US 11,702,416 B2
1H-pyrrolo[2,3-c]pyridin-7(6H)-ones and pyrazolo[3,4-c]pyridin-7(6H)-ones as inhibitors of BET proteins
Andrew P. Combs, Kennett Square, PA (US); Thomas P. Maduskuie, Jr., Wilmington, DE (US); and Nikoo Falahatpisheh, Wilmington, DE (US)
Assigned to Incyte Corporation, Wilmington, DE (US); and Incyte Holdings Corporation, Wilmington, DE (US)
Filed by Incyte Corporation, Wilmington, DE (US)
Filed on Jun. 4, 2021, as Appl. No. 17/339,546.
Application 17/339,546 is a continuation of application No. 16/994,172, filed on Aug. 14, 2020, granted, now 11,059,821.
Application 16/994,172 is a continuation of application No. 16/658,445, filed on Oct. 21, 2019, granted, now 10,781,209, issued on Sep. 22, 2020.
Application 16/658,445 is a continuation of application No. 15/927,170, filed on Mar. 21, 2018, granted, now 10,472,358, issued on Nov. 12, 2019.
Application 15/927,170 is a continuation of application No. 15/354,223, filed on Nov. 17, 2016, granted, now 9,957,268, issued on May 1, 2018.
Application 15/354,223 is a continuation of application No. 14/693,424, filed on Apr. 22, 2015, granted, now 9,540,368, issued on Jan. 10, 2017.
Claims priority of provisional application 61/983,289, filed on Apr. 23, 2014.
Prior Publication US 2021/0300925 A1, Sep. 30, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 471/04 (2006.01); A61K 31/546 (2006.01)
CPC C07D 471/04 (2013.01) [A61K 31/546 (2013.01)] 19 Claims
 
1. A method of treating an autoimmune or inflammatory disease, comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound of Formula IIIa:

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein:
R1 and R2 are each independently selected from H, methyl, ethyl, propyl, cyclopropyl, cyclopentyl, pyran-4-yl, phenyl, pyridin-2-yl, 2-chloro-4-phenyl, 2-chloro-4-fluorophenyl, and 2-hydroxyethyl;
or R1 and R2 together with the carbon atom to which they are attached form cyclopropyl;
R3 is H, methyl, ethyl, or propyl, wherein said methyl is optionally substituted with cyclopropyl, pyridinyl, —C(═O)NH2, —C(═O)NHCH3, —C(═O)(4-methylpiperazin-1-yl), —C(═O)NH(4-methylpiperazin-1-yl), or —C(═O)OH;
R5 is H, 1-methyl-1H-pyrazol-4-yl, 2-furyl, CN, NO2, methoxy, —C(═O)NH2, —C(═O)NH(CH3), —C(═O)N(CH3)2, —C(═O)-(morpholin-4-yl), —C(═O)CH3, —CH2OH, —CH2OCH3, —CH2NH2, —CH2NHSO2(CH2CH3), —CH2NHC(═O)CH3, —CH(OH)CH3, —SO2CH3, —SO2CH2CH3, —SO2-(isopropyl), —SO2N(CH3)2, —SO2NH(CH3), —SO2—NH(isopropyl), or —SO2-(piperidin-1-yl); and
R7 is methyl.