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Method for synthesizing drug pranlukast from tetrahydrofuran path

A technology for synthesizing drugs and tetrahydrofuran, applied in directions such as organic chemistry, can solve problems such as difficult industrialization, difficulty in tetrazolium, and no mention of synthetic methods, and achieve the effects of easy availability of raw materials, safe reaction, and simple reaction

Active Publication Date: 2009-06-10
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] This route does not mention the synthetic method of the raw materials used, and its improvement is only reflected in the synthesis of the tetrazole ring
[0017] ④Giles, Hideki, and Hayler all add substituents to tetrazole to make the condensation reaction easier, but it is difficult to synthesize tetrazole with substituents on nitrogen, and the final removal reaction uses dangerous lithium aluminum tetrahydrogen, etc. Reagent, not easy to industrialize
[0021] This route does not mention the synthetic method of raw material 4-(4-phenylbutoxy) benzonitrile, and the synthetic difficulty of 2-hydroxyl-3-iodoacetophenone is bigger simultaneously

Method used

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  • Method for synthesizing drug pranlukast from tetrahydrofuran path
  • Method for synthesizing drug pranlukast from tetrahydrofuran path
  • Method for synthesizing drug pranlukast from tetrahydrofuran path

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Embodiment 1

[0081] A method for synthesizing drug pranlukast from tetrahydrofuran approach, the synthetic route of the method is as follows:

[0082]

[0083] With reference to the process flow diagram shown in Figure 1, the above-mentioned synthetic method may further comprise the steps:

[0084] a. Synthesis of 4-chlorobutanol A

[0085] Add 144 g of THF and 200 g of concentrated hydrochloric acid into a three-neck flask, react at 60°C for 12 h, cool, extract with dichloromethane, remove the solvent, and distill under reduced pressure to obtain product A, namely 4-chlorobutanol.

[0086] b. Synthesis of 4-phenylbutanol B

[0087] Add 100ml of benzene and 44.3g of aluminum trichloride to the four-neck flask, add A30g dropwise at 12°C, and react for 7.5h. Pour into ice water, separate liquid, remove solvent, and distill under reduced pressure to obtain colorless transparent liquid B.

[0088] c. Synthesis of 1-bromo-4-phenylbutane C

[0089] Add 0.38g of B and 1.08g of 40% hydrobro...

Embodiment 2— Embodiment 5

[0117] The difference of embodiment 2-5 and embodiment 1 is only that the consumption of substance is different, the condition of reaction is different, as shown in the table; In addition, the amount of each step output substance is also different (not shown in the table) and each step Not all of the output was used in subsequent steps.

[0118] Other contents of the preparation methods of the above-mentioned embodiments are the same.

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Abstract

The invention discloses a new method for synthesizing pranlukast, in particular to a method for synthesizing medicinal pranlukast from tetrahydrofuran. The method takes the tetrahydrofuran as raw materials to prepare the pranlukast through ring opening, Friedel-Crafts alkylation, bromination, condensation and ring closing reactions. The method has the characteristics of readily available raw materials, simple reaction for preparation of an intermediate, high yield, safe reactions and suitability for industrial production, and can be used to prepare the medicinal pranlukast for treating asthma and allergic rhinitis.

Description

technical field [0001] The invention relates to a preparation method of leukotriene receptor antagonist prankast, which belongs to the field of compound preparation, in particular to a method for synthesizing prankast from tetrahydrofuran. Background technique [0002] Pranlukast is a leukotriene receptor antagonist developed by Japan Ono Company, and its chemical name is 4-oxo-8-[4-(4-phenylbutoxy)benzamide-2-tetraazole Azol-5-yl-4H-1-benzopyran. It was launched in Japan in June 1995, and it is mainly used for the treatment of asthma in clinical practice. It has also been used for the treatment of allergic rhinitis since November 1999. [0003] Pranlukast has a significant antagonism effect on tracheal smooth muscle spasm and lung strip contraction caused by leukotriene attack, effectively relieves airway stenosis and dyspnea, can significantly weaken the early and late bronchoconstriction responses stimulated by inhaled allergens, and Inhibition of allergen-induced enhan...

Claims

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Application Information

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IPC IPC(8): C07D407/04
Inventor 张越王永国王春芳
Owner HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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