.beta.-lactam antibacterial agents and compositions containing them

A pharmaceutical composition useful for treating bacterial infections in humans and animals which comprises an antibacterially effective amount of a compound of the formula (I) or a pharmaceutically acceptable salt or in-vivo hydrolysable ester thereof:

• ##STR27## wherein R.sup.1 is phenyl, substituted phenyl or a 5- or 6-membered heterocyclic ring containing up to three heteroatoms selected from the group consisting of oxygen, sulphur and nitrogen, optionally substituted with hydroxy, amino, halogen or alkoxy of 1 to 6 carbon atoms;
• X represents ##STR28## wherein R.sup.y is methyl or acetyl;
• R.sup.2 and R.sup.3 may be the same or different and each is hydrogen, an aryl group, a heterocyclyl group or an alkyl group of 1 to 6 carbon atoms optionally substituted by an aryl group or a heterocyclyl group;
• and R.sup.4 is hydrogen, an alkylcarbonyl group of 1 to 6 carbon atoms in the alkyl moiety, an aryl group, a heterocyclyl group, an alkyl group of 1 to 6 carbon atoms optionally substituted by an aryl group or a heterocyclyl group;
• R.sup.5 represents hydrogen, methoxy or --NHCHO;
• and Y is:
• ##STR29## wherein Y.sup.1 is oxygen, sulphur or --CH.sub.2 -- and Z represents hydrogen, halogen, alkoxy of 1 to 4 carbon atoms, --CH.sub.2 Q or --CH.dbd.CH--Q wherein Q represents hydrogen, halogen, hydroxy, mercapto, cyano, carboxy, carbamoyloxy carboxylic ester, alkyloxy of 1 to 4 carbon atoms, acyloxy, aryl, a heterocyclyl group bonded via carbon, a heterocyclylthio group or a nitrogen containing heterocyclic group bonded via nitrogen and the carbon atom marked * is asymmetric, in combination with a pharmaceutically acceptable carrier.

A method of treating bacterial infections in humans and animals which comprises administering to a human or animal in need thereof an antibacterially effective amount of a compound of the formula (I) or a pharmaceutically acceptable salt or in-vivo hydrolysable ester thereof:

• ##STR31## wherein R.sup.1 is phenyl, substituted phenyl or a 5- or 6-membered heterocyclic ring containing up to three heteratoms selected from the group consisting of oxygen, sulphur and nitrogen, optionally substituted with hydroxy, amino, halogen or alkoxy of 1 to 6 carbon atoms;
• X represents ##STR32## wherein R.sup.y is methyl or acetyl;
• R.sup.2 and R.sup.3 may be the same or different and each is hydrogen, an aryl group, a heterocyclyl group or an alkyl group of 1 to 6 carbon atoms optionally substituted by an aryl group or a heterocyclyl group;
• and R.sup.4 is hydrogen, an alkylcarbonyl group of 1 to 6 carbon atoms in the alkyl moiety, an aryl group, a heterocyclyl group, an alkyl group of 1 to 6 carbon atoms optionally substituted by an aryl group or a heterocyclyl group;
• R.sup.5 represents hydrogen, methoxy or --NHCHO;
• and Y is:
• ##STR33## wherein Y.sup.1 is oxygen, sulphur or --CH.sub.2 -- and Z represents hydrogen, halogen, alkoxy of 1 to 4 carbon atoms, --CH.sub.2 Q or --CH.dbd.CH--Q wherein Q represents hydrogen, halogen, hydroxy, mercapto, cyano, carboxy, carbamoyloxy carboxylic ester, alkyloxy of 1 to 4 carbon atoms, acyloxy, aryl, a heterocyclyl group bonded via carbon, a heterocyclylthio group or a nitrogen containing heterocyclic group bonded via nitrogen and the carbon atom marked * is asymmetric, in combination with a pharmaceutically acceptable carrier.

A pharmaceutical composition useful for treating bacterial infections in humans and animals which comprises an antibacterially effective amount of a compound of the formula (I) or a pharmaceutically acceptable salt or in-vivo hydrolysable ester thereof:

• ##STR35## wherein R.sup.1 is phenyl, substituted phenyl or a 5- or 6-membered heterocyclic ring containing up to three heteroatoms selected from the group consisting of oxygen, sulphur and nitrogen, optionally substituted with hydroxy, amino, halogen or alkoxy of 1 to 6 carbon atoms;
• X represents ##STR36## wherein R.sup.y is methyl or acetyl;
• R.sup.2 and R.sup.3 may be the same or different and each is hydrogen, an aryl group, a heterocyclyl group or an alkyl group of 1 to 6 carbon atoms optionally substituted by an aryl group or a heterocyclyl group;
• and R.sup.4 is hydrogen, an alkylcarbonyl group of 1 to 6 carbon atoms in the alkyl moiety, an aryl group, a heterocyclyl group, an alkyl group of 1 to 6 carbon atoms optionally substituted by an aryl group or a heterocyclyl group;
• R.sup.5 represents hydrogen, methoxy or --NHCHO;
• and Y is;
• ##STR37## wherein Y.sup.1 is oxygen, sulphur or --CH.sub.2 -- and Z represents hydrogen, halogen, alkoxy of 1 to 4 carbon atoms, --CH.sub.2 Q or --CH.dbd.CH--Q wherein Q represents hydrogen, halogen, hydroxy, mercapto, cyano, carboxy, carbamoyloxy carboxylic ester, alkyloxy of 1 to 4 carbon atoms, acyloxy, aryl, a heterocyclyl group bonded via carbon, a heterocyclylthio group or a nitrogen containing heterocyclic group bonded via nitrogen and the carbon atom marked * is asymmetric, and a beta-lactamase inhibitory amount of a beta-lactamase inhibitor, in combination with a pharmaceutically acceptable carrier.