Crystalline salt of 2-phenyl-2-aminocyclohexane-1-one derivative
Patent Information
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- GILGAMESH PHARMACEUTICALS INC
- Filing Date
- 2024-06-05
- Publication Date
- 2026-06-17
Smart Images
Figure 2026519697000056 
Figure 2026519697000057 
Figure 2026519697000058
Abstract
Claims
1. Crystalline salts of (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one, including crystalline (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one hydrochloride, crystalline (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one sulfate, crystalline (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one p-toluenesulfonate, crystalline (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one methanesulfonate, and crystalline (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one maleic acid A crystalline salt comprising a salt, crystalline (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one phosphate, crystalline (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one tartrate, crystalline (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one fumarate, crystalline (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one citrate, crystalline (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one malate, or crystalline (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one hippurate.
2. The crystalline salt according to claim 1, wherein the crystalline salt is (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one hydrochloride.
3. The crystalline salt according to claim 2, which is crystalline (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one hydrochloride form 1.
4. The crystalline salt according to claim 3, characterized by a powder X-ray diffraction pattern including peaks at 9.7, 15.0, and 18.6 ± 0.5° 2θ.
5. The crystalline salt according to claim 3, characterized by a powder X-ray diffraction pattern including peaks at 9.7, 13.1, 15.0, 18.6, and 24.2 ± 0.5° 2θ.
6. The crystalline salt according to claim 3, characterized by a powder X-ray diffraction pattern including peaks at 9.7, 13.1, 14.6, 15.0, 18.6, 19.2, 22.5, 24.2, 25.1, and 31.6 ± 0.5° 2θ.
7. 9.7, 12.8, 13.1, 14.3, 14.6, 15.0, 15.7, 17.1, 18.6, 19.2, 19.5, 22.4, 22.5, 23.1, 23.8, 24.2, 24.4, 25.1, 25.3, 25.7, 26.3, 26.6, 27.1, 27.4, 28.8, 29.6, 30.1, 30.5 The crystalline salt according to claim 3, characterized by a powder X-ray diffraction pattern including peaks at 30.9, 31.6, 32.1, 33.1, 33.7, 34.0, 34.3, 34.6, 35.0, 35.3, 35.8, 36.3, 36.5, 36.9, 37.6, 37.9, 38.0, and 38.8 ± 0.5° 2θ.
8. The crystalline salt according to claim 3, characterized in substantially by the powder X-ray diffraction pattern shown in Figure 2.
9. The crystalline salt according to any one of claims 3 to 8, characterized by a DSC thermogram having at least one endothermic peak at approximately 238°C.
10. A crystalline salt according to any one of claims 3 to 9, characterized substantially by the DSC thermogram shown in Figure 4.
11. The crystalline salt according to claim 2, which is crystalline (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one hydrochloride form 2.
12. The crystalline salt according to claim 11, characterized by a powder X-ray diffraction pattern including peaks at 13.2, 15.0, and 24.0 ± 0.5° 2θ.
13. The crystalline salt according to claim 11, characterized by a powder X-ray diffraction pattern including peaks at 13.2, 15.0, 18.4, 18.7, and 24.0 ± 0.5° 2θ.
14. The crystalline salt according to claim 11, characterized by a powder X-ray diffraction pattern including peaks at 13.0, 13.2, 15.0, 17.2, 18.4, 18.7, 24.0, 26.9, 27.1, and 31.1 ± 0.5° 2θ.
15. The crystalline salt according to claim 11, characterized substantially by the powder X-ray diffraction pattern shown in Figure 7.
16. The crystalline salt according to claim 1, wherein the crystalline salt is (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one sulfate.
17. The crystalline salt according to claim 16, wherein the crystalline salt is (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one sulfate-1.
18. The crystalline salt according to claim 17, characterized by a powder X-ray diffraction pattern including peaks at 10.2, 16.0, and 17.6 ± 0.5° 2θ.
19. The crystalline salt according to claim 17, characterized by a powder X-ray diffraction pattern including peaks at 10.2, 16.0, 16.4, 17.6, and 22.7±0.5°2θ.
20. The crystalline salt according to claim 17, characterized by a powder X-ray diffraction pattern including peaks at 7.5, 10.2, 16.0, 16.4, 17.6, 18.5, 19.4, 22.4, 22.6, and 22.7 ± 0.5° 2θ.
21. 7.5, 10.2, 11.8, 12.2, 13.6, 13.7, 14.8, 14.9, 16.0, 16.4, 17.3, 17.6, 18.5, 19.4, 19.5, 19.7, 20.6, 21.0, 21.5, 22.1, 22.4, 22.6, 22.7, 22.9, 23.0, 23.8, 24.4, 25.0, 25.5, 25.9, 26 The crystalline salt according to claim 17, characterized by a powder X-ray diffraction pattern including peaks at 0.6, 27.3, 27.8, 28.7, 28.9, 29.3, 29.7, 30.2, 30.5, 30.8, 31.1, 32.2, 32.6, 32.8, 33.0, 33.5, 33.9, 34.3, 34.5, 38.2, and 39.1 ± 0.5° 2θ.
22. The crystalline salt according to claim 17, characterized in substantially by the powder X-ray diffraction pattern shown in Figure 8.
23. The crystalline salt according to any one of claims 17 to 22, characterized by a DSC thermogram having at least one endothermic peak at approximately 221.3°C.
24. The crystalline salt according to any one of claims 17 to 23, characterized by a DSC thermogram having at least two endothermic peaks at approximately 136.9°C and approximately 221.3°C.
25. A crystalline salt according to any one of claims 17 to 24, characterized substantially by the DSC thermogram shown in Figure 9.
26. The crystalline salt according to claim 16, wherein the crystalline salt is (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one sulfate-3.
27. The crystalline salt according to claim 26, characterized by a powder X-ray diffraction pattern including peaks at 11.9, 16.0, and 18.7 ± 0.5° 2θ.
28. The crystalline salt according to claim 26, characterized by a powder X-ray diffraction pattern including peaks at 10.2, 11.9, 16.0, 17.6, and 18.7 ± 0.5° 2θ.
29. The crystalline salt according to claim 26, characterized by a powder X-ray diffraction pattern including peaks at 7.1, 7.7, 8.5, 10.2, 11.9, 16.0, 17.6, 18.5, 18.7, and 22.7 ± 0.5° 2θ.
30. 7.1, 7.5, 7.7, 8.5, 10.2, 10.5, 11.9, 12.2, 13.1, 15.5, 16.0, 16.4, 17.6, 17.7, 18.1, 18.5, 18.7, 19.4, 19.7, 20.1, 20.7, 21.0, 21.2, 21.5, 22.1, 22.5, 22.7, 23.0, 23.5, 23. The crystalline salt according to claim 26, characterized by a powder X-ray diffraction pattern including peaks at 8, 24.3, 24.9, 25.5, 26.2, 26.7, 27.5, 27.8, 28.4, 28.7, 29.0, 29.3, 29.8, 30.3, 30.8, 31.2, 32.7, 33.7, 34.6, and 38.0 ± 0.5° 2θ.
31. The crystalline salt according to claim 26, characterized substantially by the powder X-ray diffraction pattern shown in Figure 11.
32. The crystalline salt according to claim 16, wherein the crystalline salt is (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one sulfate-4.
33. The crystalline salt according to claim 32, characterized by a powder X-ray diffraction pattern including peaks at 7.9, 16.0, and 17.6 ± 0.5° 2θ.
34. The crystalline salt according to claim 32, characterized by a powder X-ray diffraction pattern including peaks at 7.9, 10.2, 16.0, 17.6, and 22.7±0.5°2θ.
35. The crystalline salt according to claim 32, characterized by a powder X-ray diffraction pattern including peaks at 4.6, 7.9, 10.2, 16.0, 16.4, 16.6, 17.6, 19.4, 21.1, and 22.7 ± 0.5° 2θ.
36. The crystalline salt according to claim 32, characterized by a powder X-ray diffraction pattern including peaks at 4.6, 7.5, 7.9, 9.6, 10.2, 11.6, 12.2, 13.8, 14.8, 16.0, 16.4, 16.6, 17.6, 18.4, 19.4, 19.6, 20.8, 21.1, 21.5, 21.7, 22.1, 22.5, 22.7, 23.0, 23.8, 24.4, 25.0, 25.5, 25.8, 26.3, 27.8, 28.2, 28.9, 30.2, 31.2, 32.6, and 33.9 ± 0.5° 2θ.
37. The crystalline salt according to claim 32, characterized in substantially by the powder X-ray diffraction pattern shown in Figure 12.
38. The crystalline salt according to claim 1, wherein (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one p-toluenesulfonate.
39. The crystalline salt according to claim 38, wherein (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one p-toluenesulfonate-1.
40. The crystalline salt according to claim 39, characterized by a powder X-ray diffraction pattern including peaks at 6.6, 10.6, and 19.5 ± 0.5° 2θ.
41. The crystalline salt according to claim 39, characterized by a powder X-ray diffraction pattern including peaks at 6.6, 10.6, 13.3, 14.6, and 19.5 ± 0.5° 2θ.
42. The crystalline salt according to claim 39, characterized by a powder X-ray diffraction pattern including peaks at 6.6, 10.6, 13.3, 14.6, 19.5, 20.2, 22.4, 26.2, 26.3, and 26.7 ± 0.5° 2θ.
43. The crystalline salt according to claim 39, characterized by a powder X-ray diffraction pattern including peaks at 2.1, 5.9, 6.6, 10.6, 12.0, 13.3, 14.6, 16.7, 17.4, 17.8, 19.5, 19.9, 20.2, 20.4, 21.3, 21.9, 22.4, 22.6, 23.8, 24.6, 25.5, 26.2, 26.3, 26.7, 28.2, 28.5, 28.9, 30.4, 31.0, 31.8, 32.4, 32.9, 33.4, 33.5, 35.1, 36.5, 38.0, and 39.5 ± 0.5° 2θ.
44. The crystalline salt according to claim 39, characterized in substantially by the powder X-ray diffraction pattern shown in Figure 13.
45. The crystalline salt according to any one of claims 39 to 44, characterized by a DSC thermogram having at least one endothermic peak at approximately 156.9°C.
46. The crystalline salt according to any one of claims 39 to 45, characterized by a DSC thermogram having at least two endothermic peaks at approximately 158.9°C and approximately 172.3°C.
47. A crystalline salt according to any one of claims 39 to 46, characterized substantially by the DSC thermogram shown in Figure 14.
48. The crystalline salt according to claim 38, wherein (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one p-toluenesulfonate-2B.
49. The crystalline salt according to claim 48, characterized by a powder X-ray diffraction pattern including peaks at 5.4, 19.6, and 21.6 ± 0.5° 2θ.
50. The crystalline salt according to claim 48, characterized by a powder X-ray diffraction pattern including peaks at 5.4, 10.7, 16.1, 19.6, and 21.6 ± 0.5° 2θ.
51. The crystalline salt according to claim 48, characterized by a powder X-ray diffraction pattern including peaks at 5.4, 6.0, 10.5, 10.7, 13.2, 14.7, 16.1, 19.0, 19.3, 19.6, 20.1, 20.8, 21.6, 23.2, 23.4, 24.0, 26.7, 26.8, 27.1, 34.1, and 38.2 ± 0.5° 2θ.
52. The crystalline salt according to claim 48, characterized in substantially by the powder X-ray diffraction pattern shown in Figure 16.
53. The crystalline salt according to any one of claims 48 to 51, characterized by a DSC thermogram having at least one endothermic peak at approximately 168.7°C.
54. The crystalline salt according to any one of claims 48 to 52, characterized by a DSC thermogram having at least two endothermic peaks at approximately 168.7°C and approximately 117.3°C or approximately 70.7°C.
55. The crystalline salt according to any one of claims 48 to 53, characterized by a DSC thermogram having at least three endothermic peaks at approximately 168.7°C, approximately 117.3°C, and approximately 70.7°C.
56. A crystalline salt according to any one of claims 48 to 54, characterized substantially by the DSC thermogram shown in Figure 17.
57. The crystalline salt according to claim 1, wherein the crystalline salt is (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one methanesulfonate.
58. The crystalline salt according to claim 57, characterized by a powder X-ray diffraction pattern including peaks at 10.1, 15.7, and 16.9 ± 0.5° 2θ.
59. The crystalline salt according to claim 57, characterized by a powder X-ray diffraction pattern including peaks at 10.1, 15.7, 16.9, 22.2, and 22.6 ± 0.5° 2θ.
60. The crystalline salt according to claim 57, characterized by a powder X-ray diffraction pattern including peaks at 10.1, 13.4, 15.7, 16.9, 17.4, 18.8, 20.4, 22.2, 22.6, and 22.7±0.5°2θ.
61. 10.1, 10.9, 11.8, 12.8, 13.4, 15.0, 15.7, 16.9, 17.4, 17.7, 18.0, 18.8, 19.1, 20.4, 20.8, 21.2, 22.2, 22.4, 22.6, 22.7, 23.3, 24.5, 24.6, 24.9, 25.2, 25.7, 26.0, 26.5, 26.9, 27.3, 2 The crystalline salt according to claim 57, characterized by a powder X-ray diffraction pattern including peaks at 7.5, 28.4, 28.6, 29.6, 30.3, 30.6, 30.8, 31.1, 31.6, 31.8, 32.3, 32.4, 33.5, 34.5, 35.2, 35.4, 35.9, 36.3, 37.3, 38.3, and 39.9 ± 0.5° 2θ.
62. The crystalline salt according to claim 57, characterized substantially by the powder X-ray diffraction pattern shown in Figure 18.
63. The crystalline salt according to any one of claims 57 to 62, characterized by a DSC thermogram having at least one endothermic peak at approximately 228.3°C.
64. A crystalline salt according to any one of claims 57 to 63, characterized substantially by the DSC thermogram shown in Figure 19.
65. The crystalline salt according to claim 1, wherein the salt is crystalline (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one maleate.
66. The crystalline salt according to claim 65, wherein the crystalline salt is (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one maleate-1.
67. The crystalline salt according to claim 66, characterized by a powder X-ray diffraction pattern including peaks at 16.2, 19.4, and 24.6 ± 0.5° 2θ.
68. The crystalline salt according to claim 66, characterized by a powder X-ray diffraction pattern including peaks at 14.3, 16.2, 19.4, 24.6, and 24.7 ± 0.5° 2θ.
69. The crystalline salt according to claim 66, characterized by a powder X-ray diffraction pattern including peaks at 14.3, 16.2, 18.6, 19.4, 20.5, 21.4, 23.8, 24.6, 24.7, and 31.8 ± 0.5° 2θ.
70. The crystalline salt according to claim 66, characterized by a powder X-ray diffraction pattern including peaks at 13.2, 14.3, 15.0, 15.2, 16.2, 17.0, 17.5, 18.6, 19.4, 20.5, 21.4, 21.9, 23.8, 24.6, 24.7, 25.5, 25.7, 26.3, 26.7, 27.3, 28.0, 29.2, 29.3, 30.7, 31.6, 31.8, 31.9, 32.2, 32.7, 33.1, 33.6, 34.5, 34.6, 34.8, 35.7, 36.0, 36.8, 37.3, 37.4, 38.5, and 39.3 ± 0.5° 2θ.
71. The crystalline salt according to claim 66, characterized in substantially by the powder X-ray diffraction pattern shown in Figure 20.
72. The crystalline salt according to any one of claims 66 to 71, characterized by a DSC thermogram having at least one endothermic peak at approximately 202.0°C.
73. A crystalline salt according to any one of claims 66 to 72, characterized substantially by the DSC thermogram shown in Figure 21.
74. The crystalline salt according to claim 65, wherein the crystalline salt is (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one maleate-2.
75. The crystalline salt according to claim 74, characterized by a powder X-ray diffraction pattern including peaks at 13.3, 16.0, and 18.8 ± 0.5° 2θ.
76. The crystalline salt according to claim 74, characterized by a powder X-ray diffraction pattern including peaks at 13.3, 14.7, 16.0, 18.8, and 19.2 ± 0.5° 2θ.
77. The crystalline salt according to claim 74, characterized by a powder X-ray diffraction pattern including peaks at 13.3, 14.7, 16.0, 18.0, 18.6, 18.8, 19.2, 20.5, 22.6, and 24.1 ± 0.5° 2θ.
78. 9.3, 11.2, 13.3, 13.5, 14.7, 15.0, 16.0, 16.5, 18.0, 18.6, 18.8, 19.2, 20.5, 21.1, 21.9, 22.6, 23.2, 24.1, 24.4, 24.9, 25.3, 25.5, 26.7, 26.9, 27.0, 27.2, 28.1, 28.5, 29.3, 29.8 The crystalline salt according to claim 74, characterized by a powder X-ray diffraction pattern including peaks at 29.9, 30.3, 30.7, 31.3, 31.5, 31.9, 32.1, 32.4, 33.3, 33.8, 34.0, 34.6, 35.0, 35.3, 35.6, 36.0, 36.7, 37.3, 37.7, and 38.1 ± 0.5° 2θ.
79. The crystalline salt according to claim 74, characterized in substantially by the powder X-ray diffraction pattern shown in Figure 22.
80. The crystalline salt according to any one of claims 74 to 79, characterized by a DSC thermogram having at least one endothermic peak at approximately 198.2°C.
81. A crystalline salt according to any one of claims 74 to 80, characterized substantially by the DSC thermogram shown in Figure 23.
82. The crystalline salt according to claim 1, wherein the crystalline salt is (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one phosphate.
83. The crystalline salt according to claim 82, wherein the crystalline salt is (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-ion phosphate-1.
84. The crystalline salt according to claim 83, characterized by a powder X-ray diffraction pattern including peaks at 6.6, 19.1, 21.0, and 24.1 ± 0.5° 2θ.
85. The crystalline salt according to claim 83, characterized by a powder X-ray diffraction pattern including peaks at 6.6, 15.1, 19.1, 21.0, and 24.1 ± 0.5° 2θ.
86. The crystalline salt according to claim 83, characterized by a powder X-ray diffraction pattern including peaks at 6.6, 13.4, 15.1, 19.1, 21.0, 22.8, 23.2, 24.1, 27.0, and 27.8 ± 0.5° 2θ.
87. The crystalline salt according to claim 83, characterized by a powder X-ray diffraction pattern including peaks at 6.6, 11.5, 13.4, 14.7, 15.1, 15.6, 17.2, 18.1, 19.1, 20.0, 20.8, 21.0, 21.5, 22.8, 23.2, 24.1, 24.3, 25.2, 26.8, 27.0, 27.8, 28.5, 29.3, 29.7, 30.1, 31.4, 31.6, 32.1, 32.8, 33.0, 33.5, 34.0, 34.6, 36.0, 36.6, 36.9, 38.7, 39.0, and 39.6±0.5°2θ.
88. The crystalline salt according to claim 83, characterized in substantially by the powder X-ray diffraction pattern shown in Figure 24.
89. The crystalline salt according to any one of claims 83 to 88, characterized by a DSC thermogram having at least one endothermic peak at approximately 236.0°C.
90. A crystalline salt according to any one of claims 83 to 89, characterized substantially by the DSC thermogram shown in Figure 25.
91. The crystalline salt according to claim 82, wherein the crystalline salt is (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-ion phosphate-2.
92. The crystalline salt according to claim 91, characterized by a powder X-ray diffraction pattern including peaks at 6.6, 21.0, 24.1, and 33.5 ± 0.5° 2θ.
93. The crystalline salt according to claim 91, characterized by a powder X-ray diffraction pattern including peaks at 6.6, 13.4, 21.0, 24.1, and 33.5 ± 0.5° 2θ.
94. The crystalline salt according to claim 91, characterized by a powder X-ray diffraction pattern including peaks at 6.6, 7.1, 13.4, 19.1, 21.0, 24.1, 26.67, 26.75, 26.9, and 33.5±0.5°2θ.
95. The crystalline salt according to claim 91, characterized by a powder X-ray diffraction pattern including peaks at 3.5, 6.6, 7.1, 13.4, 14.7, 15.1, 15.6, 17.2, 18.1, 19.1, 19.9, 21.0, 22.7, 23.2, 24.1, 25.2, 26.67, 26.75, 26.9, 27.1, 27.7, 28.4, 29.2, 29.7, 30.1, 30.4, 31.4, 31.6, 33.5, 34.6, 35.9, 36.9, and 39.6 ± 0.5° 2θ.
96. The crystalline salt according to claim 91, characterized in substantially by the powder X-ray diffraction pattern shown in Figure 26.
97. The crystalline salt according to any one of claims 91 to 96, characterized by a DSC thermogram having at least one endothermic peak at approximately 224.6°C.
98. A crystalline salt according to any one of claims 91 to 97, characterized substantially by the DSC thermogram shown in Figure 27.
99. The crystalline salt according to claim 1, wherein the crystalline salt is (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one tartrate.
100. The crystalline salt according to claim 99, wherein the crystalline salt is (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one tartrate-1.
101. The crystalline salt according to claim 100, characterized by a powder X-ray diffraction pattern including peaks at 8.9, 15.7, and 19.2 ± 0.5° 2θ.
102. The crystalline salt according to claim 100, characterized by a powder X-ray diffraction pattern including peaks at 8.9, 15.5, 15.7, 17.5, and 19.2 ± 0.5° 2θ.
103. The crystalline salt according to claim 100, characterized by a powder X-ray diffraction pattern including peaks at 8.9, 11.8, 15.5, 15.7, 17.5, 17.8, 19.2, 23.0, 26.9, and 27.1 ± 0.5° 2θ.
104. The crystalline salt according to claim 100, characterized by a powder X-ray diffraction pattern including peaks at 8.9, 11.1, 11.8, 12.4, 12.7, 13.0, 14.2, 15.5, 15.7, 17.5, 17.8, 19.2, 19.8, 20.3, 20.8, 23.0, 23.6, 24.8, 25.6, 26.1, 26.9, 27.1, 28.7, 28.9, 29.3, 29.8, 30.2, 30.4, 31.0, 31.3, 33.7, and 36.2 ± 0.5° 2θ.
105. The crystalline salt according to claim 100, characterized in substantially by the powder X-ray diffraction pattern shown in Figure 28.
106. The crystalline salt according to claim 99, wherein the crystalline salt is (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one tartrate-5.
107. The crystalline salt according to claim 106, characterized by a powder X-ray diffraction pattern including peaks at 16.6, 19.0, and 21.7 ± 0.5° 2θ.
108. The crystalline salt according to claim 106, characterized by a powder X-ray diffraction pattern including peaks at 9.3, 14.3, 16.6, 19.0, and 21.7 ± 0.5° 2θ.
109. The crystalline salt according to claim 106, characterized by a powder X-ray diffraction pattern including peaks at 9.3, 12.0, 12.4, 14.3, 15.1, 16.6, 19.0, 21.7, and 28.9 ± 0.5° 2θ.
110. The crystalline salt according to claim 106, characterized in substantially by the powder X-ray diffraction pattern shown in Figure 30.
111. The crystalline salt according to any one of claims 106 to 110, characterized by a DSC thermogram having at least one endothermic peak having a peak at approximately 163.5°C or approximately 187.2°C.
112. The crystalline salt according to any one of claims 106 to 111, characterized by a DSC thermogram having at least two endothermic peaks at approximately 163.5°C and approximately 187.2°C.
113. A crystalline salt according to any one of claims 106 to 112, characterized substantially by the DSC thermogram shown in Figure 31.
114. The crystalline salt according to claim 99, wherein the crystalline salt is (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one tartrate-3.
115. The crystalline salt according to claim 114, characterized by a powder X-ray diffraction pattern including peaks at 16.8, 18.8, and 19.4 ± 0.5° 2θ.
116. The crystalline salt according to claim 114, characterized by a powder X-ray diffraction pattern including peaks at 7.6, 16.8, 18.8, 19.4, and 20.9 ± 0.5° 2θ.
117. The crystalline salt according to claim 114, characterized by a powder X-ray diffraction pattern including peaks at 7.6, 12.2, 13.4, 16.8, 18.8, 19.2, 19.4, 19.9, 20.9, and 23.1 ± 0.5° 2θ.
118. The crystalline salt according to claim 114, characterized by a powder X-ray diffraction pattern including peaks at 7.6, 12.2, 13.4, 15.0, 16.8, 18.8, 19.2, 19.4, 19.9, 20.7, 20.9, 22.3, 22.8, 23.1, 23.5, 24.5, 26.2, 27.0, 28.0, 28.6, 29.6, 30.0, 31.3, 32.0, 32.27, 32.29, 32.5, 33.4, 34.1, and 36.0 ± 0.5° 2θ.
119. The crystalline salt according to claim 114, characterized in substantially by the powder X-ray diffraction pattern shown in Figure 32.
120. The crystalline salt according to any one of claims 114 to 119, characterized by a DSC thermogram having at least one endothermic peak at approximately 176.6°C.
121. The crystalline salt according to any one of claims 114 to 119, characterized by a DSC thermogram having at least two endothermic peaks at approximately 176.6°C and approximately 110.1°C.
122. A crystalline salt according to any one of claims 114 to 121, characterized substantially by the DSC thermogram shown in Figure 33.
123. The crystalline salt according to claim 99, wherein the crystalline salt is (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one tartrate-6.
124. The crystalline salt according to claim 123, characterized by a powder X-ray diffraction pattern including peaks at 6.6, 13.1, and 14.5 ± 0.5° 2θ.
125. The crystalline salt according to claim 123, characterized by a powder X-ray diffraction pattern including peaks at 6.6, 13.1, 14.5, 15.2, and 24.1 ± 0.5° 2θ.
126. The crystalline salt according to claim 123, characterized by a powder X-ray diffraction pattern including peaks at 6.6, 13.1, 14.2, 14.5, 15.2, 16.8, 20.2, 20.8, 23.3, and 24.1 ± 0.5° 2θ.
127. The crystalline salt according to claim 123, characterized by a powder X-ray diffraction pattern including peaks at 6.4, 6.6, 13.1, 14.2, 14.5, 15.2, 16.0, 16.8, 17.1, 17.2, 17.5, 18.1, 18.5, 19.2, 19.5, 20.0, 20.2, 20.8, 21.1, 21.4, 21.6, 21.8, 23.3, 23.5, 24.1, 25.2, 26.0, 26.3, 26.7, 27.0, 27.3, 27.8, 28.3, 28.7, 29.0, 29.9, 30.2, 31.2, 31.6, 32.0, and 32.9 ± 0.5° 2θ.
128. The crystalline salt according to claim 123, characterized in substantially by the powder X-ray diffraction pattern shown in Figure 35.
129. The crystalline salt according to any one of claims 123 to 128, characterized by a DSC thermogram having at least one endothermic peak at approximately 61.7°C.
130. The crystalline salt according to any one of claims 123 to 129, characterized by a DSC thermogram having at least two endothermic peaks at approximately 61.7°C and approximately 199.8°C.
131. A crystalline salt according to any one of claims 123 to 130, characterized substantially by the DSC thermogram shown in Figure 36.
132. The crystalline salt according to claim 1, wherein the crystalline salt is (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-on fumarate.
133. The crystalline salt according to claim 132, wherein the crystalline salt is (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-on fumarate-1.
134. The crystalline salt according to claim 133, characterized by a powder X-ray diffraction pattern including peaks at 14.8, 24.8, and 25.7 ± 0.5° 2θ.
135. The crystalline salt according to claim 133, characterized by a powder X-ray diffraction pattern including peaks at 7.4, 9.1, 14.8, 24.8, and 25.7 ± 0.5° 2θ.
136. The crystalline salt according to claim 133, characterized by a powder X-ray diffraction pattern including peaks at 7.4, 9.1, 12.3, 14.8, 16.3, 18.3, 19.5, 23.8, 24.8, and 25.7 ± 0.5° 2θ.
137. The crystalline salt according to claim 133, characterized by a powder X-ray diffraction pattern including peaks at 6.2, 7.4, 9.1, 11.4, 12.3, 13.4, 14.0, 14.8, 15.1, 16.3, 16.7, 16.9, 17.8, 18.3, 19.1, 19.5, 20.8, 21.0, 22.7, 23.8, 24.4, 24.8, 25.0, 25.5, 25.7, 27.0, 27.4, 27.5, 29.7, 31.1, 31.9, 33.9, 34.0, 35.0, and 38.3 ± 0.5° 2θ.
138. The crystalline salt according to claim 133, characterized substantially by the powder X-ray diffraction pattern shown in Figure 37.
139. The crystalline salt according to any one of claims 133 to 138, characterized by a DSC thermogram having at least one endothermic peak at approximately 181.7°C.
140. A crystalline salt according to any one of claims 133 to 139, characterized substantially by the DSC thermogram shown in Figure 38.
141. The crystalline salt according to claim 132, wherein the crystalline salt is (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-on fumarate-2.
142. The crystalline salt according to claim 141, characterized by a powder X-ray diffraction pattern including peaks at 12.4, 16.3, and 22.8 ± 0.5° 2θ.
143. The crystalline salt according to claim 141, characterized by a powder X-ray diffraction pattern including peaks at 12.4, 16.3, 17.7, 22.8, and 24.6 ± 0.5° 2θ.
144. The crystalline salt according to claim 141, characterized by a powder X-ray diffraction pattern including peaks at 12.4, 14.8, 16.3, 17.5, 17.7, 21.4, 22.7, 22.8, 24.6, and 24.8 ± 0.5° 2θ.
145. 6.2, 7.3, 7.4 (7.39), 7.4 (7.45), 9.1, 10.1, 11.3, 12.3, 12.4, 13.5, 13.9, 14.8, 16.3, 16.7, 17.0, 17.5, 17.7, 18.3, 18.9, 19.1, 19.3, 19.5, 19.9, 20.6, 21.4, 22.7, 22.8, 23.0, 23.4, 23.8, 24.6, 24.8, 2 The crystalline salt according to claim 141, characterized by a powder X-ray diffraction pattern including peaks at 5.0, 25.4, 25.7, 26.3, 26.7, 27.1, 27.6, 27.7, 28.0, 28.8, 29.3, 29.8, 31.0, 31.7, 32.7, 32.9, 33.9, 34.1, 34.9, 35.1, 35.4, 36.0, 36.7, and 37.8 ± 0.5° 2θ.
146. The crystalline salt according to claim 141, characterized in substantially by the powder X-ray diffraction pattern shown in Figure 39.
147. The crystalline salt according to claim 1, wherein the crystalline salt is (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-on citrate.
148. The crystalline salt according to claim 147, wherein the crystalline salt is (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-on citrate-2.
149. The crystalline salt according to claim 148, characterized by a powder X-ray diffraction pattern including peaks at 6.6, 14.5, and 17.7 ± 0.5° 2θ.
150. The crystalline salt according to claim 148, characterized by a powder X-ray diffraction pattern including peaks at 6.6, 14.5, 16.3, 17.7, and 17.9 ± 0.5° 2θ.
151. The crystalline salt according to claim 148, characterized by a powder X-ray diffraction pattern including peaks at 6.6, 11.9, 14.5, 15.9, 16.3, 17.7, 17.9, 19.9, 21.2, and 21.9 ± 0.5° 2θ.
152. 6.6, 9.7, 9.8, 11.4, 11.9, 13.6, 14.5, 15.1, 15.9, 16.3, 17.3, 17.7, 17.9, 18.1, 18.5, 18.8, 19.7, 19.9, 21.2, 21.8, 21.9, 22.9, 23.3, 23.9, 24.1, 24.3, 24.7, 26.4, 2 The crystalline salt according to claim 148, characterized by a powder X-ray diffraction pattern including peaks at 7.3, 27.6, 28.3, 28.6, 29.3, 29.7, 30.1, 30.8, 31.1, 31.3, 31.5, 32.0, 32.6, 35.6, 36.1, 36.8, 37.8, and 38.9 ± 0.5° 2θ.
153. The crystalline salt according to claim 148, characterized substantially by the powder X-ray diffraction pattern shown in Figure 41.
154. The crystalline salt according to any one of claims 148 to 153, characterized by a DSC thermogram having at least one endothermic peak at approximately 173.6°C.
155. A crystalline salt according to any one of claims 148 to 154, characterized substantially by the DSC thermogram shown in Figure 42.
156. The crystalline salt according to claim 1, wherein the crystalline salt is (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-onglycolate.
157. The crystalline salt according to claim 156, characterized by a powder X-ray diffraction pattern including peaks at 7.4, 9.6, and 19.2 ± 0.5° 2θ.
158. The crystalline salt according to claim 156, characterized by a powder X-ray diffraction pattern including peaks at 7.4, 9.6, 19.2, 22.2, and 29.8 ± 0.5° 2θ.
159. The crystalline salt according to claim 156, characterized by a powder X-ray diffraction pattern including peaks at 7.4, 9.6, 14.8, 16.1, 19.2, 21.5, 22.2, 22.3, 29.8, and 29.9 ± 0.5° 2θ.
160. 7.4, 9.6, 12.8, 13.3, 14.4, 14.8, 16.1, 16.5, 16.7, 18.7, 19.2, 19.6, 20.2, 21.5, 22.2, 22.3, 22.5, 22.7, 23.0 (22.97), 23.0 (23.04), 23.5, 25.7, 25.8, 26.8, 27.5, 28.1, 2 The crystalline salt according to claim 156, characterized by a powder X-ray diffraction pattern including peaks at 8.8, 28.9, 29.8, 29.9, 30.9, 31.8, 31.9, 32.4, 32.5, 33.7, 34.5, 34.7, 35.0, 36.2, 36.3, 37.5, 37.6, 38.9, and 39.0 ± 0.5° 2θ.
161. The crystalline salt according to claim 156, characterized in substantially by the powder X-ray diffraction pattern shown in Figure 43.
162. The crystalline salt according to any one of claims 156 to 161, characterized by a DSC thermogram having at least one endothermic peak at approximately 118.5°C.
163. A crystalline salt according to any one of claims 156 to 162, characterized substantially by the DSC thermogram shown in Figure 44.
164. The crystalline salt according to claim 1, wherein the crystalline salt is (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one malate.
165. The crystalline salt according to claim 164, characterized by a powder X-ray diffraction pattern including peaks at 13.4, 15.8, and 18.5 ± 0.5° 2θ.
166. The crystalline salt according to claim 164, characterized by a powder X-ray diffraction pattern including peaks at 13.4, 14.7, 15.8, 18.5, and 19.4 ± 0.5° 2θ.
167. The crystalline salt according to claim 164, characterized by a powder X-ray diffraction pattern including peaks at 11.2, 13.4, 14.7, 15.8, 18.5, 19.4, 22.4, 29.7, 31.3, and 31.9 ± 0.5° 2θ.
168. The crystalline salt according to claim 164, characterized by a powder X-ray diffraction pattern including peaks at 11.2, 12.1, 13.4, 14.7, 15.3, 15.8, 16.5, 17.6, 18.5, 18.9, 19.4, 20.9, 22.4, 23.6, 24.4, 24.9, 26.7, 26.9, 28.6, 29.4, 29.7, 31.3, 31.9, 33.2, 34.3, 35.7, 36.1, and 37.5 ± 0.5° 2θ.
169. The crystalline salt according to claim 164, characterized in substantially by the powder X-ray diffraction pattern shown in Figure 45.
170. The crystalline salt according to any one of claims 164 to 169, characterized by a DSC thermogram having at least one endothermic peak having a peak at approximately 196.3°C or approximately 126.0°C.
171. The crystalline salt according to any one of claims 164 to 170, characterized by a DSC thermogram having at least two endothermic peaks at approximately 196.3°C and approximately 126.0°C.
172. A crystalline salt according to any one of claims 164 to 171, characterized substantially by the DSC thermogram shown in Figure 46.
173. The crystalline salt according to claim 1, wherein the crystalline salt is (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one hippurate.
174. The crystalline salt according to claim 173, characterized by a powder X-ray diffraction pattern including peaks at 6.2, 8.6, and 12.5 ± 0.5° 2θ.
175. The crystalline salt according to claim 173, characterized by a powder X-ray diffraction pattern including peaks at 6.2, 8.6, 12.5, 18.7, and 20.9 ± 0.5° 2θ.
176. The crystalline salt according to claim 173, characterized by a powder X-ray diffraction pattern including peaks at 6.2, 8.6, 12.5, 13.0, 17.3, 18.7, 19.1, 20.2, 20.9, and 21.0 ± 0.5° 2θ.
177. 6.2, 8.6, 12.5, 13.0, 13.8, 15.1, 16.0, 17.3, 18.7, 18.9, 19.1, 19.7, 19.8, 20.2, 20.9, 21.0, 21.4, 21.9, 22.2, 22.4, 23.5, 24.0, 24.5, 25.0, 25.8, 26.2, 26.3, 27.0, The crystalline salt according to claim 173, characterized by a powder X-ray diffraction pattern including peaks at 27.9, 28.2, 29.1, 30.4, 30.8, 31.0, 31.7, 32.5, 33.1, 33.2, 33.7, 33.9, 34.2, 35.2, 35.7, 36.5, 38.0, and 38.4 ± 0.5° 2θ.
178. The crystalline salt according to claim 173, characterized in substantially by the powder X-ray diffraction pattern shown in Figure 47.
179. The crystalline salt according to any one of claims 173 to 178, characterized by a DSC thermogram having at least one endothermic peak at approximately 117.6°C.
180. A crystalline salt according to any one of claims 173 to 179, characterized substantially by the DSC thermogram shown in Figure 48.
181. A solid comprising one or more crystalline salts of (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one as described in claims 1 to 180.
182. The solid according to claim 181, comprising at least 50% by mass of any one of the crystalline salts of (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one.
183. The solid according to claim 181, comprising at least 90% by mass of any one of the crystalline salts of (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one.
184. The solid according to claim 181, comprising at least 95% by mass of any one of the crystalline salts of (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one.
185. The solid according to claim 181, comprising at least 97% by mass of any one of the crystalline salts of (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one.
186. The solid according to claim 181, comprising a mixture of two or more crystalline salts of (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one.
187. A solid comprising a substantially chemically and polymorphically pure form of any one of the crystalline salts of (R)-2-(4-fluorophenyl)-2-(methylamino)cyclohexane-1-one described in any one of claims 1 to 180.
188. A pharmaceutical composition comprising one or more crystalline salts according to any one of claims 1 to 180.
189. A method for treating a mental disorder, comprising the step of administering one or more therapeutically effective amounts of crystalline salts described in any one of claims 1 to 180.