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Dihydro quinolinone derivative, preparation method thereof and medicine composition taking same as main active ingredient

A technology of dihydroquinolinone and derivatives, applied in the direction of drug combination, organic active ingredients, medical preparations containing active ingredients, etc., can solve the problems of lack of selectivity and adverse reactions, and achieve improvement of negative symptoms and positive symptoms Symptoms, side effect reduction effect

Inactive Publication Date: 2009-12-23
SHANGHAI INST OF PHARMA IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The classic antipsychotics listed in the early stage, such as perphenazine and haloperidol, have better curative effect on positive symptoms of schizophrenia than negative symptoms. 2 Receptor is potent but lacks selectivity for action on the mesolimbic system and striatal regions of the brain, resulting in extrapyramidal adverse effects

Method used

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  • Dihydro quinolinone derivative, preparation method thereof and medicine composition taking same as main active ingredient
  • Dihydro quinolinone derivative, preparation method thereof and medicine composition taking same as main active ingredient
  • Dihydro quinolinone derivative, preparation method thereof and medicine composition taking same as main active ingredient

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1: Preparation of 7-(2-chloroethoxy)-3,4-dihydro-2(1H)-quinolinone

[0019]

[0020] 5g of 7-hydroxy-3,4-dihydro-2(1H)-quinolinone, 8.5g of potassium carbonate, 50ml of 1,2-dichloroethane were refluxed in 25ml of DMF (dimethylformamide) for 12h, and the reaction solution Rinse into water, extract with ethyl acetate, wash the organic layer once with 10% sodium hydroxide solution, wash with water again, then dry over magnesium sulfate, concentrate under reduced pressure, stir the residual solid with toluene, filter, and dry to obtain 3.3 g of white powder , mp (melting point): 130-132°C.

Embodiment 2

[0021] Example 2: Preparation of 7-(3-chloropropoxy)-3,4-dihydro-2(1H)-quinolinone

[0022]

[0023] 5g of 7-hydroxy-3,4-dihydro-2(1H)-quinolinone, 8.5g of potassium carbonate, and 9.4g of 1-bromo-3-chloropropane were stirred in 25ml of DMF at 70°C for 3h, and the reaction solution was poured into water. After stirring for a while, a solid precipitated out, filtered, and the filter cake was recrystallized in methanol to obtain 5.7 g of white powder, mp: 116-120°C.

Embodiment 3

[0024] Example 3: 7-(4-chlorobutoxy)-3,4-dihydro-2(1H)-quinolinone

[0025]

[0026] 5g of 7-hydroxy-3,4-dihydro-2(1H)-quinolinone, 8.5g of potassium carbonate, and 10.5g of 1-bromo-4-chlorobutane were stirred in 25ml of DMF at 70°C for 3h, and the reaction solution was washed into water , after stirring for a while, a solid precipitated out, filtered, and the filter cake was recrystallized in methanol to obtain 5.0 g of white powder, mp: 102-104°C.

[0027] Preparation of Dihydroquinolinone Derivatives

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PUM

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Abstract

The invention provides a novel dihydro quinolinone derivative, namely a compound shown as the formula (I) or the salt of the compound, which is pharmaceutically acceptable and described as the right formula; wherein n can be any number between 1 and 6, and A can be the formula (II) or the formula (III) with the structure shown as the right formula. The medicine composition containing the compound shown as the formula (I) has good curative effect on treating mental diseases caused by central nervous system dopamine and 5-hydroxytryptamine neurotransmitter disorder.

Description

technical field [0001] The present invention relates to a 2 and 5-HT 2A A dihydroquinolinone derivative with dual binding activity, a preparation method thereof, a pharmaceutical composition containing the compound as an active ingredient, and their application in treating mental diseases caused by central nervous system dopamine and 5-hydroxytryptamine transmitter disturbances. Background technique [0002] Psychosis is a nervous system disorder, the main type of which is schizophrenia. The clinical manifestations of schizophrenia can be divided into two kinds of positive symptoms and negative symptoms. Positive symptoms include hallucinations, delusions, and paranoia; negative symptoms include social disturbances, apathy, and anhedonia. The classic antipsychotics listed in the early stage, such as perphenazine and haloperidol, have better curative effect on positive symptoms of schizophrenia than negative symptoms. 2 Receptors are potent, but lack selectivity in the me...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/14C07D417/12A61K31/4709A61K31/496A61P25/18
Inventor 岑均达吴海波王霞
Owner SHANGHAI INST OF PHARMA IND CO LTD