SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIPS OF A NEW SERIES OF CEPHALOSPORINS, BMY-28142 AND RELATED COMPOUNDS

Abstract

The synthesis of a series of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-oxyiminoacetamido]-3-ammoniomethyl-3-cephems is described. Variations of an oxyimino moiety in the 7-side chain and a quaternary ammonium moiety in the 3-side chain were examined and structure-activity relationships studied. BMY-28142, the 3-(Nmethylpyrrolidinio)methyl derivative of the 7-α-methoxyimino series of cephalosporins, exhibited broad antimicrobial activity against both Gram-positive and Gram-negative bacteria including Pseudomonas aeruginosa.