N-aryl piperazine derivative having double activity of dopamine D2 and 5-HT2a

A piperazine and alkyl technology, applied in the field of N-arylpiperazine compounds, can solve problems such as adverse reactions and lack of selectivity in action

Inactive Publication Date: 2010-10-27
JIANGSU HANSOH PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The classic antipsychotic drugs listed in the early stage, such as perphenazine and haloperidol, have better curative effects on positive symptoms of schizophrenia than negative symptoms, and their mechanism of action is the effect on dopamine D 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 having double activity of dopamine D2 and 5-HT2a
  • N-aryl piperazine derivative having double activity of dopamine D2 and 5-HT2a
  • N-aryl piperazine derivative having double activity of dopamine D2 and 5-HT2a

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] 3-[2-[4-(2,3-Dichlorophenyl)piperazin-1-yl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[ 1,2-a] Preparation of pyrimidin-4-one

[0025] N-(2,3-dichlorophenyl)piperazine hydrochloride (0.6g, 2mmol), 3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl -4H-pyrido[1,2-a]pyrimidin-4-one (0.5g, 2.2mmol), potassium carbonate (0.91g, 6.6mmol) and DMF (10ml) were put into the reaction flask, and the reaction was stirred at 100°C 4 hours. The reaction solution was cooled and poured into water, extracted with ethyl acetate, the organic layer was washed with water and brine in turn, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated to dryness under reduced pressure, and purified by column chromatography to obtain the title compound: 0.33 g.

[0026] ESI-MS (m / z): 422.36 (M+H),

[0027] 1 H NMR (CDCl 3 , 400M) δ: 1.85-1.97(m, 4H), 2.30(s, 3H), 2.55-2.59(m, 2H), 2.75-2.87(m, 8H), 3.09(t, 4H), 3.93(t, 2H), 6.95(m, 1H), 7.13(m, 2H)

Embodiment 2

[0029] 3-[3-[4-(2,3-dichlorophenyl)piperazin-1-yl]propyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[ 1,2-a] Preparation of pyrimidin-4-one

[0030] The preparation method is the same as in Example 1, except that the reaction raw material is made of 3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2- a] pyrimidin-4-one (0.5g) was changed to 3-(3-chloropropyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a] Pyrimidin-4-one (0.53 g).

[0031] ESI-MS (m / z): 436.2 (M+H)

Embodiment 3

[0033] 3-[4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[ 1,2-a] Preparation of pyrimidin-4-one

[0034] The preparation method is the same as in Example 1, except that the reaction raw material is made of 3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2- a] pyrimidin-4-one (0.5g) was changed to 3-(4-chlorobutyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a] Pyrimidin-4-one (0.56 g).

[0035] ESI-MS (m / z): 450.5 (M+H)

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Abstract

The invention relates to a novel N-aryl piperazine compound having double activity of dopamine D2 and 5-HT2a, a preparation method, a medicine combination containing the compound and an application thereof on treating mental diseases.

Description

technical field [0001] The present invention relates to a novel class of D 2 and 5-HT 2a Dual active N-arylpiperazine compounds, pharmaceutical compositions containing these compounds and their use in treating mental diseases. Background technique [0002] Mental illness 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, and negative symptoms include social disturbances, apathy, and anhedonia. The classic antipsychotic drugs 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 and striatal regions of the brain, resulting in extrapyramidal adverse effects. Therefore, it is the main research direction...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07D209/34C07D209/48C07D221/20C07D295/088C07D209/08C07D215/26C07D495/04A61K31/519A61K31/496A61K31/495A61P25/00A61P25/18
Inventor 岑均达唐家邓
Owner JIANGSU HANSOH PHARMA CO LTD
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