IP Library › Granted Patent US 11,878,027
Granted Patent B2
US 11,878,027 · App. 17/873,577 · Granted Jan 23, 2024

Nicotinamide mononucleotide derivatives and their uses

Inventors: Karl D. Normington (Prides Crossing, MA); David A. Sinclair (Chestnut Hill, MA); David J. Livingston (Worcester, MA); James M. McKearin (Worcester, MA); Bruce Szczepankiewicz (Worcester, MA); Jonathan N. Kremsky (Worcester, MA)
Assignee: Metro International Biotech, LLC
A61K31/706A61K31/443A61K31/661A61K31/665C07F9/06C07F9/547C07F9/6561C07F9/65586C07F9/65742C07H11/04C07H19/048A61K31/7052C07H19/04
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Quick Facts
Patent No.
US 11,878,027
App. No.
17/873,577
Granted
Jan 23, 2024
Kind
B2
Abstract

The invention relates to compositions of nicotinamide mononucleotide derivatives and their methods of use. The invention also relates to methods of preparing nicotinamide mononucleotide derivatives. The invention relates to pharmaceutical compositions and nutritional supplements containing a nicotinamide mononucleotide derivative. The invention relates to methods of using nicotinamide mononucleotide derivatives that promote the increase of intracellular levels of nicotinamide adenine dinucleotide (NAD+) in cells and tissues for treating diseases and improving cell and tissue survival.

Claims (18)

1. A method of making a compound selected from

or a salt thereof; said method comprising

(a) combining a Grignard reagent and a compound having the structure

to afford a phosphoramidate compound comprising a dihydropyridine and an acetonide group;

(b) oxidizing the dihydropyridine of the phosphoramidate compound to afford a pyridinium compound comprising an acetonide group;

(c) removing the acetonide group of the pyridinium compound to afford a compound selected from compounds I-VII.

2. The method of claim 1 , wherein the compound is

3. The method of claim 1 , wherein the compound is

4. The method of claim 1 , wherein the compound is

5. The method of claim 1 , wherein the compound is

6. The method of claim 1 , wherein the compound is

7. The method of claim 1 , wherein the compound is

8. The method of claim 1 , wherein the compound is

9. The method of claim 1 , wherein step (a) is performed in the presence of said Grignard reagent in an aprotic solvent.

10. The method of claim 9 , wherein the Grignard reagent is tBuMgCl and the aprotic solvent is THF.

11. The method of claim 1 , wherein oxidation of the dihydropyridine ring to a pyridine ring is performed with hydrogen peroxide.

12. The method of claim 1 , wherein step (c) includes removal of the acetonide group under acidic conditions.

13. The method of claim 12 , wherein removal of the acetonide group is performed with trifluoroacetic acid.

Assignments (2)
CHANGE OF NAME Recorded Sep 27, 2022
From: METROBIOTECH, LLC
To: METRO INTERNATIONAL BIOTECH, LLC
Reel/Frame 061228/0488 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 27, 2022
From: LIVINGSTON, DAVID J.; MCKEARIN, JAMES M.; SZCZEPANKIEWICZ, BRUCE; KREMSKY, JONATHAN N.; SINCLAIR, DAVID A.; NORMINGTON, KARL D.
To: METROBIOTECH, LLC
Reel/Frame 061552/0666 →
Continuity (6)
Continuation 16713711 · Dec 13, 2019
Continuation 15877597 · Jan 23, 2018
Continuation 15463683 · Mar 20, 2017
Division 15512388
Provisional Application 62201447 · Aug 5, 2015
Related Publication 20230158053A1 · May 25, 2023
Cited By (3)
US 12,391,721 US 12,485,135 US 12,616,713