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Preparation method of antipsychotic drug olanzapine

A technology of antipsychotics and olanzapine, applied in the direction of organic chemistry, can solve the problems of high production cycle and cost, complicated process and post-processing, and high requirements for reaction conditions, and achieve cost reduction, high product yield, and post-processing Easy to handle effects

Active Publication Date: 2013-11-27
宁波人健化学制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When the method shown above is applied to industrialized production, the reaction conditions are high, the process and post-treatment are complicated, the synthetic route is too long, the production cycle and cost are high, and some of the steps cannot be well applied to industrialized production.

Method used

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  • Preparation method of antipsychotic drug olanzapine
  • Preparation method of antipsychotic drug olanzapine
  • Preparation method of antipsychotic drug olanzapine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Malononitrile (66.1g, 1.0mol), sulfur (32.0g, 1.0mol), triethylamine (10.1g, 0.1mol) and DMF (200mL) were placed in a 1000mL reaction flask, and propionaldehyde ( 61.0g, 1.05mol) and DMF (100mL) solution, dripping over 1h. After dropping, keep warm at 40-50°C for 3 hours. The reaction solution was poured into ice water (1000 mL), stirred for 30 min, filtered and washed with water. The obtained crude product was recrystallized by ethanol-water system to obtain pure compound 9 (60.7 g, 0.439 mol), with a yield of 43.9%.

Embodiment 2

[0068] Malononitrile (66.1g, 1.0mol), sulfur (32.0g, 1.0mol), triethylamine (10.1g, 0.1mol) and THF (200mL) were placed in a 1000mL reaction flask, and propionaldehyde ( 61.0g, 1.05mol) and THF (100mL) solution, dripping over 1h. After dropping, keep warm at 40-50°C for 3 hours. The reaction solution was poured into ice water (1000 mL), stirred for 30 min, filtered and washed with water. The obtained crude product was recrystallized from ethanol-water system to obtain pure compound 9 (55.4 g, 0.401 mol), with a yield of 40.1%.

Embodiment 3

[0070] Malononitrile (66.1g, 1.0mol), sulfur (32.0g, 1.0mol), triethylamine (10.1g, 0.1mol) and DMSO (200mL) were placed in a 1000mL reaction flask, and propionaldehyde ( 61.0g, 1.05mol) and DMSO (100mL) solution, dripping over 1h. After dropping, keep warm at 40-50°C for 3 hours. The reaction solution was poured into ice water (1000 mL), stirred for 30 min, filtered and washed with water. The obtained crude product was recrystallized from ethanol-water system to obtain pure compound 9 (52.0 g, 0.376 mol), with a yield of 37.6%.

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Abstract

The invention relates to a preparation method of an antipsychotic drug olanzapine. The method comprises three steps: first, using sulfur, propionaldehyde and malononitrile as raw materials, triethylamine as a catalyst to carry out ringclosure to obtain 5-methyl-2-amino-3-cyanothiophene; second, the 5-methyl-2-amino-3-cyanothiophene and o-fluoronitrobenzene generating 5-methyl-2-(2- nitrophenylamino)-3-cyanothiophene under effects of sodium hydride; third, the 5-methyl-2-(2- nitrophenylamino)-3-cyanothiophene reacting with hydrazine hydrate and N-methyl piperazine to carry out ringclosure reaction under existence of ferric trichloride / active carbon catalyst; so as to generate objective compound olanzapine through a one-pot method. The invention has the advantages of cheap and easily available raw materials, few steps, and simple process. A one-pot reaction is carried out in the third step, so that intermediate state compounds during the reaction process do not need to be separated or removed and can converse into the objective compound, and the high-purity olanzapine can be obtained with high yield. The whole process is suitable for industrial mass production with high product yield, low costs and convenient post-treatment.

Description

technical field [0001] The present invention relates to a new method for preparing antipsychotic olanzapine, specifically a method for preparing 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2, A new approach to 3-b][1,5]benzodiazepines. Background technique [0002] The chemical name of Olanzapine (hereinafter referred to as compound 1) is 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5] Benzodiazepine, the English name is 2-Methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine. The molecular structural formula of compound 1 is as follows: [0003] Compound 1 [0004] Olanzapine, also known as Olanzapine, whose trade name is Zyprexa, belongs to benzodiazepines and is an atypical antipsychotic drug. Olanzapine was developed by the Lilly Company of the United States. It was first launched in the United States in October 1996, and in the United Kingdom in April 1997. It has been listed in most developed countries at present, and my country app...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04
Inventor 顾华平鲍继胜
Owner 宁波人健化学制药有限公司
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