Substituted 2-indoline ketone derivatives as well as preparation method and uses thereof

A technology of indolinone and its derivatives, which is applied in the field of substituted 2-indolinone derivatives, can solve the problem that cancer cells cannot be completely eliminated, and achieve the effects of high yield of finished products, improved solubility, and simple process

Active Publication Date: 2008-09-03
长治市三宝生化药业有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But as the serious drug resistance that the long-term administration of Imatinib (imatinib) of similar drug causes, will inevitably make people worry about the drug resistance of sunitinib (Nature Reviews Drug Discovery 6,734-745(September 2007 )). According to clinical reports, the role of sunitinib is to destroy the growth of blood vessels in solid tumors, but not to completely eliminate cancer cells. Therefore, its effect will disappear within 4-7 days after stopping the drug, and the tumor will start to continue to grow again .Therefore, the development of a new generation of more efficient drugs is a continuous need of clinical and patients.

Method used

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  • Substituted 2-indoline ketone derivatives as well as preparation method and uses thereof
  • Substituted 2-indoline ketone derivatives as well as preparation method and uses thereof
  • Substituted 2-indoline ketone derivatives as well as preparation method and uses thereof

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Experimental program
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Embodiment Construction

[0042] One. The preparation of the compound of the present invention

[0043] Synthesis of compound 3:

[0044] Compound 1 (1.51 g, 0.01 mol) and 50 ml of hexamethyldisilamine were mixed and refluxed for 1 hour, the solvent was evaporated under reduced pressure, and the residue was dissolved in 50 ml of anhydrous acetonitrile, and compound 2 (3.18 g, 0.01 mol) and stirred evenly. Add trimethylsilyl trifluoromethanesulfonate (0.7mL, 0.03mol) at 0°C. The mixture was heated to reflux for 1 hour, cooled to room temperature, and 20 ml of saturated sodium bicarbonate solution was slowly added under cooling , after stirring, extract with dichloromethane (3 × 30mL), combine the extracts, wash once with brine, and dry over anhydrous sodium sulfate. Filter, evaporate to dryness, and the residual silica gel column chromatography (eluent: ethyl acetate-n-hexane Alkane 1:3) to obtain compound 3 as an oily liquid (3.1 g, 76%). ESIMS: m / z 410 (M+1).

[0045] Synthesis of compound 5:

[00...

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Abstract

The invention relates to a substituted 2-indolinone derivate, a preparation method and the applications thereof in antineoplastic. The substituted 2-indolinone derivate of the invention has a chemical general structure shown in the drawing, wherein X represents one of halogen and hydrogen, or nitro and alkoxyl; R1 and R2 are any one selected from hydrogen, alkyl, cycloalkyl, aryl and heteroary respectively; A represents any one of glycoside and isomer thereof, hydroxy and alkyl, and hydroxy and alkoxyl group. The substituted substituted 2-indolinone derivate of the invention generates nucleoside analogue of sunitinib by saccharification reaction or alkylation reaction of 2-indolinone, greatly increases the solubility, the antitumor activity and the virus resistance.

Description

technical field [0001] The invention relates to a substituted 2-indolinone derivative, a preparation method and its application in antitumor. technical background [0002] In 2006, the US FDA approved the marketing application of Pfizer's new anticancer drug Sutent (sunitinib) (WO2001060814), which is used for the treatment of gastrointestinal stromal tumors and advanced renal cell carcinoma. Sutent is a new type of targeted drug that can selectively target a variety of tyrosine kinase receptors. It combines two mechanisms of anti-angiogenesis, which stops blood supply to tumor cells, and anti-tumor, which directly attacks tumor cells. It represents the advent of a new round of targeted therapy, which can directly attack tumors without the toxic side effects of conventional chemotherapy. But as the serious drug resistance that the long-term administration of Imatinib (imatinib) of similar drug causes, will inevitably make people worry about the drug resistance of sunitinib ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/06C07H17/02A61K31/404A61K31/7056A61P35/00A61P31/12
CPCY02P20/55
Inventor 靳广毅
Owner 长治市三宝生化药业有限公司
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