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Last Updated: March 28, 2024

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.

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