US 4,379,152 AGranted

Cephalosporins

AssigneeToyama Chemical Co., Ltd.

InventorsIsamu Saikawa, Shuntaro Takano, Chosaku Yoshida, Okuta Takashima, Kaishu Momonoi, Seietsu Kuroda, Miwako Komatsu, Takashi Yasuda, Yutaka Kodama

Life of this patent

Estimating the term…

Abstract

Novel penicillins and cephalosporins and non-toxic salts thereof, which contain a mono- or di-oxo- or thioxo-piperazino(thio)carbonylamino group in molecule. These compounds are valuable antibacterial compounds for use in mammals including man. This disclosure relates to such compounds and a process for the preparation thereof.

Claims27

Dependent claims

An antibacterial compound of the formula (I), ##STR602## wherein R is a group represented by the formula ##STR603## each of said moieties A, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 is a conventional penicillin or cephalosporin substituent selected from the groups or atoms which each of said moieties represents as set forth subsequently, wherein R.sup.5 represents alkyl, cycloalkyl, cycloalkenyl, cycloalkadienyl, aryl, aralkyl, aryloxy, alkylthioalkyl, furyl, thienyl, oxazoly, thiazolyl, isoxazolyl, isothiazolyl, imidazolyl, pyrazolyl, pyridyl, pyrazyl, pyrimidyl, pyridazyl, quinolyl, isoquinolyl, quinazolyl, indolyl, indazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl or 1,2,4-thiadiazolyl, any of which may be substituted by halogen, hydroxy, nitro, alkyl, alkoxy, alkylthio, acyl or alkylsulfonylamino;

R.sup.6 represents a hydrogen atom;
and R.sup.5 and R.sup.6 together with a common carbon atom may form a cycloalkyl, cycloalkenyl or cycloalkadienyl ring;
R.sup.1 represents a hydrogen atom, a blocking group of a conventional penicillin or cephalosporin or a pharmaceutically acceptable salt-forming cation of a conventional penicillin or cephalosporin;
n represents 1 or 2;
each of the n X's, which may be identical or different from one another, represents individually an oxygen or sulfur atom, and the n X's are attached in any combination to the 2-, 3-, or 5-positions of the piperazine ring;
m represents 4-n;
each pair of R.sup.2 and R.sup.3 are linked to the same carbon atom, and each R.sup.2 and R.sup.3 of m pairs of R.sup.2 and R.sup.3, which may be the same or different, represent individually hydrogen, halogen, carboxyl, alkyl, cycloalkyl, aryl, acyl, aralkyl, alkoxycarbonylalkyl, acyloxyalkyl, alkoxy, alkoxycarbonyl, cycloalkyloxycarbonyl, aralkoxycarbonyl, aryloxycarbonyl, amino, N-alkylamino, N,N-dialkylamino, N-arylaminocyclic amino or carbamoyl;
any of which may be substituted by halogen, alkyl, alkoxy, alkylthio, acyl or nitro;
and any pair of R.sup.2 and R.sup.3 together with a common carbon atom may form a cycloalkyl ring
A represents hydrogen, hydroxy, nitro, cyano, alkyl, alkenyl, alkynyl, alkadienyl, cycloalkyl, cycloalkenyl, cycloalkadienyl, aryl, acyl, aralkyl, acyloxyalkyl, alkoxy, cycloalkyloxy, alkoxycarbonyl, aryloxy, cycloalkyloxycarbonyl, aryloxycarbonyl, aralkoxycarbonyl, alkylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, carbamoyl, N-alkylaminocarbonyl, N-arylaminocarbonyl, N,N-dialkylaminocarbonyl, cyclic aminocarbonyl, thiocarbamoyl, N-alkylaminothiocarbonyl, N-arylaminothiocarbonyl, N,N-dialkylaminothiocarbonyl, cyclic aminothiocarbonyl, acylcarbamoyl, acylthiocarbamoyl, alkylsulfonylcarbamoyl, arylsulfonylcarbamoyl, alkylsulfonylthiocarbamoyl, arylsulfonylthiocarbamoyl, sulfamoyl, alkoxycarbonylthioalkyl, alkoxythiocarbonylthioalkyl, amino, thiazolyl, pyridyl, pyridazyl, pyrazyl, thiadiazolyl, triazolyl, tetrazolyl or quinolyl, any of which may be substituted by halogen, hydroxyl, alkyl, alkoxy, alkylthio, nitro, cyano, amino, carboxyl, or acyl;
Y represents an oxygen or sulfur atom;
and
R.sup.4 represents hydrogen, an acyloxy group or a carbamoyloxy group.

10 more elements

A compound of the formula (I), ##STR616## wherein R is a group represented by the formula ##STR617## each of said moieties A, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 is a conventional penicillin or cephalosporin substituent selected from the groups or atoms which each of said moieties represents as set forth subsequently,

wherein R.sup.5 represents methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cyclopentadienyl, cyclohexadienyl, phenyl, naphthyl, benzyl, phenethyl, phenoxy, naphthoxy, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, furyl, thienyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, imidazolyl, pyrazolyl, pyridyl, pyrazyl, pyrimidyl, pyridazyl, quinolyl, isoquinolyl, quinazolyl, indolyl, indazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, or 1,2,4-thiadiazolyl;
each group represented by said R.sup.5 may be substituted by halogen, hydroxy or nitro;
R.sup.6 represents a hydrogen atom;
and R.sup.5 and R.sup.6 together with a common carbon atom may form a cyclohexyl, cycloheptyl or cyclopentenyl, cyclohexenyl, cyclopentadienyl or cyclohexadienyl ring,
R.sup.1 represents a hydrogen atom, a blocking group of a conventional penicillin or cephalosporin or a pharmaceutically acceptable salt-forming cation of a conventional penicillin or cephalosporin;
n represents 1 or 2;
each of the n X's, which may be identical or different from one another, represents individually an oxygen or sulfur atom, and the n X's are attached in any combination to the 2-, 3-, or 5-positions of the piperazine ring;
m represents 4-n;
each pair of R.sup.2 and R.sup.3 are linked to the same carbon atom, and each R.sup.2 and R.sup.3 of m pairs of R.sup.2 and R.sup.3, which may be the same or different, represent individually, a hydrogen atom, a halogen atom, a carboxyl group, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopentyl, cyclohexyl, cycloheptyl, phenyl, naphthyl, acetyl, propionyl, butyryl, benzoyl, benzyl, phenethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, acetyloxymethyl, propionyloxymethyl, pivaloylmethyl, benzoyloxymethyl, methoxy, ethoxy, propoxy, butoxy, methoxyycarbonyl, ethoxycarbonyl, propoxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, cycloheptyloxycarbonyl, benzyloxycarbonyl, phenethoxycarbonyl, phenoxycarbonyl, naphthoxycarbonyl, amino, N-methylamino, N-ethylamino, N-propylamino, N-butylamino, N,N-dimethylamino, N,N-diethylamino, N-N-dibutylamino, N-acetylamino, N-propionylamino, N-butyrylamino, N-benzoylamino, pyrrolidino, piperidino, morpholino, carbamoyl, N-methylaminocarbonyl, N-ethylaminocarbonyl, N-N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl, and any pair of R.sup.2 and R.sup.3 together with a common carbon atom may form a cyclopentyl, cyclohexyl or cycloheptyl group, and each of the groups mentioned above for said R.sup.2 and R.sup.3 may be substituted by halogen or nitro;
A represents hydrogen, hydroxy group, nitro, cyano, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, heptyl, octyl, dodecyl, vinyl, propenyl, butenyl, propargyl, 1,3-butadienyl, 1,3-pentadienyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cyclopentadienyl, cyclohexadienyl, phenyl, naphthyl, formyl, acetyl, propionyl, isovaleryl, caproyl, enanthoyl, capryloyl, palmitoyl, stearoyl, acryloyl, cyclohexanecarbonyl, benzoyl, phenylglycyl, furoyl, thenoyl, benzyl, phenethyl, acetyloxyethyl, pivaloyloxymethyl, benzoyloxymethyl, methoxy, ethoxy, propoxy, butoxy, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, phenoxy, naphthoxy, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, cycloheptyloxycarbonyl, phenoxycarbonyl, (1- or 2-)naphthoxycarbonyl, benzyloxycarbonyl, phenethoxycarbonyl, methanesulfonyl, ethanesulfonyl, propanesulfonyl, butanesulfonyl, cyclopentanesulfonyl, cyclohexanesulfonyl, benzenesulfonyl, (1- or 2-(napthalenesulfonyl, carbamoyl, N-methylaminocarbonyl, N-ethylaminocarbonyl, N-propylaminocarbonyl, N-butylaminocarbonyl, N-phenylaminocarbonyl, N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl, pyrrolidinocarbonyl, piperidinocarbonyl, morpholinocarbonyl, thiocarbamoyl, N-methylaminothiocarbonyl,.N-ethylaminothiocarbonyl, N-propylaminothiocarbonyl, N-phenylaminothiocarbonyl, N-N-dimethylaminothiocarbonyl, N-N-diethylaminothiocarbonyl, pyrrolidinothiocarbonyl, piperidinothiocarbonyl, morpholinothiocarbonyl, N-acetylcarbamoyl, N-propionylcarbamoyl, N-butyrylcarbamoyl, N-benzoylcarbamoyl, N-furoylcarbamoyl, N-thenoylcarbamoyl, N-acetylthiocarbamoyl, N-propionylthiocarbamoyl, N-butyrylthiocarbamoyl, N-benzoylthiocarbamoyl, N-naphthoylthiocarbamoyl, N-furoylthiocarbamoyl, N-thenoylthiocarbamoyl, methanesulfonylaminocarbony, ethanesulfonylaminocarbonyl, butanesulfonylaminocarbonyl, benzenesulfonylaminocarbonyl, (1- or 2-)naphthaleneslfonylaminocarbonyl, methanesulfonylaminothiocarbonyl, ethanesulfonylaminothiocarbonyl, butanesulfonylaminothiocarbonyl, benenesulfonylaminothiocarbonyl, naphthalenesulfonylaminothiocarbonyl, sulfamoyl, N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-butylsulfamoyl, N,N-dimethylsulfamoyl, N,N-diethylsulfamoyl, N,N-dipropylsulfamoyl, N,N-dibutylsulfamoyl, N-phenylsulfamoyl, N-benzylsulfamoyl, N-cyclopentylsulfamoyl, N-cyclohexylsulfamoyl, methoxycarbonylthiomethyl, ethoxycarbonylthiomethyl, propoxycarbonylthiomethyl, butoxycarbonylthiomethyl, methoxycarbonylthioethyl, methoxythiocarbonylthiomethyl, ethoxythiocarbonylthiomethyl, propoxythiocarbonylthiomethyl, butoxythiocarbonylthiomethyl, methoxythiocarbonylthioethyl, amino, N-methylamino, N-ethylamino, N-propylamino, N-butylamino, N,N-dimethylamino, N,N-diethylamino, N,N-dibutylamino, N-acetylamino, N-propionylamino, N-butyrylamino, N-benzoylamino, pyrrolidino, piperidino, morpholino, thiazolyl, pyridyl, pyridazyl, pyrazyl, thiadiazolyl, triazolyl, tetrazolyl, quinolyl, any of which may be substituted by halogen, hydroxyl, nitro groups, cyano or carboxyl groups;
Y represents an oxygen or sulfur atom;
R.sup.4 represents acetyloxy, propionyloxy, butyryloxy, benzoyloxy, naphthoxyloxy, cyclopentanecarbonyloxy, cyclohexanecarbonyloxy, furoyloxy, thenoyloxy, carbamoyloxy, N-methylaminocarbonyloxy, N,N-dimethylaminocarbonyloxy, N-acetylaminocarbonyloxy, phenylaminocarbonyloxy, benzylaminocarbonyloxy or cyclohexylaminocarbonyloxy.

9 more elements

A compound of the formula (I), ##STR618## wherein R is a group represented by the formula ##STR619## each of said moieties A, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 is a conventional penicillin or cephalosporin substituent selected from the groups or atoms which each of said moieties represents as set forth subsequently,

wherein R.sup.5 represents methyl, ethyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cyclopentadienyl, cyclohexadienyl, phenyl, naphthyl, benzyl, phenoxy, naphthoxy, furyl, thienyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, imidazolyl, pyrazolyl, pyridyl, pyrazyl, pyrimidyl, pyridazyl, quinolyl, isoquinolyl, quinazolyl, indolyl, indazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl or 1,2,4-thiadiazolyl;
each group represented by said R.sup.5 may be substituted by halogen, hydroxy or nitro;
R.sup.6 represents a hydrogen atom;
and R.sup.5 and R.sup.6 together with a common carbon atom may form a cyclohexyl, cycloheptyl or cyclopentyl, cyclohexenyl, cyclopentadienyl or cyclohexadienyl ring;
R.sup.1 represents a hydrogen atom, a blocking group of a conventional penicillin or cephalosporin or a pharmaceutically acceptable salt-forming cation of a conventional penicillin or cephalosporin;
n represents 1 or 2;
each of the nX's, which may be identical or different from one another, represents individually an oxygen or sulfur atom, and the nX's are attached in any combination to the 2-, 3- or 5-position of the piperazine ring;
m represents 4-n;
each pair of R.sup.2 and R.sup.3 are linked to the same carbon atom, and each R.sup.2 and R.sup.3 of m pairs of R.sup.2 and R.sup.3, which may be the same or different, represent individually a hydrogen atom, a halogen atom, a carboxyl group, methyl, ethyl, propyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, acetyl, benzoyl, benzyl, acetyloxymethyl, pivaloyloxymethyl, methoxy, ethoxy, propoxy, methoxycarbonyl, ethoxycarbonyl, cyclohexylcarbonyl, benzyloxycarbonyl, phenoxycarbonyl, amino, N-methylamino, N-ethylamino, N,N-dimethylamino, N-acetylamino, carbamoyl, N-methylaminocarbonyl, N,N-dimethylaminocarbonyl, and any pair of R.sup.2 and R.sup.3 together with a common carbon atom may form a cyclopentyl or cyclohexyl group, and each of the groups mentioned above for said R.sup.2 and R.sup.3 may be substituted by halogen;
A represents hydrogen, hydroxy group, nitro, cyano, methyl, ethyl, propyl, vinyl, propenyl, propargyl, 1,3-pentadienyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopentadienyl, cyclohexadienyl, phenyl, naphthyl, formyl, acetyl, propionyl, benzoyl, furoyl, thenoyl, benzyl, pivaloyloxymethyl, methoxy, ethoxy, cyclopentyloxy, cyclohexyloxy, phenoxy, naphthoxy, methoxycarbonyl, ethoxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, phenoxycarbonyl, benzyloxycarbonyl, methanesulfonyl, ethanesulfonyl, cyclohexanesulfonyl, benzenesulfonyl, carbamoyl, N-methylaminocarbonyl, N-phenylaminocarbonyl, N,N-dimethylaminocarbonyl, pyrrolidinocarbonyl, piperidinocarbonyl, thiocarbamoyl, N-methylaminothiocarbonyl, N-phenylaminothiocarbonyl, N,N-dimethylaminothiocarbonyl, pyrrolidinothiocarbonyl, piperidinothiocarbonyl, N-acetylcarbamoyl, N-acetylthiocarbamoyl, methanesulfonylaminocarbonyl, methanesulfonylaminothiocarbonyl, sulfamoyl, N-methylsulfamoyl, N-ethylsulfamoyl, N,N-dimethylsulfamoyl, N-phenylsulfamoyl, N-cyclohexylsulfamoyl, amino, N-methylamino, N-ethylamino, N,N-dimethylamino, N-acetylamino, thiazolyl, pyridyl, pyridazyl, pyrazyl, any of which may be substituted by halogen, nitro groups, cyano or carboxyl groups;
Y represents an oxygen or sulfur atom;
R.sup.4 represents hydrogen, acetyloxy, propionyloxy, butyryloxy, benzoyloxy, naphthoyloxy, cyclopentanecarbonyloxy, thenoyloxy, carbamoyloxy, N-methylaminocarbonyloxy, N,N-dimethylaminocarbonyloxy, N-acetylaminocarbonyloxy, phenylaminocarbonyloxy, benzylaminocarbonyloxy or cyclohexylaminocarbonyloxy.

9 more elements

A compound selected from the group consisting of 7-[D(-)-.alpha.-(4-methyl-2,3-dioxo-1-piperazinocarbonyl-amino)phenylaceta mido]-3-methyl-.DELTA.3-cephem-4-carboxylic acid,

7-[D(-)-.alpha.-(4-ethyl-2,3-dioxo-1-piperazinocarbonylamino)phenylacetamid o]-3-methyl-.DELTA..sup.3 -cephem-4-carboxylic acid,
7-[D(-)-.alpha.-(4-n-propyl-2,3-dioxo-1-piperazinocarbonylamino)phenylaceta mido]-3-methyl-.DELTA..sup.3 -cephem-4-carboxylic acid,
7-[D(-)-.alpha.-(4-n-butyl-2,3-dioxo-1-piperazinocarbonylamino)phenylacetam ido]-3-methyl-.DELTA..sup.3 -cephem-4-carboxylic acid,
7-[D(-)-.alpha.-(4-n-pentyl-2,3-dioxo-1-piperazinocarbonylamino)phenylaceta mido]-3-methyl-.DELTA..sup.3 -cephem-4-carboxylic acid,
7-[D(-)-.alpha.-(4-n-hexyl-2,3-dioxo-1-piperazinocarbonylamino)phenylacetam ido]-3-methyl-.DELTA..sup.3 -cephem-4-carboxylic acid,
7-[D(-)-.alpha.-(4-n-heptyl-2,3-dioxo-1-piperazinocarbonylamino)phenylaceta mido]-3-methyl-.DELTA..sup.3 -cephem-4-carboxylic acid,
7-[D(-)-.alpha.-(4-n-octyl-2,3-dioxo-1-piperazinocarbonylamino)phenylacetam ido]-3-methyl-.DELTA..sup.3 -cephem-4-carboxylic acid,
7-[D(-)-.alpha.-(4-methyl-2,3-dioxo-1-piperazinocarbonylamino)phenylacetami do]-3-acetoxymethyl-.DELTA..sup.3 -cephem-4-carboxylic acid,
7-[D(-)-.alpha.-(4-ethyl-2,3-dioxo-1-piperazinocarbonylamino)phenylacetamid o]-3-acetoxymethyl-.DELTA..sup.3 -cephem-4-carboxylic acid,
7-[D(-)-.alpha.-(4-n-propyl-2,3-dioxo-1-piperazinocarbonylamino)phenylaceta mido]-3-acetoxymethyl-.DELTA..sup.3 -cephem-4-carboxylic acid,
7-[D(-)-.alpha.-(4-iso-propyl-2,3-dioxo-1-piperazinocarbonylamino)phenylace tamido]-3-acetoxymethyl-.DELTA..sup.3 -cephem-4-carboxylic acid,
7-[D(-)-.alpha.-(4-methyl-2,3-dioxo-1-piperazinothiocarbonylamino)phenylace tamido]-3-acetoxymethyl-.DELTA..sup.3 -cephem-4-carboxylic acid,
7-[D(-)-.alpha.-(4-ethyl-2,3-dioxo-1-piperazinothiocarbonylamino)phenylacet amido]-3-acetoxymethyl-.DELTA..sup.3 -cephem-4-carboxylic acid, and
7-[D(-)-.alpha.-(4-methyl-2,3-dioxo-1-piperazinocarbonylamino)propionamido] -3-acetoxymethyl-.DELTA..sup.3 -cephem-4-carboxylic acid.

11 more elements

Dependencies are inferred from the claim text.

Facts

Application: 06/039,904Filed 17 May 1979 · division
Priority: 30 Jan 1976
Granted: 5 Apr 1983
Term ends: Not estimatedThe source records don’t support an estimate.

Classification3 codes

C07D 241/08
Having one or two double bonds between ring members or between ring members and non-ring members: with oxygen atoms directly attached to ring…
C07D 499/00
Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a
C07D
Heterocyclic compounds

Family

Serial654,060Parent of this division · filed 30 Jan 1976
Serial915,873Parent of this division · filed 15 Jun 1978
US 4,219,554 AParent of this division
US 4,112,090 AParent of this division
US 4,379,152 AThis patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

R.sup.6 represents a hydrogen atom;
and R.sup.5 and R.sup.6 together with a common carbon atom may form a cycloalkyl, cycloalkenyl or cycloalkadienyl ring;
R.sup.1 represents a hydrogen atom, a blocking group of a conventional penicillin or cephalosporin or a pharmaceutically acceptable salt-forming cation of a conventional penicillin or cephalosporin;
n represents 1 or 2;
each of the n X's, which may be identical or different from one another, represents individually an oxygen or sulfur atom, and the n X's are attached in any combination to the 2-, 3-, or 5-positions of the piperazine ring;
m represents 4-n;
each pair of R.sup.2 and R.sup.3 are linked to the same carbon atom, and each R.sup.2 and R.sup.3 of m pairs of R.sup.2 and R.sup.3, which may be the same or different, represent individually hydrogen, halogen, carboxyl, alkyl, cycloalkyl, aryl, acyl, aralkyl, alkoxycarbonylalkyl, acyloxyalkyl, alkoxy, alkoxycarbonyl, cycloalkyloxycarbonyl, aralkoxycarbonyl, aryloxycarbonyl, amino, N-alkylamino, N,N-dialkylamino, N-arylaminocyclic amino or carbamoyl;
any of which may be substituted by halogen, alkyl, alkoxy, alkylthio, acyl or nitro;
and any pair of R.sup.2 and R.sup.3 together with a common carbon atom may form a cycloalkyl ring
A represents hydrogen, hydroxy, nitro, cyano, alkyl, alkenyl, alkynyl, alkadienyl, cycloalkyl, cycloalkenyl, cycloalkadienyl, aryl, acyl, aralkyl, acyloxyalkyl, alkoxy, cycloalkyloxy, alkoxycarbonyl, aryloxy, cycloalkyloxycarbonyl, aryloxycarbonyl, aralkoxycarbonyl, alkylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, carbamoyl, N-alkylaminocarbonyl, N-arylaminocarbonyl, N,N-dialkylaminocarbonyl, cyclic aminocarbonyl, thiocarbamoyl, N-alkylaminothiocarbonyl, N-arylaminothiocarbonyl, N,N-dialkylaminothiocarbonyl, cyclic aminothiocarbonyl, acylcarbamoyl, acylthiocarbamoyl, alkylsulfonylcarbamoyl, arylsulfonylcarbamoyl, alkylsulfonylthiocarbamoyl, arylsulfonylthiocarbamoyl, sulfamoyl, alkoxycarbonylthioalkyl, alkoxythiocarbonylthioalkyl, amino, thiazolyl, pyridyl, pyridazyl, pyrazyl, thiadiazolyl, triazolyl, tetrazolyl or quinolyl, any of which may be substituted by halogen, hydroxyl, alkyl, alkoxy, alkylthio, nitro, cyano, amino, carboxyl, or acyl;
Y represents an oxygen or sulfur atom;
and
R.sup.4 represents hydrogen, an acyloxy group or a carbamoyloxy group.

10 more elements

Facts

Application

06/039,904Filed 17 May 1979 · division

Priority

30 Jan 1976

Granted

5 Apr 1983

Term ends

Not estimatedThe source records don’t support an estimate.

Classification3 codes

C07D 241/08
Having one or two double bonds between ring members or between ring members and non-ring members: with oxygen atoms directly attached to ring…
C07D 499/00
Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a
C07D
Heterocyclic compounds