Carbapenem derivatives having antibiotic activity, their preparation and their use

A compound of formula (I):

• ##STR26## in which:
• A is a fully saturated heterocyclic group having from 4 to 6 ring atoms, of which one is a nitrogen atom and the remainder are carbon atoms, said nitrogen atom having on its remaining valence a group or atom R.sup.4, wherein:
• R.sup.4 is a hydrogen atom;
• an alkenyl group having from 2 to 5 carbon atoms;
• an alkynyl group having from 2 to 5 carbon atoms;
• an alkyl group having from 1 to 6 carbon atoms;
• a substituted alkyl group having from 1 to 6 carbon atoms and having at least one substituent selected from the group consisting of substituents (a), defined below;
• or a group of formula --C(.dbd.NH)R.sup.5, wherein R.sup.5 is a hydrogen atom or an alkyl group having from 1 to 6 carbon atoms;
• R.sup.1 is a hydrogen atom or a methyl group;
• R.sup.2 is a hydrogen atom or an alkyl group having from 1 to 6 carbon atoms;
• R.sup.3 is a hydrogen atom or a negative ionic charge or forms an ester;
• Q is
• (i) a group of formula --B--N.sup.+ R.sup.8 R.sup.9 R.sup.10, wherein:
• R.sup.8, R.sup.9 and R.sup.10 are independently selected from the group consisting of alkenyl groups having from 2 to 5 carbon atoms, alkynyl groups having from 2 to 5 carbon atoms, alkyl groups having from 1 to 6 carbon atoms and substituted alkyl groups which have from 1 to 6 carbon atoms and which have at least one substituent selected from the group consisting of substituents (b), defined below;
• and B represents an alkylene or alkylidene group having from 1 to 4 carbon atoms;
• substituents (a):
• hydroxy groups, carboxy groups, cyano groups, sulfamoyl groups, sulfo groups, halogen atoms, and groups of formula --NR.sup.a R.sup.b or --CONR.sup.a R.sup.b, where R.sup.a and R.sup.b are independently selected from the group consisting of hydrogen atoms and alkyl groups having from 1 to 4 carbon atoms;
• substituents (b):
• hydroxy groups;
• carboxy groups;
• groups of formula --NR.sup.a R.sup.b, where R.sup.a and R.sup.b are as defined above;
• groups of formula --CONR.sup.c R.sup.d or --OCONR.sup.c R.sup.d, where R.sup.c and R.sup.d are independently selected from the group consisting of hydrogen atoms, alkyl groups having from 1 to 4 carbon atoms and substituted alkyl groups which have from 1 to 4 carbon atoms and which have at least one substituent selected from the group consisting of substituents (d) defined below;
• cyano groups;
• sulfamoyl groups;
• ureido groups;
• sulfo groups;
• halogen atoms;
• alkoxy groups having from 1 to 4 carbon atoms;
• alkoxycarbonyl groups having from 2 to 5 carbon atoms;
• alkanoyl groups having from 1 to 4 carbon atoms;
• alkanoylamino groups having from 1 to 4 carbon atoms;
• alkanoyloxy groups having from 1 to 4 carbon atoms;
• alkylthio groups having from 1 to 4 carbon atoms;
• alkylsulfinyl groups having from 1 to 4 carbon atoms and alkylsulfonyl groups having from 1 to 4 carbon atoms;
• substituents (d):
• hydroxy groups, carboxy groups and groups of formula --CONR.sup.a R.sup.b or --OCONR.sup.a R.sup.b, where R.sup.a and R.sup.b are as defined above;
• or a pharmaceutically acceptable salt thereof and, where R.sup.3 is a hydrogen atom or forms an ester compound, the compound also includes an anion provided by a pharmaceutically acceptable acid.