Claims
- 1. A compound of Formula XI ##STR61## wherein n is 2-4;
- R.sub.2 is hydrogen or lower alkyl;
- X.sub.1 is oxygen or a direct bond;
- Y is hydrogen, halogen, lower alkoxy or CF.sub.3 with the proviso that when Y is hydrogen, n cannot be 2, R.sub.2 cannot be ethyl, X.sub.1 cannot be oxygen and Z cannot be phenyl having a mono halogen substituent;
- Z is benzyl or a radical selected from the group ##STR62## wherein R.sub.3 is hydrogen or halogen;
- R.sub.4 is halogen or CF.sub.3 ;
- R.sub.5 is hydrogen, halogen or cyano;
- R.sub.6 is hydrogen or halogen;
- or a pharmaceutically acceptable acid addition salt thereof.
- 2. The compound of claim 1 which is 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-2,4-dihydro-4-(3-phenoxypropyl)-3H-1,2,4-triazol-3-one.
- 3. The compound of claim 1 which is 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-2,4-dihydro-4-(4-phenoxybutyl)-3H-1,2,4-triazol-3-one.
- 4. The compound of claim 1 which is 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-2,4-dihydro-4-[2-(2-methoxyphenoxy)ethyl]-3H-1,2,4-triazol-3-one.
- 5. The compound of claim 1 which is 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-(1,1-dimethylethyl)-2,4-dihydro-4-(2-phenoxyethyl)-3H-1,2,4-triazol-3-one.
- 6. The compound of claim 1 which is 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-2,4-dihydro-4-[2-(4-methoxyphenoxy)ethyl]-3H-1,2,4-triazol-3-one.
- 7. The compound of claim 1 which is 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-2,4-dihydro-4-[2-[3-trifluoromethyl)phenoxy]ethyl]-3H-1,2,4-triazol-3-one.
- 8. The compound of claim 1 which is 4-[3-(3-chlorophenoxy)propyl]-2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-2,4-dihydro-3H-triazol-3-one.
- 9. The compound of claim 1 which is 4-[2-(3-chlorophenoxy)ethyl]-2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-2,4-dihydro-3H-1,2,4-triazol-3-one.
- 10. The compound of claim 1 which is 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-2,4-dihydro-4-[3-[3-(trifluoromethyl)phenoxy]propyl]-3H-1,2,4-triazol-3-one.
- 11. The compound of claim 1 which is 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-2,4-dihydro-4-(3-phenylpropyl)-3H-1,2,4-triazol-3-one.
- 12. The compound of claim 1 which is 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-2,4-dihydro-4-(4-phenylbutyl)-3H-1,2,4-triazol-3-one.
- 13. The compound of claim 1 which is 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-2,4-dihydro-4-(2-phenoxyethyl)-3H-1,2,4-triazol-3-one.
- 14. The compound of claim 1 which is 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-2,4-dihydro-4-[2-(3-chlorophenoxy)ethyl]-3H-1,2,4-triazol-3-one.
- 15. The compound of claim 1 which is 4-[3-(3-chlorophenoxy)propyl]-2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-2,4-dihydro-3H-1,2,4-triazol-3-one.
- 16. The compound of claim 1 which is 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-2,4-dihydro-4-[3-[3-(trifluoromethyl)phenoxy]propyl]-3H-1,2,4-triazol-3-one.
- 17. The compound of claim 1 which is 2-[3-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]propyl]-5-ethyl-2,4-dihydro-4-(2-phenoxyethyl)-3H-1,2,4-triazol-3-one.
- 18. The compound of claim 1 which is 2-[4-[3-[3-ethyl-4,5-dihydro-5-oxo-4-(2-phenoxyethyl)-1H-triazol-1-yl]propyl]-1-piperazinyl]-3-pyridinecarbonitrile.
- 19. The compound of claim 1 which is 5-ethyl-2,4-dihydro-4-(2-phenoxyethyl)-2-[3-[4-(phenylmethyl)-1-piperazinyl]propyl]-3H-1,2,4-triazol-3-one.
- 20. The compound of claim 1 which is 5-ethyl-2,4-dihydro-4-(2-phenoxyethyl)-2-[3-[4-(quinolin-2-yl)-1-piperazinyl]propyl]-3H-1,2,4-triazol-3-one.
- 21. The compound of claim 1 which is 2-[3-[4-(3-chloro-4-fluorophenyl)-1-piperazinyl]propyl]-5-ethyl-2,4-dihydro-4-(2-phenoxyethyl)-3H-1,2,4-triazol-3-one.
- 22. The compound of claim 1 which is 5-ethyl-2,4-dihydro-4-(2-phenoxyethyl)-2-[3-[4-[3-(trifluoromethyl)phenyl]-1-piperazinyl]propyl]-3H-1,2,4-triazol-3-one.
- 23. The compound of claim 1 which is 2-[3-[4-(2-chloro-6-pyrazinyl)-1-piperazinyl]propyl]-5-ethyl-2,4-dihydro-4-(2-phenoxyethyl)-3H-1,2,4-triazol-1-one.
- 24. The compound of claim 1 which is 2-[3-[4-(6-chloro-2-pyridinyl)-1-piperazinyl]propyl]-5-ethyl-2,4-dihydro-4-(2-phenoxyethyl)-3H-1,2,4-triazol-3-one.
- 25. The method for treating a mammal afflicted with depression comprising administering to said mammal a therapeutically effective antidepressant amount of a compound of claim 1 or a pharmaceutically acceptable acid addition salt thereof.
- 26. The pharmaceutical composition comprising an antidepressant amount of a compound of claim 1 or a pharmaceutically acceptable acid addition salt thereof and a pharmaceutically acceptable carrier.
- 27. 5-[3-[4-(3-Chlorophenyl)-1-piperazinyl]propyl]-4-ethyl-2,4-dihydro-2-(2-phenoxyethyl)-3H-1,2,4-triazol-3-one.
- 28. 5-[3-[4-(3-Chlorophenyl)-1-piperazinyl]propyl]-2,4-dihydro-4-(2-phenoxyethyl)-3H-1,2,4-triazol-3-one.
- 29. 5-[3-[4-(3-Chlorophenyl)-1-piperazinyl]propyl]-2-ethyl-2,4-dihydro-4-(2-phenoxyethyl)-3H-1,2,4-triazol-3-one.
CROSS-REFERENCE TO RELATED APPLICATION
This is a continuation-in-part application of Ser. No. 351,834 filed Feb. 24, 1982 and now abandoned which is a continuation-in-part of Ser. No. 244,464 filed Mar. 16, 1981 and now U.S. Pat. No. 4,338,317.
US Referenced Citations (4)
Number |
Name |
Date |
Kind |
3381009 |
Palazzo et al. |
Apr 1968 |
|
3857845 |
Palazzo |
Dec 1974 |
|
4338317 |
Temple, Jr. et al. |
Jul 1982 |
|
4386091 |
Temple, Jr. et al. |
May 1983 |
|
Non-Patent Literature Citations (2)
Entry |
Silvestrini, et al., Int. J. Neuropharmacol., 7, 587-599, (1968). |
Fabre, et al., Current Therapeutic Research, 25(6), 827-834, (1979). |
Continuation in Parts (2)
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Number |
Date |
Country |
Parent |
351834 |
Feb 1982 |
|
Parent |
244464 |
Mar 1981 |
|