US 11,986,442 B2
Inhibition of respiratory complex III by ligands that interact with a regulatory switch
Muhammad Hagras, Davis, CA (US); and Alexei Stuchebrukhov, Davis, CA (US)
Assigned to The Regents of the University of California, Oakland, CA (US)
Filed by The Regents of the University of California, Oakland, CA (US)
Filed on Jun. 4, 2021, as Appl. No. 17/339,620.
Application 17/339,620 is a division of application No. 16/531,511, filed on Aug. 5, 2019, granted, now 11,058,645.
Application 16/531,511 is a continuation of application No. PCT/US2018/017638, filed on Feb. 9, 2018.
Claims priority of provisional application 62/457,684, filed on Feb. 10, 2017.
Prior Publication US 2021/0309617 A1, Oct. 7, 2021
Int. Cl. A61K 31/047 (2006.01); A61K 31/05 (2006.01); A61K 31/09 (2006.01); A61K 31/12 (2006.01); A61K 31/122 (2006.01); A61K 31/192 (2006.01); A61K 31/196 (2006.01); A61K 31/351 (2006.01); A61K 31/353 (2006.01); A61K 31/404 (2006.01); A61K 31/416 (2006.01); A61K 31/5513 (2006.01); A61P 35/00 (2006.01); C07C 35/42 (2006.01); C07C 43/295 (2006.01); C07C 49/577 (2006.01); C07C 205/45 (2006.01); C07C 271/58 (2006.01); C07C 317/44 (2006.01); C07D 243/24 (2006.01); C07D 309/14 (2006.01); C07D 407/04 (2006.01); C07D 493/04 (2006.01)
CPC A61K 31/047 (2013.01) [A61K 31/05 (2013.01); A61K 31/09 (2013.01); A61K 31/12 (2013.01); A61K 31/122 (2013.01); A61K 31/192 (2013.01); A61K 31/196 (2013.01); A61K 31/351 (2013.01); A61K 31/353 (2013.01); A61K 31/404 (2013.01); A61K 31/416 (2013.01); A61K 31/5513 (2013.01); A61P 35/00 (2018.01); C07C 35/42 (2013.01); C07C 43/295 (2013.01); C07C 49/577 (2013.01); C07C 205/45 (2013.01); C07C 271/58 (2013.01); C07C 317/44 (2013.01); C07D 243/24 (2013.01); C07D 309/14 (2013.01); C07D 407/04 (2013.01); C07D 493/04 (2013.01)] 16 Claims
 
1. A method of inhibiting respiratory complex III in a cell, comprising:
contacting the cell with a compound having a structure selected from the group consisting of:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein
each R1, R2, R3, R4, R5, and R6 is independently selected from the group consisting of hydrogen, C1-6 alkyl, C1-6 alkylhydroxy, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, C6-12 aryl, halogen, hydroxyl, oxide, —CN, —NH2, —NO2, and —C(O)—C1-6 alkyl, and —C(O)O−;
the subscripts m and n are each independently integers from 0 to 5;
the subscript p is an integer from 0 to 4; and
the subscripts q, u, and v are each independently integers from 0 to 2;
such that the compound binds to respiratory complex III, thereby inhibiting respiratory complex III.