Method of preparation of alpha-galactosyl ceramides compounds

A kind of compound and alkyl technology, applied in the field of preparing a class of 6"-deoxy-6-amino α-galactosylceramide

Active Publication Date: 2019-03-22
ABIVAX
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] These problems are major obstacles to scaling up the method according to WO 2007 / 118234

Method used

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  • Method of preparation of alpha-galactosyl ceramides compounds
  • Method of preparation of alpha-galactosyl ceramides compounds
  • Method of preparation of alpha-galactosyl ceramides compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0292] Process for preparing compound (Ia)

[0293] Batch (Ia) was prepared according to Good Manufacturing Practice for clinical trials. A detailed description of the synthetic steps follows.

[0294] Preparation of compound 1

[0295] After 7 synthetic steps, methyl 6-acetylamino-2,3,4-tri-O-benzyl-α-D-galactopyranoside (1) was prepared from commercially available (Indofine Chemical Company) 1,2,3,4-Di-O-isopropylidene-α-D-galactopyranose (XII):

[0296]

[0297] - activation of the alcohol function to a tosyl group from commercially available (XII),

[0298] - partial substitution of the tosyl group by phthalimide,

[0299] - cleavage of the alcohol protecting the isopropylidene group, methylation of the anomer position and purification on silica gel,

[0300] - cleaves the phthalimide ring to provide the free amine,

[0301] - acetalization of alcohols and amino groups,

[0302] - cleavage of acetyl esters, and

[0303] - Benzylation of the hydroxyl group and fina...

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Abstract

The invention relates to a method of preparation of alpha-galactosyl ceramides compounds of formula (I) comprising a step a) of glycosylation of a compound of formula (II) with a compound of formula (III).

Description

[0001] This application is a divisional application whose parent application is Chinese invention patent application 201380056606.0. technical field [0002] The invention relates to a method for preparing a class of 6"-deoxy-6-aminoα-galactosylceramides. Background technique [0003] The significance of α-galactosylceramide compounds (also known as α-GCs compounds) is especially fully explained in WO 2007 / 118234. α-GCs compounds have been found to potently stimulate natural killer T (NKT) cells both in vitro and in vivo. NKT cells have been implicated in the suppression of autoimmunity and transplant rejection, promotion of resistance to pathogens and promotion of tumor immunity. [0004] A natural glycolipid molecule, called KRN7000, is known to stimulate NKT cells in the presence of CD1d tetramers. However, the supply of KRN7000 derived from marine sponges is limited and this glycolipid has relatively low solubility in aqueous or organic solvents. [0005] Thus, a modi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/04C07H15/06C07H15/18C07H15/26C07D317/28C07H1/00
CPCC07H1/00C07H13/12C07H15/04C07H15/18C07H15/26C07H15/06C07D317/28A61P35/00A61P37/04Y02P20/55
Inventor V·瑟拉
Owner ABIVAX
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