Claims
- 1. A compound having the general formula I
- 2. A compound according to claim 1 wherein R is chosen from the group consisting of phenyl, cyclohexyl, and trifluoromethyl group.
- 3. A compound according to claim 1 wherein R1 is chosen from the group consisting of methyl, methoxy and 2,2,2-trifluoroethoxy group.
- 4. A compound according to claim 1 wherein R2 is chosen from the group consisting of hydrogen and fluorine.
- 5. A compound according to claim 1 wherein R3 is chosen from the group consisting of hydrogen, chlorine and a 2,2,2-trifluoroethoxy group.
- 6. A compound according to claim 1 wherein n=1.
- 7. A compound selected from the group consisting of a
N-{3-[4-(5-chloro-2-methoxyphenyl)-1-piperazinyl]propyl}-7-oxo-5-phenyl-7H-thieno[3,2-b]pyran-3-carboxamide, N-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propyl}-7-oxo-5-phenyl-7H-thieno[3,2-b]pyran-3-carboxamide, 5-cyclohexyl-N-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propyl}-7-oxo-7H-thieno[3,2-b]pyran-3-carboxamide, N-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propyl}-7-oxo-5-trifluoromethyl-7H-thieno[3,2-b]pyran-3-carboxamide, 7-oxo-5-phenyl-N-{3-[4-[2-(2,2,2-trifluoroethoxy)phenyl]-1-piperazinyl]propyl}-7H-thieno[3,2-b]pyran-3-carboxamide, N-{3-[4-[2-methoxy-5-(2,2,2-trifluoroethoxy)phenyl]-1-piperazinyl]propyl}-7-oxo-5-phenyl-7H-thieno[3,2-b]pyran-3-carboxamide, and N-{3-[4-[4-fluoro-2-(2,2,2-trifluoroethoxy)phenyl]-1-piperazinyl]propyl}-7-oxo-5-phenyl-7H-thieno[3,2-b]pyran-3-carboxamide.
- 8. A pharmaceutical composition comprising a compound according to any one of claims 1-7 and a pharmaceutically acceptable diluent or carrier.
- 9. A process for producing the compound according to claim 1 comprising the steps of condensing a 7-oxo-7H-thieno[3,2-b]pyran-3-carboxylic acid derivative of the general formula
- 10. A process according to claim 9 wherein said condensation is carried out in the presence of a condensing agent chosen from the group consisting of dicyclohexyl carbodiimide and diethyl cyanophosphonate.
- 11. A process according to claim 10 wherein said condensation is carried out in the presence of a promoting agent chosen from the group consisting of N-hydroxysuccinimide, 4-dimethylaminopyridine and N,N′-carbonyldiimidazole.
- 12. A process according to claim 9 wherein said condensation is carried out in a solvent chosen from the group consisting of polar aprotic and chlorinated solvents.
- 13. A process according to claim 9 wherein said condensation is carried out at a temperature within the range of about 10 to about 140° C.
- 14. A process for producing the compound according to claim 1 comprising the steps of condensing a 7-oxo-7H-thieno[3,2-b]pyran-3-carboxylic acid derivative of the general formula 1,
- 15. A process according to claim 14 wherein said condensation of said 7H-thieno[3,2-b]pyran-3-carboxylic acid derivative 1 and said amine of the formula H2NCH2(CH2)nCH2X is performed in the presence of a condensing agent chosen from the group consisting of dicyclohexylcarbodiimide and diethyl cyanophosphonate.
- 16. A process according to claim 15 wherein said condensation step is carried out in the presence of a catalyst chosen from the group consisting of N-hydroxysuccinimide, 4-dimethylaminopyridine and N,N′-carbonyldiimidazole.
- 17. A process according to claim 14 wherein said condensing step is carried out optionally in a solvent chosen from a group consisting of aprotic solvent and chlorinated solvent.
- 18. A process according to claim 14 wherein said condensation is accomplished at a temperature within the range of 10 to about 140° C.
- 19. A process according to claim 14 wherein the reaction of a compound of formula 3 wherein X is a leaving group chosen from the group consisting of halogen, alkylsulphonyloxy, arylsulphonyloxy, and phenylpiperazine derivative 8 is performed in the presence of potassium carbonate.
- 20. A process according to claim 19 wherein said reaction is performed in the absence of solvent.
- 21. A process according to claim 19 wherein said reaction is performed in a solvent chosen from the group consisting of dimethylformamide, acetonitrile and methanol.
- 22. A process according to claim 19 wherein said reaction is performed at a temperature within the range of about 20 to about 200° C.
- 23. A method for preventing contractions of the urethra and lower urinary tract, the method comprising administering a compound according to any one of claims 1-7 to a mammal including humans in need of such treatment in an amount effective for preventing said contractions.
- 24. A method for preventing contractions of the urethra and lower urinary tract, the method comprising administering a pharmaceutical composition according to claim 8 to a mammal including humans in need of such treatment in an amount effective for preventing said contractions.
- 25. A method according to claim 23 wherein the administration of said compound causes limited effects on the blood pressure of said mammal including humans.
- 26. A method according to claim 24 wherein the administration of said compound causes limited effects on the blood pressure of said mammal including humans.
- 27. A method for blocking α1 adrenergic receptor, the method comprising releasing in the environment of said receptors an effective amount of a compound according to any one of claims 1-7 to relieve diseases associated with overactivity of said receptors.
- 28. The method for of claim 27 wherein the compound is released in the environment of said receptors from a pharmaceutically acceptable diluent or carrier.
- 29. A method according to claim 27 in which the releasing of the compound in the environment of said receptors is carried out by administering the compound to a mammal including a human possessing said receptor.
- 30. A method according to claim 28 in which release of the compound to the environment of said receptors is carried out by administering the pharmaceutical formulation to a mammal including a human possessing said receptors.
- 31. A method for the treatment of a patient suffering from benign prostatic hyperplasia, the method comprising administering an effective amount of a compound according to any one of claims 1-7 to a patient in need of such treatment.
- 32. A method for the treatment of a patient suffering from benign prostatic hyperplasia, the method comprising administering an effective amount of a pharmaceutical composition according to claim 8 to a patient in need of such treatment.
- 33. A method for the treatment of a patient suffering from excessive intraocular pressure, the method comprising administering an effective amount of a compound according to any one of claims 1-7 to a patient in need of such treatment.
- 34. A method for the treatment of a patient suffering from excessive intraocular pressure, the method comprising administering an effective amount of a pharmaceutical composition according to claim 8 to a patient in need of such treatment.
- 35. A method for the treatment of a patient suffering from cardiac arrhythmia, the method comprising administering an effective amount of a compound according to any one of claims 1-7 to a patient in need of such treatment.
- 36. A method for the treatment of a patient suffering from cardiac arrhythmia, the method comprising administering an effective amount of a pharmaceutical composition according to claim 8 to a patient in need of such treatment.
- 37. A method for the treatment of a patient suffering from erectile dysfunction, the method comprising administering an effective amount of a compound according to any one of claims 1-7 to a patient in need of such treatment.
- 38. A method for the treatment of a patient suffering from erectile dysfunction, the method comprising administering an effective amount of a pharmaceutical composition according to claim 8 to a patient in need of such treatment.
- 39. A method for the treatment of a patient suffering from sexual dysfunction, the method comprising administering an effective amount of a compound according to any one of claims 1-7 to a patient in need of such treatment.
- 40. A method for the treatment of a patient suffering from sexual dysfunction, the method comprising administering an effective amount of a pharmaceutical composition according to claim 8 to a patient in need of such treatment.
- 41. A method for inhibiting cholesterol synthesis in a patient, the method comprising administering an effective amount of a compound according to any one of claims 1-7 to a patient in need of such treatment.
- 42. A method for inhibiting cholesterol synthesis in a patient, the method comprising administering an effective amount of a compound according to claim 8 to a patient in need of such treatment.
- 43. A method for reducing sympathetically mediated pain in a patient, the method comprising administering an effective amount of a compound according to any one of claims 1-7 to a patient in need of such treatment.
- 44. A method for reducing sympathetically mediated pain in a patient, the method comprising administering an effective amount of a pharmaceutical composition according to claim 8 to a patient in need of such treatment.
- 45. A method for reducing lower urinary tract symptoms in a patient, the method comprising administering an effective amount of a compound according to any one of claims 1-7 to a patient in need of such treatment.
- 46. A method for reducing lower urinary tract symptoms in a patient, the method comprising administering an effective amount of a pharmaceutical composition according to claim 8 to a patient in need of such treatment.
- 47. The method according to claim 45 wherein said patient is a female.
- 48. The method according to claim 46 wherein said patient is a female.
- 49. The method according to claim 45 further comprising administering an anticholinergic compound.
- 50. The method according to claim 46 further comprising administering an anticholinergic compound.
- 51. The method according to claim 47 further comprising administering an anticholinergic compound.
- 52. The method according to claim 48 further comprising administering an anticholinergic compound.
- 53. The method according to claim 49 wherein said anticholinergic compound is chosen from the group consisting of tolterodine, oxybutimin, darifenacin, alvameline, and temiverine.
- 54. The method according to claim 50 wherein said anticholinergic compound is chosen from the group consisting of tolterodine, oxybutinin, darifenacin, alvameline, and temiverine.
- 55. The method according to claim 51 wherein said anticholinergic compound is chosen from the group consisting of tolterodine, oxybutinin, darifenacin, alvameline, and temiverine.
- 56. The method according to claim 52 wherein said anticholinergic compound is chosen from the group consisting of tolterodine, oxybutinin, darifenacin, alvameline, and temiverine.
- 57. A method for reducing neurogenic lower urinary tract dysfunction in a patient, the method comprising administering an effective amount of a pharmaceutical composition according to any of claims 1-7 to a patient in need of such treatment.
- 58. A method for reducing neurogenic lower urinary tract dysfunction in a patient, the method comprising administering an effective amount of a pharmaceutical composition according to claim 8 to a patient in need of such treatment.
- 59. The method according to claim 57 further comprising administering an anticholinergic compound.
- 60. The method according to claim 58 further comprising administering an anticholinergic compound.
- 61. The method according to claim 59 wherein said anticholinergic compound is chosen from the group consisting of tolterodine, oxybutinin, darifenacin, alvameline, and temiverine.
- 62. The method according to claim 60 wherein said anticholinergic compound is chosen from the group consisting of tolterodine, oxybutinin, darifenacin, alvameline, and temiverine.
Priority Claims (1)
Number |
Date |
Country |
Kind |
MI 99A 001704 |
Jul 1999 |
IT |
|
Parent Case Info
[0001] The enclosed application is based on Provisional Patent Application Seri al No. 60/179,423. Applicants claim the benefit of the filing date of the aforesaid Provisional Application under 35 U.S.C. §119(e)(1).
Provisional Applications (1)
|
Number |
Date |
Country |
|
60179423 |
Jan 2000 |
US |
Divisions (1)
|
Number |
Date |
Country |
Parent |
09627766 |
Jul 2000 |
US |
Child |
09931153 |
Aug 2001 |
US |