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Novel synthesis of galactoside inhibitors

a technology of galactoside inhibitors and synthesis routes, which is applied in the field of new synthesis routes for the manufacture of galactoside inhibitors, can solve the problems of increasing the amount of unwanted azide reduction, and achieve the effect of efficient manufactur

Inactive Publication Date: 2014-01-09
GALECTO BIOTECH
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AI Technical Summary

Benefits of technology

[0061]The present invention relates to a novel synthesis method for preparation of thio-di-galactosides. One advantage of the present invention is that it provides a more efficient manufacture of thiodigalactosides compared to prior art methods.

Problems solved by technology

Hence, in situ formation of the 3-azido-galactosyl thiol from the thiouronium salt is essential in the synthesis procedure, because any other method that generate the thiol separately results in extensive unwanted azide reduction.

Method used

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Embodiment Construction

[0078]The novel route of synthesis is clearly shown in scheme 1 below, and relates in particular to the reaction of compounds of formulae (8) and (9) in the final step to form a compound of formula (10), which thiodigalactoside compound is further deprotected to form compound of formula (II) and then further reacted to form the compounds of formula (12) or (13).

[0079]In a further aspect of the invention it relates to intermediates as well, in particular the intermediates of the compounds (2) to (7) and (9) above.

[0080]The phenyl group present on the acetal carbon may be substituted with a methyl, methoxy, alkyl, alkoxy, or aryl or fused with an aryl group as well.

[0081]The phenyl group present on the S-atom, the thio group, may be substituted with a methyl, methoxy, alkyl, alkoxy, halo, nitro, or amido group as well.

[0082]In addition to acetates, the esters of compounds (2) to (10) may be aliphatic esters of 1 to 6 carbon atoms, aromatic esters, or substituted aromatic ester.

[0083]A...

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Abstract

Novel synthesis routes for preparation of thiodigalactosides and intermediates are presented. The method includes the use of a 3-azido-galactosyl thiouronium salt derivative, which is activated to the corresponding thiol in situ, which in turn is directly reacted with a 3-azido-galactosyl bromide resulting in the 3,3′-di-azido-thio-di-galactoside before the thiol has a chance to reduce the azido 10 group. Hence, in situ formation of the 3-azido-galactosyl thiol from the thiouronium salt is essential in the synthesis procedure, because any other method that generate the thiol separately results in extensive unwanted azide reduction.

Description

TECHNICAL FIELD OF THE INVENTION[0001]The present invention relates to a novel synthesis route for the manufacture of galactoside inhibitors, as well as new intermediates.BACKGROUND ART[0002]Galectins are proteins with a characteristic carbohydrate recognition domain (CRD) (Leffler et al., 2004) (FIG. 1). This is a tightly folded p-sandwich of about 130 aa (about 15 kDa) with the two defining features 1) a β-galactose binding site (C in FIG. 1) sufficient similarity in a sequence motif of about seven amino acids, most of which (about six residues) make up the β-galactose binding site. However, adjacent sites (A,B,D,E in FIG. 1) are required for tight binding of natural saccharides and different preferences of these give galectins different fine specificity for natural saccharides.[0003]The recent completion of the human, mouse and rat genome sequences reveal about 15 galectins and galectin-like proteins in one mammalian genome with slight variation between species (Leffler et al., 2...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07H19/056
CPCC07H19/056A61P29/00A61P31/00A61P35/00C07H5/10
Inventor NILSSON, ULF
Owner GALECTO BIOTECH
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