Use of modified oligo-b-(1,3)-glucanes for treating diseases of the immune system oligo-b-(1,3v-glucane-(1,3)-mannose, oligo-b-(1,3)-glucane-(1,3)-mannitol and derivatives thereof, methods for preparing the same and drugs containing them

Abstract

The present invention relates to the use of at least one compound of formula (III), (IV), (V) or (VI), in which p is an integer from 0 to 9; and R2 represents hydrogen, allyl, methylnaphthyl, benzyl, paramethoxybenzyl, or halogenoacetyl, for the preparation of a medicament for treating diseases such as tumors, cancer, viral disease, bacterial disease, fungal disease, disease of the immune system, auto-immune disease or disease linked to a deficiency in immunostimulation, in human beings and warm-blooded animals. The invention also relates to new products having a mannose or mannitol termination as well as a method for preparing them.

What is claimed is: 
     
         1 . A compound selected from the group consisting of formulae (III), (IV), (V) and (VI) below: 
       
         
           
           
               
               
           
         
         wherein: 
         p is an integer from 0 to 9; 
         R2 represents hydrogen, allyl, methylnaphthyl, benzyl, paramethoxybenzyl, or halogenoacetyl; 
         R3 and R4, on the one hand, and R′3 and R′4, on the other hand, together form an ethylidyl, isopropylidyl, hexafluoroisopropylidyl, cyclopentylidyl, cyclohexylidyl, cycloheptylidyl, butylidyl, 1-tertiobutylethylidyl, benzylidyl, methoxybenzylidyl, or 1-phenylbenzylidyl radical, or R3, R4, R3′ and R4′ represent each independently of each other a benzyl, chlorobenzyl, nitrobenzyl, allyl, triarylmethyl, or trialkylsilyl, ester; 
         R5 represents H, a levulinoyl, acetyl, chloroacetyl, fluorenylmethyloxycarbonyl, or trialkylsilyl group, 
         provided that none of R3, R4, R3′, R4′ is identical to R5; 
         R7 represents an ester; 
         R8, a group orthogonal to all the other protective groups, which can be selected from the group consisting of Bn, NAP, p-methoxybenzyl, p-methoxyphenyl, and allyl, and 
         R9 represents OR8 or X. 
       
     
     
         2 . The compound according to  claim 1 , wherein p is an integer from 0 to 6. 
     
     
         3 . The compound according to  claim 1 , wherein p is equal to 2, 3 or 4. 
     
     
         4 . The compound according to  claim 1 , wherein the halogenoacetyl group of R2 is selected from the group consisting of chloroacetyl, bromoacetyl and iodoacetyl. 
     
     
         5 . The compound according to  claim 1 , wherein the trialkylsilyl group of R3, R4, R3′, R4′ and R5 is selected from the group consisting of triethylsilyl, tri-iso-propylsilyl and tertiobutyldimethylsilyl. 
     
     
         6 . The compound according to  claim 1 , wherein the ester group of R3, R4, R3′ and R4′ is selected from the group consisting of acetyl, chloroacetyl, benzoyl, and pivaloyl. 
     
     
         7 . The compound according to  claim 1 , wherein R5 represents a levulinoyl group. 
     
     
         8 . The compound according to  claim 1 , wherein the ester group of R7 is selected from the group consisting of acetyl, benzoyl, and pivaloyl. 
     
     
         9 . The compound according to  claim 1 , wherein the ester group of R7 represents a benzoyl group. 
     
     
         10 . The compound according to  claim 1 , wherein R8 represents Bn.