94-05-3Relevant articles and documents
Efficient, Protecting Group Free Kilogram-Scale Synthesis of the JAK1 Inhibitor GDC-4379
Angelaud, Remy,Burkhard, Johannes,Gosselin, Francis,Lao, David,Marx, Andreas,Ochsenbein, Miriam,Ranjan, Rohit,Stumpf, Andreas,Xu, Di
, p. 2537 - 2550 (2021/11/24)
The development of an improved kilogram-scale synthesis of the JAK1 inhibitorGDC-4379for the treatment of asthma is described. The new process is highlighted by a step-economical construction of a 3-substituted-4-aminopyrazole employing a telescoped oximation and hydrazine condensation of a 1,3-dielectrophile to generate nitrosopyrazole and a novel copper-catalyzed NaBH4reduction of the nitroso group. The endgame process features an amidation of aminopyrazole with acid chloride under Schotten-Baumann conditions to provide access to the penultimate intermediate. A selective N-1 alkylation of the pyrazole moiety was accomplished under phase-transfer conditions, which deliveredGDC-4379with a defined particle-size distribution suitable for micronization after recrystallization and wet milling.
ANDROGEN RECEPTOR ANTAGONISTS
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Paragraph 0534-0536, (2019/08/26)
Compounds that inhibit the androgen receptor, pharmaceutical compositions comprising one or more of the compounds, as well as methods of treating cancer using such compounds are described.
Synthesis and physicochemical properties of merocyanine dyes based on dihydropyridine and fragments of cyanoacetic acid derivatives
Borisova, Irina A.,Zubarev, Andrey A.,Rodinovskaya, Lyudmila A.,Shestopalov, Anatoliy M.
, p. 73 - 86 (2017/04/14)
Merocyanine dyes of the dihydropyridine series were prepared from salts of a(y)-picolinium and cyanoacetic acid derivatives. Their spectral characteristics suggesting their structure in solution were studied. The change in the spectral properties depending on the substituents introduced into the structure of the substituents and solvents used (solvatochromism) was considered. The protonation of the dyes was studied, and its regioselectivity was established.
