Methods of preparing reduced nicotinamide riboside and derivatives thereof
AssigneeChromaDex Inc.
InventorsMarie Migaud, Philip Redpath, Kerri Crossey, Mark Doherty
Life of this patent
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Abstract
Methods of preparing nicotinamide riboside and derivatives thereof, are described. In an aspect, the invention relates to a method of making a compound of formula (II), or a salt, or solvate thereof: wherein n is 0 or 1; Y is O or S; m is 1; R1 is selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted primary or secondary amino, and substituted or unsubstituted azido; and R2-R5 are each H.
Claims46
A method of making a compound of formula (IIA), or a salt, or solvate thereof:
- the method comprising the steps of:
- (a) providing a compound of formula (IVA):
- wherein n is 0 or 1;
- Y is O or S;
- m is 1;
- R1 is selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted primary or secondary amino, and azido;
- R2-R5 are each H;
- X− is an anion, wherein the anion is selected from the group consisting of a substituted or unsubstituted carboxylic acid, a halide, a substituted or unsubstituted sulfonate, a substituted or unsubstituted phosphate, a substituted or unsubstituted sulfate, a substituted or unsubstituted carbonate, and a substituted or unsubstituted carbamate;
- and
- R6, R7 and R8 are each independently selected from the group consisting of an ester-type protecting group, an ether-type protecting group, and a silyl protecting group;
- (b) reducing the compound of formula (IVA) to provide a compound of formula (IIIA)
- (c) processing the compound of formula (IIIA);
- (d) optionally, isolating the compound of formula (IIIA);
- (e) optionally, deprotecting the compound of formula (IIIA) so as to produce the compound of formula (IIA);
- and
- (f) isolating the compound of formula (IIA).
A method of making a dihydronicotinoyl riboside compound of formula (IIA), or a salt, or solvate thereof:
- the method comprising the steps of:
- (a) providing a compound of formula (IA):
- wherein n is 0 or 1;
- Y is O or S;
- m is 1;
- R1 is selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted amino, and azido;
- R2-R5 are each H;
- and
- X− is an anion, wherein the anion is selected from the group consisting of a substituted or unsubstituted carboxylic acid, a halide, a substituted or unsubstituted sulfonate, a substituted or unsubstituted phosphate, a substituted or unsubstituted sulfate, a substituted or unsubstituted carbonate, and a substituted or unsubstituted carbamate;
- and
- (b) reducing the compound of formula (IA) to provide the dihydronicotinoyl riboside compound of formula (IIA), or a salt, or solvate thereof:
- (c) optionally, processing the dihydronicotinoyl riboside compound of formula (IIA) or a salt, or solvate thereof;
- and
- (d) isolating the dihydronicotinoyl riboside compound of formula (IIA) or a salt, or solvate thereof.
A compound having formula (IVA):
- wherein n is 0 and Y is absent;
- m is 0;
- R1 is selected from the group consisting of substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, and cyano;
- R2-R5 are each H;
- R6, R7 and R5, which may be the same or different, are each independently a hydroxyl protecting group;
- and
- X− is an anion, wherein the anion is selected from the group consisting of a substituted or unsubstituted carboxylic acid, a halide, a substituted or unsubstituted sulfonate, a substituted or unsubstituted phosphate, a substituted or unsubstituted sulfate, a substituted or unsubstituted carbonate, and a substituted or unsubstituted carbamate.
Dependencies are inferred from the claim text.