.beta.-lactam antibiotics

A compound of the formula ##STR28## wherein R is allyloxycarbonyl, t=butoxycarbonyl, naphthyloxycarbonyl, trichloroethyloxycarbonl, p-nitro benzyloxycarbonyl, benzhydryloxycarbonyl, p-methoxybenzl oxycarbonyl, o-nitrobenzyloxycarbonyl or acetoxy;

• wherein R.sup.4 is phenoxyacetyl, phenylacetyl, C.sub.1 to C.sub.6 alkanoyl or chloracetyl, and wherein A and A' are taken together to form a group of the formula ##STR29## wherein R.sup.1 is a carboxy-protecting group;
• X is oxygen and R.sup.2 is hydrogen, halo, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 alkyl substituted by one or two halogen, hydroxy, protected hydroxy, amino, protected amino, C.sub.1 to C.sub.7 acyloxy, nitro, carboxy, protected carboxy, carbamoyl, carbamoyloxy, cyano, methylsulfonylamino or C.sub.1 to C.sub.4 alkoxy;
• C.sub.1 to C.sub.6 alkylthio, C.sub.1 to C.sub.6 alkylthio substituted by one or two halogen, hydroxy, protected hydroxy, amino, protected amino, C.sub.1 to C.sub.7 acyloxy, nitro, carboxy, protected carboxy, carbamoyl, carbamoyloxy, cyano, methylsulfonylamino or C.sub.1 to C.sub.4 alkoxy;
• C.sub.7 to C.sub.12 aryalkyl, C.sub.7 to C.sub.12 arylalkyl substituted on the alkyl position with one or two groups chosen from halogen, hydroxy, protected hydroxy, amino, protected amino, C.sub.1 to C.sub.7 acyloxy, nitro carboxy, protected carboxy, carbamoyl, carbamoyloxy, cyano, C.sub.1 to C.sub.6 alkylthio, methylsulfonylamino or C.sub.1 to C.sub.4 alkoxy;
• and/or the phenyl group of the arylalkyl being substituted with 1 or 2 groups chosen from halogen, hydroxy, protected hydroxy, nitro, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.4 alkoxy, carboxy, protected carboxy, carboxymethyl, protected carboxymethyl, hydroxymethyl, protected hydroxymethyl, aminomethyl, protected aminomethyl, or methylsulfonylamino;
• phenyl or phenyl substituted with one or two moieties chosen from the group consisting of halogen, hydroxy, protected hydroxy, cyano, nitro, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.4 alkoxy, carboxy, protected carboxy, carboxymethyl, protected carboxymethyl, hydroxymethyl, protected hydroxymethyl, aminomethyl, protected aminomethyl, trifluoromethyl or methylsulfonylamino;
• a group of the formula
• --CY.sub.3
• wherein Y is fluoro, chloro, bromo or iodo;
• a group of the formula
• --COR.sup.6
• wherein R.sup.6 is hydrogen, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 alkyl substituted by one or two halogen, hydroxy, protected hydroxy, amino, protected amino, C.sub.1 to C.sub.7 acyloxy, nitro, carboxy, protected carboxy, carbamoyl, carbamoyloxy, cyano, methylsulfonylamino or C.sub.1 to C.sub.4 akloxy;
• C.sub.7 to C.sub.12 arylalkyl, C.sub.7 to C.sub.12 arylalkyl substituted on the alkyl position with one or two groups chosen from halogen, hydroxy, protected hydroxy, amino, protected amino, C.sub.1 to C.sub.7 acyloxy, nitro, carboxy, protected carboxy, carbamoyl, carbamoyloxy, cyano, C.sub.1 to C.sub.6 alkylthio, methylsulfonylamino or C.sub.1 -C.sub.4 alkoxy;
• and/or the phenyl group fo the arylalkyl being substituted with 1 or 2 groups chosen from halogen, hydroxy, protected hydroxy, nitro, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.4 alkoxy, carboxy, protected carboxy, carboxymethyl, protected carboxymethyl, hydroxymethyl, protected hydroxymethyl, aminomethyl, protected aminomethyl, or methylsulfonylamino;
• phenyl, phenyl substituted with one or two moieties chosen from the group consisting of halogen, hydroxy, protected hydroxy, cyano, nitro, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.4 alkoxy, carboxy, protected carboxy, carboxymethyl, protected carboxymethyl, hydroxymethyl, protected hydroxymethyl, aminomethyl, protected aminomethyl, trifluoromethyl or methylsulfonylamino;
• amino, amino substituted once with C.sub.1 to C.sub.6 alkyl, C.sub.7 to C.sub.12 arylalkyl, phenyl, or phenyl substituted with one or two moieties chosen from the group consisting of halogen, hydroxy, protected hydroxy, cyano, nitro, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.4 alkoxy, carboxy, protected carboxy, carboxymethyl, protected carboxymethyl, hydroxymethyl, protected hydroxymethyl, aminomethyl, protected aminomethyl, trifluoromethyl or methylsulfonylamino;
• or amino substituted with two substituents chosen from the group consisting of C.sub.1 to C.sub.6 alkyl, C.sub.7 to C.sub.12 arylalkyl;
• phenyl, phenyl substituted with one or two moietis chosen from the group consisting of halogen, hydroxy, protected hydroxy, cyano, nitro, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.4 alkoxy, carboxy, protected carboxy, carboxymethyl, protected carboxymethyl, hydroxymethyl, protected hydroxymethyl, aminomethyl, protected aminomethyl, trifluoromethyl or methylsulfonylamino;
• or R.sup.2 is a group of the formula
• --COOR.sup.7
• wherein R.sup.7 is hydrogen, an organic or inorganic cation, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 alkyl substituted by one or two halogen, hydroxy, protected hydroxy, amino, protected amino, C.sub.1 to C.sub.7 acyloxy, nitro, carboxy, protected carboxy, carbamoyl, carbamoyloxy, cyano, methylsulfonylamino or C.sub.1 to C.sub.4 alkoxy;
• C.sub.7 to C.sub.12 arylalkyl, C.sub.7 to C.sub.12 arylalkyl substituted on the alkyl position with one or two groups chosen from halogen, hydroxy, protected hydroxy, amino, protected amino, C.sub.1 to C.sub.7 acyloxy, nitro carboxy, protected carboxy, carbamoyl, carbamoyloxy, cyano, C.sub.1 to C.sub.6 alkylthio, methylsulfonylamino or C.sub.1 -C.sub.4 alkoxy, and/or the phenyl gorup of the arylalkyl being substituted with 1 or 2 groups chosen from halogen, hydroxy, protected hydroxy, nitro, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.4 alkoxy, carboxy, protected carboxy, carboxymethyl, protected carboxymethyl, hydroxymethyl, protected hydroxymethyl, aminomethyl, protected aminomethyl, or methylsulfonylamino;
• a carboxy-protecting group or a non-toxic metabolically-labile, ester-forming group;
• or R.sub.2 is a group of the formula
• --CH.sub.2 --S--"Heterocyclic";
• or R.sub.2 is a group of the formula
• --S--"Heterocyclic"
• said "heterocyclic" being an optionally substituted 5-membered or 6 -membered ring having 1 to 4 heteratoms selected from oxygen, sulfur, or nitrogen, said heterocyclic optionally fused to an aromatic 5-membered or 6-membered ring;
• or R.sub.2 is a group of the formula
• --OR.sup.9
• wherein R.sup.9 is hydrogen, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 alkyl substituted by one or two halogen, hydroxy, protected hydroxy, amino, protected amino, C.sub.1 to C.sub.7 acyloxy, nitro, carboxy, protected carboxy, carbamoyl, carbamoyloxy, cyano, methylsulfonylamino or C.sub.1 to C.sub.4 alkoxy;
• C.sub.7 to C.sub.12 arylalkyl, C.sub.7 to C.sub.12 arylalkyl substituted on the alkyl position with one or two groups chosen from halogen, hydroxy, protected hydroxy, amino, protected amino, C.sub.1 to C.sub.7 acyloxy, nitro carboxy, protected carboxy, carbamoyl, carbamoyloxy, cyano, C.sub.1 to C.sub.6