Claims
- 1. A compound of general formula I
- 2. The compound of claim 1 wherein
X is O or S; n is 2, 3, 4 or 5; m is 2 or 3; Y represents N or CH; R1 and R1′ are both hydrogen; one or two of R7, R8, R10, R11 and R12 independently are hydrogen, halogen, CF3, CN or C1-6-alkyl; and the remaining of R7, R8, R10, R11 and R12 are hydrogen; R9 is hydrogen; R2, R3, R4, R5 and R6 independently are hydrogen, halogen, C1-6-alkyl, C3-8-cycloalkyl, C1-6-alkoxy, hydroxy, nitro, CN, CF3, OCF3, acyl; NH2, NR13R14 wherein R13 and R14 independently represent hydrogen, C1-6-alkyl, C3-8-cycloalkyl, or phenyl; or R13 and R14 together with the nitrogen forms a piperidine, morpholine, piperazine or pyrrolidine; its enantiomers, and a pharmaceutically acceptable acid addition salt thereof.
- 3. The compound of claim 1 or 2, wherein R1 and R1′ are hydrogen.
- 4. The compound of claim 1 or 2, wherein m is 2.
- 5. The compound of claim 1 or 2, wherein n is 2, 3 or 4.
- 6. The compound of claim 1 or 2, wherein Y is N.
- 7. The compound of claim 1 or 2, wherein at least one of R2, R3, R4, R5 and R6 is halogen.
- 8. The compound of claim 1 or 2, wherein at least two of R2, R3, R4, R5 and R6 are halogen.
- 9. The compound of claim 1 or 2, wherein at least three of R2, R3, R4, R5 and R6 are halogen.
- 10. The compound of claim 1 or 2, wherein R2 and/or R6 are not hydrogen.
- 11. The compound of claim 1 or 2, wherein the indole is attached to the group Y in position 4.
- 12. The compound of claim 1, which is selected from the group consisting of
4-{4-[3-(2-Chloro-phenoxy)-propyl]-piperazin-1-yl}-1H-indole 4-{4-[3-(2-Chloro-phenylsulfanyl)-propyl]-piperazin-1-yl}-1H-indole 4-{4-[3-(2-Bromo-phenylsulfanyl)-propyl]-piperazin-1-yl}-1H-indole 4-{4-[3-(2-Bromo-phenoxy)-propyl]-piperazin-1-yl}-1H-indole 4-{4-[4-(2-Bromo-4-fluoro-phenoxy)-butyl]-piperazin-1-yl}-1H-indole 4-{4-[4-(2-Chloro-6-methyl-phenylsulfanyl)-butyl]-piperazin-1-yl}-1H-indole 4-{4-[2-(2-Chloro-4-fluoro-phenylsulfanyl)-ethyl]-piperazin-1-yl}-1H-indole 4-{4-[2-(2,6-Dichloro-phenylsulfanyl)-ethyl]-piperazin-1-yl}-1H-indole 4-{4-[2-(3,4-Dichloro-phenylsulfanyl)-ethyl]-piperazin-1-yl}-1H-indole 4-{4-[2-(4-Fluoro-phenylsulfanyl)-ethyl]-piperazin-1-yl}-1H-indole 4-{4-[3-(2-Chloro-4-fluoro-phenylsulfanyl)-propyl]-piperazin-1-yl}-1H-indole 4-{4-[4-(2-Bromo-4-fluoro-phenoxy)-butyl]-piperazin-1-yl}-1H-indole 4-{4-[3-(2,4-Difluoro-phenoxy)-propyl]-piperazin-1-yl}-1H-indole 4-{4-[4-(2,6-Dichloro-phenylsulfanyl)-butyl]-piperazin-1-yl}-1H-indole 4-{4-[3-(2-Chloro-4-fluoro-phenoxy)-propyl]-piperazin-1-yl}-1H-indole 4-{4-[4-(2-Chloro-6-methyl-phenylsulfanyl)-butyl]-piperazin-1-yl}-1H-indole 4-{4-[4-(2,6-Dichloro-4-fluoro-phenoxy)-butyl]-piperazin-1-yl}-1H-indole 4-{4-[3-(2-Bromo-4,6-difluoro-phenoxy)-propyl]-piperazin-1-yl}-1H-indole 4-{4-[3-(2,6-Dichloro-4-fluoro-phenoxy)-propyl]-piperazin-1-yl}-1H-indole 4-{4-[4-(4-Bromo-2,6-difluoro-phenoxy)-butyl]-piperazin-1-yl}-1H-indole 4-{4-[4-(2,6-Dibromo-4-fluoro-phenoxy)-butyl]-piperazin-1-yl}-1H-indole 4-{4-[3-(2,4,6-Tribromo-phenoxy)-propyl]-piperazin-1-yl}-1H-indole 4-{4-[3-(4-Bromo-2,6-difluoro-phenoxy)-propyl]-piperazin-1-yl}-1H-indole 1-(3,5-Difluoro-4-{3-[4-(1H-indol-4-yl)-piperazin-1-yl]-propoxy}-phenyl)-propan-1-one 3,5-Dibromo-4-{3-[4-(1H-indol-4-yl)-piperazin-1-yl]-propoxy}-benzonitrile 4-{4-[2-(2-Bromo-4,6-difluoro-phenoxy)-ethyl]-piperazin-1-yl}-1H-indole 4-{4-[3-(2,6-Dichloro-phenylsulfanyl)-propyl]-piperazin-1-yl}-1H-indole 4-{4-[2-(2,6-Dimethyl-phenoxy)-ethyl]-piperazin-1-yl}-1H-indole 4-{4-[4-(2,6-Dimethyl-phenylsulfanyl)-butyl]-piperazin-1-yl}-1H-indole 4-{4-[2-(2,4-Dimethyl-phenylsulfanyl)-ethyl]-piperazin-1-yl}-1H-indole 4-{4-[2-(2,3-Dichloro-phenylsulfanyl)-ethyl]-piperazin-1-yl}-1H-indole 4-{4-[2-(2-Allyl-6-chloro-phenoxy)-ethyl]-piperazin-1-yl}-1H-indole 4-{4-[3-(2-Trifluoromethyl-phenylsulfanyl)-propyl]-piperazin-1-yl}-1H-indole 4-{4-[3-(3,4-Dichloro-phenylsulfanyl)-propyl]-piperazin-1-yl}-1H-indole 4-{4-[4-(2,4-Dimethyl-phenoxy)-butyl]-piperazin-1-yl}-1H-indole 4-{4-[4-(2-Ethyl-phenoxy)-butyl]-piperazin-1-yl}-1H-indole 4-[4-(4-Phenylsulfanyl-butyl)-piperazin-1-yl]-1H-indole 4-{4-[4-(2-Chloro-5-methyl-phenoxy)-butyl]-piperazin-1-yl}-1H-indole 4-{4-[2-(2,5-Dichloro-phenylsulfanyl)-ethyl]-piperazin-1-yl}-1H-indole 4-{4-[2-(3-Chloro-phenylsulfanyl)-ethyl]-piperazin-1-yl}-1H-indole 4-{4-[2-(2-Chloro-phenylsulfanyl)-ethyl]-piperazin-1-yl}-1H-indole 4-{4-[3-(3-Chloro-phenylsulfanyl)-propyl]-piperazin-1-yl}-1H-indole 3-Chloro-4-{4-[4-(1H-indol-4-yl)-piperazin-1-yl]-butoxy}-benzonitrile 4-{4-[4-(3-Chloro-phenylsulfanyl)-butyl]-piperazin-1-yl}-1H-indole 4-{4-[4-(2-Chloro-phenylsulfanyl)-butyl]-piperazin-1-yl}-1H-indole 4-{4-[3-(3,4-Dimethyl-phenylsulfanyl)-propyl]-piperazin-1-yl}-1H-indole 3-{4-[4-(1H-Indol-4-yl)-piperazin-1-yl]-butoxy}-benzonitrile 4-{4-[4-(2,5-Dichloro-phenoxy)-butyl]-piperazin-1-yl}-1H-indole 4-{4-[4-(3,4-Dimethoxy-phenylsulfanyl)-butyl]-piperazin-1-yl}-1H-indole 4-{4-[3-(4-Trifluoromethyl-phenylsulfanyl)-propyl]-piperazin-1-yl}-1H-indole 4-{4-[3-(4-Trifluoromethoxy-phenylsulfanyl)-propyl]-piperazin-1-yl}-1H-indole 4-{4-[3-(3-Bromo-phenylsulfanyl)-propyl]-piperazin-1-yl}-1H-indole 4-{4-[3-(2-Isopropyl-phenylsulfanyl)-propyl]-piperazin-1-yl}-1H-indole 4-{4-[4-(2-Methoxy-phenoxy)-butyl]-piperazin-1-yl}-1H-indole or 4-{4-[4-(2-Isopropyl-phenylsulfanyl)-butyl]-piperazin-1-yl}-1H-indole or a pharmaceutically acceptable salt thereof.
- 13. A pharmaceutical composition comprising at least one compound of claim 1 according to any of the preceding claims or a pharmaceutically acceptable acid addition salt thereof or prodrug thereof in a therapeutically effective amount and in combination with one or more pharmaceutically acceptable carriers or diluents.
- 14. A method for the treatment of diseases or disorders in humans responsive to ligands of the 5-HT1a-receptor potentially in combination with serotonine reuptake and/or ligands at the dopamine D4-receptor, comprising administering an effective amount of a compound of claim 1.
- 15. A method according to claim 14 wherein said diseases or disorders are selected from the group consisting of affective disorders, eating disorders, and neurological disorders.
- 16. A method according to claim 15, wherein said diseases or disorders are affective disorders selected from the group consisting of generalised anxiety disorder, panic disorder, obsessive compulsive disorder, depression, and social phobia.
Priority Claims (1)
Number |
Date |
Country |
Kind |
PA 1999 01889 |
Dec 1999 |
DK |
|
Parent Case Info
[0001] This application is a continuation of International Application No. PCT/DK00/00742, filed Dec. 29, 2000. The disclosure of the prior application is hereby incorporated by reference herein, in its entirety.
Continuations (1)
|
Number |
Date |
Country |
Parent |
PCT/DK00/00742 |
Dec 2000 |
US |
Child |
10183961 |
Jun 2002 |
US |