Novel synthesis of galactoside inhibitors

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.

What is claimed is: 
     
         1 . A di-galactoside of the general formula (13) 
       
         
           
           
               
               
           
         
         wherein at least one pyranose ring of the di-galactoside comprises a D-galacto pyranose ring; X is a bond; R is a phenyl group or a thienyl group, wherein the phenyl group is substituted with one or more substituents selected from the group consisting of methyl, ethyl, isopropyl, tert-butyl, fluoro, chloro, bromo, and trifluoromethyl. 
       
     
     
         2 . The di-galactoside of  claim 1 , wherein R comprises the phenyl group which is substituted with one or more substituents selected from the group consisting of fluoro, chloro, and bromo. 
     
     
         3 . The di-galactoside of  claim 1 , wherein R comprises the phenyl group is substituted with fluoro. 
     
     
         4 . The di-galactoside of  claim 1 , wherein both pyranose rings of the di-galactoside comprise D-galacto pyranose rings. 
     
     
         5 . The di-galactoside of  claim 1 , wherein the di-galactoside is for use as a medicament. 
     
     
         6 . The di-galactoside of  claim 1 , wherein the di-galactoside is for use in a method for treating inflammation, septic shock, or cancer in a mammal. 
     
     
         7 . A pharmaceutical composition comprising:
 the di-galactoside of  claim 1 ; and   a pharmaceutically acceptable additive selected from the group consisting of a carrier and an excipient.   
     
     
         8 . A method for treatment of inflammation, septic shock, or cancer, the method comprising administering to a mammal a therapeutically effective amount of the di-galactoside of  claim 1 .