US RE50,643 E1
Benzamide compounds
Joseph Robert Pinchman, San Diego, CA (US); Peter Qinhua Huang, San Diego, CA (US); Kevin Duane Bunker, Escondido, CA (US); Rakesh Kumar Sit, San Diego, CA (US); and Ahmed Abdi Samatar, San Diego, CA (US)
Assigned to Recurium IP Holdings, LLC, San Diego, CA (US)
Appl. No. 18/212,692
Filed by Recurium IP Holdings, LLC, San Diego, CA (US)
PCT Filed Jan. 8, 2019, PCT No. PCT/US2019/012695
§ 371(c)(1), (2) Date Jun. 25, 2020,
PCT Pub. No. WO2019/139899, PCT Pub. Date Jul. 18, 2019.
Application 18/212,692 is a reissue of application No. 16/957,861, filed on Jan. 8, 2019, granted, now 11,318,134, issued on May 3, 2022.
Claims priority of provisional application 62/615,857, filed on Jan. 10, 2018.
Int. Cl. A61K 31/496 (2006.01); A61K 31/5355 (2006.01); A61K 45/06 (2006.01); C07D 205/04 (2006.01); C07D 207/12 (2006.01); C07D 211/46 (2006.01); C07D 211/58 (2006.01); C07D 241/04 (2006.01); C07D 295/112 (2006.01); C07D 295/13 (2006.01); C07D 413/12 (2006.01); C07D 471/04 (2006.01); C07D 519/00 (2006.01)
CPC A61K 31/496 (2013.01) [A61K 31/5355 (2013.01); A61K 45/06 (2013.01); C07D 205/04 (2013.01); C07D 207/12 (2013.01); C07D 211/46 (2013.01); C07D 211/58 (2013.01); C07D 241/04 (2013.01); C07D 295/112 (2013.01); C07D 295/13 (2013.01); C07D 413/12 (2013.01); C07D 471/04 (2013.01); C07D 519/00 (2013.01)] 100 Claims
 
1. A compound of Formula (I), or a pharmaceutically acceptable salt thereof, having the structure:

OG Complex Work Unit Chemistry
wherein:
R1 is selected from the group consisting of hydrogen, halogen, a substituted or unsubstituted C1-C6 alkyl, a substituted or unsubstituted C1-C6 haloalkyl, a substituted or unsubstituted C3-C6 cycloalkyl, a substituted or unsubstituted C1-C6 alkoxy, an unsubstituted mono-C1-C6 alkylamine and an unsubstituted di-C1-C6 alkylamine;
each R2 is independently selected from the group consisting of halogen, a substituted or unsubstituted C1-C6 alkyl, a substituted or unsubstituted C1-C6 haloalkyl and a substituted or unsubstituted C3-C6 cycloalkyl; or
when m is 2 or 3, each R2 is independently selected from the group consisting of halogen, a substituted or unsubstituted C1-C6 alkyl, a substituted or unsubstituted C1-C6 haloalkyl and a substituted or unsubstituted C3-C6 cycloalkyl, or two R2 groups taken together with the atom(s) to which they are attached form a substituted or unsubstituted C3-C6 cycloalkyl or a substituted or unsubstituted 3 to 6 membered heterocyclyl;
R3 is selected from the group consisting of X—R3A

OG Complex Work Unit Chemistry
R3A is a substituted or unsubstituted 5 to 10 membered heteroaryl;
R4 is selected from the group consisting of NO2, S(O)R6, SO2R6, halogen, cyano and an unsubstituted C1-C6 haloalkyl;
R5 is selected from the group consisting of —X1-(Alk1)n-R7 and —X2(CHR8)-(Alk2)p-X3—R9;
Alk1 and Alk2 are independently selected from an unsubstituted C1-C4 alkylene and a C1-C4 alkylene substituted with 1, 2 or 3 substituents independently selected from fluoro, chloro, an unsubstituted C1-C3 alkyl and an unsubstituted C1-C3 haloalkyl;
R6 is selected from the group consisting of a substituted or unsubstituted C1-C6 alkyl, a substituted or unsubstituted C1-C6 haloalkyl and a substituted or unsubstituted C3-C6 cycloalkyl;
R7 is selected from a substituted or unsubstituted C1-C6 alkoxy, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted 3 to 10 membered heterocyclyl, hydroxy, amino, a substituted or unsubstituted mono-substituted amine group, a substituted or unsubstituted di-substituted amine group, a substituted or unsubstituted N-carbamyl, a substituted or unsubstituted C-amido and a substituted or unsubstituted N-amido;
R8 is selected from a substituted or unsubstituted 3 to 10 membered heterocyclyl(C1-C6 alkyl), a substituted or unsubstituted di-C1-C6 alkylamine(C1-C6 alkyl) and a substituted or unsubstituted mono-C1-C6 alkylamine(C1-C6 alkyl);
R9 is selected from a substituted or unsubstituted 5 to 10 membered heteroaryl and a substituted or unsubstituted C6-C10 aryl;
m is 0, 1, 2 or 3;
n and p are independently selected from 0 and 1;
X1 and X2 are —NH—; and
X and X3 are independently selected from the group consisting of —O—, —S— and —NH—.