6-DIMETHYLAMINOMETHYL-1-PHENYLCYCLOHEXANE COMPOUNDS AS PHARMACEUTICALLY ACTIVE SUBSTANCES AND METHOD OF THEIR SYNTHESIS (VARIANTS) Russian patent published in 2002 - IPC

FIELD: organic chemistry, chemical technology, pharmacy. SUBSTANCE: invention relates to novel 6-dimethylaminomethyl-1-phenylcyclohexane compounds of the general formula (I) as bases or their physiologically acceptable salts eliciting analgetic activity and designated for preparing a pharmaceutical composition and to methods of their synthesis. In general formula (I) radicals have the following values: R¹ means H, OH, Cl or F; R² and R³ are identical or different and mean H, C₁-C₄-alkyl, CF₃, OH, OCH₂-C₆H₅, O-C₁-C₄-alkyl under condition that at least one of radicals R² or R³ means H; R⁴ means H, CH₃, CO-(OC₁-C₅-alkyl), CO-NH-C₆H₄-C₁-C₃-alkyl, CO-C₆H₄-R⁵, CO-C₁-C₅-alkyl, CO-CHR⁶-NHR⁷ or unsubstituted pyridyl or phenyl group or which are substituted with C₁-C₄-alkyl; R⁵ means OC(O)-C₁-C₃-alkyl in orthoposition or CH₂-N(R⁸)₂ in meta- or para-position being both radicals R⁸ in common with N-atom mean 4-morpholine radical; and R⁶,R⁷ are identical or different and mean H or C₁-C₆-alkyl under condition that if both radicals R² and R³ mean H then R⁴ is not CH_3/ if R¹ means H, OH or Cl; either R⁴ is not H if R¹ means OH. Invention describes also different methods of synthesis of compounds of the formula (I). For example, for synthesis of compounds where R¹ means OH dimethytlaminoketon of the formula (II) is subjected for interaction with organometallic compound of the formula (III) or dimethylaminoketon with spirocyclic acetal group of the formula (V) is subjected for interaction with organometallic compound of the formula (III) to yield the compound of the formula (VI) and the latter is converted to the keton compound (VIII) by deacetylation followed by reduction with alkaline metal complex hydride to the compound of the formula (I) which is converted to alkaline metal salt and then to the corresponding O-alkyl- or O-benzyl derivative. Invention describes also methods of synthesis of compounds where R¹ means H or compounds where R¹ means F. EFFECT: new compounds indicated above, improved methods of synthesis. 11 cl, 1 tbl