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Details for Patent: 4,487,773

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Details for Patent: 4,487,773

Title: 1,2,4-Triazol-3-one antidepressants
Abstract:Phenoxyalkyl substituted-1,2,4-triazolones having anti-depressant properties typified by 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-4-(2-phenoxyethyl)- 2H-1,2,4-triazol-3(4H)-one are disclosed.
Inventor(s): Temple, Jr.; Davis L. (Evansville, IN), Lobeck, Jr.; Walter G. (Evansville, IN)
Assignee: Mead Johnson & Company (Evansville, IN)
Filing Date:Jun 29, 1983
Application Number:06/509,266
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-ph enoxypropyl)-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-ph enoxybutyl)-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-d ihydro-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]propy l]-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-ph enylpropyl)-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-ph enylbutyl)-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-phenoxyeth yl)-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-chlorop henoxy)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]propy l]-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-(triflu oromethyl)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-dihydr o-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]prop yl]-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-piperaziny l]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-piperazin yl]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-dihydr o-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.
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