Cephalosporin compounds

A compound of the formula:

• ##STR189## wherein R.sup.0 stands for:
• (i) hydrogen;
• (ii) 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1H-tetrazolyl, 2H-tetrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 4-isothiazolyl, 5-isothiazolyl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyridyl-N-oxide, 3-pyridyl-N-oxide, 4-pyridyl-N-oxide, 3-pyridazinyl, 4-pyridazinyl, 3-pyridazinyl-N-oxide, 4-pyridazinyl-N-oxide, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrimidinyl-N-oxide, 4-pyrimidinyl-N-oxide, 5-pyrimidinyl-N-oxide, pyrazinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, piperazinyl, 3H-indol-2-yl, or 3H-indol-3-yl that is unsubstituted or substituted by one to three of C.sub.1-6 alkyl group, C.sub.3-10 cycloalkyl group, C.sub.6-10 aryl group, C.sub.7-12 aralkyl group, hydroxyl group, C.sub.1-6 alkoxy group, mercapto group, C.sub.1-6 alkylthio group, amino group, mono-C.sub.1-6 alkylamino group, di-C.sub.1-6 alkylamino group, halogen atom, nitro group, azido group, cyano group, carboxyl group, C.sub.1-10 alkoxycarbonyl group, C.sub.1-6 alkanoyl group, C.sub.1-6 alkanoyloxy group, carbamoyl group, mono-C.sub.1-6 alkylcarbamoyl group, di-C.sub.1-6 alkyl-carbamoyl group, carbamoyloxy group, mono-C.sub.1-6 alkylcarbamoyl-oxy group, or di-C.sub.1-6 alkylcarbamoyloxy group;
• (iii) a group of the formula ##STR190## wherein R.sup.1 stands for an amino group or a protected amino group, R.sup.2 stands for hydrogen atom, halogen atom, or nitro group, and R.sup.3 stands for hydrogen atom or C.sub.1-6 alkyl group, C.sub.2-6 alkenyl group, C.sub.2-6 alkynyl group, C.sub.3-10 cycloalkyl group or C.sub.5-6 cycloalkenyl group that is unsubstituted or substituted by one or two of hydroxyl, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.3-10 cycloalkyl, C.sub.5-6 cycloalkenyl, C.sub.6-10 aryl, C.sub.7-19 aralkyl, 2- or 3-pyrrolyl, 3-,4- or 5-pyrazolyl, 2-, 4- or 5-imidazolyl, 1,2,3-or 1,2,4-triazolyl, 1H- or 2H-tetrazolyl, 2- or 3-furyl, 2- or 3-thienyl, 2-, 4- or 5-oxazolyl, 3-, 4- or 5-isoxazolyl, 1,2,3-oxadiazol-4- or 5-yl, 1,2,4-oxadiazol-3- or 5-yl, 1,2,5- or 1,3,4-oxadiazolyl, 2-, 4- or 5-thiazolyl, 3-, 4- or 5-isothiazolyl, 1,2,3-thiazidazol-4- or 5-yl, 1,2,4-thiadiazol-3- or 5-yl, 1,2,5- or 1,3,4-thiadiazolyl, 2- or 3-pyrrolidinyl, 2-, 3- or 4-pyridyl, 2-, 3- or 4-pyridyl-N-oxide, 3- or 4-pyridazinyl, 3- or 4-pyridazinyl-N-oxide, 2-, 4- or 5-pyrimidinyl, 2-, 4- or 5-pyrimidinyl-N-oxide, pyrazinyl, 2-, 3- or 4-piperidinyl, piperazinyl, 3H-indol-2- or 3-yl, 2-, 3- 4-pyranyl, 2-, 3- or 4-thiopyranyl, benzopyranyl, quinolyl, pyrido[2,3-d]pyrimidyl, 1,5-, 1,6-, 1,7-, 1,8-, 2,6- or 2,7-naphthylidyl, thieno[2,3-d]-pyridyl, pyrimidopyrimidyl, pyrazinoquinolyl, benzopyranyl, C.sub.1-6 alkoxy, C.sub.3-10 cycloalkyloxy, C.sub.6-10 aryloxy, C.sub.7-19 aralkyloxy, thiazolyloxy, mercapto, C.sub.1-6 alkylthio, C.sub.3-10 cycloalkylthio, C.sub.6-10 arylthio, C.sub.7-19 aralkylthio, thiazolylthio, amino, mono-C.sub.1-6 alkylamino, di-C.sub.1-6 alkylamino, tri-C.sub.1-6 alkylammonium, C.sub.3-10 cycloalkylamino, C.sub. 6-10 arylamino, C.sub.7-19 aralkylamino, thiazolylamino, thiadiazolylamino, cyclic amino, azido, nitro, halogen, cyano, carboxyl, C.sub.1-10 alkloxy-carbonyl, C.sub.6-10 aryloxycarbonyl, C.sub.7-19 aralkyloxy-carbonyl, benzoyl, naphthoyl, phthaloyl, phenylacetyl, C.sub.1-6 alkanoyl, C.sub.3-5 alkenoyl, benzoyloxy, naphthoyloxy, phenylacetoxy, C.sub.2-6 alkanoyloxy, C.sub.3-5 alkenoyloxy, carbamoyl, N-methylcarbamoyl, N,N-dimethylcarbamoyl, N-ethylcarbamoyl, N,N-diethylcarbamoyl, N-phenylcarbamoyl, N-acetylcarbamoyl, N-benzoylcarbamoyl, N-(p-methoxy-phenyl)carbamoyl, pyrrolidinocarbonyl, piperidinocarbonyl, piperazinocarbonyl, morpholino-carbonyl, thiocarbamoyl, N-methylthiocarbamoyl, N-phenylthiocarbamoyl, carbamoyloxy, N-methylcarbamoyloxy, N,N-dimethylcarbamoyloxy, N-ethylcarbamoyloxy, N-phenylcarbamoyloxy, phthalimido, C.sub.1-6 alkanoylamino, benzamido, naphthoylamido, phthalimido, carboxyamino, C.sub.1-10 alkoxy-carboxamido, C.sub.6-10 aryloxy-carboxamido or C.sub.7-19 aralkyloxy-carboxamido;
• or
• (iv) methoxy-carbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxy-carbonyl, n-butoxycarbonyl, tert-butoxycarbonyl, cyclohexyloxycarbonyl, norbornyloxycarbonyl, phenoxycarbonyl, naphthyloxycarbonyl, benzyloxycarbonyl, methoxymethyl-oxycarbonyl, acetylmethyloxycarbonyl, 2-trimethylsilyl-ethoxycarbonyl, 2-methanesulfonylethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl, 2-cyanoethoxycarbonyl, p-methylphenoxycarbonyl, p-methoxyphenoxycarbonyl, p-chlorophenoxycarbonyl, p-methylbenzyloxycarbonyl, p-methoxybenzyloxycarbonyl, p-chlorobenzyloxycarbonyl, p-nitrobenzyloxycarbonyl, benzhydryloxycarbonyl, cyclopropyloxycarbonyl, cyclopentyloxycarbonyl, or cyclohexyloxycarbonyl;
• R.sup.4 stands for hydrogen atom, methoxy group or formamido group,
• Z stands for S or S.fwdarw.O;
• R.sup.13 stands for hydrogen atom, methyl group, hydroxyl group or halogen atom;
• and
• A stands for substituted or unsubstituted 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.