885126-35-2

Usage

Uses

Used in Pharmaceutical Industry:
N-Methyl-2-[[3-[(1E)-2-(2-pyridinyl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl]thio]benzamide is used as an intermediate in the synthesis of Axitinib (A794650), a targeted therapy drug for the treatment of various types of cancer, including renal cell carcinoma and hepatocellular carcinoma. N-Methyl-2-[[3-[(1E)-2-(2-pyridinyl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl]thio]benzamide plays a crucial role in the development of this drug, contributing to its anti-cancer properties and therapeutic efficacy.
Used in Chemical Research:
N-Methyl-2-[[3-[(1E)-2-(2-pyridinyl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl]thio]benzamide is also used in chemical research for the study of its unique molecular structure and potential applications in various fields. Researchers can explore its chemical properties, reactivity, and interactions with other compounds, paving the way for the development of new drugs and materials with improved properties and applications.

Upstream product

• 100-69-6 2-vinylpyridine 
• 885126-36-3 N-1 THP-protected 2-(3-iodo-1H-indazol-6-ylsulfanyl)-N-methyl-benzamide 
• 886230-75-7 (Ε)-6-nitro-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole 
• 886230-76-8 (Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole 
• 7597-18-4 6-nitroindazole 
• 119-80-2 2,2'-dithiobenzoic acid 
• 19602-82-5 2,2'-dithiodibenzoic acid dichloride 
• 2527-58-4 2,2'-dithiobis(N-methylbenzamide) 
• 70315-70-7 3-iodo-6-nitro-1H-indazole 
• 20054-45-9 N-methyl-2-sulfanylbenzamide 
• 79762-54-2 6-bromo-1H-indazole 
• 885521-84-6 3,6-dibromo-1H-indazole 
• 110-87-2 3,4-dihydro-2H-pyran 
• 319460-85-0 axitinib 

Relevant academic research and scientific papers

Prodrug compound and application thereof in treatment of cancer

The present invention provides a compound indicated by a formula (I), pharmaceutically acceptable salts or esters thereof, a pharmaceutical composition of the compound, and the use of the compound andthe pharmaceutical composition in inhibition or regulation of tyrosine kinase activity, and treatment of tyrosine kinase mediated disease symptoms or disorders including cancer.

Bromide-assisted chemoselective Heck reaction of 3-bromoindazoles under high-speed ball-milling conditions: Synthesis of axitinib

A mechanically-activated chemoselective Heck coupling for the synthesis of 3-vinylindazoles has been developed with the aid of catalytic amounts of TBAB and NaBr as both dehalogenation restrainer and grinding auxiliary. After tuning of the chemical conditions and mechanical parameters, a series of non-activated 3-bromoindazoles and a broad scope of olefins worked well to give the corresponding coupling products in good to excellent yields. A further application of this protocol was performed in a two-step mechanochemical Heck/Migita cross coupling, which provided a highly efficient route for the synthesis of axitinib.

A process for the preparation of intermediates axi for Nepal the preparation and application of axi for Nepal

The invention relates to a method for preparing an intermediate of axitinib and application of the intermediate in preparation of axitinib. The preparation method for the intermediate of axitinib 3-iodine-6-nitro-1-(teralin-2H-pyran-2-base)-1H-indazole comprises the following steps that 6-nitroindazole and 3,4-dihydro-2H-pyran react under the action of catalyst so as to protect perssad tetralin-2H-pyran-2-base at N-H site, and the key intermediate with high yield is obtained through iodination at site 3. The application of the intermediate in preparation of axitinib is as follows: Heck coupled reaction is carried out on the intermediate and 2-vinyl pyridine, then nitro reduction and diazo-reaction for iodination are sequentially carried out, finally, the axitinib is obtained after docking of 2-sulfydryl-N-methyl benzamide and deprotection. The related main initial raw materials are easy to purchase in markets, and the method has high yield and high molecule economic efficiency, is efficient and environment-friendly, and is suitable for industrial mass production.

Processes for the Preparation of Axitinib

Processes for the preparation of Axitinib in good yield (generally greater than 80%) are provided that avoid the use of a palladium-catalyzed coupling reaction.

Effective Laboratory-Scale Preparation of Axitinib by Two CuI-Catalyzed Coupling Reactions

The discovery and development of an efficient synthesis route to axinitib is reported. The first-generation route researched by Pfizer implemented two Pd-catalyzed coupling reactions as key steps. In this work, the development of Heck-type and C-S coupling reactions catalyzed by CuI is briefly described, using an economial and practical protocol. Aspects of this route, such as selecting optimal ligands, solvent, and other conditions, are discussed in detail. The scale-up experiment was carried out to provide more than 300 g of active pharmaceutical ingredients of axitinib in Form XLI with 99.9% purity in 39% yield. In short, we provide a new choice of synthesis route to axitinib, through two copper-catalyzed coupling reactions with good yield.

METHODS FOR PREPARING INDAZOLE COMPOUNDS

The invention relates to methods for preparing indalzole compounds having formula (I) or pharmaceutically acceptable salts or solvates thereof. Compounds of the formula (I) are useful as anti-angiogenesis agents and as agents for modulating and/or inhibiting the activity of protein kinases, thus providing treatments for cancer or other diseases associated with cellular proliferation mediated by protein kinases.

Methods of preparing indazole compounds

The present invention relates to methods for preparing indazole compounds of formula I, which are useful as modulators and/or inhibitors of protein kinases. The present invention also relates to intermediate compounds useful in the preparation of compounds of formula I.