Antibacterial compounds, and use

Claim 2

A compound of the formula ##STR70## wherein R 0 is a group of the formula ##STR71## wherein R 1 is amino or an amino group which is protected by an amino protective group used in the field of β-lactams and peptides, R 2 is hydrogen, a halogen or nitro, R 3 is hydrogen, a C 1-6 alkyl group which is unsubstituted or substituted by hydroxy, a C 1-6 alkoxy or a di-C 1-6 alkylamino, or a C 2-6 alkynyl group, Z is S or S→O, R 4 is hydrogen, methoxy or formamido, R 13 is hydrogen, methyl, hydroxyl or a halogen, and A is a condensed cyclic group selected from the group consisting of imidazo[1,2-a]-pyridyl, imidazo[1,2-a]pyrazinyl, imidazo[1,2-a]pyrimdinyl, imidazo[1,5-a]pyridyl and imidazo[1,5-a]-pyridazinyl group, which is unsubstituted or substituted by a C 1-6 alkyl group, the number of the substituent being 1 to 2, or pharmaceutically acceptable salt thereof or a metabolically unstable, nontoxic ester thereof.

Claim 3

A compound of claim 1 which is 7β-[2-(2-aminothiazol-4-yl)2-(Z)-methoxyiminocetamido]-3-[(imidazo[1,2-a]pyridin-5-yl)thiomethyl]-3-cephem-4-carboxylic acid, β -[2-aminothiazol-4-yl)-2(Z) - ethoxyiminoacetamido]-3-[(imidazo(1,2-a) pyridin-5-yl)thiomethyl]-3-cephem-4-carboxylic acid, 7β-[2-(2-aminothiazol-4-yl)-2(Z)-propargyloxyiminacetamido]-3-[(imidazo[1,2-a]pyridin-5-yl)thiomethyl]-3-cephem-4-carboxylic acid, 7β-[2-(2-aminothiazol-4-yl)-2(Z)-(2-methoxyethyiminoacetamido]-3-[(imidazo[1,2-a]pyridin-5-yl)thiomethyl]-3-cephem-4-carboxylic acid, 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-(2-hydroxyethoxyiminoacetamido]-3-[(imidazo[1,2-a]pyridin-5-yl)thiomethyl]-3-cephem-3-carboxylic acid, 7β-[2-(2-aminothiazol-4-yl)-2(Z)-(2-dimethylaminoethoxyiminoacetamido]-3-[(imidazo[1,2-a]pyridin-5-yl)thiomethyl]-3-cephem-4-carboxylic acid, 7β-[2-(2-aminothiazol-4-yl)-2(Z)-methoxyiminoacetamido]-3-[(imidazo[1,2-a]pyrazin-5-yl)thiomethyl]-3-cephem-4-carboxylic acid or 7β-[2-(2-aminothiazol-4-yl)-2(Z)-methoxyiminoacetamido]-3[(5-methylimidazo[1,2-a]pyrimidin-7-yl)thiomethyl]-3-cephem-4-carboxylic acid, or a pharmaceutically acceptable salt thereof or a metabolicallyunstable, nontoix ester thereof.

Claim 4

A compound of claim 1 in which the pharmaceutically acceptable salt is an alkali metal salt.

Claim 5

A compound of claim 1 in whihc the pharmaceutically acceptable salt is a sodium salt.

Claim 6

A compound of claim 1 in which the metabolically unstable, nontoxic ester is a C 2-6 alkanoyloxy C 1-6 alkyl ester.

Claim 7

A compound of claim 1 in which the metabolically ustable, nontoxic ester is pivaloyloxymethyl, acetoxymethyl or 1-(acetoxy) ethyl ester.

Claim 8

An antibacterial composition comprising an antibacterially effective amount of the compound of the formula ##STR72## wherein the symbols are as defined in claim 1, or a pharmaceutically acceptable salt thereof or a metabolically unstable, nontoxic ester thereof and a pharmaceutically acceptable diluent or carrier.

Claim 9

An antibacterial composition of claim 7, which contains a compound which is 7β-[2-(2-aminothiazol-4-yl)2-(Z)-methoxyiminoacetamido]-3-[(imidazo[1,2-a]pyridin-5-yl)thiomethyl]-3-cephem-4-carboxylic acid, 7β-[2-aminothiazol-4-yl)-2-(Z)-ethoxyiminoacetamido]-3-[(imidazo[1,2-a]pyridin-5-yl)thiomethyl]-3-cephem-4-carboxylic acid, 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-propargyloxyiminoacetamido]-3-[(imidazo[1,2-a)pyridin-5-yl)thiomethyl]-3-cephem-4-carboxylic acid, β -[2-(2-aminothiazol-4-yl)-2-(Z)-(2-methoxyethoxyiminoacetamido]-3-[(imidazo[1,2-a]pyrindin-5-yl)thiomethyl]-3-cephem-4-carboxylic acid, 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-(2-hydroxyethoxyiminoacetamido]-3-[(imidazo[1,2-a]pyridin-5-yl)thiomethyl]-3-cephem-4-carboxylic acid, 7β-[2-(2-aminothiazol-4-yl)-2(Z)-(2-dimethylaminoethoxyiminoacetamido]-3-[(imidazo[1,2-a]pyridin-5-yl)thiomethyl]-3-cephem-4-carboxylic acid, 7β-[2-(2-aminothiazol-4-yl)-2(Z)-methoxyiminoacetamido]-3-[(imidazo[1,2-a]pryazin-5-yl)thiomethyl]-3-cephem-4-carboxylic acid or 7β-[2-(2-aminothiazol-4-yl)-2(Z)-methoxyiminoacetamido]-3-[(5-methylimidazo[1,2-a]pyrimidin-7-yl)thiomethyl]-3-cephem-4-carboxylic acid, or a pharmaceutically acceptable salt thereof or a metabolically untable, nontoxic ester thereof.

Claim 10

An antibacterial composition of claim 7 in which the pharmaceutaically acceptable salt is an alkali metal salt.

Claim 11

An antibacterial composition of claim 7 in which the pharmaceutically acceptable salt is a sodium salt.

Claim 12

An antibaoterial composition of claim 7 which contains a metabolically unstable, nontoxic ester which is a C 2-6 alkanoyloxy C 1-6 alkyl ester.

Claim 13

An antibacterial composition of claim 7 in which the metabolically unstable, nontoxic ester is a pivaloyloxymethyl, acetoxymethyl or 1-(acetoxy)ethyl ester.