Carbapenem derivatives having antibiotic activity, their...

C - Chemistry – Metallurgy – 07 – D

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C07D 477/00 (2006.01) A61K 31/40 (2006.01) A61K 31/495 (2006.01) A61K 31/55 (2006.01) C07D 477/20 (2006.01)

Patent

CA 2036941

ABSTRACT OF THE DISCLOSURE Carbapenem compounds of formula (I): Image (I) [in which: A is a fully saturated heterocyclic group, of which at least one ring atom is nitrogen; R1 is hydrogen or methyl; R2 is hydrogen or alkyl; R3 is hydrogen or a negative ion; Q is: (i) -B-N+R8R9R10, where R8, R9 and R10 are alkenyl, alkynyl or optionally substituted alkyl, and B is alkylene or alkylidene; (ii) a heterocyclic group of which one ring atom is a >N+R11R12, where R11 and R12 are alkenyl, alkynyl or optionally substituted alkyl; (iii) alkyl substituted by a heterocyclic group as defined in (ii) above; or (iv) alkyl substituted by an aromatic heterocyclic group, of which one ring atom is Image or R2 and Q, and the nitrogen to which they are attached, form a group of formula (II): Image (II) where m and n are 1, 2 or 3; R6 is optionally substituted alkyl; and R7 is alkenyl, alkynyl or optionally substituted alkyl] and pharmaceutically acceptable salts and esters thereof have valuable antibacterial activity with enhanced resistance to dehydropeptidase I and .beta.-lactamase. Methods of preparing and using the compounds are also provided.

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