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Generated: September 24, 2017

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Title: 2-Phenyl-2-(1-hydroxycycloalkyl or 1-hydroxycycloalk-2-enyl)ethylamine derivatives
Abstract:This invention provides a group of hydroxycycloalkanephenethyl amine antidepressant derivatives of the following structural formula: ##STR1## in which A is a moiety of the formula ##STR2## where the dotted line represents optional unsaturation; R.sub.1 is hydrogen or alkyl; R.sub.2 is alkyl; R.sub.4 is hydrogen, alkyl, formyl or alkanoyl; R.sub.5 and R.sub.6 are, independently, hydrogen, hydroxyl, alkyl, alkoxy, alkanoyloxy, cyano, nitro, alkylmercapto, amino, alkylamino, dialkylamino, alkanamido, halo, trifluoromethyl or, taken together, methylenedioxy; R.sub.7 is hydrogen or alkyl; and n is 0, 1, 2, 3 or 4; or a pharmaceutically acceptable salt thereof.
Inventor(s): Husbands; G. E. Morris (Berwyn, PA), Yardley; John P. (Gulph Mills, PA), Muth; Eric A. (West Chester, PA)
Assignee: American Home Products Corporation (New York, NY)
Application Number:06/545,701
Patent Claims: 1. A compound of the formula: ##STR17## wherein the dotted line represents optional olefinic unsaturation, and

R.sub.1 is hydrogen or alkyl of 1 to 6 carbon atoms;

R.sub.2 is alkyl of 1 to 6 carbon atoms;

R.sub.4 is hydrogen, alkyl of 1 to 6 carbon atoms, formyl, or alkanoyl of 2 to 7 carbon atoms;

R.sub.5 and R.sub.6 are independently hydrogen, hydroxyl, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkanoyloxy of 2 to 7 carbon atoms, nitro, alkylmercapto of 1 to 6 carbon atoms, amino, alkylamino of 1 to 6 carbon atoms, dialkylamino in which each alkyl group is of 1 to 6 carbon atoms, alkanamido of 2 to 7 carbon atoms, halo, or trifluoromethyl;

R.sub.7 is hydrogen or alkyl of 1 to 6 carbon atoms; and

n is one of the integers 0, 1, 2, 3 or 4;

or a pharmaceutically acceptable salt thereof.

2. A compound of claim 1 in which in which R.sub.1 is hydrogen or alkyl of 1 to 3 carbon atoms; R.sub.2 is alkyl of 1 to 3 carbon atoms; R.sub.5 is hydrogen, alkoxy of 1 to 3 carbon atoms, chloro, bromo, trifluoromethyl or alkyl of 1 to 3 carbon atoms; R.sub.6 is alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, chloro, bromo, trifluoromethyl or alkanoyloxy of 2 to 3 carbon atoms; R.sub.7 is hydrogen or alkyl of 1 to 3 carbon atoms; or a pharmaceutically acceptable salt thereof.

3. A compound of claim 2 in which R.sub.5 and R.sub.6 are in meta or para positions and n is 2.

4. The compound of claim 1 which is 1-[(2-dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexanol or a pharmaceutically acceptable salt thereof.

5. The compound of claim 1 which is 1-(.alpha.-[(dimethylamino)methyl]benzyl)cyclohexanol or a pharmaceutically acceptable salt thereof.

6. The compound of claim 1 which is 1-(.alpha.-[methylamino)methyl]benzyl)cyclohexanol or a pharmaceutically acceptable salt thereof.

7. The compound of claim 1 which is 1-[1-(4-chlorophenyl)-2-(dimethylamino)ethyl]cyclohexanol or a pharmaceutically acceptable salt thereof.

8. The compound of claim 1 which is 1-[1-(4-methoxyphenyl)-2-(methylamino)ethyl]cyclohexanol or a pharmaceutically acceptable salt thereof.

9. The compound of claim 1 which is 1-[1-(4-bromophenyl-2-(dimethylamino)ethyl]cyclohexanol or a pharmaceutically acceptable salt thereof.

10. The compound of claim 1 which is 1-[1-(3-bromophenyl)-2-(dimethylamino)ethyl]cyclohexanol or a pharmaceutically acceptable salt thereof.

11. The compound of claim 1 which is 1-[1-(3-chlorophenyl)-2-(dimethylamino)ethyl]cyclohexanol or a pharmaceutically acceptable salt thereof.

12. The compound of claim 1 which is 1-[1-(2-chlorophenyl)-2-(dimethylamino)ethyl]cyclohexanol or a pharmaceutically acceptable salt thereof.

13. The compound of claim 1 which is 1-[1-(3,4-dichlorophenyl)-2-(dimethylamino)ethyl]cyclohexanol or a pharmaceutically acceptable salt thereof.

14. The compound of claim 1 which is 1-[2-[1-(dimethylamino)-2-(4-methoxyphenyl)propyl]]cyclohexanol or a pharmaceutically acceptable salt thereof.

15. The compound of claim 1 which is 1-[2-(dimethylamino)-1-(3-methoxyphenyl)ethyl]cyclohexanol or a pharmaceutically acceptable salt thereof.

16. The compound of claim 1 which is 1-[1-(3,4-dimethoxyphenyl)-2-(dimethylamino)ethyl]cyclohexanol or a pharmaceutically acceptable salt thereof.

17. The compound of claim 1 which is 1-[2-(dimethylamino)-1-(4-trifluoromethylphenyl)ethyl]cyclohexanol or a pharmaceutically acceptable salt thereof.

18. The compound of claim 1 which is 1-[2-(dimethylamino)-1-(3-trifluoromethylphenyl)ethyl]cyclohexanol or a pharmaceutically acceptable salt thereof.

19. The compound of claim 1 which is 1-[2-(dimethylamino)-1-(4-methylphenyl)ethyl]cyclohexanol or a pharmaceutically acceptable salt thereof.

20. The compound of claim 1 which is 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohex-2-en-1-ol or a pharmaceutically acceptable salt thereof.

21. The compound of claim 1 which is 1-[2-(dimethylamino)-1-(4-hydroxyphenyl)ethyl]cyclohexanol or a pharmaceutically acceptable salt thereof.

22. The compound of claim 1 which is 1-[2-(dimethylamino)-1-(3-hydroxyphenyl)ethyl]cyclohexanol or a pharmaceutically acceptable salt thereof.

23. The compound of claim 1 which is 1-[1-(4-aminophenyl)-2-(dimethylamino)ethyl]cyclohexanol or a pharmaceutically acceptable salt thereof.

24. The compound of claim 1 which is 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclopentanol or a pharmaceutically acceptable salt thereof.

25. The compound of claim 1 which is 1-[1-(4-nitrophenyl)-2-(dimethylamino)ethyl]cyclohexanol or a pharmaceutically acceptable salt thereof.

26. The compound of claim 1 which is 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cycloheptanol or a pharmaceutically acceptable salt thereof.

27. The compound of claim 1 which is 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclooctanol or a pharmaceutically acceptable salt thereof.

28. The compound of claim 1 which is 1-[2-(dimethylamino)-1-(3-bromo-4-methoxyphenyl)ethyl]cyclohexanol or a pharmaceutically acceptable salt thereof.

29. The compound of claim 1 which is 1-[1-(3,4-dibromophenyl)-2-(dimethylamino)ethyl]cyclohexanol or a pharmaceutically acceptable salt thereof.

30. The compound of claim 1 which is 1-[(2-dimethylamino)-1-(3-methylphenyl)ethyl]cyclohexanol or a pharmaceutically acceptable salt thereof.

31. The compound of claim 1 which is 1-[1-(4-bromophenyl-2-(dimethylamino)ethyl]cyclobutanol or a pharmaceutically acceptable salt thereof.

32. The compound of claim 1 which is 1-[2-(dimethylamino)-1-(3-methoxyphenyl)ethyl]cyclopentanol or a pharmaceutically acceptable salt thereof.
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