Carbapenem and Penem Antibiotics. VII. Synthesis and Antibacterial Activity of 1β-Methyl-2-(Quaternary Heteroaromatic-thiomethyl) Carbapenems

The synthesis and antibacterial activity of a series of 1β-methylcarbapenems having quaternary heteroaromatic-thiomethyl groups at the C-2 position are described. Both 2-hydroxymethyl and 2-chloromethyl carbapenems (1 and 7) respectively served as the common key intermediates for the preparation of these compounds. Of these, the 4-pyridiniothiomethyl derivatives exhibited the best antibacterial properties and turned out to possess high in vivo efficacy as well.