886230-75-7Relevant academic research and scientific papers
Axitinib intermediate synthesis method
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, (2019/07/04)
The invention relates to an axitinib intermediate synthesis method, and belongs to the field of chemical synthesis, wherein a target compound is obtained through a Vilsmeier reaction, pyranyl protection, a wittig reaction, a reduction reaction and an iodo reaction. According to the present invention, the palladium catalytic reaction is replaced with the wittig reaction, such that the use of the expensive palladium catalyst can be avoided, the post-treatment can be conveniently performed, and the production cost is saved.
Bromide-assisted chemoselective Heck reaction of 3-bromoindazoles under high-speed ball-milling conditions: Synthesis of axitinib
Yu, Jingbo,Hong, Zikun,Yang, Xinjie,Jiang, Yu,Jiang, Zhijiang,Su, Weike
supporting information, p. 786 - 795 (2018/04/16)
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
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Paragraph 0064; 0065; 0066; 0067, (2016/10/07)
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.
Effective Laboratory-Scale Preparation of Axitinib by Two CuI-Catalyzed Coupling Reactions
Zhai, Li-Hai,Guo, Li-Hong,Luo, Yang-Hui,Ling, Yang,Sun, Bai-Wang
, p. 849 - 857 (2015/07/27)
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.
VEGFR INHIBITORS CONTAINING A ZINC BINDING MOIETY
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Page/Page column 52, (2009/04/25)
The present invention relates to VEGFR inhibitors and their use in the treatment of cell proliferative diseases such as cancer. The said derivatives may further act as HDAC inhibitors.
METHODS FOR PREPARING INDAZOLE COMPOUNDS
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Page/Page column 22, (2008/06/13)
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 FOR PREPARING INDAZOLE COMPOUNDS
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Page/Page column 31, (2010/11/30)
The invention relates to methods for preparing compounds of 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.
