7[(Carboxyoxiran-3-carboxamido)phenylacetamido]cephalosporin derivatives
AssigneePfizer Inc.
InventorsBarry Clive Ross, Braham Shroot
Life of this patent
Estimating the term…
Abstract
A series of novel 7-(D-.alpha.-acylaminoarylacetamido)-.DELTA..sup.3 -cephem derivatives have been prepared wherein the acyl moiety contains an epoxy group immediately adjacent to the carbonyl carbon atom. These compounds are useful as antibacterial agents for the treatment of diseases caused by Gram-negative and Gram-positive bacteria. Preferred members include 7-[D-.alpha.-(cis-2-carboxyoxiran-3-carboxamido)phenylacetamido]-3-(1-meth yl-1,2,3,4-tetrazol-5-ylthiomethyl)-.DELTA..sup.3 -cephem-4-carboxylic acid and 7-[D.alpha.-(cis-2-carboxyoxiran-3-carboxamido)phenylacetamido]cephalospor anic acid. Alternate methods of preparation are provided for these compounds and the principal synthetic route is described in detail.
Claims10
A compound of the formula:
- ##STR14## and the pharmaceutically acceptable base salts thereof, wherein R.sup.1 is a member selected from the group consisting of phenyl, thienyl and 2-furyl, and mono substituted phenyl wherein the substituent is chosen from the group consisting of halogen, hydroxy, lower alkyl, lower alkoxy and trifluoromethyl;
- R is hydroxy, and R.sup.2 is a member selected from the group consisting of pyrimidin-2-ylthio, 4,6-dimethylpyrimidin-2-ylthio, 4,5-dimethylthiazol-2-ylthio, 1,3,5-triazin-2-ylthio, 2-methyl-1,3,4-thiadiazol-5-ylthio, 2-methyl-1,3,4-oxadiazol-5-ylthio and 1-substituted-1,2,3,4-tetrazol-5-ylthio wherein the 1-substituent is chosen from the group consisting of lower alkyl, benzyl, phenyl, chlorophenyl and anisyl;
- R.sup.3 is a member selected from the group consisting of carboxy, COOR.sup.6 wherein R.sup.6 is chosen from the group consisting of lower alkyl, 5-indanyl, naphthyl, phenyl and mono substituted phenyl wherein the substituent is chosen from the group consisting of halogen, lower alkyl, lower alkoxy and trifluoromethyl, and CONR.sup.7 R.sup.8 wherein R.sup.7 and R.sup.8 are each chosen from the group consisting of hydrogen, lower alkyl and cycloalkyl having from three to six carbon atoms;
- R.sup.4 and R.sup.5 are each a member selected from the group consisting of hydrogen and lower alkyl, and X is a direct carbon-carbon link.
7-[D-.alpha.-(cis-2-Carboxyoxiran -3-carboxamido)phenylacetamido]-3-(1-methyl-1,2,3,4-tetrazol-5-ylthiomethyl )-.DELTA..sup.3 -cephem-4-carboxylic acid.
Dependencies are inferred from the claim text.