Antibacterial compounds

Claim 2

A compound of the formula; wherein R o stands for hydrogen atom, nitrogen- containing heterocyclic group, acyl group or esterified carboxyl group, Z stands for S, S→O, 0 or CH 2 , R 4 stands for hydrogen atom, methoxy group or formamido group, R 13 stands for hydrogen atom, methyl group, hydroxyl group or halogen atom and A stands for an optionally substituted imidazol-1-yl group forming a condensed ring at the 2,3- or 3,4-position or a physiologically or pharmaceutically acceptable salt or ester thereof.

Claim 3

A compound according to claim 1 wherein the nitrogen-containing heterocyclic group is a 5 to 8 membered nitrogen-containing heterocylic group which may be substituted.

Claim 4

A compound according to claim 1 wherein the acyl group is alkanoyl group, alkenoyl group, cycloalkyl-carbonyl group, cycloalkenyl-carbonyl group, aryl-carbonyl group or heterocycle-carbonyl group which may be substituted.

Claim 5

A compound according to claim 3 wherein the alkanoyl group is a group of the formula which R 22 denotes C 3-10 cycloalkyl * group, C 5-6 cycloalkenyl* group, C 6-10 aryl* group, C 1-6 alkox y group, C6-10 aryl * oxy group, C 1-6 alkyl * thio group, amino C 1-6 alkylthio group, C 6-10 ary l * thio group, C 7-19 aralkyl * thio group, cyano group, acyl + group, carbamoyl group or heterocyclic * group and R 21 denotes OR 23 group wherein R 23 is hydrogen atom or optionally substituted hydrocarbon residue, wherein acyl+ group denotes C 1-6 alkanoyl group, C 6-10 aryl*carbonyl group, C 7-19 aralkyl * carbonyl group, heterocycle * carbonyl group or heterocycle * acetyl group and the group bearing asterisk * denotes optionally substituted group.

Claim 6

A compound according to claim 4 wherein R 22 denotes a 5 to 8 membered heterocyclic group which may be substituted with C 1-6 alkyl group, hvdroxyl group, amino group or halogen atom and the configuration of R 21 is s y n.

Claim 7

A compound according to claim 5 wherein the heterocyclic group is a group of the formula in which R 2 denotes hydrogen atom or halogen atom.

Claim 8

A compound according to claim 4 wherein the optionally substituted hydrocarbon residue is C 1-3 alkyl group which may be substituted with halogen atom, hydroxyl group, C 1-6 alkoxy group, carboxyl group, C 1-6 alkoxy-carbonyl group or cyano group and the configuration of R2 1 is syn.

Claim 9

A compound according to claim 1 wherein the esterified carboxyl group is C 1-10 alkoxy-carbonyl group, C 6-1 0 ar y lox y -carbonyl group or C 7-19 aralkyloxy-carbonyl group which may be substituted.

Claim 10

A Compound according to claim 1 wherein Z is S.

Claim 11

A compound according to claim 1 wherein R 4 is hydrogen atom.

Claim 12

A compound according to claim 1 wherein R 13 is hydrogen atom.

Claim 13

A compound according to claim 1 wherein A is an optionally substituted imidazol-1-yl group having at the 2,3- or 3,4-position a 5 to 6 membered aromatic heterocyclic ring condensed herewith.

Claim 14

A compound according to claim 1 wherein A is imidazo[1,2-a]pyridinium-1-yl group or imidazo[1,5-a]pyridinium-2-yl group which may be substituted.

Claim 15

A compound according to claim 1 wherein R° is a group of the formula; in which R 2 denotes hydrogen atom or halogen atom, R 23 denotes C 1-3 alkyl group optionally substituted with halogen atom, hydroxyl group,C 1-6 alkoxy group, carboxyl group, C 1-6 alkoxy-carbonyl group or cyano group, Z is S, R- is hydrogen atom, R 13 is hydrogen atom and A is an optionally substituted imidazo[1,2-a]pyridinium-1-yl group or imidazo[1,5-a]pyridinium-2-yl group.

Claim 16

A compound according to claim lselected from 7β-[2-(2-amino-thiazol-4-yl)-2(Z)-methoxyiminoacetamido]-3-[(imidazo[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate; 7β-[2-(2-amino-thiazol-4-yl)-2(Z)-ethoxyiminoacetamido]-3-[(imidazo[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate] 7β-[2-(2-amino-thiazol-4-yl)-2(Z)-(1-carboxy-1-methylethoxyimino)acetamido]-3-[(imidazo[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate; 7β-[2-(2-amino-thiazol-4-yl)-2(Z)-(2-fluoroethoxyimino)acetamido]-3-[(imidazo[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate; 7β-[-2-(-2-amino-thiazol-4-yl)-2(Z)-(2-chloroethoxyimino)acetamido]-3-[ (imidazo[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate; - , 7β-[2-(2-amino-thiazol-4-yl)-2(Z)-(2-hydroxyethoxyimino)acetamido]-3-[(imidazo[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate: 7 β- [2- ( 2-amino-thiazol-4-yl)-2(Z)-methoxyiminoacetamido]-3-[(6-chloro- imidazo [1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate; 7 β- [2- ( 2-amino-thiazol-4-yl)-2(Z)-ethoxyiminoacetamido]-3-[(6-chloro- imidazo[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate. 7 β- [2- (2-amino-thiazol-4-yl)-2(Z)-methoxyimincacetamido]-3-[(6-cyanoimidazo[1,2-a]pyridinium-1-yl)methyl]-3-cephein-4-carboxylate ; 7β-[2-(2-amino-thiazol-4-yl)-2(Z)-ethoxyiminoacetamido]-3-[(6-cyanoimidazo[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate ; 7β-[2-(2-amino-thiazol-4-yl)-2(Z)-(1-carboxy-1-methylethoxyimino)acetamido]-3-[(6-cyanoimidazo[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate; - . 7β-[2-(2-amino-thiazol-4-yl) -2 (z)-(2-flucroethoxyimino)acetamido]-3-[(6-cyanoimidazo[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylatel 7β-[2-(2-amino-thiazol-4-yl)-2(Z)-(2-chloroethoxyimino)acetamido]-3-[(6-cyanoimidazo[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate; 7β-[2-(2-amino thiazol-4-yl)-2-(Z)-methoxyiminoacetamido]-3-[(3-cyanoimidazo[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate ; - 7β-[2- (2-amino-thiazol-4-yl)-2(2)-methoxyiminoacetamido]-3-[(imidazo[1,5-a]pyridinium-2-yl)methyl]-3-cephem-4-carboxylate ; 7β-[2-(2-amino-5-chlorothiazol-4-yl)-2(Z)-methoxyiminoacetamido]-3-[(imidazo[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate ; . 7β-[2-(2-amino-5-chlorothiazol-4-yl)-2(Z)-carboxymethoxyiminoacetamido]-3-[(imidazo[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate ; 7β-[2-(2-amino-5-chlorothiazol-4-yl)-2(Z)-methoxyiminoacetamido]-3-[(imidazo[1,5-a]pyridiniun-2-yl)methyl]-3-cephem-4-carboxylate ; 7β-[2-(2-amino-thiazol-4-yl-3-oxido)-2(Z)-ethoxyimininoacetamido]-3-[(imidazo[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate ; _ 7β-[2-(2-amino-thiazol-4-yl)-2-formamidoacetamido]-3-[(imidazo[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate ; 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-methoxyiminoacetamido]-3-[(imidazo[1,2- a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate; 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-ethoxyiminoacetamido]-3-[(imidazo-[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate; 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-ethoxyiminoacetamido]-3-[(6-chloro- imidazo[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate; 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-methoxyiminoacetamido]-3-[(6-cyanoimidazo[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate ; 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-ethoxyiminoacetamido]-3-[(6-cyanoimidazo[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate ; 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-carboxymethoxyiminoacetamido]-3-[(6-cyanoimidazo[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate.

Claim 17

1 6 . A method f or producing a compound of the formula; wherein Z stands for S, S→O, O or CH 2 , R 4 stands for hydrogen atom, methoxy group or formamido group, R 13 stands for hydrogen atom, methyl group, hydroxyl group or halogen atom and A stands for an optionally substituted imidazol-1-yl group forming a condensed ring at the 2,3- or 3,4-position or a physiologically or pharmaceutically acceptable salt or ester thereof, which comprises allowing a compound of the formula; wherein R 5 stands for hydroxyl group, acyloxy group, carbamoyloxy group, substituted carbamoyloxy group or halogen atom and other symbols are of the same meaning as defined above or a salt or ester thereof to react with an optionally substituted imidazole forming a condensed ring at the 2,3- or 3,4-position or a salt thereof.

Claim 18

1 6 . A method f or producing a compound of the formula; wherein Z stands for S, S→O, O or CH 2 , R 4 stands for hydrogen atom, methoxy group or formamido group, R 13 stands for hydrogen atom, methyl group, hydroxyl group or halogen atom and A stands for an optionally substituted imidazol-1-yl group forming a condensed ring at the 2,3- or 3,4-position or a physiologically or pharmaceutically acceptable salt or ester thereof, which comprises allowing a compound of the formula; wherein R 5 stands for hydroxyl group, acyloxy group, carbamoyloxy group, substituted carbamoyloxy group or halogen atom and other symbols are of the same meaning as defined above or a salt or ester thereof to react with an optionally substituted imidazole forming a condensed ring at the 2,3- or 3,4-position or a salt thereof.

Claim 29

22 . A pharmaceutical composition containing at least one of the compounds of the formula; wherein R 0 stands for hydrogen atom, nitrogen-containing heterocyclic group, acyl group or esterified carboxyl group, Z stands for S, S→O, 0 or CH 2 , R 4 stands for hydrogen atom, methoxy group or formamido group, R 13 stands for hydrogen atom, methyl group, hydroxyl group or halogen atom and A stands for an optionally substituted imidazol-1-yl group forming a condensed ring at the 2,3-or 3,4-position or physiologically or pharmaceutically acceptable salts or esters thereof.

Claim 30

22 . A pharmaceutical composition containing at least one of the compounds of the formula; wherein R 0 stands for hydrogen atom, nitrogen-containing heterocyclic group, acyl group or esterified carboxyl group, Z stands for S, S→O, 0 or CH 2 , R 4 stands for hydrogen atom, methoxy group or formamido group, R 13 stands for hydrogen atom, methyl group, hydroxyl group or halogen atom and A stands for an optionally substituted imidazol-1-yl group forming a condensed ring at the 2,3-or 3,4-position or physiologically or pharmaceutically acceptable salts or esters thereof.