Chiral fluoroquinolone arginine salt forms
AssigneeWockhardt Limited
InventorsNoel J. De Souza, Shivkumar Agarwal, Mahesh V. Patel, Satish B. Bhawsar, Rupinder K. Beri, Ravindra D. Yeole, Nitin Shetty
Life of this patent
Estimating the term…
Abstract
The invention relates to the new arginine salt forms of S-(−)-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid, a process for their preparation and pharmaceutical formulations which comprise those arginine salt forms as the active ingredient for its use in treating antimicrobial infections.
Claims55
S-(−)-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid arginine salt of the formula I,
- 3
- wherein x is 0, 0.25, 0.50, 0.75, or 1.0, in either a substantially crystalline form or a substantially amorphous form.
A S-(−)-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid arginine salt having the following X-ray powder diffraction data:
- (2θ):
- 10.16, 11,78, 12.52, 16.00, 18.94, 19.66, 20.36, 21.28, 21.92, 22.52, 24.74, 25.28, 30.74.
A S-(−)-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid arginine salt having the following X-ray powder diffraction data:
- (2θ):
- 10.16, 11,78, 12.52, 16.00, 18.94, 19.66, 20.36, 21.28, 21.92, 22.52, 24.74, 25.28, 30.74;
- a DSC exotherm at 242.18° C. (onset at 207.85° C.) and a water content of between 0.1 and 0.2% by weight as determined by titration according to Karl Fischer.
The S-(−)-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid arginine salt having the following X-ray powder diffraction data:
- (2θ):
- 18.28, 18.8, 19.8, 20.12, 20.62, 21.10, 21.44, 21.88, 22.6, 23.02.
The S-(−)-9-fluoro-6,7-dihydro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid arginine salt having the following X-ray powder diffraction data:
- (2θ):
- 1 8.28, 18.8, 19.8, 20.12, 20.62, 21.10, 21.44, 21.88, 22.6, 23.02;
- having a DSC endotherm at 194.60° C. (onset at 185.28° C.) and an exotherm at 245.81° C. (onset at 226.23° C.), and a water content of between 0.4 and 0.7% by weight as determined by titration according to Karl Fischer.
Dependencies are inferred from the claim text.