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2-oxo-1,2-dihydropyridine-4-carboxylic acid compounds

A technology for dihydropyridine and compounds, which is applied in the field of 2-oxo-1,2-dihydropyridine-4-carboxylic acid compounds, can solve the problems of rare synthesis and application research and the like

Active Publication Date: 2021-07-30
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 3-cyano / carbamoyl-6-substituted phenyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid compounds are a class of small molecular compounds with novel structures, and their synthesis and application research is less See
3-cyano / carbamoyl-6-substituted phenyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid compounds as XO inhibitors and XO fluorescent probes have not been reported yet

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] (1) Cyclization reaction:

[0038](Z)-4-(3-cyano-4-isobutoxyphenyl)-2-hydroxy-4-oxobut-2-enoic acid methyl ester (1.52g, 5mmol), cyanoacetamide (0.42g, 5mmol), anhydrous potassium carbonate (1.38g, 10mmol), were added to 25mL DMF, heated to 57°C for 10h. The reaction solution was poured into 50 mL of water and extracted with ethyl acetate (30 mL×2). The organic phases were combined and dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation. The crude product was recrystallized from ethanol to obtain methyl 3-cyano-6-(3-cyano-4-isobutoxyphenyl)-2-oxo-1,2-dihydropyridine-4-carboxylate, yield 73%.

[0039] (2) Hydrolysis reaction:

[0040] Methyl 3-cyano-6-(3-cyano-4-isobutoxyphenyl)-2-pyridone-4-carboxylate (1.05 g, 3 mmol), 20 mL of 1M NaOH solution, 5 mL of ethanol. Reaction at room temperature for 1.5h. 1M HCl solution was added dropwise to the system to adjust the pH of the system to 5, and a solid precipitated out. Suction filtr...

Embodiment 2

[0042] Example 2: Preparation of 3-carbamoyl-6-(3-cyano-4-isobutoxyphenyl)-2-oxo-1,2-dihydropyridine-4-carboxylic acid (compound 2)

[0043] 3-cyano-6-(3-cyano-4-isobutoxyphenyl)-2-oxo-1,2-dihydropyridine-4-carboxylic acid (compound 1) prepared in Example 1 As a raw material, 3-carbamoyl-6-(3-cyano-4-isobutoxyphenyl)-2-oxo-1,2-dihydropyridine-4-carboxylic acid (compound 2).

[0044] Hydrolysis reaction:

[0045] 3-cyano-6-(3-cyano-4-isobutoxyphenyl)-2-pyridone-4-carboxylic acid (compound 1) (0.34g, 1mmol), 20mL 1M HCl solution, 5mL methanol . The temperature was raised to 55°C for 15h. Part of the solvent was removed by rotary evaporation, and solid was precipitated by cooling. Suction filtration, the filter cake was washed with water, and the crude product was recrystallized from ethanol to obtain 3-carbamoyl-6-(3-cyano-4-isobutoxyphenyl)-2-pyridone-4-carboxylic acid (compound 2) . The total yield was 49% (based on raw material (Z)-4-(3-cyano-4-isobutoxyphenyl)-2-hydro...

Embodiment 3

[0046] Example 3: Preparation of 3-carbamoyl-6-(3-cyano-4-isopropoxyphenyl)-2-oxo-1,2-dihydropyridine-4-carboxylic acid (compound 3)

[0047] Using (Z)-4-(3-cyano-4-isopropoxyphenyl)-2-hydroxyl-4-oxobut-2-enoic acid methyl ester as raw material, through the same method as in Example 2 Obtain 3-carbamoyl-6-(3-cyano-4-isopropoxyphenyl)-2-oxo-1,2-dihydropyridine-4-carboxylic acid (compound 3), the total yield is 45% (based on raw material (Z)-4-(3-cyano-4-isopropoxyphenyl)-2-hydroxyl-4-oxobut-2-enoic acid methyl ester), its structural formula, 1 H-NMR and MS data are listed in Table-1.

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Abstract

The invention belongs to the technical field of medicine, and relates to 3-cyano / carbamoyl-6-substituted phenyl-2-oxo-1,2-dihydropyridine-4-1,2-dihydropyridine-4-1 of general formula I with xanthine oxidase inhibitory activity Formic acid compounds, pharmaceutically acceptable salts, pharmaceutically acceptable solvates and preparation methods thereof, the present invention also relates to the use of these compounds in the treatment of hyperuricemia and gout and the use in the diagnosis of diseases related to xanthine oxidase .

Description

technical field [0001] The invention belongs to the technical field of medicine and relates to 3-cyano / carbamoyl-6-substituted phenyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid compounds and a preparation method, in particular to 3-cyano Base / carbamoyl-6-substituted phenyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid compounds, pharmaceutically acceptable salts, pharmaceutically acceptable solvates and preparation methods thereof, and also The invention relates to the therapeutic use of these compounds in hyperuricemia and gout and the use in the diagnosis of diseases related to xanthine oxidase. Background technique [0002] Gout is an inflammatory disease caused by the deposition of urate in joints and other tissues, which can cause a variety of complications. In most developed countries and some developing countries, its incidence is increasing year by year. Persistent hyperuricemia (hyperuricemia) is one of the important causes of gout. According to available data, the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/85C07D213/82A61K31/4412A61P19/06C09K11/06G01N21/64
CPCA61P19/06C07D213/82C07D213/85C09K11/06C09K2211/1007C09K2211/1029G01N21/643
Inventor 张为革石爱龙包凯关奇张利超杨明正王思博
Owner SHENYANG PHARMA UNIVERSITY
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