Solid forms of N-[2,4-bis(1,1-dimethylethyl)-5-hydroxypheny1]-1,4-dihydro-4-oxoquinoline-3-carboxamide

1. A compound selected from N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•2-methylbutyric acid, N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•propylene glycol, N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•PEG 400•KOAc, N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•lactic acid, N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•isobutyric acid, N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•propionic acid, N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•2-propanol, N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•besylate, and N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•besylate•H 2 O.

2. Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•2-methylbutyric acid.

3. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•2-methylbutyric acid of claim 2 , wherein the N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide:2-methylbutyric acid are in a ratio of 1:1.

4. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•2-methylbutyric acid of claim 2 , characterized by a peak at 5.8 degrees, 6.7 degrees, 8.8 degrees, 10.1 degrees, 11.4 degrees, 13.9 degrees, 16.9 degrees, and 17.4 degrees in an X-ray powder diffraction pattern.

5. The crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•2-methylbutyric acid of claim 2 having a triclinic crystal system, having a P-1 space group, and having the following unit cell dimensions in Å when measured at 120K:

a=10.5

b=16.2

c=17.7.

6. The crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•2-methylbutyric acid of claim 2 characterized by a weight loss of from about 20 to about 22% in a temperature range of from about 60° C. to about 198° C.

7. Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•propylene glycol.

8. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•propylene glycol of claim 7 , wherein the N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide: propylene glycol are in a ratio of 1:1.

9. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•propylene glycol of claim 7 , characterized by a peak at 10.1 degrees, 11.7 degrees, 12.1 degrees, 13.3 degrees, 13.7 degrees, 14.2 degrees, 15.5 degrees, 18.1 degrees, 19.4 degrees, 20.5 degrees, 22.6 degrees, 24.6 degrees, and 25.0 degrees in an X-ray powder diffraction pattern.

10. The crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•propylene glycol of claim 7 characterized by a weight loss of from about 16 to about 17% with an onset temperature of about 144° C.

11. Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•PEG 400•KOAc.

12. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•PEG 400•KOAc of claim 11 , wherein the N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide: PEG 400•KOAc are in a ratio of 2:1:1.

13. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•PEG 400•KOAc of claim 11 , characterized by a peak at 6.2 degrees, 8.1 degrees, 9.7 degrees, 12.2 degrees, 13.1 degrees, 13.7 degrees, 14.4 degrees, 16.3 degrees, 16.9 degrees, 18.5 degrees, 19.2 degrees, and 20.5 degrees in an X-ray powder diffraction pattern.

14. The crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•PEG 400•KOAc of claim 11 having a monoclinic crystal system, having a P2/n space group, and having the following unit cell dimensions as measured in Å at 120K:

a=14.5

b=14.5

c=16.5.

15. The crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•PEG 400•KOAc of claim 11 characterized by a weight loss of from about 1 to about 2% with an onset temperature of from about 140° C. to about 172° C.

16. Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•lactic acid.

17. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•lactic acid of claim 16 , wherein the N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide: lactic acid are in a ratio of 1:1.

18. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•lactic acid of claim 16 , characterized by a peak at 7.3 degrees, 11.3 degrees, 13.4 degrees, 14.4 degrees, 15.4 degrees, 17.2 degrees, 18.0 degrees, 18.7 degrees, 19.5 degrees, and 21.7 degrees in an X-ray powder diffraction pattern.

19. The crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•lactic acid of claim 16 , having a triclinic crystal system, having a P-1 space group, and having the following unit cell dimensions as measured in Å at 100K:

a=9.1

b=11.9

c=12.3.

20. The crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•lactic acid of claim 16 characterized by a weight loss of from about 20 to about 21% with an onset temperature of about 173° C.

21. Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•isobutyric acid.

22. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•isobutyric acid of claim 21 , wherein the N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide: isobutyric acid are in a ratio of 1:2.

23. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•isobutyric acid of claim 21 , characterized by a peak at 5.2 degrees, 6.5 degrees, 9.4 degrees, 10.3 degrees, 12.6 degrees, 13.3 degrees, 14.2 degrees, 15.0 degrees, 15.5 degrees, 16.0 degrees, 18.0 degrees, 18.4 degrees, 18.8 degrees, 19.4 degrees, 19.9 degrees, 20.7 degrees, 21.2 degrees, 25.3 degrees, and 27.6 degrees in an X-ray powder diffraction pattern.

24. The crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•isobutyric acid of claim 21 having a triclinic crystal system, having a P-1 space group, and having the following unit cell dimensions as measured in Å at 100K:

a=13.3

b=14.8

c=18.2.

25. The crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•isobutyric acid of claim 21 characterized by a weight loss of from about 30 to about 31% with an onset temperature of about 60° C. to about 184° C.

26. Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•propionic acid.

27. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•propionic acid of claim 26 , wherein the N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide: propionic acid are in a ratio of 1:2.

28. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•propionic acid of claim 26 , characterized by a peak at 5.3 degrees, 7.1 degrees, 10.3 degrees, 10.7 degrees, 13.1 degrees, 16.0 degrees, 18.8 degrees, 19.7 degrees, and 20.1 degrees in an X-ray powder diffraction pattern.

29. The crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•propionic acid of claim 26 , having a triclinic crystal system, having a P-1 space group, and having the following unit cell dimensions as measured in Å at 100K:

a=6.8

b=13.2

c=17.6.

30. The crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•propionic acid of claim 26 characterized by a weight loss of from about 26 to about 27% with an onset temperature of about 60° C. to about 160° C.

31. Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•2-propanol.

32. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•2-propanol of claim 31 , wherein the N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide: 2-propanol are in a ratio of 1:1.5.

33. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•2-propanol of claim 31 , characterized by a peak at 6.2, at 10.3 degrees, at 12.3 degrees, at 13.5 degrees, at 14.0 degrees, at 15.1 degrees, at 18.5 degrees, at 20.7 degrees, at 22.5 degrees, and at 23.8 degrees in an X-ray powder diffraction pattern.

34. The crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•2-propanol of claim 31 , having a monoclinic crystal system, having a P2/n space group, and having the following unit cell dimensions as measured in Å at 100K:

a=17.0

b=9.9

c=17.3.

35. The crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•2-propanol of claim 31 characterized by a weight loss of from about 18 to about 19% with an onset temperature of about 60° C. to about 201° C.

36. Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•H 2 O.

37. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•H 2 O of claim 36 , wherein the N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide:H 2 O are in a ratio of 1:1.

38. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•H 2 O of claim 36 , characterized by a peak at 6.2 degrees, at 7.6 degrees, at 8.4 degrees, at 11.0 degrees, at 12.3 degrees, at 14.8 degrees, at 16.1 degrees, at 17.1 degrees, at 18.0 degrees, at 18.5 degrees, at 19.4 degrees, at 21.0 degrees, at 22.5 degrees, at 23.4 degrees, at 23.9 degrees, at 24.9 degrees, at 25.5 degrees, at 26.7 degrees, at 27.5 degrees, at 29.6 degrees, at 33.5 degrees, and at 36.8 degrees in an X-ray powder diffraction pattern.

39. Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•besylate.

40. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•besylate of claim 39 , wherein the N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•besylate are in a ratio of 1:1.

41. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•besylate of claim 39 , characterized by a peak at 7.0 degrees, at 12.9 degrees, at 13.8 degrees, at 16.4 degrees, and at 18.7 degrees in an X-ray powder diffraction pattern.

42. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•besylate of claim 39 , characterized by a peak at 6.2 degrees, at 10.7 degrees, at 12.8 degrees, at 13.6 degrees, at 15.0 degrees, at 17.5 degrees, at 19.1 degrees, at 20.0 degrees, at 21.0 degrees, and at 28.9 degrees in an X-ray powder diffraction pattern.

43. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•besylate of claim 39 , characterized by a peak at 6.8, 12.6, 15.0, 17.8, 18.9, 21.2, 23.5, and 29.9 degrees in an X-ray powder diffraction pattern.

44. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•besylate of claim 39 , characterized by a peak at 3.4, 6.7, 12.4, 12.6, 18.2, 18.9, 20.2, 21.1, and 23.4 degrees in an X-ray powder diffraction pattern.

45. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•besylate of claim 39 , characterized by a peak at 6.5, 16.5, 18.6, 19.7 and 24.0 degrees in an X-ray powder diffraction pattern.

46. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•besylate of claim 39 , wherein the N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•besylate are in a ratio of 2:1.

47. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•besylate of claim 46 , characterized by a peak at 5.2, 10.7, 11.2, 12.4, 14.9, and 15.2 degrees in an X-ray powder diffraction pattern.

48. Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•besylate•H 2 O.

49. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•besylate•H 2 O of claim 48 , wherein the N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•besylate•H 2 O are in a ratio of 1:2:1.

50. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•besylate•H 2 O of claim 49 , characterized by a peak at 5.1, 8.7, 13.1, 17.8, 18.2, 20.3, 21.1, 22.4, 24.2, and 26.1 degrees in an X-ray powder diffraction pattern.

51. The crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•besylate of claim 39 having a triclinic crystal system, having a P-1 bar space group, and having the following unit cell dimensions in {acute over (Å)} when measured at 120K:

a=13.5;

b=14.2; and

c=15.7.

52. The crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•besylate of claim 39 having a monoclinic crystal system, having a P2 1 /n space group, and having the following unit cell dimensions in {acute over (Å)} when measured at 120K:

a=10.9;

b=53.2; and

c=11.3.

53. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•besylate of claim 46 having a monoclinic crystal system, having a P2 1 /c space group, and having the following unit cell dimensions in {acute over (Å)} when measured at 120K:

a=17.6;

b=17.7; and

c=18.9.

54. The Crystalline N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•besylate•H 2 O of claim 49 having a triclinic crystal system, having a P-1 bar space group, and having the following unit cell dimensions in {acute over (Å)} when measured at 120K:

a=10.3;

b=10.6; and

c=17.6.

55. A pharmaceutical preparation comprising a compound selected from N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•2-methylbutyric acid, N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•propylene glycol, N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•PEG 400•KOAc, N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•lactic acid, N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•isobutyric acid, N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•propionic acid, N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•2-propanol, N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•besylate, and N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•besylate•H 2 O.

56. A pharmaceutical pack or kit comprising:

a solid form of a compound selected from N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•2-methylbutyric acid, N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•propylene glycol, N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•PEG 400•KOAc, N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•lactic acid, N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•isobutyric acid, N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•propionic acid, N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•2-propanol, N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•besylate, and N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide•besylate•H 2 O; and

a pharmaceutically acceptable carrier.