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Pyrazine carboxamide compound

A technology of compound and formamide, applied in the field of pharmaceutical composition, can solve problems such as undisclosed effects

Active Publication Date: 2014-10-01
ASTELLAS PHARMA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0031] However, the above-mentioned documents do not disclose the effect on EGFR T790M mutant kinases and EGFR kinases, and the pyrazine carboxamide compound represented by the following formula (I) of the present invention is in the -L 2 -Y-L 3 -M is different in structure from the compound of formula (K) in terms of the bonded substituted vinyl group

Method used

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Examples

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Embodiment

[0351] Hereinafter, the production method of the compound of formula (I) is demonstrated in more detail based on an Example. It should be noted that the present invention is not limited to the compounds described in the following examples. In addition, the production methods of the raw material compounds are shown in the production examples, respectively. In addition, the production method of the compound of formula (I) is not limited to the production method of the specific examples shown below, and the compound of formula (I) can also be produced by a combination of these production methods or methods obvious to those skilled in the art. to manufacture.

[0352] In addition, the following abbreviations are sometimes used in Examples, Production Examples, and Tables described below.

[0353] PEx: production example number, Ex: example number, PSyn: production example number produced by the same method, Syn: example number produced by the same method (for example, E1 represe...

manufacture example 1

[0358] 3-nitrophenol (1g), 3,5-dichloro-6-ethylpyrazine-2-carboxamide (1.74g), diisopropylethylamine (2.63mL), di The mixture of alkanes (10 mL) was stirred overnight at 80°C. Water was added to the reaction mixture, and the precipitated solid was collected by filtration and dried under reduced pressure to obtain 3-chloro-6-ethyl-5-(3-nitrophenoxy)pyrazine-2 as a white solid. - Formamide (1.68 g).

manufacture example 2

[0360] 3-Chloro-6-ethyl-5-(3-nitrophenoxy)pyrazine-2-carboxamide (500mg), 4-(4-methylpiperazin-1-yl)aniline (300mg) , methanesulfonic acid (201 μL), and N-methylpyrrolidone (2 mL) were heated at 200° C. for 1 hour using a microwave reactor. 4-(4-Methylpiperazin-1-yl)aniline (150 mg) was added to the reaction mixture, followed by heating at 200°C for 30 minutes. A saturated aqueous sodium bicarbonate solution was added to the reaction mixture, and the precipitated solid was collected by filtration and dried. The obtained solid was purified by silica gel column chromatography (eluent; chloroform:methanol:28% ammonia water=1:0:0-200:10:1) to obtain 6-ethyl-3 -{[4-(4-Methylpiperazin-1-yl)phenyl]amino}-5-(3-nitrophenoxy)pyrazine-2-carboxamide (308 mg).

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Abstract

The invention provides a compound that is useful as an inhibitor of EGFR T790M mutation kinase activity. The inventors studied compounds having an inhibiting effect against EGFR T790M mutation kinase and perfected the invention upon confirming that a pyrazine carboxamide compound has an inhibiting effect against EGFR T790M mutation kinase. The pyrazine carboxamide compound of the invention has an inhibiting effect against the EGFR T790M mutation kinase and can be used as a prophylactic and / or therapeutic agent for EGFR T790M mutation-positive cancer, EGFR T790M mutation-positive lung cancer, EGFR T790M mutation-positive non-small cell lung cancer, EGFR T790M mutation protein-positive cancer, and EGFR T90M mutation protein-positive lung cancer.

Description

technical field [0001] The present invention relates to a pharmaceutical composition, for example, a pyrazinecarboxamide compound useful as an active ingredient of a pharmaceutical composition for cancer treatment. Background technique [0002] Lung cancer is caused by the disordered proliferation of cells in the trachea, bronchi, and alveoli. The number of deaths caused by lung cancer accounts for 17% of all cancer deaths, the highest proportion. There are about 1.3 million people in the world every year. People die from lung cancer. [0003] Treatment for lung cancer is broadly classified into surgery (surgical therapy), anticancer agents (chemotherapy), and radiation exposure (radiotherapy), but the effectiveness of the treatment varies depending on the histological type of lung cancer. For example, the diagnosis of lung cancer is made by pathologists through the cytopathological diagnosis of manually obtained microscope specimens, but small cell lung cancer, which accou...

Claims

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Application Information

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IPC IPC(8): C07D241/26C07D401/12C07D401/14C07D403/12C07D413/12C07D471/10C07D491/113A61K31/497A61K31/5377A61P35/00A61P43/00
CPCC07D487/10C07D451/06C07D413/14C07D487/08C07D491/113C07D401/12C07D405/14C07D401/14C07D403/14C07D403/12C07D405/12C07D471/10C07D413/12C07D241/28C07D241/24C07D241/26A61P35/00A61P43/00
Inventor 松矢高广近藤裕岛田逸郎菊池重俊饭田真依子恩田健一福留裕树竹本行弘新堂信昭坂上秀树滨口寿雄
Owner ASTELLAS PHARMA INC
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