Claims for Patent: 9,221,788

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Summary for Patent: 9,221,788

Title:	Salts and solid forms of (S)-3-(4- (4-(morpholinomethyl)benzyl)oxy)-1-oxoisoindolin-2-yl)piperidine-2,6-dione and compositions comprising and methods of using the same
Abstract:	Salts and solid forms of 3-(4-((4-(morpholinomethyl)benzyl)oxy)-1-oxoisoindolin-2-yl)piperidine-2,6-dione, or a stereoisomer thereof, are disclosed. Compositions comprising and methods of using the salts and solid forms are also disclosed.
Inventor(s):	Benjamin M. Cohen, John F. Traverse, Jean Xu, Ying Li
Assignee:	Celgene Corp
Application Number:	US13/962,745
Patent Claims:	1. A solid form comprising a salt, hydrate, or solvate of Compound (I-S): wherein the solid form is crystalline, wherein the solid form comprises Compound (I-S) and water, having an XRPD pattern comprising peaks at approximately 8.31, 11.80, and 17.37 degrees 2θ; comprises Compound (I-S) and THF, having an XRPD pattern comprising peaks at approximately 11.80, 20.89, and 22.16 degrees 2θ; comprises a besylate salt of Compound (I-S), having an XRPD pattern comprising peaks at approximately 19.07, 20.71, and 23.96 degrees 2θ; comprises a DMSO solvate of a besylate salt of Compound (I-S), having an XRPD pattern comprising peaks at approximately 16.88, 18.14, and 20.02 degrees 2θ; comprises a D-tartrate salt of Compound (I-S), having an XRPD pattern comprising peaks at approximately 17.00, 19.73, and 25.86 degrees 2θ; comprises a hemi D-tartrate salt of Compound (I-S), having an XRPD pattern comprising peaks at approximately 6.21, 12.91, and 16.32 degrees 2θ; comprises a L-tartrate salt of Compound (I-S), having an XRPD pattern comprising peaks at approximately 6.27, 10.90, and 15.32 degrees 2θ; comprises a tosylate salt of Compound (I-S), having an XRPD pattern comprising peaks at approximately 9.77, 15.41, and 19.25 degrees 2θ; or comprises a (+) camphorsulfonic acid salt of Compound (I-S), having an XRPD pattern comprising peaks at approximately 9.05, 14.61, and 16.82 degrees 2θ. 2. A solid form comprising a racemic Compound (I): or a salt, hydrate, anhydrate, or solvate thereof, wherein the solid form is crystalline, wherein the solid form comprises racemic Compound (I), having an XRPD pattern comprising peaks at approximately 4.95, 8.96, and 14.83 degrees 2θ; comprises racemic Compound (I) and water, having an XRPD pattern comprising peaks at approximately 14.01, 17.28, and 26.21 degrees 2θ; comprises a HCl salt of racemic Compound (I) and water, having an XRPD pattern comprising peaks at approximately 13.88, 14.30, and 15.36 degrees 2θ; or comprises a HCl salt of racemic Compound (I) and methanol, having an XRPD pattern comprising peaks at approximately 12.38, 14.54, and 26.10 degrees 2θ. 3. The solid form of claim 1, comprising Compound (I-S) and water having an XRPD pattern comprising peaks at approximately 8.31, 11.80, and 17.37 degrees 2θ. 4. The solid form of claim 3, further comprises peaks at approximately 13.79, 17.15, and 26.00 degrees 2θ. 5. The solid form of claim 3, comprising Compound (I-S) and water, wherein the solid form is characterized by an XRPD diffraction pattern which matches the XRPD pattern presented in FIG. 5. 6. The solid form of claim 1, comprising Compound (I-S) and THF having an XRPD pattern comprising peaks at approximately 11.80, 20.89, and 22.16 degrees 2θ. 7. The solid form of claim 6, further comprises peaks at approximately 6.03 and 18.59 degrees 2θ. 8. The solid form of claim 6, comprising Compound (I-S) and THF, wherein the solid form is characterized by an XRPD diffraction pattern which matches the XRPD pattern presented in FIG. 8. 9. The solid form of claim 1, comprising a besylate salt of Compound (I-S) having an XRPD pattern comprising peaks at approximately 19.07, 20.71, and 23.96 degrees 2θ. 10. The solid form of claim 9, further comprises peaks at approximately 15.48 and 15.92 degrees 2θ. 11. The solid form of claim 9, comprising a besylate salt of Compound (I-S), wherein the solid form is characterized by an XRPD diffraction pattern which matches the XRPD pattern presented in FIG. 11. 12. The solid form of claim 1, comprising a DMSO solvate of a besylate salt of Compound (I-S) having an XRPD pattern comprising peaks at approximately 16.88, 18.14, and 20.02 degrees 2θ. 13. The solid form of claim 12, further comprises peaks at approximately 7.31 and 24.49 degrees 2θ. 14. The solid form of claim 12, comprising a DMSO solvate of a besylate salt of Compound (I-S), wherein the solid form is characterized by an XRPD diffraction pattern which matches the XRPD pattern presented in FIG. 16. 15. The solid form of claim 1, comprising a D-tartrate salt of Compound (I-S) having an XRPD pattern comprising peaks at approximately 17.00, 19.73, and 25.86 degrees 2θ. 16. The solid form of claim 15, further comprises peaks at approximately 19.25 and 21.25 degrees 2θ. 17. The solid form of claim 15, comprising a D-tartrate salt of Compound (I-S), wherein the solid form is characterized by an XRPD diffraction pattern which matches the XRPD pattern presented in FIG. 20. 18. The solid form of claim 1, comprising a hemi D-tartrate salt of Compound (I-S) having an XRPD pattern comprising peaks at approximately 6.21, 12.91, and 16.32 degrees 2θ. 19. The solid form of claim 18, further comprises peaks at approximately 12.32 and 19.09 degrees 2θ. 20. The solid form of claim 18, comprising a hemi D-tartrate salt of Compound (I-S), wherein the solid form is characterized by an XRPD diffraction pattern which matches the XRPD pattern presented in FIG. 23. 21. The solid form of claim 1, comprising a L-tartrate salt of Compound (I-S) having an XRPD pattern comprising peaks at approximately 6.27, 10.90, and 15.32 degrees 2θ. 22. The solid form of claim 21, further comprises peaks at approximately 11.97, 14.41, and 17.08 degrees 2θ. 23. The solid form of claim 21, comprising a L-tartrate salt of Compound (I-S), wherein the solid form is characterized by an XRPD diffraction pattern which matches the XRPD pattern presented in FIG. 26. 24. The solid form of claim 1, comprising a tosylate salt of Compound (I-S) having an XRPD pattern comprising peaks at approximately 9.77, 15.41, and 19.25 degrees 2θ. 25. The solid form of claim 24, further comprises peaks at approximately 7.41 and 22.97 degrees 2θ. 26. The solid form of claim 24, comprising a tosylate salt of Compound (I-S), wherein the solid form is characterized by an XRPD diffraction pattern which matches the XRPD pattern presented in FIG. 29. 27. The solid form of claim 1, comprising a (+) camphorsulfonic acid salt of Compound (I-S) having an XRPD pattern comprising peaks at approximately 9.05, 14.61, and 16.82 degrees 2θ. 28. The solid form of claim 27, further comprises peaks at approximately 13.97, 15.34, and 16.35 degrees 2θ. 29. The solid form of claim 27, comprising a (+) camphorsulfonic acid salt of Compound (I-S), wherein the solid form is characterized by an XRPD diffraction pattern which matches the XRPD pattern presented in FIG. 32. 30. A solid form comprising a HCl salt of Compound (I-S): or a salt, hydrate, anhydrate, or solvate of the HCl salt, wherein the solid form is crystalline, wherein the solid form is Form A crystal form characterized by an XRPD pattern comprising peaks at approximately 15.09, 15.94, and 22.30 degrees 2θ; is Form B crystal form characterized by an XRPD pattern comprising peaks at approximately 7.11, 14.20, and 20.71 degrees 2θ; is Form C crystal form characterized by an XRPD pattern comprising peaks at approximately 6.55, 13.14, and 13.37 degrees 2θ; is Form D crystal form characterized by an XRPD pattern comprising peaks at approximately 13.52, 14.16, and 25.00 degrees 2θ; is Form E crystal form characterized by an XRPD pattern comprising peaks at approximately 9.82, 17.06, and 17.73 degrees 2θ; is Form F crystal form characterized by an XRPD pattern comprising peaks at approximately 13.71, 14.22, and 20.87 degrees 2θ; is Form G crystal form characterized by an XRPD pattern comprising peaks at approximately 6.85, 20.20, and 20.60 degrees 2θ; is Form H crystal form characterized by an XRPD pattern comprising peaks at approximately 6.83, 20.19, and 20.58 degrees 2θ; is Form I crystal form characterized by an XRPD pattern comprising peaks at approximately 13.95, 23.39, and 24.10 degrees 2θ; is Form J crystal form characterized by an XRPD pattern comprising peaks at approximately 4.86, 13.48, and 20.06 degrees 2θ; or is Form K crystal form characterized by an XRPD pattern comprising peaks at approximately 7.09, 14.03, and 14.22 degrees 2θ. 31. The solid form of claim 30, wherein the solid form is Form A crystal form characterized by an XRPD pattern comprising peaks at approximately 15.09, 15.94, and 22.30 degrees 2θ. 32. The solid form of claim 31, further comprises peaks at approximately 17.65, 22.47, and 26.77 degrees 2θ. 33. The solid form of claim 31, wherein the solid form is Form A crystal form characterized by an XRPD diffraction pattern which matches the XRPD diffraction pattern presented in FIG. 36. 34. The solid form of claim 31, which exhibits a thermal event, as characterized by DSC, with a peak temperature of about 261° C. and an onset temperature of about 256° C. 35. The solid form of claim 31, which exhibits a weight loss of about 0.16% of the total sample weight upon heating from about 25 to about 120° C. 36. The solid form of claim 30, wherein the solid form is Form B crystal form characterized by an XRPD pattern comprising peaks at approximately 7.11, 14.20, and 20.71 degrees 2θ. 37. The solid form of claim 36, further comprises peaks at approximately 9.93 and 21.36 degrees 2θ. 38. The solid form of claim 36, wherein the solid form is Form B crystal form characterized by an XRPD diffraction pattern which matches the XRPD diffraction pattern presented in FIG. 44. 39. The solid form of claim 30, wherein the solid form is Form C crystal form characterized by an XRPD pattern comprising peaks at approximately 6.55, 13.14, and 13.37 degrees 2θ. 40. The solid form of claim 39, further comprises peaks at approximately 9.09, 19.62, and 19.80 degrees 2θ. 41. The solid form of claim 39, wherein the solid form is Form C crystal form characterized by an XRPD diffraction pattern which matches the XRPD diffraction pattern presented in FIG. 50. 42. The solid form of claim 30, wherein the solid form is Form D crystal form characterized by an XRPD pattern comprising peaks at approximately 13.52, 14.16, and 25.00 degrees 2θ. 43. The solid form of claim 42, further comprises peaks at approximately 6.82, 8.07, and 15.71 degrees 2θ. 44. The solid form of claim 42, wherein the solid form is Form D crystal form characterized by an XRPD diffraction pattern which matches the XRPD diffraction pattern presented in FIG. 57. 45. The solid form of claim 30, wherein the solid form is Form E crystal form characterized by an XRPD pattern comprising peaks at approximately 9.82, 17.06, and 17.73 degrees 2θ. 46. The solid form of claim 45, further comprises peaks at approximately 16.05, 25.71, and 26.15 degrees 2θ. 47. The solid form of claim 45, wherein the solid form is Form E crystal form characterized by an XRPD diffraction pattern which matches the XRPD diffraction pattern presented in FIG. 64. 48. The solid form of claim 30, wherein the solid form is Form F crystal form characterized by an XRPD pattern comprising peaks at approximately 13.71, 14.22, and 20.87 degrees 2θ. 49. The solid form of claim 48, further comprises peaks at approximately 7.10, 16.35, and 28.36 degrees 2θ. 50. The solid form of claim 48, wherein the solid form is Form F crystal form characterized by an XRPD diffraction pattern which matches the XRPD diffraction pattern presented in FIG. 73. 51. The solid form of claim 30, wherein the solid form is Form G crystal form characterized by an XRPD pattern comprising peaks at approximately 6.85, 20.20, and 20.60 degrees 2θ. 52. The solid form of claim 51, further comprises peaks at approximately 9.56, 13.69, 19.05, and 23.57 degrees 2θ. 53. The solid form of claim 51, wherein the solid form is Form G crystal form characterized by an XRPD diffraction pattern which matches the XRPD diffraction pattern presented in FIG. 82. 54. The solid form of claim 30, wherein the solid form is Form H crystal form characterized by an XRPD pattern comprising peaks at approximately 6.83, 20.19, and 20.58 degrees 2θ. 55. The solid form of claim 54, further comprises peaks at approximately 9.47 and 13.63 degrees 2θ. 56. The solid form of claim 54, wherein the solid form is Form H crystal form characterized by an XRPD diffraction pattern which matches the XRPD diffraction pattern presented in FIG. 86. 57. The solid form of claim 30, wherein the solid form is Form I crystal form characterized by an XRPD pattern comprising peaks at approximately 13.95, 23.39, and 24.10 degrees 2θ. 58. The solid form of claim 57, further comprises peaks at approximately 13.51 and 24.30 degrees 2θ. 59. The solid form of claim 57, wherein the solid form is Form I crystal form characterized by an XRPD diffraction pattern which matches the XRPD diffraction pattern presented in FIG. 90. 60. The solid form of claim 30, wherein the solid form is Form J crystal form characterized by an XRPD pattern comprising peaks at approximately 4.86, 13.48, and 20.06 degrees 2θ. 61. The solid form of claim 60, further comprises peaks at approximately 20.39, 22.15, and 23.45 degrees 2θ. 62. The solid form of claim 60, wherein the solid form is Form J crystal form characterized by an XRPD diffraction pattern which matches the XRPD diffraction pattern presented in FIG. 92. 63. The solid form of claim 30, wherein the solid form is Form K crystal form characterized by an XRPD pattern comprising peaks at approximately 7.09, 14.03, and 14.22 degrees 2θ. 64. The solid form of claim 63, further comprises peaks at approximately 9.35 and 21.60 degrees 2θ. 65. The solid form of claim 63, wherein the solid form is Form K crystal form characterized by an XRPD diffraction pattern which matches the XRPD diffraction pattern presented in FIG. 95. 66. The solid form of claim 2, comprising racemic Compound (I) having an XRPD pattern comprising peaks at approximately 4.95, 8.96, and 14.83 degrees 2θ. 67. The solid form of claim 66, further comprises peaks at approximately 12.67, 14.30, 20.09, and 26.57 degrees 2θ. 68. The solid form of claim 66, comprising racemic Compound (I), wherein the solid form is characterized by an XRPD diffraction pattern which matches the XRPD pattern presented in FIG. 97. 69. The solid form of claim 2, comprising racemic Compound (I) and water having an XRPD pattern comprising peaks at approximately 14.01, 17.28, and 26.21 degrees 2θ. 70. The solid form of claim 69, further comprises peaks at approximately 8.34, 11.79, and 17.01 degrees 2θ. 71. The solid form of claim 69, comprising racemic Compound (I) and water, wherein the solid form is characterized by an XRPD diffraction pattern which matches the XRPD pattern presented in FIG. 99. 72. The solid form of claim 2, comprising a HCl salt of racemic Compound (I) and water having an XRPD pattern comprising peaks at approximately 13.88, 14.30, and 15.36 degrees 2θ. 73. The solid form of claim 72, further comprises peaks at approximately 9.84, 16.42, and 19.82 degrees 2θ. 74. The solid form of claim 72, comprising a HCl salt of racemic Compound (I) and water, wherein the solid form is characterized by an XRPD diffraction pattern which matches the XRPD pattern presented in FIG. 101. 75. The solid form of claim 2, comprising a HCl salt of racemic Compound (I) and methanol having an XRPD pattern comprising peaks at approximately 12.38, 14.54, and 26.10 degrees 2θ. 76. The solid form of claim 75, further comprises peaks at approximately 15.06, 20.00, and 26.86 degrees 2θ. 77. The solid form of claim 75, comprising a HCl salt of racemic Compound (I) and methanol, wherein the solid form is characterized by an XRPD diffraction pattern which matches the XRPD pattern presented in FIG. 104.