7-Amino-thiadiazole oxyimino derivatives of cephem and cepham compounds

7-substituted-3-cephem and cepham-4-carboxylic acid of the formula:

• ##STR26## where R.sup.1 is amino or a protected amino;
• R.sup.2 is hydrogen;
• carbamoyl;
• lower alkanoyl;
• lower alkoxycarbonyl;
• aroyl;
• ar(lower) alkanoyl;
• cyclo(lower) alkyl(lower) alkanoyl;
• ar(lower) alkoxycarbonyl;
• (lower) alkanesulfonyl;
• arenesulfonyl;
• aryl;
• alkaryl;
• aryl and alkaryl substituted in the aryl nucleus with 1 to 3 substituents selected from the group consisting of halogen, lower alkoxy, nitro, halo(lower)alkyl, and protected carboxy;
• substituted lower alkyl selected from the group consisting of ar(lower)alkyl, lower alkylthio(lower)alkyl, halo(lower)alkyl, aryloxy(lower)alkyl, cyano(lower)alkyl, protected carboxy(lower)alkyl, di(lower)alkylcarbamoyl(lower)alkyl, lower alkoxy(lower)alkoxy(lower)alkyl, lower alkanesulfonyl(lower)alkyl, protected amino(lower)alkyl, amino(lower)alkyl, carboxyl(lower)alkyl, ar(lower)alkyl substituted with protected carboxy, ar(lower)alkyl substituted with carboxy, ar(lower)alkyl substituted with protected amino(lower)alkyl, and ar(lower)alkyl substituted with amino(lower)alkyl;
• lower alkenyl;
• lower alkynyl;
• cycloalkyl;
• cycloalkyl substituted with carboxy or protected carboxy;
• cyclo(lower)alkenyl;
• or S or O containing 5-membered heterocyclic group substituted with an oxo group;
• R.sup.3 is hydrogen or lower alkyl;
• R.sup.4 is hydrogen;
• acyloxy(lower)alkyl;
• acylthio(lower)alkyl;
• pyridinium(lower)alkyl;
• pyridinium(lower)alkyl substituted with carbamoyl, lower alkanoyl, hydroxy(lower)alkyl, carboxy(lower)alkyl, or hydroxy iminomethyl;
• thiazolium(lower)alkyl;
• thiazolium(lower)alkyl substituted with lower alkyl or hydroxy(lower)alkyl;
• heterocyclicthio(lower)alkyl;
• heterocyclicthio(lower)alkyl substituted with 1 to 3 substituent(s) selected from the group consisting of lower alkyl, hydroxy(lower)alkyl, protected amino(lower)alkyl, amino(lower)alkyl, di(lower)alkylamino(lower)alkyl, lower alkenyl, carboxy(lower)alkyl, protected carboxy(lower)alkyl, aryl, morpholino(lower)alkyl, piperidino(lower)alkyl, lower alkyl substituted piperazinyl(lower)alkyl, oxo and hydroxy;
• lower alkyl;
• halogen;
• or hydroxy;
• R.sup.5 is carboxy or a protected carboxy;
• wherein R.sup.5 is COO.sup.- when R.sup.4 is pyridinium(lower)alkyl or substituted pyridinium(lower)alkyl, or thiazolium(lower)alkyl or substituted thiazolium(lower)alkyl;
• and the heavy solid line means single or double bond;
• and pharmaceutically acceptable salt thereof.