US 11,919,838 B2
Antioxidant inflammation modulators: oleanolic acid derivatives with amino and other modifications at C-17
Eric Anderson, Southlake, TX (US); Xin Jiang, Coppell, TX (US); and Melean Visnick, Irving, TX (US)
Assigned to REATA PHARMACEUTICALS HOLDINGS, LLC, Plano, TX (US)
Filed by REATA PHARMACEUTICALS HOLDINGS, LLC, Plano, TX (US)
Filed on Jul. 9, 2021, as Appl. No. 17/305,537.
Application 17/305,537 is a continuation of application No. 16/786,429, filed on Feb. 10, 2020, granted, now 11,091,430, issued on Aug. 17, 2021.
Application 16/786,429 is a continuation of application No. 16/115,028, filed on Aug. 28, 2018, granted, now 10,556,858, issued on Feb. 11, 2020.
Application 16/115,028 is a continuation of application No. 15/615,393, filed on Jun. 6, 2017, granted, now 10,093,614, issued on Oct. 9, 2018.
Application 15/615,393 is a continuation of application No. 14/753,297, filed on Jun. 29, 2015, granted, now 9,670,147, issued on Jun. 6, 2017.
Application 14/753,297 is a continuation of application No. 13/861,208, filed on Apr. 11, 2013, granted, now 9,102,681, issued on Aug. 11, 2015.
Application 13/861,208 is a continuation of application No. 13/356,455, filed on Jan. 23, 2012, granted, now 8,440,854, issued on May 14, 2013.
Application 13/356,455 is a continuation of application No. 12/426,778, filed on Apr. 20, 2009, granted, now 8,124,799, issued on Feb. 28, 2012.
Claims priority of provisional application 61/111,269, filed on Nov. 4, 2008.
Claims priority of provisional application 61/046,342, filed on Apr. 18, 2008.
Prior Publication US 2022/0024862 A1, Jan. 27, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07C 255/47 (2006.01); C07C 271/24 (2006.01); C07C 275/26 (2006.01); C07C 275/34 (2006.01); C07C 311/07 (2006.01); C07C 311/09 (2006.01); C07C 311/10 (2006.01); C07D 209/56 (2006.01); C07D 211/44 (2006.01); C07D 231/12 (2006.01); C07D 261/08 (2006.01); C07D 261/20 (2006.01); C07D 295/195 (2006.01); C07D 295/215 (2006.01); C07D 307/20 (2006.01); C07D 333/34 (2006.01); C07D 487/08 (2006.01); C07J 63/00 (2006.01)
CPC C07C 255/47 (2013.01) [C07C 271/24 (2013.01); C07C 275/26 (2013.01); C07C 275/34 (2013.01); C07C 311/07 (2013.01); C07C 311/09 (2013.01); C07C 311/10 (2013.01); C07D 209/56 (2013.01); C07D 211/44 (2013.01); C07D 231/12 (2013.01); C07D 261/08 (2013.01); C07D 261/20 (2013.01); C07D 295/195 (2013.01); C07D 295/215 (2013.01); C07D 307/20 (2013.01); C07D 333/34 (2013.01); C07D 487/08 (2013.01); C07J 63/008 (2013.01); C07C 2603/52 (2017.05)] 16 Claims
 
1. A method of activating the antioxidant/anti-inflammatory Keap1/Nrf2/ARE pathway in a cell, the method comprising contacting the cell with an effective amount of a compound of the formula:

OG Complex Work Unit Chemistry
wherein:
R1 and R2 are independently:
hydrogen; 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), alkylsulphonyl, alkenylsulphonyl(c≤12), alkynylsulphonyl(c≤12), arylsulphonyl(c≤12), aralkylsulphonyl(c≤12), heteroarylsulphonyl(c≤12), heteroaralkyl-sulphonyl(c≤12), or a substituted version of any of these groups;
or pharmaceutically acceptable salts, tautomers, or optical isomers thereof.