METHOD OF PRODUCING (2S,3S,4S,5R,6S)-3,4,5-TRIHYDROXY-6-(((4AR,10AR)-7-HYDROXY-1-PROPYL-1,2,3,4,4A,5,10,10A-OCTAHYDROBENZO[G]QUINOLIN-6-YL)OXY)TETRAHYDRO-2H-PYRAN-2-CARBOXYLIC ACID Russian patent published in 2024 - IPC C07D405/12 C07D455/06 A61K31/706 A61P25/16 C07H1/00 C07D221/06 

Abstract RU 2819919 C2

FIELD: chemistry.

SUBSTANCE: present invention relates to a method of producing (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(((4aR,10aR)-7-hydroxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolin-6-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid structural formula (Id) and salts thereof, used in treating neurodegenerative diseases, as well as to intermediate compounds from said method. Method of producing compound (Id) from compound (I) includes step 1 with reacting compound (I) or a salt thereof with a benzyl halide in an organic solvent, selected from acetonitrile, dimethylformamide or methyl isobutyl ketone in the presence of a base, to obtain compound (A2), step 2 with subjecting compound (A2) to a debenzylation reaction to obtain compound (A3) or a salt thereof, reacting compound (A3) or a salt thereof with (2S,3S,4S,5R,6R)-2-(methoxycarbonyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyltriacetate to obtain compound (A4) (step 3), reacting compound (A4) with an alkali metal hydroxide to obtain (A5-Y) (step 4) and step 5 with debenzylation of compound (A5-Y) to obtain compound (Id).

EFFECT: providing a method of producing the desired compound with high output and suitable for large-scale production.

24 cl, 7 dwg, 3 tbl, 10 ex

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RU 2 819 919 C2

Authors

Dzhukhl, Martin

Terkelsen, Frans, Dennis

Frikhed, Tobias, Gilling

Dates

2024-05-28Published

2020-05-19Filed