2 to 9 which is linked by urethane , ester or anhydride bonds to (meth)acrylic groups , and wherein the iodine value of the telechelic macromer is in the range between 5 and 75.2. A telechelic macromer according to claim 1 , wherein the precursor of the core defined by Formula 2 comprises a branched dimer fatty acid compound of 36 carbon atoms per molecule and comprises primary amine end-groups claim 1 , and said precursor has amine value of 200-210 mg KOH/g.3. A telechelic macromer according to claim 2 , wherein the urethane bonds are formed by reaction of the core precursor with trimethylene carbonate or propylene carbonate and the linking ester bonds are formed by subsequent reactions with (meth)acryloyl chloride.4. A telechelic macromer according to claim 1 , wherein the precursor of the core defined by Formula 3 comprises a branched dimer fatty acid compound of 36 carbon atoms per molecule or it ...

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Номер записи: 45
09-06-2022 дата публикации

Process for preparing {6-[(diethylamino)methyl]naphthalen-2-yl}methyl [4-(hydroxycarbamoyl)phenyl]carbamate having high purity

Номер: US20220177421A1
Автор: BERARDI Giorgio, COCCIOLO Stefania, MAULUCCI Nakia, TURCHETTA Stefano, ULLUCCI Elio, ZENONI Maurizio
Принадлежит:

A process for obtaining {{6-[(diethylamino)methyl]naphthalen-2-yl}methyl [4-(hydroxycarbamoyl)phenyl]carbamate and/or pharmaceutically acceptable salts thereof having high purity is described. This process allows to obtain a product having an amount of any single unknown impurity equal to or less than 0.10%, as well as a product having a purity greater than 99.5%, preferably equal to or greater than 99.6%. 123-. (canceled)25. The process according to claim 24 , wherein the organic solvent is selected from the group consisting of THF claim 24 , methyl-THF claim 24 , dioxane claim 24 , ethylene glycol dimethyl ether claim 24 , and bis(2-methoxyethyl)ether.26. The process according to claim 24 , wherein the organic solvent is used in an amount between 1 and 100 parts by volume per part by weight of the compound of formula (II).27. The process according to claim 24 , wherein the organic solvent has a water content lower than 0.5%.28. The process according to claim 24 , wherein step ii) is carried out at room temperature.29. The process according to claim 24 , which further comprises a step iii) of isolating {6-[(diethylamino)methyl]naphthalen-2-yl}methyl [4-(hydroxycarbamoyl)phenyl]carbamate as a free base or as a pharmaceutically acceptable salt.30. The process according to claim 29 , wherein the {6-((diethylamino)methyl]naphthalen-2-yl}methyl [4-(hydroxycarbamoyl)phenyl]carbamate is isolated as a hydrochloride or hydrochloride monohydrate salt.32. The process according to claim 31 , wherein the aprotic dipolar solvent is selected from the group consisting of DMSO claim 31 , acetonitrile claim 31 , dimethylacetamide claim 31 , anddimethylformamide.33. The process according to claim 31 , wherein the halogenating agent is a chlorinating agent.34. The process according to claim 33 , wherein the chlorinating agent is selected from the group consisting of thionyl chloride (SOCl) claim 33 , phosphorus trichloride (PCl) claim 33 , phosphorus oxychloride (POCl) claim 33 , and ...

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Номер записи: 46
13-05-2021 дата публикации

CRYSTAL FORMS AND METHODS OF SYNTHESIS OF (2R, 6R)-HYDROXYNORKETAMINE AND (2S, 6S)-HYDROXYNORKETAMINE

Номер: US20210139411A1
Автор: Gould Todd, Moaddel Ruin, Morris Patrick, Thomas Craig, Zanos Panos, Zarate Carlos
Принадлежит:

The disclosure provides a method for synthesizing free base forms of (2R,6R)-hydroxynorketamine (HNK) and (2S,6S)-hydroxynorketamine. In an embodiment synthesis of (2R,6R)-hydroxynorketamine (HNK) includes preparation of (R)-norketamine via chiral resolution from racemic norketamine via a chiral resolution with L-pyroglutamic acid. The disclosure also provided crystal forms of the corresponding (2R,6R)-hydroxynorketamine (HNK) and (2S,6S)-hydroxynorketamine hydrochloride salts. 14.-. (canceled)5. A method for the chiral resolution of norketamine , comprising adding (D)-(R)-pyroglutamic acid to racemic norketamine in a solvent , forming solid (S)-norketamine D-pyroglutamate and converting the (S)-norketamine D-pyroglutamate to (S)-norketamine; oradding (L)-(S)-pyroglutamic acid to acemic norketamine in a solvent, forming solid (R)-norketamine L-pyroglutamate, and converting (R)-norketaime L-pyroglutamate to (R)-norketamine.67.-. (canceled)9. The method according to claim 8 , wherein Ris tert-butyl and wherein cleaving the carbamate linkage comprises treatment of the compound of Formula IIa or Formula IIb with acid.10. The method according to claim 9 , wherein the acid is trifluoroacetic acid.11. The method according to claim 8 , additionally comprising treating (2R claim 8 ,6R)-hydroxynorketamine with hydrochloric acid to manufacture (2R claim 8 ,6R)-hydroxynorketamine hydrochloride salt claim 8 , or treating (2S claim 8 ,6S)-hydroxynorketamine with hydrochloric acid to manufacture (2S claim 8 ,6S)-hydroxynorketamine hydrochloride salt.12. (canceled)13. The method according to claim 8 , wherein the base is lithium diisopropylamide claim 8 , sodium hexamethyldisilazane claim 8 , potassium hexamethyldisilazane claim 8 , or sec-butyllithium claim 8 , and the compound of Formula Ia or Formula Ib is treated with the base at a temperature below 0° C.14. The method according to wherein treating the compound of Formula Ia or Formula Ib with a base comprises treating the ...

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Номер записи: 47
16-04-2020 дата публикации

DIFLUOROALKYLCYCLOPROPYL AMINO ACIDS AND ESTERS, AND SYNTHESES THEREOF

Номер: US20200115329A1
Автор: Abrahamson Michael J., Hill David R., Lukin Kirill A., Mei Jianzhang
Принадлежит:

The invention provides methods of synthesizing compounds in an asymmetric or enantioenriched fashion, wherein the compounds are useful intermediates in the synthesis of viral protease inhibitors. 116-. (canceled)18. The method of claim 17 , wherein the first metal comprises TiCl claim 17 , TiOR claim 17 , CeCl claim 17 , Ce(SO) claim 17 , CaCl claim 17 , MgCl claim 17 , Ti(Oi-Pr)Cl or Ti(OEt)Cl.19. The method of claim 17 , wherein the first base is present; and the first base comprises (i-Pr)EtN claim 17 , triethylamine claim 17 , EtNH claim 17 , EtNH claim 17 , or (iPr)NH.20. The method of claim 19 , wherein the first base is triethylamine.21. The method of claim 17 , wherein the first metal is CeClor MgCl; and the first base is absent.22. The method of claim 17 , wherein the first metal is CeClor MgCl; and the first metal is present in a catalytic quantity.23. The method of claim 17 , wherein the first metal is TiCl claim 17 , TiOR claim 17 , Ti(Oi-Pr)Cl claim 17 , or Ti(OEt)Cl; and the first metal is present in a stoichiometric quantity.24. The method of claim 17 , wherein the first solvent comprises MeOH claim 17 , EtOH claim 17 , n-PrOH claim 17 , i-PrOH claim 17 , tetrahydrofuran (THF) claim 17 , methyl tert-butyl ether claim 17 , ethyl acetate claim 17 , dioxane claim 17 , DMF claim 17 , acetonitrile claim 17 , or DMSO.25. The method of claim 24 , wherein the first metal is TiCl claim 24 , TiOR claim 24 , Ti(Oi-Pr)Cl claim 24 , or Ti(OEt)Cl.26. The method of claim 24 , wherein the first metal is CeClor MgCl.27. The method of claim 17 , wherein the first temperature is from about −10° C. to about 15° C.28. The method of claim 17 , wherein the first period of time is from about 6 h to about 18 h.29. The method of claim 17 , further comprising heating the first product mixture at a second temperature.30. The method of claim 29 , wherein the first product mixture is maintained at the second temperature for a second period of time.31. The method of claim 17 , ...

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Номер записи: 48
27-05-2021 дата публикации

Organic amine collection method

Номер: US20210155573A1
Автор: Masaaki Shinohata, Nobuhisa Miyake, Takeharu Sasaki, Yusuke Ishii, Yusuke Sakurai
Принадлежит: Asahi Kasei Corp

A method is provided for collecting a compound of formula (III) (in which R31 is a monovalent to trivalent organic group and n31 is an integer of 1 to 3) from a liquid phase component that is formed as a by-product in a method for producing a compound of general formula (I) (in which R11 is a monovalent to trivalent organic group and n 11 is an integer of 1 to 3), wherein the collection method contains steps (1) to (3) or steps (A) and (B), and step (4). Step (1): a step for reacting the liquid phase component with at least one active hydrogen-containing compound in a reactor. Step (2): a step for returning a condensed liquid obtained by cooling gas phase components in the reactor to the reactor. Step (3): a step for discharging gas phase components that are not condensed in the step (2) to the outside of the reactor. Step (A): a step for mixing the liquid phase component, water, and a compound of general formula (III). Step (B): a step for reacting the liquid phase component with water inside the reactor. Step (4): a step for discharging, as a liquid phase component inside the reactor, the reaction liquid containing the compound of general formula (III) to the outside of the reactor. R 11 NCO) n11   (I) R 31 NH 2 ) n31   (III)

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Номер записи: 49
14-05-2015 дата публикации

Process for Preparing Disubstituted Urea and Carbamate Compounds from Amines, Carbon Dioxide, and Epoxides

Номер: US20150133676A1
Автор: Cho Jin Ku, Kim Baek Jin, KIM Yong Jin, Mishra Vivek, Son Guang Meang
Принадлежит: Korea Institute of Industrial Technology

The present disclosure relates to a method for preparing a disubstituted urea and carbamate compounds simultaneously through a one-pot reaction of an amine, carbon dioxide and an alkylene oxide compound in the presence of an ionic liquid-based complex catalyst system containing indium. In accordance with the present disclosure, a disubstituted urea and carbamate compounds can be prepared simultaneously at high yield. In addition, the ionic liquid-based catalyst containing indium according to the present disclosure is economical because it can be reused several times. 2. The method of claim 1 , wherein the ionic liquid-based catalyst system containing indium is a complex catalyst system represented by Chemical Formula 6 comprising a main catalyst represented by Chemical Formula 4 and an alkali metal halide represented by Chemical Formula 5 as a promoter:{'br': None, 'sub': (4-n)', 'n, '[Q][InXY]\u2003\u2003[Chemical Formula 4]'}{'br': None, 'MZ\u2003\u2003[Chemical Formula 5]'}{'br': None, 'sub': (4-n)', 'n, '[Q][InXY]-MZ\u2003\u2003[Chemical Formula 6]'}wherein{'sub': (4-n)', 'n, '[Q] stands for a cation of an ionic liquid, [InXY] stands for an anion of the ionic liquid and MZ stands for an alkali metal halide, wherein Q is imidazolium, phosphonium, ammonium or pyridinium, X is Cl, Br or I, Y is Cl or Br, M is an alkali metal, Z is Cl, Br or I, and n is an integer from 0 to 3.'}3. The method of claim 2 , wherein the cation of the ionic liquid is selected from the group consisting of 1-butyl-3-methylimidazolium (Bmim) claim 2 , tetra-n-butylphosphonium (TBP) claim 2 , tetra-n-butylammonium (TBA) claim 2 , tetra-n-butylpyridinium (CPy) claim 2 , and choline (Chol); the anion of the ionic liquid is selected from the group consisting of InCl claim 2 , InClBr claim 2 , InClI claim 2 , InBrCl claim 2 , and InBr; and the alkali metal halide is selected from the group consisting of NaI claim 2 , NaBr claim 2 , NaCl claim 2 , KI claim 2 , KBr claim 2 , KCl claim 2 , RbI ...

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Номер записи: 50
07-08-2014 дата публикации

GOLD-CATALYZED SYNTHESIS OF CARBONATES AND CARBAMATES FROM CARBON MONOXIDE

Номер: US20140221679A1
Автор: Friend Cynthia M., Madix Robert J., Xu Bingjun
Принадлежит: President and Fellows of Harvard College

The invention provides a method for producing organic carbonates via the reaction of alcohols and carbon monoxide with oxygen adsorbed on a metallic gold or gold alloy catalyst. 2. The method of claim 1 , wherein X is O.3. The method of claim 1 , wherein X is NR.4. The method of claim 1 , wherein the source of the adsorbed oxygen is O.5. The method of claim 1 , wherein the source of the adsorbed oxygen is O.6. The method of claim 1 , wherein Ris C1-C8 straight chain alkyl.7. The method of claim 6 , wherein Ris methyl.8. The method of claim 1 , wherein Ris C1-C8 straight chain alkyl.9. The method of claim 8 , wherein Ris methyl.10. The method of claim 1 , wherein X is O claim 1 , and Rand Rare the same.11. The method of claim 1 , wherein X is O claim 1 , and Rand Rare different.12. The method of claim 1 , wherein Ris C1-C8 straight chain alkyl.13. The method of claim 1 , wherein ROH is supplied in the gas phase claim 1 , and the temperature is between 250 K and 300 K. This application claims benefit of U.S. provisional application No. 61/572,416, filed Jul.This invention was made with government support under DE-FG02-84-ER13289 awarded by the U.S. Department of Energy and under CHE-0952790 awarded by the National Science Foundation. The Government has certain rights in the invention.The invention is in the fields of synthetic organic chemistry and catalysis, and relates specifically to a process for preparing carbonates and carbamates. More particularly, the present invention relates to a process for preparing carbonates and carbamates via oxidative carbonylation in the presence of a metallic gold catalyst.Dialkyl carbonates are industrially useful as lubricants, fuel additives, and reactive reagents in a wide variety of processes. In particular, dimethyl carbonate (DMC) has found use as an environmentally-acceptable solvent, high-octane oxygenated fuel additive, and esterifying and methylating agent, and the future demand for DMC is projected to exceed current ...

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Номер записи: 51
30-04-2020 дата публикации

METHODS AND INTERMEDIATES FOR SYNTHESIZING SK1-I

Номер: US20200131113A1
Автор: LI ZAIGUO, Pande Praveen, Raju Natarajan
Принадлежит: ENZO BIOCHEM, INC.

The invention provides methods for synthesizing the compound (2R,3S,4E)-N-methyl-5-(4′-pentylphenyl)-2-aminopent-4-ene-1,3-diol, also known as SK1-I, and intermediate compounds used in its synthesis. 2. The method of claim 1 , wherein R is a linear alkyl group.3. The method of claim 1 , wherein R is a branched alkyl group.5. The method of claim 4 , wherein R is a linear alkyl group.6. The method of claim 5 , wherein R is a CHgroup.7. The method of claim 4 , wherein R is a branched alkyl group. This application is a continuation of U.S. patent application Ser. No. 16/169,056 filed Oct. 24, 2018, which claims the benefit of U.S. provisional application Ser. No. 62/576,943 filed Oct. 25, 2017 each of which is hereby incorporated by reference in its entirety.The present invention relates to the field of organic synthesis of pharmaceutical compounds.(2R,3S,4E)-N-methyl-5-(4′-pentylphenyl)-2-aminopent-4-ene-1,3-diol, also known as SK1-I and BML-258 (as HCl salt), is a pharmaceutical inhibitor of sphingosine kinase 1 initially described in Paugh et al., Blood. 2008 Aug. 15; 112 (4): 1382-1391. An existing method for synthesizing SK1-I is disclosed in U.S. Pat. No. 8,314,151.What is needed and provided by the present invention are improved methods for synthesizing SK1-I and related compounds.One embodiment of the invention provides a method for synthesizing the compoundthat includes the reaction steps of:Another embodiment of the invention provides a method for synthesizing the compoundthat includes the reaction step of:A further embodiment of the invention provides a method for synthesizingthat includes the steps of: (i) reactingwith DIBAL in the presence of Rochelle salt, thereby obtainingIn one variation of this embodiment, Rochelle salt is provided in an aqueous solution that further includes sodium hydroxide.Still further embodiments of the invention provide complete multi-step syntheses of SK1-I and salts thereof from precursor compounds.The invention also provides ...

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Номер записи: 52
28-05-2015 дата публикации

AMINO ACID ANALOGUES AND METHODS FOR THEIR SYNTHESIS

Номер: US20150148524A1
Автор: Jackson William Roy, Robinson Andrea, Spiccia Nicolas Daniel, Wang Zhen
Принадлежит:

A method for the synthesis of an amino acid analogue or a salt, solvate, derivative, isomer or tautomer thereof comprising the steps of: (i) subjecting an amino acid containing a metathesisable group to metathesis with a compound containing a complementary metathesisable group of formula (I) or (II): (Formulae (I), (II)) wherein Rand Rare independently selected from H and substituted or unsubstituted Cto Calkyl; each Ris either absent or independently selected from a heteroatom, a substituted or unsubstituted Cto Calkyl, and a substituted or unsubstituted Cto Calkyl group interrupted by one or more heteroatoms; and each X is independently selected from H and an effector molecule; in the presence of a reagent to catalyse the metathesis to form a dicarba bridge between the amino acid containing a metathesisable group and the compound containing a complementary metathesisable group; and (ii) reducing the dicarba bridge to form a saturated dicarba bridge, wherein the reagent used to catalyse step (i) also catalyses step (ii). 4. The method of claim 3 , wherein the compound of formula (VI) is selected from:{'sup': 4', '5', '6, 'optionally protected allylglycine wherein Z is H or a protecting group, Y is H or a protecting group, Rand Rare H, and Ris absent;'}{'sup': 4', '5', '6, 'optionally protected crotylglycine wherein Z is H or a protecting group, Y is H or a protecting group, one of Rand Ris H and the other is methyl, and Ris absent; or'}{'sup': 4', '5', '6, 'optionally protected butenylglycine wherein Z is H or a protecting group, Y is H or a protecting group, Rand Rare H, and Ris methylene.'}5. The method of any one of to claim 3 , wherein the heteroatom is selected from group consisting of O claim 3 , S(O) claim 3 , S(O) claim 3 , SONH claim 3 , OS(O)O claim 3 , NH claim 3 , N(R) claim 3 , PO claim 3 , and P(R) claim 3 , wherein each Ris independently a substituted or unsubstituted Cto Calkyl.6. The method of any one of to claim 3 , wherein each Ris the same and ...

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Номер записи: 53
28-05-2015 дата публикации

PROCESS FOR MAKING AMINO ACID COMPOUNDS

Номер: US20150148559A1
Автор: Remarchuk Travis
Принадлежит: Genentech, Inc.

The invention provides new processes for making and purifying amino acid compounds, which are useful in the preparation of AKT inhibitors used in the treatment of diseases such as cancer, including the compound (S)-2-(4-chlorophenyl)-1-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-(isopropylamino)propan-1-one. 4. The process of claim 3 , wherein said compound —NHRRis —NH(isopropyl).6. The process of claim 5 , wherein said basic conditions comprise a base selected from hydroxide or alkoxide base.7. The process of claim 1 , wherein Ris an amino protecting group.8. The process of claim 1 , wherein said amino protecting group is selected from acetyl claim 1 , trifluoroacetyl claim 1 , phthalimide claim 1 , benzyl claim 1 , triphenylmethyl claim 1 , benzylidenyl claim 1 , p-toluenesulfonyl claim 1 , p-methoxybenzyl claim 1 , tert-butyloxycarbonyl claim 1 , 9-fluorenylmethyloxycarbonyl and carbobenzyloxy.9. The process of claim 1 , wherein Ris tert-butyloxycarbonyl and Ris isopropyl.10. The process of claim 1 , wherein said reducing comprises contacting a compound of formula II claim 1 , or a salt thereof claim 1 , with a metal catalyst and hydrogen gas.11. The process of claim 10 , wherein said metal catalyst is a ruthenium claim 10 , rhodium claim 10 , or palladium catalyst.12. The process of claim 10 , wherein said metal catalyst is [(S)-BINAPRuCl(benzene)]Cl.13. The process of claim 1 , wherein Ris an amino protecting group.14. The process of claim 1 , wherein Ris C-Calkyl.15. The process of claim 1 , wherein Ris isopropyl.18. The compound of claim 17 , wherein Ris hydrogen or t-butyloxycarbonyl; Ris C-Calkyl; and Ris hydrogen or C-Calkyl.19. The compound of claim 17 , wherein Ris hydrogen; Ris isopropyl; and Ris hydrogen or ethyl.21. The compound of claim 17 , wherein Ris t-butyloxycarbonyl.22. The compound of claim 20 , wherein Ris t-butyloxycarbonyl. This application claims priority to U.S. Provisional Application No. ...

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Номер записи: 54
17-06-2021 дата публикации

METHOD FOR PRODUCING CARBAMATE AND METHOD FOR PRODUCING ISOCYANATE

Номер: US20210179548A1
Автор: Miyake Nobuhisa, NAGAMOTO Midori, NAKAOKA Koichi, SAKURAI Yusuke, Shinohata Masaaki, TAKAGAKI Kazuhiro
Принадлежит: ASAHI KASEI KABUSHIKI KAISHA

The present invention provides a method for producing a carbamate that includes a step (1) and a step (2) described below: 1. A method for producing a carbamate comprising a step (1) and a step (2) described below:(1) a step of producing a compound (A) having a urea linkage, using an organic primary amine having at least one primary amino group per molecule and at least one compound selected from among carbon dioxide and carbonic acid derivatives, at a temperature lower than a thermal dissociation temperature of a urea linkage; and(2) a step of reacting the compound (A) with a carbonate ester to produce a carbamate.2. The method for producing a carbamate according to claim 1 , wherein in the step (1) claim 1 , when producing the compound (A) using the organic primary amine and carbon dioxide claim 1 , reaction is conducted while extracting claim 1 , from the reaction system claim 1 , water produced by the reaction between the organic primary amine and carbon dioxide.3. The method for producing a carbamate according to claim 1 , wherein the carbonic acid derivative is at least one compound selected from among N-unsubstituted carbamate esters claim 1 , N claim 1 ,N-disubstituted ureas claim 1 , N-substituted ureas claim 1 , and urea.4. The method for producing a carbamate according to claim 1 , wherein the organic primary amine has two or three primary amino groups per molecule.5. The method for producing a carbamate according to claim 1 , wherein the organic primary amine is at least one compound selected from among amino acid esters and salts of amino acid esters.6. The method for producing a carbamate according to claim 1 , whereinthe organic primary amine has a carboxy group, andthe method further comprises a step (Y) described below, either before the step (1), or after the step (1) but before the step (2):(Y) a step of esterifying the carboxy group of the organic primary amine, or esterifying the carboxy group of the compound (A) obtained in the step (1).7. The ...

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Номер записи: 55
11-06-2015 дата публикации

PROCESS FOR THE PREPARATION OF PYRAZOLE CARBOXYLIC ACID DERIVATIVES

Номер: US20150158818A1
Автор: Bartels Bjoern, Bliss Fritz, Groebke Zbinden Katrin, KOERNER Matthias
Принадлежит: Hoffmann-La Roche Inc.

The present invention relates to a novel process for the preparation of a pyrazole carboxylic acid derivative of the formula 2. Process of claim 1 , wherein step a) and step b) are combined and wherein the aminomethylene succinic acid ester of the formula IV is not isolated.3. Process of claim 1 , wherein the base used in step a) can be selected from a C-trialkylamine combined with a catalytic amount of 4-(dimethylamino)-pyridine or from pyridine.4. Process of claims 1 , wherein step a) is performed in an aprotic organic solvent claims 1 , or mixtures thereof claims 1 , at reaction temperatures between −20° C. and 40° C.5. Process of claim 1 , wherein the N-protected hydrazine derivative of formula V used in step b) can be selected from N-Boc-N-methylhydrazine claim 1 , N-Boc-N-ethylhydrazine claim 1 , N-Boc-N-n-propylhydrazine claim 1 , N-Cbz-N-methylhydrazine claim 1 , N-Fmoc-N-methylhydrazine claim 1 , N-Moz-N-methylhydrazine claim 1 , N-Troc-N-methylhydrazine claim 1 , N-Teoc-N-methylhydrazine claim 1 , N-Adoc-N-methylhydrazine. N-formyl-N-methylhydrazine. N-acetyl-N-methylhydrazine. N-cyclobutoxycarbonyl-N-methylhydrazine.6. Process of claim 1 , wherein step b) is performed in a polar aprotic or protic organic solvent claim 1 , or mixtures thereof claim 1 , at reaction temperatures between −10° C. and 60° C. claim 1 , or claim 1 , if step step a) and b) are combined claim 1 , wherein step b) is performed in a polar aprotic organic solvent claim 1 , or mixtures thereof claim 1 , at reaction temperatures between −10° C. and 60° C.7. Process of claim 1 , wherein step b) is performed in the presence of an acid claim 1 , which is not able to affect the amino protecting group of the hydrazinomethylene succinic acid ester of the formula VI.8. Process of claim 1 , wherein the ring closing in step c) is performed with an inorganic acid claim 1 , an organic acid or a Lewis acid in a polar solvent claim 1 , or mixtures thereof claim 1 , at reaction temperatures between 0° ...

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Номер записи: 56
14-05-2020 дата публикации

SILICA-BASED ZINC CATALYSTS, THEIR PREPARATION AND USE IN THE ALKOXYCARBONYLATION OF AMINES

Номер: US20200147594A1
Автор: Dugal Markus, Jaeger Gernot, Nuñez Rico Jose Luis, Vidal Ferran Anton, Wershofen Stefan
Принадлежит:

The present invention relates to silica-based heterogeneous zinc compounds which are suitable as catalysts in the reaction of amines with dialkyl carbonates to produce carbamates. The catalysts have the formula [SiO]—CH—CHR—X—COOZn[Y], wherein [SiO] represents a silica carrier selected from the group consisting of ordered mesoporous silica and irregular amorphous narrow pore silica, R represents a moiety selected from the group consisting of hydrogen, —CH, and —CHCH, preferably hydrogen, X is an aliphatic chain of 2 to 11 carbon atoms that optionally comprises ether moieties and [Y] represents a mono anion. The invention is also directed towards a method for the preparation of the aforementioned compounds and towards method for the alkoxycarbonylation of amines. 1. A silica-based zinc compound of the formula{'br': None, 'sub': 2', '2, '[SiO]—CH—CHR—X—COOZn[Y]'}{'sub': 2', '2', '2, 'claim-text': [{'sub': 3', '2', '3, 'R represents a moiety selected from the group consisting of hydrogen, —CH, and —CHCH;'}, 'X is an aliphatic chain of 2 to 11 carbon atoms that optionally comprises ether moieties; and', '[Y] represents a mono anion., 'wherein [SiO] represents a silica carrier selected from the group consisting of ordered mesoporous silica and irregular amorphous narrow pore silica, said silica carrier [SiO2] being covalently bound to the terminal CHgroup of CH—CHR—X—COOZn[Y];'}2. The silica-based zinc compound according to claim 1 , wherein X is an aliphatic chain of 2 to 9 carbon atoms that optionally comprises ether moieties.3. The silica-based zinc compound according to claim 2 , wherein X is selected from the group consisting of —(CH)— claim 2 , —(CH)— and —CH—O—(CH)—.4. The silica-based zinc compound according to claim 1 , wherein said compound{'sub': 2', '2, '(a) has a structure A in which the mono anion [Y] comprises a carboxylate group, the carboxylate oxygen atoms coordinating to the zinc atom and the carboxylate carbon atom being covalently connected to the ...

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Номер записи: 57
14-05-2020 дата публикации

A PROCESS FOR THE SYNTHESIS OF AROMATIC CARBAMATES

Номер: US20200148631A1
Автор: KELKAR Ashutosh Anant, NIVANGUNE Nayana Tushar, RANE Vilas Hari
Принадлежит:

The present invention discloses a process for the synthesis of aromatic carbamates from amine with dialkyl carbonate in the presence of binary or ternary mixed metal oxide catalyst. The present invention further discloses the yield of said aromatic carbamate in the range of 60 to 99%. Further, the ratio of amine to dialkyl carbonate is in the range of 1:2 to 1:30. 110-. (canceled)11. A process for the synthesis of aromatic carbamate , the process comprising the step of reacting amine with dialkyl carbonate in the presence of a binary or ternary mixed metal oxide catalyst at a temperature in the range of 100 to 220° C. and for a period in the range of 1 to 15 hours to obtain corresponding aromatic carbamate , wherein yield of said aromatic carbamate is in the range of 60 to 99%.12. The process as claimed in claim 11 , wherein said process is carried out in presence of solvent.14. The process as claimed in claim 13 , wherein said amine is selected from aniline claim 13 , 4-methylbenzene-1 claim 13 ,3-diamine claim 13 , 4 claim 13 ,4′-methylenedianiline claim 13 , 2 claim 13 ,4-dimethylaniline claim 13 , 3 claim 13 ,4-dimethylaniline claim 13 , 2 claim 13 ,6-dimethylaniline claim 13 , 4-chloroaniline claim 13 , 4-methoxyaniline claim 13 , o-toluidine claim 13 , m-toluidine claim 13 , p-toluidine claim 13 , toluene diamine or diaminodiphenyl methane.15. The process as claimed in claim 11 , wherein said dialkyl carbonate is selected from dimethyl carbonate or diethyl carbonate.16. The process as claimed in claim 11 , wherein said binary or ternary mixed metal oxide catalyst is XYZO claim 11 , wherein X is at least one metal selected from Group 3 elements claim 11 , Y is at least one metal selected from transition metals of the Periodic Table claim 11 , Z is at least one of the metal/metalloid selected from zirconium claim 11 , aluminium and silica; a claim 11 , b and c are the molar ratios of their respective components claim 11 , a claim 11 , b and c can vary from 0 to ...

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Номер записи: 58
16-06-2016 дата публикации

Reaction Method Accompanied by Production of Gas Component

Номер: US20160166950A1
Автор: Miyake Nobuhisa, SASAKI Takeharu, Shinohata Masaaki
Принадлежит: ASAHI KASEI CHEMICALS CORPORATION

The present invention relates to a reaction method comprising a step of supplying a liquid containing at least one raw material compound and a low-boiling compound having a standard boiling point lower than a standard boiling point of the raw material compound to a flow channel, a step of heating the liquid to produce a liquid reaction product and a gas component by a reaction of the raw material compound, and a step of separating a liquid phase containing the reaction product from a gas phase containing the gas component and the low-boiling compound. 1. A reaction method accompanied by production of a gas component , comprising:a step of supplying a liquid containing at least one raw material compound and a low-boiling compound having a standard boiling point lower than a standard boiling point of the raw material compound to a flow channel;a step of heating the liquid to produce a liquid reaction product and a gas component by a reaction of the raw material compound; anda step of separating a liquid phase containing the reaction product from a gas phase containing the gas component and the low-boiling compound.2. The method according to claim 1 , wherein a stoichiometric proportion of the raw material compound to the reaction product in the liquid is raw material compound:reaction product=100:0 to 80:20.3. The method according to claim 1 , wherein the flow channel has a specific surface area of 10 m/mor more and less than 1000 m/m.4. The method according to claim 1 , wherein the low-boiling compound is collected as a component contained in the gas phase and/or the liquid phase.5. The method according to claim 1 , wherein the gas phase containing the gas component and the low-boiling compound is produced in the flow channel.6. The method according to claim 1 , wherein the standard boiling point of the low-boiling compound is lower than the standard boiling point of the raw material compound by 10° C. or more.7. The method according to claim 1 , wherein the gas ...

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Номер записи: 59
16-06-2016 дата публикации

INTEGRATED PROCESS FOR CARBON CAPTURE AND ENERGY PRODUCTION

Номер: US20160167974A1
Автор: Novek Ethan
Принадлежит:

The present invention pertains to new methods for generating energy and useful nitrogen compounds from captured carbon dioxide. It involves employing an osmotic engine, draw solution, and feed solution. An osmotic gradient between the solutions assists in generating energy and a solution of ammonium carbonate, ammonium bicarbonate or mixture thereof. This solution may be decomposed to form ammonia, carbon dioxide, a precipitate, or a mixture thereof. 2. The integrated process of which further comprises:employing an osmotic engine comprising: (1) the formed solution of ammonium carbonate, ammonium bicarbonate, ammonium carbamate or mixture thereof as a draw solution and (2) a feed solution having a lower osmotic pressure than said draw solution to generate a gradient; andusing the gradient to generate energy and a second solution of ammonium carbonate, ammonium bicarbonate, ammonium carbamate or mixture thereof wherein said second solution has a lower osmotic pressure than the draw solution and wherein at least a portion of said second solution is subjected to decomposing.3. The integrated process of wherein the engine is selected from the group consisting of pressure retarded osmosis system claim 2 , reverse electrodialysis claim 2 , and capacitive mixing power production.4. The integrated process of wherein the osmotic engine is a pressure retarded osmosis system wherein the transfer of water from the feed solution across one or more membranes is employed to generate electricity via a hydroelectric generator.5. The integrated process of wherein the draw solution is formed by capturing carbon dioxide with ammonia.6. The integrated process of wherein the captured carbon dioxide used to form the solution comprises carbon dioxide captured from combustion or oxidation of one or more hydrocarbons claim 1 , from steam reforming claim 1 , from gas shift reaction claim 1 , from catalytic reforming claim 1 , from natural gas purification claim 1 , from land fill gas claim 1 ...

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Номер записи: 60
15-06-2017 дата публикации

COMPOSITIONS AND METHODS FOR SYNTHESIZING (2S,3S)-TRANS-EPOXYSUCCINYL-L-LEUCYL-AMIDO-3-METHYLBUTANE ETHYL ESTER

Номер: US20170166543A1
Автор: Eisenreich Emerich, Haines Kenneth A., Levin Daniel, Liu Hui, Liu Xuejun, TERNANSKY Robert J.
Принадлежит:

In alternative embodiments the invention provides methods for synthesizing AB-007 (also called loxistatin, E64d, EST or ((2S,3S)-trans-epoxysuccinyl-L-leucyl-amido-3-methylbutane ethyl ester) and its acid form E64c (loxistatin acid), and various synthetic intermediates, and deuterated forms of these compounds, and stereoisomers thereof. In alternative embodiments the invention provides a tosylate salt of AB-007-4 or a tosylate salt of L-leucine isoamylamine, or equivalents thereof. A synthetic scheme of the invention provides kilogram quantities of AB-007 manufactured according to current good manufacturing practices (cGMP's), consistent with US FDA requirements for human use. In alternative embodiments the invention provides a tosylate salt of AB-007-4 or a tosylate salt of L-leucine isoamylamine, or equivalents thereof. 1: A composition comprising: a tosylate salt of AB-007-4; or , a tosylate salt of L-leucine isoamylamine; or , equivalents thereof.2: A tosylate salt of AB-007-4 or a tosylate salt of L-leucine isoamylamine , or equivalents thereof.3: A synthetic scheme comprising at least one scheme: (a) as set forth in ; (b) as set forth in Scheme Ia , Scheme Ib , Scheme II , Scheme C and/or Scheme D , of Example I; or (c) equivalents of (a) and (b).9: The synthetic scheme of claim 4 , wherein:(a) in place of using EDCI/HOBt standard peptide coupling conditions for a coupling reaction, optionally, as in Scheme I, a reagent comprising or consisting of propylphosphonic anhydride, or propane phosphonic acid anhydride (T3P®), is used for the coupling reaction;(b) in place of using BOC deprotection of AB-007-2 starting material, optionally, before step 1 of Scheme I, alternative conditions comprising controlled addition of a solution of AB-007-3 into a warm solution of excess p-toluene sulfonic acid can be used to provide effective control of gas evolution rate by adjusting the addition rate of the AB-007-3 solution, as needed; these conditions can be used to ensure a ...

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Номер записи: 61
30-05-2019 дата публикации

PROCESS FOR PREPARING ACYLATED AMPHETAMINE DERIVATIVES

Номер: US20190161435A1
Автор: McClenaghan Joel, Orr Brian, Roesch Kevin
Принадлежит:

Processes for preparing acetylated amphetamine derivatives and, in particular, processes for preparing -lysine--amphetamine dimesylate from -amphetamine salts. 2. The process of claim 1 , wherein R is an amino acid side chain chosen from —(CH)—NH claim 1 , —(CH)—NH—C(NH)—NH claim 1 , —(CH)—NH—C(NH)—NH claim 1 , —CH—C(O)—NH claim 1 , —(CH)—C(O)—NH claim 1 , —CH—SH claim 1 , —CH—OH claim 1 , CH(OH)—CH claim 1 , —CH-Ph-OH claim 1 , —CH2-C(O)—OH claim 1 , or —(CH)—C(O)—OH; LG is N-hydroxysuccinimidyl or halo; and PG is tert-butyloxycarbonyl claim 1 , triphenylmethyl claim 1 , dimethyl-3 claim 1 ,5-dimetheoxybenzyloxycarbonyl claim 1 , 2-(4-biphenyl)isopropoxycarbonyl claim 1 , 2-nitropheylsulfenyl claim 1 , 2-chlorobenzyloxycarbonyl claim 1 , or 4-methyltriphenymethyl.3. The process of claim 1 , wherein the alkyl tetrahydrofuran and the compound of Formula (I) are present in the reaction mixture at a weight ratio of about 5:1 to about 15:1; steps (b) and (c) are conducted at room temperature; step (c) comprises sequential contact with a water solution claim 1 , an acid solution having a pH of less than about 3 claim 1 , an alkaline solution having a pH of greater than about 12 claim 1 , and one or more additional water solutions; the acid at step (d) is methanesulfonic acid claim 1 , hydrochloric acid claim 1 , or oxalic acid; and step (d) is conducted at a temperature from about 40° C. to about 70° C.4. The process of claim 1 , wherein the intermediate compound of Formula (III) is not isolated after step (b) or step (c).5. The process of claim 1 , further comprising azeotropically drying the purified mixture comprising the intermediate compound of Formula (III) after step (c) until it has a water content of less than about 2% by weight.6. The process of claim 1 , further comprising isolating the compound of Formula (IV) after step (d) by filtration.7. The process of claim 6 , further comprising recrystallizing the compound of Formula (IV).9. A one-pot process for ...

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Номер записи: 62
23-06-2016 дата публикации

METHODS OF SYNTHESIZING A LEVODOPA ESTER PRODRUG

Номер: US20160176804A1
Автор: Estrada Tono, MANN ADAM, Manthati Suresh K., Nguyen Mark Q., Raillard Stephen P., Scheuerman Randall A., Zhou Cindy X.
Принадлежит:

Methods of synthesizing a levodopa ester prodrug, salts thereof, and synthetic intermediates thereof are disclosed.

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Номер записи: 63
06-06-2019 дата публикации

Improved process for the preparation of carbamates

Номер: US20190169115A1
Автор: Dieter Ulrichts, Frederik Van Waes, Kristof Moonen
Принадлежит: Taminco BV

A process for the preparation of N-(dialkylaminoalkyl)-carbamic acid esters, in particular (propyl N-[3-(dimethylamino)propyl] carbamate) comprising an oxidative carbonylation reaction of a compound of general structure (II) wherein each of R 1 and R 2 , equal to or different from each other, are independently selected from an alkyl group having 1 to 10 carbon atoms, which is optionally substituted by at least one halogen atom, an aryl group or an aralkyl group; R 3 is selected from an alkyl group having 1 to 36 carbon atoms, which is optionally substituted by at least one halogen atom, an aryl group or an aralkyl group; each of R′, R″ and R 4 , equal to or different from each other, are independently selected from H, an alkyl group having 1 to 10 carbon atoms, which is optionally substituted by at least one halogen atom, an aryl group or an aralkyl group; and n is an integer in the range from 1 to 8, with a hydroxyl compound of general formula (III), R 3 —OH (III) and in the presence of a catalyst system.

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Номер записи: 64
30-06-2016 дата публикации

A Process to Produce Polycarbamate, Polycarbamate Produced Thereby and a Coating Composition Comprising the Polycarbamate

Номер: US20160185713A1
Автор: Beigzadeh Daryoosh, Clark Thomas, He Yiyong, Hull John W., Lu Congcong, Margi Peter, Romer Duane, Yu Xinrui
Принадлежит: Dow Global Technologies LLC

A process to prepare polycarbamate comprising adding urea to a polyol in the presence of at least one catalyst selected from the group consisting of compounds having the following formula MZ; wherein M is a trivalent metal, and Z is an anionic functionality or a functionality capable of forming a covalent bond with M and wherein n times a valence number of Z equals X and m times three equals Y wherein the absolute value of X equals the absolute value of Y is provided. Also provided are a polycarbamate produced according to the process and a coating composition comprising the polycarbamate. 1. A process to prepare polycarbamate comprising:{'sub': m', 'n, 'adding urea to a polyol in the presence of at least one catalyst selected from the group consisting of compounds having the following formula MZ; wherein M is a trivalent metal selected from the group consisting of Bi(III), Al(III), Yb(III), Y(III), Fe(III), La(IIII), Sm(IIII), Ru(III), Ga(III), Sc(III) or Ce(III), and wherein Z is selected from the group consisting of 2-ethylhexanoate, benzoate, hexafluoroacetylacetonate, isopropoxide, acetyl acetonate, hydroxyl, phenoxide, stearate, tert-butoxide, neodecanoate, citrate, trifluoromethane sulfonate, n-butoxide, trifluoroacetate, 1,1,1-trifluoro-2,4-pentanedionate, 2,2,6,6,-tetramethyl-3,5-hexanedionate, cresylate, ethoxide, methoxide, triethanolaminato, 2-methyl-2-butoxide, oxo, fluoride, chloride, bromide, iodide, aryl or substituted aryl, mixtures thereof and chelates thereof, and wherein Z is an anionic functionality or a functionality capable of forming a covalent bond with M.'}2. The process according to claim 1 , wherein a second catalyst selected from the group consisting of carbamylation catalysts is present.3. The process according to claim 2 , wherein the second catalyst is dibutyltin oxide and/or dibutyltin acetate.4. (canceled)5. (canceled)4. The process according to claim 1 , wherein the catalyst is selected from the group consisting of: Bismuth(III) ...

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Номер записи: 65
30-06-2016 дата публикации

CARBOXYLIC ACID ESTER/CARBAMATE COMPOUND WITH POLYMERIZABLE FUNCTIONAL GROUP AND FLUORINE ATOM GROUP, AND MANUFACTURING METHOD THEREFOR

Номер: US20160185714A1
Автор: Ikeda Sunao, KOKINN Keisuke, MIYAMURA Takuhiro
Принадлежит:

Provided are a fluorine-containing monomer soluble in a hydrocarbon-based solvent as well as excellent in water and oil repellence, and a manufacturing method therefor. The fluorine-containing monomer is a carboxylic acid ester/carbamate compound having a polymerizable functional group and a fluorine atom group, and represented by the following general formula: CFO—(CFO)—CFCOO—Z—(CONHR). The method for manufacturing the carboxylic acid ester/carbamate compound is comprised of the steps of making an isocyanate compound having a polymerizable functional group react with an alcohol such as a polyalkylene glycol, a cycloalkane dimethanol, or a polyhydric alcohol to produce a hydroxycarbamate, and subsequently making the resulting hydroxycarbamate react with a perfluoropolyether carboxylic acid halide. 1. A carboxylic acid ester/carbamate compound having a polymerizable functional group and a fluorine atom group and represented by general formula [I]:{'br': None, 'sub': a', '2a+1', 'b', '2b', 'c', '2', '4', 'd, 'CFO—(CFO)—CFCOO—Z—(CONHR)\u2003\u2003[I]'}where a is an integer of 1 to 3; b is an integer of 1 to 4; c is an integer of 0 to 50; d is an integer of 1 to 3;{'sub': e', '2e', 'f', '2', 'g', '2g−2', '2', 'h', '2h+1−i', 'i, 'Z is a divalent to tetravalent organic linking group derived from a peroxide-free alcohol represented by —(CHO)—, —CH(cyclo-CH)CHO—, or —CHO—; where e is an integer of 1 to 6; f is an integer of 1 to 12; g is an integer of 3 to 6; h is an integer of 2 to 12; i is an integer of 1 to 3; and'} {'br': None, 'sub': 2', '2, 'sup': 1', '2', '3, 'HC═C(R)COOCHCRR—\u2003\u2003[II]'}, 'R is a polymerizable functional group represented by general formula [II]{'sup': 1', '2', '3, 'sub': 2', '2, 'where Ris hydrogen or methyl; Ris hydrogen or CH═CHCOOCH—; and Ris hydrogen or methyl.'}2. A method for manufacturing a carboxylic acid ester/carbamate , comprising the steps of:making an isocyanate compound having a polymerizable functional group and represented by ...

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Номер записи: 66
30-06-2016 дата публикации

PROCESS FOR SYNTHESIZING HIGHLY OPTICALLY ACTIVE 1,3-DISUBSTITUTED ALLENES

Номер: US20160185812A1
Автор: Fu Chunling, HUANG Xin, Ma Shengming
Принадлежит: Zhejiang University

The present invention relates to a process for efficiently synthesizing highly optically active 1,3-disubstituted allenes, i.e., a one-step process for preparing highly optically active 1,3-disubstituted allenes by using a functionalized terminal alkyne, an aldehyde and a chiral α,α-diphenyl prolinol as reactants under the catalysis of a divalent copper salt. The operation of the process is simple, and the raw materials and reagents are readily available. The process has a broad-spectrum of substrates and a good compatibility for a wide variety of functional groups such as glycosidic units, primary alcohols, secondary alcohols, tertiary alcohols, amides, malonates, etc., and does not require the protection for the functional groups. The obtained axially chiral allene has a moderate to high yield and a good diastereoselectivity or enantioselectivity. 2. The process for efficiently synthesizing highly optically active 1 claim 1 ,3-disubstituted allenes of claim 1 , characterized by comprising the following steps:1) under nitrogen atmosphere, a divalent copper salt, a chiral secondary amine, a terminal alkyne, an aldehyde and an organic solvent were added in sequence into a reaction tube subjected to the anhydrous and anaerobic treatment; heating for reaction for 12-24 h;2) after the completion of the reaction of step 1), raising the reaction tube from the oil bath, naturally returning to the room temperature, diluting with an organic solvent, transferring the liquid to a separatory funnel, washing with dilute hydrochloric acid, separating the organic phase, extracting the aqueous phase with the same organic solvent, combining the organic phases, washing with saturated brine, drying with anhydrous sodium sulfate, filtering, concentrating and subjecting to the column chromatography, so as to obtain the product, axially chiral allene.3. The process for efficiently synthesizing highly optically active 1 claim 1 ,3-disubstituted allenes of claim 1 , characterized by using ...

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Номер записи: 67
13-06-2019 дата публикации

A PROCESS FOR THE PREPARATION OF ELUXADOLINE

Номер: US20190177282A1
Автор: MADHRA Mukesh Kumar, Prasad Mohan, Singh Pankaj Kumar
Принадлежит:

The present invention relates to an improved process for the preparation of eluxadoline and its intermediates and that includes the use of an aqueous surfactant solution in the preparation of N-[(benzyloxy)carbonyl]-N-(2-oxo-2-phenylethyl)-L-alaninamide, an intermediate in the preparation of eluxadoline. 1. (canceled)4. (canceled)5. The process according to the claim 2 , wherein the coupling is carried out in the presence of a coupling agent selected from the group consisting of N claim 2 ,N′-dicyclohexylcarbodiimide (DCC) claim 2 , 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDCI) claim 2 , 1 claim 2 ,1′-carbonyldiimidazole (CDI) claim 2 , N claim 2 ,N claim 2 ,N′ claim 2 ,N′-tetramethyl-O-(benzotriazol-1-yl)uronium tetrafluoroborate (TBTU) claim 2 , N claim 2 ,N claim 2 ,N′ claim 2 ,N′-tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (HBTU) claim 2 , and (1-cyano-2-ethoxy-2-oxoethylidenaminooxy) dimethylamino-morpholino-carbenium hexafluorophosphate (COMU).7. The process according to the claim 2 , wherein the coupling is carried out in the presence of a base selected from the group consisting of triethylamine claim 2 , N-methylmorpholine claim 2 , 4-(N claim 2 ,N-dimethylamino)pyridine claim 2 , 2 claim 2 ,6-lutidine claim 2 , 1-methylpiperidine claim 2 , N-ethyldiisopropylamine claim 2 , N claim 2 ,N-diisopropylethylamine claim 2 , 2 claim 2 ,4 claim 2 ,6-trimethylpyridine claim 2 , and 2 claim 2 ,4 claim 2 ,6-collidine.8. The process according to claim 2 , wherein the coupling is carried out in the presence of an aqueous surfactant solution prepared by contacting an anionic surfactant claim 2 , a cationic surfactant claim 2 , or a nonionic surfactant with water.9. (canceled)10. (canceled)11. (canceled)12. (canceled) The present invention relates to an improved process for the preparation of eluxadoline and its intermediates.Eluxadoline chemically is 5-[[[(2S)-2-amino-3-[4-(aminocarbonyl)-2,6-dimethylphenyl]-1-oxopropyl][(1S)-1-(4-phenyl-1H- ...

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Номер записи: 68
09-07-2015 дата публикации

Process for the Preparation of 6-(7-((1-Aminocyclopropyl)Methoxy)-6-Methoxyquinolin-4-Yloxy)-N-Methyl-1-Naphthamide and Synthetic Intermediates Thereof

Номер: US20150191429A1
Автор: LIVI Valeria, SPINELLI Silvano
Принадлежит:

A process for the preparation in high yields and purity of the compound 6-(7-((1-aminocyclopropyl)methoxy)-6-methoxyquinolin-4-yloxy)-N-methyl-1-naphthamide of formula (I) and of the pharmaceutically acceptable salts thereof is described. The process has various advantages over those previously described, in particular it avoids the use of acyl azide intermediates and their Curtius rearrangement. Novel intermediates useful for the preparation of compound (I) are also described. 6. A compound as claimed in claim 1 , wherein said compound is:1-[(4-Acetyl-2-methoxyphenoxy)methyl]-N-benzyloxycarbonyl-1-aminocyclopropane.7. Method of synthesizing a compound as claimed in as an intermediate in the synthesis of 6-(7-((1-aminocyclopropyl)methoxy)-6-methoxyquinolin-4-yloxy)-N-methyl-1-naphthamide (I) or a pharmaceutically acceptable salt thereof.8. A compound as claimed in claim 2 , wherein the compound is 1-[(4-Acetyl-2-methoxy-5-nitrophenoxy)methyl]-N-benzyloxycarbonyl-1-aminocyclopropane.9. A compound as claimed in claim 3 , wherein the compound is 1-[(4-(3-Dimethylaminopropenoyl)-2-methoxy-5-nitrophenoxy)methyl]-N-benzyloxycarbonyl-1-aminocyclopropane.10. A compound as claimed in claim 4 , wherein the compound is 1-[(4-Hydroxy-6-methoxyquinolin-7-yloxy)methyl]-N-benzyloxycarbonyl-1-aminocyclopropane.11. A compound as claimed in claim 5 , wherein the compound is 1-[(4-Chloro-6-methoxyquinolin-7-yloxy)methyl]-N-benzyloxycarbonyl-1-aminocyclopropane. This application is a divisional of U.S. application Ser. No. 14/138,302, filed Dec. 23, 2013. U.S. application Ser. No. 14/138,302 is a divisional of U.S. application Ser. No. 13/256,722 filed on Sep. 15, 2011, now U.S. Pat. No. 8,642,767. U.S. application Ser. No. 13/256,722 is a 371 U.S. National phase of PCT/EP2010/001519 filed on Mar. 11, 2010, which claims priority to and benefit of Italian Application No. MI2009A000397 filed on Mar. 16, 2009, all of which are incorporated herein by reference in their entireties.The ...

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Номер записи: 69
29-06-2017 дата публикации

METHOD USING ZIRCONIUM CATALYST FOR PRODUCING CARBAMATE-FUNCTIONAL MATERIALS

Номер: US20170183436A1
Автор: JADHAV Abhijit
Принадлежит: BASF COATINGS GMBH

A carbamate-functional material is prepared by reacting a carbamate compound with a hydroxy-functional material using zirconium acetylacetonates catalyst. 1: A method of preparing a carbamate-functional material , the method comprising:reacting a carbamate compound with a hydroxy-functional material in the presence of a zirconium acetylacetonate catalyst to form a carbamate-functional material.2: The method according to claim 1 , wherein the carbamate compound is an alkyl carbamate.3: The method according to claim 2 , wherein the carbamate compound is at least one selected from the group consisting of methyl carbamate claim 2 , ethyl carbamate claim 2 , n-propyl carbamate claim 2 , isopropyl carbamate claim 2 , n-butyl carbamate claim 2 , isobutyl carbamate claim 2 , tert-butyl carbamate claim 2 , n-hexyl carbamate claim 2 , 2-ethylhexyl carbamate claim 2 , cyclohexyl carbamate claim 2 , and phenyl carbamate claim 2 , and combinations thereof.4: The method according to claim 1 , wherein the hydroxy-functional material is a monomeric compound comprising having from 1 to 160 carbon atoms.5: The method according to claim 1 , wherein the hydroxy-functional material comprises from 12 to 72 carbon atoms and at least two hydroxyl groups.6: The method according to claim 1 , wherein the hydroxy-functional material is obtained by a reduction of an addition product of unsaturated fatty acids.7: The method according to claim 1 , wherein the hydroxy-functional material is a hyperbranched polyol.8: The method according to claim 7 , wherein the reacting is performed during a final step of obtaining the hyperbranched polyol.9: The method according to claim 1 , wherein the hydroxy-functional material is at least one selected from the group consisting of polyester polyols claim 1 , polyether polyols claim 1 , polyhydroxy polycarbonates claim 1 , polyurethane polyols claim 1 , polyvinyl polymer polyols claim 1 , polyhydroxy polyesteramides claim 1 , polysiloxane polyols claim 1 , and ...

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Номер записи: 70
07-07-2016 дата публикации

ZINC CLUSTER COMPOUNDS AND THEIR USE AS CATALYSTS IN THE REACTION OF AMINES WITH DIALKYL CARBONATES

Номер: US20160194277A1
Автор: Dreier Thorsten, Haak Robert, Vidal Anton, Wershofen Stefan
Принадлежит: Covestro Deutschland AG

The present invention relates to metallic zinc cluster compounds which are suitable as catalysts in the reaction of amines with dialkyl carbonates to produce carbamates. The invention is also directed towards a method for the alkoxycarbonylation of amines. The cluster compound has a general formula which may be written as [M(OC—R)].[MO].[HO], wherein M is Zn, R is an unsubstituted or substituted aromatic, cycloaliphatic, linear aliphatic, or other organic rest, x is 1, y is ≧x is 1, y is ≧0.03 to ≦26.0 and z is >0.00 to ≦17.0. 1. A compound of the formula [Zn(OC—R)].[ZnO].[HO] 'x is 1, y is ≧0.03 to ≦26.0 and z is >0.00 to ≦17.0.', 'wherein R is an unsubstituted or substituted aromatic, cycloaliphatic, linear aliphatic, or other organic rest and'}2. The compound of claim 1 , wherein R is selected from the group of CH claim 1 , o- claim 1 , m- and p-CH—OMe claim 1 , o- claim 1 , m- and p-CH—OH claim 1 , p-CH—NFH claim 1 , p-CH—NO claim 1 , p-CH—Br claim 1 , o- and p-CH—CO claim 1 , 2-pyrrolidinyl claim 1 , heptadecanyl and/or CHCH(OH)CO.3. The compound of to claim 1 , wherein R is para-CH—OCHand wherein the zinc content as determined by thermogravimetric analysis is ≧20.0% to ≦45.0%.4. The compound of claim 1 , wherein R is para-CH—OCHand wherein the carbon content as determined by elemental analysis is ≧30.0% to ≦48.0% claim 1 , preferably ≧40.0 and ≦45.0.5. A method for producing the compound of claim 1 , comprising the steps of:{'sub': '2', 'A) providing an aqueous solution comprising a carboxylic acid HOC—R and a base, wherein R is an unsubstituted or substituted aromatic, cycloaliphatic, linear aliphatic, or other organic rest;'}B) providing an aqueous solution comprising a dissolved zinc salt; andC) combining the solutions of step A) and step B).6. The method of claim 5 , wherein R is selected from the group of CH claim 5 , o- claim 5 , m- and p-CH—OMe claim 5 , o- claim 5 , m- and p-CH—OH claim 5 , p-CH—NH claim 5 , p-CH—NO claim 5 , p-CH—Br claim 5 , o- and p ...

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Номер записи: 71
05-07-2018 дата публикации

METHOD FOR PRODUCING AMIDES OR POLYAMIDES BY USING AROMATIC CARBAMATES BY WAY OF ISOCYANATES AS PRECURSORS THROUGH CATALYZED THERMAL PROCESSES AND METHOD FOR PRODUCING AROMATIC CARBAMATE PRECURSORS FROM AROMATIC AMINES

Номер: US20180186731A1
Автор: Dai Shenghong A., LIN Ching Hsuan, YANG Jung-Yang
Принадлежит:

The present invention is directed to a process for preparing amides or polyamides by replacing isocyanate starting materials of a catalyzed thermal reaction with aromatic carbamates. Through the catalyzed thermal process involving a non-isocyanate precursor of the present invention, efficiency for producing amides or polyamides can be significantly improved, and the impure side products produced from a side reaction of isocyanate can be greatly curtailed. Hence, amides or polyamides of high purity and yield can be achieved. The invention also relates to a process for preparing aromatic carbamates, the new non-isocyanate precursors for amides or polyamides. 1. A method for preparing an amide or polyamide , comprising the steps of:(a) thermally cracking an aromatic carbamate in a polymerization solvent, to form an aromatic isocyanate solution;(b) subjecting the aromatic isocyanate to a self-condensation reaction in the presence of a carbodiimide (CDI) catalyst, to form an aromatic carbodiimide;(c) reacting the aromatic carbodiimide with a carboxylic acid, to form a reaction intermediate aromatic N-acyl urea; and(d) thermally cracking the aromatic N-acyl urea, to form the aromatic isocyanate and the amide or polyamide product;wherein Steps (b) to (d) are performed repeatedly.2. The method according to claim 1 , wherein in Steps (b) to (d) claim 1 , a sequential self-repetitive reaction (SSRR) is carried out.3. The method according to claim 1 , wherein the carboxylic acid is selected from the group consisting of a monocarboxylic acid claim 1 , a dicarboxylic acid claim 1 , and a mixture thereof.4. The method according to claim 3 , wherein the dicarboxylic acid is selected from the group consisting of an aliphatic diacid claim 3 , an aromatic diacid claim 3 , an aryl aliphatic diacid claim 3 , and a mixture thereof.5. The method according to claim 3 , wherein the carboxylic acid is selected from the group consisting of acetic acid claim 3 , benzoic acid claim 3 , oxalic ...

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Номер записи: 72
05-07-2018 дата публикации

MULTI-FUNCTIONAL CARBAMATE HAVING SOFT-SEGMENTS, POLYISOCYANATE OBTAINED VIA SUBSEQUENT NON-PHOSGENE SYNTHESIS METHODS, URETHANE PREPOLYMER AND ELASTOMERIC URETHANE HAVING SOFT-SEGMENTS DERIVED THEREFROM, AND PREPARATION METHOD THEREOF

Номер: US20180186918A1
Автор: Dai Shenghong A., Liao Kevin, LIN Ching Hsuan, Nien Wei Ming, Pan Wen Chen
Принадлежит:

The present invention relates to a multi-functional carbamate having a soft segment, which can be used as a raw material in the preparation of a polyisocyanate having a special siloxane soft segment in its structure by a non-phosgene method; to a polyisocyanate having a special siloxane soft segment prepared by a non-phosgene method; to a urethane prepolymer having a special siloxane soft segment, prepared from a polyisocyanate having a special siloxane soft segment and a polyol; and also to a elastomeric urethane having a special siloxane soft segment, prepared by reacting a polyisocyanate having a special siloxane soft segment with a polyol and an optional chain extender. The present invention also relates to a synthesis method for the above-mentioned substances. 1. A method for synthesizing a polyurethane having a siloxanyl group in its backbone , comprising reacting a polyisocyanate having a siloxanyl group in its backbone , a polyol , and an optional chain extender.2. The method according to claim 1 , wherein the polyisocyanate having a siloxanyl group in its backbone is reacted with the polyol to form a prepolymer before the reaction to form the polyurethane is carried out.3. The method according to claim 1 , wherein the polyol is represented by Formula (6) below:{'br': None, 'sub': 'p', 'sup': '3', '(HO)—R\u2003\u2003(6)'}{'sup': '3', 'sub': 1-16', '3-16, 'wherein Ris a p-valent group derived from a linear or branched Chydrocarbyl or a Ccyclohydrocarbyl, and p is an integer of at least 2.'}4. The method according to claim 1 , wherein the chain extender is a polyisocyanate having no soft segments.5. The method according to claim 4 , wherein the polyisocyanate having no soft segments comprises 1 claim 4 ,6-hexamethylene diisocyanate (HDI) claim 4 , 4 claim 4 ,4-methylenediphenyl diisocyanate (MDI) claim 4 , toluene diisocyanate (TDI) claim 4 , 1 claim 4 ,4-phenylene diisocyanate (PPDI) claim 4 , isophorone diisocyanate (IPDI) claim 4 , dicyclohexyl methane ...

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Номер записи: 73
06-07-2017 дата публикации

ACYLOXYALKYL CARBAMATE PRODRUGS, METHODS OF SYNTHESIS AND USE

Номер: US20170190657A1
Автор: Gallop Mark A., Ludwikow Maria J., Peng Ge, Phan Thu, Yao Fenmei
Принадлежит: XenoPort, Inc.

The disclosures herein relate generally to acyloxyalkyl carbamate prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof, pharmaceutical compositions thereof, methods of making prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof, methods of using prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof, and pharmaceutical compositions thereof for treating or preventing common diseases and/or disorders such as spasticity and/or acid reflux disease. The disclosures herein also relate to acyloxyalkyl carbamate prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof which are suitable for oral administration and to sustained release oral dosage forms thereof. 152-. (canceled)54. The method of claim 53 , wherein Ris hydrogen.55. The method of wherein Ris selected from Calkyl claim 53 , substituted Calkyl claim 53 , Ccycloalkyl claim 53 , phenyl claim 53 , substituted phenyl claim 53 , Cphenylalkyl and pyridyl.56. The method of claim 53 , wherein Ris selected from methyl claim 53 , ethyl claim 53 , n-propyl claim 53 , isopropyl claim 53 , n-butyl claim 53 , isobutyl claim 53 , sec-butyl claim 53 , tert-butyl claim 53 , n-pentyl claim 53 , isopentyl claim 53 , sec-pentyl claim 53 , neopentyl claim 53 , 1 claim 53 ,1-dimethoxyethyl claim 53 , 1 claim 53 ,1-diethoxyethyl claim 53 , phenyl claim 53 , 4-methoxyphenyl claim 53 , benzyl claim 53 , phenethyl claim 53 , styryl claim 53 , cyclopropyl claim 53 , cyclobutyl claim 53 , cyclopentyl claim 53 , cyclohexyl claim 53 , 2-pyridyl claim 53 , 3-pyridyl and 4-pyridyl.57. The method of claim 53 , wherein Ris selected from methyl claim 53 , ethyl claim 53 , n-propyl claim 53 , isopropyl claim 53 , n-butyl claim 53 , isobutyl claim 53 , sec-butyl claim 53 , tert-butyl claim 53 , n-pentyl claim 53 , isopentyl claim 53 , sec-pentyl claim 53 , neopentyl claim 53 , 1 claim 53 ,1-diethoxyethyl claim 53 , phenyl claim 53 , cyclohexyl and 3-pyridyl.58. ...

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Номер записи: 74
20-06-2019 дата публикации

PRODUCTION METHOD OF CARBAMIC ACID ESTER

Номер: US20190185420A1
Автор: Choi Jun-Chul, Fukaya Norihisa, YASUDA Hiroyuki, Zhang Qiao
Принадлежит:

A method of production of carbamic acid ester has a high yield and high selectivity and is superior in economy. The method of production of a carbamic acid ester includes reacting an amine, carbon dioxide, and an alkoxysilane compound in the presence of a catalyst containing a zinc compound or an alkali metal compound or in the presence of an ionic liquid. A carbamic acid ester is produced, for example by reacting aniline, carbon dioxide, and tetramethoxysilane at a temperature of 150 to 180° C. in the presence of zinc acetate and 2,2′-bipyridine. 1. A method of producing a carbamic acid ester , comprising:reacting an amine, carbon dioxide, and an alkoxysilane compound in the presence of a catalyst containing a zinc compound.2. The method according to claim 1 , wherein the zinc compound is at least one of zinc oxide claim 1 , a zinc halide claim 1 , zinc trifluoromethanesulfonate and zinc acetate.3. The method according to claim 1 , wherein the catalyst further contains a ligand.4. The method of according to claim 3 , wherein the zinc compound is zinc acetate claim 3 , and the ligand is at least one of 1 claim 3 ,10-phenanthroline claim 3 , 2 claim 3 ,2′-bipyridine claim 3 , N claim 3 ,N′-bis(2-pyridylmethyl)ethylenediamine claim 3 , and 1 claim 3 ,4 claim 3 ,8 claim 3 ,11-tetraazacyclotetradecane.5. The method according to claim 1 , wherein the amine claim 1 , the carbon dioxide claim 1 , and the alkoxysilane compound are reacted at a pressure of the carbon dioxide of 3 to 10 MPa.6. A method of producing a carbamic acid ester claim 1 , comprising:reacting an amine, carbon dioxide, and an alkoxysilane compound in the presence of an ionic liquid.7. The method according to claim 6 , wherein an anion of the ionic liquid is at least one of an acetate ion claim 6 , a trifluoroacetate ion claim 6 , and a 2 claim 6 ,2 claim 6 ,2-trifluoroethanol ion.9. The method according to claim 8 , wherein the cation of the ionic liquid is at least one of the compounds represented by ...

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Номер записи: 75
14-07-2016 дата публикации

SYNTHESIS OF BIPHENYLALANINOL VIA NOVEL INTERMEDIATES

Номер: US20160200665A1
Автор: Hanbauer Martin Helmut Friedrich, HERMSEN Petrus Johannes, Zimmermann Axel
Принадлежит:

The invention relates to a novel synthesis route towards R-biphenylalaninol and to the intermediates applied in this synthesis route. The process according to the invention and the intermediate compounds are useful in the synthesis of pharmaceutically active compounds. 2. The process according to claim 1 , wherein the metal borohydride is sodium borohydride.3. The process according to claim 1 , wherein the metal borohydride is activated by a C-Calcohol.4. The process according to claim 3 , wherein the metal borohydride is activated by methanol.5. The process according to claim 1 , wherein the hydrolysis takes place at a temperature between 70° C. and 105° C.8. The process according to claim 7 , wherein the compound according to formula (VI) is further reacted to obtain an active pharmaceutical.12. The process according to claim 11 , wherein the compound according to formula (VI) is further reacted to obtain an active pharmaceutical. The invention relates to a novel synthesis route towards R-biphenylalaninol and to the intermediates applied in this synthesis route. The process according to the invention and the intermediate compounds are useful in the synthesis of pharmaceutically active compounds.The present invention relates to methods to prepare N-boc protected R-biphenylalaninol, which is a key intermediate in the synthesis of pharmaceutically active compounds such as neutral endopeptidase (NEP) inhibitors (see for example U.S. Pat. No. 4,722,810 and EP00509442).The synthesis of R-biphenylalaninol has been described in WO2013/026773A1 (PCT/EP2012/066038) and is depicted in Scheme 1 hereunder.Although the synthesis as described in WO2013/026773A1 is short and economically attractive, the underlying chemical transformations comprising the simultaneous reduction of the ester and amide moiety in the intermediate 3 by lithium aluminum hydride followed by N-debenzylation go along with ecological and safety related disadvantages, comprising the handling of hazardous ...

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Номер записи: 76
30-07-2015 дата публикации

NEW PROCESS

Номер: US20150210632A1
Автор: Li Yunguang, LUO Lijun, Qian Lingfeng, Wei Junhui, YANG Lijun, Ye Wenfa, Zheng Hui, Zhu Guoliang
Принадлежит:

The invention relates to a new enantioselective process for producing useful intermediates for the manufacture of NEP inhibitors or prodrugs thereof, in particular NEP inhibitors comprising a γ-amino-δ-biphenyl-α-methylalkanoic acid, or acid ester, backbone. 2. A process according to claim 1 , wherein said activated biphenylic compound is selected from the group consisting of biphenylmagnesium halide claim 1 , di(biphenyl)magnesium claim 1 , biphenyllithium claim 1 , biphenylcuprate (low and higher-order cuprates) and biphenylzinc.3. A process according to claim 1 , wherein said activated biphenylic compound is biphenylmagnesium halide.4. A process according to claim 1 , wherein the reaction is carried out in the presence of cuprate(I) ions.6. A process according to claim 5 , wherein the reaction with the imide or azide nitrogen nucleophile under Mitsunobu conditions is carried out in the presence of a phosphorous(III) compound claim 5 , and a dialkyl azodicarboxylate.7. A process according to claim 5 , wherein the imide nitrogen nucleophile is selected from the group consisting of succinimide claim 5 , phthalimide claim 5 , substituted succinimide claim 5 , substituted phthalimide claim 5 , naphthalimide claim 5 , substituted naphthalimide claim 5 , maleinimide and substituted maleinimide.13. A process according to claim 12 , wherein the dialkyl azodicarboxylate compound is diethyl azodicarboxylate (DEAD) claim 12 , and the organic solvent is selected from toluene claim 12 , ethyl acetate claim 12 , tetrahydrofurane claim 12 , and dichloromethane.16. A process according to claim 9 , wherein the nitrogen protecting group is tert-butoxy-carbonyl.22. (canceled)23. (canceled)24. (canceled)25. A process for preparing N-(3-carboxyl-1-oxopropyl)-(4S)-(p-phenylphenylmethyl)-4-amino-(2R)-methyl butanoic acid ethyl ester claim 9 , or a salt thereof claim 9 , comprising{'claim-ref': {'@idref': 'CLM-00017', 'claim 17'}, 'i. the manufacture of a compound of formula (3-a) or ...

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Номер записи: 77
29-07-2021 дата публикации

PROCESSES FOR PREPARING (E)-(2-(CHLOROMETHYL)-3-FLUOROALLYL) CARBAMATE COMPOUNDS

Номер: US20210230103A1
Автор: LIM Cheol Hee, SHIN Woo Seob
Принадлежит:

The present technology provides a process for selectively preparing an (E)-(2-(chloromethyl)-3-fluoroallyl)carbamate compound by refluxing an (E/Z)-(2-(chloromethyl)-3-fluoroallyl)carbamate compound in an organic solvent, followed by crystallization by cooling. 2. The method of claim 1 , wherein said organic solvent is hexane claim 1 , heptane claim 1 , a mixed solvent of heptane and methyl ethyl ketone claim 1 , a mixed solvent of heptane and toluene claim 1 , a mixed solvent of heptane and methyl t-butyl ether claim 1 , a mixed solvent of heptane and isopropyl alcohol claim 1 , a mixed solvent of heptane and acetone claim 1 , a mixed solvent of heptane and ethyl acetate claim 1 , a mixed solvent of heptane and tetrahydrofuran claim 1 , a mixed solvent of heptane and methyl isobutyl ketone claim 1 , a mixed solvent of heptane and n-propanol claim 1 , a mixed solvent of heptane and acetonitrile claim 1 , a mixed solvent of heptane and isopropyl acetate claim 1 , a mixed solvent of hexane and methyl ethyl ketone claim 1 , a mixed solvent of hexane and toluene claim 1 , a mixed solvent of hexane and methyl t-butyl ether claim 1 , a mixed solvent of hexane and isopropyl alcohol claim 1 , a mixed solvent of hexane and acetone claim 1 , a mixed solvent of hexane and ethyl acetate claim 1 , a mixed solvent of hexane and tetrahydrofuran claim 1 , a mixed solvent of hexane and methyl isobutyl ketone claim 1 , a mixed solvent of hexane and n-propanol claim 1 , a mixed solvent of hexane and acetonitrile claim 1 , or a mixed solvent of hexane and isopropyl acetate.3. The method of claim 1 , wherein said organic solvent is used in a proportion of 3 mL-7 mL with respect to 1 g of the compound of Formula 1c.4. The method of claim 1 , wherein said refluxing is carried out at a temperature in the range of about 60° C. to about 80° C.5. The method of claim 1 , wherein Step (b) is carried out via crystallization by cooling the reaction mixture to a temperature in a range of about −10 ...

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Номер записи: 78
02-10-2014 дата публикации

SYNTHESIS OF R-BIPHENYLALANINOL

Номер: US20140296559A1
Автор: De Vries Andreas Hendrikus Maria, Ermann Peter Hans, HERMSEN Petrus Johannes, Riebel Peter Hans, Wolberg Michael
Принадлежит:

This invention relates to a novel process for the synthesis of R-biphenylalaninol and to intermediate compounds that are formed in the process according to the invention, i.e. novel intermediates useful in the synthesis of R-biphenylalaninol. The in vention also relates to R-biphenylalaninol, The process according to the invention, the intermediates to of R-biphenylalaninol and of R-biphenylalaninol are all useful in the synthesis of pharmaceutically active compounds. 2. The process of wherein the catalytically active claim 1 , optically active metal complex is formed from a Rh(I) complex and an optically active enentiomerically enriched phosphoramidite monodentate ligand. This invention relates to a novel process for the synthesis of R-biphenylalaninol and to intermediate compounds that are formed in the process according to the invention, i.e. novel intermediates useful in the synthesis of R-biphenylalaninol. The invention also relates to R-biphenylalaninol. The process according to the invention, the intermediates to of R-biphenylalaninol and of R-biphenylalaninol are all useful in the synthesis of pharmaceutically active compounds.The present invention relates to methods to prepare N-Boc protected biphenylalaninol, which is a key intermediate in the synthesis of pharmaceutically active compounds, e.g. neutral endopeptidase (NEP) inhibitors (see e.g.U.S. Pat. No. 4,722,810 and EP00590442.R-biphenylalaninol is a novel compound. However, S-biphenylalaninol is mentioned and used in PCT-application WO9902153 (Table 1, page 25). However, the origin/preparation of this material is not disclosed. The synthesis of the racemic compound is described in CN10120924 (based on information disclosed in English abstract) The route described therein, however, is relatively long and requires an additional resolution step to obtain the desired enantiomerically enriched product. The S-enantiomer of Boc protected biphenyl alaninol has also been reported in patent applications U.S. ...

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Номер записи: 79
16-10-2014 дата публикации

Direct synthesis of 18f-fluoromethoxy compounds for pet imaging and the provision of new precursors for direct radiosynthesis of protected derivatives of o-([18f] fluoromethyl) tyrosine

Номер: US20140309424A1
Автор: Keith Graham, Martin Kruger, Thomas Brumby
Принадлежит: PIRAMAL IMAGING SA

The invention describes novel direct synthesis methods for converting a precursor into a PET-tracer with a 18 F-fluoromethoxy-group. The invention is also directed to novel and stable precursors for the direct radiosynthesis of protected derivatives of O—([ 18 F]Fluoromethyl)tyrosines.

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Номер записи: 80
12-08-2021 дата публикации

PROCESS FOR SYNTHESIS AND PURIFICATION OF (2R,6R)-HYDROXYNORKETAMINE

Номер: US20210246099A1
Автор: Bourne Samuel Lawrence, Castledine Richard Andrew, Morris Patrick Joseph, Thomas Craig J.
Принадлежит:

A process for the preparation of (2R, 6R)-hydroxynorketamine is provided. The process requires no chromatography purification and affords the (2R, 6R)-hydroxynorketamine in eight steps with a 26% overall yield and greater than 97% purity. 8. The process according to claim 7 , wherein the oxidizing agent is meta-chloroperoxybenzoic acid.12. The process according to claim 1 , wherein the purity of the (2R claim 1 ,6R)-hydroxynorketamine hydrochloride is 97% or greater.14. The process according to claim 13 , wherein the ammonia source is liquid ammonia.16. The process according to claim 15 , wherein the brominating source is molecular bromine.19. The process according to claim 17 , wherein the purity of the (2R claim 17 ,6R)-hydroxynorketamine hydrochloride after Step (h) is 97% or greater.20. The process according to claim 17 , wherein none of Step (a) to Step (h) requires chromatography purification. This application claims priority to and the benefit of U.S. Provisional Application No. 62/680,183 filed on Jun. 4, 2018, which is hereby incorporated by reference in its entirety.The present invention is directed to a synthesis of a therapeutic agent for curing treatment-resistant depression, and more specifically, to an improved process for synthesis and purification of (2R,6R)-hydroxynorketamine.Depression is a mood disorder affecting millions of people worldwide, which is characterized by a persistent feeling of sadness and loss of interest. Depression is caused by a combination of biological, psychological, and social sources of distress, which results in changes in brain function, including altered activity of certain neural circuits in the brain. Various therapeutic agents, known as antidepressants, have been proposed and developed to treat depression. However, as many as two-thirds of people with the disease are not helped with the first antidepressant they try.Recently, (2R,6R)-hydroxynorketamine was discovered as a leading compound for curing treatment- ...

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Номер записи: 81
19-08-2021 дата публикации

METHOD FOR PRODUCING AMINO ACID AMINOALKYL ESTER OR INORGANIC ACID SALT THEREOF

Номер: US20210253517A1
Автор: Miyake Nobuhisa, NAKAOKA Koichi, Shinohata Masaaki, TAKAGAKI Kazuhiro, UEMATSU Tsubasa
Принадлежит: ASAHI KASEI KABUSHIKI KAISHA

The present invention provides a method for producing an amino acid aminoalkyl ester or an inorganic acid salt thereof by reacting a compound represented by general formula (I) shown below or a compound represented by general formula (III) shown below, or a salt thereof, and at least one compound selected from the group consisting of compounds represented by general formula (IV-I) shown below, compounds represented by general formula (IV-II) shown below, compounds represented by general formula (IV-III) shown below and compounds represented by general formula (IV-IV) shown below, or an inorganic acid salt thereof. 2. The method according to claim 1 , wherein the reaction is conducted in presence of at least one acid catalyst selected from the group consisting of organic acids and inorganic acids having a normal boiling point of 0° C. or higher.3. The method according to claim 1 , wherein the compound represented by the general formula (I) is at least one amino acid selected from the group consisting of lysine claim 1 , glutamic acid claim 1 , methionine claim 1 , glycine claim 1 , phenylalanine claim 1 , asparagine claim 1 , alanine claim 1 , leucine claim 1 , isoleucine claim 1 , and valine.4. The method according to claim 2 , wherein the inorganic acid used as an acid catalyst is at least one acid selected from the group consisting of sulfuric acid claim 2 , phosphoric acid claim 2 , nitric acid and boric acid.5. The method according to claim 2 , wherein an acid that forms a salt with the compound represented by general formula (I) or the compound represented by general formula (III) and the acid catalyst are the same acid.6. The method according to claim 1 , whereinin the general formula (I):the substituent is at least one group selected from the group consisting of monovalent aliphatic hydrocarbon groups of at least 1 but not more than 10 carbon atoms, monovalent aromatic cyclic groups of at least 6 but not more than 10 carbon atoms, groups represented by the ...

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Номер записи: 82
16-07-2020 дата публикации

MANUFACTURE OF 4,5,6,7-TETRAHYDROISOXAZOLO[5,4-C]PYRIDIN-3-OL

Номер: US20200223865A1
Автор: DE FAVERI Carla, Huber Florian Anton Martin
Принадлежит:

The present invention relates to a process for synthesis of 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3-ol abbreviated THIP, having the INN name gaboxadol, starting from pyrrolidin-2-one. The process comprises a new direct process to obtain the intermediate dimethyl 5-hydroxy-3,6-dihydropyridine-1,4(2H)-dicarboxylate or the intermediate diethyl 5-hydroxy-3,6-dihydropyridine-1,4(2H)-dicarboxylate. 4. The process according to claim 3 , wherein steps (b) claim 3 , (c) and (d) are carried out in toluene.5. The process according to claim 3 , wherein the base used in step (b) is triethylamine.6. The process according to claim 3 , wherein the compound of formula V is purified by thin-film distillation.7. The process according to claim 3 , wherein the compound of formula V is purified by washing with acidified water or by distillation or by a combination of these two purification strategies.9. The process according to claim 8 , wherein the anhydrous acid is anhydrous methanesulfonic acid.11. The process according to claim 10 , wherein the compound of formula IIb is obtained by a one-pot synthesis.14. The process according to claim 13 , further comprising the step of converting the compound of formula VIII to the compound of formula IX. This application is a divisional of U.S. application Ser. No. 15/559,630, (filed Sep. 19, 2017); which is a § 371 national stage entry of PCT/EP2016/056244 (filed on Mar. 22, 2016); which application claims priority to Danish Patent Application PA 2015 00181 (filed on Mar. 24, 2015), each of which applications is incorporated herein by reference in their entirety.The present invention relates to a process for synthesis of 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3-ol abbreviated THIP, having the INN name gaboxadol, starting from pyrrolidin-2-one. The process comprises a new direct process to obtain the intermediate dimethyl 5-hydroxy-3,6-dihydropyridine-1,4(2H)-dicarboxylate or the intermediate diethyl 5-hydroxy-3,6-dihydropyridine-1,4(2H)- ...

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Номер записи: 83
25-08-2016 дата публикации

Heterocyclic Coupling Catalysts and Methods Related Thereto

Номер: US20160243534A1
Автор: Gangireddy Pavan Kumar Reddy, Liebeskind Lanny S., Lindale Matthew
Принадлежит: EMORY UNIVERSITY

This disclosure relates to synthetic coupling methods using a catalytic molecule comprising two bonded atoms wherein one atom is an amide nitrogen and the second atom is not nitrogen or carbon, such as sulfur, such as a sufur amide nitrogen bond, typically in a heterocycle, such as substituted benzoisothiazolones and derivatives thereof, as a catalyst in the transformation of hydroxy group containing compounds to amides, esters, ketones, and other carbon to heteroatom or carbon to carbon transformations. 1. A method of catalyzing a coupling reaction comprising mixinga) a compound comprising a hydroxy group,b) a trisubstituted phosphite,c) a nucleophile, andd) a catalytic heterocycle comprising two bonded heteroatoms wherein one heteroatom is a nitrogen and the second heteroatom is not nitrogen,under conditions such that a compound is formed comprising the nucleophile in place of the hydroxy group.2. The method of claim 1 , wherein mixing includes a copper.3. The method of claim 1 , wherein the trisubstituted phosphite is trialkylphosphite selected from trimethylphosphite claim 1 , triethylphosphite claim 1 , tripropylphosphite claim 1 , triisopropylphosphite claim 1 , tributyl phosphite claim 1 , and tert-butylphoshpite.4. The method of claim 1 , wherein mixing is done under conditions such that an amide claim 1 , an amine claim 1 , an ester claim 1 , an ether claim 1 , a ketone claim 1 , or other carbon to carbon bond is formed.5. The method of claim 1 , wherein the compound comprising a hydroxy group is primary or secondary alcohol or a carboxylic acid.6. The method of claim 1 , wherein the nucleophile comprising a hydrogen group is a primary or secondary amine claim 1 , or primary or secondary alcohol claim 1 , or boronic acid.7. The method of claim 1 , wherein the catalytic heterocycle is benzoisothiazolone.8. The method of claim 1 , wherein the catalystic heterocycle linked through a linking group to a silicate claim 1 , glass claim 1 , polymer claim 1 , metal ...

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Номер записи: 84
23-08-2018 дата публикации

Process for the Synthesis of Melphalan and the Hydrochloride Salt

Номер: US20180237377A1
Автор: Jagadeesh Babu Rangisetty, Madhava Reddy VEDURURI, Manik Reddy Pullagurla, Mecheril Valsan Nandakumar, Sreenu SAMIREDDI
Принадлежит: Biophore India Pharmaceuticals Pvt Ltd

The present invention relates to an improved process for the preparation of Melphalan, more specifically the invention relates to an efficient process for the preparation of substantially pure Melphalan hydrochloride (I).

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Номер записи: 85
23-08-2018 дата публикации

3-PHENYLISOSERINE DERIVATIVE PRODUCTION METHOD

Номер: US20180237384A1
Автор: HIRAGA Hisafumi, Nishikawa Takeshi
Принадлежит:

A method produces a 3-phenylisoserine derivative by protecting an amino group of a compound represented by General Formula (1) (wherein Rrepresents a phenyl group, or a phenyl group having a substituent; Rrepresents an alkali metal, alkaline earth metal, or nitrogen base; and Rrepresents a hydrogen atom, methyl group, benzyl group, p-methoxybenzyl group, tert-butyl group, methoxymethyl group, 2-tetrahydropyranyl group, ethoxyethyl group, acetyl group, pivaloyl group, benzoyl group, trimethylsilyl group, triethylsilyl group, or tert-butyldimethylsilyl group) in water or a mixed solvent containing water to obtain a particular compound; extracting with a Cether-based solvent; replacing at least part of the Cether-based solvent with a C-Caliphatic alcohol while removing the Cether-based solvent and water to perform esterification reaction; and isolating at 0 to 30° C. to obtain a 3-phenylisoserine derivative represented by General Formula (2). 14.-. (canceled)6. The method according to claim 5 , wherein the Cether-based solvent is tetrahydrofuran or 1 claim 5 ,2-dimethoxyethane.7. The method according to claim 5 , wherein the C-Caliphatic alcohol is methanol or ethanol.8. The method according to claim 5 , wherein Ris a benzoyl group or tert-butoxycarbonyl group.9. The method according to claim 6 , wherein the C-Caliphatic alcohol is methanol or ethanol.10. The method according to claim 6 , wherein Ris a benzoyl group or tert-butoxycarbonyl group.11. The method according to claim 7 , wherein Ris a benzoyl group or tert-butoxycarbonyl group. This disclosure relates to a method of producing a 3-phenylisoserine derivative, which is important as, for example, an intermediate material for pharmaceuticals.Compounds having a β-amino acid site such as 3-phenylisoserine derivatives are known to be compounds that are industrially useful for pharmaceuticals and the like. Known examples of methods of producing a 3-phenylisoserine derivative include the following:(1) a method in ...

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Номер записи: 86
10-09-2015 дата публикации

NICKEL FLUORINATING COMPLEXES AND USES THEREOF

Номер: US20150252067A1
Автор: Lee Eunsung, Ritter Tobias
Принадлежит: President and Fellows of Harvard College

The present invention provides novel nickel complexes. These complexes are in providing fluorinating organic compounds. The invention is particularly useful for fluorinating compounds with F for PET imaging. 2. The method of claim 1 , wherein the source of fluorine is a fluoride source comprising water or a fluorinating agent.3. The method of claim 1 , wherein source of fluorine comprises F or F.45-. (canceled)7. The method of claim 6 , wherein Ais aryl substituted with o occurrences of R.9. The method of claim 8 , wherein Ais heteroaryl substituted with p occurrences of R.12. The method of claim 1 , wherein S is an optionally substituted aryl comprising substrate claim 1 , an optionally substituted heteoaryl or an optionally substituted Calkenyl.18. The method of claim 1 , wherein the method further comprises adding a salt to the source of fluorine.19. The method of claim 1 , wherein the method further comprises adding a salt to the nickel comprising complex.20. The method of claim 1 , wherein the method further comprises including a salt in the mixture containing the nickel comprising complex and source of fluorine.2127-. (canceled)3033-. (canceled) The present application claims priority under 35 U.S.C. §119(e) to U.S. provisional patent applications, U.S. Ser. No. 61/705,980, filed Sep. 26, 2013, and U.S. Ser. No. 61/782,119, filed Mar. 14, 2013, the entire contents of each of which are incorporated herein by reference.This invention was made with government support under EB013042 awarded by the National Institutes of Health. The government has certain rights in the invention.The regioselective fluorination of organic compounds is an important challenge in the synthesis of pharmaceuticals and agrochemicals (see, for example, Muller et al., 2007, 317, 1881-1886; Park et al., 2001, 41, 443-470; Bohm et al., 2004, 5, 637-643; and Jeschke, 2004, 5, 570-589).Syntheses of simple fluoroarenes currently rely on the pyrolysis of diazonium tetrafluoroborates (Balz, G.; ...

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Номер записи: 87
09-09-2021 дата публикации

SYNTHESIS OF 4-CHLOROKYNURENINES AND INTERMEDIATES

Номер: US20210276942A1
Автор: Eisenreich Emerich, Leeming Peter, Levin Daniel, LIU Xuejun Karl
Принадлежит:

The invention relates to an overall enantio-specific synthesis of 4-chlorokynurenine compounds, in particular L-4-chlorokynurenine, with improved yields. Large-scale syntheses are disclosed. The invention also relates to novel intermediates in the synthesis of L-4-chlorokynurenine. 2. A method of claim 1 , further comprising at least one of the following:in Step 1, the presence of a catalytic amount of 4-dimethylaminopyridine and, optionally isolating and recrystallizing the tosylate (2);in Step 2, an aqueous quench of the reaction mixture into water to precipitate the iodo intermediate (3) and, optionally, recrystallization of the iodo intermediate (3);in Step 3, the palladium (0) catalyst [Pd] is Pd(0) tetrakis and with a CO pressure ranging from 1 psig to 1,000 psig; andin Step 4, deprotecting the protected ester compound (6) to remove any protecting group PG using HCl in dioxane and isolating the ester (7) in the absence of light without exposure to air or moisture and, in a separate deprotection step, hydrolyzing (7) at a pH of 12.0 to 12.5 to form 4-chlorokynurenine (8) after adjustment to an acidic pH.3. A method of claim 1 , further comprising the steps of:as the pH adjustment, isolating the 4-chlorokynurenine (8) from alkaline solution as a fee acid with aqueous acid to a pH below 6.5,dissolving the isolated free acid (8) in aqueous acid at a pH below 2,precipitating the free acid (8) by adjusting the pH of 4.5 to 6.5,collecting the precipitated free acid (8),drying the collected free acid (8), andoptionally, triturating the collected free acid (8) using an organic solvent or an organic solvent mixture and drying the triturated free acid (8).4. A method of claim 1 , wherein{'sub': 1', '6, 'R is a C-Calkyl group;'}PG is an amine protecting group selected from BOC, Fmoc, Benzyl, Benzoyl, alkylamine, arylamine, TFA, and CBz; andX is I.5. A method of claim 4 , whereinR is a methyl group,PG is the amino protecting group BOC, andX is I.7. A method of claim 6 , ...

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Номер записи: 88
24-09-2015 дата публикации

Double caged gaba compounds, bis-cnb-gaba

Номер: US20150266809A1
Автор: Diana Shi, Martin Semmelhack, Samuel WANG
Принадлежит: PRINCETON UNIVERSITY

Double caged GABA compounds and compositions including the same are described. Methods of synthesizing and using double caged GABA compounds are provided.

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Номер записи: 89
24-09-2015 дата публикации

FLEXIBLE TO RIGID NANOPOROUS POLYURETHANE-ACRYLATE (PUAC) TYPE MATERIALS FOR STRUCTURAL AND THERMAL INSULATION APPLICATIONS

Номер: US20150266983A1
Автор: Bang Abhishek, Leventis Nicholas, Sotiriou-Leventis Chariklia
Принадлежит: The Curators of the University of Missouri

Novel urethane-acrylate (UAC) Star monomers and polyurethane-acrylate (PUAC) aerogel polymers derived therefrom are described herein, along with other novel, related monomers and polymers. Also described herein are processes for preparing the UAC Star monomers, the PUAC aerogel polymers, and the other related monomers and polymers. The PUAC and related polymers herein are useful in various applications including in structural and thermal insulation. 2. The urethane-acrylate star monomer of wherein the nitrogen atoms of the urethane moieties are attached to their respective aryl rings at the 4-positions of the aryl rings.3. The urethane-acrylate star monomer of wherein W═X═Y═CHCH.4. The urethane-acrylate star monomer of wherein each of R1-R9 is a hydrogen.5. The urethane-acrylate star monomer of wherein the nitrogen atoms of the urethane moieties are attached to their respective aryl rings at the 4-positions of the aryl rings; wherein W═X═Y═CHCH; and wherein each of R1-R9 is a hydrogen.6. A polyurethane-acrylate polymer formed by the polymerization of the urethane-acrylate star monomer of in the presence of a polymerization catalyst.7. The polyurethane-acrylate polymer of claim 6 , wherein the polymerization catalyst is a free radical initiator.8. The polyurethane-acrylate polymer of claim 7 , wherein the free radical initiator is 2 claim 7 ,2′-azobisisobutyronitrile.9. A polyurethane-acrylate polymer formed by the copolymerization of the urethane-acrylate star monomer of with a polymerization chain extender claim 1 , in the presence of a polymerization catalyst.10. The polyurethane-acrylate polymer of claim 9 , wherein the polymerization chain extender is a compound comprising from 2 to 4 acrylate groups or from 2 to 4 methacrylate groups claim 9 , or a combination thereof.11. The polyurethane-acrylate polymer of claim 10 , wherein the chain extender is a compound comprising 2 acrylate groups.15. The polyurethane-acrylate polymer of wherein the nitrogen atoms of the ...

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Номер записи: 90
27-11-2014 дата публикации

NOVEL POLYMORPHS OF N-[2-AMINO-4-(4-FLUOROBENZYLAMINO)-PHENYL] CARBAMIC ACID ETHYL ESTER AND PROCESSES THEREOF

Номер: US20140350285A1
Автор: Haritha Kirla, Mohan Rao Dodda
Принадлежит: SYMED LABS LIMITED

The present invention relates to novel polymorphs of N-[2-amino-4-(4-fluorobenzylamino)-phenyl]carbamic acid ethyl ester, processes for preparing them, and pharmaceutical composition comprising them. In one aspect, the present invention relates to a novel crystalline polymorph of retigabine designated as crystalline Form I, characterized by XRPD having characteristic peaks at about 4.87, 5.04, 7.03, 9.74, 10.02, 11.6, 18.03, 19.9 and 28.5±0.2 degrees two-theta, which is substantially same as depicted in FIG. 114-. (canceled)15. Crystalline Form II of retigabine characterized by an X-ray powder diffraction (XRPD) pattern having characteristic 2-theta peaks at about 5.07 , 10.09 , 14.86 , 15.1 and 30.4±0.2 degrees substantially in accordance with .16. (canceled)17. The crystalline Form II of claim 15 , which is further characterized by an FT-IR spectrum having main bands at about 694 claim 15 , 734 claim 15 , 765 claim 15 , 789 claim 15 , 827 claim 15 , 837 claim 15 , 860 claim 15 , 907 claim 15 , 937 claim 15 , 979 claim 15 , 1014 claim 15 , 1066 claim 15 , 1096 claim 15 , 1155 claim 15 , 1173 claim 15 , 1223 claim 15 , 1259 claim 15 , 1295 claim 15 , 1345 claim 15 , 1367 claim 15 , 1391 claim 15 , 1428 claim 15 , 1474 claim 15 , 1509 claim 15 , 1536 claim 15 , 1600 claim 15 , 1628 claim 15 , 1679 claim 15 , 1709 claim 15 , 1890 claim 15 , 2850 claim 15 , 2873 claim 15 , 2906 claim 15 , 2959 claim 15 , 2985 claim 15 , 3040 claim 15 , 3283 claim 15 , 3346 claim 15 , 3395 and 3442±2 cmsubstantially in accordance with .18. The crystalline Form II of claim 15 , which is further characterized by differential scanning calorimetric (DSC) thermogram having an endotherm curve at about 141.23° C. with an onset at about 140.48° C. substantially in accordance with .19. The crystalline Form II of claim 15 , which is further characterized by FT-RAMAN spectra having peaks at about 60 claim 15 , 139 claim 15 , 243 claim 15 , 338 claim 15 , 369 claim 15 , 400 claim 15 , 466 claim 15 ...

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Номер записи: 91
13-09-2018 дата публикации

STEREOSELECTIVE PROCESS

Номер: US20180258031A1
Автор: HADDAD Nizar, QU Bo, RIES Uwe Joerg
Принадлежит:

The invention relates to a method for the stereoselective preparation of compounds of formula (IV). 4. The method according to claim 1 , wherein step (C) is carried out at a temperature from 0° C. to −70° C.5. The method according to claim 1 , wherein step (C) is carried out in a solvent selected from the group consisting of ethyl acetate claim 1 , Me-THF claim 1 , THF claim 1 , dichloromethane claim 1 , isopropyl acetate claim 1 , n-butyl acetate claim 1 , toluene and DMF.6. The method according to claim 1 , wherein step (C) is carried out using from 0.3 mol % to 10 mol % of the organo-catalyst of formula (X).7. The method according to claim 1 , wherein step (C) is carried out using from 1.0 to 1.5 molar equivalents of the compound of formula (I).8. The method according to claim 1 , wherein step (C) is carried out using 1.0. molar equivalents of compound of formula (III).10. (canceled)11. (canceled) The invention relates to a method for the stereoselective preparation of compounds of formula (IV)WO2014/122160 describes substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity. Intermediates described therein are of the type of formula (IV). Single enantiomers of compounds described therein are obtained by preparative chromatography on a chiral phase.The problem of the present invention is to provide a stereoselective process for preparing compounds of formula (IV).Terms not specifically defined herein should be given the meanings that would be given to them by one of skill in the art in light of the disclosure and the context. As used in the specification, however, unless specified to the contrary, the following terms have the meaning indicated and the following conventions are adhered to.In the groups, radicals, or moieties defined below, the number of carbon atoms is often specified preceding the group, for example, C-alkyl means an alkyl group or radical having 1 to 6 carbon atoms.In general in single groups like HO, ...

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Номер записи: 92
13-09-2018 дата публикации

ACYLOXYALKYL CARBAMATE PRODRUGS, METHODS OF SYNTHESIS AND USE

Номер: US20180258032A1
Автор: Gallop Mark A., Ludwikow Maria J., Peng Ge, Phan Thu, Yao Fenmei
Принадлежит:

The disclosures herein relate generally to acyloxyalkyl carbamate prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof, pharmaceutical compositions thereof, methods of making prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof, methods of using prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof, and pharmaceutical compositions thereof for treating or preventing common diseases and/or disorders such as spasticity and/or acid reflux disease. The disclosures herein also relate to acyloxyalkyl carbamate prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof which are suitable for oral administration and to sustained release oral dosage forms thereof. 152-. (canceled)54. The method of claim 53 , wherein Rand Rin the compound of Formula (XXIII) are different claim 53 , such that the carbon atom to which these substitutents are attached is a stereogenic center.55. The method of claim 53 , wherein Ris isopropyl claim 53 , Ris isopropyl claim 53 , Ris hydrogen claim 53 , the stereochemistry at the carbon to which Rand Rare attached is of the S-configuration and the compound of Formula (I) is substantially one diastereomer.56. The method of claim 53 , wherein Ris isopropyl claim 53 , Ris isopropyl claim 53 , Ris hydrogen claim 53 , the stereochemistry at the carbon to which Rand Rare attached is of the R-configuration and the compound of Formula (I) is substantially one diastereomer.55. The method of claim 53 , wherein Ris isopropyl claim 53 , Ris isopropyl claim 53 , Ris hydrogen claim 53 , Ris hydrogen claim 53 , Ris 4-chlorophenyl claim 53 , Ris hydrogen and Ris hydrogen.56. The method of claim 53 , wherein the method is carried out at a temperature between about −20° C. and about 40° C.57. The method of claim 53 , wherein the method is performed in the absence of a base.58. The method of claim 53 , wherein the method is performed in the presence of an inorganic base.59. The method ...

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Номер записи: 93
01-10-2015 дата публикации

PROCESS FOR THE PREPARATION OF INTERMEDIATES USEFUL FOR THE MANUFACTURE NEP INHIBITORS

Номер: US20150274650A1
Автор: Bappert Erhard, Hook David, Li Yunzhong, Riss Bernhard, ZHOU Jianguang
Принадлежит:

The invention relates to a new process for producing useful intermediates for the manufacture of NEP inhibitors or prodrugs thereof, in particular NEP inhibitors comprising a γ-amino-δ-biphenyl-α-methylalkanoic acid, or acid ester, backbone, such as N-(3-carboxyl-1-oxopropyl)-(4S)-(p-phenylphenylmethyl)-4-amino-(2R)-methyl butanoic acid ethyl ester or salt thereof. 2. The compound of formula (5) according to whereinR1 is hydrogen;R2 is BOC or hydrogen; andR is hydrogen.3. The compound of formula (5) according to which is (Z)—(R)-5-Biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpent-2-enoic acid claim 2 , or (Z)—(R)-4-Amino-5-biphenyl-4-yl-2-methyl-pent-2-enoic acid hydrochloride.8. A process according to claim 7 , wherein the reduction reaction is carried out with hydrogen in the presence of a transition metal catalyst which comprises an organometallic complex and a chiral ligand or which is an organometallic catalyst.9. A process according to claim 8 , wherein the transition metal catalyst comprises(i) an organometallic complex and a chiral ligand, wherein{'sub': 2', '3', '3', '2', '4, 'a) the organometallic complex is a rhodium organometallic complex selected from [Rh(cod)]OSCFand [Rh(nbd)]BFand the chiral ligand is selected from SL-A101-2, SL-A109-2, SL-A241-1, (R,R)-MOD-DIOP, (R)-PhanePhos, SL-F356-1, SL-J003-1, SL-J005-2, SL-J216-1, SL-J302-1, SL-M001-1, SL-M002-2, SL-M003-1, SL-T001-1, SL-T002-1 and SL-W008-1; or'}{'sub': 3', '2, 'b) the organometallic complex is the ruthenium organometallic complex [Ru(cod)(OOCCF)] and the chiral ligand is selected from (R)-PhanePhos and SL-M002-2, or'}c) the organometallic complex is a rhodium organometallic complex and the chiral ligand is SL-A242-1, ord) the organometallic complex is a ruthenium organometallic complex, and the chiral ligand is selected from SL-A242-1 or (R,R)-BDPP, or{'sub': 4', '4', '3', '3, '(ii) an organometallic catalyst selected from [Rh(cod)(SL-P005-1)]BF, [Rh(cod)(SL-P114-1)]BF, [Rh(cod)(SL-P102-1 ...

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Номер записи: 94
22-08-2019 дата публикации

Methods and intermediates for synthesizing sk1-i

Номер: US20190256453A1
Автор: Natarajan Raju, Praveen Pande, Zaiguo Li
Принадлежит: Enzo Biochem Inc

The invention provides methods for synthesizing the compound (2R,3S,4E)-N-methyl-5-(4′-pentylphenyl)-2-aminopent-4-ene-1,3-diol, also known as SK1-I, and intermediate compounds used in its synthesis.

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Номер записи: 95
21-09-2017 дата публикации

Integrated process for capturing carbon dioxide

Номер: US20170267538A1
Автор: Ethan NOVEK
Принадлежит: Individual

The invention pertains to an integrated process for capturing CO 2 . The process involves desorbing gaseous CO 2 from a CO 2 containing aqueous solution comprising carbonate, bicarbonate, sesquicarbonate, carbamate, or a mixture thereof. The desorbing of gaseous CO 2 is conducted in the presence of a suitable water soluble substance. If desired, the process may also at least partially recover the soluble substance using a membrane, distillation, or another technique.

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Номер записи: 96
21-09-2017 дата публикации

INTEGRATED PROCESS FOR CARBON CAPTURE AND ENERGY PRODUCTION

Номер: US20170267539A1
Автор: Novek Ethan
Принадлежит:

The present invention pertains to new methods for generating energy and useful nitrogen compounds from captured carbon dioxide. It involves employing an osmotic engine, draw solution, and feed solution. An osmotic gradient between the solutions assists in generating energy and a solution of ammonium carbonate, ammonium bicarbonate or mixture thereof. This solution may be decomposed to form ammonia, carbon dioxide, a precipitate, or a mixture thereof.

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Номер записи: 97
20-08-2020 дата публикации

DEUTERATED FORMS OF AMINOSTEROLS AND METHODS OF USING THE SAME

Номер: US20200262864A1
Автор: Ashford Scott, BARBUT DENISE, Bieliauskas Anton, Fevig Tom, Hessler Edward, JONES Stephen, Karnes Harold, Kinney William A., Zasloff Michael
Принадлежит: Enterin, Inc.

Described are deuterated forms of aminosterols, or a pharmaceutically acceptable salt thereof, wherein one or more hydrogen atoms at one or more positions selected from C1, C2, C3, C4, C5, C6, C7, C8, C9, C11, C12, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, and C27, are replaced with deuterium. 2. The compound of claim 1 , or a pharmaceutically acceptable salt thereof claim 1 , wherein:(a) one or more hydrogen atoms at one or more positions selected from C2, C3, C4, C5, C6, C7, C8, C22, C23, C24, C25, C26, and C27, are replaced with deuterium; and/or(b) one or more hydrogen atoms at one or more positions selected from C3, C4, C5, C6, C7, C22, C23, C24, C25, C26, and C27, are replaced with deuterium; and/or(c) one or more hydrogen atoms at one or more positions selected from C4, C5, C7, C22, C23, C24, C25, C26, and C27, are replaced with deuterium; and/or(d) one or more hydrogen atoms at one or more positions selected from C1, C2, C3, C4, C5, C6, C7, C8, C11, C12, C16, C17, C18, C19, C20, and C21 are replaced with deuterium; and/or(e) all hydrogen atoms at positions C25, C26, and C27 are replaced with deuterium; and/or(f) all hydrogen atoms at positions C26 and C27 are replaced with deuterium.3. The compound of claim 1 , wherein:(a) any atom not designated as deuterium is present at its natural isotopic abundance; and/or(b) the deuterium incorporation at each designated deuterium atom is at least about 90%; and/or(c) the deuterium incorporation at each designated deuterium atom is at least about 95%; and/or(d) the deuterium incorporation at each designated deuterium atom is at least about 97%.4. The compound of claim 1 , wherein:(a) the compound has an isotopic enrichment factor selected from the group consisting of at least about 3500, at least about 4000, at least about 4500, at least about 5000, at least about 5500, at least about 6000, at least about 6333.3, at least about 6466.7, at least about 6600, and at least about 6633.3; and/or(b) the ...

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Номер записи: 98
27-08-2020 дата публикации

POTENT INHIBITORS OF ASPARTATE N-ACETYL-TRANSFERASE FOR THE TREATMENT OF CANAVAN DISEASE

Номер: US20200270202A1
Автор: Mutthamsetty Vinay, Thangavelu Bharani, Viola Ronald E., Wang Qinzhe
Принадлежит: The University of Toledo

Compounds, compositions, and methods for the treatment of Canavan disease are described. 2. The compound of claim 1 , wherein the compound comprises Formula I claim 1 , and n is 1 or 2.3. The compound of claim 1 , wherein the compound comprises Formula II claim 1 , and n is 1.4. The compound of claim 1 , wherein R comprises a phenyl group claim 1 , an ester claim 1 , a butyl ester claim 1 , a phenyl ester claim 1 , a trifluoromethyl substituted phenyl claim 1 , or a tert-butyl substituted phenyl.5. (canceled)6. (canceled)7. (canceled)8. (canceled)9. (canceled)10. The compound of claim 1 , wherein R is 3 claim 1 ,5-(trifluoromethyl)benzene.15. The compound of claim 1 , wherein the compound is selected from the group consisting of: N-carbobenzyloxy-L-glutamic acid claim 1 , N-(1-oxo-3-phenylpropyl)-L-aspartic acid claim 1 , N-[(benzyloxy)carbonyl]-L-aspartic acid claim 1 , N-chloroacetyl-L-aspartic acid claim 1 , N-(t-butoxycarbonyl)-L-aspartic acid claim 1 , N-[(4-methylphenyl)sulfonyl]-L-proline claim 1 , N-methyl-DL-aspartic acid claim 1 , N-alanyl-L-aspartic acid claim 1 , 2-(3-chloro-6-oxopyridazin-1(6H)-yl)acetic acid claim 1 , isoxazole-3-carboxylic acid claim 1 , and benzo[d]isoxazole-3-carboxylic acid.21. A pharmaceutical composition comprising:{'claim-ref': {'@idref': 'CLM-00001', 'claim 1'}, 'an effective amount of a compound of ; and'}a pharmaceutically acceptable carrier, diluent, or adjuvant.22. A method of making a compound of claim 1 , the method comprising:reacting a hydrochloride dimethylester with either a halide or an acid to produce an N-acyl derivative dimethylester; and{'claim-ref': {'@idref': 'CLM-00001', 'claim 1'}, 'hydrolyzing the N-acyl derivative dimethylester to produce a compound of .'}23. The method of claim 22 , wherein the hydrochloride dimethylester is produced by reacting thionyl chloride with one of aminomalonate claim 22 , aminoaspartate claim 22 , amino glutamate claim 22 , or 2-aminoadipate.24. A method of making a compound of ...

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Номер записи: 99
12-10-2017 дата публикации

SUBSTITUTED 5-HYDROXY-2-PHENYL-3-HETEROARYL PENTANENITRILE DERIVATES, METHOD FOR THE PRODUCTION THEREOF AND USE THEREOF AS HERBICIDES AND/OR PLANT GROWH REGULATORS

Номер: US20170290330A1
Автор: Dietrich Hansjoerg, GATZWEILER ELMAR, Jakobi Harald, MOSRIN Marc, ROSINGER CHRISTOPHER HUGH, SCHMUTZLER Dirk
Принадлежит:

Primarily, the present invention relates to compounds of the formula (I) defined below and to their use as herbicides, in particular for controlling broad-leaved weeds and/or weed grasses in crops of useful plants and/or as plant growth regulators for influencing the growth of crops of useful plants. The present invention also relates to herbicidal or plant growth-regulating compositions comprising one or more compounds of the formula (I). Moreover, the present invention relates to processes for preparing the compounds of the formula (I). 2. The compound of the formula (I) and/or salt thereof according to claim 1 , whereinQ represents a mono- or bicyclic heteroaromatic radical having in total 2 to 9 carbon ring atoms, where the heteroaromatic radical Q contains 1, 2, 3 or 4 heteroatoms in the heteroaromatic ring and the heteroatom or the heteroatoms are selected from the group consisting of N, O, and S.3. The compound of the formula (I) and/or salt thereof as claimed in claim 1 , whereinQ represents a mono- or bicyclic heteroaromatic radical selected from the group consisting of pyrimidinyl, pyridinyl, pyridazinyl, pyrazinyl, thienyl, furyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, triazinyl, quinolyl, isoquinolyl, cinnolinyl-, quinazolinyl, quinoxalinyl, pteridinyl, indolyl and phthalazinyl.5. The compound of the formula (I) and/or salt thereof as claimed in claim 1 , wherein{'sup': '1', 'Rrepresents hydrogen or a hydrolyzable radical having in total up to 30 carbon atoms, with preference a hydrolyzable radical having in total 1 to 24 carbon atoms, preferably optionally having in total 1 to 20 carbon atoms.'}6. The compound of the formula (I) and/or salt thereof as claimed in claim 1 , wherein{'sup': 1', '1, 'claim-text': represents an optionally substituted hydrocarbon radical or an optionally substituted heterocyclyl radical, or', {'sup': a', 'b', 'c', 'a', 'b, 'represents a radical of the formula SiRRR, or —NRR,'}], 'Rrepresents hydrogen or a hydrolyzable ...

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Номер записи: 100