Pfizer Corporation

Barry C Ross

Braham Shroot

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]cephalospo ranic acid. Alternate methods of preparation are provided for these compounds and the principal synthetic route is described in detail.

7[(Furanyl-2-acetamido)-2-acetamido]cephalosporin derivatives

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)-.alpha..sup.3 -cephem-4-carboxylic acid and 7-[D-.alpha.-(cis-2-carboxyoxiran-3-carboxamido)phenylacetamido]cephalospo ranic acid. Alternate methods of preparation are provided for these compounds and the principal synthetic route is described in detail.

Epoxy substituted cephalosporin derivatives

1-N-(.omega.-Amino-2-hydroxyalkyl) derivatives of aminoglycoside antibiotics are prepared by reductive alkylation of the parent antibiotic, or a partially protected derivative thereof, with a 6-dihydroxymethyltetrahydro-1, 3-oxazin-2-one or 5-dihydroxymethyloxazolidin-2-one, followed by hydrolysis, and, if necessary, followed by removal of any remaining protecting groups. The products of the process of this invention are known antibacterial agents.

Process for .omega.-amino-2-hydroxyalkyl derivatives of aminoglycoside

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.

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Birchington, United Kingdom

Barry C Ross