Claims
- 1. A compound of the formula wherein:R1 is selected from the group consisting of ═O, (—OR6, H) and (H,H); R2 is selected from the group consisting of ═O, (H,H), and (H,OH); R3 and R6 are independently selected from the group consisting of —H, —C(═O)R7, —C(═O)OR7, —C(═O)NHR7, and —C(═S)OR7; R4 is selected from the group consisting of ═O and (H,OR6); or R3 and R4 can be taken together to form a bridge of the formula A—C(R8)(R9)—O—B, where A is a bond to the oxygen bonded to the carbon at the 28-position and B is a bond to the carbon at the 30-position; R5 is selected from the group consisting of —H and C1-C4 alkyl; R7 is selected from the group consisting of C1-C10 alkyl, C3-C6 cycloalkyl, phenyl and naphthyl optionally substituted by from one to five members selected from the group consisting of C1-C6 alkyl, phenyl, naphthyl, hydroxyl, C1-C6 alkoxyl, acyloxy, amino, N-acylamino, nitro, cyano and halogen and heterocyclic groups selected from the group consisting of piperidyl, piperidinyl, piperazinyl, pyrimidinyl, pyridazinyl, oxazolyl, furyl, and thienyl optionally substituted in a manner such that carbon atoms attached to a heteroatom are not directly substituted by a heteroatom, by from one to four members selected from the group consisting of C1-C6 alkyl, phenyl, naphthyl, hydroxyl, C1-C6 alkoxyl, acyloxy, amino, N-acylamino, nitro, and halogen; R8 and R9 are independently selected from the group consisting of H, C1 to C6 alkyl, or R8 and R9 taken together are ═O; provided that: (a) when R4 is ═O, then R2 is (H,OH); and (b) when R1 is (—OH, H), R2 is ═O, R3 is (—H), R4 is (H, OH), then R5 is not —H, and all pharmaceutically acceptable salts, hydrates or solvates thereof.
- 2. A compound of claim 1 where R1 is (H, OH).
- 3. A compound of claim 1 where R2 is (H, OH).
- 4. A compound of claim 1 where R3 is H.
- 5. A compound of claim 1 where R4 is selected from the group consisting of ═O and (H, OH).
- 6. A compound of claim 1 where R5 is H.
- 7. The compound of claim 1 wherein:(a) R1 is (H,OH), R2 is (H,OH), R3 is —H, R4 is (H,OH), and R5 is —H; (b) R1 is (H,OH), R2 is (H,OH), R3 is —H, R4 is ═O, and R5 is —H; (c) R1 is (H,OH), R2 is (H, OH), R3 is H, R4 is (H,OH), and R5 is —CH3; or (d) R1 is (H, OH), R2 is (H,H), R3 is H, R4 is (H, OH), and R5 is H.
- 8. A pharmaceutical composition comprising a pharmaceutically acceptable carrier or diluent, and an effective therapeutic or prophylatic amount of one or more compounds of claim 1.
- 9. A pharmaceutical composition comprising a pharmaceutically acceptable carrier or diluent and an effective therapeutic or prophylactic amount of one or more compounds of claim 2.
- 10. A pharmaceutical composition comprising a pharmaceutically acceptable carrier or diluent and an effective therapeutic or prophylactic amount of one or more compounds of claim 3.
- 11. A pharmaceutical composition comprising a pharmaceutically acceptable carrier or diluent and an effective therapeutic or prophylactic amount of one or more compounds of claim 4.
- 12. A pharmaceutical composition comprising a pharmaceutically acceptable carrier or diluent and an effective therapeutic or prophylactic amount of a compound of claim 5.
- 13. A pharmaceutical composition comprising a pharmaceutically acceptable carrier or diluent and an effective therapeutic or prophylactic amount of a compound of claim 6.
- 14. A pharmaceutical composition comprising a pharmaceutically acceptable carrier or diluent and an effective therapeutic or prophylactic amount of a compound of claim 720.
- 15. A method of inhibiting the growth of pathogenic fungi in a human or other animal in need thereof which comprises administering to such human or other animal an effective, non-toxic amount of a compound of claim 1.
- 16. A method of inducing immunosuppression in a human or other animal in need thereof which comprises administering to such human or other animal an effective, non-toxic amount of a compound of claim 1.
- 17. A method of treating carcinogenic tumors in a human or other animal comprising administering to such human or animal an effective, non-toxic amount of a compound of claim 1.
- 18. A method of preparing a compound of claim 1 wherein R4 is (H,OH) comprising contacting a compound of the formula wherein:R1 is selected from the group consisting of ═O, (—OR6, H) and (H,H); R2 is selected from the group consisting of ═O, (H,H), and (H,OH); R3 and R6 are independently selected from the group consisting of —H, —C(═O)R7, —C(═O)OR7, —C(═O)NHR7, and —C(═S)OR7; R5 is selected from the group consisting of —H and C1-C4 alkyl; R7 is selected from the group consisting of C1-C10 alkyl, C3-C6 cycloalkyl, phenyl and naphthyl optionally substituted by from one to five members selected from the group consisting of C1-C6 alkyl, phenyl, naphthyl, hydroxyl, C1-C6 alkoxyl, acyloxy, amino, N-acylamino, nitro, cyano and halogen and heterocyclic groups selected from the group consisting of piperidyl, piperidinyl, piperazinyl, pyrimidinyl, pyridazinyl, oxazolyl, furyl, and thienyl optionally substituted in a manner such that carbon atoms attached to a heteroatom are not directly substituted by a heteroatom, by from one to four members selected from the group consisting of C1-C6 alkyl, phenyl, naphthyl, hydroxyl, C1-C6 alkoxyl, acyloxy, amino, N-acylamino, nitro, and halogen; R8 and R9 are independently selected from the group consisting of H, C1 to C6 alkyl, or R8 and R9 taken together are ═O; with a mixture of cerium trichloride and sodium cyanoborohydride.
- 19. A compound of claim 1 wherein R3 and R4 taken together form a bridge of the formula A—C(R8)(R9)—O—B, where A is a bond to the oxygen bonded to the carbon at the 28-position and B is a bond to the carbon at the 30-position; and R8 and R9 are independently selected from the group consisting of H, and C1 to C6 alkyl, or R8 and R9 taken together are ═O.
- 20. A compound of claim 1 wherein:(a) R1 is (H, OH), R2 is (H, OH), R3 is —H, R4 is (H, OH), and R5 is —H; (b) R1 is (H, OH), R2 is (H, OCH3), R3 is H, R4 is (H, OH), and R5 is H; (c) R1 is (H, OH), R2 is ═O, R3 and R4 are —C—C(CH3)2—O—, and R5 is H; (d) R1 is (H, OH), R2 is (H, H), R3 is H, R4 is (H, OH), and R5 is H; (e) R1 is (H, OH), R2 is ═O, R3 and R4 are —C—C(O)O—, and R5 is H; or (f) R1 is (H, OH), R2 is (H, OH), R3 is H, R4 is (H, OH), and R5 is —CH3.
Parent Case Info
This application is a 371 of PCT/US98/06679, filed 16, Jul. 1993, which claims priority of U.S. application 07/915,145, filed 17 Jul. 1992.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
102e Date |
371c Date |
PCT/US93/06679 |
|
WO |
00 |
3/15/1995 |
3/15/1995 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO94/02485 |
2/3/1994 |
WO |
A |
US Referenced Citations (20)
Foreign Referenced Citations (2)
Number |
Date |
Country |
WO 9316189 |
Aug 1993 |
WO |
WO 9409010 |
Apr 1994 |
WO |
Non-Patent Literature Citations (2)
Entry |
Carey et al., “Part B: Reactions and Synthesis”, (1983), Advanced Organic Chemistry, pp. 199-213. |
Carey et al., “Reactions, Mechanisms, and Structure”, (1985), Advanced Organic Chemistry, pp. 691-699 and pp. 809-814. |
Divisions (1)
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Number |
Date |
Country |
Parent |
08/373181 |
Jul 1993 |
US |
Child |
09/359496 |
|
US |
Reissues (1)
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Number |
Date |
Country |
Parent |
08/373181 |
Jul 1993 |
US |
Child |
09/359496 |
|
US |