Coumarin derivatives, process for their preparation, their...

C - Chemistry – Metallurgy – 07 – D

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260/302, 167/43,

C07D 417/02 (2006.01) A61K 31/37 (2006.01) A61K 31/395 (2006.01) C07D 263/34 (2006.01) C07D 277/32 (2006.01) C07D 277/56 (2006.01) C07D 311/16 (2006.01) C07D 405/10 (2006.01) C07D 417/04 (2006.01) G01N 21/64 (2006.01) G01N 33/52 (2006.01) G01N 33/543 (2006.01)

Patent

CA 2030243

Coumarin derivatives, process for their preparation, their use and thiazolyl-acetic acid derivatives as intermediates A b s t r a c t Coumarin derivatives of the formula Image (I), in which R1 denotes hydrogen or cyano, R2 represents phenyl or thiazolyl bonded in the 2-, 4- or 5-position, where phenyl is substituted by nitro, cyano, amino, -NH-C1-C4-alkyl, -C1-C4-alkyl-NH2, -C1-C4-alkyl-NH-C1-C4- alkyl, carboxyl, C1-C4-alkoxy-carbonyl, C1-C4-alkyl- carbonyloxy, hydroxyl, C1-C4-alkylamino-carbonyl or C1-C4- alkylcarbonyl-amino and can additionally be substituted by C1-C4-alkyl, fluorine, chlorine or bromine, and where thiazolyl is monosubstituted or disubstituted by chlor- ine, cyano, carboxyl or C1-C4-alkoxy-carbonyl, where, in the case of disubstitution, the two substituents may be different and where the 4- and the 5-position can to- gether carry a fused benzene ring which can be substitu- ted by carboxyl, amino or hydroxyl, R3 denotes hydrogen, C1-C4-alkyl or C1-C4-alkoxy- Le A 27 716-US carbonyl-C1-C4-alkyl and R4 represents hydrogen, C1-C4-alkyl or phenylsulphonyl, where C1-C4-alkyl can be substituted by hydroxyl, amino, carboxyl or C1-C4-alkoxy-carbonyl and phenyl can be monosubstituted or disubstituted by chlorine, bromine or C1-C4-alkyl, where furthermore R3 and R4, together with the N atom which they substitute, can denote a morpholine ring, a piperazine ring or a triazole ring which can carry one or two substituents from the group comprising methyl, ethyl and phenyl, and where furthermore one of the radicals R2, R3 and R4 denotes or carries a primary or secondary amino group, the hydroxyl group, the carboxyl group or the C1-C4- alkoxy-carbonyl group or can be converted into such a qroup by hydrolysis or hydrogenation, are suitable for dyeing biologically active compounds. Le A 27 716-US

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