Cephalosporin derivatives

Abstract

Cephemcarboxylic acid esters of the general formula <IMAGE> +TR <IMAGE> pharmaceutical preparations which are active against bacterial infections, which contain such cephem derivatives, a process for the preparation of the cephem derivatives and the pharmaceutical preparations, and also the use of the cephem derivatives for combating bacterial infections.

We claim: 
     
       1. .[.A cephemcarboxylic acid ester of the formula I ##STR30## in which m denotes 0 or 1, R 1  denotes hydrogen or methyl and   R 2  denotes C 1  -C 6  -alkyl, C 2  -C 6  -alkenyl, C 2  -C 6  -alkynyl or the group   --(CH.sub.2).sub.n --OR.sup.3        in which n stands for 0 or 1 and R 3  has the meaning of C 1  -C 6  -alkyl, which can also be further substituted by phenyl, or of C 3  -C 4  -alkenyl, in which the HO group is in the syn-position and, if m is 0 and R 1  is hydrogen, R 2  cannot be methyl physiologically tolerated acid addition salts thereof or their diastereomers.]. .Iadd.A compound consisting essentially of pure diastereomer I of α-(2,2-dimethyl-propionyloxy)-ethyl 7-[2-(2-aminothiazol-4-yl)-2-(Z)-hydroxyimino-acetamido]-3-(methoxymethyl)-3-cephem-4-carboxylate or a physiologically tolerated acid addition salt thereof.Iaddend.. .[.     
     
     
       2.  A cephemcarboxylic acid ester as claimed in claim 1, in which R 1  and the meaning given there and R 2  stands for C 1  -C 4  -alkyl, C 2  -C 4  -alkenyl, C 3  -C 4  -alkynyl or the group   --(CH.sub.2).sub.n --OR.sup.3     in which n is 0 or 1 and R 3  has the meaning of C 1  -C 4  -alkyl, which can also be further substituted by phenyl, or of C 3  -C 4  -alkenyl..]. .[.3. 2,2-Dimethyl-butanoyl-oxymethyl 7-[2-(2-aminothiazol-4-yl)-2-(Z)-hydroxyimino-acetamido]-3-(methoxymethyl)   
     
     
       -3-cephem-4-carboxylate..]. .[.4.  2,2-Dimethyl-3-butenoyl-oxymethyl 7-[2-(2-aminothiazol-4-yl)-2-(Z)-hydroxyimino-acetamido]-3-(methoxymethyl)-3-cephem-4-carboxylate..]. .[.5. α-(2,2-Dimethyl-butanoyloxy)-ethyl 7-[2-(2-aminothiazol-4-yl)-2-(Z)-hydroxyimino-acetamido]-3-(methoxymethyl)-3-cephem-4-carboxylate..]. .[.6. α-(2,2-Dimethyl-propionyloxy)-ethyl 7-[2-(2-aminothiazol-4-yl)-2-(Z)-hydroxyimino-acetamido-9-3-(methoxymethyl 
     
     
       )-3-cephem-4-carboxylate and its diastereomers..]. 7. A pharmaceutical formulation which is active against bacterial infections, .[.which contains a cephemcarboxylic acid ester of the formula I as claimed in claim 1 together with a pharmaceutically acceptable carrier.]. .Iadd.comprising a pharmaceutically acceptable carrier and a compound consisting of essentially of pure diastereomer I of α-(2,2-dimethylpropionyloxy)-ethyl 7-[2-(2-aminothiazol-4-yl)-2-(Z)-hydroxyimino-acetamido]-3-(methoxymethyl)-3-cephem-4-carboxylate or a physiologically tolerated acid addition salt 
     
     
        thereof.Iaddend.. 8. A method of combating bacterial infections which comprises administering .Iadd.to an animal host in recognized need thereof .Iaddend.an effective amount of .[.a cephemcarboxylic acid ester of the formula I as claimed in claim 1.]. .Iadd.a compound consisting essentially of pure diastereomer I of α-(2,2-dimethyl-propionyloxy)-ethyl 7-[2-(2-aminothiazol-4-yl)-2-(Z)-hydroxyimino-acetamido]-3-(methoxymethyl)-3-cephem-4-carboxylate or a physiologically tolerated acid addition salt thereof.Iaddend.. .[.9. A cephemcarboxylic acid as claimed in claim 1, in which m denotes O, R 1  denotes hydrogen or methyl and R 2  denotes C 1  -C 4  alkyl..]. .[.10. A cephemcarboxylic acid as claimed in claim 1, in which m denotes O, R 1  denotes hydrogen or methyl and R 2  denotes methyl or ethyl..]. .[.11. A cephemcarboxylic acid as claimed in claim 1, in which m denotes O, R 1  methyl and R 2  denotes methyl..].