US 11,891,391 B2
Inhibitors of kinase networks and uses thereof
Herman O. Sintim, West Lafayette, IN (US); Neetu Dayal, Uttar Pradesh (IN); and Clement Opoku-Temeng, Worcester, MA (US)
Assigned to Purdue Research Foundation, West Lafayette, IN (US)
Filed by PURDUE RESEARCH FOUNDATION, West Lafayette, IN (US)
Filed on Apr. 29, 2021, as Appl. No. 17/243,629.
Application 17/243,629 is a division of application No. 16/499,133, granted, now 11,040,973, previously published as PCT/US2018/024991, filed on Mar. 29, 2018.
Claims priority of provisional application 62/478,069, filed on Mar. 29, 2017.
Claims priority of provisional application 62/616,643, filed on Jan. 12, 2018.
Prior Publication US 2021/0371420 A1, Dec. 2, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 471/06 (2006.01); A61K 31/437 (2006.01); C07D 471/14 (2006.01); C07D 209/08 (2006.01); C07D 231/56 (2006.01); C07D 401/14 (2006.01); C07D 413/14 (2006.01); C07D 417/12 (2006.01); C07D 471/04 (2006.01); C07D 491/147 (2006.01); C07D 495/14 (2006.01); C07D 498/04 (2006.01); C07D 513/04 (2006.01); C07D 519/00 (2006.01)
CPC C07D 471/14 (2013.01) [C07D 209/08 (2013.01); C07D 231/56 (2013.01); C07D 401/14 (2013.01); C07D 413/14 (2013.01); C07D 417/12 (2013.01); C07D 471/04 (2013.01); C07D 491/147 (2013.01); C07D 495/14 (2013.01); C07D 498/04 (2013.01); C07D 513/04 (2013.01); C07D 519/00 (2013.01); C07B 2200/05 (2013.01)] 10 Claims
 
1. A compound having a formula

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein n is 3-5; the bonding between A and B and bonding between B and D can be a single bond or a double bond, but both bonds between A and B and between B and D cannot be a double bond at the same time; A, B, and D each represent, independently, C, O, N, or S, wherein at least one of A, B, and D is a heteroatom;
R1 is amino, hydroxyl, alkyl, alkenyl, alkynyl, heteroalkyl, heteroalkenyl, heteroalkynyl, heterocyclyl, cycloalkyl, cycloalkenyl, cycloheteroalkyl, cycloheteroalkenyl, acyl, aryl, heteroaryl, arylalkyl, arylalkenyl, or arylalkynyl, each of which is optionally substituted;
R4 represents two substituents, each independently selected from the group consisting of hydrogen, deuterium, halo, azido, cyano, nitro, hydroxy, amino, thio, carboxy, ester, amide, acyl, sulfoxyl, sulfonyl, phosphate, phosphoryl, alkyl, alkenyl, alkynyl, heteroalkyl, heteroalkenyl, heteroalkynyl, heterocyclyl, cycloalkyl, cycloalkenyl, cycloheteroalkyl, cycloheteroalkenyl, aryl, heteroaryl, arylalkyl, arylalkenyl, and arylalkynyl, each of which is optionally substituted;
or the two substituents are taken together with the attached carbons to form an optionally substituted cyclic or heterocyclic moiety;
depending on A, B, and D, R5 represents two or three substituents, each independently selected from the group consisting of hydrogen, deuterium, halo, azido, cyano, nitro, hydroxy, amino, thio, carboxy, ester, amide, acyl, sulfoxyl, sulfonyl, phosphate, phosphoryl, alkyl, alkenyl, alkynyl, heteroalkyl, heteroalkenyl, heteroalkynyl, heterocyclyl, cycloalkyl, cycloalkenyl, cycloheteroalkyl, cycloheteroalkenyl, aryl, heteroaryl, arylalkyl, arylalkenyl, and arylalkynyl, each of which is optionally substituted; and
depending on the value of n, R6 represents four to six substituents, each independently selected from the group consisting of hydrogen, deuterium, halo, azido, cyano, nitro, hydroxy, amino, thio, carboxy, ester, amide, acyl, sulfoxyl, sulfonyl, phosphate, phosphoryl, alkyl, alkenyl, alkynyl, heteroalkyl, heteroalkenyl, heteroalkynyl, heterocyclyl, cycloalkyl, cycloalkenyl, cycloheteroalkyl, cycloheteroalkenyl, aryl, heteroaryl, arylalkyl, arylalkenyl, and arylalkynyl, each of which is optionally substituted.