Claims for Patent: 4,536,518
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Summary for Patent: 4,536,518
| Title: | Antidepressant derivatives of cis-4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine |
| Abstract: | Novel cis-isomeric derivatives of 4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine are useful as antidepressant agents. These novel compounds act to block the synaptosomal uptake of serotonin (5-hydroxy-tryptamine), thereby alleviating serotonin abnormalities at central receptor sites. The preferred embodiment is the enantiomer cis-(1S)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenam ine and its pharmaceutically acceptable acid addition salts. |
| Inventor(s): | Welch, Jr.; Willard M. (Mystic, CT), Harbert; Charles A. (Waterford, CT), Koe; B. Kenneth (Gales Ferry, CT), Kraska; Allen R. (East Lyme, CT) |
| Assignee: | Pfizer Inc. (New York, NY) |
| Application Number: | 06/090,240 |
| Patent Claims: |
1. A compound selected from the group consisting of cis-isomeric bases of the formula ##STR8## and the pharmaceutically acceptable acid addition salts thereof, wherein R.sub.1 is
selected from the group consisting of hydrogen and methyl,
R.sub.2 is methyl, Z is selected from the group consisting of 3-chlorophenyl, 4-chlorophenyl, 4-methoxyphenyl, 3-trifluoromethyl-phenyl, 4-trifluoromethyl-phenyl, 3,4-dichlorophenyl, 3-bromophenyl, 4-bromophenyl and 3-trifluoromethyl-4-chloro-phenyl, and W is selected from the group consisting of hydrogen, fluoro, chloro, bromo, trifluoromethyl and alkoxy of from 1 to 3 carbon atoms, with said compound being either the (1S)-enantiomer or the racemic mixture of the (1S)-enantiomer with the corresponding (1R)-enantiomer. 2. A compound of claim 1 wherein W is hydrogen. 3. A compound of claim 2 wherein Z is selected from the group consisting of 3,4-dichlorophenyl, 3-trifluoromethyl-phenyl, 4-chlorophenyl, 4-bromophenyl and 3-trifluoromethyl-4-chloro-phenyl. 4. A compound of claim 1 wherein W is 7-chloro. 5. A compound of claim 1 wherein R.sub.1 is hydrogen. 6. A compound of claim 1 wherein R.sub.1 is methyl. 7. A compound of claim 5 wherein W is hydrogen and Z is 3,4-dichlorophenyl. 8. A compound of claim 5 wherein W is hydrogen and Z is 4-bromophenyl. 9. A compound of claim 5 wherein W is hydrogen and Z is 4-chlorophenyl. 10. A compound of claim 5 wherein W is hydrogen and Z is 3-trifluoromethyl-phenyl. 11. A compound of claim 5 wherein W is hydrogen and Z is 3-trifluoromethyl-4-chloro-phenyl. 12. A compound of claim 6 wherein W is hydrogen and Z is 4-chlorophenyl. 13. A compound of claim 6 wherein W is hydrogen and Z is 3-trifluoromethyl-phenyl. 14. A compound of claim 6 wherein R.sub.1 is hydrogen and Z is 4-chlorophenyl. 15. A compound of claim 1, 2, 3, 4, 5, 6, 8, 9, 10, 11, 12, 13 or 14 wherein said compound is the (1S)-enantiomer. 16. A compound of claim 1, 2, 3, 4, 5, 6, 8, 9, 10, 11, 12, 13 or 14 wherein said compound is the racemic mixture of the (1S)-enantiomer with the corresponding (1R)-enantiomer. 17. A compound of claim 7 wherein said compound is the (1S)-enantiomer. 18. A compound of claim 7 wherein said compound is the racemic mixture of the (1S)-enantiomer with the corresponding (1R)-enantiomer. 19. A method for combatting mental depression in a mentally-depressed subject which comprises administering to said subject an effective amount of a compound of claim 1. 20. A method for combatting mental depression in a mentally-depressed subject which comprises administering to said subject an effective amount of a compound of claim 7. 21. A pharmaceutical composition containing an amount effective in combatting mental depression of a compound of claim 1 as the essential active ingredient in a pharmaceutically acceptable carrier. 22. A pharmaceutical composition containing an amount effective in combatting mental depression of a compound of claim 7 as the essential active ingredient in a pharmaceutically acceptable carrier. |
