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Substituted benzopyrone derivatives and application thereof

A technology of benzopyrone and benzopyran, which is applied in the field of substituted benzopyrone derivatives, can solve the problems of EPS side effects, QT gap prolongation, and low ratio, and achieve good anti-schizophrenia activity , the effect of improving negative symptoms

Active Publication Date: 2013-02-27
HUAZHONG UNIV OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Typical antipsychotic drugs generally have severe EPS side effects and are ineffective for one-third of schizophrenic patients
[0005] After the 1960s, a series of new-generation antipsychotic drugs were successively developed, including ziprasidone (Ziprasidone), risperidone (Risperidone), etc., which are called second-generation antipsychotic drugs, namely new antipsychotic drugs Although their respective pharmacological effects are not exactly the same, they have common pharmacological characteristics, that is, they are sensitive to 5-hydroxytryptamine (5-HT) receptors (5-HT1A, 2A, 2C) and norepinephrine (NA). The affinity of the body (α1, α2) is much higher than that of the D2 receptor, resulting in a lower ratio of D2 / 5-HT2A
Compared with the first-generation antipsychotic drugs, its clinical effect has more advantages. It is not only as effective as traditional antipsychotic drugs for positive symptoms, but also effective for negative symptoms and cognitive deficit symptoms, and has a wider spectrum of action. However, these drugs have QT Adverse effects such as gap prolongation, hyperprolactinemia and weight gain

Method used

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  • Substituted benzopyrone derivatives and application thereof
  • Substituted benzopyrone derivatives and application thereof
  • Substituted benzopyrone derivatives and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Example 1, 7-(4-(4-(2-methoxyphenylpiperazine)-n-butoxy))--2hydro-benzopyran-2-one (1);

[0059]

[0060] 1) Take resorcinol 5.5g, d, 1-malic acid 6.7g, add 70% HClO 4 50ml, heated to 90°C to react, the solution gradually became clear, the reaction was completed after 4 hours, cooled to room temperature, the reaction solution was poured into the ice-water mixture, a large amount of solids precipitated, filtered, the filter cake was washed with 95% ethanol Recrystallization gave 4.5 g of white crystals with a melting point of 226-228° C. and a yield of 60.8%.

[0061] 2) Take 5 g of the first step product, 6 g of anhydrous potassium carbonate, 50 ml of acetone, and 8.2 g of 1,4-dibromobutane, heat and reflux for 6 hours, cool to room temperature, filter, and evaporate the solvent to obtain a light yellow oil , and passed through the column to obtain 5.4 g of a white solid with a melting point of 55-57° C. and a yield of 60.7%.

[0062] 3) Take 0.52 g of the second s...

Embodiment 2

[0063] Example 2, 7-(4-(4-(2-methoxyphenylpiperazine)-n-butoxy))-4-methyl-2hydro-chromen-2-one (2)

[0064]

[0065]1) Take 30ml of concentrated sulfuric acid, stir in an ice bath, add 5.5g of resorcinol, dropwise add 9.2g of ethyl acetoacetate, the solution turns from light yellow to yellow, after 18 hours the reaction is complete, pour the reaction solution into the ice-water mixture , a white solid was precipitated, filtered, and the filter cake was washed with water until neutral, and recrystallized with 75% ethanol to obtain 8.5 g of white crystals with a melting point of 186-188°C and a yield of 73.9%.

[0066] 2) Take 5g of the first step product, 6g of anhydrous potassium carbonate, 50ml of acetone and 8.7g of 1,4-dibromobutane, heat to reflux for 4 hours, cool to room temperature, filter, and evaporate the solvent to obtain a light yellow oil , 6.5 g of white solid was obtained through column, the melting point was 58-60° C., and the yield was 77.8%.

[0067] 3) T...

Embodiment 3

[0069] Example 3, 7-(4-(4-(2-methoxyphenylpiperazine)-n-butoxy))-4-phenyl-2hydro-chromen-2-one (3)

[0070] 1) Get resorcinol 5.5g, ethyl benzoyl acetate 9.6g, then add 30ml phosphoric acid, stir at room temperature, the solution turns from light yellow to yellow, after 12 hours the reaction is complete, the reaction solution is poured into the ice-water mixture, A large amount of solids precipitated, filtered, washed the filter cake with water, and recrystallized with 95% ethanol to obtain 9.3 g of white crystals with a melting point of 237-239°C and a yield of 80.9%.

[0071] 2) Take 4.8g of the first step product, 6g of anhydrous potassium carbonate, 50ml of acetone and 8.4g of 1,3-dibromopropane, heat to reflux for 4 hours, cool to room temperature, filter, spin to dry the solvent, and pass through the column to obtain a white solid 5.6g, melting point 67-69°C, yield 78.0%.

[0072] 3) Take 0.5 g of the product of the second step, add 0.6 g of 1-(2-methoxyphenyl) piperazi...

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Abstract

Disclosed are a substituted benzopyran derivative and the use thereof. The substituted benzopyran derivative has the structure of formula (I). It has been found in experiments that the derivative can be used to prepare drugs for treating psychotic conditions.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and specifically relates to substituted benzopyrone derivatives and applications thereof. Background technique [0002] Schizophrenia is a disorder characterized by deep cognitive and emotional dissociations that affect the most basic human behaviors, such as language, thought, perception, and self-awareness. The symptoms of the disease include a wide range, the most common being mental disorders, such as hallucinations, paranoia and delusions. [0003] Schizophrenia is the most serious mental illness, affecting about 1% of people worldwide, and only 5% of all treated patients eventually fully recover. In addition, since schizophrenia often causes comorbidities, such as anxiety disorders, depression, or psychotropic substance abuse, etc., according to a survey by Datamonitor, more than 1 / 3 of patients with schizophrenia suffer from at least one or more Complicated by diseases such as mental i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/16C07D311/18A61K31/496A61P25/18A61P25/22A61P25/24A61P25/06A61P25/08A61P25/16A61P25/14A61P25/28A61P9/10
CPCC07D311/18A61K31/496C07D311/16A61P9/10A61P25/06A61P25/08A61P25/14A61P25/16A61P25/18A61P25/22A61P25/24A61P25/28
Inventor 张桂森陈寅徐祥清刘欣于民权刘笔锋刘志强
Owner HUAZHONG UNIV OF SCI & TECH
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