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Last Updated: April 19, 2024

Claims for Patent: 5,023,269

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Summary for Patent: 5,023,269

Title:	3-aryloxy-3-substituted propanamines
Abstract:	The present invention provides 3-aryloxy-3-substituted propanamines capable of inhibiting the uptake of serotonin and norepinephrine.
Inventor(s):	Robertson; David W. (Greenwood, IN), Wong; David T. (Indianapolis, IN), Krushinski, Jr.; Joseph H. (Indianapolis, IN)
Assignee:	Eli Lilly and Company (Indianapolis, IN)
Application Number:	07/499,940
Patent 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.

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