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US 2008/0167316 A1Published application
6-Heteroaryl-1,2,3,4,4A, 10B-Hexahydrophenanthridines as Pde4-Inhibitors for the Treatment of Inflammatory Disorders
AssigneeAltana Pharma AG
InventorsUlrich Kautz, Beate Schmidt, Dieter Flockerzi, Maria Vittoria Chiesa, Armin Hatzelmann, Christof Zitt, Adrea Wohlsen, Degenhard Marx, Hans-Peter Kley
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Abstract
Compounds of a certain formula I in which R1, R2, R3, R31, R4, R5, R51 and Har have the meanings indicated in the description, are novel effective PDE4 inhibitors.
Claims13
A compound of formula I,
- in which
- either
- R1 is hydroxyl, 1-4C-alkoxy, 3-7C-cycloalkoxy, 3-7C-cycloalkylmethoxy, or completely or predominantly fluorine-substituted 1-4C-alkoxy, and
- R2 is 2,2-difluoroethoxy,
- or
- R1 is 2,2-difluoroethoxy, and
- R2 is hydroxyl, 1-4C-alkoxy, 3-7C-cycloalkoxy, 3-7C-cycloalkylmethoxy, or completely or predominantly fluorine-substituted 1-4C-alkoxy, and
- 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;
- Har is optionally substituted by R6 and/or R7 and/or R8, and is a 5- to 10-membered monocylic or fused bicyclic unsaturated or partially saturated heteroaryl radical comprising 1 to 4 heteroatoms independently selected from the group consisting of oxygen, nitrogen and sulfur, in which
- R6 is halogen, 1-4C-alkyl, 1-4C-alkoxy, 1-4C-alkoxy-2-4C-alkoxy, 1-4C-alkylthio, sulfanyl, cyano, 1-4C-alkoxycarbonyl, carboxyl, hydroxyl, oxo, -A-N(R61)R62, pyridyl, or completely or partially fluorine-substituted 1-4C-alkyl, in which
- A is a bond or 1-4C-alkylene,
- R61 is hydrogen or 1-4C-alkyl,
- R62 is hydrogen or 1-4C-alkyl,
- or R61 and R62 together and with inclusion of the nitrogen atom, to which they are attached, form a heterocyclic ring Het1, in which
- Het1 is optionally substituted by R611, and is a 3- to 7-membered saturated or unsaturated monocyclic heterocyclic ring radical comprising the nitrogen atom, to which R61 and R62 are bonded, and optionally one to three further heteroatoms independently selected from the group consisting of oxygen, nitrogen and sulfur, in which
- R611 is 1-4C-alkyl,
- R7 is 1-4C-alkyl, 1-4C-alkoxy, 1-4C-alkoxy-2-4C-alkoxy, 1-4C-alkylthio, sulfanyl, hydroxyl, oxo, amino or mono- or di-1-4C-alkylamino,
- R8 is halogen, 1-4C-alkyl or 1-4C-alkoxy,
- or a salt, N-oxide or salt of an N-oxide thereof.
22 more elements
(canceled)
(canceled)
Dependencies are inferred from the claim text.