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Indolinone compound

A compound, the technology of -CON, applied in the field of indolinone compounds, can solve the problem of no disclosure and suggestion of TRPA1 channel activation or digestive system function improvement.

Inactive Publication Date: 2011-03-02
ASTELLAS PHARMA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0058] However, there is no disclosure or hint that the present invention is involved in the activation of TRPAl channels or the improvement of digestive system function.

Method used

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  • Indolinone compound
  • Indolinone compound
  • Indolinone compound

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0274] Dissolve 1.651g 7-fluoro-1H-indole-2,3-dione in 10mL DMF, add 600mg 60% sodium hydride oil solution under ice-cooling, stir for 30 minutes, then add 1.10mL 1-bromo-2- Methylpropane, stirred for 4 hours. The solvent was distilled off under reduced pressure, and the residue was diluted with ethyl acetate and washed successively with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10) to obtain 1.032 g of 7-fluoro-1-isobutyl -1H-indole-2,3-dione.

preparation example 2

[0276] Dissolve 600mg of 1,3-dihydro-2H-indol-2-one in 15mL of EtOH, add 794mg of 1-methyl-1H-imidazole-2-carbaldehyde (Calvarde) and 0.06mL of piperidine, at 75°C Stir for 1 hour. The precipitated solid was collected by filtration to obtain 1.180 g of 3-[(1-methyl-1H-imidazol-2-yl)methylene]-1,3-dihydro-2H-indol-2-one.

preparation example 3

[0278] 1.027g of 7-fluoro-1-isobutyl-1H-indole-2,3-diketone was dissolved in 10mL THF, and 1.779g (triphenylphosphorous) ethyl acetate ((Trifenylphosphorous) ethyl acetate ( Liden) acetic acid Echel), stirred at 60°C for 10 hours. The solvent was distilled off under reduced pressure, and the residue was dissolved in ethyl acetate, and washed successively with saturated sodium bicarbonate water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10) to obtain 724 mg of (2E)-(7-fluoro-1 - ethyl isobutyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)acetate.

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Abstract

Disclosed is a compound useful as an active ingredient for a pharmaceutical composition, such as a pharmaceutical composition for the treatment of constipation-type irritable bowel syndrome, atonic constipation and / or functional gastrointestinal disorder. Studies have been made extensively on compounds having a TRPA1 channel activation activity, and it is confirmed that an indolinone compound represented by formula (1) has a TRPA1 channel activation activity. The indolinone compound has a TRPA1 channel activation activity and can be used as an active ingredient for a pharmaceutical composition for the prevention and / or treatment of constipation-type irritable bowel syndrome, atonic constipation and / or functional gastrointestinal disorder or the like. [In the formula, R1 represents -CO2H, a biological equivalent thereof or the like; R2 represents a hetero ring, an aryl, a C3-8-cycloalkyl, -CO-C1-6-alkyl, -H, a -C1-6-alkyl or the like; R3 represents -H, a -C1-6-alkyl, a halogen, -NO2, -CN, a -O-C1-6-alkyl or the like; and a broken line represents a Z-olefin, an E-olefin or a mixture thereof.

Description

technical field [0001] The present invention relates to indolinones ( indolinone) compound. Background technique [0002] 90% of 5-hydroxytryptamine (serotonin; hereinafter referred to as "5-HT") exists in the gastrointestinal tract in the body. 5-HT in the gastrointestinal tract is synthesized by chromaffin cells (enterochromaffin cells; hereinafter referred to as "EC cells") of the gastrointestinal mucosa, enters the blood, and is transported throughout the body. The free 5-HT combined with the 5-HT receptors of the target cells through the chemical stimulation and mechanical stimulation of the intestinal tract causes a physiological response. As 5-HT receptors involved in digestive tract motility, 5-HT receptor 1, 5-HT receptor 2, 5-HT receptor 3, 5-HT receptor 4, and 5-HT receptor 7 have been identified Wait. It has been established that these receptors are expressed in nerve cells or smooth muscle of the gastrointestinal tract. 5-HT released from EC cells controls ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/34A61K31/4045A61K31/405A61K31/4178A61K31/427A61K31/4439A61K31/5377A61P1/04A61P1/14C07D401/06C07D403/06C07D405/06C07D417/06
CPCC07D405/06C07D209/38C07D403/06C07D401/06C07D209/34C07D417/06A61P1/04A61P1/10A61P1/12A61P1/14
Inventor 加来英贵宅和知文影山路人野泽桂土居原仁
Owner ASTELLAS PHARMA INC
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