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A compound for ischemia-reperfusion injury and its preparation method

A technology of ischemia-reperfusion and compounds, applied in the field of medicinal chemistry

Active Publication Date: 2020-08-28
武汉惠康达科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the occurrence and development mechanism of myocardial hypertrophy is still not completely clear. The existing research and findings still have certain limitations in clinical practice, and it is not yet possible to form a truly effective prevention and treatment measure for myocardial hypertrophy.

Method used

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  • A compound for ischemia-reperfusion injury and its preparation method
  • A compound for ischemia-reperfusion injury and its preparation method
  • A compound for ischemia-reperfusion injury and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] Embodiment 1. Preparation of compound 3

[0070]

[0071] Compound 1 (50g, 332.89mmol, 1eq) was dissolved in 500mL of anhydrous tetrahydrofuran, then pyridine (52.92g, 669.03mmol, 54mL, 2.01eq) and 4-dimethylaminopyridine (814mg, 6.66mmol, 0.02eq) were added, Then 4-nitrobenzenesulfonyl chloride (89g, 401.59mmol, 1.21eq) was slowly added at 0°C, and the resulting mixture was stirred at 25°C for 6 hours. LC-MS (EW9132-1-P1A) showed that the main peak was the target signal peak, the reaction solution was filtered, the filter cake was slurried in 300mL of ethyl acetate, and the resulting solid was dried to obtain compound 3 (100g, 255.25mmol, 76.68%yield, 85.6%purity) of a yellow solid, which was analyzed by LC-MS ( EW9132-1-P1B) and NMR (EW9132-1-PA) characterization.

Embodiment 2

[0072] Embodiment 2. Preparation of compound 4

[0073]

[0074] Compound 3 (5.00g, 14.91mmol, 1.00eq), zinc powder (4.00g, 61.17mmol, 4.10eq) and glacial acetic acid (3.68g, 61.20mmol, 4.10eq) were added to 75mL of methanol, at 60 degrees Celsius Stir for 2 hours, thin-layer chromatography (volume ratio: petroleum ether / ethyl acetate=1:1, main point Rf value 0.4) shows that the raw material has been consumed, the reaction solution is filtered, and the filter cake is washed with 100 ml of hot methanol , the filtrate was concentrated and then purified by silica gel column chromatography (petroleum ether ethyl acetate system, 10:1 to 2:1) to obtain compound 4 (3.00 g, 9.82 mmol, 65.86% yield) as a yellow solid.

Embodiment 3

[0075] Embodiment 3. Preparation of compound 5

[0076]

[0077] Compound 4 (0.10g, 0.33mmol) and 2-hydroxy-3-methoxybenzaldehyde (0.075g, 0.491mmol) were heated to reflux in 1.5ml of ethanol for 18 hours, and sodium borohydride (0.04 g, 0.98mmol)) and continued to stir for 6 hours, then quenched with 1 ml of methanol and 1 ml of water and continued to stir for 20 minutes, the mixture was filtered with celite, the filtrate was concentrated to dryness and purified by preparative HPLC Compound 5 was obtained.

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PUM

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Abstract

Provided in the present invention is a compound of formula (I) or pharmaceutically acceptable salt, solvate or metabolite thereof, which can be used for treating and / or preventing ischemia-reperfusion injury and related diseases, acute respiratory distress syndrome and related diseases, acute lung injury and related diseases, pathological cardiac hypertrophy and related diseases, and / or fatty liver disease and related diseases.

Description

technical field [0001] The present invention belongs to the technical field of medicinal chemistry, and in particular relates to the compound of formula (I) or its pharmaceutically acceptable salt, solvate or metabolite, its preparation method and application. Background technique [0002] Ischemia-Reperfusion Injury (Ischemia-Reperfusion Injury, IRI) is a concept first proposed by Jennings in 1960. It refers to blood reperfusion after tissue and organ ischemia, which not only fails to restore the function of the tissue and organ, but aggravates the dysfunction and structure of the tissue and organ. damage. Ischemia-reperfusion injury can occur in many important organs, including the heart, liver, lung, kidney, and gastrointestinal tract. Studies have shown that inflammatory burst and cell death are the main pathological mechanisms leading to organ damage caused by ischemia-reperfusion. How to reduce and eliminate ischemia-reperfusion injury and clarify the mechanism of th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/26C07H1/00A61K31/7056A61P9/10A61P11/00A61P9/00A61P1/16A61P13/12
CPCC07H1/00C07H15/26A61K31/63A61K31/7056A61P1/16A61P9/00A61P9/10A61P11/00A61P13/12C07D277/82
Inventor 李红良张晓晶
Owner 武汉惠康达科技有限公司