IP Library Granted Patent US 11,472,764
Granted Patent B2
US 11,472,764 · App. 16/940,491 · Granted Oct 18, 2022

Therapeutic DNP derivatives and methods using same

Inventors: Gerald I. Shulman (East Haven, CT); David A. Spiegel (New Haven, CT)
Assignee: Yale University
C07C205/37A61K31/085C07J41/0055
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Quick Facts
Patent No.
US 11,472,764
App. No.
16/940,491
Granted
Oct 18, 2022
Kind
B2
Abstract

The present invention includes DNP derivatives that are useful for preventing or treating a metabolic disease or disorder in a subject in need thereof. In certain embodiments, the subject is further administered at least one additional therapeutic agent.

Claims (22)

1. A compound selected from the group consisting of:

N-(2-hydroxy-3,5-dinitrobenzyl)-4-mercaptobutanamide,

2-(1-hydroxypropyl)-4,6-dinitrophenol,

4-(2,4-dinitrophenoxy)pentan-2-ol,

3-(2,4-dinitrophenoxy) cyclohexanol,

2,4-dinitrophenyl dihydrogen phosphate,

3-((4-((2,4-dinitrophenoxy)methyl)phenyl)disulfanyl) propanoic acid,

3-((4-((((4-((2,4-dinitrophenoxy)methyl)phenyl)carbamoyl)oxy)methyl)phenyl) disulfanyl)propanoic acid, and

(R)-4-((3R,5R,7R,8R,9S,10 S,12S,13R,14S,17S)-3-(2-(3-((4-((2,4-dinitrophenoxy)methyl)phenyl)disulfanyl)propanamido)ethoxy)-7,12-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid.

2. A pharmaceutical composition comprising at least one pharmaceutically acceptable carrier and a compound selected from the group consisting of:

N-(2-hydroxy-3,5-dinitrobenzyl)-4-mercaptobutanamide,

2-(1-hydroxypropyl)-4,6-dinitrophenol,

4-(2,4-dinitrophenoxy)pentan-2-ol,

3-(2,4-dinitrophenoxy) cyclohexanol,

2,4-dinitrophenyl dihydrogen phosphate,

3-((4-((2,4-dinitrophenoxy)methyl)phenyl)disulfanyl) propanoic acid,

3-((4-((((4-((2,4-dinitrophenoxy)methyl)phenyl)carbamoyl)oxy)methyl)phenyl) disulfanyl)propanoic acid, and

(R)-4-((3R,5R,7R,8R,9S,10S,12S,13R,14S,17S)-3-(2-(3-((4-((2,4-dinitrophenoxy)methyl)phenyl)disulfanyl)propanamido)ethoxy)-7,12-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid.

3. The pharmaceutical composition of claim 2 , further comprising at least one additional therapeutic agent.

4. The pharmaceutical composition of claim 2 , wherein the compound is present in an amount of about 1 mg to about 500 mg.

5. The pharmaceutical composition of claim 2 , wherein the composition is in the form of tablets, dragees, liquids, drops, suppositories, or capsules, caplets, or gelcaps.

6. The pharmaceutical composition of claim 5 , wherein the tablet comprises a multi-layered delayed release tablet.

Assignments (1)
CONFIRMATORY LICENSE Recorded Aug 4, 2020
From: YALE UNIVERSITY
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 053389/0612 →
Continuity (4)
Continuation 16419949 · May 22, 2019
Continuation 14914408
Provisional Application 61872279 · Aug 30, 2013
Related Publication 20200354306A1 · Nov 12, 2020