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N-aryl piperazine derivative and preparation method thereof and drug composition adopting N-aryl piperazine derivative as active ingredient

A technology of arylpiperazine and derivatives, applied in the field of N-arylpiperazine derivatives, can solve problems such as adverse reactions and lack of selectivity in action, and achieve the effect of reducing side effects and improving negative symptoms and positive symptoms

Inactive Publication Date: 2009-11-11
SHANGHAI INST OF PHARMA IND
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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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  • N-aryl piperazine derivative and preparation method thereof and drug composition adopting N-aryl piperazine derivative as active ingredient
  • N-aryl piperazine derivative and preparation method thereof and drug composition adopting N-aryl piperazine derivative as active ingredient
  • N-aryl piperazine derivative and preparation method thereof and drug composition adopting N-aryl piperazine derivative as active ingredient

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] N-[3-[4-(1,2-Benzisothiazol-3-yl)-1-piperazinyl]propyl]-3,3-cyclopentane glutarimide hydrochloride

[0018]

[0019] 3,3-cyclopentane glutarimide 0.9g (5mmol), 1-bromo-3-chloropropane 0.79g (5mmol), potassium carbonate 1.5g (11mmol) in 10ml DMF (dimethylformamide) 90 Stir at ℃ for 2 h, add 0.87 g (4 mmol) of 1-(1,2-benzisothiazol-3-yl) piperazine and continue to stir at this temperature for 5 h, let the reaction cool down, pour into water, extract with ethyl acetate, The organic layer was washed with water, washed with brine, dried over magnesium sulfate, concentrated to dryness, dissolved in isopropanol, added HCl-EtOH (hydrochloric acid-ethanol) solution to pH=3, a solid precipitated, filtered to obtain 0.7 g of a white solid, mp( Melting point): 250°C, ESI-MS (m / z): 440.54 (M+H).

Embodiment 2

[0021] N-[4-[4-(1,2-Benzisothiazol-3-yl)-1-piperazinyl]butyl]-3,3-cyclopentaneglutarimide hydrochloride

[0022]

[0023] 0.8g (4.4mmol) of 3,3-cyclopentane glutarimide, 0.7g (4.4mmol) of 1-bromo-4-chlorobutane, and 1.4g (10.3mmol) of potassium carbonate were stirred in 10ml DMF at 90°C for 2h , add 0.8g (3.7mmol) of 1-(1,2-benzisothiazol-3-yl)piperazine and continue to stir at this temperature for 5h. After the reaction is left to cool, it is washed into water, extracted with ethyl acetate, and the organic layer is Washed with water, washed with brine, dried over magnesium sulfate, concentrated to dryness, dissolved in isopropanol, added HCl-EtOH solution to pH = 3, precipitated solid, filtered to obtain 0.6g of white solid, mp: 200-204°C, ESI- MS (m / z): 454.56 (M+H).

Embodiment 3

[0025] N-[2-[4-(1,2-Benzisothiazol-3-yl)-1-piperazinyl]ethyl]-3,3-cyclopentaneglutarimide

[0026]

[0027] 3,3-cyclopentane glutarimide 1g (5.6mmol), 1-bromo-2-chloroethane 0.9g (5.7mmol), potassium carbonate 1.6g (11.7mmol) in 10mlDMF (dimethylformamide ) at 90°C for 2 h, add 1 g (4.6 mmol) of 1-(1,2-benzisothiazol-3-yl) piperazine and continue to stir at this temperature for 5 h, let the reaction cool down and pour into water to precipitate a solid. 0.8 g of white solid was obtained by filtration, mp (melting point): 280° C., ESI-MS (m / z): 431.52 (M+H).

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Abstract

The invention provides an N-aryl piperazine derivative, i.e. a compound shown in formula (I) or pharmaceutically acceptable salt, wherein n is 1-6. The invention provides the compound shown in formula (I) and a drug composition thereof which have excellent effect in treating nervous and mental diseases caused by central nervous system dopamine and serotonin transmittance disorder.

Description

technical field [0001] The present invention relates to a 2 and 5-HT 2A N-arylpiperazine derivatives with dual binding activity, preparation method thereof, pharmaceutical composition containing the compound as an active ingredient, and their application in treating mental diseases caused by central nervous system dopamine and serotonin 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 mesolimbic system...

Claims

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Application Information

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IPC IPC(8): C07D417/12A61K31/496A61P25/18
Inventor 岑均达吴海波王霞
Owner SHANGHAI INST OF PHARMA IND
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