Salt forms of poorly soluble probucol esters and ethers

1. A meglumine salt represented by the formula:

wherein:

R 1 and R 2 are independently hydrogen or alkyl or taken together to form a carbonyl; and

Y is (CH 2 ) 0-5 ; and when R 1 and R 2 taken together form a carbonyl, Y is (CH 2 ) 1-5 .

2. A meglumine salt represented by the formula:

wherein:

Y is (CH 2 ) 1-5 .

3. The salt of claim 2 , wherein Y is (CH 2 ).

4. The salt of claim 2 wherein Y is (CH 2 ) 2 .

5. The salt of claim 2 wherein Y is (CH 2 ) 3 .

6. The salt of claim 2 wherein Y is (CH 2 ) 4 .

7. The salt of claim 2 wherein Y is (CH 2 ) 5 .

8. A meglumine salt represented by the formula:

wherein:

Y is (CH 2 ) 0-5 .

9. The salt of claim 8 , wherein Y is (CH 2 ) 0 .

10. The salt of claim 8 wherein Y is (CH 2 ).

11. The salt of claim 8 wherein Y is (CH 2 ) 2 .

12. The salt of claim 8 wherein Y is (CH 2 ) 3 .

13. The salt of claim 8 wherein Y is (CH 2 ) 4 .

14. The salt of claim 8 wherein Y is (CH 2 ) 5 .

15. A meglumine salt selected from the group consisting of:

butanedioic acid, mono [4-[[1-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1-methylethyl]thio]-2,6-bis(1,1-dimethylethyl)phenyl]ester, meglumine salt; acetic acid, [4-[[1-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1-methyl-ethyl]thio]-2,6-bis(1,1-dimethylethyl)phenoxy]-, meglumine salt; and butanoic acid, 4-[4-[[1-[[3,5-bis(1,1-dimethylethyl)4-hydroxyphenyl]thio]-1-methyl-ethyl]thio]-2,6-bis(1,1-dimethylethyl)phenoxy]-, meglumine salt.

16. A pharmaceutical composition comprising a meglumine salt represented by the formula:

wherein:

R 1 and R 2 are independently hydrogen or alkyl or taken together to form a carbonyl; and

Y is (CH 2 ) 0-5 ; when R 1 and R 2 taken together form a carbonyl, Y is (CH 2 ) 1-5 ;

together with a pharmaceutically acceptable carrier.

17. A pharmaceutical composition comprising a meglumine salt represented by the formula:

wherein:

Y is (CH 2 ) 1-5 ;

together with a pharmaceutically acceptable carrier.

18. The pharmaceutical composition of claim 17 , wherein Y is (CH 2 ).

19. The pharmaceutical composition of claim 17 wherein Y is (CH 2 ) 2 .

20. The pharmaceutical composition of claim 17 wherein Y is (CH 2 ) 3 .

21. The pharmaceutical composition of claim 17 wherein Y is (CH 2 ) 4 .

22. The pharmaceutical composition of claim 17 wherein Y is (CH 2 ) 5 .

23. A pharmaceutical composition comprising a meglumine salt represented by the formula:

wherein:

Y is (CH 2 ) 0-5 ; when R 1 and R 2 taken together form a carbonyl, Y is (CH 2 ) 1-5 ;

together with a pharmaceutically acceptable carrier.

24. The pharmaceutical composition of claim 23 , wherein Y is (CH 2 ) 0 .

25. The pharmaceutical composition of claim 23 wherein Y is (CH 2 ).

26. The pharmaceutical composition of claim 23 wherein Y is (CH 2 ) 1 .

27. The pharmaceutical composition of claim 23 wherein Y is (CH 2 ) 3 .

28. The pharmaceutical composition of claim 23 wherein Y is (CH 2 ) 4 .

29. The pharmaceutical composition of claim 23 wherein Y is (CH 2 ) 5 .

30. A method for the treatment of an inflammatory disorder, comprising administering to a host in need thereof an effective treatment amount of the salt of claim 1 .

31. The method of claim 30 , wherein the inflammatory disorder is arthritis.

32. The method of claim 30 , wherein the inflammatory disorder is rheumatoid arthritis.

33. The method of claim 30 , wherein the inflammatory disorder is osteoarthritis.

34. The method of claim 30 , wherein the inflammatory disorder is asthma.

35. The method of claim 30 , wherein the inflammatory disorder is multiple sclerosis.

36. The method of claim 30 , wherein the inflammatory disorder is psoriasis.

37. A method for the treatment of a cardiovascular disorder, comprising administering to a host in need thereof an effective treatment amount of the salt of claim 1 .

38. The method of claim 37 , wherein the cardiovascular disorder is atherosclerosis.

39. The method of claim 37 , wherein the cardiovascular disorder is postangioplasty restenosis.

40. The method of claim 37 , wherein the cardiovascular disorder is coronary artery disease.

41. The method of claim 37 , wherein the cardiovascular disorder is small artery disease.

42. The method of claim 37 , wherein the cardiovascular disorder is angina.

43. A method for inhibiting expression of VCAM-1, comprising administering to a host in need thereof an effective treatment amount of the salt of claim 1 .

44. A method of treating an immune response, comprising administering to a host in need thereof an effective treatment amount of the salt of claim 1 .

45. The method of claim 44 , wherein the immune response is solid organ transplant rejection.

46. An organic amine salt represented by the formula:

wherein:

R 1 and R 2 are independently hydrogen or alkyl or taken together to form a carbonyl; and

Y is (CH 2 ) 0-5 ; when R 1 and R 2 taken together form a carbonyl, Y is (CH 2 ) 1-5 .

47. An organic amine salt represented by the formula:

wherein:

Y is (CH 2 ) 1-5 .

48. An organic amine salt represented by the formula:

wherein:

Y is (CH 2 ) 0-5 .

49. A method for the treatment of an inflammatory disorder, comprising administering to a host in need thereof an effective treatment amount of the salt of any one of claims 46 - 48 .

50. A method for the treatment of a cardiovascular disorder, comprising administering to a host in need thereof an effective treatment amount of the salt of any one of claims 46 - 48 .

51. A method for inhibiting expression of VCAM-1, comprising administering to a host in need thereof an effective treatment amount of the salt of any one of claims 46 - 48 .

52. A method of treating an immune response, comprising administering to a host in need thereof an effective treatment amount of the salt of any one of claims 46 - 48 .

53. A pharmaceutical composition represented by the formula:

wherein:

R 1 and R 2 are independently hydrogen or alkyl or taken together to form a carbonyl; and

Y is (CH 2 ) 0-5 ; when R 1 and R 2 taken together form a carbonyl, Y is (CH 2 ) 1-5 ;

together with a pharmaceutically acceptable carrier.

54. A pharmaceutical composition represented by the formula:

wherein:

Y is (CH 2 ) 1-5 ;

together with a pharmaceutically acceptable carrier.

55. A pharmaceutical composition represented by the formula:

wherein:

Y is (CH 2 ) 0-5 ; when R 1 and R 2 taken together form a carbonyl, Y is (CH 2 ) 1-5 ;

together with a pharmaceutically acceptable carrier.

56. A method for the treatment of an inflammatory disorder, comprising administering to a host in need thereof an effective treatment amount of the composition of any one of claims 53 - 55 .

57. A method for the treatment of a cardiovascular disorder, comprising administering to a host in need thereof an effective treatment amount of the composition of any one of claims 53 - 55 .

58. A method for inhibiting expression of VCAM-1, comprising administering to a host in need thereof an effective treatment amount of the composition of any one of claims 53 - 55 .

59. A method of treating an immune response, comprising administering to a host in need thereof an effective treatment amount of the composition of any one of claims 53 - 55 .