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Substitute ixoxazolylthiophene compounds

A technology of isoxazolylthiophene and compounds, which is applied in the field of substituted isoxazolylthiophene compounds, and can solve the problems of undocumented compounds, etc.

Inactive Publication Date: 2003-08-06
TAISHO PHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Compounds that have been reported to have curative or preventive effects against osteopathy or neuropathy by enhancing the action of cell differentiation-inducing factors present in or administered to a living body include fused thiophene derivatives disclosed in WO98 / 09958, but this report Compounds of the present invention are not described in

Method used

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  • Substitute ixoxazolylthiophene compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] 3,4'-Dimethyl-4-(isoxazol-5-yl)-5-(methylthio)thiophene-2-carboxamide

[0059] a) Ethyl 3-methyl-5-methylthio-4-propionylthiophene-2-carboxylate

[0060] Add 85% aqueous solution (8ml) containing potassium hydroxide (13.6g, 175.2mmol) dropwise to a solution containing 2,4-hexanedione (10.0g, 87.6mmol) in dimethyl sulfoxide (88ml) under ice cooling ) and carbon disulfide (7.3 g, 96.4 mmol), and the mixture was stirred at this temperature for 30 minutes. Next, a solution containing ethyl bromoacetate (13.2 g, 78.8 mmol) in dimethylsulfoxide (8 ml) was added dropwise under ice-cooling, and the mixture was stirred at this temperature for 30 minutes. Iodomethane (12.4 g, 87.6 mmol) was then added, and the mixture was stirred for a further 20 minutes. The reaction solution was extracted with ethyl acetate, and the organic layer was washed (successively with water and saturated aqueous sodium chloride), dried (over anhydrous magnesium sulfate), filtered and concentrated und...

Embodiment 2

[0071] 3-Ethyl-4-(4-methylisoxazol-5-yl)-5-(methylthio)thiophene-2-carbonitrile

[0072] a) 3-Ethyl-5-methylthio-4-propionylthiophene-2-carbonitrile

[0073] To a solution containing 2,4-heptanedione (10.0 g, 78.0 mmol) in dimethylsulfoxide (100 ml), an 85% aqueous solution containing potassium hydroxide (10.3 g, 156.0 mmol) was successively added dropwise under ice-cooling ( 10ml) and carbon disulfide (5.9g, 78.0mmol), then the mixture was stirred at this temperature for 30 minutes. Next, a solution containing chloroacetonitrile (5.3 g, 70.2 mmol) in dimethylsulfoxide (10 ml) was added dropwise over 5 minutes under ice-cooling, and the mixture was stirred at this temperature for 20 minutes. Potassium carbonate (10.8 g, 78.0 mmol) and iodomethane (12.2 g, 85.8 mmol) were then added, and the mixture was stirred for a further 30 minutes. The reaction solution was extracted with ethyl acetate, and the organic layer was washed (successively with water and saturated aqueous sod...

Embodiment 3

[0079] 3-Ethyl-4-(4-methylisoxazol-5-yl)-5-(methylthio)thiophene-2-carboxamide

[0080] To 3-ethyl-4-(4-methylisoxazol-5-yl)-5-(methylthio)thiophene-2-carbonitrile (0.87g, 3.3mmol) was added concentrated sulfuric acid (11ml) and The mixture was heated at 60°C for 1.5 hours. The reaction solution was cooled to room temperature, ice was added, and the mixture was extracted with ethyl acetate. The organic layer was washed (successively with water, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride), dried (over anhydrous magnesium sulfate), and concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (developing solvent: chloroform / ethyl acetate=1:0-3:1), and recrystallized in ether to obtain 3-ethyl-4-(4-methyl (isoxazol-5-yl)-5-(methylthio)thiophene-2-carboxamide (0.39 g, 42%) as colorless crystals.

[0081] Melting point: 93.5-94.5°C

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Abstract

This invention provides a substituted isoxazolylthiophene compound represented by the formulawherein R1 and R2 individually represent an alkyl group of 1-5 carbon atoms, R3 represents a cyano group or a group CONR5R6 (in which R5 and R6 individually represent a hydrogen atom or an alkyl group of 1-10 carbon atoms), R4 represents an alkyl group of 1-5 carbon atoms or a phenyl group, and n is an integer of 0-2, or a salt thereof.The compounds of the invention are useful for the treatment or prevention of various bone diseases or nerve diseases, because they specifically enhance the action of the cell differentiation induction factors found in a living body.

Description

technical field [0001] The present invention relates to novel substituted isoxazolylthiophene compounds and pharmaceutical compositions containing such compounds as active ingredients, which compounds are useful for potentiating the action of cell differentiation-inducing factors. Background technique [0002] Compounds that have been reported to have curative or preventive effects against osteopathy or neuropathy by enhancing the action of cell differentiation-inducing factors present in or administered to a living body include fused thiophene derivatives disclosed in WO98 / 09958, but this report No compound of the present invention is described in . Contents of the invention [0003] The present inventors conducted extensive research and found that some substituted isoxazolylthiophene compounds are effective in treating or preventing bone disease or neuropathy, and finally completed the present invention. [0004] More specifically, the present invention relates to a sub...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/04
CPCC07D413/04
Inventor 原田真宏武田顺子中村年男斋藤秀次
Owner TAISHO PHARMACEUTICAL CO LTD
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