Carbapenem antibacterials with gram-negative activity and processes for their preparation
AssigneeFOB Synthesis, Inc.
InventorsWoo-Baeg Choi, Ewa Kowalik
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Abstract
The present invention provides β-methyl carbapenem compounds and pharmaceutical compositions useful in the treatment of bacterial infections and methods for treating such infections using such compounds and/or compositions. The invention includes administering an effective amount of a carbapenem compound or salt and/or prodrug thereof to a host in need of such a treatment. The present invention is also in the field of synthetic organic chemistry and is specifically provides an improved method of synthesis of β-methyl carbapenems which are useful as antibacterial agents.
Claims4
A process for preparing a β-methyl carbapenem analog comprising:
- (a) preparing or obtaining a carbapenem intermediate of the structure (A)
- wherein
- P is H, hydroxy, or hydroxyl protected by a hydroxyl protecting group;
- R is H or alkyl;
- R1 is H or alkyl;
- P′ is a suitable carboxyl protecting group;
- and
- R′ is an alkyl or substituted alkyl;
- (b) coupling the compound of structure (A) with an amine, in the presence of Pd2(dba)3CHCl3 (tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct) and a compound selected from 1,4-bis(diphenylphosphine)butane or triethylphosphate, to obtain a β-methyl carbapenem analog;
- and
- (c) optionally deprotecting the β-methyl carbapenem analog;
- wherein the amine is selected from the group consisting from:
Dependencies are inferred from the claim text.