On March 5, 2020, Hinklin, Ronald Jay; Allen, Shelley; Barbour, Patrick; Cook, Adam; Dahlke, Joshua; Gaudino, John; Laird, Ellen; Mcnulty, Oren T.; Zhao, Qian published a patent.Quality Control of 1-(4-Methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-ol The title of the patent was Pyrazolo[3,4-b]pyridine compounds as inhibitors of TAM and MET kinases and their preparation. And the patent contained the following:
Provided herein are compounds of the formula I and stereoisomers, tautomers and pharmaceutically acceptable salts thereof, which are inhibitors of one or more TAM kinases and/or c-Met kinase, and are useful in the treatment and prevention of diseases which can be treated with a TAM kinase inhibitor and/or a c-Met kinase inhibitor. Compounds of formula I wherein X1 is CH2 and N; R1 is H and C1-6 alkyl; R2 is H, C1-6 alkyl, C1-6 hydroxyalkyl, (un)substituted 3- to 4-membered cycloalkyl, etc.; R9 is H and halo; G is (un)substituted 5- to 6-membered oxoheterocyclyl and (un)substituted oxoquinolinyl; and stereoisomers, tautomers and pharmaceutically acceptable salts thereof, are claimed. Example compound II was prepared by N-(3-fluoro-4-((3-iodo-1-(4-methoxybenzyl)-lH-pyrazolo[3,4-b]pyridin-4-yl)oxy)phenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide with ethanolamine; the resulting N-(3-fluoro-4-((3-((2-hydroxyethyl)amino)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)oxy)phenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide underwent hydrolysis to give compound II. The invention compounds were evaluated for their TAM and MET kinase inhibitory activity (data given). The experimental process involved the reaction of 1-(4-Methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-ol(cas: 924909-16-0).Quality Control of 1-(4-Methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-ol
The Article related to pyrazolopyridine preparation tam met kinase inhibitor, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazoles and other aspects.Quality Control of 1-(4-Methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-ol
Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics