1-Carba(dethia)cephalosporin antibiotics

A compound of Formula (1):

• ##STR19## wherein X is a group selected from amino, halo, cyano, hydrogen, nitro, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 substituted alkyl, a C.sub.3 to C.sub.6 heterocyclic ring containing 1, 2, or 3 nitrogen atoms and 0 or 1 sulfur or oxygen atoms, said ring optionally substituted by one or more groups selected from halo, nitro, hydroxy, C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 substituted alkyl;
• phenyl, substituted phenyl, or an acyl group of the formula ##STR20## wherein R" is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 substituted alkyl, phenyl, or substituted phenyl;
• R.sup.3 is hydrogen, C.sub.1 -C.sub.4 alkoxy, or a group of the formula --NHCHO;
• and R.sup.1 is an acyl group of the formula ##STR21## wherein R.sup.2 is hydrogen;
• C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkyl substituted by cyano, carboxy, halogen, amino, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, or trifluoromethylthio;
• a phenyl or substituted phenyl group represented by the formula ##STR22## wherein a and a' independently are hydrogen, halogen, hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkanoyloxy, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio, amino, mono- or di(C.sub.1 -C.sub.4 alkyl)amino, C.sub.1 -C.sub.4 carboxy, carbamoyl, hydroxymethyl, aminomethyl, or carboxymethyl;
• a group represented by the formula ##STR23## wherein a and a' have the same meanings as defined above, Z is 0 or S, and m is 0 or 1;
• a heteroarylmethyl group represented by the formula
• R.sub.1 --CH.sub.2 --
• wherein R.sub.1 is thienyl, furyl, benzothienyl, benzofuryl, indolyl, triazolyl, tetrazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, and such heteroaryl groups substituted by amino, hydroxy, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylsulfonylamino;
• a substituted methyl group represented by the formula ##STR24## wherein R.sub.2 is cyclohex-1,4-dienyl, or a phenyl group or substituted phenyl group represented by the formula ##STR25## wherein a and a' have the above defined meanings, or R.sub.2 is R.sub.1 as defined above, and Q is hydroxy, C.sub.1 -C.sub.4 alkanoyloxy, carboxy, sulfo, or amino;
• or R.sup.2 is a keto group or an oximino-substituted group represented by the formulae ##STR26## wherein R.sub.3 is R.sub.1 or R.sub.2 as defined above and R.sub.4 is hydrogen, C.sub.1 -C.sub.4 alkyl, or a group represented by the formula ##STR27## wherein b and b' independently are hydrogen, or C.sub.1 -C.sub.3 alkyl, and b and b' when taken together with the carbon to which they are bonded form a 3- to 6-membered carbocyclic ring, R.sub.5 is hydroxy, C.sub.1 -C.sub.4 alkoxy, amino, C.sub.1 -C.sub.4 alkylamino, or di(C.sub.1 -C.sub.4 alkyl)amino;
• and n is 0, 1, 2, or 3;
• or a pharmaceutically acceptable salt thereof.