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A kind of diaryl ethylene ether compound and its pharmaceutically acceptable salt, synthetic method

A technology of diaryl ethylene ether and synthetic method, which is applied in the fields of organic chemistry, antineoplastic drugs, and drug combinations, etc.

Inactive Publication Date: 2019-09-27
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, patients taking crizotinib often develop drug resistance within 1-2 years, and central nervous system recurrence is more common (Katayama R et al, P Natl Acad Sci USA.108:7535-7540, 2011)

Method used

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  • A kind of diaryl ethylene ether compound and its pharmaceutically acceptable salt, synthetic method
  • A kind of diaryl ethylene ether compound and its pharmaceutically acceptable salt, synthetic method
  • A kind of diaryl ethylene ether compound and its pharmaceutically acceptable salt, synthetic method

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Embodiment Construction

[0042] The present invention and the manner in which the present invention is carried out are further described below in conjunction with the examples. These examples are only for further elucidating the present invention rather than limiting the protection of the present invention thereto.

[0043] The invention will now be further described with reference to the following illustrative examples, in which unless otherwise indicated:

[0044] (1) Temperatures are given in degrees Celsius, operating at room or ambient temperature.

[0045] (2) The organic solution was dried over anhydrous magnesium sulfate.

[0046] (3) The final product has satisfactory proton NMR and mass spectra.

[0047] (4) The yields given are for illustration only, and higher yields can be obtained for process development, and if more are needed, repeat the preparation.

[0048] (5) Column chromatographic purification was carried out using a self-packed silica gel column.

[0049] (6) A quadrupole orb...

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Abstract

The invention provides a diaryl ethyl diether compound and a pharmaceutically acceptable hydrate or salt as well as a synthetic method and anti-tumor application thereof. A structural general formulais as shown in the description. A preparation method comprises the following steps: dissolving 3-hydroxy-2 nitropyridine into DMF, adding 1,2-dibromoethane and potassium carbonate, and carrying out reaction, so that a compound e is obtained; dissolving the compound e into a solvent DMF, then adding a substance (as shown in the description) and potassium carbonate, then heating, and carrying out reaction, so that a compound d is obtained; reducing the compound d by virtue of iron powder, so that a compound c is obtained; dissolving the compound c into acetonitrile solution, and carrying out bromination reaction, so that a product b is obtained; adding the compound b and 1-(1-t-butyloxycarboryl piperidine-4-yl) pyrazole-4-boronic acid pinacol ester into DME, then adding Pd(dppf)Cl2 and Cs2CO3 aqueous solution, and carrying out reaction, so that a compound a is obtained; and adding the compound a into dichloromethane, dropwise adding 1,4-dioxane solution of hydrogen chloride under ice-bath condition, and carrying out reaction, so that the product is obtained. The compound provided by the invention is novel in structure, has the effect of resisting to non-small cell lung cancer and neuroblastoma and has the antitumor activity equivalent to or better than that of a positive control crizotinib.

Description

technical field [0001] The present invention relates to a diaryl ethylene ether compound and its pharmaceutically acceptable salt and its chemical preparation. Background technique [0002] Lung cancer is one of the most important diseases threatening human health. Anaplastic Lymphoma Kinase (Anaplastic Lymphoma Kinase, ALK) positive non-small cell lung cancer accounts for about 5% of the total number of lung cancer patients. Tyrosine kinase inhibitors targeting ALK are powerful means for the treatment of ALK-positive non-small cell lung cancer. Crizotinib is an oral tyrosine kinase inhibitor for the treatment of ALK-positive non-small cell lung cancer. Crizotinib is an ATP-competitive tyrosine kinase inhibitor that has inhibitory effects on tyrosine kinases c-Met, ALK and ROS1 (Segaliny AI et al., J Bone Oncol. 4:1-12, 2015). As the first-generation ALK inhibitor, crizotinib was approved by the US FDA in 2011 for the treatment of advanced ALK-positive non-small cell lung...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/14A61P35/00
Inventor 刘亚军刘沙沙刘晓霞史美云王贺成
Owner DALIAN UNIV OF TECH
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