US 11,993,574 B2
Pyrazole and imidazole compounds for inhibition of IL-17 and RORgamma
Xin Jiang, Irving, TX (US); Melean Visnick, Irving, TX (US); Christopher F. Bender, Irving, TX (US); Gary Bolton, Irving, TX (US); Bradley Caprathe, Irving, TX (US); Chitase Lee, Irving, TX (US); Brian Kornberg, Irving, TX (US); Patrick O'Brien, Irving, TX (US); and Martha R. Hotema, Irving, TX (US)
Assigned to REATA PHARMACEUTICALS, INC, Irving, TX (US)
Appl. No. 17/251,295
Filed by REATA PHARMACEUTICALS, INC., Irving, TX (US)
PCT Filed Jun. 17, 2019, PCT No. PCT/US2019/037543
§ 371(c)(1), (2) Date Dec. 11, 2020,
PCT Pub. No. WO2019/241796, PCT Pub. Date Dec. 19, 2019.
Claims priority of provisional application 62/687,602, filed on Jun. 20, 2018.
Claims priority of provisional application 62/685,742, filed on Jun. 15, 2018.
Prior Publication US 2021/0292281 A1, Sep. 23, 2021
Int. Cl. C07D 231/54 (2006.01); C07D 235/02 (2006.01); C07D 401/04 (2006.01); C07D 401/06 (2006.01); C07D 401/10 (2006.01); C07D 401/14 (2006.01); C07D 403/04 (2006.01); C07D 403/10 (2006.01); C07D 403/14 (2006.01); C07D 405/04 (2006.01); C07D 409/04 (2006.01); C07D 413/10 (2006.01); C07D 413/14 (2006.01); C07D 417/04 (2006.01); C07D 417/14 (2006.01)
CPC C07D 231/54 (2013.01) [C07D 235/02 (2013.01); C07D 401/04 (2013.01); C07D 401/06 (2013.01); C07D 401/10 (2013.01); C07D 401/14 (2013.01); C07D 403/04 (2013.01); C07D 403/10 (2013.01); C07D 403/14 (2013.01); C07D 405/04 (2013.01); C07D 409/04 (2013.01); C07D 413/10 (2013.01); C07D 413/14 (2013.01); C07D 417/04 (2013.01); C07D 417/14 (2013.01)] 37 Claims
 
1. A compound of the formula:

OG Complex Work Unit Chemistry
wherein:
n is 0, 1, or 2;
R1 is cyano, fluoro, —CF3, or —C(O)Ra, wherein:
Ra is hydroxy or amino; or
alkoxy(C≤6), alkylamino(C≤6), dialkylamino(C≤6), or a substituted version of any of these groups;
R2 is hydrogen; or
alkyl(C≤12), cycloalkyl(C≤12), alkenyl(C≤12), alkynyl(C≤12), aryl(C≤18), aralkyl(C≤18), heteroaryl(C≤18), heteroaralkyl(C≤18), or a substituted version of any of these groups;
R2′ is hydrogen;
R3 is alkyl(C≤12), alkenyl(C≤12), aryl(C≤12), aralkyl(C≤12), or a substituted version of any of these groups;
R4 and R5 are each independently absent; or
cycloalkyl(C≤12), heterocycloalkyl(C≤12), aryl(C≤12), aralkyl(C≤12), heteroaryl(C≤12), heteroaralkyl(C≤12), -arenediyl(C≤12)-alkyl(C≤12), -arenediyl(C≤12)-aryl(C≤12), -arenediyl(C≤12)-heteroaryl(C≤12), -arenediyl(C≤12)-heterocycloalkyl(C≤12), -arenediyl(C≤12)-cyclo-alkyl(C≤12), -heteroarenediyl(C≤12)-alkyl(C≤12), -heteroarenediyl(C≤12)-aryl(C≤12), -hetero-arenediyl(C≤12)-heteroaryl(C≤12), -heteroarenediyl(C≤12)-hetero-cycloalkyl(C≤12), -heteroarenediyl(C≤12)-cycloalkyl(C≤12), -heterocycloalkanediyl(C≤12)-aryl(C≤12), -heterocycloalkanediyl(C≤12)-heteroaryl(C≤12), or a substituted version of any of these groups; or
a group of the formula:

OG Complex Work Unit Chemistry
wherein 1 and m are each 0, 1, 2, or 3;
R6 is absent or amino; or
alkylamino(C≤12), dialkylamino(C≤12), cycloalkylamino(C≤12), dicycloalkylamino(C≤12), alkyl(cycloalkyl)amino(C≤12), arylamino(C≤12), diarylamino(C≤12), alkyl(C≤12), cycloalkyl(C≤12), -alkanediyl(C≤12)-cycloalkyl(C≤12), -alkanediyl(C≤18)-aralkoxy(C≤18), heterocycloalkyl(C≤12), aryl(C≤18), -arenediyl(C≤12)-alkyl(C≤12), aralkyl(C≤18), -arenediyl(C≤18)-heterocycloalkyl(C≤12), heteroaryl(C≤18), -heteroarenediyl(C≤12)-alkyl(C≤12), heteroaralkyl(C≤18), acyl(C≤12), alkoxy(C≤12), or a substituted version of any of these groups;
or a pharmaceutically acceptable salt thereof.