Claims
- 1. A compound of formula I whereinW is SO2; X is O, SOn or NR11; Y is CR12; Z is CR13; m and x are each independently 0 or an integer of 1, 2 or 3; R1 is halogen, CN, OR14, CO2R15, CONR16R17, CNR18NR19R20, SO2NR21R22, SOpR23 or a C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, cycloheteroalkyl, phenyl or heteroaryl group each optionally substituted; R2 is H, CNR24NR25R26 or a C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, cycloheteroalkyl, aryl or heteroaryl group each optionally substituted; R3, R4, R5, R6, R7, R8, R9, R28 and R29 are each independently H or an optionally substituted C1-C6alkyl group; R10 is an optionally substituted C1-C6alkyl, aryl or heteroaryl group; n and p are each independently 0 or an integer of 1 or 2; R11 is H or a C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, cycloheteroalkyl, aryl or heteroaryl group each optionally substituted; R12 and R13 are each independently H, halogen or a C1-C6alkyl, aryl, heteroaryl or C1-C6alkoxy group each optionally substituted; R14 is H, COR27 or a C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, aryl or heteroaryl group each optionally substituted; R15 and R27 are each independently H or a C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, cycloheteroalkyl, aryl or heteroaryl group each optionally substituted; R16, R17, R18, R19, R20, R24, R25 and R26 are each independently H or an optionally substituted C1-C6alkyl group; R21 and R22 are each independently H or a C1-C6alkyl, aryl or heteroaryl group each optionally substituted; and R23 is an optionally substituted C1-C6alkyl, aryl, or heteroaryl group; or the stereoisomers thereof or the pharmaceutically acceptable salts thereof.
- 2. The compound according to claim 1 wherein X is O.
- 3. The compound according to claim 1 wherein X is O and R10 is an optionally substituted aryl or heteroaryl group.
- 4. The compound according to claim 3 selected from the group consisting of:1-(phenylsulfonyl)-4-(piperidin-3-yloxy)-1H-indole; 4-{[4-(piperidin-3-yloxy)-1H-indol-1-yl]sulfonyl}aniline; 1-(1-naphthylsulfonyl)-4-(piperidin-3-yloxy)-1H-indole; 1-(phenylsulfonyl)-4-(piperidin-4-yloxy)-1H-indole; 4-{[4-(piperidin-4-yloxy)-1H-indol-1-yl]sulfonyl}aniline; 1-(1-naphthylsulfonyl)-4-(piperidin-4-yloxy)-1H-indole; the stereoisomers thereof; and the pharmaceutically acceptable salts thereof.
- 5. A pharmaceutical composition which comprises a pharmaceutically acceptable carrier and an effective amount of a compound of formula I whereinW is SO2; X is O, SOn or NR11; Y is CR12; Z is CR13; m and x are each independently 0 or an integer of 1, 2 or 3; R1 is halogen, CN, OR14, CO2R15, CONR16R17, CNR18NR19R20, SO2NR21R22, SOpR23 or a C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, cycloheteroalkyl, phenyl or heteroaryl group each optionally substituted; R2 is H, CNR24NR25R26 or a C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, cycloheteroalkyl, aryl or heteroaryl group each optionally substituted; R3, R4, R5, R6, R7, R8, R9, R28 and R29 are each independently H or an optionally substituted C1-C6alkyl group; R10 is an optionally substituted C1-C6alkyl, aryl or heteroaryl group; n and p are each independently 0 or an integer of 1 or 2; R11 is H or a C1-C6alkyl, C2-C6alkenyl, C2″C6alkynyl, C3-C6cycloalkyl, cycloheteroalkyl, aryl or heteroaryl group each optionally substituted; R12 and R13 are each independently H, halogen or a C1-C6alkyl, aryl, heteroaryl or C1-C6alkoxy group each optionally substituted; R14 is H, COR27 or a C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, aryl or heteroaryl group each optionally substituted; R15 and R27 are each independently H or a C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, cycloheteroalkyl, aryl or heteroaryl group each optionally substituted; R16, R17, R18, R19, R20, R24, R25 and R26 are each independently H or an optionally substituted C1-C6alkyl group; R21 and R22 are each independently H or a C1-C6alkyl, aryl or heteroaryl group each optionally substituted; and R23 is an optionally substituted C1-C6alkyl, aryl, or heteroaryl group; or the stereoisomers thereof or the pharmaceutically acceptable salts thereof.
- 6. The composition according to claim 5 having a formula I compound wherein X is O.
- 7. The composition according to claim 6 having a formula I compound selected from the group consisting of:1-(phenylsulfonyl)-4-(piperidin-3-yloxy)-1H-indole; 4-{[4-(piperidin-3-yloxy)-1H-indol-1-yl]sulfonyl}aniline; 1-(1-naphthylsulfonyl)-4-(piperidin-3-yloxy)-1H-indole; 1-(phenylsulfonyl)-4-(piperidin-4-yloxy)-1H-indole; 4-{[4-(piperidin-4-yloxy)-1H-indol-1-yl]sulfonyl}aniline; 1-(1-naphthylsulfonyl)-4-(piperidin-4-yloxy)-1H-indole; the stereoisomers thereof; and the pharmaceutically acceptable salts thereof.
Parent Case Info
This application claims priority from copending application Ser. No. 60/285,643, filed on Apr. 20, 2001, the entire disclosure of which is incorporated by reference.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
5037841 |
Schohe et al. |
Aug 1991 |
A |
6100291 |
Slassi et al. |
Aug 2000 |
A |
Foreign Referenced Citations (4)
Number |
Date |
Country |
09-40646 |
Feb 1997 |
JP |
09040646 |
Feb 1997 |
JP |
WO 9850346 |
Nov 1998 |
WO |
WO 0102356 |
Jan 2001 |
WO |
Non-Patent Literature Citations (2)
Entry |
Bru-Magniez et al. “Piperidinylthioinole derivatives . . . ” CA 121:149099 (1994).* |
Branchek et al. “5HT6 receptors as emerging targets for drug discovery” CA 133:98965 (2000). |
Provisional Applications (1)
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Number |
Date |
Country |
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60/285643 |
Apr 2001 |
US |