US 11,884,648 B2
Histone demethylase inhibitors
Zhe Nie, San Diego, CA (US); Jeffrey Alan Stafford, San Diego, CA (US); James Marvin Veal, Apex, NC (US); and Michael Brennan Wallace, San Diego, CA (US)
Assigned to Celgene Quanticel Research, Inc., San Diego, CA (US)
Filed by CELGENE QUANTICEL RESEARCH, INC., San Diego, CA (US)
Filed on Nov. 13, 2020, as Appl. No. 17/097,193.
Application 16/168,753 is a division of application No. 15/487,362, filed on Apr. 13, 2017, granted, now 10,150,754, issued on Dec. 11, 2018.
Application 17/097,193 is a continuation of application No. 16/819,875, filed on Mar. 16, 2020, granted, now 10,870,634.
Application 16/819,875 is a continuation of application No. 16/168,753, filed on Oct. 23, 2018, granted, now 10,654,830, issued on May 19, 2020.
Claims priority of provisional application 62/324,813, filed on Apr. 19, 2016.
Prior Publication US 2021/0139460 A1, May 13, 2021
Int. Cl. C07D 401/14 (2006.01); C07D 401/04 (2006.01)
CPC C07D 401/14 (2013.01) [C07D 401/04 (2013.01)] 4 Claims
 
1. A method of inhibiting a histone demethylase enzyme selected from a group comprising FBXL10, JARID1B, JMJD2C and JMJD3 comprising contacting a histone demethylase enzyme with an effective amount of a compound of Formula II

OG Complex Work Unit Chemistry
wherein a compound of Formula II is optionally a pharmaceutically acceptable salt thereof, and wherein
R2 is halogen or —CF3;
R3 is hydrogen, halogen, —OH, —OR6, —N(R6)2, or alkyl, carbocyclyl, aryl optionally substituted with halogen, carbocyclylalkyl, or aralkyl optionally substituted with halogen or alkyl;
R4 is hydrogen, halogen, —OH, —OR6, —N(R6)2, or alkyl, carbocyclyl, aryl, carbocyclylalkyl, or aralkyl; wherein
each R6 is independently hydrogen, or optionally substituted alkyl, carbocyclyl, aryl, carbocyclylalkyl, or aralkyl; and
R5 is hydrogen, methyl, ethyl, isopropyl, t-butyl, —CHF2, —CH2F, —CF3, —CH2OH, —CHCH3OH, or —C(CH3)2OH.