Patent EP-0213571-A2 (EP)
Inventor: GEISS KARL-HEINZ DR
IPC: C07D403/12
Filed: 1986-08-22
Abstract: Compounds of the formula I <IMAGE>  in which R<1> and R<2> independently of one another denote a hydrogen atom or a C1-C12-alkyl, C3-C12-alkenyl or C3-C12-cycloalkyl radical which can be substituted by a phenyl or naphthyl radical which, in turn, can be substituted by 1 or 2 C1-3-alkyl or C1-3-alkoxy groups or by 1 or 2 fluorine, chlorine or bromine atoms or by a trifluoromethyl, carboxyl, (C1-5-alkoxy)-carbonyl, cyano or C1-4-acylamido group, or by a 5-membered aromatic ring having 1 to 3 nitrogen atoms or an oxygen or sulphur atom and optionally 1-2 nitrogen atoms, or by a 6-membered aromatic ring having 1 to 3 nitrogen atoms, where these heteroaromatic rings optionally carry 1 to 3 C1-3-alkyl groups, or R<1> and R<2>, together with the nitrogen atom, form a saturated heterocyclic ring having 4 to 12 ring members which is substituted by a phenyl and/or a hydroxyl, C1-4-acyl, (C1-5-alkoxy)-carbonyl, nitrile, n-phenyl-n-(C1-4-acyl)amino or n-benzamido group or a benzimidazolin-2-on-1-yl radical and/or by 1 to 3 C1-4-alkyl groups or can carry a fused benzene ring, R<3>, R<4> and R<5> independently of one another denote hydrogen atoms or C1-3-alkyl groups, where R<4> and R<5>, together with the double bond, can also denote a benzene ring, A denotes a C2-8-alkylene radical, which can be olefinically or acetylenically monounsaturated and in which a carbon atom can be replaced by an oxygen atom, a sulphur atom or a phenylene group,  B denotes one of the groups B<1> to B<6>: <IMAGE> in which  E denotes S, CH-NO2 or N-CN, R<6> denotes a hydrogen atom or a C1-3-alkyl radical which can be substituted by a 5-membered aromatic ring having 1 to 3 nitrogen atoms or an oxygen or sulphur atom and optionally 1-2 nitrogen atoms or a 6-membered aromatic ring having 1 to 3 nitrogen atoms, where these heteroaromatic rings optionally carry 1 to 3 C1-3-alkyl groups, or can be substituted by a hydroxyl or C1-4-alkoxy group,  R<7> denotes a hydrogen atom or a C1-3-alkyl radical,  R<8> denotes an amino group or the radical CH2OR<1><2>, in which R<1><2> represents a hydrogen atom, a C1-3-alkyl radical, a C1-6-acyl group, the benzoyl group, or the tetrahydrofuran-2-yl or tetrahydropyran-2-yl radical, R<9> denotes a C1-6-alkyl radical or a phenyl group which can each be substituted by 1 or 2 C1-3-alkyl, or C1-3-alkoxy groups or chlorine or bromine atoms or by a methylenedioxo radical, or denotes a 5-membered aromatic ring having 1 to 3 nitrogen atoms or an oxygen or sulphur atom and optionally 1-2 nitrogen atoms or a 6-membered aromatic ring having 1 to 3 nitrogen atoms, where these heteroaromatic rings optionally carry 1 to 3 C1-3-alkyl groups, R<1><0> and R<1><1> denote hydrogen atoms or C1-3-alkyl radicals which can be substituted by a phenyl group which can each in turn be substituted by 1 or 2 C1-3-alkyl or C1-3-alkoxy groups or chlorine or bromine atoms, or by a 5-membered aromatic ring having 1 to 3 nitrogen atoms or an oxygen or sulphur atom and optionally 1-2 nitrogen atoms or a 6-membered aromatic ring having 1 to 3 nitrogen atoms, where these heteroaromatic rings optionally carry 1 to 3 C1-3-alkyl groups, or by a hydroxyl or C1-3-alkoxy group,  m denotes the number 0, 1 or 2 and Ar represents a fused benzene or thiophene ring, and their physiologically tolerated salts, and the compounds or their salts as therapeutic agents containing active compound.