US 11,780,816 B2
Aminobenzimidazole derivatives, treatments, and methods of inhibiting histone deacetylase
Tong Wang, Scottsdale, AZ (US); and Stephen Gately, Scottsdale, AZ (US)
Assigned to Translational Drug Development, LLC, Scottsdale, AZ (US)
Filed by TRANSLATIONAL DRUG DEVELOPMENT, LLC, Scottsdale, AZ (US)
Filed on Jan. 31, 2022, as Appl. No. 17/588,945.
Application 17/588,945 is a continuation of application No. 16/644,457, granted, now 11,236,052, previously published as PCT/US2018/049801, filed on Sep. 6, 2018.
Claims priority of provisional application 62/554,728, filed on Sep. 6, 2017.
Prior Publication US 2022/0153705 A1, May 19, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 235/30 (2006.01); C07D 405/06 (2006.01); A61P 35/00 (2006.01)
CPC C07D 235/30 (2013.01) [A61P 35/00 (2018.01); C07D 405/06 (2013.01)] 20 Claims
 
1. A method of treating a subject having a disease by inhibiting an HDAC isoform, comprising administering to the subject a compound of formula (I):

OG Complex Work Unit Chemistry
wherein:
X is selected from the group consisting of: H, halo, —C1-C6 alkyl, aryl, —C3-C7 cycloalkyl, and -3- to 10-membered heterocycle, any of which is unsubstituted, or substituted with one or more of: -halo, —C1-C6 alkyl, —O—(C1-C6 alkyl), —OH, —CN, —COOR′, —OC(O)R′, NHR′, N(R′)2, —NHC(O)R′, and —C(O)NHR′, wherein R′ is —H or —C1-C6 alkyl;
A is selected from the group consisting of: a bond, —C1-C6 alkyl, and —C3-C7 cycloalkyl, any of which is unsubstituted, or substituted with one or more of: -halo, —C1-C6 alkyl, —O—(C1-C6 alkyl), —OH, —CN, —COOR′, —OC(O)R′, NHR′, N(R′)2, —NHC(O)R′, and —C(O)NHR′, wherein R′ is —H or —C1-C6 alkyl;
Y is selected from the group consisting of: H, —C1-C6 alkyl, —C3-C7 cycloalkyl, aryl, and -3- to 10-membered heterocycle, any of which is unsubstituted, or substituted with one or more of: -halo, —C1-C6 alkyl, —O—(C1-C6 alkyl), —OH, —CN, —COOR′, —OC(O)R′, NHR′, N(R′)2, —NHC(O)R′, and —C(O)NHR′, wherein R′ is —H or —C1-C6 alkyl; and
Q is selected from the group consisting of: —H, -halo, —C1-C6 alkyl, —O—(C1-C6 alkyl), —OH, —CN, —COOR′, —OC(O)R′, NHR′, N(R′)2, —NHC(O)R′, and —C(O)NHR′, wherein R′ is —H or —C1-C6 alkyl;
wherein the compound inhibits the histone deacetylating activity of the HDAC isoform and the disease is a cancer selected from the group consisting of colon cancer, diffuse large B-cell lymphoma (DLBCL), hepatocellular carcinoma, Hodgkin's lymphoma, leukemia, lung cancer, neuroblastoma, non-Hodgkin's lymphoma, pancreatic ductal adenocarcinoma, peripheral T-cell lymphoma, prostate cancer, and Waldenstrom myeloma.