Lipid conjugated cyclic carbonate derivatives, their synthesis, and uses
AssigneesSiolab Ltd., Yissum Research Development Company of the Hebrew University of Jerusalem
InventorsAaron Garzon, Jean Hildesheim
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Abstract
The present disclosure provides processes for the preparation of lipid conjugated cyclic carbonate derivatives. More specifically, the present disclosure is based on the finding that reacting lipids, such as, ceramides, with N,N′-disuccinimidyl derivative, resulted in the formation of, isolatable, substituted cyclic [1,3]-dioxan-2-one and [1,3]-dioxan-2-thione compounds. These isolatable cyclic substituted compounds and derivatives thereof may be used for various applications, such as in vaccination.
Claims16
A cyclic compound of general formula (I):
- wherein
- W represents O, S, NH, or CH2;
- X1, X2, X3, and X4 represent independently O or S;
- and
- R1 and R2 independently represent a C1-C24 aliphatic moiety selected from the group consisting of alkyl, alkenyl and alkynyl, and at least one of R1 and R2 is an alkenyl chain.
The cyclic compound (4R, 5S)-5-(hexadecanoylamido)-4-[(1E)-pentadecene]-[1,3]-dioxanone-2-one having formula (I):
A process for preparation of a compound of general formula (I):
- wherein
- W represents O, S, NH, or CH2;
- X1, X2, X3, and X4 represent independently O or S;
- and
- R1 and R2 independently represent a C1-C24 aliphatic moiety selected from the group consisting of alkyl, alkenyl and alkynyl, and at least one of R1 and R2 is an alkenyl chain;
- the process comprising:
- (a) providing a lipid of the following general formula (II):
- wherein
- W represents O, S, NH, or CH2;
- X1, X2, X3 and X4 represent independently O or S;
- and
- R1 and R2 independently represent a C1-C24 aliphatic moiety selected from the group consisting of alkyl, alkenyl and alkynyl, and at least one of R1 and R2 is an alkenyl chain
- (b) allowing the lipid to react in a presence of a basic catalyst with a N,N′-disuccinimidyl derivative of general formula (III)
- wherein X1′, X2′, and X3 represent independently O or S;
- to obtain a substituted [1,3]-dioxan-2-one or a [1,3]-dioxan-2-thione (I).
Dependencies are inferred from the claim text.