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Furo[2,3-d]pyrimidine-4-amine derivatives

A furan ring and compound technology, applied in the field of furo[2,3-d]pyrimidin-4-amine derivatives, can solve problems such as increased adverse reactions

Active Publication Date: 2017-07-14
CHENGDU ZHIPULAI BIOMEDICINE TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although afatinib is superior to gefitinib and erlotinib in curative effect, its adverse reactions are also improved compared with them

Method used

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  • Furo[2,3-d]pyrimidine-4-amine derivatives
  • Furo[2,3-d]pyrimidine-4-amine derivatives
  • Furo[2,3-d]pyrimidine-4-amine derivatives

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] The preparation of embodiment 1 compound C-14

[0068] Intermediate I (1 g, 3.01 mmol) was dissolved in THF, triethylamine (0.6 g, 6.02 mmol) was added, and then chloroacetyl chloride (0.37 g, 3.31 mmol) was added dropwise. After the completion of the reaction was monitored by the liquid phase, 3 drops of water were added to quench the reaction, and the solvent was concentrated. Water was added to the residue, extracted with dichloromethane, and the organic phases were combined. The organic phase was washed with saturated ammonium chloride, dried over anhydrous sodium sulfate, and the solvent was concentrated. The residue was subjected to column chromatography to obtain 0.88 g of the compound as a white solid (yield 72%).

[0069] 1 H NMR (400MHz, CDCl3) δppm: 3.80 (s, 3H), 4.25 (s, 2H), 6.81-6.83 (d, J=9.2Hz, 2H), 7.46-7.51 (m, 4H), 7.73-7.76 ( d, J=7.6Hz, 1H), 8.37(s, 1H), 8.3, 9(s, 1H).

Embodiment 2

[0070] The preparation of embodiment 2 compound C-13

[0071] Potassium carbonate (0.89g, 6.47mmol) was added to compound c-14 (0.88g, 2.15mmol) in acetonitrile, then dimethylamine hydrochloride (0.17g, 2.15mmol) was added, the reaction was monitored by TLC, and stirred for 5h. After the reaction was completed, suction was filtered, the solid was washed with a small amount of acetonitrile, and the mother liquor was concentrated. The residue was subjected to column chromatography to obtain 0.55 g of the compound (yield 61%).

[0072] 1 HNMR(DMSO)δ:9.33(s,1H),8.36(s,1H),7.76-7.78(m,2H),7.45-7.49(m,4H),6.80-6.84(m,2H),4.93(s ,2H),3.80(s,3H),3.14(s,2H),2.43(s,6H);

Embodiment 3

[0073] The preparation of embodiment 3 compound C-11

[0074]

[0075] Its preparation method refers to Example 2, the raw materials are c-14 and N-methylpiperazine, the product is a white solid, and the yield is 60%. 1 HNMR(DMSO)δ:9.33(s,1H),8.36(s,1H),7.74-7.76(m,2H),7.46-7.52(m,4H),6.81-6.83(m,2H),4.92(s ,2H),3.80(s,3H),3.20(s,2H),2.51-2.71(m,8H),2.35(s,3H);

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Abstract

The invention discloses compounds represented by the formula (I), stereoisomers, pharmaceutically acceptable salts, or solvates thereof. The invention also provides an application of the abovementioned compounds in the preparation of antitumor drugs, angiogenesis inhibitors, EFGR kinase inhibitors, or AUR A kinase inhibitors.

Description

technical field [0001] The present invention relates to furo[2,3-d]pyrimidin-4-amine derivatives. Background technique [0002] With the deterioration of people's living environment and the continuous increase of mental stress, the number of cancer patients worldwide is increasing year by year. However, the traditional commonly used chemical drugs for the treatment of tumors have poor selectivity, strong side effects and serious drug resistance problems, which are far from meeting the treatment requirements. Therefore, it is very important to develop new anti-tumor drugs with high efficiency and low toxicity in the field of current drug research and development. [0003] In recent years, with the development of molecular biology technology and the further understanding of the pathogenesis at the cellular and molecular levels, it has become important to discover highly effective and low-toxic anticancer drugs by targeting key enzymes in the signaling pathways of tumorigenesis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/048A61K31/519A61K31/5377A61P35/00
CPCY02P20/55C07D491/048
Inventor 王康敏赵刚刘继峰蒲林陈伟
Owner CHENGDU ZHIPULAI BIOMEDICINE TECH CO LTD
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