Crystalline salts of a B-RAF kinase inhibitor

1. A method of treating a cancer in a patient, comprising administering to the patient a therapeutically effective amount of 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°, wherein the cancer is an intestinal cancer.

2. The method of claim 1 , wherein the method further comprises administering to the patient a chemotherapeutic agent.

3. The method of claim 2 , wherein the chemotherapeutic agent is selected from one of the following: hormones, hormone analogues and antihormones, aromatase inhibitors, LHRH agonists and antagonists, inhibitors of growth factors, antimetabolites, antitumour antibiotics, platinum derivatives, alkylation agents, antimitotic agents, tubuline inhibitors, PARP inhibitors, topoisomerase inhibitors, serine/threonine kinase inhibitors, tyrosine kinase inhibitors, protein-protein interaction inhibitors, MEK inhibitors, ERK inhibitors, IGF- 1 R inhibitors, ErbB receptor inhibitors, rapamycin analogs, amifostin, anagrelid, clodronat, filgrastin, interferon, leucovorin, rituximab, procarbazine, levamisole, mesna, mitotane, pamidronate, or porfimer.

4. The method of claim 3 , wherein the chemotherapeutic agent is a platinum derivative, an alkylation agent, a serine/threonine kinase inhibitor, a tyrosine kinase inhibitor, a MEK inhibitor, an ERK inhibitor, an ErbB receptor inhibitor, a rapamycin analog, an interferon, or procarbazine.

5. A combination comprising 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°, and a chemotherapeutic agent for the treatment of cancer; wherein the cancer is breast cancer, prostate cancer, colon cancer, endometrial cancer, brain cancer, bladder cancer, skin cancer, uterine cancer, lung cancer, pancreatic cancer, renal cancer, gastric cancer, a hematological cancer, a malignant melanoma, thyroid cancer, colorectal cancer, biliary tract cancer, ovarian cancer, non- small cell lung cancer, or intestinal cancer.

6. The combination of claim 5 , wherein the chemotherapeutic agent is selected from one of the following classes of drugs:

hormones, hormone analogues and antihormones, aromatase inhibitors, LHRH agonists and antagonists, inhibitors of growth factors, antimetabolites, antitumour antibiotics, platinum derivatives, alkylation agents, antimitotic agents, tubuline inhibitors, PARP inhibitors, topoisomerase inhibitors, serine/threonine kinase inhibitors, tyrosine kinase inhibitors, protein-protein interaction inhibitors, MEK inhibitors, ERK inhibitors, IGF- 1 R inhibitors, ErbB receptor inhibitors, rapamycin analogs, amifostin, anagrelid, clodronat, filgrastin, interferon, leucovorin, rituximab, procarbazine, levamisole, mesna, mitotane, pamidronate, or porfimer.

7. The combination of claim 6 , wherein the chemotherapeutic agent is a platinum derivative, an alkylation agent, a serine/threonine kinase inhibitor, a tyrosine kinase inhibitor, a MEK inhibitor, an ERK inhibitor, an ErbB receptor inhibitor, a rapamycin analog, an interferon, or a procarbazine.

8. The combination of claim 5 , wherein the 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 and the chemotherapeutic agent are co-formulated.

9. The combination of claim 5 , wherein the 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 and the chemotherapeutic agent are co-formulated as a pharmaceutical composition.

10. The combination of claim 5 , wherein the 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 and the chemotherapeutic agent are each separately formulated as a pharmaceutical composition.

11. A pharmaceutical formulation for oral administration comprising about 5 to about 1000 mg of 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°, and a pharmaceutically acceptable carrier.

12. The formulation of claim 11 , wherein the formulation is a capsule.

13. The formulation of claim 11 , wherein the formulation is a hard gelatin capsule.

14. The formulation of claim 11 , wherein the formulation is a tablet.

15. The formulation of claim 11 , comprising about 10 mg, about 30 mg, or about 100 mg of 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.

16. The formulation of claim 11 , wherein the 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 is ground, mixed with one or more pharmaceutically acceptable carriers, screened, and compressed.