Immunologically active dipeptidyl saccharides and methods of preparation

Claim 1

Immunostimulatory 2-amino-2-deoxy-glycoses of the general structural formula: ##STR11## provided said glycose is not 2-amino-2-deoxy-D-glucose, wherein R 1 is hydrogen, alkyl of 1 to 7 carbon atoms optionally substituted by hydroxy, mercapto, alkoxy of 1 to 3 carbon atoms, alkyl mercapto of 1 to 3 carbon atoms, hydroxy or mercapto esterified by an acid of 1 to 4 carbon atoms, halogen, carboxyl, carboxyl esterified by an alcohol of 1 to 3 carbon atoms, or amidated carboxyl, phenyl, benzyl each optionally substituted by alkyl of 1 to 3 carbon atoms, lower alkyldioxy, amino, trifluoromethyl, hydroxy, mercapto, hydroxy or mercapto etherified by alkyl of 1 to 3 carbon atoms, or hydroxy or mercapto esterified by an acid of 1 to 4 carbon atoms; R 2 is alkyl of 1 to 7 carbon atoms optionally substituted by hydroxy, mercapto, alkoxy of 1 to 3 carbon atoms, alkyl mercapto of 1 to 3 carbon atoms, hydroxy or mercapto esterified by an acid of 1 to 4 carbon atoms, halogen, carboxyl, carboxyl esterified by an alcohol of 1 to 3 carbon atoms, or amidated carboxyl, phenyl, optionally substituted by alkyl of 1 to 3 carbon atoms, lower alkyldioxy, amino, trifluoromethyl, hydroxy, mercapto, hydroxy or mercapto etherified by alkyl of 1 to 3 carbon atoms, or hydroxy or mercapto esterified by an acid of 1 to 4 carbon atoms; R 3 is H or alkyl of 1 to 10 carbon atoms; R 4 and R 5 are same or different and are hydrogen alkanoyl of 2 to 21 carbon atoms, benzoyl, naphthoyl-1 or naphthoyl-2 each optionally substituted by halogen, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, trifluoromethyl, hydroxy or alkanoyloxy of 1 to 3 carbons, an alkanesulfonic acid of 1 to 7 carbon atoms, or a phenylsulfonic acid optionally substituted by alkyl of 1 to 3 carbon atoms, carbamoyl, alkyl carbamoyl of 1 to 3 carbon atoms, phenylcarbamoyl or napththylcarbamoyl; R 6 is H or R 6 -R 7 together is --CH 2 --CH 2 --CH 2 --; R 7 is H, alkyl of 1 to 7 carbon atoms, hydroxymethyl, mercaptomethyl, benzyl; or substituted benzyl wherein the substituents are the same as defined for R 1 ; R 8 and R 9 each is carboxyl, esterified carboxyl of 1 to 7carbon atoms, amidated carboxyl, or mono- or dialkyl amidated carboxyl wherein the alkyl group has 1 to 3 carbon atoms; provided that when R 3 is lower alkyl, the stereochemistry at asymmetric center I can be either D or L, when R 7 is not H, the stereochemistry at asymmetric center II is either L or D, and the stereochemistry at asymmetric center III is D.