Thienopyranecarboxamide derivatives
AssigneeRecordati S.A., Chemical and Pharmaceutical Company
InventorsAmedeo Leonardi, Gianni Motta, Carlo Riva, Rodolfo Testa
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Abstract
The invention relates to novel N-(substituted phenyl)-N′-[ω-(5-substituted-7-oxo-7H-thieno[3,2-b]pyran-3-carbonylamino)alkyl]piperazines their N-oxides and pharmaceutically acceptable salts thereof. The compounds are endowed with enhanced selectivity for alpha1-adrenergic receptors and a low activity in lowering blood pressure. The compounds are useful in the treatment of obstructive syndromes of the lower urinary tract, including benign prostatic hyperplasia (BPH), and in the treatment of lower urinary tract symptoms (LUTS) and neutogenic lower urinary tract dysfunction (NLUTD), and other conditions. The compounds may be administered alone or in combination with an anticholinergic compound.
Claims14
A method for reducing lower urinary tract symptoms in a patient, the method comprising administering an effective amount of an anticholinergic compound and a compound represented by the general formula I
- wherein
- R is chosen from the group consisting of an aryl, cycloalkyl, and lower polyhaloalkyl group,
- R1 is chosen from the group consisting of lower alkyl, lower alkoxy, lower polyfluoroalkoxy, hydroxy and trifluoromethanesulfonyloxy group, each of R2 and R3 being independently chosen from the group consisting of a hydrogen, halogen, lower alkoxy, and lower polyfluoroalkoxy group, and
- n is 0, 1 or 2,
- or a piperazine-N-oxide thereof or a pharmaceutically acceptable salt of any of the foregoing.
A method for reducing lower urinary tract symptoms in a patient comprising administering an effective amount of an anticholinergic compound and a compound selected from the group consisting of
- 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.
A method for reducing neurogenic lower urinary tract dysfunction in a patient, the method comprising administering an effective amount of an anticholinergic compound and a compound represented by the general formula I
- wherein
- R is chosen from the group consisting of an aryl, cycloalkyl, and lower polyhaloalkyl group,
- R1 is chosen from the group consisting of lower alkyl, lower alkoxy, lower polyfluoroalkoxy, hydroxy and trifluoromethanesulfonyloxy group, each of R2 and R3 being independently chosen from the group consisting of a hydrogen, halogen, lower alkoxy, and lower polyfluoroalkoxy group, and
- n is 0, 1 or 2,
- or a piperazine-N-oxide thereof or a pharmaceutically acceptable salt of any of the foregoing.
A method for reducing neurogenic lower urinary tract dysfunction in a patient comprising administering an effective amount of an anticholinergic compound and a compound selected from the group consisting of
- 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.
Dependencies are inferred from the claim text.