Salts of N-[2-({(3R)-1-[trans-4-hydroxy-4-(6-methoxypyridin-3-yl)-cyclohexyl]pyrrolidin-3-yl}amino)-2-oxoethyl]-3-(trifluoromethyl)benzamide

1 . A pharmaceutically acceptable salt of a compound of Formula I:

wherein said salt is a bis(methanesulfonic acid) salt, bis(ethanesulfonic acid) salt, or camphoric acid salt.

2 . The salt of claim 1 wherein said salt is a bis(methanesulfonic acid) salt.

3 . The salt of claim 1 wherein said salt is a bis(ethanesulfonic acid) salt.

4 . The salt of claim 1 wherein said salt is a camphoric acid salt.

5 . The salt of claim 1 wherein said salt is crystalline.

6 . The salt of claim 1 wherein said salt is anhydrous.

7 . The salt of claim 1 , wherein said salt is a bis(methanesulfonic acid) salt having a DSC thermogram substantially as shown in FIG. 1 .

8 . The salt of claim 1 , wherein said salt is a bis(methanesulfonic acid) salt having a DSC endotherm peak at about 166° C.

9 . The salt of claim 1 , wherein said salt is a bis(methanesulfonic acid) salt having an X-ray powder diffraction pattern substantially as shown in FIG. 2 .

10 . The salt of claim 1 , wherein said salt is a bis(methanesulfonic acid) salt having an X-ray powder diffraction pattern comprising peaks, in terms of 2θ, at about 8.7° and about 21.8°.

11 . The salt of claim 1 , wherein said salt is a bis(methanesulfonic acid) salt having an X-ray powder diffraction pattern comprising peaks, in terms of 2θ, at about 8.7°, about 21.8°, about 20.1°, and about 20.9°.

12 . The salt of claim 1 , wherein said salt is a bis(methanesulfonic acid) salt having an X-ray powder diffraction pattern comprising peaks, in terms of 2θ, at about 8.7°, about 21.8°, about 20.1°, about 20.9°, about 22.5°, and about 17.2°.

13 . The salt of claim 1 , wherein said salt is a bis(ethanesulfonic acid) salt having a DSC thermogram substantially as shown in FIG. 3 .

14 . The salt of claim 1 , wherein said salt is a bis(ethanesulfonic acid) salt having a DSC endotherm peak at about 173° C.

15 . The salt of claim 1 , wherein said salt is a bis(methanesulfonic acid) salt having an X-ray powder diffraction pattern substantially as shown in FIG. 4 .

16 . The salt of claim 1 , wherein said salt is a bis(methanesulfonic acid) salt having an X-ray powder diffraction pattern comprising at least one peak, in terms of 2η, at about 9.2°.

17 . The salt of claim 1 , wherein said salt is a bis(methanesulfonic acid) salt having an X-ray powder diffraction pattern comprising peaks, in terms of 2θ, at about 9.20, about 12.1°, and about 18.3°.

18 . The salt of claim 1 , wherein said salt is a bis(methanesulfonic acid) salt having an X-ray powder diffraction pattern comprising peaks, in terms of 2θ, at about 9.20, about 12.1°, about 13.8°, about 18.3°, about 19.3°, and about 19.8°.

19 . The salt of claim 1 , wherein said salt is a camphoric acid salt having a DSC thermogram substantially as shown in FIG. 5 .

20 . The salt of claim 1 , wherein said salt is a bis(ethanesulfonic acid) salt having a DSC endotherm peak at about 176° C.

21 . The salt of claim 1 , wherein said salt is a camphoric acid salt having an X-ray powder diffraction pattern substantially as shown in FIG. 6 .

22 . The salt of claim 1 , wherein said salt is a camphoric acid salt having an X-ray powder diffraction pattern comprising peaks, in terms of 2θ, at about 17.0° and about 19.1°.

23 . The salt of claim 1 , wherein said salt is a camphoric acid salt having an X-ray powder diffraction pattern comprising peaks, in terms of 2θ, at about 17.0°, about 19.1°, about 17.8°, and about 14.1°.

24 . The salt of claim 1 , wherein said salt is a camphoric acid salt having an X-ray powder diffraction pattern comprising peaks, in terms of 2θ, at about 17.0°, about 19.1°, about 17.8°, about 14.1°, about 16.3°, and about 18.4°.

25 . The salt of claim 1 , wherein said salt is a camphoric acid salt having an X-ray powder diffraction pattern comprising peaks, in terms of 2θ, at about 17.0°, about 19.1°, about 17.8°, about 14.1°, about 16.3°, about 18.4°, about 10.1° and about 11.7°.

26 . A method of preparing the salt of claim 1 , wherein said salt is a bis(methanesulfonic acid) salt, comprising:

combining said compound of Formula I with methane sulfonic acid in a crystallizing solvent comprising water, alcohol, and ketone; and

precipitating said salt from said crystallizing solvent.

27 . The method of claim 26 wherein said alcohol comprises isopropanol.

28 . The method of claim 26 wherein said ketone comprises methyl isobutyl ketone.

29 . The method of claim 26 wherein said precipitating is induced by adding ketone to said crystallizing solvent.

30 . The method of claim 26 wherein the volume ratio of water to alcohol in said crystallizing solvent is about 1:2 to about 1:20.

31 . The method of claim 26 wherein the volume ratio of water to alcohol in said crystallizing solvent is about 1:5 to about 1:12.

32 . The method of claim 26 wherein the volume ratio of water to alcohol in said crystallizing solvent is about 1:9.

33 . A salt prepared by the method of claim 26 .

34 . A method of preparing the salt of claim 1 , wherein said salt is a bis(ethanesulfonic acid) salt, comprising:

combining said compound of Formula I with ethane sulfonic acid in a crystallizing solvent comprising an alcohol; and

precipitating said salt from said crystallizing solvent.

35 . The method of claim 34 wherein said alcohol comprises isopropanol.

36 . A salt prepared by the method of claim 34 .

37 . A method of preparing the salt of claim 1 , wherein said salt is a camphoric acid salt, comprising:

combining said compound of Formula I with camphoric acid in a crystallizing solvent comprising ethyl acetate; and

precipitating said salt from said crystallizing solvent.

38 . A salt prepared by the method of claim 37 .

39 . A composition comprising the salt of claim 1 and a pharmaceutically acceptable carrier.

40 . A method of modulating activity of a chemokine receptor comprising contacting said chemokine receptor with a salt of claim 1 .

41 . The method of claim 40 wherein said chemokine receptor is CCR2.

42 . The method of claim 40 wherein said modulating corresponds to inhibiting.

43 . A method of treating a disease associated with expression or activity of a chemokine receptor in a patient comprising administering to said patient a therapeutically effective amount of a salt of claim 1 .

44 . The method of claim 43 wherein said chemokine receptor is CCR2.

45 . The method of claim 43 wherein said disease is an inflammatory disease.

46 . The method of claim 43 wherein said disease is an immune disorder.

47 . The method of claim 43 wherein said disease is rheumatoid arthritis, atherosclerosis, lupus, multiple sclerosis, neuropathic pain, transplant rejection, diabetes, or obesity.

48 . The method of claim 43 wherein said disease is cancer.

49 . The method of claim 48 wherein said cancer is characterized by tumor associated macrophages.

50 . The method of claim 48 wherein said cancer is breast cancer, ovarian cancer or multiple myeloma.

51 . The method of claim 43 further comprising administering an anti-inflammatory agent.

52 . The method of claim 51 wherein said anti-inflammatory agent is an antibody.