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1-phenylpyrazole compounds and medicinal application thereof

A technology of phenylpyrazoles and compounds, applied in the field of new 1-phenylpyrazole compounds, which can solve problems such as the practical application of substances that have not yet realized the generation of active oxygen

Inactive Publication Date: 2000-01-05
MITSUBISHI TANABE PHARMA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, the practical application of a substance capable of inhibiting the generation of active oxygen has not been realized so far.

Method used

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  • 1-phenylpyrazole compounds and medicinal application thereof

Examples

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Embodiment 1

[0065] Add ethyl 2-cyano-3-ethoxyacrylate to the ethanol solution (50 ml) of 3-cyano-4-isobutoxyphenylhydrazine (5 g) obtained in Starting Material Synthesis Example 1 under stirring (4.2 g) and the mixture was heated to reflux for 2 hours. After cooling, the precipitated crystals were collected by filtration to obtain 5.1 g of ethyl 5-amino-1-(3-cyano-4-isobutoxyphenyl)pyrazole-4-carboxylate, melting point 115-117°C. Example 2

Embodiment 2

[0066] To a solution of ethyl 5-amino-1-(3-cyano-4-isobutoxyphenyl)pyrazole-4-carboxylate (1 g) in ethanol (10 ml) was added 1 ml of 5N aqueous hydrochloric acid under stirring, The mixture was refluxed for 2 hours with heating. After the reaction was completed, the reaction mixture was poured into water, and the mixture was neutralized with acetic acid. Precipitated crystals were recrystallized from a mixed solvent of dioxane and water to obtain 0.4 g of 5-amino-1-(3-cyano-4-isobutoxyphenyl)pyrazole-4-carboxylic acid, m.p. 204°C (decomposition). Example 3

Embodiment 3

[0067] Subsequently, ethyl 5-amino-1-(3-cyano-4-isobutoxyphenyl)pyrazole-4-carboxylate (1.64 g) obtained in Example 1 was dissolved in tetrahydrofuran under stirring ( 16 ml) was added isoamyl nitrite (1.75 g), and the mixture was heated to reflux for 1.5 hours. After completion of the reaction, the solvent was evaporated under reduced pressure, and the resulting residue was recrystallized from ethanol to obtain 1.38 g of ethyl 1-(3-cyano-4-isobutoxyphenyl)pyrazole-4-carboxylate, melting point 138 -139°C. Example 4

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Abstract

1-Phenylpyrazole compounds of the formula (1): which is exemplified by 5-amino-1-(3-cyano-4-isobutoxyphenyl)pyrazole-4-carboxylic acid, an optical isomer thereof and a pharmaceutically acceptable salt thereof. These compounds have a xanthine oxidase inhibitory activity and are useful as therapeutic agents for diseases such as hyperuricacidemia and gout.

Description

technical field [0001] The present invention relates to novel 1-phenylpyrazole compounds which have xanthine oxidase inhibitory activity and can be used as therapeutic drugs for hyperuricemia and gout and as therapeutic or preventive drugs for various diseases caused by the generation of active oxygen , the present invention also relates to a pharmaceutical composition containing the compound and a medicament containing the compound. Background technique [0002] The following patent applications have been published concerning xanthine oxidase inhibitors. For example, Japanese Laid-Open Patent Publication 95272 / 1984 discloses 3-phenylpyrazole derivatives with xanthine oxidase inhibitory activity, and Japanese Laid-Open Patent Publication 85379 / 1982 discloses 3-phenylpyrazole derivatives with xanthine oxidase inhibitory activity. Isothiazole derivatives, WO 92 / 09279 discloses 2-phenylthiazole derivatives with xanthine oxidase inhibitory activity, Japanese...

Claims

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Application Information

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IPC IPC(8): C07D231/14
CPCC07D231/14A61P19/06A61P43/00
Inventor 石渕正刚森本浩司福成笃井上浩义中洋一
Owner MITSUBISHI TANABE PHARMA CORP
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