Claims
- 1. A compound of the formula: wherein:W represents; X represents O or S; Y represents —C(═O)—, —CH(OH)—, —CH2—, S, SO, or SO2; represents a single or a double bond; n is 1, 2, 3 or 4; R1a, R1b, R1c, R1d, and R2 are each independently H, F, Cl, Br, I, OH, C1-C6alkyl, C1-C6 alkoxy, halo(C1-C6)alkyl, phenyl, NO2, —NR7R8, 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, phenyl, NO2, NH2, or CN; R3 represents H, OH, hydroxy(C1-C6)alkyl, C1-C6 alkyl, or C1-C6 alkoxy; R4 represents 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, 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, phenyl, NO2, NH2, or CN; R5 represents 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, phenyl, NO2, NH2, or CN; 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, phenyl, NO2, NH2, or CN; or C3-C8 cycloalkyl substituted with C1-C4 alkyl; 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, phenyl, NO2, NH2, or CN; or a pharmaceutically acceptable salt 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 1 wherein R2 is H.
- 5. A compound according to claim 1 wherein n is 2.
- 6. A compound according to claim 1 wherein R3 is H.
- 7. A compound according to claim 1 wherein R3 is methyl.
- 8. A compound according to claim 1 wherein R4 is 2-pyridyl.
- 9. A compound according to claim 1 wherein is a double bond.
- 10. A compound according to claim 1 wherein Y is —CO—.
- 11. A compound which is selected from the group consisting of:a) 4-(6-benzo(b)thiophene-1,2,3,6-tetrahydropyridyl)-1-cyclohexyl-2-(2-pyridyl)butan-1-one; b) 4-(5-benzo(b)thiophene-1,2,3,6-tetrahydropyridyl)-1-cyclohexyl-2-(2-pyridyl)butan-1-one; c) 4-(2-benzo(b)thiophene-1,2,3,6-tetrahydropyridyl)-1-cyclohexyl-2-(2-pyridyl)butan-1-one; and d) 4-(3-benzo(b)thiophene-1,2,3,6-tetrahydropyridyl)-1-cyclohexyl-2-(2-pyridyl)butan-1-one; or a pharmaceutically acceptable salt thereof.
- 12. A method of inhibiting the reuptake of serotonin and antagonizing the 5-HT1A receptor which comprises administering to a subject in need of such treatment an effective amount of a compound of the formula: wherein:W represents: X represents O or S; Y represents —C(═O)—, —CH(OH)—, —CH2—, S, SO, or SO2; represents a single or a double bond; n is 1, 2, 3 or 4; R1a, R1b, R1c, R1d, and R2 are each independently H, F, Cl, Br, I, OH, C1-C6 alkyl, C1-C6 alkoxy, halo(C1-C6)alkyl, phenyl, NO2, —NR7R8, 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, phenyl, NO2, NH2, or CN; R3 represents H, OH, hydroxy(C1-C6)alkyl, C1-C6 alkyl, or C1-C6 alkoxy; R4 represents 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, 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, phenyl, NO2, NH2, or CN; R5 represents 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, phenyl, NO2, NH2, or CN; 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, phenyl, NO2, NH2, or CN, or C3-C8 cycloalkyl substituted with C1-C4 alkyl; 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, phenyl, NO2, NH2, or CN; or a pharmaceutically acceptable salt thereof.
- 13. A method of potentiating the action of a serotonin reuptake inhibitor comprising administering to a subject in of such treatment a compound formula: wherein:W represents: X represents O or S; Y represents —C(═O)—, —CH(OH)—, —CH2—, S, SO, or SO2; represents a single or a double bond; n is 1, 2, 3 or 4; R1a, R1b, R1c, R1d, and R2 are each independently H, F, Cl, Br, I, OH, C1-C6 alkyl, C1-C6 alkoxy, halo(C1-C6)alkyl, phenyl, NO2, —NR7R8, 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, phenyl, NO2, NH2, or CN; R3 represents H, OH, hydroxy(C1-C6)alkyl, C1-C6 alkyl, or C1-C6 alkoxy; R4 represents 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, 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, phenyl, NO2, NH2, or CN; R5 represents 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, phenyl, NO2, NH2, or CN; 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, phenyl, NO2, NH2, or CN; or C3-C8 cycloalkyl substituted with C1-C4 alkyl; 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, phenyl, NO2, NH2, or CN; or a pharmaceutically acceptable salt thereof.
- 14. A method of treating depression comprising administering to a subject in need thereof an effective amount of a compound of formula: wherein:W represents: X represents O or S, Y represents —C(═O)—, —CH(OH)—, —CH2—, S, SO, or SO2; represents a single or a double bond; n is 1, 2, 3 or 4; R1a, R1b, R1c, R1d, and R2 are each independently H, F, Cl, Br, I, OH, C1-C6 alkyl, C1-C6 alkoxy, halo(C1-C6)alkyl, phenyl, NO2, —NR7R8, 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, phenyl, NO2, NH2, or CN; R3 represents H, OH, hydroxy(C1-C6)alkyl, C1-C6 alkyl, or C1-C6 alkoxy; R4 represents 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, 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, phenyl, NO2, NH2, or CN; R5 represents 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, phenyl, NO2, NH2, or CN; heterocycle substituted with from 1 to 3 substituents elected from the group consisting of F, Cl, Br, I, OH, C1-C6 alkyl, C1-C6 alkoxy, hydroxy(C1-C6)alkyl, halo(C1-C6)alkyl, phenyl, NO2, NH2, or CN; or C3-C8 cycloalkyl substituted with C1-C4 alkyl; 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, phenyl, NO2, NH2, or CN; or a pharmaceutically acceptable salt thereof.
- 15. A pharmaceutical composition comprising an effective amount of a compound as claimed in claim 1 in combination with a pharmaceutical acceptable carrier, diluent or excipients.
Parent Case Info
This application claims the benefit of Patent Cooperation Treaty Application No. PCT/US00/20824, filed 14 Sep. 2000, and U.S. patent application Ser. No. 60/157,343, filed 29 Sep. 1999, the contents of which are herein incorporated by reference.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
PCT/US00/20824 |
|
WO |
00 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO01/23381 |
4/5/2001 |
WO |
A |
Foreign Referenced Citations (5)
Number |
Date |
Country |
0 812 826 |
Dec 1997 |
EP |
0 982 304 |
Mar 2000 |
EP |
982304 |
Mar 2000 |
EP |
WO 9905140 |
Jul 1998 |
WO |
WO 9905149 |
Apr 1999 |
WO |
Provisional Applications (1)
|
Number |
Date |
Country |
|
60/157343 |
Sep 1999 |
US |