IP Library › Granted Patent US 6,974,801
Granted Patent B2
US 6,974,801 · App. 10/435,925 · Granted Dec 13, 2005

Inhibitors and methods of use thereof

Assignee: The Trustees of Dartmounth College
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Quick Facts
Patent No.
US 6,974,801
App. No.
10/435,925
Granted
Dec 13, 2005
Kind
B2
Abstract

New triterpenoid derivatives with various substituents at the C-17 position of 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid (CDDO) were synthesized. Among them, 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-onitrile (CNDDO), 1-(2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl) imidazole, 1-(2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl)-2-methylimidazole, 1-(2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl)-4-methylimidazole show extremely high inhibitory activity (IC 50 =0.01-1 pM level) against production of nitric oxide induced by interferon-γ in mouse macrophages. These compounds can be used in the prevention or treatment of diseases such as cancer, Alzheimer's disease, Parkinson's disease, multiple sclerosis, rheumatoid arthritis, and other inflammatory diseases. All the new triterpenoid derivatives are more potent than previously known CDDO.

Claims (19)

1. A composition of matter having the formula:

 wherein, R is a substituted or unsubstituted carbonyl imidazole, CN, CO— D —Glu(OAc) 4 , CONH 2 , CONHNH 2 ,

2. The composition of claim 1 , wherein R is a substituted or unsubstituted carbonyl imidazole.

3. The composition of claim 1 , wherein R is CN.

4. The composition of claim 1 , wherein R is CO— D —Glu(OAc) 4 .

5. The composition of claim 1 , wherein R is CONH 2 .

6. The composition of claim 1 , wherein R is CONHNH 2 or a pharmaceutically acceptable salt thereof.

7. The composition of claim 1 , wherein said composition has the formula:

8. The composition of claim 1 , wherein said composition has the formula:

9. The composition of claim 1 , wherein said composition has the formula:

10. The composition of claim 1 , wherein said composition has the formula:

11. The composition of claim 1 , wherein said composition has the formula:

12. The composition of claim 1 , wherein said composition has the formula:

13. The composition of claim 1 , wherein said composition has the formula:

14. The composition of claim 1 , wherein said composition has the formula:

15. The composition of claim 1 , wherein said composition has the formula:

16. The composition of claim 1 , wherein said composition has the formula:

17. The composition of claim 1 , wherein said composition has the formula:

18. The composition of claim 1 , wherein said composition has the formula:

Assignments (5)
RELEASE OF SECURITY INTEREST Recorded Apr 9, 2025
From: BIOPHARMA CREDIT PLC
To: REATA PHARMACEUTICALS HOLDINGS, LLC; REATA PHARMACEUTICALS GLOBAL, INC.; REATA PHARMACEUTICALS, INC.
Reel/Frame 070793/0130 →
RELEASE OF SECURITY INTEREST Recorded Apr 9, 2025
From: BIOPHARMA CREDIT PLC
To: REATA PHARMACEUTICALS HOLDINGS, LLC; REATA PHARMACEUTICALS GLOBAL, INC.; REATA PHARMACEUTICALS, INC.
Reel/Frame 070793/0228 →
AMENDED AND RESTATED PATENT SECURITY AGREEMENT Recorded Jul 12, 2023
From: REATA PHARMACEUTICALS HOLDINGS, LLC; REATA PHARMACEUTICALS GLOBAL, INC.; REATA PHARMACEUTICALS, INC.
To: BIOPHARMA CREDIT PLC
Reel/Frame 064264/0557 →
PATENT SECURITY AGREEMENT Recorded May 18, 2023
From: REATA PHARMACEUTICALS HOLDINGS, LLC; REATA PHARMACEUTICALS GLOBAL, INC.; REATA PHARMACEUTICALS, INC.
To: BIOPHARMA CREDIT PLC
Reel/Frame 063697/0461 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 2, 2003
From: HONDA, TADASHI; HONDA, YUKIKO; GRIBBLE, GORDON W.; SPORN, MICHAEL B.; SUH, NANJOO
To: TRUSTEES OF DARTMOUTH COLLEGE, THE
Reel/Frame 014436/0612 →
Continuity (2)
Provisional Application 6037800900 · May 13, 2002
Related Publication 20040002463A1 · Jan 1, 2004