US 11,813,259 B2
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)
Filed by Recurium IP Holdings, LLC, San Diego, CA (US)
Filed on Mar. 28, 2022, as Appl. No. 17/656,726.
Application 17/656,726 is a division of application No. 16/957,861, granted, now 11,318,134, previously published as PCT/US2019/012695, filed on Jan. 8, 2019.
Claims priority of provisional application 62/615,857, filed on Jan. 10, 2018.
Prior Publication US 2022/0226314 A1, Jul. 21, 2022
Int. Cl. C07D 413/12 (2006.01); C07D 471/04 (2006.01); A61K 31/5355 (2006.01); A61K 31/496 (2006.01); A61K 45/06 (2006.01); C07D 519/00 (2006.01); C07D 241/04 (2006.01); C07D 205/04 (2006.01); C07D 207/12 (2006.01); C07D 211/46 (2006.01); C07D 211/58 (2006.01); C07D 295/112 (2006.01); C07D 295/13 (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)] 17 Claims
 
1. A method for treating a cancer or a tumor comprising administering an effective amount of a compound of Formula (I), or a pharmaceutically acceptable salt thereof, or a pharmaceutical composition comprising an effective amount of the compound, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, diluent, excipient or combination thereof, to a subject having the cancer or the tumor, wherein the cancer or the tumor is selected from a bladder cancer, a brain cancer, a breast cancer, a bone marrow cancer, a cervical cancer, a colorectal cancer, an esophageal cancer, a hepatocellular cancer, a lymphoblastic leukemia, a follicular lymphoma, a lymphoid malignancy of T-cell or B-cell origin, a melanoma, a myelogenous leukemia, a Hodgkin's lymphoma, a Non-Hodgkin's lymphoma, a head and neck cancer (including oral cancer), an ovarian cancer, a non-small cell lung cancer, a chronic lymphocytic leukemia, a myeloma, a prostate cancer, a small cell lung cancer, a spleen cancer, a polycythemia vera, a thyroid cancer, an endometrial cancer, a stomach cancer, a gallbladder cancer, a bile duct cancer, a testicular cancer, a neuroblastoma, an osteosarcoma, an Ewings's tumor and a Wilm's tumor, Formula (I) 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—.