Carbapenem antibiotic compounds

A carbapenem compound of formula (I):

• ##STR18## wherein:
• R.sup.1 is 1-hydroxyethyl, 1-fluoroethyl or hydroxymethyl;
• R.sup.2 is hydrogen or C.sub.1-4 alkyl;
• R.sup.3 is hydrogen or C.sub.1-4 alkyl;
• R.sup.4 is hydroxy or carboxy;
• and
• the phenyl ring is optionally further substituted by one or two substituents selected from halo, cyano, C.sub.1-4 alkyl, nitro, hydroxy, carboxy, C.sub.1-4 alkoxy, trifluoromethyl, C.sub.1-4 alkoxycarbonyl, carbamoyl, C.sub.1-4 alkycarbamoyl, di-C.sub.1-4 alkylcarbamoyl, amino, C.sub.1-4 alkylamino, di-C.sub.1-4 alkylamino, sulphonic acid, C.sub.1-4 alkylS(O).sub.n -- (wherein n is 0-2), N-C.sub.1-4 alkanesulphonamido, C.sub.1-4 alkanoylamino and C.sub.1-4 alkanoyl (N-C.sub.1-4 alkyl)amino:
• provided that the phenyl ring is substituted by at least one carboxy;
• or a non pharmaceutically acceptable salt thereof.

A compound of the formula (V):

• ##STR19## wherein:
• R.sup.2 is hydrogen or C.sub.1-4 alkyl;
• R.sup.10 is hydrogen or C.sub.1-4 alkyl, or an amino protecting group;
• R.sup.13 is 1-hydroxyethyl, 1-fluoroethyl or hydroxymethyl, protected hydroxymethyl or 1-(protected hydroxy) ethyl;
• R.sup.11 is hydrogen or a carboxy protecting group;
• R.sup.12 is hydrogen or an amino protecting group;
• R.sup.18 is carboxy, hydroxy, a protected carboxy group or a protected hydroxy group;
• and the phenyl ring is optionally further substituted by one or two substituents selected from halo, cyano, C.sub.1-4 alkyl, nitro, hydroxy, carboxy, C.sub.1-4 alkoxy, trifluoromethyl, C.sub.1-4 alkoxycarbonyl, carbamoyl, C.sub.1-4 alkycarbamoyl, di-C.sub.1-4 alkylcarbamoyl, amino, C.sub.1-4 alkylamino, di-C.sub.1-4 alkylamino, sulphonic acid, C.sub.1-4 alkylS(O).sub.n --, wherein n is 0-2, N-C.sub.1-4 alkanesulphonamido, C.sub.1-4 alkanoylamino and C.sub.1-4 alkanoyl (N-C.sub.1-4 alkyl)amino:
• provided that at least one protecting group is present, and the phenyl ring is substituted by at least one carboxy.

A method of treatment of a bacterial infection by administering to a patient in need thereof an antibacterially effective amount of a carbapenem compound of formula (I):

• ##STR20## wherein:
• R.sup.1 is 1-hydroxyethyl, 1-fluoroethyl or hydroxymethyl;
• R.sup.2 is hydrogen or C.sub.1-4 alkyl;
• R.sup.3 is hydrogen or C.sub.1-4 alkyl;
• R.sup.4 is hydroxy or carboxy;
• and
• the phenyl ring is optionally further substituted by one or two substituents selected from halo, cyano, C.sub.1-4 alkyl, nitro, hydroxy, carboxy, C.sub.1-4 alkoxy, trifluoromethyl, C.sub.1-4 alkoxycarbonyl.sub., carbomoyl, C.sub.1-4 alkycarbamoyl, di-C.sub.1-4 alkylcarbamoyl, amino, C.sub.1-4 alkylamino, di-C.sub.1-4 alkylamino, sulphonic acid, C.sub.1-4 alkylS(O).sub.n --, wherein n is 0-2, N-C.sub.1-4 alkanesulphonamido, C.sub.1-4 alkanoylamino and C.sub.1-4 alkanoyl (N-C.sub.1-4 alkyl) amino:
• provided that the phenyl ring is substituted by at least one carboxy;
• or a pharmaceutically acceptable salt or in vivo hydrolysable ester thereof.