Process for the preparation of gemifloxacin
OwnerChandrasekaran Ramasubbu, Suresh Ramasamy +2inventors
InventorsChandrasekaran Ramasubbu, Suresh Ramasamy, Kiranmye Tayyala, Mahender Rao Siripragada
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Abstract
The present invention relates to an improved process for the preparation of Gemifloxacin mesylate of formula (V). The present invention further provides novel intermediates of formula (II) and (IV), which are useful intermediates for the preparation of Gemifloxacin mesylate of formula (V). wherein R1 is linear or branched chain alkyl group having 1-3 carbon atoms.
Claims14
A process for the preparation of Gemifloxacin mesylate of formula (V), which comprises the steps of:
- protecting the amino group of a compound of formula (I) or salts thereof by reacting compound A in an organic solvent or aqueous organic solvent in the presence of an organic base to get an intermediate of formula (II);
- wherein R1 is hydrogen or linear or branched chain alkyl group having 1-3 carbon atoms.
- (ii) condensing the intermediate of formula (II) with a compound of formula (III) to get an intermediate of formula (IV);
- (iii) purifying the intermediate of formula (IV) and;
- (iv) deprotecting the intermediate of formula (IV) using methanesulfonic acid in an organic solvent or aqueous organic solvent to produce the Gemifloxacin mesylate of formula (V).
An intermediate represented by the following formula (II),
- wherein R1 is hydrogen or linear or branched chain alkyl group having 1-3 carbon atoms.
An intermediate represented by the following formula (IV), for preparing Gemifloxacin mesylate of compound formula (V):
- wherein R1 is hydrogen or linear or branched chain alkyl group having 1-3 carbon atoms.
A crystalline solid intermediate 6-Fluoro-7-[3-({[(1Z)-3-ethoxy-1-methyl-3-oxoprop-1-en-1-yl]amino}methyl)-4 (methoxyimino)-pyrrolidin-1-yl]-1-cyclopropyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid, characterized by an x-ray powder diffraction pattern expressed in terms of 2θ at about 3.42, 7.06, 7.56, 8.16, 9.38, 10.36, 12.06, 14.26, 14.94, 15.50, 16.08, 18.54, 19.15, 20.05, 21.68, 22.90, 24.76, 26.42, 27.04, 28.33, 31.78, 37.84, 43.98.
An anhydrate form of Gemifloxacin mesylate (Form A) characterized by an x-ray powder diffraction pattern expressed in terms of 2θ at about 4.23, 12.66, 13.92, 16.90, 17.90, 19.28, 24.78, 26.22.
Dependencies are inferred from the claim text.