Salts and crystall forms of 2-methyl-2-[4-(3-methyl-2-oxo-8-quinolin-3-yl-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl)-phenyl]-propionitrile

• US 8,436,177 B2
• Filed: 11/16/2007
• Issued: 05/07/2013
• Est. Priority Date: 11/20/2006
• Status: Active Grant

• Current Assignee: Novartis Ag
• Original Assignee: Novartis Ag
• Inventors: Stowasser, Frank, Garad, Sudhakar Devidasrao, Bnziger, Markus
• Primary Examiner(s): DESAI, RITA J
• Application Number:
  US12/514,976
• Publication Number:
  US 20100168153A1
• Time in Patent Office: 1,999 Days
• Field of Search: 546/82, 514/293
• US Class Current: 546/82
• CPC Class Codes: A61P 13/08 of the prostate
• CPC Class Codes: A61P 15/00 Drugs for genital or sexual disorders for disorders of sex hormones A61P5/24; Contraceptives
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 17/06 Antipsoriatics
• CPC Class Codes: A61P 25/00 Drugs for disorders of the nervous system
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61P 35/02 specific for leukemia
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C07C 309/30 of six-membered aromatic rings substituted by alkyl groups
• CPC Class Codes: C07D 471/04 Ortho-condensed systems

Abstract

The invention relates to particular crystalline forms of 2-methyl-2-[4-(3-methyl-2-oxo-8-quinolin-3-yl-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl)-phenyl]-propionitrile, its hydrates and solvates, its salts and hydrates and solvates of its salts, certain processes for their preparation, pharmaceutical compositions containing these crystalline forms, and their use in diagnostic methods or, preferably, for the therapeutic treatment of warm-blooded animals, especially humans, and their use as an intermediate or for the preparation of pharmaceutical preparations for use in diagnostic methods or, preferably, for the therapeutic treatment of warm-blooded animals, especially humans.

Claims

1. A crystalline form of the compound of formula I

2. Compound of formula I according to claim 1 in crystalline form A.

3. A compound according to claim 2 which shows on X-ray diffraction a peak at an angle of diffraction 2Theta of 8.4°

+/−

0.3°

.

4. Compound of formula I according to claim 1 in crystalline form B.

5. A compound according to claim 3 which shows on X-ray diffraction a peak at an angle of diffraction 2Theta of 6.9°

+/−

0.3°

.

6. Compound of formula I according to claim 1 in crystalline form C.

7. A compound according to claim 6 which shows on X-ray diffraction a peak at an angle of diffraction 2Theta of 14.7°

+/−

0.3°

.

8. Compound of formula I according to claim 1 in crystalline form D.

9. A compound according to claim 8 which shows on X-ray diffraction a peak at an angle of diffraction 2Theta of 23.9°

+/−

0.3°

.

10. A monohydrate of compound of formula I according to claim 1 in crystalline form H_A.

11. A compound according to claim 10 which shows on X-ray diffraction a peak at an angle of diffraction 2Theta of 17.6°

+/−

0.3°

.

12. A monotosylate salt of compound of formula I according to claim 1 in crystalline form A.

13. A compound according to claim 12 which shows on X-ray diffraction a peak at an angle of diffraction 2Theta of 5.7°

+/−

0.3°

.

14. A compound according to claim 12 which shows on X-ray diffraction peaks at an angle of diffraction 2Theta of 5.4°

+/−

0.3°

;

5.7°

+/−

0.3° and

17.2°

+/−

0.3°

.

15. A compound according to claim 12 which shows an X-ray diffraction diagram essentially as outlined in FIG. 6.

16. A monotosylate salt of compound of formula I according to claim 1 in crystalline form B.

17. A compound according to claim 16 which shows on X-ray diffraction a peak at an angle of diffraction 2Theta of 5.8°

+/−

0.3°

.

18. A compound according to claim 16 which shows on X-ray diffraction peaks at an angle of diffraction 2Theta of 5.8°

+/−

0.3°

;

17.8°

+/−

0.3° and

18.7°

+/−

0.3°

.

19. A monohydrate of the monotosylate salt of compound of formula I according to claim 1 in crystalline form H_A.

20. A compound according to claim 19 which shows on X-ray diffraction a peak at an angle of diffraction 2Theta of 6.5°

+/−

0.3°

.

21. A dihydrate of the monotosylate salt of compound of formula I according to claim 1 in crystalline form H_B.

22. A compound according to claim 21 which shows on X-ray diffraction a peak at an angle of diffraction 2Theta of 6.9°

+/−

0.3°

.

23. A diformic acid solvate of the monotosylate salt of compound of formula I according to claim 1 in crystalline form S_A.

24. A compound according to claim 23 which shows on X-ray diffraction a peak at an angle of diffraction 2Theta of 5.8°

+/−

0.3°

.

25. A ditosylate salt of compound of formula I according to claim 1 in crystalline form A.

26. A compound according to claim 25 which shows on X-ray diffraction a peak at an angle of diffraction 2Theta of 22.4°

+/−

0.3°

.

27. A trihydrate of the ditosylate salt of compound of formula I according to claim 1 in crystalline form H_A.

28. A compound according to claim 27 which shows on X-ray diffraction a peak at an angle of diffraction 2Theta of 4.7°

+/−

0.3°

.

29. A monohydrate of the diformic acid solvate of the monotosylate salt of compound of formula I according to claim 1 in crystalline form S_C.

30. A compound according to claim 29 which shows on X-ray diffraction a peak at an angle of diffraction 2Theta of 5.6°

+/−

0.3°

.

31. A diacetic acid solvate of the monotosylate salt of compound of formula I according to claim 1 in crystalline form S_B.

32. A compound according to claim 31 which shows on X-ray diffraction a peak at an angle of diffraction 2Theta of 5.7°

+/−

0.3°

.