1,3-dithietane-2-carboxylic acid penicillin and cephalosporin derivatives

Abstract

Substituted 1,3-dithietane-2-carboxylic acid derivatives useful as intermediates for the preparation of highly effective penicillin and cephalosporin derivatives and the preparation thereof.

What is claimed is: .[.1. 7-substituted cephalosporin or penicillin derivatives represented by the formula ##STR79## wherein R 1  is a carboxyl group or the functional derivative residue thereof selected from the group consisting of carboxylic acid lower alkyl ester residue, carboxylic acid aralkyl ester residue, a carbamoyl group, N-monoalkylcarbamoyl group, N,N-dialkylcarbamoyl group, a carboazoyl group, and a cyano group; R 2  is a carboxyl group or the functional derivative residue thereof selected from the group consisting of carboxylic acid lower alkyl ester residue, carboxylic acid aralkyl ester residue, a carbamoyl group, N-monoalkylcarbamoyl group, N,N-dialkylcarbamoyl group, a carboazoyl group, and a cyano group, a hydrogen atom, a lower alkyl group, a lower hydroxyalkyl group, a lower alkoxyalkyl group, a lower carboxyalkyl group, a lower arylalkyl group, a lower alkoxy group, a lower alkanoyl group, R 4  S(O) n  group wherein R 4  represents a lower alkyl group and n represents 0, 1 or 2, and aryl group which may have a substituted selected from the group consisting of hydroxyl and alkoxy groups, an aroyl group, a lower alkenyl group, a sulfamoyl group, or a heterocyclic residue which may have a substituent selected from the group consisting of a hydroxyl group, methyl group, and alkylthio group; and wherein  ○Ce  and  ○Pe represent a cephalosporin nucleus and a penicillin nucleus, 
     
        respectively..]. .Iadd.2.  6-substituted penicillin derivative represented by the formula ##STR80## wherein R 1  is a carboxyl group or the functional derivative residue thereof selected from the group consisting of carboxylic acid lower alkyl ester residue, carboxylic acid aralkyl ester residue, a carbamoyl group, N-monoalkylcarbamoyl group, N,N-dialkylcarbamoyl group, a carboazoyl group, and a cyano group; R 2  is a carboxyl group or the functional derivative residue thereof selected from the group consisting of carboxylic acid lower alkyl ester residue, carboxylic acid aralkyl ester residue, a carbamoyl group, N-monoalkylcarbamoyl group, N,N-dialkylcarbamoyl group, a carboazoyl group, and a cyano group, a hydrogen atom, a lower alkyl group, a lower hydroxyalkyl group, a lower alkoxyalkyl group, a lower carboxyalkyl group, a lower aralkyl group, a lower alkoxy group, a lower alkanoyl group, R 4  S(O) n  group wherein R 4  represents a lower alkyl group and n represents 0, 1 or 2, and aryl group which may have a substituent selected from the group consisting of hydroxyl and alkoxy groups, an aroyl group, a lower alkenyl group, a sulfamoyl group, or a heterocyclic residue which may have a substituent selected from the group consisting of a hydroxyl group, methyl group, and alkylthio group; and wherein  ○Pe  represents a 
     
     
        penicillin nucleus. .Iaddend. .Iadd.3.  The 6-substituted penicillin derivative of claim 2 wherein R 1  and R 2  are each a carboxyl group. .Iaddend. .Iadd.4. The 6-substituted penicillin derivative of claim 2 wherein R 1  is a carboxyl group and R 2  is a lower alkylthio group. .Iaddend. .Iadd.5. The 6-substituted penicillin derivative of claim 2 wherein R 1  is a carboxyl group and R 2  is a lower alkoxy group. .Iaddend. .Iadd.6. The 6-substituted penicillin derivative of claim 2 wherein R 1  is a carboxyl group and R 2  is a lower alkyl group. .Iaddend. .Iadd.7. The 6-substituted penicillin derivative of claim 2 wherein R 1  is a carboxyl group and R 2  is hydrogen. .Iaddend. .Iadd.8. 7-substituted cephalosporin derivative represented by the formula ##STR81## wherein R 1  is an N-monoalkylcarbamoyl group or an N,N-dialkylcarbamoyl group; R 2  is a carboxyl group or the functional derivative residue thereof selected from the group consisting of carboxylic acid lower alkyl ester residue, carboxylic acid aralkyl ester residue, a carbamoyl group, N-monoalkylcarbamoyl group, N,N-dialkylcarbamoyl group, a carboazoyl group, and a cyano group, a hydrogen atom, a lower alkyl group, a lower hydroxyalkyl group, a lower alkoxyalkyl group, a lower carboxyalkyl group, a lower arylalkyl group, a lower alkoxy group, a lower alkanoyl group, R 4  S(O) n  group wherein R 4  represents a lower alkyl group and n represents 0, 1 or 2, and aryl group which may have a substituent selected from the group consisting of hydroxyl and alkoxy groups, an aroyl group, a lower alkenyl group, a sulfamoyl group, or a heterocyclic residue which may have a substituent selected from the group consisting of a hydroxyl group, methyl group, and alkylthio group; and wherein  ○Ce  represents a cephalosporin nucleus. .Iaddend.