Solid forms of cerdulatinib
Forms of cerdulatinib and salts or co-crystals thereof were prepared and characterized in the solid state. Also provided are processes of manufacture and methods of using the forms cerdulatinib and salts or co-crystals thereof.
1. A crystalline mono-hydrochloride salt of Compound I:
characterized by an X-ray powder diffractogram comprising peaks at 8.7, 15.9, and 20.0°2θ, each ±0.2°2θ, as determined on a diffractometer using Cu-Kα radiation (Compound I HCl Form I).
2. The salt of claim 1 , further characterized by one or more peaks at 11.5, 22.5, and 25.5°2θ, each ±0.2°2θ.
3. The salt of claim 1 , further characterized by a differential scanning calorimetry curve comprising an endotherm with onset at about 288° C.
4. A pharmaceutical composition comprising one or more pharmaceutically acceptable carriers, and a therapeutically effective amount of a salt of claim 1 .
5. The pharmaceutical composition of claim 4 , wherein the salt comprises at least about 50% w/w of Compound I HCl Form I of claim 1 .
6. A pharmaceutical composition comprising the salt of claim 1 , and another therapeutic agent.
7. A method for treating a disease or condition mediated by a protein kinase in a patient in need thereof, comprising administering to the patient a therapeutically effective amount of a salt of claim 1 .
8. The method of claim 7 , wherein the protein kinase is JAK or any mutation thereof.
9. The method of claim 7 , wherein the protein kinase is SYK or any mutation thereof.
10. The method of claim 7 , wherein the disease or condition is chronic lymphocytic leukemia (CLL), small lymphocytic lymphoma (SLL), follicular lymphoma (FL), transformed follicular lymphoma (tFL), diffuse large B-cell lymphoma (DLBCL), mantle cell lymphoma (MCL), B-cell non-Hodgkin's lymphoma (NHL), peripheral T-cell lymphoma (PTCL) cutaneous T-cell lymphoma (CTCL), marginal zone lymphoma, mucosa-associated lymphoid tissue (MALT), or Waldenstrom macroglobulinemia (WM).
11. The method of claim 10 , wherein the disease or condition is chronic lymphocytic leukemia (CLL).
12. The method of claim 10 , wherein the disease or condition is small lymphocytic lymphoma (SLL).
13. The method of claim 10 , wherein the disease or condition is follicular lymphoma (FL) or transformed follicular lymphoma (tFL).
14. The method of claim 10 , wherein the disease or condition is diffuse large B-cell lymphoma (DLBCL).
15. The method of claim 10 , wherein the disease or condition is mantle cell lymphoma (MCL).
16. The method of claim 10 , wherein the disease or condition is B-cell non-Hodgkin's lymphoma (NHL).
17. The method of claim 10 , wherein the disease or condition is peripheral T-cell lymphoma (PTCL) or cutaneous T-cell lymphoma (CTCL).
18. The method of claim 10 , wherein the disease or condition is marginal zone lymphoma.
19. The method of claim 10 , wherein the disease or condition is mucosa-associated lymphoid tissue (MALT).
20. The method of claim 10 , wherein the disease or condition is Waldenstrom macroglobulinemia (WM).
21. A crystalline hydrochloride salt of Compound I:
characterized by an X-ray powder diffractogram comprising peaks at 7.9, 19.6, and 13.3°2θ, each ±0.2°2θ, as determined on a diffractometer using Cu-Kα radiation (Compound I HCl Type B).
22. The salt of claim 21 , further characterized by one or more peaks at 22.5, 17.2, and 9.7°2θ, each ±0.2°2θ.
23. The salt of claim 21 , further characterized by a differential scanning calorimetry curve comprising an endotherm with onset at about 286° C.
24. A pharmaceutical composition comprising one or more pharmaceutically acceptable carriers, and a therapeutically effective amount of a salt of claim 21 .
25. The pharmaceutical composition of claim 24 , wherein the salt comprises at least about 50% w/w of Compound I HCl Type B of claim 21 .
26. A pharmaceutical composition comprising the salt of claim 21 , and another therapeutic agent.
27. A method for treating a disease or condition mediated by a protein kinase in a patient in need thereof, comprising administering to the patient a therapeutically effective amount of a salt of claim 21 .
28. The method of claim 27 , wherein the protein kinase is JAK or any mutation thereof.
29. The method of claim 27 , wherein the protein kinase is SYK or any mutation thereof.
30. The method of claim 27 , wherein the disease or condition is chronic lymphocytic leukemia (CLL), small lymphocytic lymphoma (SLL), follicular lymphoma (FL), transformed follicular lymphoma (tFL), diffuse large B-cell lymphoma (DLBCL), mantle cell lymphoma (MCL), B-cell non-Hodgkin's lymphoma (NHL), peripheral T-cell lymphoma (PTCL) cutaneous T-cell lymphoma (CTCL), marginal zone lymphoma, mucosa-associated lymphoid tissue (MALT), or Waldenstrom macroglobulinemia (WM).
31. The method of claim 30 , wherein the disease or condition is chronic lymphocytic leukemia (CLL).
32. The method of claim 30 , wherein the disease or condition is small lymphocytic lymphoma (SLL).
33. The method of claim 30 , wherein the disease or condition is follicular lymphoma (FL) or transformed follicular lymphoma (tFL).
34. The method of claim 30 , wherein the disease or condition is diffuse large B-cell lymphoma (DLBCL).
35. The method of claim 30 , wherein the disease or condition is mantle cell lymphoma (MCL).
36. The method of claim 30 , wherein the disease or condition is B-cell non-Hodgkin's lymphoma (NHL).
37. The method of claim 30 , wherein the disease or condition is peripheral T-cell lymphoma (PTCL) or cutaneous T-cell lymphoma (CTCL).
38. The method of claim 30 , wherein the disease or condition is marginal zone lymphoma.
39. The method of claim 30 , wherein the disease or condition is mucosa-associated lymphoid tissue (MALT).
40. The method of claim 30 , wherein the disease or condition is Waldenstrom macroglobulinemia (WM).