FLUORINE-CONTAINING TEVINOL AND ORVINOL DERIVATIVES AND METHODS OF THEIR OBTAINING (VERSIONS) Russian patent published in 2014 - IPC C07D489/12 A61K31/485 A61P25/04 

FIELD: chemistry.

SUBSTANCE: invention relates to tevinol and orvinol derivatives of general formula I where R=OH; R¹=H, CF₃, C₁-C₄ alkyl, aryl, or (R+R¹) stands for O=; R²=H, CH₃; R³=H, CH₃; R⁴=CH₃, cyclopropylmethyl, allyl; Z~Z=CH₂CH₂, CH=CH. Invention also relates to method of obtaining formula I derivatives. Method lies in trifluoromethylation of respective aldehyde with formation of 21,21,21-trifluorotevinol, further oxidation of formed fluorine-containing alcohol with formation of respective ketone, which under influence of reagent, selected from the group, including R¹Li, R¹MgX, CF₃Si(CH₃)₃, results in obtaining formula I tevinol derivatives. Orvinol derivatives are obtained by demethylation of tevinols.

EFFECT: formula I derivatives as ligands of opioid receptors with wide possibilities of varying their hydrophilic-hydrophobic balance.

9 cl, 16 ex