Claims
- 1. A method for treating alopecia or promoting hair growth in an animal, which comprises administering to said animal an effective amount of an N-linked sulfonamide of a heterocyclic thioester.
- 2. The method of claim 1, wherein the N-linked sulfonamide is non-immunosuppressive.
- 3. The method of claim 1, wherein the N-linked sulfonamide has an affinity for an FKBP-type immunophilin.
- 4. The method of claim 3, wherein the FKBP-type immunophilin is FKBP-12.
- 5. The method of claim 1, wherein the N-linked sulfonamide is a compound of formula I
- 6. The method of claim 5, wherein the mono- or bicyclic, carbo- or heterocyclic ring is selected from the group consisting of phenyl, benzyl, naphthyl, indolyl, pyridyl, pyrrolyl, pyrrolidinyl, pyridinyl, pyrimidinyl, purinyl, quinolinyl, isoquinolinyl, furyl, fluorenyl, thiophenyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, and thienyl.
- 7. The method of claim 5, wherein:
A and B are taken together, with the nitrogen and carbon atoms to which they are respectively attached, to form a 6 membered saturated or unsaturated heterocyclic ring; and R2 is C4-C7 branched chain alkyl, C4-C7 cycloalkyl, phenyl, or 3,4,5-trimethoxyphenyl.
- 8. The method of claim 5, wherein the compound is selected from the group consisting of:
3-(para-Methoxyphenyl)-1-propylmercaptyl (2S)-N-(benzenesulfonyl)pyrrolidine-2-carboxylate; 3-(para-Methoxyphenyl)-1-propylmercaptyl (2S)-N-(α-toluenesulfonyl)pyrrolidine-2-carboxylate; 3-(para-Methoxyphenyl)-1-propylmercaptyl (2S)-N-(α-toluenesulfonyl)pyrrolidine-2-carboxylate; 1,5-Diphenyl-3-pentylmercaptyl N-(para-toluenesulfonyl)pipecolate; and pharmaceutically acceptable salts, esters, and solvates thereof.
- 9. The method of claim 1, wherein the N-linked sulfonamide is a compound of formula II
- 10. The method of claim 9, wherein the mono- or bicyclic, carbo- or heterocyclic ring is selected from the group consisting of phenyl, benzyl, naphthyl, indolyl, pyridyl, pyrrolyl, pyrrolidinyl, pyridinyl, pyrimidinyl, purinyl, quinolinyl, isoquinolinyl, furyl, fluorenyl, thiophenyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, and thienyl.
- 11. The method of claim 1, wherein the N-linked sulfonamide is a compound of formula III
- 12. The method of claim 11, wherein the mono- or bicyclic, carbo- or heterocyclic ring is selected from the group consisting of phenyl, benzyl, naphthyl, indolyl, pyridyl, pyrrolyl, pyrrolidinyl, pyridinyl, pyrimidinyl, purinyl, quinolinyl, isoquinolinyl, furyl, fluorenyl, thiophenyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, and thienyl.
- 13. The method of claim 1, wherein the N-linked sulfonamide is a compound of formula IV
- 14. The method of claim 13, wherein the mono- or bicyclic, carbo- or heterocyclic ring is selected from the group consisting of phenyl, benzyl, naphthyl, indolyl, pyridyl, pyrrolyl, pyrrolidinyl, pyridinyl, pyrimidinyl, purinyl, quinolinyl, isoquinolinyl, furyl, fluorenyl, thiophenyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, and thienyl.
- 15. The method of claim 1, wherein the N-linked sulfonamide is a compound of formula V
- 16. A pharmaceutical composition which comprises:
(i) an effective amount of an N-linked sulfonamide of a heterocyclic thioester for treating alopecia or promoting hair growth in an animal; and (ii) a pharmaceutically acceptable carrier.
- 17. The pharmaceutical composition of claim 16, wherein the N-linked sulfonamide is non-immunosuppressive.
- 18. The pharmaceutical composition of claim 16, wherein the N-linked sulfonamide has an affinity for an FKBP-type immunophilin.
- 19. The pharmaceutical composition of claim 18, wherein the FOP-type immunophilin is FKBP-12.
- 20. The pharmaceutical composition of claim 16, wherein the N-linked sulfonamide is a compound of formula I
- 21. The pharmaceutical composition of claim 20, wherein the mono- or bicyclic, carbo- or heterocyclic ring is selected from the group consisting of phenyl, benzyl, naphthyl, indolyl, pyridyl, pyrrolyl, pyrrolidinyl, pyridinyl, pyrimidinyl, purinyl, quinolinyl, isoquinolinyl, furyl, fluorenyl, thiophenyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, and thienyl.
- 22. The pharmaceutical composition of claim 21, wherein:
A and B are taken together, with the nitrogen and carbon atoms to which they are respectively attached, to form a 6 membered saturated or unsaturated heterocyclic ring; and R2 is C4-C7 branched chain alkyl, C4-C7 cycloalkyl, phenyl, or 3,4,5-trimethoxyphenyl.
- 23. The pharmaceutical composition of claim 20, wherein the compound is selected from the group consisting of:
3-(para-Methoxyphenyl)-1-propylmercaptyl (2S)-N-(benzenesulfonyl)pyrrolidine-2-carboxylate; 3-(para-Methoxyphenyl)-1-propylmercaptyl (2S)-N-(α-toluenesulfonyl)pyrrolidine-2-carboxylate; 3-(para-Methoxyphenyl)-i-propylmercaptyl (2S)-N-(α-toluenesulfonyl)pyrrolidine-2-carboxylate; 1,5-Diphenyl-3-pentylmercaptyl N-(para-toluenesulfonyl)pipecolate; and pharmaceutically acceptable salts, esters, and solvates thereof.
- 24. The pharmaceutical composition of claim 16, wherein the N-linked sulfonamide is a compound of formula II
- 25. The pharmaceutical composition of claim 24, wherein the mono- or bicyclic, carbo- or heterocyclic ring is selected from the group consisting of phenyl, benzyl, naphthyl, indolyl, pyridyl, pyrrolyl, pyrrolidinyl, pyridinyl, pyrimidinyl, purinyl, quinolinyl, isoquinolinyl, furyl, fluorenyl, thiophenyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, and thienyl.
- 26. The pharmaceutical composition of claim 16, wherein the N-linked sulfonamide is a compound of formula III
- 27. The pharmaceutical composition of claim 26, wherein the mono- or bicyclic, carbo- or heterocyclic ring is selected from the group consisting of phenyl, benzyl, naphthyl, indolyl, pyridyl, pyrrolyl, pyrrolidinyl, pyridinyl, pyrimidinyl, purinyl, quinolinyl, isoquinolinyl, furyl, fluorenyl, thiophenyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, and thienyl.
- 28. The pharmaceutical composition of claim 16, wherein the N-linked sulfonamide is a compound of formula IV
- 29. The pharmaceutical composition of claim 28, wherein the mono- or bicyclic, carbo- or heterocyclic ring is selected from the group consisting of phenyl, benzyl, naphthyl, indolyl, pyridyl, pyrrolyl, pyrrolidinyl, pyridinyl, pyrimidinyl, purinyl, quinolinyl, isoquinolinyl, furyl, fluorenyl, thiophenyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, and thienyl.
- 30. The pharmaceutical composition of claim 16, wherein the N-linked sulfonamide is a compound of formula V
Parent Case Info
[0001] This application is a continuation-in-part of U.S. patent application Ser. No. 08/869,426, filed on Jun. 4, 1997, the entire contents of which are herein incorporated by reference.
Divisions (2)
|
Number |
Date |
Country |
Parent |
09359709 |
Jul 1999 |
US |
Child |
09781426 |
Feb 2001 |
US |
Parent |
09089375 |
Jun 1998 |
US |
Child |
09359709 |
Jul 1999 |
US |