Crystalline salts of thieno[3,2-c]pyridine kinase inhibitors with improved cpy safety profile

1. The compound N-(4-{4-amino-7-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]thieno[3,2-c]pyridin-3-yl}phenyl)-N′-(3-fluorophenyl)urea malonate in a solid crystalline form, wherein the crystalline form is Form I, characterized at least by a powder X-ray diffraction peak at each of the following positions: 6.14, 10.70, 19.54, 21.22, 23.14, 24.00° 2θ, ±0.2° 2θ.

2. The compound of claim 1 , wherein the crystalline form is Form I, characterized at least by a powder X-ray diffraction peak at each of said positions: 6.14, 9.36, 10.70, 11.68, 12.28, 13.30, 16.32, 16.54, 16.97, 18.47, 19.54, 21.22, 21.50, 23.14, 23.46, 23.68, 24.00° 2θ, ±0.2° 2θ.

3. The compound of claim 1 , wherein the crystalline form is a tetrahydrate.

4. The compound N-(4-{4-amino-7-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]thieno[3,2-c]pyridin-3-yl}phenyl)-N′-(3-fluorophenyl)urea L-tartrate in a solid crystalline form, wherein the crystalline form is Form II, characterized at least by a powder X-ray diffraction peak at each of the following positions: 6.21, 8.88, 10.28, 10.64, 19.18, 20.58, 21.16, 21.38, 21.75, 22.50, 22.86, 23.86, 24.50, 24.92°, 2θ±0.2° 2θ.

5. The compound of claim 4 , wherein the crystalline form is Form II, characterized at least by a powder X-ray diffraction peak at each of said positions: 6.21, 8.88, 10.28, 10.64, 11.96, 12.44, 12.76, 15.93, 18.48, 19.18, 20.58, 21.16, 21.38, 21.75, 22.50, 22.86, 23.86, 24.50, 24.92° 2θ, ±0.2° 2θ.

6. The compound of claim 4 , wherein the crystalline form is a tetrahydrate.

7. The compound N-(4-{4-amino-7-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]thieno[3,2-c]pyridin-3-yl}phenyl)-N′-(3-fluorophenyl)urea HCl in a solid crystalline form wherein the crystalline form is Form III, characterized at least by a powder X-ray diffraction peak at each of the following positions: 5.80, 8.00, 9.71, 13.63, 16.66, 18.69, 19.49, 22.35° 2θ, ±0.2° 2θ.

8. The compound of claim 7 , wherein the crystalline form is Form III, characterized at least by a powder X-ray diffraction peak at each of said positions: 5.80, 6.36, 8.00, 9.71, 10.22, 13.63, 16.66, 18.69, 19.49, 19.77, 21.59, 22.35, 22.76° 2θ, ±0.2° 2θ.

9. The compound of claim 7 , wherein the crystalline form is an anhydrate.

10. The compound N-(4-{4-amino-7-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]thieno[3,2-c]pyridin-3-yl}phenyl)-N′-(3-fluorophenyl)urea mesylate in a solid crystalline form, wherein the crystalline form is Form IV, characterized at least by a powder X-ray diffraction peak at each of the following positions: 5.37, 7.40, 10.69, 18.39, 18.78, 20.42, 21.20° 2θ±0.2° 2θ.

11. The compound of claim 10 , wherein the crystalline form is Form IV, characterized at least by a powder X-ray diffraction peak at each of said positions: 5.37, 7.40, 10.69, 11.92, 14.31, 16.04, 18.02, 18.39, 18.78, 20.42, 21.20° 2θ, ±0.2° 2θ.

12. The compound of claim 10 , wherein the crystalline form is an anhydrate.

13. The compound N-(4-{4-amino-7-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]thieno[3,2-c]pyridin-3-yl}phenyl)-N′-(3-fluorophenyl)urea L-bitartrate in a solid crystalline form, wherein the crystalline form is Form V, characterized at least by a powder X-ray diffraction peak at each of the following positions: 3.04, 3.80, 7.62, 16.12, 23.58° 2θ, ±0.2° 2θ.

14. The compound of claim 13 , wherein the crystalline form is Form V, characterized at least by a powder X-ray diffraction peak at each of said positions: 2.70, 3.04, 3.80, 5.64, 6.58, 7.62, 16.12, 16.55, 18.68, 19.10, 19.83, 21.81, 23.00, 23.58° 2θ, ±0.2° 2θ.

15. The compound of claim 13 , wherein the crystalline form is an anhydrate.

16. The compound N-(4-{4-amino-7-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]thieno[3,2-c]pyridin-3-yl}phenyl)-N′-(3-fluorophenyl)urea bimalonate in a solid crystalline form, wherein the crystalline form is Form VI, characterized at least by a powder X-ray diffraction peak at each of the following positions: 6.10, 8.72, 15.76° 2θ, ±0.2° 2θ.

17. The compound of claim 16 wherein the crystalline form is Form VI, characterized at least by a powder X-ray diffraction peak at each of said positions: 6.10, 8.72, 10.67, 11.25, 13.08, 15.27, 15.76, 17.46, 18.27, 18.77, 19.42° 2θ, ±0.2° 2θ.

18. The compound of claim 16 , wherein the crystalline form is an anhydrate.

19. The compound N-(4-{4-amino-7-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]thieno[3,2-c]pyridin-3-yl}phenyl)-N′-(3-fluorophenyl)urea ascorbate in a solid crystalline form, wherein the crystalline form is Form VII, characterized at least by a powder X-ray diffraction peak at each of the following positions: 5.20, 16.01, 17.44, 18.83° 2θ, ±0.2° 2θ.

20. The compound of claim 19 , wherein the crystalline form is Form VII, characterized at least by a powder X-ray diffraction peak at each of said positions: 4.62, 5.20, 6.99, 9.09, 9.66, 10.40, 13.96, 16.01, 17.44, 18.83, 20.93, 22.52, 22.80, 24.13° 2θ, ±0.2° 2θ.

21. The compound of claim 19 , wherein the crystalline form is a hydrate.

22. The compound N-(4-{4-amino-7-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]thieno[3,2-c]pyridin-3-yl}phenyl)-N′-(3-fluorophenyl)urea maleate in a solid crystalline form, wherein the crystalline form is Form VIII, characterized at least by a powder X-ray diffraction peak at each of the following positions: 5.00, 15.23, 19.79, 23.63° 2θ, ±0.2° 2θ.

23. The compound of claim 22 , wherein the crystalline form is Form VIII, characterized at least by a powder X-ray diffraction peak at each of said positions: 5.00, 8.10, 9.30, 10.00, 11.11, 12.22, 13.67, 15.23, 16.85, 18.37, 19.79, 23.63° 2θ, ±0.2° 2θ.

24. The compound of claim 22 , wherein the crystalline form is a hydrate.

25. The compound N-(4-{4-amino-7-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]thieno[3,2-c]pyridin-3-yl}phenyl)-N′-(3-fluorophenyl)urea sulfate in a solid crystalline form, wherein the crystalline form is Form IX, characterized at least by a powder X-ray diffraction peak at each of the following positions: 3.85, 7.67, 11.23, 16.87° 2θ, ±0.2° 2θ.

26. The compound of claim 25 , wherein the crystalline form is Form IX, characterized at least by a powder X-ray diffraction peak at each of said positions: 3.85, 5.62, 6.70, 6.91, 7.67, 11.23, 11.53, 12.99, 16.87, 17.42° 2θ, ±0.2° 2θ.

27. The compound of claim 25 , wherein the crystalline form is a hydrate.

28. The compound N-(4-{4-amino-7-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]thieno[3,2-c]pyridin-3-yl}phenyl)-N′-(3-fluorophenyl)urea sulfate in a solid crystalline form, wherein the crystalline form is Form X, characterized at least by a powder X-ray diffraction peak at each of the following positions: 5.85, 6.57, 6.91, 20.85° 2θ, ±0.2° 2θ.

29. The compound of claim 28 , wherein the crystalline form is Form X, characterized at least by a powder X-ray diffraction peak at each of said positions: 5.85, 6.57, 6.91, 13.83, 17.65, 18.74, 19.12, 20.85° 2θ, ±0.2° 2θ.

30. The compound of claim 28 , wherein the crystalline form is a hydrate.