Patent TW-200540159-A (TW)
Title: Novel thio-containing hydroxy-6-phenylphenanthridines
Inventor: KAUTZ ULRICH
IPC: C07D221/12
Filed: 2005-03-10
Abstract: Compounds of a certain formula I, in which R1, R2, R3, R31, R4, R5, R6 and R7 have the meanings indicated in the description, are novel effective PDE4 inhibitors. (1). Compounds 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, either, in a first embodiment (embodiment a) according to the present invention, 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) according to the present invention, 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, in a first aspect (aspect 1) according to this invention, R7 is-S(O)2N(R8)R9, in which R8 is hydrogen, 1-4C-alkyl, 1-4C-alkoxy-2-4C-alkyl or 3-7C-cycloalkyl, R9 is hydrogen, 1-4C-alkyl or 1-4C-alkoxy-2-4C-alkyl, or R8 and R9 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 R81, and is a 3- to7-membered saturated monocyclic heterocyclic ring radical comprising the nitrogen atom, to which R8 and R9 are bonded, and optionally one further heteroatom selected from the group consisting of oxygen, nitrogen and sulfur, in which R81 is 1-4C-alkyl, or, in a second aspect (aspect 2) according to this invention, R7 is -A-N(R10)S(O)2-R11, in which A isabondor1-4C-alkylene, R10 is hydrogen or 1-4C-alkyl, R11 is 1-4C-alkyl, or R111-substituted phenyl, in which R111 is halogen or 1-4C-alkyl, or, in a third aspect (aspect 3) according to this invention, R7 is-S(O)nR12, in which n is O, 1 or 2, R12 is 1-4C-alkyl, and the salts, the N-oxides and the salts of the N-oxides of these compounds. (2). Compounds of formula I according to claim 1 in which R1 is 1-2C-alkoxy, 3-5C-cycloalkoxy, 3-5C-cycloalkylmethoxy, 2,2-difluoroethoxy, or completely or predominantly fluorine-substituted 1-2C-alkoxy, R2 is 1-2C-alkoxy, 3-5C-cycloalkoxy, 3-5C-cycloalkylmethoxy, 2,2-difluoroethoxy, or completely or predominantly fluorine-substituted 1-2C-alkoxy, R3 is hydrogen, R31 is hydrogen, either, in a first embodiment (embodiment a) according to the present invention, R4 is-O-R41, in which R41 is hydrogen or 1-7C-alkylcarbonyl, R5 is hydrogen, or, in a second embodiment (embodiment b) according to the present invention, R4 is hydrogen, and R5 is-O-R51, in which R51 is hydrogen or 1-7C-alkylcarbonyl, R6 is hydrogen or 1-4C-alkyl, in a first aspect (aspect 1) according to this invention, R7 is -S(O)2N(R8)R9, in which R8 is hydrogen, 1-4C-alkyl, 1-4C-alkoxy-2-4C-alkyl or 3-7C-cycloalkyl, R9 is hydrogen, 1-4C-alkyl or 1-4C-alkoxy-2-4C-alkyl,