EP0367124A1 — Penicillanic acid derivatives

USPTO Abstract

The compounds of the general formula in which R is hydrogen, a readily hydrolyzable ester group or a protecting group, R¹ is hydrogen and R² is hydrogen or an acyl group, or R¹ and R² taken together are the group in which n is 5, 6 or 7, X is fluoro, thiocyanato, azido or the group R 3a CO₂- R 3a is C₂- to C₁₆-alkyl, aryl, a heterocycle, -(CH₂) m -aryl, -(CH₂) m -heterocycle, a heterocycle-lower alkenyl or aryl-lower alkenyl, R³ is C₁- to C₁₆-alkyl, aryl, a heterocycle, -(CH₂) m -aryl, a -(CH₂) m -heterocycle, a heterocycle-lower alkenyl or aryl-lower alkenyl, R⁴ and R 4′ independently are hydrogen, lower alkyl, lower alkenyl or lower alkynyl, R a is hydrogen, halogen, amino, amino-lower alkyl, carboxy, carbamoyl, carboxy-lower alkyl, carbamoyl-lower alkyl or lower carbalkoxy-lower alkyl, m is from 1 to 4 and p is 3, 4 or 5, provided that X is other than fluoro when R is a protecting group, a hydrate, a readily hydrolyzable ester or salt thereof, or a hydrate of the ester or the salt, when R is hydrogen are useful as anti-bacterial agents for the prevention and treatment of bacterial infections in mammals, including humans.