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1. (EP1266658) Use of betulinic acid derivatives for the treatment and prevention of melanoma
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Claims

1. A composition for treating melanoma comprising betulinic acid modified at the C-3 position.
  2. The composition of claim 1 wherein the modified betulinic acid has the structure:

wherein R a is H, C 1-C 16 alkyl, COC 6H 4X, COCH 2Y, CH 2CHCH 2, or CH 2CCR 1, and wherein X is H, F, Cl, Br, I, NO 2, CH 3, or OCH 3, Y is H, F, Cl, Br, or I, and R 1 is H or C 1-C 6 alkyl.
  3. The composition of claim 1 wherein the modified betulinic acid has the structure:

wherein R d is CCR 1, and wherein R 1 is H or C 1-C 6 alkyl.
  4. The composition of claim 1 wherein the modified betulinic acid has the structure:

wherein R e is R 1CO or COC 6H 4X, wherein R 1 is H or C 1-C 6 alkyl, and X is H, F, Cl, Br, I, NO 2, CH 3, or OCH 3.
  5. A composition for treating melanoma comprising betulinic acid modified at the C-28 position.
  6. The composition of claim 5 wherein the modified betulinic acid has the structure:

   or

wherein R f is C 1-C 10 alkyl, phenyl, C 6H 4X, or CH 2CCR 1, wherein X is H, F, Cl, Br, I, NO 2, CH 3, or OCH 3, and R 1 is H or C 1-C 6 alkyl.
  7. The composition of claim 5 wherein the modified betulinic acid has the structure:

   or

wherein R g is H, C 1-C 6 alkyl, or C 6H 4X, R h is C 1-C 16 alkyl or C 6H 4X, and wherein X is H, F, Cl, Br, I, NO 2, CH 3, or OCH 3.
  8. The composition of claim 5 wherein the modified betulinic acid has the structure:

wherein R i is H, C 1-C 16 alkyl, COC 6H 4X, COCH 2Y, CH 2CHCH 2, or CH 2CCR 1, and wherein X is H, F, Cl, Br, I, NO 2, CH 3, or OCH 3, and R 1 is H or C 1-C 6 alkyl.
  9. The composition of claim 5 wherein the modified betulinic acid has the structure:

wherein R j is CCR 1, and wherein R 1 is H or C 1-C 6 alkyl.
  10. A composition for treating melanoma comprising betulinic acid modified at the C-20 position.
  11. The composition of claim 10 wherein the modified betulinic acid has the structure:


  12. The composition of claim 10 wherein the modified betulinic acid has the structure:

wherein R k is H, C 1-C 16 alkyl, COC 6H 4X, COCH 2Y, CH 2CHCH 2, CH 2CCR 1, and wherein X is H, F, Cl, Br, I, NO 2, CH 3, or OCH 3, Y is H, F, Cl, Br, or I, and R 1 is H or C 1-C 6 alkyl.
  13. The composition of claim 10 wherein the modified betulinic acid has the structure:

wherein R 1 is C 1-C 16 alkyl, C 6H 4X, COC 6H 4X, COCH 2Y, CH 2CHCH 2, or CH 2CCR 1, and wherein X is H, F, Cl, Br, I, NO 2, CH 3, or OCH 3, Y is H, F, Cl, Br, or I, and R 1 is H or C 1-C 16 alkyl.
  14. The composition of claim 10 wherein the modified betulinic acid has the structure:

wherein R m is CCR 1, and R 1 is H or C 1-C 6 alkyl.
  15. The composition of claim 10 wherein the modified betulinic acid has the structure:

wherein R n is H, C 1-C 16 alkyl, CH 2CCR 1, CH 3CO, or COC 6H 4X, and wherein R 1 is H or C 1-C 6 alkyl, and X is H, F, Cl, Br, I, NO 2, CH 3, or OCH 3.
  16. A composition for treating melanoma comprising a compound having a structure:

wherein R 1 is selected from the group consisting of O, HO-N, CH 3O-N, H 2N, HO, and C 6H 4CO 2, R 2 is selected from the group consisting of CHO, CO 2H, CHNOCH 3, CHNOH, and CH 2OH, and R 3 is C(CH 3) 3 or CH 2=C(CH 3) 2.
  17. A method of inhibiting growth of a melanoma comprising topically applying a therapeutically effective amount of the composition of claim 1 to the melanoma.
  18. A method of inhibiting growth of a melanoma comprising topically applying a therapeutically effective amount of the composition of claim 5 to the melanoma.
  19. A method of inhibiting growth of a melanoma comprising topically applying a therapeutically effective amount of the composition of claim 10 to the melanoma.
  20. A method of inhibiting growth of a melanoma comprising topically applying a therapeutically effective amount of the composition of claim 16 to the melanoma.
  21. A method of preventing melanoma comprising topically applying a composition of claim 1 to skin.
  22. A method of preventing melanoma comprising topically applying a composition of claim 5 to skin.
  23. A method of preventing melanoma comprising topically applying a composition of claim 10 to skin.
  24. A method of preventing melanoma comprising topically applying a composition of claim 16 to skin.
  25. A method of preventing melanoma comprising topically applying betulinic acid to skin.