Crystalline salts of a B-RAF kinase inhibitor

1. Crystalline N-(3-(5-((1-ethylpiperidin-4-yl)(methyl)amino)-3-(pyrimidin-5-yl)-1H-pyrrolo[3,2-b]pyridin-1-yl)-2,4-difluorophenyl)propane-1-sulfonamide monosuccinate salt, having an X-ray powder diffraction pattern comprising at least one of the following peaks, in terms of 2θ: 15.4°±0.5°; 20.0°±0.5°; and 21.8°±0.5°.

2. The crystalline salt of claim 1 which is substantially anhydrous and non-solvated.

3. The crystalline salt of claim 1 , having an X-ray powder diffraction pattern comprising a peak, in terms of 2θ, at 15.4°±0.5°.

4. The crystalline salt of claim 1 , having an X-ray powder diffraction pattern comprising the following peaks, in terms of 2θ: 15.4°±0.5°; 20.0°±0.5°; and 21.8°±0.5°.

5. The crystalline salt of claim 1 having an X-ray powder diffraction pattern substantially as shown in FIG. 10 , FIG. 26 , or FIG. 38 .

6. The crystalline salt of claim 1 having a differential scanning calorimetry thermogram (DSC) substantially as shown in FIG. 11 , FIG. 27 , or FIG. 39 .

7. The crystalline salt of claim 1 having a thermogravimetric analysis (TGA) substantially as shown in FIG. 12 , FIG. 28 or FIG. 39 .

8. A composition comprising the crystalline salt of claim 1 .

9. The composition of claim 8 wherein the composition comprises at least one pharmaceutically acceptable carrier.

10. The composition of claim 9 , wherein the composition is a tablet.

11. A process for preparing the crystalline salt of claim 1 comprising reacting N-(3-(5-((1-ethylpiperidin-4-yl)(methyl)amino)-3-(pyrimidin-5-yl)-1H-pyrrolo[3,2-b]pyridin-1-yl)-2,4-difluorophenyl)propane-1-sulfonamide with one equivalent of succinic acid.

12. The process of claim 11 further comprising crystallizing the salt from a C 1-4 alcohol or aqueous C 1-4 alcohol or ethyl acetate.

13. The process of claim 11 further comprising crystallizing the salt from ethanol, isopropanol, aqueous ethanol, aqueous isopropanol, or ethyl acetate.

14. A method of treating a cancer in a patient, comprising administering to the patient a therapeutically effective amount of a crystalline salt of claim 1 , wherein the cancer is breast cancer, prostate cancer, colon cancer, endometrial cancer, brain cancer, bladder cancer, skin cancer, uterus cancer, ovarian cancer, lung cancer, pancreatic cancer, renal cancer, gastric cancer, hematological cancer, malignant melanoma, thyroid cancer, colorectal cancer, or biliary tract cancer.

15. The method of claim 14 , wherein the cancer is lung cancer.

16. The method of claim 14 , wherein the cancer is malignant melanoma.

17. The method of claim 14 , wherein the cancer is thyroid cancer.

18. The method of claim 14 , wherein the cancer is colorectal cancer.

19. The method of claim 14 , wherein the cancer is biliary tract cancer.

20. The method of claim 14 , wherein the cancer is non-small cell lung cancer.