Sphingosine kinase type 1 inhibitors, and processes for using same

Provided are novel compositions and analogs which are useful in a number of applications, indications and diseases, as well as for monitoring pharmakinetics and patient management. These compounds and analogs are applicable to treating tumors of the central nervous system, e.g., glioblastoma (GBM).

CHROMENE DERIVATIVES

Derivates of chromene of formula I, where the meanings for the various substituents are as indicated in the description. These compounds are useful as inhibitors of TCR-Nck interaction in T lymphocytes. 2. The compound according to where each Rand Rindependently represent hydrogen claim 1 , Calkyl claim 1 , haloCalkyl claim 1 , Calkoxyl claim 1 , halogen or Cy.3. The compound according to where each Rindependently represents hydrogen claim 1 , Calkoxyl or Cy.4. The compound according to where each Rindependently represents Calkyl claim 1 , haloCalkyl or halogen claim 1 , preferably haloCalkyl or halogen.5. The compound according to where Rrepresents hydrogen.6. The compound according to where Cyrepresents a monocyclic heterocycle of 5 or 6 members claim 1 , saturated or partially unsaturated which is merged with the rest of the molecule by any available N atom claim 1 , where Cymay contain 1 or 2 heteroatoms selected from N claim 1 , O and S claim 1 , where one or more C or S atoms of the ring can be oxidized to form groups CO claim 1 , SO or SO claim 1 , and where Cyis optionally replaced by one or more R.9. The compound according to i where each Cyindependently represents phenyl or an aromatic ring of 5 or 6 members which can be joined to the rest of the molecule by any available C or N atom claim 1 , where Cycontains 1 or 2 heteroatoms selected from N claim 1 , O and S claim 1 , where one or more atoms of C or S of the ring may be oxidized to form CO claim 1 , SO or SOgroups claim 1 , and where Cyis optionally replaced by one or more R.10. The A compound according to any one of where each Rindependently represents Calkyl claim 1 , hydroxyl claim 1 , Calkoxyl claim 1 , haloCalkyl claim 1 , hydroxyCalkyl or halogen.11. The compound according to where n represents 0 or 1.12. The compound according to where m represents 1.16. A pharmaceutical composition comprising a compound of formula I according to or a pharmaceutically acceptable salt thereof and one or more ...

USE OF ARYLALKANOLAMINES AS SIGMA-1 RECEPTOR ANTAGONISTS

The present invention relates to the use of arylalkanolamine compounds with sigma-1 receptor antagonist activity. In particular, the said arylalkanolamine compounds are useful in the treatment of conditions selected from the abuse of psychotropic substances such as cocaine or amphetamines, pain and cancer. 2. The aryl alkanolamine compounds according to claim 1 , wherein R1 and R2 claim 1 , equal to or different from each other claim 1 , are a linear or branched (C-C)alkyl group claim 1 , a benzyl group claim 1 , or R1 and R2 form claim 1 , together with the nitrogen atom to which they are bonded claim 1 , a 6-membered heterocyclic ring claim 1 , optionally comprising another heteroatom selected from N claim 1 , O and S.3. The aryl alkanolamine compounds according to claim 2 , wherein R1 and R2 claim 2 , equal to or different from each other claim 2 , are a methyl group claim 2 , an ethyl group claim 2 , a benzyl group claim 2 , or R1 and R2 form claim 2 , together with the nitrogen atom to which they are bonded claim 2 , a piperidine or morpholine ring.4. The aryl alkanolamine compounds according to claim 3 , wherein R1 and R2 form claim 3 , together with the nitrogen atom to which they are bonded claim 3 , a piperidine ring.5. The aryl alkanolamine compounds according to claim 1 , wherein R3 and R4 claim 1 , equal to or different from each other claim 1 , are hydrogen atom claim 1 , a phenyl group claim 1 , or R3 and R4 form claim 1 , together with the ring to which they are bonded claim 1 , an optionally substituted naphthalene ring.627.-. (canceled)28. The aryl alkanolamine compounds according to claim 5 , wherein said naphthalene ring formed by R3 and R4 is substituted with a hydroxy) group claim 5 , an alkoxy group having from 1 to 3 carbon atoms claim 5 , or a halogen atom.29. The aryl alkanolamine compounds according to claim 5 , wherein R3 is a hydrogen atom and R4 is a phenyl group.30. The aryl alkanolamine compounds according to claim 1 , wherein n is an ...

SPHINGOSINE KINASE TYPE 1 INHIBITORS AND USES THEREOF

Provided are inhibitors of sphingosine kinase Type I that are useful in a number of applications, indications and diseases, as well as for monitoring pharmacokinetics and patient management. These compounds are applicable to treating tumors of the central nervous system, such as glioblastoma multiforme (GBM). 5. The method of claim 4 , wherein R is a straight carbon chain claim 4 , a branched carbon chain claim 4 , a straight carbon chain comprising one or more heteroatoms claim 4 , a branched carbon chain comprising one or more heteroatoms claim 4 , a cyclic ring claim 4 , a heterocyclic ring claim 4 , an aromatic ring claim 4 , a hetero-aromatic ring claim 4 , or any combination of the foregoing.6. The method of claim 5 , wherein R is a straight carbon chain claim 5 , a branched carbon chain claim 5 , a straight carbon chain comprising one or more heteroatoms claim 5 , a branched carbon chain comprising one or more heteroatoms claim 5 , a cyclic ring claim 5 , a heterocyclic ring claim 5 , an aromatic ring claim 5 , or a hetero-aromatic ring.7. The method of claim 6 , wherein R is a straight carbon chain claim 6 , a branched carbon chain claim 6 , a straight carbon chain comprising one or more heteroatoms claim 6 , or a branched carbon chain comprising one or more heteroatoms.8. The method of claim 7 , wherein R is a straight carbon chain or a branched carbon chain.9. The method of claim 8 , wherein R is a straight carbon chain. This application is a continuation of U.S. application Ser. No. 16/199,337 filed Nov. 26, 2018, which is a continuation of U.S. application Ser. No. 15/954,131 filed Apr. 16, 2018, (now U.S. Pat. No. 10,166,204), which is a continuation of U.S. application Ser. No. 15/181,826 filed Jun. 14, 2016 (now U.S. Pat. No. 9,974,758), which is a continuation of U.S. application Ser. No. 13/649,221 filed Oct. 11, 2012 (now U.S. Pat. No. 9,388,121), which is a divisional of U.S. application Ser. No. 12/584,131 filed Aug. 31, 2009 (now U.S. Pat. No. 8 ...

PROCESSES FOR THE PREPARATION OF ENAMINES

The invention disclosed in this document is related to the field of processes for the preparation of enamines 1 (1) wherein said first mixture comprises pyrrolidine, and', '(2) wherein said second mixture comprises 3-methylsulfanyl-butyraldehyde and toluene, and', '(3) wherein said first mixture is contacted with said second mixture below the surface of said second mixture;', {'sub': '2', '(B) reacting in said reaction zone said pyrrolidine and said 3-methylsulfanyl-butyraldehyde to produce 1-(3-methylsulfanyl-but-1-enyl)-pyrrolidine and HO, wherein said reacting is conducted under azeotropic distillation conditions comprising'}, '(1) a pressure from about 5000 Pa to about 15000 Pa, and', '(2) a temperature from about 25° C. to about 65° C.; and, '(A) contacting a first mixture with a second mixture in a reaction zone'}{'sub': '2', 'claim-text': wherein the ratio of', '(the amount of first mixture added): (the vapor phase removed) is from about', '(1 part first mixture added): (3 parts vapor phase removed) to about', '(1 part first mixture added): (10 parts vapor phase removed);, '(C) removing a vapor phase comprising toluene and HO and essentially no 3-methylsulfanyl-butyraldehyde,'}{'sub': '2', 'wherein said process no desiccants are used to remove HO in said process; and'}wherein said process the molar ratio of amine to carbonyl is greater than 1 but less than about 1.1.. A process comprising: This Application is a continuation of U.S. non-provisional application Ser. No. 13/303,206, filed 23 Nov. 2011, which claims priority from and benefit of U.S. provisional application 61/419,277, filed on Dec. 3, 2010. The entire contents of these applications are hereby incorporated by reference into this Application.The invention disclosed in this document is related to the field of processes for the preparation of enamines.Enamines are very useful molecules. They have been used in a wide variety of reactions such as, for example, electrophilic substitution and addition, ...

PROCESSES FOR THE PREPARATION OF ENAMINES

The invention disclosed in this document is related to the field of processes for the preparation of enamines 1{'sub': '2', 'claim-text': (1) a pressure from about 5000 Pascals (Pa) to about 15,000 Pa, and', '(2) a temperature from about 25° C. to about 65° C.; and, '(A) reacting, in a reaction zone that comprises solvents, pyrrolidine and 3-methylsulfanyl-butyraldehyde to produce 1-(3-methylsulfanyl-but-1-enyl)-pyrrolidine and HO, wherein said reacting, in said reaction zone, is conducted under azeotropic distillation conditions comprising'}{'sub': 2', '2', '2, 'wherein said solvents are initially toluene and acetonitrile, and then HO, where said HO is produced from the condensation of said pyrrolidine and said 3-methylsulfanyl-butyraldehyde to produce said 1-(3-methylsulfanyl-but-1-enyl)-pyrrolidine, thereby forming a ternary azeotrope of toluene, acetonitrile, and HO; and'}{'sub': '2', '(B) removing a vapor phase from said reaction zone wherein said vapor phase comprises HO;'}{'sub': '2', 'wherein said process no desiccants are used to remove HO;'}wherein said process said molar ratio of pyrrolidine to 3-methylsulfanyl-butyraldehyde is greater than 1 but less than about 1.1.. A process to produce 1-(3-methylsulfanyl-but-1-enyl)-pyrrolidine said process comprising: This Application is a continuation of U.S. non-provisional application Ser. No. 13/303,195, filed on 23 Nov. 2011, which claims priority from, and benefit of U.S. provisional application 61/419,300, filed on Dec. 3, 2010. The entire content of these applications are hereby incorporated by reference into this Application.The invention disclosed in this document is related to the field of processes for the preparation of enamines.Enamines are very useful molecules. They have been used in a wide variety of reactions such as, for example, electrophilic substitution and addition, oxidation and reduction, and cycloaddition (J. Kang, Y. R. Cho, and J. H. Lee, 13, No. 2 , 1992).An early method for preparing ...

Processes for the Preparation of Enamines

The invention disclosed in this document is related to the field of processes for the preparation of enamines 1 (1) wherein said first mixture comprises a carbonyl wherein said carbonyl is 3-methylsulfanyl-butyraldehyde, and', '(2) wherein said second mixture comprises toluene and an amine wherein said amine is pyrrolidine;, '(A) contacting, in a reaction zone, a first mixture with a second mixture'}{'sub': '2', 'claim-text': (1) a pressure from about 100 Pascals (Pa) to about 120,000 Pa, and', '(2) a temperature below about the thermal decomposition temperature of said enamine during said reacting; and, '(B) reacting in said reaction zone said amine and said carbonyl to produce an enamine and HO, wherein said enamine is 1-(3-methylsulfanyl-but-1-enyl)-pyrrolidine, and wherein reacting is conducted under azeotropic distillation conditions comprising'}{'sub': '2', '(C) removing a vapor phase comprising said toluene, amine, and HO; and'}(D) condensing said vapor phase from step (C) to produce a condensate; and{'sub': '2', '(E) contacting said condensate from step (D) with a recovery mixture comprising HO, toluene, amine, and sodium hydroxide to produce a separate mixture comprising said amine and said toluene, and another mixture comprising H2O and sodium hydroxide; and'}(F) optionally, returning said mixture comprising amine and toluene from step (E) back to said reaction zone;wherein said process no desiccants are used to remove water andwherein said process the molar ratio of amine to carbonyl is greater than 1 but less than about 1.1.. A process to produce 1-(3-methylsulfanyl-but-1-enyl)-pyrrolidine said process comprising: This Application is a continuation of U.S. non-provisional application Ser. No. 13/303,187, which was filed on 23 Nov. 2011, and claims priority from, and benefit of U.S. provisional application 61/419,296, filed on Dec. 3, 2010. The entire contents of these application are hereby incorporated by reference into this Application.The invention ...

SPHINGOSINE KINASE TYPE 1 INHIBITORS AND USES THEREOF

Provided are inhibitors of sphingosine kinase Type I and their use in the treatment of asthma, among other indications and diseases. 5. The method of claim 4 , wherein R is a straight carbon chain claim 4 , a branched carbon chain claim 4 , a straight carbon chain comprising one or more heteroatoms claim 4 , a branched carbon chain comprising one or more heteroatoms claim 4 , a cyclic ring claim 4 , a heterocyclic ring claim 4 , an aromatic ring claim 4 , a hetero-aromatic ring claim 4 , or any combination of the foregoing.6. The method of claim 5 , wherein R is a straight carbon chain claim 5 , a branched carbon chain claim 5 , a straight carbon chain comprising one or more heteroatoms claim 5 , a branched carbon chain comprising one or more heteroatoms claim 5 , a cyclic ring claim 5 , a heterocyclic ring claim 5 , an aromatic ring claim 5 , or a hetero-aromatic ring.7. The method of claim 6 , wherein R is a straight carbon chain claim 6 , a branched carbon chain claim 6 , a straight carbon chain comprising one or more heteroatoms claim 6 , or a branched carbon chain comprising one or more heteroatoms.8. The method of claim 7 , wherein R is a straight carbon chain or a branched carbon chain.9. The method of claim 8 , wherein R is a straight carbon chain. This application is a continuation of U.S. application Ser. No. 15/954,131 filed Apr. 16, 2018, which is a continuation of U.S. application Ser. No. 15/181,826 filed Jun. 14, 2016 (now U.S. Pat. No. 9,974,758), which is a continuation of U.S. application Ser. No. 13/649,221 filed Oct. 11, 2012 (now U.S. Pat. No. 9,388,121), which is a divisional of U.S. application Ser. No. 12/584,131 filed Aug. 31, 2009 (now U.S. Pat. No. 8,314,151), which is a continuation-in-part of U.S. application Ser. No. 12/387,228 filed Apr. 29, 2009 (now U.S. Pat. No. 8,372,888), which claims the benefit of U.S. Provisional Application No. 61/048,638 filed Apr. 29, 2008, the contents of all of which are hereby incorporated by reference in ...

SPHINGOSINE KINASE TYPE 1 INHIBITORS AND USES THEREOF

Provided are inhibitors of sphingosine kinase Type I that are useful in the treatment of neuropathic pain. 5. The method of claim 4 , wherein R is a straight carbon chain claim 4 , a branched carbon chain claim 4 , a straight carbon chain comprising one or more heteroatoms claim 4 , a branched carbon chain comprising one or more heteroatoms claim 4 , a cyclic ring claim 4 , a heterocyclic ring claim 4 , an aromatic ring claim 4 , a hetero-aromatic ring claim 4 , or any combination of the foregoing.6. The method of claim 5 , wherein R is a straight carbon chain claim 5 , a branched carbon chain claim 5 , a straight carbon chain comprising one or more heteroatoms claim 5 , a branched carbon chain comprising one or more heteroatoms claim 5 , a cyclic ring claim 5 , a heterocyclic ring claim 5 , an aromatic ring claim 5 , or a hetero-aromatic ring.7. The method of claim 6 , wherein R is a straight carbon chain claim 6 , a branched carbon chain claim 6 , a straight carbon chain comprising one or more heteroatoms claim 6 , or a branched carbon chain comprising one or more heteroatoms.8. The method of claim 7 , wherein R is a straight carbon chain or a branched carbon chain.9. The method of claim 8 , wherein R is a straight carbon chain. This application is a continuation of U.S. application Ser. No. 16/813,961 filed Mar. 10, 2020, which is a continuation of U.S. application Ser. No. 16/572,699 filed Sep. 17, 2019, which is a continuation of U.S. application Ser. No. 16/199,337 filed Nov. 26, 2018 (now U.S. patent Ser. No. 10/456,370), which is a continuation of U.S. application Ser. No. 15/954,131 filed Apr. 16, 2018, (now U.S. Pat. No. 10,166,204), which is a continuation of U.S. application Ser. No. 15/181,826 filed Jun. 14, 2016 (now U.S. Pat. No. 9,974,758), which is a continuation of U.S. application Ser. No. 13/649,221 filed Oct. 11, 2012 (now U.S. Pat. No. 9,388,121), which is a divisional of U.S. application Ser. No. 12/584,131 filed Aug. 31, 2009 (now U.S. Pat. ...

AMINO ALCOHOL-BORON-BINOL COMPLEX AND METHOD FOR PREPARING OPTICALLY ACTIVE AMINO ALCOHOL DERIVATIVE BY USING SAME

Disclosed are an amino alcohol-boron-binol complex as an intermediate, including Complex 3-1-1 shown below, and a method for preparing an optically active amino alcohol by using the same, wherein a racemic amino alcohol is resolved in an enation selective manner using a boron compound and a (R)- or (S)-binol, whereby an amino alcohol derivative with high optical purity can be prepared at high yield. 2. The method of claim 1 , wherein the boron compound of the first step is selected from the group consisting of boric acid claim 1 , trimethyl borate claim 1 , triethyl borate claim 1 , triisopropyl borate claim 1 , tributyl borate claim 1 , and triphenyl borate.4. The method of claim 1 , wherein the solvent in the first step is selected from the group consisting of acetonitrile claim 1 , dichloromethane claim 1 , toluene claim 1 , and isopropanol.5. The method of claim 1 , wherein the boron compound and the (R)- or (S)-binol are added in an amount of 1 mole equivalent and 0.45-0.6 mole equivalents claim 1 , respectively claim 1 , based on 1 mole equivalent of the racemic compound represented by Chemical Formula 1 in the first step. This application claims priority to Korean Application No. 10-2020-0001522, filed on Jan. 6, 2020, the entire disclosure of which is incorporated herein by reference.The present disclosure relates to an amino alcohol-boron-binol complex as an intermediate and a method for preparing an optically active amino alcohol derivative by using the same.Typical among chemically synthesized medication materials are racemates in which enantiomers are mixed. However, only one of the enantiomers in many racemic medications may be pharmacologically active whereas the other may be inactive or may even cause a side effect. For example, thalidomide exists in two mirror-image forms. Of the racemic mixture, one enantiomer has sedative effects whereas the other isomer is teratogenic. For ethambutol, one enantiomer is used to treat tuberculosis whereas another ...

SPHINGOSINE KINASE TYPE 1 INHIBITORS AND USES THEREOF

Provided are inhibitors of sphingosine kinase Type I that are useful in a number of applications, indications and diseases, as well as for monitoring pharmacokinetics and patient management. These compounds are applicable to treating ischemic diseases such as myocardial infarction and stroke. 5. The method of claim 4 , wherein R is a straight carbon chain claim 4 , a branched carbon chain claim 4 , a straight carbon chain comprising one or more heteroatoms claim 4 , a branched carbon chain comprising one or more heteroatoms claim 4 , a cyclic ring claim 4 , a heterocyclic ring claim 4 , an aromatic ring claim 4 , a hetero-aromatic ring claim 4 , or any combination of the foregoing.6. The method of claim 5 , wherein R is a straight carbon chain claim 5 , a branched carbon chain claim 5 , a straight carbon chain comprising one or more heteroatoms claim 5 , a branched carbon chain comprising one or more heteroatoms claim 5 , a cyclic ring claim 5 , a heterocyclic ring claim 5 , an aromatic ring claim 5 , or a hetero-aromatic ring.7. The method of claim 6 , wherein R is a straight carbon chain claim 6 , a branched carbon chain claim 6 , a straight carbon chain comprising one or more heteroatoms claim 6 , or a branched carbon chain comprising one or more heteroatoms.8. The method of claim 7 , wherein R is a straight carbon chain or a branched carbon chain.9. The method of claim 8 , wherein R is a straight carbon chain.15. The method of claim 14 , wherein R is a straight carbon chain claim 14 , a branched carbon chain claim 14 , a straight carbon chain comprising one or more heteroatoms claim 14 , a branched carbon chain comprising one or more heteroatoms claim 14 , a cyclic ring claim 14 , a heterocyclic ring claim 14 , an aromatic ring claim 14 , a hetero-aromatic ring claim 14 , or any combination of the foregoing.16. The method of claim 15 , wherein R is a straight carbon chain claim 15 , a branched carbon chain claim 15 , a straight carbon chain comprising one or ...

SPHINGOSINE KINASE TYPE 1 INHIBITORS AND USES THEREOF

Provided are inhibitors of sphingosine kinase Type I that are useful in a number of applications, indications and diseases, as well as for monitoring pharmacokinetics and patient management. These compounds are applicable to treating tumors of the central nervous system, such as glioblastoma multiforme (GBM). 5. The method of claim 4 , wherein R is a straight carbon chain claim 4 , a branched carbon chain claim 4 , a straight carbon chain comprising one or more heteroatoms claim 4 , a branched carbon chain comprising one or more heteroatoms claim 4 , a cyclic ring claim 4 , a heterocyclic ring claim 4 , an aromatic ring claim 4 , a hetero-aromatic ring claim 4 , or any combination of the foregoing.6. The method of claim 5 , wherein R is a straight carbon chain claim 5 , a branched carbon chain claim 5 , a straight carbon chain comprising one or more heteroatoms claim 5 , a branched carbon chain comprising one or more heteroatoms claim 5 , a cyclic ring claim 5 , a heterocyclic ring claim 5 , an aromatic ring claim 5 , or a hetero-aromatic ring.7. The method of claim 6 , wherein R is a straight carbon chain claim 6 , a branched carbon chain claim 6 , a straight carbon chain comprising one or more heteroatoms claim 6 , or a branched carbon chain comprising one or more heteroatoms.8. The method of claim 7 , wherein R is a straight carbon chain or a branched carbon chain.9. The method of claim 8 , wherein R is a straight carbon chain.14. The method of claim 13 , wherein R is a straight carbon chain claim 13 , a branched carbon chain claim 13 , a straight carbon chain comprising one or more heteroatoms claim 13 , a branched carbon chain comprising one or more heteroatoms claim 13 , a cyclic ring claim 13 , a heterocyclic ring claim 13 , an aromatic ring claim 13 , a hetero-aromatic ring claim 13 , or any combination of the foregoing.15. The method of claim 14 , wherein R is a straight carbon chain claim 14 , a branched carbon chain claim 14 , a straight carbon chain ...

Processes for the Preparation of Enamines

The invention disclosed in this document is related to the field of processes for the preparation of enamines

PROCESSES FOR THE PREPARATION OF ENAMINES

The invention disclosed in this document is related to the field of processes for the preparation of enamines

Sphingosine kinase type 1 inhibitors, and processes for using same

Provided are novel compositions and analogs which are useful in a number of applications, indications and diseases, as well as for monitoring pharmakinetics and patient management. These compounds and analogs are applicable to treating tumors of the central nervous system, e.g., glioblastoma (GBM).

NAPHTHALENE DERIVATIVES SUBSTITUTED BY AN ALCANOL (OMEGA-AMINO) GROUP WITH ANTIMICROBIAL ACTIVITY, THEIR PREPARATION AND THE COMPOSITIONS CONTAINING THEM

The 1-butyl-2-hydroxyaralkyl piperazine derivatives and the uses as anti-depression medicine thereof

Antimicrobial aromatic derivatives substituted by an (omega amino)alkanol group and compositions containing them

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一类化合物及其制备方法与应用

本发明公开一类化合物及其制备方法与应用，属于医药领域。该化合物为含有苯乙醇胺结构的氨基甲酰酯类衍生物，其化学结构通式如式(I)所示。该化合物具有显著的抑制乙酰胆碱酯酶和丁酰胆碱酯酶的作用，可用于作为双靶点胆碱酯酶抑制剂的用途。也可在制备治疗与胆碱酯酶相关的疾病的药物上进行应用。

Method of producing derivatives of 1,1-diphenyl-2-ylkylamine or their salts

1,1 min -biphenyl-2-yl alkylamine derivatives of formula (I): <CHEM> wherein: X is hydrogen or a halo substituent at any position in the phenyl ring; R<1> is hydrogen, hydroxy, C IDENTICAL N, CONR<5>R<6>, or CO2R<8> where R<5>, R<6>, R<8> independently represent hydrogen or alkyl; R<2> is hydrogen or alkyl; Z is -(CH2)n- or -CH2@@CH2-; where n is an integer of from 2 to 4; R<3> and R<4> independently are hydrogen, C1-6 alkyl, CH2C2-5 alkenyl, phenyl C1-3 alkyl, or taken together with the adjacent nitrogen atom form a heterocyclic group or a pharmaceutically-acceptable salt thereof. The compounds are prepared by the usual methods for analogous compounds. They have been found to be effective in the treatment of cardiac arrhythmias. Pharmaceutical formulations have been prepared.

Patent SU433680A3

1*1**biphenyll22yllalkylamine derivative

N-phenyl-N'-phenylpropylpiperazine derivatives and process for the preparation thereof

本发明涉及由式(1)表示的N－苯基－N’－苯丙基哌嗪衍生物,其中R 1 代表低级烷基;R 2 代表低级烷氧基;R 3 代表氰基、羧基或吲哚羰基;药物;和制备该衍生物的方法。本发明化合物具有有效的α 1 －肾上腺素受体阻滞活性,因此可用于高血压、充血性心脏衰竭、心肌缺血、心律不齐、心绞痛和由良性前列腺增生引起的尿路梗阻和尿频的预防或治疗。

Stereoselective alkylation of chiral 2-methyl-4-protected piperazines

在一个示例性的实施方案中，本发明描述了一种通过新型选择性烷基化方法以高立体化学纯度合成下面的化合物(I)和类似的化合物的方法。

N-phenyl-n'-phenylpropylpiperazine derivatives and process for the preparation thereof

본 발명은 일반식(1) (식중, R 1 은 저급알킬기를 나타내며, R 2 는 저급알콕시기를 나타내며, R 3 는 시아노기, 카르복실기 또는 인돌카르보닐기를 나타낸다.)로 표시되는 N-페닐-N'-페닐프로필피페라진 유도체 및 이를 함유하는 의약 및 그의 제조방법에 관한 것이다. 이 화합물은 강한 α 1 -아드레날린 작동성 수용체 차단작용을 가지며, 고혈압, 울혈성심부전, 심근허헐, 부정맥, 협심증, 전립선비대증에 동반하는 배뇨장애, 빈뇨증 등의 예방·치료에 유용하다.

Biperiden hydrochloride preparation method

本发明提供了一种盐酸比哌立登的新制备方法，属于药物与化学合成技术领域，它解决了大规模制备外向型盐酸比哌立登，制得的产品符合最新欧洲药典标准。该方法以5‑乙烯‑2‑降冰片烯为起始原料经选择性氧化制得关键外型5‑乙酰基降冰片烯，再经曼尼希反应、外向异构化成盐反应、格氏反应及成盐反应制得本品。本发明原料易得、价格低廉、操作简单，反应条件温和，具有良好的工业化应用价值。

Propylamine derivatives

Disclosed are e.g. certain novel 2-benzyl-3-(substituted)-phenoxypropylamines, their methods of synthesis and pharmaceutical compositions. Said compounds are useful as potent and centrally active serotonin uptake inhibitors for the treatment of psychotropic disorders, particularly depression.

METHODS FOR PRODUCING ENAMINS

1. Способ, включающий:(A) контактирование первой смеси со второй смесью в реакционной зоне(1) где указанная первая смесь содержит карбонил (т.е. альдегид или кетон), имеющий следующую формулу,(a) где R1 и R2 каждый независимо выбраны из C-Cалкила, C-Cциклоалкила, C-Cалкоксиалкила, C-Cарилалкила, C-Cалкиламиноалкила, арила и гетероарила, каждый из которых независимо замещен одним или несколькими S-R6, где каждый R6 независимо выбран из C-Cалкила, C-Cциклоалкила, C-Cалкоксиалкила, C-Cарилалкила, C-Cалкиламиноалкила, арила и гетероарила, и(b) где R3 выбран из H, C-Cалкила, C-Cциклоалкила, C-Cалкоксиалкила, C-Cарилалкила, C-Cалкиламиноалкила, арила и гетероарила, и(2) где указанная вторая смесь содержит неполярный растворитель с высокой точкой кипения и амин, имеющий следующую формулу,где R4 и R5 каждый независимо выбраны из C-Cалкила, C-Cциклоалкила, C-Cалкоксиалкила, C-Cарилалкила, C-Cалкиламиноалкила, арила и гетероарила, или R4 и R5, взятые всовокупности с N, представляют 5- или 6-членное насыщенное или ненасыщенное кольцо;(B) реакция в указанной реакционной зоне указанного амина и указанного карбонила с образованием енамина и HO, где реакцию проводят при дистилляционных условиях, включающих:(1) давление от приблизительно 100 Паскалей (Па) до приблизительно 120000 Па, и(2) температуру приблизительно ниже, но предпочтительно ниже, температуры термического разложения указанного енамина в процессе указанной реакции; и(C) удаление газовой фазы, включая указанный неполярный растворитель с высокой точкой кипения, амин, и HO; и(D) конденсацию указанной газовой фазы со стадии (C) с образованием конденсата; и(E) контактирование указанного конденсата со стадии (D) с восстанавливающ� РОССИЙСКАЯ ФЕДЕРАЦИЯ (19) RU (11) (51) МПК C07D 295/084 (13) 2013 130 236 A (2006.01) ФЕДЕРАЛЬНАЯ СЛУЖБА ПО ИНТЕЛЛЕКТУАЛЬНОЙ СОБСТВЕННОСТИ (12) ЗАЯВКА НА ИЗОБРЕТЕНИЕ (21)(22) Заявка: 2013130236/04, 23.11.2011 (71) Заявитель(и): ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи (US) Приоритет(ы): (30) Конвенционный ...

Process for producing derivatives of 1,1'-biphenyl-2-ylalkylamine

1,1 min -biphenyl-2-yl alkylamine derivatives of formula (I): <CHEM> wherein: X is hydrogen or a halo substituent at any position in the phenyl ring; R<1> is hydrogen, hydroxy, C IDENTICAL N, CONR<5>R<6>, or CO2R<8> where R<5>, R<6>, R<8> independently represent hydrogen or alkyl; R<2> is hydrogen or alkyl; Z is -(CH2)n- or -CH2@@CH2-; where n is an integer of from 2 to 4; R<3> and R<4> independently are hydrogen, C1-6 alkyl, CH2C2-5 alkenyl, phenyl C1-3 alkyl, or taken together with the adjacent nitrogen atom form a heterocyclic group or a pharmaceutically-acceptable salt thereof. The compounds are prepared by the usual methods for analogous compounds. They have been found to be effective in the treatment of cardiac arrhythmias. Pharmaceutical formulations have been prepared.

Patent FR2148001A1

Esters of 3-(1-piperidyl)-1-cyclohexyl-1-phenyl-1-propanol - - as anti parkinsonism agents of long and short duration

Cpds. (I) where n = 0, 11,13 or 15) are prepd. by esterification of the free alcohol with an acid halide. Cpds. where n =0 are rapid acting of short duration and those where n = 11,13 or 15 act over 14-21 days.

Amino gp contg cyclopropane derivs - with pharmacological props

Title cpds. are of formula:- (where R1 and R2 are alkyl or aralkyl, or form, together with the N atom to which they are linked, a morpholino, piperidino or substd. piperidine radical of formula: (where Z1 is OH, (mono or di-alkyl substd.) carbamyl, acyl or cyano gp.; Z2 is a piperidine or phenyl gp. opt. substd. by halogen, trifluoromethyl, or (where Y1 = phenyl and Y2 = acyl, or together with the linking N form an oxo-2-benzimidazoline gp.); R3 is H, alkyl, or aryl, opt. substd. by >=1 alkyl; R4 is H or acyl; R5 is alkyl or aryl, or their acid addition salts. The derivs. are formed by the reaction of a ketone with a metal deriv. of R3 and then esterifying the alcohol formed.

NOVEL DERIVATIVES OF PIPERAZINE AND THEIR SALTS, PROCESS FOR PREPARING THEM AND THEIR THERAPEUTIC APPLICATION

L'INVENTION A POUR OBJET UN DERIVE DE PIPERAZINE OU UN SEL PHARMACEUTIQUEMENT ACCEPTABLE DE CELUI-CI. CE DERIVE REPOND A LA FORMULE: (CF DESSIN DANS BOPI) DANS LAQUELLE R REPRESENTE UN ATOME D'HYDROGENE OU UN RADICAL ALKYLE INFERIEUR, R EST UN RADICAL HYDROXYLE, ARALKYLOXY, ALCOXY INFERIEUR DE 1 A 5 ATOMES DE CARBONE OU ALCENYLOXY INFERIEUR DE 3 A 5 ATOMES DE CARBONE, R EST UN ATOME D'HYDROGENE OU UN RADICAL ARALKYLOXY, ALCOXY INFERIEUR DE 1 A 5 ATOMES DE CARBONE OU ALCENYLOXY INFERIEUR DE 3 A 5 ATOMES DE CARBONE, ET REST UN ATOME D'HYDROGENE OU UN RADICAL ALCOXY INFERIEUR DE 1 A 5 ATOMES DE CARBONE, A LA CONDITION QUE R SOIT AUTRE QU'UN RADICAL ALCOXY INFERIEUR DE 1 A 5 ATOMES DE CARBONE QUAND R ET R SONT TOUS DEUX DES ATOMES D'HYDROGENE. PREPARATION D'UN MEDICAMENT QUI AMELIORE LA CIRCULATION CEREBRALE. THE SUBJECT OF THE INVENTION IS A PIPERAZINE DERIVATIVE OR A PHARMACEUTICALLY ACCEPTABLE SALT OF THE SAME. THIS DERIVATIVE MEETS THE FORMULA: (CF DRAWING IN BOPI) IN WHICH R REPRESENTS A HYDROGEN ATOM OR A LOWER RADICAL ALKYL, R IS A HYDROXYL RADICAL, ARALKYLOXY, ALCOXY LESS THAN 1 TO 5 ATOMS OF CARBONYURON 3 OR ALCENYLO AT 5 CARBON ATOMS, R IS A HYDROGEN ATOM OR A RADICAL ARALKYLOXY, ALCOXY LESS THAN 1 TO 5 CARBON ATOMS OR ALCENYLOXY LESS THAN 3 TO 5 CARBON ATOMS, AND REMAINS A HYDROGEN ATOM OR A RADICAL ALCOXY FROM 1 TO 5 CARBON ATOMS, PROVIDED THAT R IS OTHER THAN A RADICAL ALCOXY LESS THAN 1 TO 5 CARBON ATOMS WHEN R AND R ARE BOTH HYDROGEN ATOMS. PREPARATION OF A MEDICINE THAT IMPROVES CEREBRAL CIRCULATION.

1 - ((1,1-DIPHENYL) -1-ALCENYL) -PIPERAZINE DERIVATIVES, PROCESS FOR OBTAINING AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

New piperazines which can be used in therapy, in particular as anti-inflammatory agents.

3-(Alkyn-3-yloxy)-1-piperazinopropan-2-ols - with neuroleptic, antihypertensive, antiemetic and antitussive activity

The cpds. of formula (where R', R2 singly are alkyl or together are the group -(CH2)n - forming 5-8C cycloalkyl; A is a group where X is H, halogen CF3, alkyl, alkoxy, or a group where R is alkyl) are neuroleptic, hypotensive, antemetic and antitussive agents. All are prepd. as hydrochlorides.

Process for the preparation of piperazine compounds, inter alia 1- (2-ethoxy-2-phenylethyl) -4- (2-methoxy-phenyl) -piperazine

Patent FR2347359B1

3-phenyl-3-(substd-amino)-3,4-dihydro-isocoumarins - and isochromans - as anti hypertensive agents and diuretics

Process for the preparation of pyrrolidines

Process for the preparation of new piperazino-phenylethanol derivatives

Patent FR2138488B1

Patent FR2148001B1

Hypotensive and antiarrhythmic piperazines - 1-(3-phenoxy-2-hydroxy propyl)-4-substd. piperazines

Piperazine cpds. of formula (I) and their salts (where R1 is H, 1-6C alkyl or acyl nitro, or carbamoyl, R1 is -(CH2)nR7, -COR12 or benzimidazoyl, R2-6 are each H, halogen, 1-6C alk(en)yl NO2, phenyl or acylamino, or two adjacent gps. may with the phenyl ring form alpha or beta-naphtayl, R7 is OH, alkoxy, (substd.)alkoxy, nitro-oxy, amino, mono- or di-alkylamino, CN, carboxy, alkoxycarbonyl, aryloxy(opt. substd. esp. by 1 or more alkox, carbazoyl, or methylene-3,4-dioxy phenyl gps). -CONR8R9, -CONHN=CH-R10, 2,5-dimethyl-1-pyrrolyl carbamoyl, or -CHOHR11 (when n = 1), R8 and R9 are each H, alk(en)yl or (substd)phenyl, or together with the N atom form a heterocycle which may contain other hetero atoms, R10 is alk(en)yl, or phenyl (opt. substd. by halogen or 1-6C alkoxy), R11 = CH2OH, alkoxymethyl, phenyl, benzyl or -CH2-NRaRb, Ra and Rb are each H, alkyl or together with the N atom form pyrrolidino or morpholino, R12 is (ar)alkyl or (ar)alkenyl, opt. substd. by halogen, hydroxy or 1-6C alkoxy, and n = 1,2 or 3) are adrenolytics, hypotensives, anti-hypertensives and anti-arrhythmics.

Substituted diphenylalkylamines.

Patent FR148F

Medicinal product based on butynic derivatives of piperazine, having in particular analgesic and myro-relaxing activity.

New piperazine derivatives and their preparation

Aryl-1- (o-alkoxy-phenyl-4-piperazinyl-1) -2,3-or 4-alkanols, process for their preparation and their use in the preparation of medicaments.

La présente invention concerne l'utilisation des composés de formule générale (I): (CF DESSIN DANS BOPI) dans laquelle - R1 , R2 identiques, ou différents, sont choisis parmi un atome d'hydrogène, un groupe hydroxy, un groupe méthoxy; - R3 est choisi parmi un atome d'hydrogène et un groupe alkyle ayant de 1 à 5 atomes de carbone; et - n est un nombre entier variant de 1 à 3; pour la préparation d'un médicament utile pour le traitement des dysuries en particulier liées à une hypertonie urétrale ou à une hypertrophie bégnine de la prostate.

New hydroxy-diamines and their preparation process

New tertiary amines and process for their preparation

(1,1-BIPHENYL-2-YL) -PROPYL- AND BUTYLAMINES, THEIR PREPARATION AND THEIR THERAPEUTIC USE

L'INVENTION CONCERNE DES COMPOSES DE FORMULE: (CF DESSIN DANS BOPI) OU X EST UN ATOME D'HYDROGENE OU UN SUBSTITUANT HALO; R EST H, OH, CN OU UN GROUPEMENT AMIDE OU ACIDE OU EVENTUELLEMENT CERTAINS DE LEURS DERIVES; R EST UN ATOME D'HYDROGENE OU UN GROUPEMENT ALKYLE EN C-C; Z EST UN GROUPEMENT ALKYLENE OU ALKYLENE HYDROXYLE; R ET R SONT INDEPENDAMMENT DES ATOMES D'HYDROGENE OU DES GROUPEMENTS ALKYLE EN C-C, ALCENYLE, PHENYLALKYLE OU PEUVENT FORMER AVEC L'ATOME D'AZOTE UN NOYAU HETEROCYCLIQUE, ET LEURS SELS PHARMACEUTIQUEMENT ACCEPTABLES. CES COMPOSES SONT UTILES COMME AGENTS PHARMACOLOGIQUES, EN PARTICULIER DANS LE TRAITEMENT DES TROUBLES CARDIOVASCULAIRES. THE INVENTION RELATES TO COMPOUNDS OF FORMULA: (CF DRAWING IN BOPI) OR X IS A HYDROGEN ATOM OR A HALO SUBSTITUTE; R IS H, OH, CN OR AN AMID OR ACID GROUP OR SOME OF THEIR DERIVATIVES; R IS A HYDROGEN ATOM OR A C-C ALKYL GROUP; Z IS AN ALKYLENE OR ALKYLENE HYDROXYL GROUP; R AND R ARE INDEPENDENT OF HYDROGEN ATOMS OR ALKYL GROUPS IN C-C, ALCENYL, PHENYLALKYL OR MAY FORM WITH THE NITROGEN ATOM A HETEROCYCLIC CORE, AND THEIR PHARMACEUTICALLY ACCEPTABLE SALTS. THESE COMPOUNDS ARE USEFUL AS PHARMACOLOGICAL AGENTS, IN PARTICULAR IN THE TREATMENT OF CARDIOVASCULAR DISORDERS.

Patent FR4290M

Process for protecting plants against fungi and compositions intended for this purpose

Process for preparing piperazine derivatives, inter alia 1- (3-ethoxy-3-phenyl-propyl) -4- (3-methyl-phenyl) -piperazine

Patent FR2081579A1

Process for the preparation of 1,1'-biphenyl-2-yl alkylamines

Biphenylylalkylamines I [X=H, halo; R1=H, OH, cyano, coNH2, CO2R8; R8=H, C1˜C4 alkyl; R2=H, C1˜C3 alkyl; Z=(CH2)n or CH2CH(OH)CH2; n=2,3,4; R3, R4=H, alkyl, alkenyl, phenylalkyl, with antiarrhythmic activity in dogs, were prepd. Thus, Grignard reaction of 25.3g Cl(CH2)3NMe2 with 11.6g 2-formyl-5-fluoro-1,1'-biphenyl gave 9.5g N,N-dimethyl-4-hydroxy-(5-fluoror-1,1'-biphenyl-2-yl)butyl amine.

Sphingosine type 1 inhibitors and methods for making and using same

Provided are novel compositions and analogs which are useful in a number of applications, indications and diseases, as well as for monitoring pharmakinetics and patient management. These compounds and analogs are applicable to treating tumors of the central nervous system, e.g., glioblastoma (GBM).

Process for the preparation of sulfonanilide derivatives.

Patent FR2143634B2

Derivatives of n-methylpiperazine

N-METHYL-N''-ETHYL-PIPERAZINES IN WHICH THE ETHYL RADICAL IS B,B-DISUBSTITUTED WITH (1) A PHENYL OR PHENOXYMETHYLENE RADICAL WHICH IS UNSUBSTITUTED OR SUBSTITUTED IN THE RING WITH STRAIGHT OR BRANCHED ALIPHATIC CHAINS HAVING 4 TO 12 CARBON ATOMS OR CYCLOALKYL GROUPS HAVING 5 TO 6 CARBON ATOMS OR WITH 2 OR 3 CHLORINE ATOMS OR WITH 2 CHLORINE ATOMS AND A NITRO GROUP, AND (2) A BENZOLYOXY OR PHENOXYACETYLOXY RADICAL WHICH IS UNSUBSTITUTED OR SUBSTITUTED IN THE RING WITH 1, 2 OR 3 CHLORINE ATOMS OR WITH 2 CHLORINE ATOMS AND A NITRO GROUP OR A BENZYLOXY RADICAL SUBSTITUTED IN THE RING WITH 1, 2 OR 3 CHLORINE ATOMS; AND PHARMACEUTICALLY ACCEPTABLE ACID ADDITION SALTS THEREOF. ALL OF THE COMPOUNDS HAVE ANTIBACTERIAL AND ANTIPROTOZOAN ACTIVITY.

Sphingosine type 1 inhibitors and methods for making and using same

Provided are novel compositions and analogs which are useful in a number of applications, indications and diseases, as well as for monitoring pharmakinetics and patient management. These compounds and analogs are applicable to treating tumors of the central nervous system, e.g. glioblastoma (GBM).

NOVEL PIPERAZINE DERIVATIVES AND THEIR SALTS, THEIR PREPARATION PROCESS AND THEIR APPLICATION IN THERAPEUTICS

Stereoselective alkylation of chiral 2-methyl-4-protected piperazines

1,1:-biphenyl-2-yl alkylamine derivatives

Process for the preparation of aminoacytylenes, or acid addition salts thereof.

Patent SU372806A3

Phenyl-propylamine derivatives

"PROCEDURE FOR THE PREPARATION OF NEW DERIVATIVES OF PHENYLPROPEMLAMINE", useful in therapeutics, especially as a psychostimulatory agent, that responds to the general formula: **(See formula)** wherein R2 represents the hydrogen atom or a halogen atom; A represents the group CH2CH2 or CH = CH; R3 represents the hydrogen atom or a C1-C3 alkyl group; represents a C1-C3 alkyl group identical or different to the alkyl group of R3, R3 and R4 considered together as being capable of forming with the nitrogen atom to which they are attached, a heterocyclic group of 5 to 7 vertices, a heterocyclic group capable of enclosing a second heteroatom, such as O, N, and S in particular, being replaceable; R1 represents the cyclohexyl group, R1 may be phenyl when R2 = H; and its acid addition salts, the aforementioned process being characterized in that, successively, a) according to Mannich an acetophenone of the formula is condensed: **(See formula)** wherein R1 and R2 are defined as above, with formaldehyde and an amine of formula: HHR3R4 (IIa) wherein R3 and R4 is defined as above; b) the amino ketone thus formed is subjected to the action of a reducing agent, preferably a hydride at a temperature below 10ºC in an alcohol; and c) the amino-3 propanol-1 thus formed is subjected to the action of a dehydration agent, especially p-toluene sulfonic acid, to prepare a compound of formula I in which A is CH = CH; and because the unsaturated compound thus formed is hydrogenated if necessary, especially in the presence of platinum oxide to prepare a compound of formula I in which A is CH2CH2, the final product being able to be transformed into which A is CH = CH or CH2CH2, in acid addition salt. (Machine-translation by Google Translate, not legally binding)

Process for the preparation of basic substituted phenylcycloalkenylpropanols

The 1-butyl-2-hydroxyaralkyl piperazine derivatives and the uses as anti-depression medicine thereof

The invention discloses 1-butyl-2-hydroxyl aralkyl piperazine derivatives and their use as antidepressants. The derivatives of the present invention have triple inhibition effect on the reuptake of 5-HT, NA and DA, and can be administrated to the patients in need thereof in form of composition by route of oral administration, injection and the like. Compared with clinically currently used dual targets antidepressants (such as venlafaxine), said derivatives may have stronger antidepression effect, broader indications, faster onset and lower neurotoxicity and side reaction; and said derivatives have stronger antidepression activity, lower toxicity, higher bioavailability, longer half life and better druggablity, compared with aryl alkanol piperazine derivatives and optical isomers thereof disclosed in prior art. The 1-butyl-2-hydroxyl aralkyl piperazine derivative is the free alkali or its salt of a compound of formula below:

Diphenylpropylamines

ABSTRACT OF THE DISCLOSURE The present invention relates to pharmaceutical compositions which on administration to mammals are capable of producing a psychotropic effect and is particular, produce a mood elevating effect without causing substantial side effects such as those associated with anti-cholinergic agents. Accordingly, the present invention provides pharmaceutical compositions which comprise pharmaceutically acceptable carriers in associa-tion with compounds of the formula (III): (III) wherein R1 is hydrogen atom or a group R9 or CO.R9 wherein R9 is C1=6 alkyl, phenyl or benzyl group or such a group .omega.-substituted by a group NR10-R11 where R10 is hydrogen atom or a methy, ethyl or benzyl group and R11 is a hydrogen atom or a methyl or ethyl group or is attached to R10 so that NR10R11 is a pyrrolidyl, piperidyl, morpholino or hexamethylenimino group; R2 is a hydrogen atom or a methyl or ethyl group; R3 is a hydrogen atom or a methy, ethyl, propyl or benzyl group; R4 is a hydrogen atom or a methyl or ethyl group or is attached to R3 so that NR3R4 is a pyrrolidyl, piperidyl, morpholino, N-methyl-piperazino or hexamethylenimino group; R5 is a hydrogen, fluorine, chlorine or bromine atom or a methyl, ethyl, propyl, butyl, benzyl, trifluormethyl, hydroxy, methoxy, ethoxy, propoxy, benzyloxy, acetoxy, propionoxy, amino, methylamino ethylamino, dimethylamino, diethylamino, carboxyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, nitro or methylthiol group; R6, R7 and R8 which may be the same or different are each a hydrogen, flourine, chlorine or bromine atom or a methyl, ethyl, methoxy, ethoxy, acetoxy, hydroxy or trifluoro-methyl group; or salt or solvent thereof. The process of preparation comprises the condensation of an amine of the formula HNR3R4 with a compound of the formula (V) :

(1,1-BIPHENYL-2-YL) -PROPYL- AND BUTYLAMINES AND PHARMACEUTICAL COMPOSITION CONTAINING THEM.

New heart regulators.

N-phenyl-N'-phenylpropylpiperazine derivatives and process for their preparation

Det beskrives et N-fenyl-N'-fenylpropylpiperazin-derivat med formel (1): (1) (hvor R1 utgjør en lavere alkylgruppe; R2 utgjør en lavere alkoksygruppe; og R3 utgjør en cyanogruppe, en karboksylgruppe eller en indolkarbonylgruppe); et medikament; og en fremgangsmåte for fremstilling av derivatet. Forbindelsen har potent a,- adrenoreseptor-blokkerende virkning, og er således egnet for forhindring eller behandling av hypertensjon, kongestiv hjertesvikt, myokardiskemi, arytmi, angina pectoris, og urinobstruksjon og pollakisuri forårsaket av benign prostatahyperplasi.

Process for obtaining novel 1,3-aminoalochol-benzoates

Process for the preparation of substituted diphenylalkylamines

Patent FR7083M

Patent FR1599658A

Saccharine salts of substituted hydroxypropylamines

The method of obtaining the derivatives of 1,3-amino alcohols

N-phenyl-n'-phenylpropylpiperazine derivatives and process for the preparation thereof

Process for the preparation of novel substituted diphenylethylamines

Processes for the preparation of enamines

The invention disclosed in this document is related to the field of processes for the preparation of enamines wherein R1, R2, R3, R4, R5, and further information are disclosed herein.

Patent FR2111704B1

Process for preparing novel n-substituted derivatives of 1-(4'-alkylthiophenyl)-2-amino-1,3-propanediol

"1-(4'-ALKYLTHIOPHENYL)-2-AMINO-1,3-PROPANEDIOL N-SUBSTITUTED DERIVATIVES". ************** ABSTRACT N-substituted derivatives of 1-(4'-alkylthiophenyl)-2-amino--1,3-propanediol, their salts with pharmaceutically acceptable organic and inorganic acids, processes for preparing them, phar-maceutical compositions containing them and intermediates useful in the preparation thereof. The novel derivatives according to this invention are endowed with calcium antagonist activity and are useful as antiarrhyth-mic and vasodilating agents.

Substituted hydroxyprophylamine derivatives

1-¬(1,1-diphenyl)-1-alkenyl| pierazine derivatives, method of preparation and pharmaceutical compositions in which they are present

ABSTRACT OF THE DISCLOSURE The invention relates to 1-[(1,1-diphenyl)-1-alkenyl]piperazine derivatives corresponding to general formula I: (I) in which R1, R2, R3, R4 and R5, which are identical or different, represent a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkenyl group, a lower alkoxy group or the trifluoromethyl group; n is an integer between 1 and 3; m is an integer from 0 to 3; Z represents a hydrogen atom, a lower alkyl group or an aryl group of the formula: in which R6 has the same meaning as R1, R2, R3 or R4; and A is an oxygen atom or a group

Novel process for preparation of optically pure norephedrine and its derivatives

The present invention relates to a novel process for preparation of norephedrine and its derivatives. The present invention also relates to a process for separation of individual isomers of norephedrine and its derivatives using suitable chiral resoluting agents.

Patent FR5170M

Piperazines and process for their manufacture

New compounds of formula <FORM:1048903/C2/1> wherein Ph represents halophenyl, dihalophenyl or trifluoromethylphenyl, R represents lower (i.e. 1-7C) alkyl, R1 represents hydrogen or methyl and Ar represents phenyl, lower alkyl phenyl, lower alkoxy phenyl or halophenyl, and their acid addition salts, are prepared by reaction of N-Ar-C-R1-piperazines with compounds Ph-CHOR-CH2-Y where Y is a reactive esterified hydroxyl group. Optical isomers are mentioned. Haloether starting materials Ph-CHOR-CH2-hal are prepared by reaction of Grignard reagents of Ph-halides with alkoxy-ethylene-1, 2-dihalides. Pharmaceutical compositions comprise the new compounds with carriers. Conventional oral, parenteral and rectal preparations are mentioned. The compounds have anti-inflammatory, anti-hypertensive, adrenolytic, diuretic and saliuretic activities.

Patent FR2218887A1

Phenylpropanolamines, their preparation and their use

ABSTRACT OF THE DISCLOSURE: Phenylpropanolamines of the formula I I where R1 is hydrogen or halogen, R2 is hydrogen, a saturated or unsaturated hydrocarbon radical of not more than 15 carbon atoms or phenyl, R3 is hydrogen, a saturated or un-saturated hydrocarbon radical of not more than 3 carbon atoms, C1-C4-acyl, benzoyl, C2-C4-carbalkoxy or a carb-oxamido group -CO-NHR6, where R6 is C1-C4-alkyl, R4 is hydrogen or halogen, R5 is dimethylamino, piperidino or pyrrolidino and X is oxygen or sulfur, their salts with physiologically tolerated acids and their preparation are described. These compounds are useful for treating psycho-logical illnesses, especially depression.

Patent FR2495136B1

Methods of producing enamines

Изобретение относится к усовершенствованному способу получения енаминов, предпочтительно 1-(3-метилсульфанил-бут-1-енил)пирролидина. Енамины могут быть использованы для различных реакций, включая реакцию восстановления для получения аминов. Способ получения енаминов осуществляют по следующей схеме Способ, включает (A) контактирование первой смеси со второй смесью в реакционной зоне. При этом (1) указанная первая смесь содержит карбонил (т.е. альдегид или кетон), имеющий следующую формулу (a), где один из R1 и R2 представляет собой C 1 -C 6 алкил, а другой представляет собой S-R6, где каждый R6 представляет собой C 1 -C 6 алкил, и (b) где R3 представляет собой Н, и (2) где указанная вторая смесь содержит неполярный растворитель с высокой точкой кипения и амин, имеющий следующую формулу , где R4 и R5, взятые в совокупности с N, представляют 5- или 6-членное насыщенное или ненасыщенное кольцо. Способ также включает (B) реакцию в указанной реакционной зоне указанного амина и указанного карбонила с образованием енамина и H 2 O, в условиях азеотропной дистилляции, при (1) давлении от 100 Паскалей (Па) до 120000 Па, и (2) температуре ниже температуры термического разложения указанного енамина в процессе указанной реакции; (C) удаление газовой фазы, включая указанный неполярный растворитель с высокой точкой кипения, амин, и H 2 O; (D) конденсацию указанной газовой фазы со стадии (С) с образованием конденсата; и (E) контактирование указанного конденсата со стадии (D) с восстанавливающей смесью, содержащей H 2 O и средство для удаления амина для получения отдельной смеси, содержащей указанный амин. При этом возможно проведение стадии (F) для необязательного удаления указанного амина со стадии (Е) обратно в указанную реакционную зону. Преимущественно на стадии А) применяют эквимолярные количества указанного амина и указанного карбонила. Молярное отношение амина к карбонилу может составлять от 0,9 до 1,2.Указанный неполярный растворитель с высокой точкой кипения является ...

Amino alcohols and salts thereof

Patent FR2350100B1

NOVEL SULFUR NITROETHYLENIC DERIVATIVES AND THEIR APPLICATIONS AS NO-SYNTHASE INHIBITORS

Patent DE3326148C2

ANTIMICROBIAL AROMATIC DERIVATIVES AND PROCEDURES FOR PREPARING THEREOF AND MENTALS CONTAINING THE DERIVATIVES

Procedure for obtaining piperacinic compounds (Machine-translation by Google Translate, not legally binding)