Claims
- 1. A compound of the formula ##STR7## wherein: each of R.sup.1 and R.sup.2 independently is hydrogen or methyl;
- R.sup.3 is hydrogen, halo, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy or trifluoromethyl;
- each R.sup.4 independently is hydrogen, halo, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy or trifluoromethyl;
- m is 1 or 2;
- when m is 2, each R.sup.4 can be combined to form methylenedioxy; or a pharmaceutically acceptable acid addition salt thereof.
- 2. A compound of claim 1 wherein both R.sup.1 and R.sup.2 are hydrogen.
- 3. A compound of claim 1 wherein one of R.sup.1 and R.sup.2 is hydrogen and the other is methyl.
- 4. The compound of claim 1 wherein both of R.sup.1 and R.sup.2 are methyl.
- 5. The compound of claim 4 which is N,N-dimethyl-1-phenyl-3-(1-naphthalenyloxy)propanamine, or a pharmaceutically acceptable acid addition salt thereof.
- 6. A compound of claim 4 which is the (+) stereoisomer.
- 7. The compound of claim 6 which is (+)-N,N-dimethyl-1-phenyl-3-(1-naphthalenyloxy)propanamine, or a pharmaceutically acceptable acid addition salt thereof.
- 8. The compound of claim 7 which is (+)-N,N-dimethyl-1-phenyl-3-(1-naphthalenyloxy)propanamine tartrate.
- 9. The compound of claim 4 which is the (-)stereoisomer.
- 10. The compound of claim 9 which is (-)-N,N-dimethyl-1-phenyl-3-(1-naphthalenyloxy)propanamine, or a pharmaceutically acceptable acid addition salt thereof.
- 11. A compound of claim 10 which is (-)-N,N-dimethyl-1-phenyl-3-(1-naphthalenyloxy)propanamine tartrate.
- 12. 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 or a pharmaceutically acceptable acid addition salt thereof.
- 13. A method of claim 12 wherein both R.sup.1 and R.sup.2 are methyl.
- 14. The method of claim 13 wherein the compound is N,N-dimethyl-1-phenyl-3-(1-naphthalenyloxy)-propanamine, or a pharmaceutically acceptable acid addition salt thereof.
- 15. The method of claim 14 wherein the compound is N,N-dimethyl-1-phenyl-3-(1-naphthalenyloxy)propanamine tartrate.
- 16. The method of claim 15 wherein the (+)-stereoisomer of the compound is employed.
- 17. A method of claim 15 wherein the (-)-stereoisomer of the compound is employed.
- 18. 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 or a pharmaceutically acceptable acid addition salt thereof.
- 19. A method of claim 18 wherein both R.sup.1 and R.sup.2 are methyl.
- 20. The method of claim 19 wherein the compound is N,N-dimethyl-1-phenyl-3-(1-naphthalenyloxy)-propanamine, or a pharmaceutically acceptable acid addition salt thereof.
- 21. The method of claim 20 wherein the compound is N,N-dimethyl-1-phenyl-3-(1-naphthalenyloxy)-propanamine tartrate.
- 22. The method of claim 21 wherein the (+)-stereoisomer of the compound is employed.
- 23. The method of claim 21 wherein the (-)-stereoisomer is employed.
- 24. A method of treating anxiety in humans comprising administering to a human suffering from anxiety an effective antianxiety dose of a compound of claim 1 or a pharmaceutically acceptable acid addition salt thereof.
- 25. A method of claim 24 wherein both R.sup.1 and R.sup.2 are methyl.
- 26. The method of claim 25 wherein the compound is N,N-dimethyl-1-phenyl-3-(1-naphthalenyloxy)-propanamine, or a pharmaceutically acceptable acid addition salt thereof.
- 27. The method of claim 26 wherein the compound is N,N-dimethyl-1-phenyl-3-(1-naphthalenyloxy)-propanamine tartrate.
- 28. The method of claim 27 wherein the (+)-stereoisomer of the compound is employed.
- 29. The method of claim 27 wherein the (-)-stereoisomer is employed.
- 30. 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 or a pharmaceutically acceptable acid addition salt thereof.
- 31. A method of claim 30 wherein both R.sup.1 and R.sup.2 are methyl.
- 32. The method of claim 31 wherein the compound is N,N-dimethyl-1-phenyl-3-(1-naphthalenyloxy)-propanamine, or a pharmaceutically acceptable acid addition salt thereof.
- 33. The method of claim 31 wherein the compound is N,N-dimethyl-1-phenyl-3-(1-naphthalenyloxy)-propanamine tartrate.
- 34. The method of claim 33 wherein the (+)-stereoisomer of the compound is employed.
- 35. The method of claim 33 wherein the (-)-stereoisomer is employed.
- 36. 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 or a pharmaceutically acceptable acid addition salt thereof.
- 37. A method of claim 36 wherein both R.sup.1 and R.sup.2 are methyl.
- 38. The method of claim 37 wherein the compound is N,N-dimethyl-1-phenyl-3-(1-naphthalenyloxy)-propanamine, or a pharmaceutically acceptable acid addition salt thereof.
- 39. The method of claim 38 wherein the compound is N,N-dimethyl-1-phenyl-3-(1-naphthalenyloxy)-propanamine tartrate.
- 40. The method of claim 39 wherein the (+)-stereoisomer of the compound is employed.
- 41. The method of claim 39 wherein the (-)-stereoisomer is employed.
- 42. 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 or a pharmaceutically acceptable acid addition salt thereof.
- 43. A method of claim 42 wherein both R.sup.1 and R.sup.2 are methyl.
- 44. The method of claim 43 wherein the compound is N,N-dimethyl-1-phenyl-3-(1-naphthalenyloxy)-propanamine, or a pharmaceutically acceptable acid addition salt thereof.
- 45. The method of claim 44 wherein the compound is N,N-dimethyl-1-phenyl-3-(1-naphthalenyloxy)-propanamine tartrate.
- 46. The method of claim 45 wherein the (+)-stereoisomer of the compound is employed.
- 47. The method of claim 45 wherein the (-)-stereoisomer is employed.
- 48. A pharmaceutical formulation comprising a compound of claim 1, or a pharmaceutically acceptable acid addition salt thereof and a pharmaceutically acceptable carrier, diluent or excipient therefor.
- 49. A formulation of claim 48 wherein both R.sup.1 and R.sup.2 are methyl.
- 50. The formulation of claim 49 wherein the compound is N,N-dimethyl-1-phenyl-3-(1-naphthalenyloxy)-propanamine, or a pharmaceutically acceptable acid addition salt thereof.
- 51. The formulation of claim 50 wherein the compound is N,N-dimethyl-1-phenyl-3-(1-naphthalenyloxy)-propanamine tartrate.
- 52. The formulation of claim 51 wherein the (+)stereoisomer of the compound is employed.
- 53. The formulation of claim 52 wherein the (-)-stereoisomer of the compound is employed.
Parent Case Info
This application is a continuation of application Ser. No. 07/372,149, filed on Jun. 26, 1989, now abandoned, which is a continuation of application Ser. No. 07/191,465, filed on May 9, 1988, now abandoned, which is a continuation-in-part of copending application U.S. Ser. No. 07/036,534, filed on Apr. 9, 1987, now abandoned.
US Referenced Citations (5)
Foreign Referenced Citations (1)
Number |
Date |
Country |
2060618 |
May 1981 |
GBX |
Non-Patent Literature Citations (1)
Entry |
Cronenberger et al., Chemie Therapeutique, 5/6, 289 (1966). |
Continuations (2)
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Number |
Date |
Country |
Parent |
372149 |
Jun 1989 |
|
Parent |
191465 |
May 1988 |
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Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
36534 |
Apr 1987 |
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