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

Inactive Publication Date: 2012-03-14
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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  • 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-cyclopentaneglutarimide 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 2h, add 0.87g (4mmol) of 1-(1,2-benzisothiazol-3-yl)piperazine and continue to stir at this temperature for 5h. After the reaction is allowed to cool, it is washed into water and extracted with ethyl acetate. The organic layer was washed with water, washed with brine, dried over magnesium sulfate, concentrated to dry solvent, dissolved in isopropanol, and then added with HCl-EtOH (hydrochloric acid-ethanol) solution to pH=3, a solid precipitated, filtered to obtain a white solid 0.7g, 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-cyclopentane glutarimide hydrochloride

[0022]

[0023] 0.8g (4.4mmol) of 3,3-cyclopentane glutarimide, 0.7g (4.4mmol) of 1-bromo-4-chlorobutane, 1.4g (10.3mmol) of potassium carbonate in 10ml of DMF, stirring 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 allowed to cool, it is washed into water and extracted with ethyl acetate. The organic layer After washing with water, brine, drying with magnesium sulfate, concentrating the dry solvent, adding isopropanol to dissolve, then adding HCl-EtOH solution to pH=3, a solid precipitated, filtered to obtain a white solid 0.6g, mp: 200-204℃, ESI- MS (m / z): 454.56 (M+H).

Embodiment 3

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

[0026]

[0027] 3,3-cyclopentane glutarimide 1g (5.6mmol), 1-bromo-2-chloroethane 0.9g (5.7mmol), potassium carbonate 1.6g (11.7mmol) in 10ml DMF (dimethylformamide) ) Stir at 90°C for 2h, add 1g (4.6mmol) of 1-(1,2-benzisothiazol-3-yl)piperazine and continue stirring at this temperature for 5h. After the reaction is allowed to cool, it is washed into water and a solid is deposited. 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 D 2 And 5-HT 2A N-arylpiperazine derivative with dual binding activity, its preparation method and pharmaceutical composition using the compound as an active ingredient, and their application in the treatment of mental diseases caused by central nervous system dopamine and serotonin transmitter disorders . Background technique [0002] Psychosis is a disorder of the nervous system, and its main type is schizophrenia. The clinical manifestations of schizophrenia can be divided into positive symptoms and negative symptoms. Positive symptoms include hallucinations, delusions, and paranoia; negative symptoms include social disorders, apathy, and anhedonia. Classical antipsychotics such as perphenazine and haloperidol on the market in the early stage are more effective than negative symptoms of schizophrenia. The mechanism of their action is to dopamine D 2 The receptor has a powerful effect, but lacks selectivity in the acti...

Claims

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Application Information

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