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Method for preparing high purity dimemorfan and phosphate

A dimethorphan, high-purity technology, applied in respiratory system diseases, organic chemistry, drug combination and other directions, can solve the problems such as the unseen dimethorphan intermediate 5 and phosphate-related literature and patent reports, etc.

Inactive Publication Date: 2010-06-30
北京利乐生制药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Through searching, there are no relevant literature and patent reports on the preparation of high-purity dimerphane intermediate 5 and phosphate by recrystallization

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] After splitting 51.8g of tartrate, add 28% ammonia water to pH = 9, extract three times with ethyl acetate, combine the organic phases, wash three times with water, and remove the solvent by rotary evaporation to obtain a white water-containing oil, add 30mL of absolute ethanol, Evaporate at 70°C until no water flows out, and the liquid is 30.51g. Add 130Ml of 85% phosphoric acid, heat with electromagnetic stirring at 135-140°C, react for 70h, transfer the reaction mixture into ice water, add ammonia water to make it alkaline, extract with ether three times, wash with water and remove the solvent under reduced pressure to obtain yellow to brown yellow Oily matter, 29.28g, was added with acetone 10ml, oscillated to obtain a homogeneous liquid, put into the refrigerator to crystallize (overnight) to obtain light yellow crystals, the above-mentioned crystals were taken for liquid chromatography, the peak area percentage was 99.5%, and the solid was recrystallized with aceto...

Embodiment 2

[0016] After splitting 134.52g of tartrate, add 28% ammonia water to pH = 9, extract three times with ethyl acetate, combine the organic phases, wash three times with water, and remove the solvent by rotary evaporation to obtain a white water-containing oil, add 80mL of absolute ethanol, Evaporate at 70°C until no water flows out, and the liquid is 78.51g. Add 380Ml of 85% phosphoric acid, heat with electromagnetic stirring at 135-140°C, react for 70h, transfer the reaction mixture into ice water, add ammonia water to make it alkaline, extract with ether three times, wash with water and remove the solvent under reduced pressure to obtain yellow to brown yellow Oil, 76.28g, added acetone 30ml, oscillated to obtain a homogeneous liquid, put into the refrigerator to crystallize (overnight) to obtain pale yellow crystals, took the above crystals for liquid chromatography, the peak area percentage was 99.46%, and recrystallized the solid with acetone to obtain The percentage of col...

Embodiment 3

[0018] After splitting 48.8g of tartrate, add 28% ammonia water to PH = 9, extract three times with ethyl acetate, combine the organic phases, wash three times with water, and remove the solvent by rotary evaporation to obtain a white water-containing oil, add 30mL of absolute ethanol, Evaporate at 70°C until no water flows out, and the liquid is 28.51g. Add 130Ml of 85% phosphoric acid, heat with electromagnetic stirring at 135-140°C, react for 70h, transfer the reaction mixture into ice water, add ammonia water to make it alkaline, extract with ether three times, wash with water and remove the solvent under reduced pressure to obtain yellow to brown yellow Oily matter, 29.28g, was added with acetone 10ml, oscillated to obtain a homogeneous liquid, put into the refrigerator to crystallize (overnight) to obtain light yellow crystals, the above-mentioned crystals were taken for liquid chromatography, the peak area percentage was 99.58%, and the solid was recrystallized with acet...

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PUM

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Abstract

The invention discloses a method for preparing high-purity dimemorfan and phosphate, relating to a new method for preparing and purifying raw material dimemorfan of an antitussive drug and a relative intermediate. The invention aims to avoid high vacuum degree distillation operation in the preparation of an US3786054 step five intermediate (2-(p-methylbenzyl)-octahydro isoquinolined-(+)tartrate) so as to avoid the disadvantage that individual impurity can not be removed through column separation. The step five intermediate with high purity and high yield is obtained by using acetone and the like as solvents to recrystallize cyclized reaction mixture.

Description

technical field [0001] The invention relates to the preparation of a non-addictive central antitussive drug-dimethorphan raw material and intermediates. Background technique [0002] Cough is a frequently-occurring and common disease. Except for seasonal outbreaks and influenza, diseases such as bronchitis and chronic bronchitis all take cough as the main clinical symptom. In my country, the incidence rate of chronic bronchitis in middle-aged and elderly people over 50 years old is about 15%-30%. Due to environmental pollution, there are 400,000 new chronic bronchitis patients every year. Whether domestic or foreign, cough patients occupy a huge base, and there will always be a huge market demand for effective antitussives. Global over-the-counter (OTC) cold and cough medicines account for the largest market sales, reaching 21.3%. [0003] The mechanism of coughing is a neuroprotective reflex produced when the respiratory mucosa is irritated. The respiratory mucosa trans...

Claims

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Application Information

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IPC IPC(8): C07D221/28A61P11/14
Inventor 李学坤
Owner 北京利乐生制药科技有限公司
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