Claims
- 1. A compound having the formula
- 2. The compound of claim 1, wherein said aryl group is selected from the group consisting of phenyl, naphthyl, and biphenyl.
- 3. The compound of claim 1, wherein said heteroaryl group is selected from the group consisting of thiazole, oxazole, benzothiazole, benzoxazole, pyrazole, indole, and indazole.
- 4. The compound of claim 1, wherein said substituted aryl group is selected from the group consisting of mono-, di-, or tri-substituted phenyl, naphthyl, or biphenyl with methyl, ethyl, propyl, allyl, n-butyl, n-pentyl, n-hexyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropoxy, cyclopentyloxy, phenoxy, benzyloxy, phenylethoxy, fluoro, chloro, bromo, iodo, amino, dimethylamino, nitro, cyano, trifluoromethyl, trifluoromethoxy, tetrazolo, sulphonyl, thiomethyl, thioethyl, phenylthio, 2,3-methylenedioxy, and 3,4-methylenedioxy.
- 5. The compound of claim 1, wherein said substituted aryl group is selected from the group consisting of mono-, di-, or tri-substituted thiazole, oxazole, benzothiazole, benzoxazole, pyrazole, indole, and indazole.
- 6. The compound of claim 5, wherein said substituent is selected from the group consisting of methyl, ethyl, propyl, allyl, n-butyl, n-pentyl, n-hexyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropoxy, cyclopentyloxy, phenoxy, benzyloxy, phenylethoxy, fluoro, chloro, bromo, iodo, amino, dimethylamino, nitro, cyano, trifluoromethyl, trifluoromethoxy, tetrazolo, sulphonyl, thiomethyl, thioethyl, phenylthio, 2,3-methylenedioxy, and 3,4-methylenedioxy.
- 7. The compound of claim 1, wherein X is sulfur.
- 8. A pharmaceutical composition comprising the compound of claim 1 in an amount effective to treat a respiratory disorder.
- 9. The pharmaceutical composition of claim 8, wherein said respiratory disorder is asthma.
- 10. A pharmaceutical composition comprising the compound of claim 1 in an amount effective to treat an inflammatory disorder.
- 11. A pharmaceutical composition comprising the compound of claim 1 in an amount effective to treat inflammation.
- 12. A pharmaceutical composition comprising the compound of claim 1 in an amount effective to treat inflammation in a mammal suffering therefrom.
- 13. A pharmaceutical composition comprising the compound of claim 1 in an amount effective to treat a gastrointestinal disorder.
- 14. The pharmaceutical composition of claim 13, wherein said gastrointestinal disorder is selected from the group consisting of Crohn's disease; colitis; and irritable bowel syndrome.
- 15. A pharmaceutical composition comprising the compound of claim 1 in an amount effective to treat an opthalmic disease.
- 16. The pharmaceutical composition of claim 15, wherein said opthalmic disease is selected from the group consisting of glaucoma; dry eye; conjunctivitis; and ocular hypotension.
- 17. A pharmaceutical composition comprising the compound of claim 1 in an amount effective to treat a condition selected from the group consisting of neural injury; schizophrenia; stroke; psoriasis; an allergic condition; rhinitis and eczema; a CNS disorder; migraines; inflammatory pain; anxiety or depression; emesis; cancer chemotherapy-induced emesis; rheumatoid arthritis; tumor cell growth; and atherosclerosis.
- 18. A method of treating a respiratory disorder, comprising administering to a patient in need thereof a pharmaceutical composition comprising the compound of claim 1 in an amount effective to treat said respiratory disorder.
- 19. A method of treating an inflammatory disorder, comprising administering to a patient in need thereof a pharmaceutical composition comprising the compound of claim 1 in an amount effective to treat said inflammatory disorder.
- 20. A method of treating inflammation, comprising administering to a patient in need thereof a pharmaceutical composition comprising the compound of claim 1 in an amount effective to treat said inflammation.
- 21. A method of treating a gastrointestinal disorder, comprising administering to a patient in need thereof a pharmaceutical composition comprising the compound of claim 1 in an amount effective to treat said gastrointestinal disorder.
- 22. A method of treating an opthalmic disease, comprising administering to a patient in need thereof a pharmaceutical composition comprising the compound of claim 1 in an amount effective to treat said opthalmic disease.
- 23. A method of treating an allergic condition, comprising administering to a patient in need thereof a pharmaceutical composition comprising the compound of claim 1 in an amount effective to treat said allergic condition.
- 24. A method of treating a CNS disorder, comprising administering to a patient in need thereof a pharmaceutical composition comprising the compound of claim 1 in an amount effective to treat said CNS disorder.
- 25. A compound having the formula
- 26. The compound of claim 25, wherein said aryl group is selected from the group consisting of phenyl, naphthyl, and biphenyl.
- 27. The compound of claim 25, wherein said heteroaryl group is selected from the group consisting of thiazole, oxazole, benzothiazole, benzoxazole, pyrazole, indole, and indazole.
- 28. The compound of claim 25, wherein said substituted aryl group is selected from the group consisting of mono-, di-, or tri-substituted phenyl, naphthyl, or biphenyl with methyl, ethyl, propyl, allyl, n-butyl, n-pentyl, n-hexyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropoxy, cyclopentyloxy, phenoxy, benzyloxy, phenylethoxy, fluoro, chloro, bromo, iodo, amino, dimethylamino, nitro, cyano, trifluoromethyl, trifluoromethoxy, tetrazolo, sulphonyl, thiomethyl, thioethyl, phenylthio, 2,3-methylenedioxy, and 3,4-methylenedioxy.
- 29. The compound of claim 25, wherein said substituted aryl group is selected from the group consisting of mono-, di-, or tri-substituted thiazole, oxazole, benzothiazole, benzoxazole, pyrazole, indole, and indazole.
- 30. The compound of claim 30, wherein said substituent is selected from the group consisting of methyl, ethyl, propyl, allyl, n-butyl, n-pentyl, n-hexyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropoxy, cyclopentyloxy, phenoxy, benzyloxy, phenylethoxy, fluoro, chloro, bromo, iodo, amino, dimethylamino, nitro, cyano, trifluoromethyl, trifluoromethoxy, tetrazolo, sulphonyl, thiomethyl, thioethyl, phenylthio, 2,3-methylenedioxy, and 3,4-methylenedioxy.
- 31. A compound having the formula
- 32. The compound of claim 31, wherein R4 is mono-, di- or trisubstituted with halo, trihalomethyl, hydroxyl, alkoxy, or with a dioxole ring.
- 33. A compound selected from the group consisting of 1-(4-Methoxy-phenoxy)-3-[1-(5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-ylamino]-propan-2-ol; 2-{1-[5-(4-Bromo-phenyl)-thieno[2,3-d]pyrimidin-4-yl]-piperidin-4-ylamino}-cyclohexanol; 2-[1-(5-p-Tolyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-ylamino]-cyclohexanol; 2-[1-(6-Methyl-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-ylamino]-cyclohexanol; 1-(4-Chloro-phenoxy)-3-[1-(5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-ylamino]-propan-2-ol; and pharmaceutically acceptable salts and/or esters thereof.
- 34. A compound selected from the group consisting of 1-Phenoxy-3-[1-(5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-ylamino]-propan-2-ol; 1-Benzyloxy-3-[1-(5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-ylamino]-propan-2-ol; 1-(Benzo[1,3]dioxol-5-yloxy)-3-[1-(5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-ylamino]-propan-2-ol; 1-(Benzo[1,3]dioxol-5-ylmethoxy)-3-[1-(5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-ylamino]-propan-2-ol; 1-(3,4-Difluoro-phenoxy)-3-[1-(5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-ylamino]-propan-2-ol; and pharmaceutically acceptable salts and/or esters thereof.
- 35. A compound selected from the group consisting of 1-(2-Chloro-4-methoxy-phenoxy)-3-[4-(5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-cyclohexylamino]-propan-2-ol; 1-(3,4-Dimethoxy-phenoxy)-3-[4-(5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-cyclohexylamino]-propan-2-ol; 1-(3,4-Dichloro-phenoxy)-3-[1-(5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-ylamino]-propan-2-ol; 1-(3-Chloro-4-fluoro-phenoxy)-3-[1-(5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-ylamino]-propan-2-ol; 1-(2,4-Difluoro-phenoxy)-3-[1-(5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-ylamino]-propan-2-ol; and pharmaceutically acceptable salts and/or esters thereof.
- 36. A compound selected from the group consisting of 1-(3,5-Difluoro-phenoxy)-3-[1-(5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-ylamino]-propan-2-ol; 1-(3,5-Bis-trifluoromethyl-phenoxy)-3-[1-(5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-ylamino]-propan-2-ol; 1-(Benzo[1,3]dioxol-5-yloxy)-3-[1-(5-methyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-ylamino]-propan-2-ol; 1-(Benzo[1,3]dioxol-5-yloxy)-3-(1-thieno[2,3-d]pyrimidin-4-yl-piperidin-4-ylamino)-propan-2-ol; 2-[1-(5-Phenyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-ylamino]-cyclohexanol; and pharmaceutically acceptable salts and/or esters thereof.
- 37. A compound selected from the group consisting of 2-[1-(6-Methyl-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-ylamino]-cyclohexanol; 1-[1-(6-Methyl-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-ylamino]-indan-2-ol; 5-Methoxy-2-{[1-(5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-ylamino]-methyl}-phenol; Bis-(2-fluoro-benzyl)-[1-(5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-yl]-amine; 1-{1-[5-(4-Bromo-phenyl)-thieno[2,3-d]pyrimidin-4-yl]-piperidin-4-ylamino}-indan-2-ol; and pharmaceutically acceptable salts and/or esters thereof.
- 38. A compound selected from the group consisting of 1-[1-(5-p-Tolyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-ylamino]-indan-2-ol; 2-Fluoro-6-{[1-(6-methyl-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-ylamino]-methyl}-phenol; 2-({1-[5-(4-Bromo-phenyl)-thieno[2,3-d]pyrimidin-4-yl]-piperidin-4-ylamino}-methyl)-6-fluoro-phenol; 2-Fluoro-6-{[1-(5-p-tolyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-ylamino]-methyl}-phenol; 1-[1-(5-Phenyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-ylamino]-indan-2-ol; and pharmaceutically acceptable salts and/or esters thereof.
- 39. A compound selected from the group consisting of 1-(4-Fluoro-phenoxy)-3-[1-(5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-ylamino]-propan-2-ol; 1-[1-(5-Phenyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-ylamino]-3-(4-trifluoromethoxy-phenoxy)-propan-2-ol; 1-(3,4-Difluoro-phenoxy)-3-{1-[5-(4-fluoro-phenyl)-thieno[2,3-d]pyrimidin-4-yl]-piperidin-4-ylamino}-propan-2-ol; [2-Hydroxy-3-(4-methoxy-phenoxy)-propyl]-[1-(5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-yl]-ammonium; chloride; and pharmaceutically acceptable salts and/or esters thereof.
- 40. A compound selected from the group consisting of [3-(2-Chloro-4-methoxy-phenoxy)-2-hydroxy-propyl]-[4-(5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-cyclohexyl]-ammonium; chloride; [3-(3,4-Dimethoxy-phenoxy)-2-hydroxy-propyl]-[4-(5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-cyclohexyl]-ammonium; chloride; [3-(3,4-Dichloro-phenoxy)-2-hydroxy-propyl]-[1-(5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-yl]-ammonium; chloride; [3-(2,4-Difluoro-phenoxy)-2-hydroxy-propyl]-[1-(5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-piperidin-4-yl]-ammonium; chloride; and pharmaceutically acceptable salts and/or esters thereof.
RELATED APPLICATIONS
[0001] This application claims the benefit of priority under 35 U.S.C. 119(e) to copending U.S. Provisional Application Nos. 60/401,952, filed on Aug. 8, 2002 as Docket No. 24591-501 PRO; 60/414,998, filed on Oct. 1, 2002 as Docket No. 24591-501 PRO B; and 60/465,379, filed on Apr. 25, 2003 as Docket No. 24591-501 PRO C, the entire contents of which are incorporated herein by reference.
Provisional Applications (3)
|
Number |
Date |
Country |
|
60401952 |
Aug 2002 |
US |
|
60414998 |
Oct 2002 |
US |
|
60465379 |
Apr 2003 |
US |