СОЕДИНЕНИЯ ЦЕФЕМА СОЕДИНЕНИЯ ЦЕФЕМА

... 1. Соединение формулы где A представляет собой низший алкилен или низший алкенилен; R1 представляет собой низший алкил, гидрокси(низший)алкил, защищенный гидрокси(низший)алкил, амино(низший)алкил или защищенный амино(низший)алкил, и R2 представляет собой водород или аминозащитную группу, или R1 и R2 связаны друг с другом и образуют низший алкилен; R3 и R5 независимо представляют собой амино или защищенную аминогруппу; и R4 представляет собой карбокси или защищенную карбоксигруппу. или его фармацевтически приемлемая соль. 2. Соединение по п.1, где R1 представляет собой низший алкил, гидрокси(низший)алкил, арил(низший)алкилокси(низший)алкил, амино(низший)алкил или ациламино(низший)алкил, и R2 представляет собой водород, арил(низший)алкил или ацил, или R1 и R2 связаны друг с другом и образуют низший алкилен; R3 и R5 независимо представляют собой амино или ациламино; и R4 представляет собой карбокси или этерифицированную карбоксигруппу, или его фармацевтически приемлемая соль. 3. Соединение ...

CПOCOБ ПOЛУЧEHИЯ CЛOЖHЫX ЭФИPOB 3-ЭKЗOMETИЛEHЦEФAMCУЛЬФOKCИДA

СПОСОБ ПОЛУЧЕНИЯ ЦЕФАЛОСПОРИНОВ

Способ получения производных пенама

Способ получения 3-окси-3-метил-7-аминоцефалоспоринов

Способ получения производных цефалоспорина

Способ получения производных цефалоспорин-1-оксида

СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНЫХ ЦЕФАЛОСПОРИН-1-ОКСВДА общей формулы t г HfN -A ;-fe-HH v; « еоон а-с-соон 4, где R, и R - метил или R и R вместе - ,3-пропилен; R - 1Н-1,2,4-триазол-З-ил, 5-амиио-1Н-1,2,4-триазол-3-ип , 2-амино-1,3,4-тиади .азол-5-ш1, 2-Ч еркапто1 ,3,4-тиадиазол-5-Ш1 :шга З-оксипирндил-2, . в виде син-изомеров о т л и ч а ющ и и с я тем, что сложный трет.бутиловый эфир 7-амино-З-бромметил-Зцефем-4-карбоновой кислоты-1-оксид подвергают ацилированию кислотой общей формулы .S . еоон СН R. н. О-cJ-doo-d-cJH, Rt СНз где R. и Rj имеют указанные значения; R.-группа, защищающая аминогруппу , такая как тритил, в виде син-изрмера, в среде инертного органического ряст ворителя, такого как метиленхлорид, в присутствии карбодиимида и органического основания при комнатной температуре, образующийся продукт .подвергают взаимодействию с гетероциклическим тиолом формулы RjSH, где Rj имеет указанные значения, СО в среде инертного органического 00 00 растворителя, такого как диметилформамид , ...

3-HALOCEPHAME UND DEREN ISOMERE SOWIE VERFAHREN ZUR HERSTELLUNG DERSELBEN

Antibakterielle Cephalosporine

2-amino-4,5,7,8-tetrahydro-6h-thiazolo-or oxazolo(5,4-d) - azepines - as hypotensive, antiphlogistic, sedative and bechic agents

Cpds (I) and their salts. (where R1 is H, 1-4C alkyl opt. substd. by OH, allyl, cycloalkyl, hexahydrobenzyl, phenyl, phenethyl or benzyl opt. substd by 1 or 2 halogen, 1-3-MeO, Cf3 or 1-3C alkyl, R2 is (when X is S) H, 1-5C alkyl, allyl, cycloalkyl, phenyl, benzyl, or phenethyl, and (when X is O) H) are prepd by reacting a hexahydroazepin-4-one with a urea or thiourea in the presence of halogen or a halo hydroazepin-4-one with a urea or thiourea or a 4-alkoxy-tetrahydroazepine with a thiourea in the presence of a halogen or by reducing (I R1 or R2= acyl) by hydroxyalkylating (I R1=He with an epoxide or by diacylating a 6-acylamino deriv. of (I). Thus 1-benzyl-5-bromohexahydro-1H-azepinone-(4)-and thiourea gave (I R1=benzyl R2=N, X=S).

Verfahren zur Synthese von Cephamen

A process for preparing a compound of formula (I): wherein each of R1 and R2 is, independently, hydrogen or an organic residue comprises reacting a compound of formula II: wherein R1 and R2 are as above defined, with a radical initiator, in the presence of molecular oxygen, typically pure O2 or air. The compounds of the formula (I) are useful intermediates for the production of many useful beta -lactam antibiotics.

VERFAHREN UND ESTERDERIVATE ZUR HERSTELLUNG VON CEPHALOSPHORINEN

SS-LACTAM-ANTIBIOTIKA, VERFAHREN ZUR HERSTELLUNG UND IHRE VERWENDUNG ALS ARZNEIMITTEL

7-ISOCYANATO-CEPHALOSPORANSAEUREDERIVATE

N-DEACYLATION OF 7-ACYLAMIDO-3-HYDROXY-METHYL CEPHALOSPORINS

A process for the N-deacylation of 7-acylamido-3-hydroxymethylcephalosporins, in which, in a multi-stage process, the 7-amino group is liberated and the hydroxyl group in the 3-hydroxymethyl group is replaced by a halogen atom. First, the starting compound is reacted with an imide-halide-forming reagent in the presence of a base and thereafter the imide-halide formed is reacted with an iminoether-forming compound, after which the iminoether thus obtained is cleaved hydrolytically. The products of the process may be used as starting material or as precursors for the preparation of antibiotically active cephalosporins. To prepare cephaloridine and cefalozine, the product of the process is first N-acylated in an appropriate manner, after which the halogen atom in the 3-halogenomethyl group is replaced by the appropriate radical.

DERIVATIVES OF CEPHALOSPORANIC ACID

... 1341827 Silyl derivatives of 7-isocyanatocephalosporanic acid KONINKLIJKE NEDERLANDSCHE GIST-EN SPIRITUSFABRIEK NV 18 Dec 1970 [18 Dec 1969] 61842/69 Heading C3S [Also in Division C2] The invention comprises 7-isocyanatocephalosporanic acid derivatives of the formula wherein R represents a hydrogen atom, a protected hydroxy group or an acyloxy group, and E represents a carboxylic protecting group such as a silyl group of general formula (R 1 ) 3 Siin which R 1 represents C 1 -C 6 alkyl, phenyl or phenyl (C 1 -C 6 ) alkyl. In particular E may represent the trimethylsilyl group. The above compounds also include those in which R is a protected hydroxy group of formula -OSi(R 1 ) 3 in which R 1 is C 1 -C 6 alkyl, phenyl or phenyl (C 1 -C 6 ) alkyl. Examples of such compounds are trimethylsilyl esters of 7-isocyanato-cephalosporanic and 7-isocyanatodesacetoxycephalosporanic acid. The 7-isocyanate cephalosporanic acid derivatives are prepared by reacting phosgene with a cephalosporanic acid derivative ...

CEPHALOSPORANIC ACID DERIVATIVES

PROCESS FOR THE SYNTHESIS OF CEPHAMS

CHEMICAL COMPOUNDS

Process for preparing 3-exomethylenecepham derivatives

This invention provides a process for preparing 3-exomethylenecepham derivatives represented by the formula wherein R1 is arylacetylamino, aryloxyacetylamino, heterocyclic acetylamino or imido, and R2 is a protective group for the carboxyl, the process being characterized in that a 3-halomethylcephem compound represented by the formula wherein R1 and R2 are as defined above, and X is a halogen atom is electrolyzed in a mixture of a hydrophilic organic solvent and water.

Novel 3-vinyl-cephalosporins and their preparation

Organic compounds

2-SUBSTITUTED CEPH-3-EM-4-CARBOXYLIC ACID DERIVATIVES

Cephalosporin analogues which have antibiotic activity and the following formula I in which the symbols R, R<1>, R<2> and Z have the meaning stated in Claim 1 are prepared by eliminating from a corresponding ceph-3-em-4-carboxylic acid which is esterified by an alcohol, phenol, silanol or stannanol, or protected by an anhydride group, the said group. Particularly important in respect of their antibiotic activity are those compounds whose side chain present in position 7 has an oximino functionality. These include compounds of the formula I in which R<1> is a group of the formula R<9>CONH where R<9> is an alpha -aryl- or alpha -heteroarylalpha -oximinomethyl, alpha -aryl- or alpha -heteroarylalpha -alkoxyiminomethyl or alpha -aryl- or alpha -heteroarylalpha -( alpha -carboxyalkoxyimino)methyl group, and, in particular, a syn-2-(2'-thienyl)- or a syn-2-(2'-furyl)-2-oximinoacetamido group or its methoxyimino, carboxymethoxyimino or 2-carboxy-2-propoxyimino derivatives. These compounds are ...

Methods of preparation of derived from acid alkyl lower - 2 or 3 - cephem-4-carboxylic, new products thus obtained and their use as products with antimicrobic activity.

New derivatives of cephalosporines substituted in position 3 by a group heterocycle thiométhyl; method of preparation of the aforesaid compounds and pharmaceutical compositions while containing.

Method of preparation of 3-halocéphalosporines.

Method of preparation of made up B-lactam.

Method of preparation of 3-hydroxycéphalosporines.

Method of preparation of ethers of cephalosporine.

3-methylene cephalosporines.

Method of preparation of composed of acids 2-alkyl inferior-7-substituted-2 or 3-céphem-4 carboxylic and industrial products new.

Method of preparation of 3-exométhylènecépham-sulfoxides.

Derived céphem and their preparation.

VERFAHREN ZUR HERSTELLUNG VON 3-METHYLENCEPHAMSULFOXIDEN

PROCEDURE FOR THE PRODUCTION OF NEW CEPHEMVERBINDUNGEN AND THEIR PHARMACEUTICAL HARMLESS ONE SALTS

VERFAHREN ZUR HERSTELLUNG VON NEUEN CEPHALOSPORINDERIVATEN

VERFAHREN ZUR HERSTELLUNG VON CEPHALOSPORINEN

VERFAHREN ZUR HERSTELLUNG VON NEUEN 3,4-DICARBOXYCEPHALOSPORINEN

VERFAHREN ZUR HERSTELLUNG VON NEUEN O-SUBSTITUIERTEN 7BETA-AMINO-CEPHEM-3-01-4-CARBONSAUREVERBINDUNGEN

VERFAHREN ZUR HERSTELLUNG VON NEUEN ENOLDERIVATEN

VERFAHREN ZUR HERSTELLUNG VON 7-AMINO-3-HALOGENMETHYL-CEPHALOSPORANSAUREESTERN

VERFAHREN ZUR HERSTELLUNG NEUER CEPHALOSPORINE

VERFAHREN ZUR HERSTELLUNG VON NEUEN HALOGENIERTEN CEPHAMDERIVATEN

PROCEDURE FOR THE PRODUCTION OF AZETIDINDERIVATEN

PROCEDURE FOR THE PRODUCTION OF NEW CEPHEMVERBINDUNGEN AND THEIR PHARMACEUTICAL HARMLESS ONE SALTS

NEW CEPHALOSPORIN CONNECTIONS AS WELL AS THESE CONTAINING PHARMACEUTICAL PREPARATIONS

PROCEDURES FOR THE PRODUCTION OF NEW ONES PENICILLAN OR CEPHALOSPORANSAUREDERIVATEN

PROCEDURE FOR THE PRODUCTION OF NEW ENOLDERIVATEN

PROCEDURE FOR THE PRODUCTION OF NEW CEPHALOSPORINDERIVATEN

PROCEDURE FOR the PRODUCTION OF 7BETA-AMINO-3-CEPHEM-4-CARBONSAUREVERBINDUNGEN

PROCEDURE FOR the PRODUCTION OF 3-EXOMETHYL ENCEPHAMSULFOXIDESTERN

PROCEDURE FOR the PRODUCTION OF 7-AMINO-3-HALOGENMETHYL-CEPHALOSPORANSAUREESTERN

INTERMEDIATE PRODUCTS WITH THE CEPHALOSOPRINHERSTELLUNG

PROCEDURE FOR THE PRODUCTION OF NEW CEPHAM CONNECTIONS

PROCEDURE FOR THE PRODUCTION OF NEW CEPHEM AND CEPHAMVERBINDUNGEN

BETA LACTAM ANTIBIOTICS, PROCEDURES FOR THE PRODUCTION AND YOUR USE AS DRUGS.

CEPHALOSPORINDERIVATE SUBSTITUTES ABSTENTION PHARMACEUTICAL CONNECTIONS IN POSITION 3 OF A THIOMETHYLHETEROCYCLI GROUP, PROCEDURE FOR YOUR PRODUCTION AND IT.

3,7-DISUBSTITUIERTE-2 OR -3-CEPHEM-4CARBONS [URE CONNECTIONS, IT ABSTENTIONS PHARMACEUTICAL COMPOSITIONS AND PROCEDURES TO THEIR PRODUCTION.

PROCEDURE FOR THE PRODUCTION OF NEW CEPHALOSPORINVERBINDUNGEN

OUTPUT PRODUCTS FOR THE PRODUCTION OF CEPHEM CONNECTIONS AND PROCEDURES FOR YOUR PRODUCTION.

SULFATE OF CEPHEMVERBINDUNG

Procedure for the production of new Azepin derivatives and their acid addition salts

PROCEDURE FOR THE PRODUCTION OF AMINOPYRROLIDINDERIVATEN

Procedure for the production of new Cephalosporinverbindungen

Procedure for the production of new Azepin derivatives and their acid addition salts

Procedure for the production of new 3-Methylencephalosporinen

Procedure for the production of new Cephalosporinverbindungen

PROCEDURE FOR the PRODUCTION OF NEW ONE 3,4-DICARBOXYCEPHALOSPORINEN

VERFAHREN ZUR HERSTELLUNG VON PENICILLIN- UND CEPHALOSPORINVERBINDUNGEN

BETA LAKTAM AND CEPHAM CONNECTIONS AND YOUR PRODUCTION

IMPROVED PRODUCTION OF CEFTIOFUR ZWISCHENPRODKTEN

THIOXIME CEPHALOSPORIN AND PENICILLIN DERIVATIVES

B-LACTAM ANTIBIOTIC

CEPHALOSPORIN COMPOUNDS

Therapeutic azide compounds

DE-ESTERIFICATION PROCESS FOR CEPHALOSPORINS

2-METHYLCEPHALOSPORINS AND PRODUCTION THEREOF

CEPHALOSPORINS, PROCESSES FOR PRODUCING THE SAME, ANTIBACTERIAL AGENT CONTAINING THE SAME, INTERMEDIATES THEREOF AND PROCESS FOR PRODUCING THE INTERMEDIATES

TRICYCLIC PYRIDINE DERIVATIVES

The novel compounds of the general formula I wherein Ql and the nitrogen atom together signify a group of the formula >N-CH2CH2- (a), >N-CH2CH2CH2- (b), >N-C=CH- (c), >N-CH2-CH3CH- (d), >N-CH2-S(O)p- (e), >N-CH2CH2-S(O)p- (f) or >N-CH=CH-S(O)p- (g), P signifies the number 0, 1 or 2 and Ra signifies a phenyl, pyridyl or thienyl group which is optionally substituted by halogen, trifluoromethyl, nitro, lower alkyl or lower alkoxy, and either Rb and Rc each signify hydrogen, halogen, trifluoromethyl, lower alkyl, lower alkoxy or nitro and the dotted line signifies an optional bond, or Rb and Rc together with the carbon atom denoted by .alpha. signify a group of the formula >C.alpha.-S-CH=CH- (h), >C.alpha.-CH=CH-S- (i) or >Ca-CH=CH-CH=CH- (j) which is optionally substituted by halogen, trifluoromethyl, lower alkyl, lower alkoxy, nitro, amino or mono- or di(lower alkyl)amino, and the dotted line signifies an additional bond, Rd signifies the group of the formula -(A1)m-(CO)n-(Q2A2)q-R1 ...

2-LOWER ALKYL-7-SUBSTITUTED-2 OR 3-CEPHEM-4-CARBOXYLIC ACID COMPOUNDS AND PROCESSES FOR THE PREPARATION THEREOF

New 2-lower alkyl-7-substituted-2-or 3-cephem-4-carboxylic acid compounds are provided of the formula: wherein R1 is (C1 to C6)alkyl, R2 is carboxy or a protected carboxy group, R3 is amino or a protected amino group, and A is hydroxyimino(C1 to C6)alkylene or (C1 to C6)alkoxyimino(C1 to C6)alkylene, and the tautomeric forms and pharmaceutically acceptable salts thereof; the new compounds have antimicrobial activity and inhibit the growth of both gram positive and gramnegative bacteria.

PROCESS FOR PRODUCING 7-(SUBSTITUTED)AMINO-3- SUBSTITUTED THIOMETHYL CEPHEM CARBOXYLIC ACIDS

... 74/98 NOVEL PROCESS FOR PRODUCING 7-(SUBSTITUTED)AMINO-3-SUBSTITUTED THIOMETHYL CEPHEM CARBOXYLIC ACIDS This disclosure relates to a novel process for producing 7-(substituted)amino-3-substituted thiomethyl cephem carboxylic acids which are intermediate products of cephalosporins being valuable antibacterial compounds for use in mammals including man.

O-SUBSTITUTED 7(BETA)-AMINO-3-CEPHEM-3-OL-4-CARBOXYLIC ACIDS

ACIDES 7-(BETA)-AMINO-CEPHAM-3-ONE-4-CARBOXYLIQUES

PROCESS FOR THE MANUFACTURE OF METHYLENE COMPOUNDS

NOVEL THIOESTER DERIVATIVES OF THIAZOLYL ACETIC ACID AND THEIR USE IN THE PREPARATION OF CEPHALOSPORIN COMPOUNDS

The present invention provides novel thioester derivatives of thiazolyl acetic acid of the general formula (I), also, the invention provides a method for preparation of the thioester derivatives and reaction of the thioester derivatives with cephem carboxylic acids to produce cephalosporin antibiotic compounds having general formula (II).

TRICYCLIC COMPOUND HAVING SULFINYL OR SULFONYL

The present invention provides a compound exhibiting a strong antimicrobial spectrum against various bacteria, including gram-negative bacteria, or a pharmaceutical composition having an antimicrobial activity against carbapenem-resistant bacteria. Provided is a compound represented by formula (I), an ester thereof or a pharmaceutically acceptable salt thereof, or a hydrate thereof. (I) (In the formula, -W- is -S(=O)- or -S(=O)2-, -T- is -CR4AR4B- or -CR5AR5B-CR6AR6B-, each of R4A, R4B, R5A, R5B, R6A, and R6B is independently a hydrogen atom, etc., R1 is a substituted or unsubstituted heterocyclic group, etc., each of R2A and R2B is independently a hydrogen atom, etc., or R2A and R2B together form a substituted or unsubstituted methylidene, etc., R3 is a hydrogen atom, etc., R11 is a carboxy, etc., and each of R7A and R7B is independently a hydrogen atom, etc.) ...

7-Amino-3-methylene-cephams prepn. - by reducing 7-amino-3-acyloxymethyl-3-cephems, used as inters for antibiotic cephalosporins

Cpds. of formula (I) (where R is a second bond between the attached C atom and posn. E, with only a single bond between posn. 3 and 4; R1 is H or an amino-protecting gp.; R2 is H or an acyl; or R1 and R2 together represent a divalent amino-protecting gp.; and R3 is OH, or together with the carbonyl gp. forms a protected carboxyl residue), their 1-oxides and salts, are prepd. by reducing cpds. (II) (I; R is acyloxy; and R3 is as before or R+R3 is -O-), or their oxides or salts with a metal (amalgam) having a normal potential of -2.4 to -0.40 volt (pref. Al) at pH 1-8 in the presence of water. (I) and their l-oxides and salts are inters. for antibiotic cephalosporins, and are readily isomerizable to 7-amino-3-methyl-3-cephems.

Verfahren zur Herstellung thiaheterocyclischer Verbindungen

2-thiacephalosporanic acid derivs - useful as pharmaceuticals and intermediates

Cpds. of formula (I): (where Ra1 = Hb or an N-protecting gp; Rb1 = H or Ra1 + Rb1 = an org. ylidene gp. R2 = H or an ester-forming goup (RA2); R3 = H or a C-bonded org. gp. Ra and Rb are H or from a C-C bond) and their S-oxides and salts are prepd. by oxidn. of a cpd. (II) or acid treatment of a cpd. (III) where X = opt. substd. methylene; R1o = H or a removable org. gp; RB2 = RA2 or an org. silyl orstannyl gp; Aco1 is a removable acyl gp) opt. followed by removal of the ylidene gp, saponification, esterification, conversion into the S-oxide and/or salt formation. (I) are pharmaceuticals or intermediates therefor e.g. (I) where Ra1 is an N-acyl deriv. of a penicillin or cephalosporin cpd. are broad-spectrum antibacterial.