Carbapenem compounds, and compositions containing them

Abstract

Compounds of formula (I): ##STR1## .[.[.]. wherein: R 1 .[.represents a hydrogen atom, an alkyl group, an alkoxy group or various substituted alkyl groups.]. .Iadd.is hydroxyethyl; .Iaddend. R 2 represents a group of formula ##STR2## in which ##STR3## .[.represents an alicyclic amine group having from 4 to 8 ring atoms, optionally having a single double bond, optionally containing an additional hetero-atom and optionally having an oxo group on the ring;.]. .Iadd.is a 3-pyrrolidinyl group; .Iaddend. X represents a hydrogen atom.[.; an alkyl group, an alkoxy group, an alkylthio group, an alkylsulphinyl group, an alkylsulphonyl group, a hydroxy group, a halogen atom or various substituted alkyl groups.].; Y represents .[.a hydrogen atom, an alkyl group, an aliphatic acyl group or an acylimidoyl.]. .Iadd.an acetylimidoyl .Iaddend.group; and R 3 represents a carboxy group or a protected carboxy group.[.].]. and pharmaceutically acceptable salts thereof have valuable antibacterial activity, especially in vivo.

We claim: 
     
       1. Compounds of the formula (I): ##STR65## wherein R 1  is hydroxyethyl, R 2  is ##STR66##  wherein ##STR67##  is a 3-pyrrolidinyl group, X is hydrogen and Y is .[.a group of the formula.]. .Iadd.an acetimidoyl group, ##STR68##.Iaddend.  .[.wherein R 5  and R 6  are the same or different and each is hydrogen or an alkyl group having from 1 to 4 carbon atoms,.].   R 3  is a carboxy group or a protected carboxy group; and   pharmaceutically acceptable salts thereof.   
     
     
       2. The .[.compounds of claim 1, wherein Y is an acetimidoyl group.]. .Iadd.compound of claim 1 which is (5R,6S)-2-(1-acetimidoylpyrrolidin-3-ylthio)-6-[1-(R)-hydroxyethyl]-2-carbapenem-3-carboxylic acid.Iaddend.. 
     
     
       3. The compounds of claim 1, wherein R 3  is a carboxy group. 
     
     
       4. The compounds of claim 1 in the form of the sodium .[.or potassium.]. salt. 
     
     
       5. The compounds of claim .[.2.]. .Iadd.1 .Iaddend.in the form of the .[.sodium or.]. potassium salt. 
     
     
       6. The compound of claim 1 which is 2-(1-acetimidoylpyrrolidin-3-ylthio)-6-(1-hydroxyethyl)-2-carbapenem-3-carboxylic acid. .[.7. The compound of claim 1 which is 2-(1-formimidoylpyrrolidin-3-ylthio)-6-(1-hydroxyethyl)-2-carbapenem-3-car 
     
     
       boxylic acid..]. 8. A pharmaceutical composition comprising an effective amount of an antibacterial agent in admixture with a pharmaceutically acceptable carrier or diluent, wherein the antibacterial agent is selected from compounds of the formula (I): ##STR69## wherein R 1  is hydroxyethyl, R 2  is ##STR70##  wherein ##STR71##  is a 3-pyrrolidinyl group, X is hydrogen and Y is .[.a.]. .Iadd.an acetimidoyl group, .Iaddend.group of the formula ##STR72##  .[.wherein R 5  and R 6  are the same or different and each is hydrogen or an alkyl group having from 1 to 4 carbon atoms,.].   R 3  is a carboxy group or a protected carboxy group; and   
     
     
       pharmaceutically acceptable salts thereof. 9. The composition of claim 8, wherein in said formula Y is an acetimidoyl group.].  .Iadd.said antibacterial agent is (5R,6S)-2-(1-acetimidoylpyrrolidin-3-ylthio)-6-[1-(R)-hydroxyethyl]-2-carb 
     
     
       apenem-3-carboxylic acid.Iaddend.. 10. The composition of claim 8, wherein 
     
     
        R 3  is a carboxy group. 11. The composition of claim 8, wherein said 
     
     
        compound is in the form of the sodium .[.or potassium.]. salt. 12. The composition of claim .[.9.]..Iadd.8.Iaddend., wherein said compound is in 
     
     
        the form of the .[.sodium or.]. potassium salt. 13. The composition of claim 8, wherein said antibacterial agent is 2-(1-acetimidoylpyrrolidin-3-ylthio)-6-(1-hydroxyethyl)-2-carbapenem-3-carboxylic acid. .[.14. The composition of claim 8, wherein said antibacterial agent is 2-(1-formimidoylpyrrolidin-3-ylthio)-6-(1-hydroxyethyl)-2-carbapenem-3-carboxylic acid..].