3'-O-allyl- and 3'-O-carboxymethyl- 2'-aminosaccharide derivatives, & amides thereof with peptides, as adjuvants

摘要

Compounds of formulae I and II: wherein:

R1, R4, R5, R6 and R7

are H, acetyl, "hydrocarbyl", "lipid" and -CO-"lipid";

R2

is -OH, "hydrocarbyl", "lipid" and -CO-"lipid";

R3 and R8

are acetyl, "hydrocarbyl", "lipid" and -CO-lipid";

X

is a peptide chain consisting of one or more optionally substituted natural or unnatural amino acids, the peptide comprising normal and/or abnormal peptide links; and "hydrocarbyl" is any group comprising H and C (which optionally includes heteroatoms, cyclic structures and substitution); provided at least one "hydrocarbyl", "lipid" or -CO-"lipid" moiety is present;

may be used as an adjuvant. Such normuramylglycopeptides can be located in (proteo)-liposomes and micelles and can function a simmunomodulators, along with a desired antigen (or DNA coding for the antigen) in (e.g. DNA) vaccines. Compounds of formula are provided, wherein:

R13

is acetyl, -CO-O-CH2-CCl3 or -CO-CH[-(CH2)13-Me]2; and

R14

is -CH=CH2, -COOH, -COO-Me, -CO-X-OH, -CO-X-O-Bn or -CO-X-O-Q; and

Q

is a solid support carrier; as further defined in the specification in respect of formulae XIII and XVI;

and compounds of formulae XII, XV and XIV: X-L-Lys(Dde)-O-Q```XIV where R15 is -X-OH or -X-O-Q.