Studies on beta-lactam antibiotics. III. Syntheses and antibacterial activities of new 3-(1,3-dithiolan-2-yl)cephalosporins, YM-22508, YM-16457 and their prodrug-type esters.

The syntheses and biological activities of new 7-β-[(Z)-2-(2-amino-4-thiazolyl)-2-hydroxy-iminoacetamido]-3-(l, 3-dithiolan-2-yl)-3-cephem-4-carboxylic acid (YM-22508, 1a), 7-β-[(Z)-2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-(1, 3-dithiolan-2-yl)-3-cephem-4-carboxylic acid (YM-16457, 1d) and their prodrug-type esters are described. Among them, YM-22561 (1c), the 1-acetoxyethyl ester of 1a, showed good in vivo efficacy in mice against infections of Staphylococcus aureus Smith, Streptococcus pyogenes S 23 and Escherichia coll NY-17 and a long plasma T1/2 in mice.