Claims
- 1. A compound of the formula: wherein:X is O, S, NR, S(═O), or S(═O)2; Y is —C(═O)—, —CH(OH)—, —CH2—, —C(═NOR), CHNR7R, S, SO, or SO2; represents a single or a double bond; n is 1, 2, 3 or 4; R is H or C1-C6 alkyl; R1a, R1b, R1c and R2 are each independently H, F, Cl, Br, I, OH, C1-C6 alkyl, C1-C6 alkoxy, halo(C1-C6)alkyl, (C1-C6)alkylthio, phenyl, NO2, —NR7R8, —C(═O)NR7R8, —NR7C(═O)R8, CN or phenyl substituted with from 1 to 3 substituents selected from the group consisting of F, Cl, Br, I, OH, C1-C6 alkyl, C1-C6 alkoxy, halo(C1-C6)alkyl, (C1-C6)alkylthio, phenyl, NO2, NH2, or CN; R3 is H, OH, hydroxy(C1-C6)alkyl, C1-C6 alkyl, C1-C6 alkoxy, or (C1-C6)alkylthio; R4 is aryl, heterocycle, C3-C8 cycloalkyl, aryl substituted with from 1 to 3 substituents selected from the group consisting of F, Cl, Br, I, OH, C1-C6 alkyl, C1-C6 alkoxy, halo(C1-C6)alkyl, (C1-C6)alkylthio, phenyl, NO2, NH2, or CN; or heterocycle substituted with from 1 to 3 substituents selected from the group consisting of F, Cl, Br, 1, OH, C1-C6 alkyl, C1-C6 alkoxy, halo(C1-C6)alkyl, (C1-C6)alkylthio, phenyl, NO2, NH2, or CN; R5 is aryl, heterocycle, C3-C8 cycloalkyl, aryl substituted with from 1 to 3 substituents selected from the group consisting of F, Cl, Br, I, OH, C1-C6 alkyl, C1-C6 alkoxy, hydroxy(C1-C6)alkyl, halo(C1-C6)alkyl, (C1-C6)alkylthio, phenyl, NO2, NH2, or CN; or heterocycle substituted with from 1 to 3 substituents selected from the group consisting of F, Cl, Br, I, OH, C1-C6 alkyl, C1-C6 alkoxy, hydroxy(C1-C6)alkyl, halo(C1-C6)alkyl, (C1-C8)alkylthio, phenyl, NO2, NH2, or CN; R6a and R6b are each independently H or C1-C3 alkyl; R7 and R8 are each independently H, C1-C6 alkyl, aryl or aryl substituted with from 1 to 3 substituents selected from the group consisting of F, Cl, Br, I, OH, C1-C6 alkyl, C1-C6 alkoxy, halo(C1-C6)alkyl, (C1-C6)alkylthio, phenyl, NO2, NH2, or CN; and the pharmaceutically acceptable salts thereof.
- 2. A compound according to claim 1 wherein X is O.
- 3. A compound according to claim 1 wherein X is S.
- 4. A compound according to claim 2 wherein R2 is H.
- 5. A compound according to claim 3 wherein R2 is H.
- 6. A compound according to claim 4 wherein n is 2.
- 7. A compound according to claim 5 wherein n is 2.
- 8. A compound according to claim 7 wherein R6a and R6b are H.
- 9. A compound according to claim 8 wherein Y is —C(═O)—.
- 10. A compound according to claim 9 wherein R5 is cyclohexyl or phenyl.
- 11. A compound according to claim 10 wherein R3 is H or C1-C6 alkyl.
- 12. A compound according to claim 11 wherein R4 is 2-pyridyl, 3-pyridyl, or phenyl.
- 13. A compound according to claim 12 wherein R1a, R1b and R1c are H.
- 14. A pharmaceutical composition comprising an effective amount of a compound according to claim 1 in combination with a pharmaceutically acceptable carrier, diluent or excipient.
- 15. A method of treating depression comprising administering to a subject in need thereof an effective amount of a compound of formula: wherein:X is O, S, NR, S(═O), or S(═O)2; Y is —C(═O)—, —CH(OH)—, —CH2—, —C(═NOR), CHNR7R, S, SO, or SO2; represents a single or a double bond; n is 1, 2, 3 or 4; R is H or C1-C6 alkyl; R1a, R1b, R1c and R2 are each independently H, F, Cl, Br, I, OH, C1-C6 alkyl, C1-C6 alkoxy, halo(C1-C6)alkyl, (C1-C6)alkylthio, phenyl, NO2, —NR7R8, —C(═O)NR7R8, —NR7C(═O)R8, CN or phenyl substituted with from 1 to 3 substituents selected from the group consisting of F, Cl, Br, I, OH, C1-C6 alkyl, C1-C6 alkoxy, halo(C1-C6)alkyl, (C1-C6)alkylthio, phenyl, NO2, NH2, or CN; R3 is H, OH, hydroxy(C1-C6)alkyl, C1-C6 alkyl, C1-C6 alkoxy, or (C1-C6)alkylthio; R4 is aryl, heterocycle, C3-C8 cycloalkyl, aryl substituted with from 1 to 3 substituents selected from the group consisting of F, Cl, Br, I, OH, C1-C6 alkyl, C1-C6 alkoxy, halo(C1-C8)alkyl, (C1-C6)alkylthio, phenyl, NO2, NH2, or CN; or heterocycle substituted with from 1 to 3 substituents selected from the group consisting of F, Cl, Br, I, OH, C1-C6 alkyl, C1-C6 alkoxy, halo(C1-C6)alkyl, (C1-C6)alkylthio, phenyl, NO2, NH2, or CN; R5 is aryl, heterocycle, C3-C8 cycloalkyl, aryl substituted with from 1 to 3 substituents selected from the group consisting of F, Cl, Br, 1, OH, C1-C6 alkyl, C1-C6 alkoxy, hydroxy(C1-C6)alkyl, halo(C1-C6)alkyl, (C1-C6)alkylthio, phenyl, NO2, NH2, or CN; or heterocycle substituted with from 1 to 3 substituents selected from the group consisting of F, Cl, Br, I, OH, C1-C6 alkyl, C1-C6 alkoxy, hydroxy(C1-C6)alkyl, halo(C1-C6)alkyl, (C1-C6)alkylthio, phenyl, NO2, NH2, or CN; R6a and R6b are each independently H or C1-C3 alkyl; R7 and R8 are each independently H, C1-C6 alkyl, aryl or aryl substituted with from 1 to 3 substituents selected from the group consisting of F, Cl, Br, I, OH, C1-C6 alkyl, C1-C6 alkoxy, halo(C1-C5)alkyl, (C1-C6)alkylthio, phenyl, NO2, NH2, or CN; and the pharmaceutically acceptable salts thereof.
- 16. A compound of the formula: wherein:X is O, S, NR, S(═O), or S(═O)2; represents a single or a double bond; R is H or C1-C6 alkyl; R1a, R1b, R1c and R2 are each independently H, F, Cl, Br, I, OH, C1-C6 alkyl, C1-C6 alkoxy, halo(C1-C6)alkyl, (C1-C6)alkylthio, phenyl, NO2, —NR7R8, —C(═O)NR7R8, —NR7C(═O)R8, CN or phenyl substituted with from 1 to 3 substituents selected from the group consisting of F, Cl, Br, I, OH, C1-C6 alkyl, C1-C6 alkoxy, halo(C1-C6)alkyl, (C1-C6)alkylthio, phenyl, NO2, NH2, or CN; R6a and R6b are each independently H or C1-C3 alkyl; and R7 and R8 are each independently H, C1-C6 alkyl, aryl or aryl substituted with from 1 to 3 substituents selected from the group consisting of F, Cl, Br, I, OH, C1-C6 alkyl, C1-C6 alkoxy, halo(C1-C6)alkyl, (C1-C6)alkylthio, phenyl, NO2, NH2, or CN.
- 17. A compound according to claim 16 wherein X is S.
- 18. A compound according to claim 16 wherein X is O.
- 19. A compound according to claim 16 wherein R2 is H.
Parent Case Info
This application is a national stage entry under 35 U.S.C. §371 of PCT/US99/14778, filed Jun. 29, 1999 which claims the benefit of U.S. Provisional Application No. 60/091,245 filed Jun. 30, 1998.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
PCT/US99/14778 |
|
WO |
00 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO00/00203 |
1/6/2000 |
WO |
A |
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
5585374 |
Cliffe et al. |
Dec 1996 |
A |
Foreign Referenced Citations (2)
Number |
Date |
Country |
WO 0000196 |
Jan 2000 |
WO |
WO 0000198 |
Jan 2000 |
WO |
Provisional Applications (1)
|
Number |
Date |
Country |
|
60/091245 |
Jun 1998 |
US |