SUBSTITUTED (R)-3-(4-METHYLCARBAMOYL-3-FLUOROPHENYLAMINO)-TETRAHYDRO-FURAN-3-ENE CARBOXYLIC ACIDS AND ESTERS THEREOF, METHOD FOR PRODUCTION AND USE THEREOF Russian patent published in 2014 - IPC C07D307/22 C07D491/107 C07F7/08 C07F7/10 

FIELD: chemistry.

SUBSTANCE: invention relates to novel substituted 3-(4-methylcarbamoyl-3-fluorophenylamino)tetrahydrofuran-3-ene carboxylic acid or esters thereof of general formula 1 and stereoisomers. The compounds of formula 1 are intermediate products in synthesis of androgen receptor inhibitors of formula A1, A2, A3, which are of interest as anticancer drugs. The invention also relates to methods of producing compounds of formula 1 and compounds of formulae A1, A2, A3. In general formula 1 R¹=H, C₁-C₄alkyl; R²=H, CH₂OCH₂CH₂Si(CH₃)₃. The method of producing compounds of formula (1) involves reacting compounds of general formula 2 with compounds 3(1) or 3(2) in dimethylformamide, K₂CO₃ while simultaneously adding copper iodide, water and triethylamine to the reaction mass. 2: By reacting compounds of formula 1, obtained using said method, with 4-isothiocyanato-2-trifluoromethylbenzonitrile in a mixture of dimethyl sulphoxide and ethyl acetate in ratio of 1:2 and at high temperature, compounds A1, A2, A3, whose structure is given in the claim, are obtained, respectively.

EFFECT: use of novel intermediate products improves output and stereoselectivity of the method of producing compounds A1, A2, A3.

4 cl, 6 ex