Mono-and disaccharide derivatives

Abstract

The present invention relates to a novel family of monosaccharide derivatives and disaccharide derivatives and to a method of preparation thereof. A mono- and disaccharide derivatives according to the invention comprises at least one fatty acid ester and may further comprise one or more anionic groups and are useful for inter alia, medical, pharmaceutical, cosmetic and food applications.

1 - 31 . (canceled)  
     
     
         32 . A method for preparing an adjuvanted formulation comprising an adjuvant and an antigenic component or a drug molecule, the method comprising complexing the adjuvant with the antigenic component or the drug molecule, wherein said adjuvant comprises a mono- or disaccharide, wherein at least one free hydroxyl group or at least one hydrogen atom of a hydroxyl group is substituted with a fatty acid group to obtain a fatty acid ester group, and wherein the number of fatty acid groups is not more than N-1, where N is the number of hydroxyl groups present on the mono- or disaccharide.  
     
     
         33 . A method according to  claim 32 , wherein the mono- or disaccharide is substituted with at least one but no more than N-1 anionic groups, and wherein the combined number of fatty acid groups and anionic groups does not exceed N.  
     
     
         34 . A method according to  claim 32 , wherein the mono- or disaccharide is substituted with at least two fatty acid groups.  
     
     
         35 . A method according to  claim 32 , wherein the mono- or disaccharide is substituted with no more than N-2 anionic groups.  
     
     
         36 . A method according to  claim 32 , wherein the mono- or disaccharide is a monosaccharide.  
     
     
         37 . A method according to  claim 36 , wherein the monosaccharide is a pentose having the general formula C 5 H 10 O 5 .  
     
     
         38 . A method according to  claim 32 , wherein the mono- or disaccharide is a disaccharide.  
     
     
         39 . A method according to  claim 38 , wherein the disaccharide is a hexose having the general formula C 6 H 12 O 6 .  
     
     
         40 . A method according to  claim 32 , wherein the mono- or disaccharide is allolose, altriose, fructose, galactose, glucose, gulose, mannose, sorbose, saccharose, maltose, lactose, lactulose, arabinose, xylose, ribose, cellobiose, gentiobiose, sucrose, turanose, melibiose.  
     
     
         41 . A method according to  claim 32 , wherein each of the fatty acid ester groups are independently represented by a general formula of —O—C(═O)—(CH 2 ) x —CH 3 , wherein x is at least 4, by a general formula of —OC(═O)—(CH 2 ) x —CH═CH—(CH 2 ) y —CH 3 , wherein x+y is at least 4, or —O—(C═O)—(CH 2 ) x —CH═CH—(CH 2 ) y —CH═CH—(CH 2 ) z —CH 3 , wherein x+y+z is between 2 and 20.  
     
     
         42 . A method according to  claim 33 , wherein at least one anionic group is a sulphate ester having the general formula —SO 2 —OR, or a phosphate ester having the general formula —PO 2 —(OR) 2 , wherein R is a monovalent cation.  
     
     
         43 . A method according to  claim 32 , wherein the adjuvanted formulation is a vaccine.  
     
     
         44 . A method for preparing a formulation comprising a water-immiscible molecule and an emulsifier, the method comprising complexing the emulsifier with the water-immiscible molecule, wherein the emulsifier comprises a mono- or disaccharide, wherein at least one free hydroxyl group or at least one hydrogen atom of a hydroxyl group is substituted with a fatty acid group to obtain a fatty acid ester group, and wherein the number of fatty acid groups is not more than N-1 fatty, where N is the number of hydroxyl groups present on the mono- or disaccharide.  
     
     
         45 . A method according to  claim 44 , wherein the mono- or disaccharide is substituted with at least one but no more than N-1 anionic groups, and wherein the combined number of fatty acid groups and anionic groups does not exceed N.  
     
     
         46 . A method according to  claim 44 , wherein the mono- or disaccharide is substituted with at least two fatty acid groups.  
     
     
         47 . A method according to  claim 44 , wherein the mono- or disaccharide is substituted with no more than N-2 anionic groups.  
     
     
         48 . A method according to  claim 44 , wherein the mono- or disaccharide is a monosaccharide.  
     
     
         49 . A method according to  claim 48 , wherein the monosaccharide is a pentose having the general formula C 5 H 10 O 5 .  
     
     
         50 . A method according to  claim 44 , wherein the mono- or disaccharide is a disaccharide.  
     
     
         51 . A method according to  claim 50 , wherein the disaccharide is a hexose having the general formula C 6 H 12 O 6 .  
     
     
         52 . A method according to  claim 44 , wherein the mono- or disaccharide is allolose, altriose, fructose, galactose, glucose, gulose, mannose, sorbose, saccharose, maltose, lactose, lactulose, arabinose, xylose, ribose, cellobiose, gentiobiose, sucrose, turanose, melibiose.  
     
     
         53 . A method according to  claim 44 , wherein each of the fatty acid ester groups are independently represented by a general formula of O—C(═O)—(CH2) x —CH 3 , wherein x is at least 4, by a general formula of —OC(═O)—(CH 2 ) x —CH═CH—(CH 2 ) y —CH 3 , wherein x+y is at least 4, or —O—(C═O)—(CH 2 ) x —CH═CH—(CH 2 ) y —CH═CH—(CH 2 ) z —CH 3 , wherein x+y+z is between 2 and 20.  
     
     
         54 . A method according to  claim 45 , wherein at least one anionic group is a sulphate ester having the general formula —SO 2 —OR, or a phosphate ester having the general formula —PO 2 —(OR) 2 , wherein R is a monovalent cation.