IP Library › Granted Patent US 12,661,370
Granted Patent B2
US 12,661,370 · App. 17/057,380 · Granted Jun 23, 2026

Amino acid salts of nicotinic acid ribosides as anti-aging agents

Inventors: Sebastian Mario Marcuccio (Endeavour Hills, AU); Rohan David Joyce (Noble Park, AU); Michel Wathier (Allston, MA); Roland Dolle (Boston, MA); Simon Tucker (Coogee, AU)
Assignees: Jumpstart Fertility Pty Ltd; Life Biosciences, Inc.
A61K31/7084C12N5/0609C12N2500/05C12N2501/10C12N2501/999
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Quick Facts
Patent No.
US 12,661,370
App. No.
17/057,380
Granted
Jun 23, 2026
Kind
B2
Abstract

The present invention relates to amino acid salts of nicotinic acid ribosides and compositions thereof of Formula I, useful in the treatment of disorders and diseases associated with deficiencies in NAD + : wherein M 1 , R 1 , R 2 , and R 3 are as described herein.

Claims (39)

1 . A salt selected from the group consisting of:

(S)-2-Ammonio-3-phenylpropanoate compound with 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridine-1-ium-3-carboxylate (1:1) (I-001);

(2S,3S)-2-Ammonio-3-methylpentanoate compound with 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridine-1-ium-3-carboxylate (1:1) (I-002);

(S)-2-Ammonio-3-(1H-indol-3-yl)propanoate compound with 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridine-1-ium-3-carboxylate (1:1) (I-003);

1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate-(S)-6-amino-2-ammoniohexanoate (1:1) (I-004);

1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate (S)-5-amino-2-ammonio-5-oxopentanoate (1:1) (I-005);

1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate-(S)-2-ammonio-4-methylpentanoate (1:1) (I-006);

1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate-(S)-2-ammonio-4-carboxybutanoate (1:1) (I-007);

(S)-2-ammonio-3-methylbutanoate-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate (1:1) (I-008);

(S)-2-ammonio-5-guanidinopentanoate-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate (1:1) (I-009); and

1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate-(S)-2-ammonio-3-(1H-imidazol-4-yl)propanoate (1:1) (I-010).

2 . A pharmaceutical composition comprising a salt of claim 1 , and a pharmaceutically acceptable carrier.

3 . The salt of claim 1 , that is (S)-2-Ammonio-3-phenylpropanoate compound with 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridine-1-ium-3-carboxylate (1:1) (I-001).

4 . The salt of claim 1 , that is

(2S,3S)-2-Ammonio-3-methylpentanoate compound with 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridine-1-ium-3-carboxylate (1:1) (I-002).

5 . The salt of claim 1 , that is

(S)-2-Ammonio-3-(1H-indol-3-yl)propanoate compound with 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridine-1-ium-3-carboxylate (1:1) (I-003).

6 . The salt of claim 1 , that is

1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate-(S)-6-amino-2-ammoniohexanoate (1:1) (I-004).

7 . The salt of claim 1 , that is

1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate (S)-5-amino-2-ammonio-5-oxopentanoate (1:1) (I-005).

8 . The salt of claim 1 , that is

1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate-(S)-2-ammonio-4-methylpentanoate (1:1) (I-006).

9 . The salt of claim 1 , that is

1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate-(S)-2-ammonio-4-carboxybutanoate (1:1) (I-007).

10 . The salt of claim 1 , that is

(S)-2-ammonio-3-methylbutanoate-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate (1:1) (I-008).

11 . The salt of claim 1 , that is

(S)-2-ammonio-5-guanidinopentanoate-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate (1:1) (I-009).

12 . The salt of claim 1 , that is

1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate-(S)-2-ammonio-3-(1H-imidazol-4-yl)propanoate (1:1) (I-010).

13 . A cell culture medium for in vitro fertilization comprising:

a compound of claim 1 ; and

culturing agents.

14 . The cell culture medium of claim 13 , wherein the culturing agent is an inorganic salt, an energy substrate, an amino acid, a chelator, a pH indicator, an antibiotic, a serum, a vitamin, a growth factor, or any combination thereof.

15 . A method of treating an age-related infertility comprising administering to a subject in need thereof an effective amount of a salt of claim 1 .

16 . A method of treating infertility comprising administering to a subject in need thereof an effective amount of a salt of claim 1 .

17 . A method of improving oocyte or blastocyst quality and maturation comprising contacting the oocyte or blastocyst with an effective amount of a salt of claim 1 prior to implantation into a subject in need of treatment of age-related infertility.

18 . The method of claim 17 , wherein the oocyte or blastocyst is cultured in an IVF media containing the salt.