Back to results
US 6,476,025 B1Granted
Phenylphennanthridines with PDE-IV inhibiting activity
AssigneeAltana Pharma AG
InventorBeate Gutterer
Life of this patent
Estimating the term…
Abstract
Compounds of formula (I), in which R1, R2, R3, R31, R4, R5, R51, R6, R13 and R20 have the meaning indicated in the description, are novel active bronchial therapeutics
Claims10
A compound of formula I,
- in which
- R1 is hydroxyl, 1-4C-alkoxy, 3-7C-cycloalkoxy, 3-7C-cycloalkylmethoxy or completely or predominantly fluorine-substituted 1-4C-alkoxy,
- R2 is hydroxyl, 1-4C-alkoxy, 3-7C-cycloalkoxy, 3-7C-cycloalkylmethoxy or completely or predominantly fluorine-substituted 1-4C-alkoxy,
- or in which
- R1 and R2 together are a 1-2C-alkylenedioxy group,
- R3 is hydrogen or 1-4C-alkyl,
- R31 is hydrogen or 1-4C-alkyl,
- or in which
- R3 and R31 together are a 1-4C-alkylene group,
- R4 is hydrogen or 1-4C-alkyl,
- R5 is hydrogen,
- R51 is hydrogen,
- or in which
- R5 and R51 together represent an additional bond,
- R6 is O-R7, S—R8, C(O)—R9, CH2—R10, S(O)2-aryl, O—S(O)2—R11, pyrrolidin-1-yl, pyrrolidin-1-yl-2-one, pyrrolidin-1-yl-2,5-dione, piperidin-1-yl, piperidin-1-yl-2-one or piperidin-1-yl-2,6-dione, where
- R7 is 3-7C-cycloalkyl, 3-7C-cycloalkylmethyl, 1-4C-alkoxy-1-4C-alkyl, aryl or phenyl-1-4C-alkyl,
- R8 is hydrogen, 1-4C-alkyl, 1-4C-alkylcarbonyl, arylcarbonyl, trifluoromethyl, difluoromethyl, trichloromethyl or phenyl,
- R9 is 1-4C-alkyl, 3-7C-cycloalkyl, 3-7C-cycloalkylmethyl, 1-pyrrolidinyl, 1-piperidinyl, 1-piperazinyl, 4-methylpiperazinyl, 4-morpholinyl or aryl,
- R10 is hydroxyl, halogen, cyano, carboxyl, 1-4C-alkoxy, phenoxy, 1-4C-alkoxycarbonyl, aminocarbonyl, mono- or di-1-4C-alkylaminocarbonyl, N(R15)R16 or 1-4C-alkylcarbonylamino, and
- R11 is 1-4C-alkyl, amino, mono- or di-1-4C-alkylamino or aryl, aryl is phenyl, pyridyl or R12-substituted phenyl, where
- R12 is hydroxyl, halogen, carboxyl, nitro, amino, cyano, 1-4C-alkyl, trifluoromethyl, 1-4C-alkoxy, 1-4C-alkoxycarbonyl, 1-4C-alkylcarbonylamino, 1-4C-alkylcarbonyloxy or aminocarbonyl,
- R13 is hydrogen, hydroxyl, halogen, cyano, nitro, amino, 1-4C-alkyl, trifluoromethyl, 1-4C-alkoxy, completely or predominantly fluorine-substituted 1-4C-alkoxy, phenyl, phenyl-1-4C-alkyl, C(O)—OR14, C(O)—N (R15)R16, N(R17)R18, S(O)2—R19, S(O)2—N(R15)R16 or has one of the meanings of R6, where
- R14 is hydrogen, 1-4C-alkyl, 3-7C-cycloalkyl or 3-7C-cycloalkylmethyl,
- R15 is hydrogen, 1-4C-alkyl, 3-7C-cycloalkyl or 3-7C-cycloalkylmethyl,
- R16 is hydrogen, 1-4C-alkyl, 3-7C-cycloalkyl, 3-7C-cycloalkylmethyl or aryl,
- or where R15 and R16, together and including the nitrogen atom to which both are bonded, represent a 1-pyrrolidinyl, 1-piperidinyl, 1-piperazinyl, 4-methylpiperazin-1-yl, 1-hexahydroazepinyl or 4-morpholinyl radical,
- R17 is hydrogen, 1-4C-alkyl, S(O)2—R19 or S(O)2-aryl,
- R18 is 1-4C-alkyl, 1-4C-alkylcarbonyl, 3-7C-cycloalkylcarbonyl, 3-7C-cycloalkylmethylcarbonyl, S(O)2—R19 or S(O)2-aryl, and
- R19 is 1-4C-alkyl,
- R20 is hydrogen, hydroxyl, halogen, nitro, amino, 1-4C-alkyl, trifluoromethyl, 1-4C-alkoxy, completely or predominantly fluorine-substituted 1-4C-alkoxy, 3-7C-cycloalkoxy, 3-7C-cycloalkylmethoxy, CH2—R10, carboxyl, 1-4C-alkoxycarbonyl, 1-4C-alkylcarbonyloxy, 1-4C-alkylcarbonylamino or aminocarbonyl,
- or a pharmaceutically acceptable salt, an N-oxide, or a salt of an N-oxide of this compound.
28 more elements
Dependencies are inferred from the claim text.