Substituted benzopyrone derivatives and applications 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: 2011-12-07
HUAZHONG UNIV OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented chemicals are modified versions of existing drugs called bicenoxapine or chlorpromptor which were previously developed but they still had some limitations like side effect issues caused when used alone. These modifications made them more effective at treating certain types of neurology diseases including Schizophreath syndrome (SCH), Parkinson' s disease (PD) etc., while also improving their ability to fight against other forms of psychosis associated with these conditions.

Problems solved by technology

This patented technical problem addressed in this patents relates to developing improved medications for neurological diseases like depression, anxiety, managing stress, attention deficits, autistic behaviors, improves overall health outcomes during therapy.

Method used

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  • Substituted benzopyrone derivatives and applications thereof
  • Substituted benzopyrone derivatives and applications thereof
  • Substituted benzopyrone derivatives and applications 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

The invention belongs to the field of pharmaceutical chemistry and particularly relates to substituted benzopyrone derivatives and application thereof. The substituted benzopyrone derivatives have a structure shown in a formula (I), and the experiments show that the compounds can be used in preparing medicaments for the treatment of neuropsychiatric diseases.

Description

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Claims

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Application Information

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Owner HUAZHONG UNIV OF SCI & TECH
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