METHODS FOR GLYCOSGINOPHYLIPIDS OBTAINING AND THEIR APPLICATION Russian patent published in 2017 - IPC C07H15/06 A61K39/39 C07H15/04 C07H15/18 A61P31/04 A61P31/12 A61P35/00 

FIELD: pharmacology.

SUBSTANCE: method for preparation of a compound of formula , where R₁ is OH, X is C₈ alkylene, R₃ is OH or H, R₄ is OH or H, R₅ is aryl, substituted aryl, heteroaryl, or substituted heteroaryl, provided that when R₃ is H and R₄ is H, then R₅ is phenyl substituted with one or two groups independently selected from -F, -Cl, -Br, -OCH₃, -OCH(CH₃)₂, -OPh, -OPh(4-F), 2-(5-F)-pyridinyl, -CF₃, -NO₂, -N(CH₃)₂ and 3-(6-F)-O-pyridinyl; or R₅ is pyridinyl substituted by a group independently selected from -F- or -OPh (4-F); when R₃ is H and R₄ is OH, then R₅ is phenyl substituted by a group independently selected from -F- or -OCH₃, or R₅ is phenyl substituted by two -F; when R₃ is OH and R₄ is OH, then R₅ is phenyl substituted by one or two groups independently selected from -F or -OCH₃; includes: (a) formula compound reacting with a formula compound in the presence of Lewis acid to form a formula compound, wherein PG is a hydroxyl protecting group and LG is a thiol-containing leaving group of the formula:

, , or ; (b) formula (5) compound reduction to obtain a formula compound; (c) formula (3) compound combination with a formula compound, where X is C₈ alkylene or C₈ alkenylene to provide a formula compound and deprotection of the formula (2) compound, where PG is a hydroxyl protecting group, by hydrogen under hydrogenation catalysis conditions to obtain the formula (1) compound.

EFFECT: new compounds, effective as ligands for natural killer T cells, new efficient methods for their production and new antiviral, antibacterial, antineoplastic agents based on them are proposed.

23 cl, 39 ex, 1 tbl, 9 dwg