US 12,227,493 B2
Methods of inhibiting kinases
Aleksandr Aliper, Moscow (RU); Vladimir Aladinskiy, Moscow (RU); and Aleksandrs Zavoronkovs, Pak Shek Kok (HK)
Assigned to INSILICO MEDICINE IP LIMITED, Hong Kong (HK)
Filed by Insilico Medicine IP Limited, Hong Kong (HK)
Filed on Jul. 6, 2023, as Appl. No. 18/348,114.
Application 18/348,114 is a continuation of application No. 16/796,879, filed on Feb. 20, 2020, granted, now 11,739,078.
Claims priority of provisional application 62/809,413, filed on Feb. 22, 2019.
Prior Publication US 2024/0092765 A1, Mar. 21, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 405/04 (2006.01); A61K 31/4164 (2006.01); A61K 31/4439 (2006.01); A61K 31/506 (2006.01); C07D 401/04 (2006.01); C07D 401/14 (2006.01); C07D 403/04 (2006.01); C07D 403/14 (2006.01); C07D 405/14 (2006.01); C07D 409/04 (2006.01); C07D 409/14 (2006.01); C07D 413/04 (2006.01); C07D 417/04 (2006.01); C07D 471/04 (2006.01); C07D 491/048 (2006.01)
CPC C07D 405/04 (2013.01) [A61K 31/4164 (2013.01); A61K 31/4439 (2013.01); A61K 31/506 (2013.01); C07D 401/04 (2013.01); C07D 401/14 (2013.01); C07D 403/04 (2013.01); C07D 403/14 (2013.01); C07D 405/14 (2013.01); C07D 409/04 (2013.01); C07D 413/04 (2013.01); C07D 417/04 (2013.01); C07D 471/04 (2013.01); C07D 491/048 (2013.01)] 16 Claims
 
1. A method of treating fibrosis, comprising administering to a subject in need thereof:
a compound having a structure of Formula A, or a salt or solvate thereof,

OG Complex Work Unit Chemistry
wherein:
ring 1 is a phenyl, pyrimidinyl, or pyridinyl;
ring 2 is a 5-membered heteroaromatic ring;
ring 3 is an imidazolyl;
ring 4 is a phenyl;
Y is a bond;
Y1 is an amide linker having the nitrogen bonded to ring 1 and the carbon bonded to ring 2;
each n is independently 0, 1, or 2;
each o is independently 0, 1, 2, 3, 4, or 5;
each R1, R6, R11, and R12 is independently F, Br, Cl, I, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, isopropyl, tert-butyl, trifluoromethyl, hydroxy, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, trifluromethyloxy, oxygen, oxide, methylthio, ethylthio, propylthio, butylthio, pentylthio, hexylthio, heptylthio, octylthio, methylalcohol, ethylalcohol, propylalcohol, butylalcohol, pentylalcohol, hexylalcohol, heptylalcohol, octylalcohol, acetyl, carboxylic acid, alkyl carboxylic acid, methyl carboxylic acid, ethyl carboxylic acid, propionyl, butyryl, acetamide, methylacetamide, ethylacetamide, propionamide, butyramide, pentanamide, hexanamide, heptanamide, octanamide, fluoromethyl, bifluoromethyl, trifluoromethyl, fluoromethoxy, bifluoromethoxy, trifluoromethoxy, methyl ester, ethyl ester, propyl ester, butyl ester, pentyl ester, hexyl ester, heptyl ester, octyl ester, methylsulfanyl, thiomethyl, ethylsulfanyl, propylsulfanyl, butylsulfanyl, pentylsulfanyl, hexylsulfanyl, heptylsulfanyl, octylsulfanyl, sulfamoyl, methylpiperazinyl, piperazinyl, hydroxyethylpiperazinyl, bis(2-hydroxyethyl) amino, or morpholino; and
RA is a cycloaliphatic ring, 5- or 6-membered hetero cycloaliphatic ring, C1-C12 straight aliphatic chain, or C1-C12 branched aliphatic chain, any of which is independently substituted or unsubstituted.