7-position Substituent Contains Hetero Ring Patents (Class 540/225)
-
Patent number: 4735938Abstract: Antibiotically active penicillins and cephalosporins of the formula ##STR1## in which Z is hydrogen or lower alkoxy,n is 1 or 2,Y, in the form of the free acid, is ##STR2## X is --S--, --n--, --SO-- or --SO.sub.2 --, T is an organic radical, hydrogen or halogen,A is hydroxyl, optionally substituted alkyl, a substituted or unsubstituted phenyl ring, an optionally substituted polycyclic aromatic ring, an optionally substituted 5-membered or 6-membered heterocyclic ring with nitrogen, oxygen and/or sulphur as hetero atoms in the ring, or an optionally substituted polycyclic heterocyclic ring,or non-toxic pharmaceutically tolerated salts thereof.Type: GrantFiled: July 10, 1986Date of Patent: April 5, 1988Assignee: Bayer AktiengesellschaftInventors: Michael Boberg, Karl G. Metzger, Hans-Joachim Zeiler
-
Patent number: 4736026Abstract: The invention relates to a process for producing a cephalosporin of the formula ##STR1## by reacting the compound ##STR2## with the compound ##STR3## in the presence of boron trifluoride or a complex thereof.Type: GrantFiled: June 24, 1986Date of Patent: April 5, 1988Assignee: Toyama Chemical Co., Ltd.Inventors: Hiroyuki Imaizumi, Takihiro Inaba, Seishi Morita, Ryuko Takeno, Yoshiharu Murotani, Hirohiko Fukuda, Junichi Yoshida, Kiyoshi Tanaka, Shuntaro Takano, Isamu Saikawa
-
Patent number: 4734408Abstract: The crystalline sulfate dihydrate, dimethylacetamide hydrate and dimethylformamide hydrate solvates of the antibiotic syn-7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(3-methyl-3H-imi dazolo[4,5-c]pyridinium-5-ylmethyl)-3-cephem-4-carboxylate are provided.Type: GrantFiled: December 17, 1986Date of Patent: March 29, 1988Assignee: Eli Lilly and CompanyInventor: Allen S. Katner, deceased
-
Patent number: 4734407Abstract: Antibacterially active and animal growth-regulating novel .beta.-lactam compounds of the formula ##STR1## in which R.sup.1 represents an optionally substituted radical of the formula ##STR2## Z represents oxygen, sulphur or --N--R.sup.Type: GrantFiled: March 10, 1986Date of Patent: March 29, 1988Assignee: Bayer AktiengesellschaftInventors: Gunter Schmidt, Hans-Joachim Zeiler, Karl G. Metzger
-
Patent number: 4727071Abstract: A cephalosporin compound of the formula: ##STR1## wherein R.sup.1 is hydrogen or lower alkyl;R.sup.2 is acetoxy or (1-methyl-1H-tetrazol-5-yl)thio, andR.sup.3 is carboxy; orR.sup.2 is a group of the formula: ##STR2## R.sup.3 is --COO.sup.- and Y is hydrogen, hydroxymethyl or carbamoyl; andn is an integer of 2 or 3,or a pharmaceutically acceptable salt thereof and processes for their preparation are disclosed. Said cephalosporin compound is useful as an antimicrobial agent.Type: GrantFiled: March 4, 1986Date of Patent: February 23, 1988Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Toyonari Oine, Hiroshi Sugano, Yoshihisa Yamada, Totaro Yamaguchi, Satoshi Ohshima
-
Patent number: 4717768Abstract: A process for the separation of a mixture of syn and anti oxime isomers one from the other which comprises adsorbing said mixed oxime isomers onto a non-functional macroreticular adsorption resin, and eluting said resin to yield at least one eluate fraction containing one of said isomers while being substantially free of the other of said isomers.The application of this process to the separation of syn and anti isomers of cephalosporin compounds possessing an oxime grouping in a side-chain in the 7.beta.-position, and of acids corresponding to this 7.beta.-side chain, is described.Type: GrantFiled: September 7, 1984Date of Patent: January 5, 1988Assignee: Glaxo Group LimitedInventors: Colin Robinson, David T. Eastlick, Audrey J. Bownass
-
Patent number: 4704457Abstract: A compund having the formula ##STR1## can be prepared by coupling a compound having the formula ##STR2## or a salt thereof, with a compound having the formula ##STR3## to yield a compound having the formula ##STR4## and oxidizing that compound to yield the desired compound; wherein R is hydrogen or an amino protecting group;R.sub.1 is hydrogen, methly or ethyl;M.sup..sym. is an inorganic cation or a substituted ammonium ion; andM.sub.1.sup..sym. is hydrogen, an organic cation, or a substituted ammonium ion.Type: GrantFiled: June 21, 1982Date of Patent: November 3, 1987Assignee: E. R. Squibb & Sons, Inc.Inventors: Jerome L. Moniot, Christopher M. Cimarusti, Rita T. Fox
-
Patent number: 4703118Abstract: The present invention provides a process for preparing a 3-iodomethyl cephalosporin by treating a bis(trialkylsilyl)-7-amino-4-carboxylic acid-3-substituted cephalosporin derivative with a trialkylsilyl iodide derivative.Type: GrantFiled: April 8, 1985Date of Patent: October 27, 1987Assignee: Eli Lilly and CompanyInventors: Gary E. Lord, Robert M. Metzler, David D. Wirth
-
Patent number: 4695627Abstract: A process for the preparation of 7.beta.-acylamino-3-substituted-3-cephem-4-carboxylic acid compounds comprising reacting at -70.degree. C. to 0.degree. C. in an inert organic solvent phosphorus pentachloride with a cephalosporin compound in the presence of an olefinic compound having at least one carbon-carbon double bond having not more than three hydrogen atoms attached thereto capable of removing chlorine at least in part by addition to a carbon-carbon double bond.Type: GrantFiled: September 21, 1984Date of Patent: September 22, 1987Assignee: Gist-Brocades N.V.Inventors: Jan Verweij, Herman H. Grootveld, Henri G. J. Hirs, Gerardus J. Van Veen, Jan Kalter, Peter W. Henniger
-
Patent number: 4692443Abstract: Cephalosporin compounds substituted in the 7-position by a 2-(5- or 6-membered heterocyclic)-2-oximinoacetylamino group and in the 3-position with an imidazolo, oxazolo or thiazolopyridinium-methyl group are broad spectrum antibiotics highly effective in combating bacterial infections of gram-negative and gram-positive microorganisms. The cephalosporins are best prepared by reacting a silylated 7-[2-(heterocyclic)-2-oximinoacetylamino]-3-iodomethyl-3-cephem-4-carboxyl ic acid with an imidazolopyridine, and oxazolopyridine or a thiazolopyridine. Pharmaceutical formulations comprising a compound of the invention and a method for treating bacterial infections comprising their use are also provided.Type: GrantFiled: December 10, 1984Date of Patent: September 8, 1987Assignee: Eli Lilly and CompanyInventor: Allen S. Katner
-
Patent number: 4692516Abstract: Process for the preparation of cephem compounds of the formula ##STR1## wherein R is optionally substituted aminothiazolyl or amino-1,2,4-thiadiazolyl, A is optionally substituted pyridinium, R.sup.1 is hydrogen or methoxy and R.sup.2 are special aliphatic substituents, by a nucleophilic replacement in the substituent in 3-position in the presence of tri-C.sub.1 C.sub.4 -alkyl iodosilane.Type: GrantFiled: May 7, 1984Date of Patent: September 8, 1987Assignee: Hoechst AktiengesellschaftInventors: Reiner Kirrstetter, Walter Durckheimer, Rudolf Lattrell, Wilfried Schwab
-
Patent number: 4692518Abstract: Crystalline (7R)-7-amino-3-(1'-pyridiniummethyl)-3-cephem-4-carboxylate monohydrate compound is an intermediate in the synthesis of the cephalosporin antibiotic ceftazidime.Type: GrantFiled: November 6, 1985Date of Patent: September 8, 1987Assignee: Eli Lilly and CompanyInventor: Gary E. Lord
-
Patent number: 4691014Abstract: A cephalosporin compound having the formula: ##STR1## wherein R.sub.1 is a hydroxy group, a lower alkanoyloxy group or a lower alkoxycarbonyloxy group, R.sub.2 is a hydrogen atom, a hydroxy group, a lower alkanoyloxy group or a lower alkoxycarbonyloxy group, R.sub.3 is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkenyl group, a lower alkoxy group or --CH.sub.2 R.sub.7 (wherein R.sub.7 is a hydrogen atom, an azido group, a lower alkanoyloxy group, a carbamoyloxy group, a substituted or unsubstituted pyridinium group or a substituted or unsubstituted heterocyclic thio group), R.sub.4 is a hydrogen atom or a carboxy-protecting group, each of R.sub.5 and R.sub.6 is a hydrogen atom or a lower alkyl group, or R.sub.5 and R.sub.6 form a cycloalkylidene group together with the carbon atom to which they are attached, and m is 0 to 1, or a pharmaceutically acceptable salt thereof.Type: GrantFiled: October 1, 1985Date of Patent: September 1, 1987Assignee: Kaken Pharmaceutical Co., Ltd.Inventors: Takanobu Naito, Masaaki Yokoyama, Kazuya Sasaki, Makoto Yamamoto, Kouji Amemiya
-
Patent number: 4690921Abstract: Novel cephalosporin compounds of the formula ##STR1## wherein the wavy line means syn-form and anti-form bonds, R.sup.1 represents a cyanomethyl group, a thiocarbamoylmethyl group or an aminothiazolylmethyl group, and A represents a unsubstituted or substituted pyridinio group; and salts thereof. These compounds have excellent antibacterial activities.Type: GrantFiled: September 28, 1984Date of Patent: September 1, 1987Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Tadao Shibanuma, Noriaki Nagano, Ryuichiro Hara, Kohji Nakano, Akio Koda, Atsuki Yamazaki, Yukiyasu Murakami
-
Patent number: 4684639Abstract: A compound having the partial structure (I) ##STR1## wherein R.sup.1 and R.sup.2 may be the same or different and each is hydrogen or a group --COR.sup.5 or --CO--OR.sup.5 wherein R.sup.5 represents an optionally substituted hydrocarbon group; R.sup.3 is halogen and R.sup.4 is hydrogen, methoxy, hydroxymethyl or formamido.These compounds are suitably bicyclic .beta.-lactam antibiotics.Type: GrantFiled: July 5, 1984Date of Patent: August 4, 1987Assignee: Beecham GroupInventors: George Burton, Desmond J. Best
-
Patent number: 4678781Abstract: A cephalosporin derivative of the formula I: ##STR1## in which X is S, O, CH.sub.2 or SO, R1 is (optionally-substituted)imidazol-2-yl or one of the C-7 acyl groups known in the cephalosporin art, R2 is hydrogen or methoxy, R3 is carboxy or a biodegradable ester thereof and --R4 is of the formula XII, XIII or XIV: ##STR2## in which R32-R40 inclusive are as defined in the specification; and the salts thereof. Pharmaceutical compositions, methods of manufacture and intermediates are also described.Type: GrantFiled: June 4, 1984Date of Patent: July 7, 1987Assignee: ICI PharmaInventor: Frederic Jung
-
Patent number: 4675398Abstract: The presence of a copper salt during the oximation of a .beta.-lactam containing compound having glyoxylamino substituents of the formula ##STR1## by reaction with an aminooxy compound having the formulaH.sub.2 N--O--R.sub.a,or a salt or ester thereof, results in a product wherein the ratio of syn isomer to anti isomer is increased.Type: GrantFiled: August 16, 1985Date of Patent: June 23, 1987Assignee: E. R. Squibb & Sons, Inc.Inventors: Thomas C. Sedergran, Carl F. Anderson
-
Patent number: 4670552Abstract: The invention provides crystalline ethyl (Z)-2-hydroxyimino-2-(2-triphenylmethylaminothiazol-4-yl)acetate hydrochloride N,N-dimethylformamide solvate which is of value as an intermediate in the preparation of .beta.-lactam antibiotics such as ceftazidime, azthreonam, cefmenoxime, cefotaxime, ceftriaxon, ceftizoxime and cefodizime.Type: GrantFiled: November 19, 1984Date of Patent: June 2, 1987Assignee: Glaxo Group LimitedInventors: William S. Strachan, Alastair C. Brodie
-
Patent number: 4667028Abstract: Process for the preparation of cephem compounds of the formula ##STR1##Type: GrantFiled: May 4, 1984Date of Patent: May 19, 1987Assignee: Hoechst AktiengesellschaftInventors: Wilfried Schwab, Walter Durckheimer, Reiner Kirrstetter, Rudolf Lattrell
-
Patent number: 4667029Abstract: The invention provides crystalline (Z)-2-(2-t-butoxycarbonyl-prop-2-oxyimino)-2-(2-triphenylmethylaminothiazo l-4-yl)acetic acid in association with dioxan and its crystalline ethyl ester in association with methanol. The compounds are of value as intermediates in the preparation of .beta.-lactam antibiotics such as ceftazidime or azthreonam.Type: GrantFiled: October 30, 1984Date of Patent: May 19, 1987Assignee: Glaxo Group LimitedInventor: Alastair C. Brodie
-
Patent number: 4665167Abstract: The invention provides crystalline (Z)-2-(2-t-butoxycarbonyl-prop-2-oxyimino)-2-(2-triphenylmethylaminothiazo l-4-yl)acetic acid in association with dioxan and its crystalline ethyl ester in association with methanol. The compounds are of value as intermediates in the preparation of .beta.-lactam antibiotics such as ceftazidime or azthreonam.Type: GrantFiled: October 30, 1984Date of Patent: May 12, 1987Assignee: Glaxo Group LimitedInventor: Brian E. Looker
-
Patent number: 4659813Abstract: Ceftazidime pentahydrate is obtained in purified crystalline form in a process comprising acidification of an aqueous solution of ceftazidime to about the optimum pH for nucleation of between about 4.0 and about 4.7 and maintenance at the optimum pH during crystallization. The crystalline product obtained exhibits enhanced stability toward polymer formation when stressed.Type: GrantFiled: November 22, 1985Date of Patent: April 21, 1987Assignee: Eli Lilly and CompanyInventors: Ronald C. Browning, Melvin G. Pleiss, Jr.
-
Patent number: 4654331Abstract: The (5-R-2-oxo-1,3-dioxolen-4-yl)methyl moiety: ##STR1## wherein R is loweralkyl of 1-6 carbon atoms, especially methyl or t-butyl; when utilized as an ester on a pharmaceutical having a carboxylic acid functionality, enhances oral absorption of the pharmaceutical. This effect is applicable to a broad range of pharmaceutically active substances, including antibiotics, and antihypertensives as well as other classes of therapeutic agents.Type: GrantFiled: August 23, 1984Date of Patent: March 31, 1987Assignee: Merck & Co., Inc.Inventor: Burton G. Christensen
-
Patent number: 4647556Abstract: The invention relates to cephem derivatives of the general formula I ##STR1## and their physiologically acceptable acid addition salts, to pharmaceutical formulations active against bacterial infections, to processes for preparing the compounds and formulations, and to the use of the compounds for combating bacterial infections.Type: GrantFiled: March 3, 1983Date of Patent: March 3, 1987Assignee: Hoechst AktiengesellschaftInventors: Rudolf Lattrell, Reiner Kirrstetter, Wilfried Schwab, Walter Durckheimer, Gerhard Seibert
-
Patent number: 4639448Abstract: The invention relates to cephem compounds of high antimicrobial activity of the formula: ##STR1## wherein R.sup.1 is amino or acylamino,R.sup.2 is lower alkyl, andY is CH or N.Type: GrantFiled: June 4, 1985Date of Patent: January 27, 1987Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takao Takaya, Hisashi Takasugi, Hideaki Yamanaka, Kenji Miyai, Yoshikazu Inoue
-
Patent number: 4631274Abstract: The invention relates to novel halovinyl cephem derivatives of high antimicrobial activity of the formula: ##STR1## wherein R.sup.1 is a group of the formula:R.sup.4 --A--CONH--in which R.sup.4 is cyano(lower)alkenylthio or a group of the formula: ##STR2## in which R.sup.6 is hydrogen, amino or a protected amino group, andA is carbonyl, lower alkylene, hydroxy(lower)alkylene or a group of the formula: ##STR3## in which R.sup.5 is hydrogen, carboxy(lower)alkyl or protected carboxy(lower)alkyl;R.sup.2 is carboxy or a protected carboxy group; andX is halogen, and pharmaceutically acceptable salts thereof.Type: GrantFiled: February 25, 1985Date of Patent: December 23, 1986Assignee: Fujisawa Pharmceutical Co., Ltd.Inventors: Takao Takaya, Kazuo Sakane, Hideaki Yamanaka, Kenzi Miyai
-
Patent number: 4626535Abstract: Novel antibacterially active cephalosporins of the formula ##STR1## in which R.sup.1 denotes hydrogen, optionally substituted alkyl, a substituted or unsubstituted phenyl ring, a polycyclic aromatic ring or an optionally substituted heterocyclic 5- or 6-member ring having 1-4 heteroatoms,R.sup.2 represents hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkenyl, halogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, hydroxymethyl, formyloxymethyl, C.sub.1 -C.sub.4 -alkylcarbonyloxymethyl, aminocarbonyloxymethyl, pyridiniummethyl, 4-carbamoylpyridiniummethyl, 4-sulphonylethylpyridiniummethyl, 4-carboxylmethylpyridiniummethyl or heterocyclylthiomethyl, heterocyclyl representing a radical of the formula ##STR2## wherein R.sup.8 denotes hydrogen, methyl, 2-dimethylaminoethyl, carboxymethyl, sulphomethyl, carboxyethyl or sulphoethyl andR.sup.9 denotes hydrogen or methyl,or pharmaceutically tolerated salts or esters thereof.Type: GrantFiled: December 30, 1983Date of Patent: December 2, 1986Assignee: Bayer AktiengesellschaftInventors: Rolf Angerbauer, Michael Boberg, Gunther Kinast, Karl G. Metzger, Wilfried Schrock, Hans-Joachim Zeiler
-
Patent number: 4624948Abstract: Anhydrous crystalline (6R,7R)-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oximino)acetamid o]-3-(1-pyridiniummethyl)-3-cephem-4-carboxylate and a process for its preparation, a pharmaceutical formulation which is active against bacterial infections and contains this compound and a process for the preparation of the formulation and the use of this compound for controlling bacterial infections.Type: GrantFiled: April 16, 1984Date of Patent: November 25, 1986Assignee: Hoechst AktiengesellschaftInventor: Walter Durckheimer
-
Patent number: 4622318Abstract: The invention relates to new cephem compounds of high antimicrobial activity of the formula: ##STR1## wherein R.sup.1 is amino or a group of the formula: ##STR2## in which R.sup.5 is amino or a protected amino group,R.sup.9 is lower alkyl, lower alkenyl, lower alkynyl, cyclo(lower)alkenyl, carboxy(lower)alkyl, protected carboxy(lower)alkyl or saturated 4 to 8-membered heteromonocyclic group containing one sulfur atom, andZ is N or CH,R.sup.2 is cyano, phenyl, pyridyl, lower alkylpyridyl, or tri(lower)alkylsilyl,R.sup.3 is carboxy or protected carboxy, andA is --CH.dbd.CH-- or --C.tbd.C--,and pharmaceutically acceptable salt thereof.Type: GrantFiled: October 19, 1984Date of Patent: November 11, 1986Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takao Takaya, Zenzaburo Tozuka, Nobuyoshi Yasuda, Kohji Kawabata
-
Patent number: 4622394Abstract: In accordance with this invention, it has been found that the oxygen analog of 7-amino-cephalosporanic acid and biologically active derivatives thereof can be formed from esters of 7-amino-cephalosporanic acid. Esters of 7-oxocephalosporanic acid can be formed by diazotization of an ester or 7-amino-cephalosporanic acid and contact of the diazo compound so formed with a hypohalous acid and a base in a water miscible organic solvent. Oxygen analogs of 7-aminocephalosporins isolated as esters are then formed by reducing the aforesaid ester to the corresponding 7.beta.-hydroxy-cephalosporanate and then forming the desired analog by introduction of a side chain via hydroxyl group modification. Oxygen analogs of 7-amino-cephalosporins are then formed by regeneration of the acid via protective group removal.Type: GrantFiled: December 2, 1977Date of Patent: November 11, 1986Assignee: Massachusetts Institute of TechnologyInventors: John C. Sheehan, Young S. Lo
-
Patent number: 4621081Abstract: Cephalosporin antibiotics of general formula: ##STR1## (wherein R.sup.a and R.sup.b, which may be the same or different, each represent a C.sub.1-4 alkyl group or R.sup.a and R.sup.b together with the carbon atom to which they are attached form a C.sub.3-7 cycloalkylidene group, and Y.sup..sym. represents a C-linked 5- or 6-membered heterocyclic ring containing at least one C.sub.1-4 alkyl-substituted quaternary nitrogen atom, which ring may also contain one or more sulphur atoms) exhibit broad spectrum antibiotic activity, the activity being unusually high against gram-negative organisms such as strains of Pseudomonas organisms.A particular antibiotic compound of formula (I) possessing excellent antibacterial activity against strains of Pseudomonas organisms, as well as other valuable therapeutic properties, is (6R,7R)-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(1-carboxycyclobut-1-oxyimino)ace tamido]-3-[(1-methylpyridinium-4-yl)-thiomethyl]ceph-3-em-4-carboxylate.Type: GrantFiled: September 27, 1982Date of Patent: November 4, 1986Assignee: Glaxo Group LimitedInventors: Cynthia H. O'Callaghan, Barry E. Ayres, David G. H. Livermore, Christopher E. Newall, Niall G. Weir
-
Patent number: 4616081Abstract: Novel cephalosporin compounds having antibacterial activity, which are represented by the following compounds of the general formula (I), ##STR1## wherein R.sub.1 represents an amino group or a protected amino group;.circle.A represents a 5- or 6-membered heterocyclic ring containing therein 1 to 4 nitrogen, oxygen or sulfur atoms;R.sub.2 represents a normal alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 6 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms; a cycloalkenyl group having 3 to 6 carbon atoms; an aromatic organic residue; a 3- to 6-membered heterocyclic ring containing 1 to 4 nitrogen, sulfur or oxygen atoms or, ##STR2## wherein Ra and Rb each, which may be the same or different, represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;R.sub.Type: GrantFiled: July 6, 1983Date of Patent: October 7, 1986Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Joji Nishikido, Eiji Kodama, Chisei Shibuya
-
Patent number: 4616080Abstract: Ceftazidime pentahydrate in crystalline form is provided in a one-step process comprising acidic removal of protecting groups from an amino-protected and carboxy-protected ceftazidime, separation of aqueous phase after addition of a water-immiscible organic solvent, and precipitation of pentahydrate by adjusting pH of aqueous phase from about 3.5 to about 4.5.Type: GrantFiled: July 2, 1984Date of Patent: October 7, 1986Assignee: Eli Lilly and CompanyInventors: Ta-Sen Chou, Robert E. Lakin
-
Patent number: 4614819Abstract: This invention relates to a novel process for producing a useful cephalosporin which comprises reacting a thiolo ester compound with a 7-aminocephalosporin in the presence of boron trifluoride or a complex compound thereof. This process enables the cephalosporin to be produced with a high purity in a high yield.Type: GrantFiled: September 19, 1984Date of Patent: September 30, 1986Assignee: Toyama Chemical Co., Ltd.Inventors: Takashi Nagai, Hirokazu Ochiai, Takihiro Inaba, Isao Myokan, Hiroshi Sadaki, Isamu Saikawa
-
Patent number: 4609654Abstract: The present invention relates to new cephalosporins of general formula ##STR1## in which R.sub.1 =R.sub.2 =CH.sub.3 or R.sub.1 and R.sub.2 together form a 1,3-propylene group, A is H, a cation, an ester or a hemiacetal, and R.sub.3 is a heterocycle comprising five or six atoms including at least one atom in the ring of nitrogen. It also relates to a process for preparing these cephalosporins and to the drugs containing them.Type: GrantFiled: November 23, 1982Date of Patent: September 2, 1986Assignee: SanofiInventors: Bernard Labeeuw, Ali Salhi