Lipid conjugated cyclic carbonate derivatives, their synthesis, and uses
AssigneesBioLab, Inc., NasVax Ltd., Yissum Research Development Company of the Hebrew University of Jerusalem
InventorsAaron Garzon, Jean Hildesheim
Life of this patent
Estimating the term…
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.
Claims32
A cyclic compound of the following 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 C1-C24 aliphatic moiety which may be saturated or unsaturated, branched or linear chain, the aliphatic moiety may contain a C4-C7 aliphatic ring portion which may be substituted or unsubstituted;
A process for the preparation of a compound of the following 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 C1-C24 aliphatic moiety which may be saturated or unsaturated, branched or linear chain, the aliphatic moiety may contain a C4-C7 aliphatic ring portion which may be substituted or unsubstituted;
- the process comprising:
- (a) providing a lipid of the following general formula (II):
- wherein W, X1, X2, X4, R1 and R2 are as defined above;
- (b) allowing said lipid to react in the presence of a basic catalyst with N,N′-disuccinimidyl derivative of the general formula (III)
- wherein
- X1′, X2′ and X3 is as defined above, in the presence of a basic catalyst to obtain said substituted [1,3]-dioxan-2-one or [1,3]-dioxan-2-thione (I).
(canceled)
A process for the separation between an amine conjugated lipid of formula (IVa) and an amine-conjugated lipid of formula (IVb) from a mixture thereof, the process comprises:
- a) reacting at least one functional group on at least one of the amine-conjugated lipid of formulae (IVa) and (IVb) with a modifier to obtain a reaction product comprising a modified amine-conjugated lipid (IVa′), a modified amine-conjugated lipid (IVb′) or a combination of a modified amine-conjugated lipid (IVa′) and a modified amine-conjugated lipid (IVb′);
- b) separating at least one modified amine-conjugated lipid from the reaction product to obtain a respective separated modified amine-conjugated lipid.
- c) removing from the respective separated modified amine-conjugated lipid the modifier from the modified amine-conjugated lipid to obtain a separated amine-conjugated lipid corresponding to the separated at least one modified amine-conjugated lipid.
(canceled)
(canceled)
(canceled)
(canceled)
(canceled)
An isolated amine-conjugated lipid of general formula (IVb):
- or a mixture of amine-conjugated lipids of general formulae (IVa) and (IVb)
- wherein
- W represents O, S, NH or CH2;
- X1, X2, X3 and X4 represent independently O or S;
- and
- R1 and R2 independently represent C1-C24 aliphatic moiety which may be saturated or unsaturated, branched or linear chain, the aliphatic moiety may contain a C4-C7 aliphatic ring portion which may be substituted or unsubstituted.
Dependencies are inferred from the claim text.