Solid forms of a Cot inhibitor compound
Disclosed are solid forms of a Cot (cancer Osaka thyroid) inhibitor and corresponding methods of preparation thereof, wherein the Cot inhibitor has the following formula:
1. A solid form of Compound 1:
wherein the solid form is Freebase Form I characterized by an XRPD pattern comprising peaks at 10.4, 13.0, and 18.1 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
2. The solid form of claim 1 , characterized by an XRPD pattern further comprising one or more peaks at 18.8, 22.6, and 25.6 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
3. The solid form of claim 1 , characterized by an XRPD pattern further comprising one or more peaks at 19.2, 21.6, and 24.1 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
4. The solid form of claim 1 , characterized by an XRPD pattern comprising peaks at 10.4, 13.0, 18.1, 18.8, 19.2, 21.6, 22.6, 24.1, and 25.6 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
5. The solid form of claim 1 , characterized by an XRPD pattern as substantially shown in FIG. 2 .
6. The solid form of claim 1 , characterized by a DSC curve as substantially shown in FIG. 3 .
7. The solid form of claim 1 , characterized by a TGA thermogram as substantially shown in FIG. 4 .
8. A solid form of an oxalate salt of Compound 1:
wherein the solid form is Oxalate Form I characterized by an XRPD pattern comprising peaks at 5.2, 6.3, and 7.5 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
9. The solid form of claim 8 , characterized by an XRPD pattern further comprising one or more peaks at 10.3, 13.3, and 22.6 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
10. The solid form of claim 8 , characterized by an XRPD pattern further comprising one or more peaks at 12.6, 16.4, and 17.9° 2 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
11. The solid form of claim 8 , characterized by an XRPD pattern comprising peaks at 5.2, 6.3, 7.5, 10.3, 12.6, 13.3, 16.4, 17.9, and 22.6 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
12. The solid form of claim 8 , characterized by an XRPD pattern as substantially shown in FIG. 26 .
13. The solid form of claim 8 , characterized by a DSC curve that comprises an endotherm with an onset at about 220° C.
14. The solid form of claim 8 , characterized by a DSC curve as substantially shown in FIG. 27 .
15. The solid form of claim 8 , characterized by a TGA thermogram as substantially shown in FIG. 28 .
16. A solid form of a maleate salt of Compound 1:
wherein the solid form is characterized by an XRPD pattern comprising peaks at 8.2, 8.6, and 11.9 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
17. The solid form of claim 16 , characterized by an XRPD pattern further comprising one or more peaks at 9.6, 17.3, and 19.1 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
18. The solid form of claim 16 , characterized by an XRPD pattern further comprising one or more peaks at 15.1, 21.1, and 23.5 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
19. The solid form of claim 16 , characterized by an XRPD pattern comprising peaks at 8.2, 8.6, 9.6, 11.9, 15.1, 17.3, 19.1 21.1, and 23.5 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
20. The solid form of claim 16 , characterized by an XRPD pattern as substantially shown in FIG. 35 .
21. The solid form of claim 16 , characterized by a DSC curve that comprises an endotherm with onset at about 130° C. and an exotherm with onset at about 160° C.
22. The solid form of claim 16 , characterized by a DSC curve as substantially shown in FIG. 36 .
23. The solid form of claim 16 , characterized by a TGA thermogram as substantially shown in FIG. 37 .
24. A solid form of a camsylate salt of Compound 1:
wherein the solid form is Camsylate Form I characterized by an XRPD pattern comprising peaks at 5.4, 12.0, and 17.5 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
25. The solid form of claim 24 , characterized by an XRPD pattern further comprising one or more peaks at 10.1, 19.5, 22.4 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
26. The solid form of claim 24 , characterized by an XRPD pattern further comprising one or more peaks at 6.7, 8.3, and 20.5 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
27. The solid form of claim 24 , characterized by an XRPD pattern comprising peaks at 5.4, 6.7, 8.3, 10.1, 12.0, 17.5, 19.5, 20.5, and 22.4 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
28. The solid form of claim 24 , characterized by an XRPD pattern as substantially shown in FIG. 38 .
29. The solid form of claim 24 , characterized by a DSC curve that comprises a broad endotherm between ambient temperature to about 120° C. followed by a melting onset at about 196° C.
30. The solid form of claim 24 , characterized by a DSC curve as substantially shown in FIG. 39 .
31. The solid form of claim 24 , characterized by a TGA thermogram as substantially shown in FIG. 40 .
32. A solid form of a camyslate salt of Compound 1:
wherein the solid form is Camsylate Form II characterized by an XRPD pattern comprising peaks at 2.8, 4.7, and 5.4 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
33. The solid form of claim 32 , characterized by an XRPD pattern further comprising one or more additional peaks at 7.2, 8.1, and 10.8 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
34. The solid form of claim 32 , characterized by an XRPD pattern further comprising one or more peaks at 9.8, 12.4, and 17.7 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
35. The solid form of claim 32 , characterized by an XRPD pattern comprising peaks at 2.8, 4.7, 5.4, 7.2, 8.1, 9.8, 10.8, 12.4, and 17.7 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
36. The solid form of claim 32 , characterized by an XRPD pattern as substantially shown in FIG. 41 .
37. The solid form of claim 32 , characterized by a DSC curve that comprises a broad endotherm between ambient temperature to about 120° C. followed by several endotherms at about 130° C., 198° C., and 214° C., respectively.
38. The solid form of claim 32 , characterized by a DSC curve as substantially shown in FIG. 42 .
39. The solid form of claim 32 , characterized by a TGA thermogram as substantially shown in FIG. 43 .
40. A solid form of a camsylate salt of Compound 1:
wherein the solid form is Camsylate Form III characterized by an XRPD pattern comprising peaks at 5.5, 8.9, and 18.5 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
41. The solid form of claim 40 , characterized by an XRPD pattern further comprising one or more peaks at 4.5, 10.9, and 16.6 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
42. The solid form of claim 40 , characterized by an XRPD pattern further comprising one or more peaks at 12.2, 21.5, and 21.8 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
43. The solid form of claim 40 , characterized by an XRPD pattern comprising peaks at 4.5, 5.5, 8.9, 10.9, 12.2, 16.6, 18.5, 21.5, and 21.8 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
44. The solid form of claim 40 , characterized by an XRPD pattern as substantially shown in FIG. 44 .
45. The solid form of claim 40 , characterized by a DSC curve that comprises a broad endotherm between ambient temperature to about 100° C. followed by a melting endotherm with an onset at about 207° C.
46. The solid form of claim 40 , characterized by a DSC curve as substantially shown in FIG. 45 .
47. The solid form of claim 40 , characterized by a TGA thermogram as substantially shown in FIG. 46 .