US 7,247,642 B2 · Antibacterial optically pure benzoquinolizine carboxylic acids, processes, compositions and methods of treatment

Abstract

The present invention relates to optically pure S-(−)-benzoquinolizine carboxylic acids, their derivatives, salts, pseudopolymorphs, polymorphs and hydrates thereof, substantially free of their R-(+)-isomers, to processes for preparation of the optically pure S-(−)-benzoquinolizine carboxylic acids, their derivatives, salts, pseudopolymorphs, polymorphs and hydrates thereof substantially free of their R-(+)-isomers, and to pharmaceutical compositions comprising the S(−)-benzoquinolizine carboxylic acids, their derivatives, salts, pseudopolymorphs, polymorphs and hydrates thereof.

Claims9

Dependent claims

A process for the preparation of S(−)-9-Fluoro-8-(4-hydroxypiperidin-1-yl )-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid.0.2 H2O which comprises the steps of:

a) dissolving S(−)-9-Fluoro-8-(4-hydroxypiperidin-1-yl)-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid in a volume of organic solvent, at an elevated temperature, sufficient to allow crystallization of S-(−)-9-Fluoro-8-(4-hydroxypiperidin-1-yl)-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid 0.2H2O upon addition of water,
b) adding said water in an amount sufficient to bring about crystallization after cooling, and
c) cooling, filtering and drying the separated crystals at temperatures up to 40-50° C. for 3-6 hours, in vacuo upto 50 mm of Hg to a constant weight.

Dependencies are inferred from the claim text.

Facts

Application

09/566,875Filed 8 May 2000 · us provisional application

Priority

WO PCT/IN99/000167 May 1999

Published

US 2003/0207908 A16 Nov 2003

Granted

24 Jul 2007

Term ends

Not estimatedThe source records don’t support an estimate.

Classification13 codes

C07C 279/14
Having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton: being further substituted by carboxyl groups
A61K 31/4745
Ortho- or peri-condensed with heterocyclic ring systems: condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
A61P 31/04
Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics: antibacterial agents
A61P 31/06
Antibacterial agents: for tuberculosis

Antibacterial optically pure benzoquinolizine carboxylic acids, processes, compositions and methods of treatment

Life of this patent

Antibacterial optically pure benzoquinolizine carboxylic acids, processes, compositions and methods of treatment

Life of this patent

Abstract

Claims9