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Xanthine oxidase inhibitor and application thereof

A compound, alkoxy technology, applied in the direction of anti-inflammatory agents, organic chemistry, non-central analgesics, etc., can solve problems such as large toxic and side effects

Active Publication Date: 2017-03-08
JIANGSU ATOM BIOSCI & PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, a variety of highly active compounds have entered clinical trials, but they still face many problems such as high toxicity and side effects, and further research is needed

Method used

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  • Xanthine oxidase inhibitor and application thereof
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  • Xanthine oxidase inhibitor and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] Example 1: Synthesis of 2-(7-cyano-2-ethylbenzofuran-5-yl)-4-methylthiazole-5-carboxylic acid (9)

[0083]

[0084] Step A: Methyl p-hydroxybenzoate (13.7g, 90.0mmol) was dissolved in methanesulfonic acid (150mL), and hexamethylenetetramine (HMTA) (25.2g, 180mmol) was added, and the resulting mixture was heated at 100°C under nitrogen Stir overnight. Cool to room temperature, add concentrated hydrochloric acid (24 mL) and water (300 mL), and stir at room temperature for 30 minutes. Extracted with ethyl acetate (100 mL×2), dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the product was purified by column chromatography (200-300 mesh silica gel, ethyl acetate: petroleum ether = 1:20 elution) to obtain methyl 3-formyl-4-hydroxybenzoate (1) ( 4.0g). The yield is 24.7%.

[0085] Step B: Add NBS (3.95g, 22.2mmol) in DMF (40mL) solution dropwise to Compound 1 (4.0g, 22.2mmol) in DMF (60mL) solution in about 40 minutes under ic...

Embodiment 2

[0093] Example 2: Synthesis of 2-(7-bromo-2-ethylbenzofuran-5-yl)-4-methylthiazole-5-carboxylic acid (10)

[0094]

[0095] Compound 7 was hydrolyzed according to the method of experimental step I in Example 1, and acidified to obtain 2-(7-bromo-2-ethylbenzofuran-5-yl)-4-methylthiazole-5-carboxylic acid (10) . 1 H NMR (DMSO-d 6 , 300MHz) δ8.17(s, 1H), 8.02(s, 1H), 6.82(s, 1H), 2.86(q, J=7.2Hz, 2H), 2.67(s, 3H), 1.29(t, J = 7.2Hz, 3H). MS (EI, m / z): 366.0 [M-H] - .

Embodiment 3

[0096] Example 3: Synthesis of 2-(7-cyano-2-isopropylbenzofuran-5-yl)-4-methylthiazole-5-carboxylic acid (18)

[0097]

[0098] Step A: Methyl p-hydroxybenzoate (10 g, 65.7 mmol), sodium acetate hydrate (18.78 g, 138 mmol) and iodine (35 g, 137.9 mmol) were added to methanol (150 mL), and the resulting mixture was stirred at reflux for 1.5 hours. A solution of sodium hydroxide (5.52 g, 138 mmol) in water (200 mL) was added, followed by reflux for 2.5 hours. Cool to room temperature, add dilute sodium bisulfite solution until the color fades. After filtering, the filter cake was washed with a small amount of water, then dissolved with ethyl acetate (200 mL), and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained product was recrystallized from petroleum ether / ethyl acetate to obtain methyl 4-hydroxy-3,5-diiodobenzoate (11) (23g). The yield was 86.7%. 1 H NMR (DMSO-d 6 , 500MHz) δ10.44 (s, 1H), 8.23 ​​(s, 2H), 3.81 ...

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Abstract

The invention discloses a xanthine oxidase inhibitor and application thereof. The xanthine oxidase inhibitor is a compound shown as a general formula (I) and is a pharmaceutically acceptable salt. The xanthine oxidase inhibitor, which is the compound and the pharmaceutically acceptable salt, can be applied to preparation of the xanthine oxidase inhibitor and particularly applied to preparation of medicines for preventing or treating hypeluricemia diseases, gout or diabetic nephropathy.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a class of xanthine oxidase inhibitors and their application in medicine. Background technique [0002] Gout is caused by hyperuricemia. Due to the disorder of purine metabolism in the human body, excessive uric acid production and poor uric acid excretion are caused, and the blood uric acid level continues to rise. With the supersaturation of blood uric acid concentration, the sodium urate crystallizes and deposits in joints and soft tissues, causing the inflammatory pain response of gout. Uric acid is the end product of purine metabolism in nucleic acid (including nucleic acid in food) in the human body. It is generally believed that hyperuricemia occurs when the uric acid content in male serum exceeds 7 mg / dL and in female serum exceeds 6 mg / dL. [0003] Gout is the second most common metabolic disease after diabetes, and has been listed by the United Nations a...

Claims

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Application Information

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IPC IPC(8): C07D417/04C07D421/04A61K31/427A61K31/41A61P19/06A61P13/12A61P19/02A61P29/00A61P3/10A61P9/12A61P9/04A61P9/00A61P25/00
Inventor 史东方傅长金承曦
Owner JIANGSU ATOM BIOSCI & PHARMA CO LTD
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