Method for preparing anti-asthmatic medicament of salmeterol

A drug and asthma technology, which is applied in the field of preparation of the anti-asthma drug salmeterol, can solve the problems of cumbersome preparation method, unsatisfactory yield, and high difficulty in industrialization, and achieve convenient experimental operation, novel synthetic route and low production cost. low effect

Inactive Publication Date: 2010-05-26
ZHEJIANG WANLI UNIV
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0007] However, this preparation method has the disadvantages of complicated operation and unsatisfactory yield.
[0008] In the "Synthesis of New Asthma Drug Mexaterol" published in the Journal of East China Normal University (September 2

Method used

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  • Method for preparing anti-asthmatic medicament of salmeterol
  • Method for preparing anti-asthmatic medicament of salmeterol
  • Method for preparing anti-asthmatic medicament of salmeterol

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Embodiment

[0022] The specific preparation steps of the present invention's synthetic Mexaterol are as follows: (1) Synthesis of 3-hydroxymethyl-4-hydroxyl-phenylacrylic acid (2): add 200ml p-xylene in a 500ml single-necked round-bottomed flask, then add 32.8 Gram (0.2mol) of p-hydroxyphenylacrylic acid, 50ml of formaldehyde, 25 grams of boric acid (0.4mol), then heated to 150°C and refluxed for 12h; then cooled to room temperature to precipitate a large amount of yellow precipitate, filtered, the obtained precipitate was washed with an appropriate amount of water, and then dried to obtain The product 3-hydroxymethyl-4-hydroxy-phenylacrylic acid was 28.2 grams, the yield was 80%, and the melting point (mp): 185.1-185.7°C.

[0023] (2) Synthesis of 3-hydroxymethyl-4-hydroxyl-(b-hydroxyl)-phenylpropanal (3): add 19.4 grams (0.1mol) of 3- Hydroxymethyl-4-hydroxy-phenylacrylic acid, 50ml of 30% fresh hydrogen peroxide (0.4mol), 0.2g of lipase and 150ml of ethyl acetate as a reaction solvent,...

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Abstract

The invention discloses a method for preparing an anti-asthmatic medicament of salmeterol. The method comprises the following steps of: adding paraxylene, parahydroxyphenylacrylic acid, formaldehyde and acid medium into a reactor, heating, cooling, filtering, washing and drying to obtain 3-hydroxymethyl-4-hydroxyl-phenylacrylic acid; adding the 3-hydroxymethyl-4-hydroxyl-phenylacrylic acid into the reactor, then adding oxyful, lipase and ethyl acetate to finally obtain 3-hydroxymethyl-4-hydroxyl-(beta-hydroxy)-phenylpropyl aldehyde, adding the 3-hydroxymethyl-4-hydroxyl-(beta-hydroxy)-phenylpropyl aldehyde and 6-(4-phenylbutoxy)hexylamine into the reactor, heating for reflowing, cooling, filtering, adding sodium borohydride in batches into filtrate, stirring at normal temperature, then evaporating to dryness, extracting, combining organic layers, drying, filtering and evaporating to dryness to obtain a solid, and separating by using the column chromatography to obtain the final product. The invention has novel and short synthetic route, convenient experiment operation, higher yield of the target product and lower production cost.

Description

technical field [0001] The invention relates to the technical field of preparation methods of anti-asthma drugs, in particular to a preparation method of the anti-asthma drug salmeterol. Background technique [0002] Salmeterol (Salmeterol), chemical name: 2-(hydroxymethyl)-4-[1-hydroxy-2-[6-(4-phenylbutoxy)hexylamino]ethyl]-phenol, about Salmeterol abroad The synthesis of terol (Salmeterol) has been reported, as described in WO03074458, the synthetic route of salmeterol is as follows: [0003] [0004] Although the synthesis route of salmeterol reported above is short, there are problems such as relatively difficult to obtain reaction raw materials, relatively harsh reaction conditions, and low overall yield. [0005] Another example is that French patent FR2545482 also discloses a preparation method of salmeterol, and its main synthetic route is as follows: [0006] [0007] However, this preparation method has disadvantages such as complicated operation and unsati...

Claims

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Application Information

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IPC IPC(8): C07C217/10C07C213/08
Inventor 应敏张晓敏张华星
Owner ZHEJIANG WANLI UNIV
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