Salts of lorcaserin with optically active acids

Patent metadata

Field	Value
Publication number	US-9248133-B2
Application number	US-201113820126-A
Country	US
Kind code	B2
Filing date	Aug 31, 2011
Priority date	Sep 1, 2010
Publication date	Feb 2, 2016
Grant date	Feb 2, 2016

Abstract

Salts of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine with optically active acids, and pharmaceutical compositions comprising them that are useful for, inter alia, weight management.

First claim

The invention claimed is:

1. A salt selected from:
(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (1 S)-(+)-10-camsylate salt;
(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hemi-L-malate salt;
(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine L-glutamate salt;
(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine L-aspartate salt;
(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hemimucate salt;
(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine pyroglutamate salt; and
(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine glucuronate salt;
and pharmaceutically acceptable solvates and hydrates thereof.

2. The salt according to claim 1 , that is (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (1S)-(+)-10-camsylate salt.

3. The salt according to claim 2 , having an X-ray powder diffraction pattern comprising peaks, in terms of 2θ, at about 18.25°, about 16.45°, and about 18.57°.

4. The salt according to claim 2 , having an X-ray powder diffraction pattern substantially as shown in FIG. 1 .

5. The salt according to claim 1 , that is (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hemi-L-malate salt.

6. The salt according to claim 5 , having an X-ray powder diffraction pattern comprising peaks, in terms of 2θ, at about 10.84°, about 11.7932°, and about 21.97°.

7. The salt according to claim 5 , having an X-ray powder diffraction pattern substantially as shown in FIG. 4 .

8. The salt according to claim 1 , that is (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine L-glutamate salt.

9. The salt according to claim 8 , having an X-ray powder diffraction pattern comprising peaks, in terms of 2θ, at about 25.59°, about 17.63°, and about 21.78°.

10. The salt according to claim 8 , having an X-ray powder diffraction pattern substantially as shown in FIG. 7 .

11. The salt according to claim 1 , that is (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine L-aspartate salt.

12. The salt according to claim 11 , having an X-ray powder diffraction pattern comprising peaks, in terms of 2θ, at about 21.22°, about 8.49°, and about 13.40°.

13. The salt according to claim 11 , having an X-ray powder diffraction pattern substantially as shown in FIG. 10 .

14. The salt according to claim 1 , that is (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hemimucate salt.

15. The salt according to claim 14 , having an X-ray powder diffraction pattern comprising a peak, in terms of 2θ, at about 5.06°, about 18.60°, and about 20.92°.

16. The salt according to claim 14 , having an X-ray powder diffraction pattern substantially as shown in FIG. 13 .

17. The salt according to claim 1 , that is (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine glucuronate salt.

18. The salt according to claim 17 , having an X-ray powder diffraction pattern comprising peaks, in terms of 2θ, at about 16.46°, about 5.59°, and about 18.40°.

19. The salt according to claim 17 , having an X-ray powder diffraction pattern substantially as shown in FIG. 16 .

20. The salt according to claim 1 , that is (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine pyroglutamate salt.

21. The salt according to claim 20 , having an X-ray powder diffraction pattern comprising peaks, in terms of 2θ, at about 6.78°, about 18.80°, and about 16.95°.

22. The salt according to claim 20 , having an X-ray powder diffraction pattern substantially as shown in FIG. 19 .

23. A pharmaceutical composition comprising a salt according to claim 1 and a pharmaceutically acceptable carrier.

24. A process for preparing a pharmaceutical composition comprising admixing a salt according to claim 1 and a pharmaceutically acceptable carrier.

Assignees

• Blackburn Anthony C
• Betts Iii William Lucas
• Rueter Jaimie Karyn
• Shan Yun
• Shifrina Anna
• Stirn Scott
• Arena Pharm Inc

Inventors

• Blackburn Anthony C
• Betts Iii William Lucas
• Rueter Jaimie Karyn
• Shan Yun
• Shifrina Anna
• Stirn Scott

Classifications

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• C07D223/16 Primary

  Benzazepines; Hydrogenated benzazepines · CPC title

• A61K45/06

  Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca · CPC title

• A61P3/04

  Anorexiants; Antiobesity agents · CPC title

• A61K31/55 Primary

  having seven-membered rings, e.g. azelastine, pentylenetetrazole · CPC title