Carbapenem derivatives

C - Chemistry – Metallurgy – 07 – D

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260/271, 260/299

C07D 477/00 (2006.01) C07D 477/20 (2006.01) C07D 519/00 (2006.01)

Patent

CA 2002551

Carbapenem derivatives of formula (I): (see fig. I) wherein (a) R1 is a hydrogen atom, an alkyl group of from 1 to 6 carbon atomsr a hydroxy-lower alkyl group or a protected hydroxy-lower alkyl group of from 1 to 6 carbon atoms in its alkyl moiety, (b) COOR2 is a carboxyl group, a carboxylate anion or a protected carboxyl group, (c) R3 is an alkyl group of from 1 to 6 carbon atoms and (d) R4 is a substituted or unsubstituted heterobicyclic group of formula (II): (see fig. II) in which the partial structure (see fig. III) is a 5- or 6-membered, saturated or unsaturated, nitrogen-containing heterocycle containing 1 to 4 hetero atoms each selected from the group consisting of oxygen, sulfur and nitrogen, at least one hetero atom being nitrogen, and is which R5 and R6 each is a hydrogen atom or an appropriate substituent, any isomeric form thereof, and pharmacologically acceptable salts thereof are potent and stable antimicrobial agents.

Dérivés de carbapénème de formule I (voir fig. I), où : a) R1 est un atome d'hydrogène, un groupe alkyle de 1 à 6 atomes de carbone, un groupe hydroxy-alkyle inférieur ou un groupe hydroxy-alkyle inférieur protégé de 1 à 6 atomes de carbone dans la fraction alkyle; b) COOR2 est un groupe carboxyle, un anion carboxylate ou un groupe carboxyle protégé; c) R3 est un groupe alkyle de 1 à 6 atomes de carbone; d) R4 est un groupe hétérobicyclique, avec ou sans substitution, de formule II (voir fig. II), dont la structure partielle (voir fig. III) est un hétérocycle azoté de 5 ou 6 chaînons, saturé ou non, renfermant 1 à 4 hétéroatomes, choisis chacun parmi un oxygène, un soufre et un azote, au moins un hétéroatome étant de l'azote; R5 et R6 sont chacun un atome d'hydrogène ou un substituant approprié. Toute forme isomère de ces dérivés et leurs sels pharmacocompatibles sont des agents antimicrobiens stables et puissants.

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