Studles on β-Lactam Antibiotics for Medicinal Purpose. XVIII

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Abstract
7.beta.-[(Z)-2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-substituted methyl-3-cephem-4-carboxylic acids (IIa-l) were prepared by the acylation of 7.beta.-amino-3-substituted methyl-3-cephem-4-carboxylic acids (substituent: phenyl, 1,1-dioxothiadiazinyl, monooxo- or dioxo-diazinyl, triazolyl, tetrazolyl, acetylamino or benzoylamino group) with reactive derivatives of (Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetic acid. IIa-l had a wide antibacterial spectrum against Gram positive and Gram negative bacteria and showed the potent antibacterial activity, being similar to those of cefmenoxime. For the purpose of developing new oral cephalosporin, various esters (IIIa-l, IVa-m, Va-d) of IIa-l were prepared as one form of prodrugs. Urinary recoveries of these esters in mice were measured. Compounds having 5-methyl-2H-tetrazol-2-yl or 5-chloro-1,2,4-triazol-1-yl as a substituent of 3-position and pivaloyloxymethyl or 1-pivaloyloxyethyl as ester group showed high recoveries ranging from 31.2 to 37.3%.