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Namenda synthesis method

A technology of memantine hydrochloride and its synthetic method, which is applied in the field of synthesis of memantine hydrochloride, can solve the problems of chloroform harmful to human body, low boiling point of ether, volatilization of ether, etc., and achieve the effect of reducing production cost

Inactive Publication Date: 2004-11-10
中国人民解放军北京军医学院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] This method has the following disadvantages: benzene, which is harmful to the environment and human body, is used as the extraction solvent in the post-treatment process of the two-step operation of acetylamidation and alcoholysis; and diethylene glycol, which is relatively expensive, is used in the alcoholysis process. As a proton donor; ethanol / ether mixed solvent is used in the recrystallization process. Since ether has a very low boiling point, high volatility, and difficult condensation of steam, a large amount of ether will be volatilized during the process of adding ether to ethanol in a reflux state. Great loss and easy to cause fire and explosion accidents
[0006] Although this method replaces ether with chloroform, chloroform is still a harmful solvent to the human body; in addition, the acetamido reaction of this method still uses expensive, toxic acetonitrile and sulfuric acid as reaction reagents, using these reagents naturally Potential danger of personal injury

Method used

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  • Namenda synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Weigh 100g of bromodimethyladamantane and 20g of urea respectively, mix the bromodimethyladamantane and urea evenly, heat and melt until the temperature is 180°C, and the internal temperature reaches 180-240°C; after 4 hours of reaction, cool down naturally , add concentrated hydrochloric acid to dissolve the reactants completely; transfer to a beaker, add NaOH to adjust the pH to 7.0, steam distillation; filter and dry to obtain dimethylamantadine.

[0040] Add dimethylamantadine, distilled water, and activated carbon into the flask; adjust the pH to 1.1 with hydrochloric acid, heat to 70°C to dissolve and decolorize for 0.5 hours, and cool to room temperature; filter, and evaporate the filtrate to dryness under reduced pressure to obtain a white solid, which is washed with acetone until The pH was 5.0, and the filter was dried; the filter cake was vacuum-dried at 75° C. to obtain memantine hydrochloride with a total yield of 56.2%.

Embodiment 2

[0042] Weigh 100g of bromodimethyladamantane and 200g of urea respectively, mix the bromodimethyladamantane and urea evenly, heat and melt until the temperature is 160°C, and the internal temperature reaches 180-240°C; after reacting for 4.5 hours, cool down naturally , add concentrated hydrochloric acid to completely dissolve the reactants; transfer to a beaker, add NaOH to adjust the pH to 8.0, steam distillation; filter and dry to obtain dimethylamantadine.

[0043] Add dimethylamantadine, distilled water, and activated carbon into the flask; adjust the pH to 3.0 with hydrochloric acid, heat to 72°C to dissolve and decolorize for 1 hour, and cool to room temperature; filter, and evaporate the filtrate to dryness under reduced pressure to obtain a white solid, which is washed with acetone until The pH was 4.0, filtered and dried; the filter cake was dried in an oven at 75° C. to obtain memantine hydrochloride with a total yield of 52.5%.

Embodiment 3

[0045] Weigh 100g of bromodimethyladamantane and 100g of urea respectively, mix bromodimethyladamantane and urea evenly, heat and melt until the temperature is 140°C, and the internal temperature reaches 180-240°C; cool down naturally after 4 hours of reaction , add concentrated hydrochloric acid to dissolve the reactants completely; transfer to a beaker, add NaOH to adjust the pH to 13.9, steam distillation; filter and dry to obtain dimethylamantadine.

[0046] Add dimethylamantadine, distilled water, and activated carbon into the flask; adjust the pH to 6.0 with hydrochloric acid, heat to 71°C to dissolve and decolorize for 1 hour, and cool to room temperature; filter, and evaporate the filtrate to dryness under reduced pressure to obtain a white solid, which is washed with ethanol until The pH was 6.0, and the filter was dried; the filter cake was vacuum-dried at 65° C. to obtain memantine hydrochloride with a total yield of 51.3%.

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Abstract

A process for synthesizing Memantine characterized in that, the Memantine is prepared from bromization dimethyl Amantadine through amination reaction with carbamide and acidification reaction with chlorhydric acid.

Description

technical field [0001] The invention relates to a method for synthesizing memantine hydrochloride which can be used as a drug for treating dementia and an N-methyl-D-aspartic acid (NMDA) receptor antagonist. Background technique [0002] The chemical name of memantine hydrochloride is 3,5-dimethyltricyclo[3.3.1.13,7]decane-1-amine hydrochloride, which is a drug developed by German Merz company for the treatment of dementia and has been approved in Germany It is marketed and used, and has completed phase III clinical research in the United States and other countries. Memantine hydrochloride is a non-competitive, medium-strength and fast voltage-gated NMDA receptor antagonist, which can block the overload of intracellular calcium and inhibit the excitotoxicity of excitatory amino acids. Clinical studies have confirmed its effect on vascular dementia, Alzheimer's Both silent dementia and AIDS dementia have good curative effects, so they have great potential for economic and so...

Claims

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Application Information

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IPC IPC(8): C07C209/00C07C209/06C07C211/38
Inventor 钟武方勇颜晓林赵奎君陈瑶
Owner 中国人民解放军北京军医学院
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