Synthesis and structure-activity relations in the class of 2-(pyridyl)penems.

The isosteric CH----N substitution in the class of 2-arylpenems results in improved antibacterial activity, with retention of the favorable characteristic of stability towards renal dehydropeptidase. High therapeutic efficacy was demonstrated in experimental mice septicemias with the 2-(3-pyridyl) derivative 2b and its orally absorbed acetoxymethyl ester prodrug 4n.

Synthesis and antimicrobial spectrum of FCE 22101 and its orally available ester FCE 22891.

The most efficient routes for the synthesis of FCE 22101, a penem antibiotic characterized by a carbamoyloxymethyl sidechain at C-2 identical to that of cefuroxime and cefotaxime, and of FCE 22891, its orally absorbed pro-drug, are described. On the basis of in-vitro antimicrobial profile and other characteristics the compounds have been considered worthy of further development.