IP Library › Granted Patent US 8,039,485
Granted Patent B2
US 8,039,485 · App. 11/728,343 · Granted Oct 18, 2011

Malate salts, and polymorphs of (3S,5S)-7-[3-amino-5-methyl-piperidinyl]-1-cyclopropyl-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 8,039,485
App. No.
11/728,343
Granted
Oct 18, 2011
Kind
B2
Abstract

The present invention is directed to malate salts of (3S,5S)-7-[3-amino-5-methyl-piperidinyl]-1-cyclopropyl-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid, and its polymorphs. The present invention is also directed to pharmaceutical compositions comprising the described salts and polymorphs.

Claims (17)

1. A D,L-malate hemi-hydrate salt of (3S,5S)-7-[3-amino-5-methyl-piperidinyl]-1-cyclopropyl-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid.

2. The D,L-malate hemi-hydrate salt according to claim 1 , having an X-ray diffraction pattern substantially in accordance with the pattern of FIG. 1 .

3. The D,L-malate hemi-hydrate salt according to claim 1 , having a solid-state 13 C NMR spectrum substantially in accordance with the pattern of FIG. 4 .

4. The D,L-malate hemi-hydrate salt according to claim 1 , having an infrared spectrum pattern substantially in accordance with the pattern of FIG. 9 .

5. The D,L-malate hemi-hydrate salt according to claim 2 , having characteristic X-ray diffraction peaks at about 10.7, about 11.98 and about 12.5 degrees 2 theta.

6. A D-malate hydrate salt of (3S,5S)-7-[3-amino-5-methyl-piperidinyl]-1-cyclopropyl-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid having an X-ray diffraction pattern substantially in accordance with the pattern of FIG. 2 .

7. An L-malate hydrate salt of (3S,5S)-7-[3-amino-5-methyl-piperidinyl]-1-cyclopropyl-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid having an X-ray diffraction pattern substantially in accordance with the pattern of FIG. 3 .

8. A D-malate anhydrate salt of (3S,5S)-7-[3-amino-5-methyl-piperidinyl]-1-cyclopropyl-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid having a solid-state 13 C NMR spectrum substantially in accordance with the pattern of FIG. 7 .

9. An L-malate anhydrate salt of (3S,5S)-7-[3-amino-5-methyl-piperidinyl]-1-cyclopropyl-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid having a solid-state 13 C NMR spectrum substantially in accordance with the pattern of FIG. 8 .

10. The D-malate hydrate salt according to claim 6 , having a solid-state 13 C NMR spectrum substantially in accordance with the pattern of FIG. 5 .

11. The D-malate hydrate salt according to claim 6 , having an infrared spectrum pattern substantially in accordance with the pattern of FIG. 10 .

12. The D-malate hydrate salt according to claim 6 , having characteristic X-ray diffraction peaks at about 9.3, about 12.1 and about 22.6 degrees 2 theta.

13. The L-malate hydrate salt according to claim 7 , having a solid-state 13 C NMR spectrum substantially in accordance with the pattern of FIG. 6 .

14. The L-malate hydrate salt according to claim 7 , having an infrared spectrum pattern substantially in accordance with the pattern of FIG. 11 .

15. The L-malate hydrate salt according to claim 7 , having characteristic X-ray diffraction peaks at about 9.5, about 11.7 and about 12.3 degrees 2 theta.

16. The D-malate anhydrate salt according to claim 8 , having an infrared spectrum pattern substantially in accordance with the pattern of FIG. 12 .

17. The L-malate anhydrate salt according to claim 9 , having an infrared spectrum pattern substantially in accordance with the pattern of FIG. 13 .