Claims
- 1. A compound of the formula ##STR82## wherein: R.sup.1 is thienyl, halothienyl, (C.sub.1 -C.sub.4 alkyl)thienyl, furanyl, pyridyl or thiazolyl; ##STR83## each of R.sup.2 and R.sup.3 independently is hydrogen or methyl; each R.sup.4 independently is halo, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy or trifluoromethyl;
- each R.sup.5 independently is halo, C.sub.1 C.sub.4 alkyl or trifluoromethyl;
- m is 0, 1 or 2;
- n is 0 or 1; and
- the pharmaceutically acceptable acid addition salts thereof.
- 2. A compound of claim 1 wherein Ar is ##STR84##
- 3. A compound of claim 2 wherein R.sup.1 is halothienyl.
- 4. A compound of claim 2 wherein R.sup.1 is (C.sub.1 -C.sub.4 alkyl)thienyl.
- 5. A compound of claim 2 wherein R.sup.1 is furanyl.
- 6. A compound of claim 2 wherein R.sup.1 is pyridyl.
- 7. A compound of claim 2 wherein R.sup.1 is thiazolyl.
- 8. A compound of claim 2 wherein R.sup.1 is thienyl.
- 9. A compound of claim 8 wherein one of R.sup.2 and R.sup.3 is hydrogen and the other is methyl.
- 10. The compound of claim 10 which is N-methyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine, and its pharmaceutically acceptable acid addition salts.
- 11. The compound of claim 11 which is the (+) stereoisomer.
- 12. The compound of claim 12 which is (+)-N-methyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine maleate.
- 13. A compound of claim 1 wherein Ar is ##STR85##
- 14. A compound of claim 13 wherein R.sup.1 is thienyl.
- 15. A compound of claim 13 wherein R.sup.1 is halothienyl.
- 16. A compound of claim 13 wherein R.sup.1 is (C.sub.1 -C.sub.4 alkyl)thienyl.
- 17. A compound of claim 13 wherein R.sup.1 is furanyl.
- 18. A compound of claim 13 wherein R.sup.1 is pyridyl.
- 19. A compound of claim 13 wherein R.sup.1 is thiazolyl.
- 20. A method for inhibiting serotonin uptake in mammals which comprises administering to a mammal requiring increased neurotransmission of serotonin a pharmaceutically effective amount of a compound of claim 1.
- 21. A method of claim 20 wherein R.sup.1 is thienyl.
- 22. A method of claim 21 wherein the compound is N-methyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine, and its pharmaceutically acceptable acid addition salts.
- 23. A method of claim 22 wherein the compound is (+)-N-methyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine, and its pharmaceutically acceptable acid addition salts.
- 24. A method for inhibiting norepinephrine uptake in mammals which comprises administering to a mammal requiring increased neurotransmission of norepinephrine a pharmaceutically effective amount of a compound of claim 1.
- 25. A method of claim 24 wherein one of R.sup.2 and R.sup.3 is hydrogen and the other is methyl.
- 26. A method of claim 25 wherein the compound is N-methyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine, and its pharmaceutically acceptable acid addition salts.
- 27. A method of claim 25 wherein the compound is (+)-N-methyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine, and its pharmaceutically acceptable acid addition salts.
- 28. A method of treating depression in humans comprising administering to a human suffering from depression an effective antidepressant dose of a compound of claim 1.
- 29. A method claim 28 wherein R.sup.1 is thienyl.
- 30. A method of claim 29 wherein the compound is N-methyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine, and its pharmaceutically acceptable acid addition salts.
- 31. A method of claim 30 wherein the compound is (+)-N-methyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine, and its pharmaceutically acceptable acid addition salts.
- 32. A method of treating anxiety in human comprising administering to a human suffering from anxiety an effective antianxiety dose of a compound of claim 1.
- 33. A method of claim 32 wherein R.sup.1 is thienyl.
- 34. A method of claim 33 wherein the compound is N-methyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine, and its pharmaceutically acceptable acid addition salts.
- 35. A method of claim 34 wherein the compound is (+)-N-methyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine, and its pharmaceutically acceptable acid addition salts.
- 36. A method of treating obesity in humans comprising administering to a human suffering from obesity an effective antiobesity dose of a compound of claim 1.
- 37. A method of claim 38 wherein R.sup.1 is thienyl.
- 38. A method of claim 37 wherein the compound is N-methyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine, and its pharmaceutically acceptable acid addition salts.
- 39. A method of claim 38 wherein the compound is (+)-N-methyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine, and its pharmaceutically acceptable acid addition salts.
- 40. A method of suppressing the desire of humans to smoke comprising administering to a human in need of such suppression an effective dose to relieve the desire to smoke of a compound of claim 1.
- 41. A method of claim 40 wherein R.sup.1 is thienyl.
- 42. A method of claim 41 wherein the compound is N-methyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine, and its pharmaceutically acceptable acid addition salts.
- 43. A method of claim 42 wherein the compound is (+)-N-methyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine, and its pharmaceutically acceptable acid addition salts.
- 44. A method of suppressing the desire of humans to consume alcohol comprising administering to a human in need of such suppression an effective dose to relieve the desire to consume alcohol of a compound of claim 1.
- 45. A method of claim 44 wherein R.sup.1 is thienyl.
- 46. A method of claim 45 wherein the compound is N-methyl-3-(1-naphthalenyloxy)-3-2-thienyl)propanamine, and its pharmaceutically acceptable acid addition salts.
- 47. A method of claim 46 wherein the compound is (+)-N-methyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine, and its pharmaceutically acceptable acid addition salts.
- 48. A pharmaceutical formulation comprising a compound of claim 1 and a pharmaceutically acceptable carrier, diluent or excipient therefor.
- 49. A formulation of claim 48 wherein R.sup.1 is thienyl.
- 50. A formulation of claim 49 wherein the compound is N-methyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine, and its pharmaceutically acceptable acid addition salts.
- 51. A formulation of claim 50 wherein the compound is (+)-N-methyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine, and its pharmaceutically acceptable acid.
Parent Case Info
This application is a division of application Ser. No. 07/462,925, filed Jan. 12, 1990, now U.S. Pat. No. 4,956,388, continuation of application Ser. No. 06/945,122, filed on Dec. 22, 1986, now abandoned.
US Referenced Citations (10)
Foreign Referenced Citations (3)
Number |
Date |
Country |
2482956 |
May 1980 |
FRX |
1343527 |
Jan 1974 |
GBX |
2060618 |
May 1981 |
GBX |
Divisions (1)
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Number |
Date |
Country |
Parent |
462925 |
Jan 1990 |
|
Continuations (1)
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Number |
Date |
Country |
Parent |
945122 |
Dec 1986 |
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