Benzopyran derivatives, processes for their preparation and...

C - Chemistry – Metallurgy – 07 – D

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C07D 405/04 (2006.01) C07D 311/22 (2006.01) C07D 311/70 (2006.01) C07D 311/72 (2006.01) C07D 413/04 (2006.01) C07D 417/04 (2006.01) C07D 493/04 (2006.01)

Patent

CA 1336835

Benzopyran derivatives of the general formula I Image (I) in which R1 and R2 which may be identical or different, denote hydrogen, C1-6-alkyl, C3-6-branched alkyl, C3-7-cycloalkyl or, together with the carbon atom enclosed by them, denote C3-7-spiroalkyl, R3 denotes hydroxyl, C1-8-alkoxy, formyloxy, C1-6-alkylcar- bonyloxy, C1-8-alkoxycarbonyloxy, C1-8-monoalkylaminocar- bonyloxy or C1-8-dialkylaminocarbonyloxy, where the C1-8- alkyl or alkoxy groups may both be linear or branched, and R4 stands for hydrogen or R3 and R4 together form a bond, R5 denotes a heterocycle of the formula A Image (A) where n stands for 1, 2, 3 or 4, or a heterocycle of the formula B Image (B) where Y stands for oxygen, sulphur, unsubstituted amino -NH-, substituted amino -NR7- and R7 denotes straight- chain C1-9-alkyl, branched C3-7-alkyl, C3-7-cycloalkyl, straight-chain or branched C1-9-alkyl substituted by C3-7- cycloalkyl,C1-8-alkylcarbonyl, C1-8-alkoxycarbonyl,benzyl, triphenylmethyl, phenyl, benzyloxycarbonyl, phenylcar- bonyl or benzylcarbonyl or R5 denotes a heterocycle of the formula C Image (C) where X stands for oxygen or sulphur and n stands for 1, 2, 3 or 4, or a heterocycle of the formula D Image (D) where m denotes 0, 1 or 2 and k denotes 1, 2 or 3, but in such a way that (m + k) is 1, 2 or 3 and furthermore X and Y have the meaning indicated for the formulae B and C, or a heterocycle of the formula E Image (E) where Z stands for cyanimino N-CN, cis or trans nitro- methylidene (c/t) CH-NO2 or nitroimino N-NO2, Y has the abovementioned meaning and p denotes 2 or 3, and R5, depending on R5, stands for the two classes of substi- tuents R6' and R6", where, if R5 denotes a heterocycle A, B, C or D, R6 stands for the substituent class R6' and R6' denotes difluoromethoxy, trifluoromethoxy, trifluoro- ethoxy, tetrafluoroethoxy, difluoromethylthio, difluoro- methylsulphinyl, difluoromethylsulphonyl, trifluoro- methylthio,trifluoromethylsulphinyl,trifluoromethylsul- phonyl, trifluoroethylthio, trifluoroethylsulphinyl or trifluoroethylsulphonyl, or, if R5 denotes the heterocycle E, R6 stands for the preceding substituent class R6' and for the substituent class R6" and R6" denotes cyano, nitro, C1-6-alkyl, C3-8-cycloalkyl, formyl and C1-6-alkylcarbonyl, where the heterocycle R5 is in the trans position to the radical R3 if R3 and R4 do not together denote a bond, but R4 stands for hydrogen, and their salts and acid addition salts, tautomers and optical isomers. The compounds are therapeutically active compounds.

604894

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