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Details for Patent: 5,321,018

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Details for Patent: 5,321,018

Title: Use of 1.alpha.-hydroxylated-19-nor-vitamin D compounds to treat psoriasis
Abstract:A novel use for 1.alpha.-hydroxylated-19-nor-vitamin D compounds to treat psoriasis inasmuch as these compounds when administered to humans are converted to a metabolite, such as a 1.alpha.,25-dihydroxylated compound, which metabolite in vitro will cause differentiation in a human cell line.
Inventor(s): DeLuca; Hector F. (Deerfield, WI)
Assignee: Wisconsin Alumni Research Foundation (Madison, WI)
Filing Date:Nov 20, 1992
Application Number:07/987,258
Claims:1. A method for treating psoriasis which comprises administering to a patient an effective amount of a compound of the formula: ##STR9## where X and Y are each selected from the group consisting of hydrogen, acyl, alkylsilyl and alkoxyalkyl, and where U is selected from a side chain of the formula ##STR10## wherein R.sub.1 and R.sub.2 are each selected from the group consisting of alkyl, deuteroalkyl, hydroxyalkyl and fluoroalkyl, or, when taken together represent the group--(CH.sub.2).sub.m --where m is an integer having a value of from 2 to 5, R.sub.3 is selected from the group consisting of hydrogen, deuterium, hydroxy, fluorine, O-acyl, alkyl, hydroxyalkyl and fluoroalkyl, R.sub.6 is selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, hydroxyalkyl and fluoroalkyl, or, R.sub.3 and R.sub.6 taken together represent double-bonded oxygen or double-bonded carbon, R.sub.4 and R.sub.5 are each selected from the group consisting of hydrogen, deuterium, hydroxy, O-acyl, fluorine and alkyl, or, R.sub.4 and R.sub.5 taken together form a carbon-carbon double bond or a carbon-carbon triple bond, and wherein n is an integer having a value of from 1 to 5 and wherein the carbon at any one of positions 20, 22, or 23 in the side chain may be replaced by an O, S, or N atom with the proviso that when n is 1 then R.sub.1 and R.sub.2 must both be methyl.

2. The method of claim 1 wherein said compound is 1.alpha.-hydroxy-19-nor-vitamin D.sub.3.

3. The method of claim 1 wherein said compound is 1.alpha.-hydroxy-19-nor-24,24-difluoro-vitamin D.sub.3.

4. The method of claim 1 wherein said compound is 1.alpha.-hydroxy-19-nor-26,27-hexadeutero-vitamin D.sub.3.

5. The method of claim 1 wherein said compound is 1.alpha.-hydroxy-19-nor-26,27-hexafluorovitamin D.sub.3.

6. The method of claim 1 wherein said compound is 1.alpha.-hydroxy-19-nor-vitamin D.sub.2.

7. The method of claim 1 wherein the compound is 24-homo-1.alpha.-hydroxy-19-nor-22-dehydrovitamin D.sub.3.

8. The method of claim 1 wherein the compound is 24-dihomo-1.alpha.-hydroxy-19-nor-22-dehydrovitamin D.sub.3.

9. The method of claim 1 wherein the compound is 24-trihomo-1.alpha.-hydroxy-19-nor-22-dehydrovitamin D.sub.3.

10. The method of claim 1 wherein the compound is 26,27-dimethyl-24-dihomo-1.alpha.-hydroxy-19-nor-22-dehydrovitamin D.sub.3.

11. The method of claim 1 wherein the compound is 26,27-dimethyl-24-trihomo-1.alpha.-hydroxy-19-nor-22-dehydrovitamin D.sub.3.

12. The method of claim 1 wherein the compound is 26,27-diethyl-24-dihomo-1.alpha.-hydroxy-19-nor-22-dehydrovitamin D.sub.3.

13. The method of claim 1 wherein the compound is 26,27-diethyl-24-trihomo-1.alpha.-hydroxy-19-nor-22-dehydrovitamin D.sub.3.

14. The method of claim 1 wherein the compound is 26,27-dipropyl-24-dihomo-1.alpha.-hydroxy-19-nor-22-dehydrovitamin D.sub.3.

15. The method of claim 1 wherein the compound is 26,27-dipropyl-24-trihomo-1.alpha.-hydroxy-19-nor-22-dehydrovitamin D.sub.3.

16. The method of claim 1 wherein the compound is 24-homo-1.alpha.-hydroxy-19-nor-vitamin D.sub.3.

17. The method of claim 1 wherein the compound is 24-dihomo-1.alpha.-hydroxy-19-nor-vitamin D.sub.3.

18. The method of claim 1 wherein the compound is 24-trihomo-1.alpha.-hydroxy-19-nor-vitamin D.sub.3.

19. The method of claim 1 wherein the compound is 26,27-dimethyl-24-dihomo-1.alpha.-hydroxy-19-nor-vitamin D.sub.3.

20. The method of claim 1 wherein the compound is 26,27-dimethyl-24-trihomo-1.alpha.-hydroxy-19-nor-vitamin D.sub.3.

21. The method of claim 1 wherein the compound is 26,27-diethyl-24-dihomo-1.alpha.hydroxy-19-nor-vitamin D.sub.3.

22. The method of claim 1 wherein the compound is 26,27-diethyl-24-trihomo-1.alpha.-hydroxy-19-nor-vitamin D.sub.3.

23. The method of claim 1 wherein the compound is 26,27-dipropyl-24-dihomo-1.alpha.-hydroxy-19-nor-vitamin D.sub.3.

24. The method of claim 1 wherein the compound is 26,27-dipropyl-24-trihomo-1.alpha.-hydroxy-19-nor-vitamin D.sub.3.

25. The method of claim 1 wherein the compound is 1.alpha.-hydroxy-19-nor-24 epi-vitamin D.sub.2.

26. The method of claim 1 wherein said effective amount comprises about 0.01 .mu.g/day to about 100 .mu.g/day of said compound.

27. A composition for use in the treatment of psoriasis which comprises an effective amount of a compound of the formula: ##STR11## where X and Y are each selected from the group consisting of hydrogen, acyl, alkylsilyl and alkoxyalkyl, and where U is selected from a side chain of the formula ##STR12## wherein R.sub.1 and R.sub.2 are each selected from the group consisting of alkyl, deuteroalkyl, hydroxyalkyl and fluoroalkyl, or, when taken together represent the group--(CH.sub.2).sub.m --where m is an integer having a value of from 2 to 5, R.sub.3 is selected from the group consisting of hydrogen, deuterium, hydroxy, fluorine, O-acyl, alkyl, hydroxyalkyl and fluoroalkyl, R.sub.6 is selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, hydroxyalkyl and fluoroalkyl, or, R.sub.3 and R.sub.6 taken together represent double-bonded oxygen or double-bonded carbon, R.sub.4 and R.sub.5 are each selected from the group consisting of hydrogen, deuterium, hydroxy, O-acyl, fluorine and alkyl, or, R.sub.4 and R.sub.5 taken together form a carbon-carbon double bond or a carbon-carbon triple bond, and wherein n is an integer having a value of from 1 to 5 and wherein the carbon at any one of positions 20, 22, or 23 in the side chain may be replaced by an O, S, or N atom with the proviso that when n is 1 then R.sub.1 and R.sub.2 must both be methyl.

28. The composition of claim 27 wherein said compound is 1.alpha.-hydroxy-19-nor-vitamin D.sub.3.

29. The composition of claim 27 wherein said compound is 1.alpha.-hydroxy-19-nor-24,24-difluoro-vitamin D.sub.3.

30. The composition of claim 27 wherein said compound is 1.alpha.-hydroxy-19-nor-26,27-hexadeutero-vitamin D.sub.3.

31. The composition of claim 27 wherein said compound is 1.alpha.-hydroxy-19-nor-26,27-hexafluorovitamin D.sub.3.

32. The composition of claim 27 wherein said compound is 1.alpha.-hydroxy-19-nor-vitamin D.sub.2.

33. The composition of claim 27 wherein the compound is 24-homo-1.alpha.-hydroxy-19-nor-22-dehydrovitamin D.sub.3.

34. The composition of claim 27 wherein the compound is 24-dihomo-1.alpha.-hydroxy-19-nor-22-dehydrovitamin D.sub.3.

35. The composition of claim 27 wherein the compound is 24-trihomo-1.alpha.-hydroxy-19-nor-22dehydrovitamin D.sub.3.

36. The composition of claim 27 wherein the compound is 26,27-dimethyl-24-dihomo-1.alpha.-hydroxy-19-nor-22-dehydrovitamin D.sub.3.

37. The composition of claim 27 wherein the compound is 26,27-dimethyl-24-trihomo-1.alpha.-hydroxy-19-nor-22-dehydrovitamin D.sub.3.

38. The composition of claim 27 wherein the compound is 26,27-diethyl-24-dihomo-1.alpha.-hydroxy-19-nor-22-dehydrovitamin D.sub.3.

39. The composition of claim 27 wherein the compound is 26,27-diethyl-24-trihomo-1.alpha.-hydroxy-19-nor-22-dehydrovitamin D.sub.3.

40. The composition of claim 27 wherein the compound is 26,27-dipropyl-24-dihomo-1.alpha.-hydroxy-19-nor22-dehydrovitamin D.sub.3.

41. The composition of claim 27 wherein the compound is 26,27-dipropyl-24-trihomo-1.alpha.-hydroxy-19-nor22-dehydrovitamin D.sub.3.

42. The composition of claim 27 wherein the compound is 24-homo-1.alpha.-hydroxy-19-nor-vitamin D.sub.3.

43. The composition of claim 27 wherein the compound is 24-dihomo-1.alpha.-hydroxy-19-nor-vitamin D.sub.3.

44. The composition of claim 27 wherein the compound is 24-trihomo-1.alpha.-hydroxy-19-nor-vitamin D.sub.3.

45. The composition to claim 27 wherein the compound is 26,27-dimethyl-24-dihomo-1.alpha.-hydroxy-19-nor-vitamin D.sub.3.

46. The composition of claim 27 wherein the compound is 26,27-dimethyl-24-trihomo-1.alpha.-hydroxy-19-nor-vitamin D.sub.3.

47. The composition of claim 27 wherein the compound is 26,27-diethyl-24-dihomo-1.alpha.-hydroxy-19-nor-vitamin D.sub.3.

48. The composition of claim 27 wherein the compound is 26,27-diethyl-24-trihomo-1.alpha.-hydroxy-19-nor-vitamin D.sub.3.

49. The composition of claim 27 wherein the compound is 26,27-dipropyl-24-dihomo-1.alpha.-hydroxy-19-nor-vitamin D.sub.3.

50. The composition of claim 27 wherein the compound is 26,27-dipropyl-24-trihomo-1.alpha.-hydroxy-19-nor-vitamin D.sub.3.

51. The composition of claim 27 wherein the compound is 1.alpha.-hydroxy-19-nor-24 epi-vitamin D.sub.2.

52. The composition of claim 27 wherein said effective amount is between about 0.01 .mu.g to about 100 .mu.g per gram of the composition.

53. A method of treating psoriasis which comprises administering to a patient an effective amount of 1.alpha.-hydroxylated-19-nor-vitamin D compound which compound upon administering to humans is converted to a metabolite and said metabolite in vitro will cause differentiation of promelocytes to monocytes in a cell line selected from a group consisting of a U937 cell line, an HL60 cell line and a M1 cell line.
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