Cephem derivatives and process for the preparation thereof

Details Cephem derivatives and process for the preparation thereof Cephem derivatives and process for the preparation thereof

C - Chemistry, Metallurgy

07

D

260/104.1

C07D 501/36 (2006.01) A61K 31/43 (2006.01) A61K 31/545 (2006.01) C07D 213/68 (2006.01) C07D 501/00 (2006.01) C07D 501/02 (2006.01) C07D 501/04 (2006.01) C07D 501/06 (2006.01) C07D 501/20 (2006.01) C07D 501/22 (2006.01) C07D 501/24 (2006.01) C07D 501/26 (2006.01) C07D 501/34 (2006.01) C07D 501/46 (2006.01) C07D 501/56 (2006.01) C07D 501/60 (2006.01)

Patent

CA 1072542

ABSTRACT OF THE DISCLOSURE Cephem derivatives of the formula Image wherein (i) Z is 1,4-dihydro-4-oxo-1-pyridyl or the corresponding group substituted by at least one of alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, OH, F, Cl, Br, I, NO2 or NH2 and R is -S-Het wherein Het is 3-methyl-1,2,4-thiadiazolyl-5, 5-methyl- 1,3,4-oxadiazolyl-2, 5-hydroxymethyl-1,3,4-oxadiazolyl-2, 5- methyl-1,3,4-thiadiazolyl-2, 5-hydroxy-methyl-1,3,4-thiadiazolyl- 2,tetrazolyl-5,1-methyltetrazolyl-5, 1,2,3-triazolyl-4, 4-methyl- oxazolyl-2 or 1-oxidopyridinio-2, or (ii) Z is 3,5-dichloro- 1,4-dihydro-4-oxo-1-pyridyl and R is -OCOCH3 and esters thereof which are readily split, and the physiologically acceptable salts thereof, possess anti-bacterial activity. They can be prepared by reacting a 3-CH2R-7-amino-3-cephem-4-carboxylic acid or a functional derivative thereof with a pyridone acetic acid of the formula Z-CH2-COOH or a functional derivative thereof; or by reacting a 3-CH2R-7-(X-acetamido)-3-cephem-4-carboxylic acid wherein X is Cl, Br or a reactively esterified OH-group, or a functional derivative thereof, with a pyridone of the formula Z-H wherein Z has the values given above, or a functional derivative thereof; or by liberating a functionally modified OH-, HN2- or oxo-group present in a compound otherwise corres- ponding to a product of the above formula by treatment with a solvolyzing or hydrogenolyzing agent.

208630

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