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 . A mono- or disaccharide derivative, said derivative having at least one but not more than N-1 fatty acid esters groups, wherein N is the number of hydroxyl groups of the mono- or disaccharide from which the derivative is derived. 
     
     
         2 . A mono- or disaccharide derivative according to  claim 1 , further comprising at least one but no more than N-1 anionic groups, wherein the combined number of fatty acid esters and anionic group does not exceed N. 
     
     
         3 . A mono- or disaccharide derivative according to  claim 2 , having at least 2, preferably at least 3, but not more than N-1 fatty acid esters groups and at least 1 but no more than N-2, preferably no more than N-3 anionic groups. 
     
     
         4 . Mono- or disaccharide derivative according to  claim 3 , having at least 4, but no more than N-1 fatty acid esters groups and at least 1 but no more than N-3, preferably no more than N-4 anionic groups. 
     
     
         5 . A derivatised monosaccharide according to  claim 1 , having at least one anionic group and at least two fatty acid esters, wherein the total sum of anionic groups and fatty acid esters in the range of 3-5. 
     
     
         6 . A derivatised disaccharide according to  claim 1 , having at least one anionic group, preferably one or four anionic groups, and at least one fatty acid ester, wherein the total sum of anionic groups and fatty acid esters is in the range of 6-9, preferably 7 or 8. 
     
     
         7 . A monosaccharide derivative according to  claim 1 , derived from a pentose with the general formula C 5 H 10 O 5  or a hexose with the general formula C 6 H 12 O 6 . 
     
     
         8 . A monosaccharide derivative according to  claim 1 , wherein the monosaccharide derivative is derived from a monosaccharide with N being 3 or 4. 
     
     
         9 . A disaccharide derivative according to  claim 1 , derived from a disaccharide with the general formula C 12 H 22 O 10 . 
     
     
         10 . A mono- or disaccharide derivative according to  claim 1  derived from allolose, altriose, fructose, galactose, glucose, gulose, inositol, mannose, sorbose, saccharose, maltose, lactose, lactulose, arabinose, xylose, ribose, cellobiose, gentiobiose, sucrose, turanose, melibiose. 
     
     
         11 . A mono- or disaccharide derivative according to  claim 2 , 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. 
     
     
         12 . A mono- or disaccharide derivative according to  claim 14 , wherein any R is independently selected from the group consisting of H + , K + Na + , Li +  and NH 4   + . 
     
     
         13 . A mono- or disaccharide derivative according to  claim 1 , wherein each of the fatty acid ester groups are represented by a general formula of —O—C(═O)—(CH 2 ) x —CH 3 , wherein x is at least 4, by —OC(═O)—(CH 2 ) x —CH═CH—(CH 2 ) y —CH 3 , wherein x+y is at least 4 and preferably not more than 24, 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. 
     
     
         14 . A mono- or disaccharide derivative according to  claim 13 , wherein each of the fatty acid ester groups is represented by a general formula of —OC(═O)—(CH 2 ) x —CH 3 , wherein x is between 6 and 14. 
     
     
         15 . A mono- or disaccharide derivative according to  claim 13 , wherein each fatty acid ester group is represented by a general formula of —OC(═O)—(CH 2 ) x —CH 3  wherein x is 6 or 8 or 10 or 12. 
     
     
         16 . Use of a mono- or disaccharide derivative according to  claim 1  as an adjuvant. 
     
     
         17 . Adjuvant formulation comprising a mono- or disaccharide derivative (I) according to  claim 1 , a water-immiscible liquid phase (II), an emulsifier or stabilizer (III) and optionally an aqueous phase (IV). 
     
     
         18 . Adjuvant formulation according to  claim 17 , wherein the water-immiscible phase (II) is an oil. 
     
     
         19 . Adjuvant formulation according to  claim 17 , wherein the water-immiscible phase (II) is squalane, squalene, a mineral oil, a plant oil, hexadecane, a fluorocarbon or a silicon oil. 
     
     
         20 . Adjuvant formulation according to  claim 17 , wherein the emulsifier or stabilizer (III) is a non-ionic detergent with a hydrophilic-lipophilic balance value of more than 10, a sugar fatty acid ester, or an anionic detergent with a hydrophilic-lipophilic balance value of more than 10. 
     
     
         21 - 30 . (canceled)