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US 2007/0191414 A1Published application
Novel isoamido-substituted hydroxy-6-phenylphenanthridines
AssigneeAltana Pharma AG
InventorUlrich Kautz
Life of this patent
Estimating the term…
Abstract
Compounds of the formula I in which the substituents have the definitions provided in the specification, are novel, effective PDE4 inhibitors.
Claims16
A compound of formula I,
- in which
- R1 is hydroxyl, 1-4C-alkoxy, 3-7C-cycloalkoxy, 3-7C-cycloalkylmethoxy, 2,2-difluoroethoxy, or completely or predominantly fluorine-substituted 1-4C-alkoxy,
- R2 is hydroxyl, 1-4C-alkoxy, 3-7C-cycloalkoxy, 3-7C-cycloalkylmethoxy, 2,2-difluoroethoxy, 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,
- wherein either, in a first embodiment (embodiment a)
- R4 is —O—R41, in which
- R41 is hydrogen, 1-4C-alkyl, 1-4C-alkoxy-1-4C-alkyl, hydroxy-2-4C-alkyl, 1-7C-alkylcarbonyl, or completely or predominantly fluorine-substituted 1-4C-alkyl, and
- R5 is hydrogen or 1-4C-alkyl,
- or, in a second embodiment (embodiment b)
- R4 is hydrogen or 1-4C-alkyl, and
- R5 is —O—R51, in which
- R51 is hydrogen, 1-4C-alkyl, 1-4C-alkoxy-1-4C-alkyl, hydroxy-2-4C-alkyl, 1-7C-alkylcarbonyl, or completely or predominantly fluorine-substituted 1-4C-alkyl,
- R6 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy,
- R61 is hydrogen, 1-4C-alkyl or 1-4C-alkoxy-2-4C-alkyl,
- R7 is Het1, Har1, 3-7C-cycloalkyl, or 1-4C-alkyl substituted by R8, in which
- Het1 is optionally substituted by R71 and is a monocyclic monocylic 3- to 7-membered fully saturated heterocyclic ring radical,
- which is bonded via a ring carbon atom to the carbonyl moiety of the —C(O)N(R61)- group, and
- which comprises one nitrogen atom and optionally one further heteroatom selected from the group consisting of nitrogen, oxygen and sulfur, and, optionally,
- to which ring one or two oxo groups are bonded, in which
- R71 is 1-4C-alkyl, or completely or partially fluorine-substituted 1-4C-alkyl,
- Har1 is optionally substituted by R72 and/or R73, and is a 5- or 6-membered monocyclic unsaturated heteroaryl radical comprising 1 to 4 heteroatoms independently selected from the group consisting of oxygen, nitrogen and sulfur, in which
- R72 is halogen, 1-4C-alkyl, 1-4C-alkoxy, 1-4C-alkoxy-2-4C-alkoxy, 1-4C-alkylthio, cyano, 1-4C-alkoxycarbonyl, carboxyl, hydroxyl, -A-N(R721)R722, pyridyl, or completely or partially fluorine-substituted 1-4C-alkyl, in which
- A is a bond or 1-4C-alkylene,
- R721 is hydrogen or 1-4C-alkyl,
- R722 is hydrogen or 1-4C-alkyl,
- or R721 and R722 together and with inclusion of the nitrogen atom, to which they are attached, form a heterocyclic ring Het2, in which
- Het2 is optionally substituted by R723, and is a 3- to 7-membered saturated or unsaturated monocyclic heterocyclic ring radical comprising the nitrogen atom, to which R721 and R722 are bonded, and optionally one to three further heteroatoms independently selected from the group consisting of oxygen, nitrogen and sulfur, in which
- R723 is 1-4C-alkyl,
- R73 is halogen, 1-4C-alkoxy, 1-4C-alkoxy-2-4C-alkoxy, 1-4C-alkylthio, hydroxyl, amino or mono- or di-1-4C-alkylamino,
- R8 is 1-4C-alkoxy, carbamoyl, carboxyl, 1-4C-alkoxycarbonyl, mono- or di-1-4C-alkylaminocarbonyl or —N(R81)R82, in which
- R81 is hydrogen, 1-4C-alkyl, carbamoyl, amidino or 1-4C-alkylcarbonyl,
- R82 is hydrogen or 1-4C-alkyl,
- or R81 and R82 together and with inclusion of the nitrogen atom, to which they are attached, form a heterocyclic ring Het3, in which
- Het3 is optionally substituted by R811, and is a 3- to 7-membered saturated monocyclic heterocyclic ring radical comprising the nitrogen atom, to which R81 and R82 are bonded, and optionally one further heteroatom selected from the group consisting of oxygen, nitrogen and sulfur, in which
- R811 is 1-4C-alkyl,
- or an enantiomer, salt, N-oxide, salt of an N-oxide or enantiomer of an N-oxide thereof.
36 more elements
(canceled)
13-14. (canceled)
Dependencies are inferred from the claim text.