2-heteroarylcarboxylic acid amides
AssigneeBayer Schering Pharma Aktiengesellschaft
InventorsMartin Hendrix, Frank-Gerhard Böβ, Christina Erb, Timo Fleβner, Marja van Kampen, Joachim Luithle, Christoph Methfessel, Welf-Burkhard Wiese
Life of this patent
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Abstract
The invention relates to novel 2-heteroarylcarboxamides, processes for their preparation, and their use for producing medicaments for the treatment and/or prophylaxis of diseases and for improving perception, concentration, learning and/or memory.
Claims56
A compound of the formula (I):
- in which
- R1 represents 1-azabicyclo[2.2.2]oct-3-yl,
- R2 represents hydrogen or C1-C6-alkyl,
- R3 represents hydrogen, halogen or C1-C6-alkyl,
- A represents oxygen or sulfur, and
- the ring B represents benzo, pyrimido, pyrimidazo or pyridazino which is substituted by a radical selected from the group consisting of halogen, C1-C6-alkanoyl, carbamoyl, cyano, trifluoromethyl, trifluoromethoxy, nitro, amino, C1-C6-acylamino, C1-C6-alkyl, C1-C6-alkyoxy, C1-C6-alkylthio, C1-C6-alkylamino, heteroarylcarbonylamino, arylcarbonylamino, C1-C6-alkylsulfonyl-amino, di(C1-C4-alkylsulfonyl)amino, arylsulfonylamino, di(arylsulfonyl)amino, C3-C6-cycloalkylcarbonylmethyl, 1,3-dioxa-propane-1,3-diyl, amino(hydroxyimino)methyl and benzo,
- or a salt, a hydrate or a hydrate of a salt thereof.
A compound of the formula Ia:
- in which
- R1 represents 1-azabicyclo[2.2.2]oct-3-yl,
- R2 represents hydrogen or C1-C6-alkyl,
- R3 represents hydrogen, halogen or C1-C6-alkyl,
- A represents oxygen or sulfur,
- and
- Z represents halogen, formyl, carbamoyl, cyano, trifluoromethyl, trifluoromethoxy, nitro, amino, formamido, acetamido, C1-C6-alkyl, C1-C6-alkyoxy, C1-C6-alkylthio, C1-C6-alkylamino, heteroaryl-carbonylamino, arylcarbonylamino, C1-C4-alkylsulfonylamino, di(arylsulfonyl)amino, C3-C6-cycloalkylcarbonylmethyl or amino(hydroxyimino)methyl,
- or a salt, a hydrate or a hydrate of a salt thereof.
N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-fluoro-1-benzofuran-2-carboxamide or a salt thereof.
N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-fluoro-1-benzothiophene-2-carboxamideor or a salt thereof.
N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5,7-difluoro-1-benzothiophene-2-carboxamide or a salt thereof.
N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-fluoro-1-benzofuran-2-carboxamide or a salt thereof.
N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-chloro-1-benzofuran-2-carboxamide or a salt thereof.
N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5,7-difluoro-1-benzofuran-2-carboxamide or a salt thereof.
N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-fluoro-1-benzothiophene-2-carboxamide or a salt thereof.
N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-chloro-1-benzothiophene-2-carboxamide or a salt thereof.
N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-cyano-1-benzothiophene-2-carboxamide or a salt thereof.
N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-trifluoromethyl-1-benzothiophene-2-carboxamide or a salt thereof.
A pharmaceutical composition comprising N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-fluoro-1-benzofuran-2-carboxamide or a salt thereof and a pharmaceutically acceptable carrier.
A pharmaceutical composition comprising N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-fluoro-1-benzothiophene-2-carboxamide or a salt thereof and a pharmaceutically acceptable carrier.
A pharmaceutical composition comprising N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5,7-difluoro-1-benzothiophene-2-carboxamide or a salt thereof and a pharmaceutically acceptable carrier.
A pharmaceutical composition comprising N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-fluoro-1-benzofuran-2-carboxamide or a salt thereof and a pharmaceutically acceptable carrier.
A pharmaceutical composition comprising N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-chloro-1-benzofuran-2-carboxamide or a salt thereof and a pharmaceutically acceptable carrier.
A pharmaceutical composition comprising N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5,7-difluoro-1-benzofuran-2-carboxamide or a salt thereof and a pharmaceutically acceptable carrier.
A pharmaceutical composition comprising N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-fluoro-1-benzothiophene-2-carboxamide or a salt thereof and a pharmaceutically acceptable carrier.
A pharmaceutical composition comprising N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-chloro-1-benzothiophene-2-carboxamide or a salt thereof and a pharmaceutically acceptable carrier.
A pharmaceutical composition comprising N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-cyano-1-benzothiophene-2-carboxamide or a salt thereof and a pharmaceutically acceptable carrier.
A pharmaceutical composition comprising N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-trifluoromethyl-1-benzothiophene-2-carboxamide or a salt thereof and a pharmaceutically acceptable carrier.
A hydrate of N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-fluoro-1-benzofuran-2-carboxamide or a salt thereof.
A hydrate of N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-fluoro-1-benzothiophene-2-carboxamide or a salt thereof.
A hydrate of N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5,7-difluoro-1-benzothiophene-2-carboxamide or a salt thereof.
A hydrate of N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-fluoro-1-benzofuran-2-carboxamide or a salt thereof.
A hydrate of N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-chloro-1-benzofuran-2-carboxamide or a salt thereof.
A hydrate of N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5,7-difluoro-1-benzofuran-2-carboxamide or a salt thereof.
A hydrate of N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-fluoro-1-benzothiophene-2-carboxamide or a salt thereof.
A hydrate of N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-chloro-1-benzothiophene-2-carboxamide or a salt thereof.
A hydrate of N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-cyano-1-benzothiophene-2-carboxamide or a salt thereof.
A hydrate of N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-trifluoromethyl-1-benzothiophene-2-carboxamide or a salt thereof.
A pharmaceutical composition comprising a hydrate of N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-fluoro-1-benzofuran-2-carboxamide or a salt thereof and a pharmaceutically acceptable carrier.
A pharmaceutical composition comprising a hydrate of N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-fluoro-1-benzothiophene-2-carboxamide or a salt thereof and a pharmaceutically acceptable carrier.
A pharmaceutical composition comprising a hydrate of N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5,7-difluoro-1-benzothiophene-2-carboxamide or a salt thereof and a pharmaceutically acceptable carrier.
A pharmaceutical composition comprising a hydrate of N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-fluoro-1-benzofuran-2-carboxamide or a salt thereof and a pharmaceutically acceptable carrier.
A pharmaceutical composition comprising a hydrate of N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-chloro-1-benzofuran-2-carboxamide or a salt thereof and a pharmaceutically acceptable carrier.
A pharmaceutical composition comprising a hydrate of N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5,7-difluoro-1-benzofuran-2-carboxamide or a salt thereof and a pharmaceutically acceptable carrier.
A pharmaceutical composition comprising a hydrate of N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-fluoro-1-benzothiophene-2-carboxamide or a salt thereof and a pharmaceutically acceptable carrier.
A pharmaceutical composition comprising a hydrate of N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-chloro-1-benzothiophene-2-carboxamide or a salt thereof and a pharmaceutically acceptable carrier.
A pharmaceutical composition comprising a hydrate of N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-cyano-1-benzothiophene-2-carboxamide or a salt thereof and a pharmaceutically acceptable carrier.
A pharmaceutical composition comprising a hydrate of N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-trifluoromethyl-1-benzothiophene-2-carboxamide or a salt thereof and a pharmaceutically acceptable carrier.
Dependencies are inferred from the claim text.