IP Library Granted Patent US 9,884,809
Granted Patent B2
US 9,884,809 · App. 14/877,974 · Granted Feb 6, 2018

Pyrazolyl and pyrimidinyl tricyclic enones as antioxidant inflammation modulators

Inventors: Eric Anderson (Southlake, TX); Gary L. Bolton (Ann Arbor, MI); Bradley Caprathe (Livonia, MI); Xin Jiang (Coppell, TX); Chitase Lee (Ann Arbor, MI); William H. Roark (Ann Arbor, MI); Melean Visnick (Irving, TX)
Assignee: REATA PHARMACEUTICALS, INC.
C07C255/47C07D231/54C07D239/70C07D401/04C07D403/04C07D413/04C07D417/04C07D487/04
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,884,809
App. No.
14/877,974
Granted
Feb 6, 2018
Kind
B2
Abstract

Disclosed herein are novel antioxidant inflammation modulators, including those of the formula: wherein the variables are defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such compounds. Methods and intermediates useful for making the compounds, and methods of using the compounds and compositions thereof are also provided.

Claims (17)

1. A compound of the formula:

wherein:

R 1 and R 2 are each methyl; and

R 3 ,R 4 ,R 5 and R 6 are each independently:

hydrogen, hydroxy or amino, or

alkyl (c≦12) , acyl (c≦12) , alkoxy (c≦12) , aryloxy (c≦12) , alkylamino (c≦12) , dialkylamino (c≦12) , amido (c≦12) , or a substituted version of any of these groups;

or a pharmaceutically acceptable salt or tautomer thereof.

2. The compound of claim 1 , wherein R 4 ,R 5 and R 6 are each hydrogen.

3. The compound of claim 1 , wherein R 3 is hydroxy.

4. The compound of claim 1 , wherein R 3 is alkoxy (c≦6) or substituted alkoxy (c≦6) .

5. The compound of claim 4 , wherein R 3 is substituted alkoxy (c≦6) .

6. The compound of claim 5 , wherein R 3 is methoxymethoxy.

7. The compound of claim 1 , wherein carbon atom 10 is in the R configuration.

8. The compound of claim 1 , wherein carbon atom 10 is in the S configuration.

9. The compound of claim 1 , wherein carbon atom 5 is in the R configuration.

10. The compound of claim 1 , wherein carbon atom 5 is in the S configuration.

11. The compound of claim 1 , further defined as:

Assignments (9)
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 →
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 →
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 →
RELEASE OF SECURITY INTEREST Recorded Jun 24, 2020
From: OXFORD FINANCE LLC, AS COLLATERAL AGENT
To: REATA PHARMACEUTICALS, INC.
Reel/Frame 053034/0018 →
SECURITY INTEREST Recorded Jun 14, 2018
From: REATA PHARMACEUTICALS, INC.
To: OXFORD FINANCE LLC, AS COLLATERAL AGENT
Reel/Frame 046357/0605 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 14, 2015
From: ANDERSON, ERIC; JIANG, XIN; VISNICK, MELEAN
To: REATA PHARMACEUTICALS, INC.
Reel/Frame 036788/0181 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 14, 2015
From: AAPHARMASYN LLC
To: REATA PHARMACEUTICALS, INC.
Reel/Frame 036788/0411 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 14, 2015
From: BOLTON, GARY L.; CAPRATHE, BRADLEY; LEE, CHITASE; ROARK, WILLIAM H.
To: AAPHARMASYN L.L.C
Reel/Frame 036788/0325 →
Continuity (4)
Continuation 13939818 · Jul 11, 2013
Continuation 13330378 · Dec 19, 2011
Provisional Application 61424601 · Dec 17, 2010
Related Publication 20160130220A1 · May 12, 2016