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Phenylacrylate Derivatives and Their Use as Neuroprotective Drugs

A technology of phenylacrylate derivatives, which is applied in the field of phenylacrylate derivatives, can solve the problems of unstable physical and chemical properties, low oral bioavailability, and can only be administered by injection, and achieve ideal pharmacokinetic characteristics and neuroprotective effects The effect of high activity and low acute toxicity

Active Publication Date: 2022-03-25
SHANGHAI INST OF PHARMA IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, as a neuroprotective agent, Edaravone has unstable physical and chemical properties, low oral bioavailability, and can only be administered by injection for clinical use.

Method used

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  • Phenylacrylate Derivatives and Their Use as Neuroprotective Drugs
  • Phenylacrylate Derivatives and Their Use as Neuroprotective Drugs
  • Phenylacrylate Derivatives and Their Use as Neuroprotective Drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1 (E) Preparation of 3-methyl-1-phenyl-1H-pyrazole-5-(3-(4-hydroxyphenyl))acrylate (T-1)

[0038] 4-Hydroxyphenylacrylic acid (5 mmol, 1.0 eq) was dissolved in 40 mL of dichloromethane at room temperature. Oxalyl chloride (6.5 mmol, 1.3 eq) was slowly added dropwise to the solution at 0-5°C. After the dropwise addition was completed, the reaction was moved to room temperature for 8h. After the reaction was completed, vacuum drying was performed to obtain 4-hydroxyphenylacryloyl chloride.

[0039]At room temperature, phenylhydrazine hydrochloride (7.5 mmol, 1.0 eq) and triethylamine (11.3 mmol, 1.5 eq) were dissolved in 20 mL of absolute ethanol. The reaction solution was heated to 50°C, and ethyl acetoacetate (7.5 mmol, 1.0 eq) was slowly added dropwise. After the dropwise addition was completed, the reaction was refluxed for 24 hours. After the reaction was completed, vacuum drying was performed to obtain 3-methyl-1-phenyl-2-pyrazolin-5-one.

[0040] 3-Met...

Embodiment 2

[0042] Example 2 (E)-3-methyl-1-phenyl-1H-pyrazole-5-(3-(4-hydroxy-3-methoxyphenyl))acrylate (T-2) and its Preparation of salt

[0043] 4-Hydroxy-3-methoxyphenylacrylic acid (5 mmol, 1.0 eq) was dissolved in 40 mL of dichloromethane at room temperature. Oxalyl chloride (6.5 mmol, 1.3 eq) was slowly added dropwise to the solution at 0-5°C. After the dropwise addition was completed, the reaction was moved to room temperature for 8h. After the reaction was completed, vacuum drying was performed to obtain 4-hydroxy-3-methoxyphenylacryloyl chloride.

[0044] At room temperature, phenylhydrazine hydrochloride (7.5 mmol, 1.0 eq) and triethylamine (11.3 mmol, 1.5 eq) were dissolved in 20 mL of absolute ethanol. The reaction solution was heated to 50°C, and ethyl acetoacetate (7.5 mmol, 1.0 eq) was slowly added dropwise. After the dropwise addition was completed, the reaction was refluxed for 24 hours. After the reaction was completed, vacuum drying was performed to obtain 3-methy...

Embodiment 3

[0055] Example 3 Preparation of (E)-3-methyl-1-phenyl-1H-pyrazole-5-(3-(4-methoxyphenyl))acrylate (T-3) and its salts

[0056] 4-Methoxyphenylacrylic acid (5 mmol, 1.0 eq) was dissolved in 40 mL of dichloromethane at room temperature. Oxalyl chloride (6.5 mmol, 1.3 eq) was slowly added dropwise to the solution at 0-5°C. After the dropwise addition was completed, the reaction was moved to room temperature for 8h. After the reaction was completed, vacuum drying was performed to obtain 4-methoxyphenylacryloyl chloride.

[0057] At room temperature, phenylhydrazine hydrochloride (7.5 mmol, 1.0 eq) and triethylamine (11.3 mmol, 1.5 eq) were dissolved in 20 mL of absolute ethanol. The reaction solution was heated to 50°C, and ethyl acetoacetate (7.5 mmol, 1.0 eq) was slowly added dropwise. After the dropwise addition was completed, the reaction was refluxed for 24 hours. After the reaction was completed, vacuum drying was performed to obtain 3-methyl-1-phenyl-2-pyrazolin-5-one. ...

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Abstract

The invention discloses a phenylacrylate derivative and its application as a neuroprotective drug. The advantage of the invention is that the compound and its pharmaceutical preparation are very useful for treating cranial nerve injury diseases, such as cerebral apoplexy and related diseases. Good curative effect, low acute toxicity and no potential risk of cardiotoxicity, compared with existing drugs, it shows outstanding technical effects and substantial scientific progress. The phenylacrylate derivative is a compound represented by general formula I or a salt thereof:

Description

technical field [0001] The present invention relates to phenylacrylate derivatives and their applications. Background technique [0002] Nerve cell damage is characterized by multiple factors, multiple pathways, and multiple links, and the therapeutic effect of only intervening in one link or a single pathway is not significant. In recent years, traditional Chinese medicine has been widely used in the treatment of nervous system diseases and exerts a neuroprotective effect. Traditional Chinese medicine has the advantage of multi-target synergy in the treatment of nerve injury diseases, and can intervene in the pathological process of nerve cell injury in multiple ways. [0003] The inventor found that in traditional Chinese medicine, many monomers or active ingredients with neuroprotective effects contain phenylacrylic acid (ester) structure, such as: 1 , B 1 , B 2 , C 1 It is a natural neuroprotective agent against the damage of glutamic acid to nerve cells; p-methoxyc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/22C07D231/34A61K31/415A61P9/10A61P7/02A61P25/00
CPCC07D231/22C07D231/34
Inventor 李建其张庆伟李洋周超
Owner SHANGHAI INST OF PHARMA IND CO LTD
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