OXAZOLIDINE-BASED COMPOUND AND ANDROGEN RECEPTOR SELECTIVE AGONIST Russian patent published in 2019 - IPC C07D263/04 C07D263/06 C07D413/04 C07D413/12 A61K31/421 A61P15/00 

FIELD: chemistry.

SUBSTANCE: invention relates to a compound of the following chemical formula 1, an enantiomer, a diastereomer or a pharmaceutically acceptable salt thereof, where R₁ is a substitute of the following chemical formula 2 or chemical formula 3; R₂ is hydrogen, oxo or C₁-C₆alkyl; R₃ and R₄ each independently represents a substitute selected from a group consisting of hydrogen and C₁-C₆alkyl; R₅ and R₆ each independently represents a substitute selected from the group consisting of hydrogen, halogen and C₁-C₆alkyl; R₇ is cyano or nitro, and when R₇ is cyano and R₂ is H, then R₁ is X(CH₂)_nR₈ provided that if n is 0 and X is O, then R₈ does not represent H; C₁-C₆alkyl as R₃ value and R₆ contains one or more substitutes selected from a group consisting of hydrogen, hydroxy and halogen; chemical formula 2 is -X(CH₂)_nR₈, where X is O, N(H), S or S(O)₂, R₈ is hydrogen, piperidine, phenyl or pyridine, which can be substituted (substitutes are given in the claim), n is 0 or 1; chemical formula 3 represents structure (a), where Y is CH or N, m is integer 0, 1 or 2, R₉ represents a substitute selected from a group consisting of hydrogen, oxo, C₁-C₆alkyl, cyano, C(O)R₁₂, C(O)OR₁₂, C(O)NR₁₂R₁₃, S(O)₂R₁₂, NHC(O)R₁₃, NR₁₂R₁₃ and NHC(O)OR₁₂, R₁₂ and R₁₃ are given in the claim, and C₁-C₆alkyl contains one or more substitutes selected from a group consisting of hydrogen, hydroxy, halogen and cyano. Invention also relates to specific compounds: oxime (E)-4-(((2R,5S)-3-(3-methyl-4-nitrophenyl)-2-(trifluoromethyl)oxazolidin-5-yl)methoxy)benzaldehyde, 2-chloro-4-((2R,5S)-5-((4-((E)-(hydroxyimino)methyl)phenoxy)methyl)-2-(trifluoromethyl)oxazolidin-3-yl)benzonitrile, 2-chloro-4-((2R,5S)-5-((4-((E)-(hydroxyimino)methyl)phenoxy)methyl)-2-(trifluoromethyl)oxazolidin-3-yl)-3-methylbenzonitrile, 4-((2R,5S)-5-((4-((E)-(methoxyimino)methyl)phenoxy)methyl)-2-(trifluoromethyl)oxazolidin-3-yl)-2-(trifluoromethyl)benzonitrile, 4-((2R,5S)-5-((4-((E)-(hydroxyimino)methyl)phenoxy)methyl)-2-(trifluoromethyl)oxazolidin-3-yl)-2-(trifluoromethyl)benzonitrile, oxime(E)-4-(((2R,5S)-3-(4-nitro-3-(trifluoromethyl)phenyl)-2-(trifluoromethyl)oxazolidin-5-yl)methoxy)benzaldehyde, 4-((2R,5S)-5-((4-((E)-(hydroxyimino)methyl)-2-nitrophenoxy)methyl)-2-(trifluoromethyl)oxazolidin-3-yl)-2-(trifluoromethyl)benzonitrile, (2R,5S)-5-(1-acetylpiperidin-4-yl)-3-(4-cyano-3-(trifluoromethyl)phenyl)-2-(trifluoromethyl)oxazolidine-5-carboxamide or 4-((2R,5S)-5-(1-hydroxy-2-phenylethyl)-2-(trifluoromethyl)oxazolidin-3-yl)-2-(trifluoromethyl)benzonitrile. Invention relates to methods of producing the compounds given in the patent claim.

(chemical formula 1)

(structure a).

EFFECT: compounds of the invention are intended as a selective androgen receptor agonist.

12 cl, 6 tbl, 195 ex