IP Library Granted Patent US 9,233,998
Granted Patent B2
US 9,233,998 · App. 13/552,530 · Granted Jan 12, 2016

Natural product analogs including an anti-inflammatory cyanoenone pharmacore and methods of use

Inventors: Eric Anderson (Houston, TX); Gary L. Bolton (Ann Arbor, MI); Deborah A. Ferguson (Branchburg, NJ); Xin Jiang (Dallas, TX); Robert M. Kral, Jr. (Grapevine, TX); Patrick M. O'Brien (Stockbridge, MI); Melean Visnick (Irving, TX)
Assignee: REATA PHARMACEUTICALS, INC.
C07J41/0094C07C255/46C07D311/74C07D317/26C07D493/10C07F7/1856C07J21/003C07J41/0055C07J53/001C07J71/0005C07C2101/16
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Quick Facts
Patent No.
US 9,233,998
App. No.
13/552,530
Granted
Jan 12, 2016
Kind
B2
Abstract

This invention provides novel compounds comprising the following anti-inflammatory pharmacore: wherein X, R 1 and R 2 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.

Claims (10)

1. A compound of the formula:

wherein:

R 3 and R 4 are each independently:

hydrogen, hydroxy, halo, amino, hydroxyamino, nitro, cyano, azido, or mercapto; or

alkyl (C≦12) , alkenyl (C≦12) , alkynyl (C≦12) , aryl (C≦12) , aralkyl (C≦12) , heteroaryl (C≦12) , heteroaralkyl (C≦12) , acyl (C≦12) , alkoxy (C≦12) , alkenyloxy (C≦12) , alkynyloxy (C≦12) , aryloxy (C≦12) , aralkoxy (C≦12) , heteroaryloxy (C≦12) , heteroaralkoxy (C≦12) , acyloxy (C≦12) , alkylamino (C≦12) , dialkylamino (C≦12) , alkoxyamino (C≦12) , alkenylamino (C≦12) , alkynylamino (C≦12) , arylamino (C≦12) , aralkylamino (C≦12) , heteroarylamino (C≦12) , heteroaralkylamino (C≦12) , amido (C≦12) , alkylsulfonylamino (C≦12) , alkylsilyl (C≦12) , alkylsilyloxy (C≦12) , or a substituted version of any of these groups;

or a pharmaceutically acceptable salt, tautomer, acetal, or ketal, thereof.

2. The compound of claim 1 , further defined by the formula:

or a pharmaceutically acceptable salt, ketal, or tautomer thereof.

3. The compound of claim 1 , further selected from the group consisting of:

or a pharmaceutically acceptable salt, ketal, or tautomer thereof.

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; FERGUSON, DEBORAH A.; JIANG, XIN; KRAL, ROBERT M., JR.; VISNICK, MELEAN
To: REATA PHARMACEUTICALS, INC.
Reel/Frame 036788/0975 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 14, 2015
From: AAPHARMASYN
To: REATA PHARMACEUTICALS, INC.
Reel/Frame 036789/0318 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 14, 2015
From: BOLTON, GARY L.; O'BRIEN, PATRICK M.
To: AAPHARMASYN
Reel/Frame 036789/0215 →
Continuity (3)
Continuation 12426889 · Apr 20, 2009
Provisional Application 61046363 · Apr 18, 2008
Related Publication 20120283450A1 · Nov 8, 2012