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Mecillinam is a unique penicillin derivative which exhibits strong antimicrobial activities against Escherichia coli and other gram-negative bacilli.1) As it is not absorbed orally,2) its sodium salt is used parenterally and two of its esters, namely pivmecillinam3) and bacmecillinam4) are clinically used as oral prodrugs mainly for urinary tract infections. We have been developing the (5-substituted 2-oxo-1,3-dioxo1-4-yl)methyl group as a new, useful pro-moiety, and the effectiveness of the prodrugs of ampicillie and norfloxacie has been reported recently. As an extension of this prodrug study we prepared some new mecillinam (5-substituted 2-oxo-1,3-dioxol-4-yl)methyl esters and examined their oral absorbabilities. The *present paper describes the preparation and characterization of these mecillinam esters.

Studies on prodrugs. VI Preparation and characterization of (5-substituted 2-oxo-1,3-dioxol-4-yl)methyl esters of mecillinam.