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Synthesis method of bambuterol hydrochloride impurity B

A technology of bambuterol hydrochloride and a synthesis method, applied in the field of organic chemical synthesis, can solve problems such as less bambuterol hydrochloride impurity B and the like, and achieve the effects of easy availability of raw materials, short steps and easy operation

Inactive Publication Date: 2017-12-08
上海宏冠医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] At present, in the prior art, there is less a kind of synthetic method specially for bambuterol hydrochloride impurity B

Method used

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  • Synthesis method of bambuterol hydrochloride impurity B
  • Synthesis method of bambuterol hydrochloride impurity B
  • Synthesis method of bambuterol hydrochloride impurity B

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-1

[0052] 5.0 grams of formula 1 compound [5-(2-bromoacetyl)-1,3-phenylene-bis(N,N-dimethylcarbamate)] was dissolved in 150 milliliters of anhydrous methanol, and the system Temperature down to 0-5°C, 1.0 g NaBH 4Add to the above solution several times. After the addition, the system is raised to normal temperature (25-30°C) and stirred for 2 hours. After concentrating to dryness under reduced pressure, add 50 ml of water to dissolve, extract 3 times with ethyl acetate (50 ml*3), wash 2 times with water (100 ml*2), wash 2 times with saturated brine (100 ml*2), no Dry over sodium sulfate for 2 hours, filter, wash with an appropriate amount of ethyl acetate, and concentrate under reduced pressure to obtain the compound of formula 2 [5-(2-bromo-1-hydroxyethyl)-1,3-phenylene-bis(N , N-dimethylcarbamate)] 4.1 g, yield 81.6%, purity 95%.

[0053] After confirmation and characterization using existing technologies, the obtained compound of formula 2 is 5-(2-bromo-1-hydroxyethyl)-1,3-p...

Embodiment 2-1

[0059] 4.1 grams of formula 2 compound [5-(2-bromo-1-hydroxyethyl)-1,3-phenylene-bis(N,N-dimethylcarbamate)] was dissolved in 120 milliliters of absolute ethanol , add 2 mol / L sodium hydroxide aqueous solution to the above reaction system, stir at room temperature (25-30° C.) for 15-20 minutes, and concentrate absolute ethanol under reduced pressure. After concentration to dryness, 50 ml of ethyl acetate and 40 ml of purified water were separated and extracted, and the aqueous phase was extracted once with 50 ml of ethyl acetate. The organic phases were combined, washed with water (100 ml), washed with saturated brine (100 ml), dried over anhydrous sodium sulfate for 2 hours, filtered, washed with an appropriate amount of ethyl acetate, and concentrated under reduced pressure to obtain the compound of formula 3 [5-(2-ring Oxyethyl)-1,3-phenylene-bis(N,N-dimethylcarbamate)] 2.9 g, yield: 90.2%, purity: 93%.

[0060] After confirmation and characterization using existing techno...

Embodiment 3

[0064] Example 3 Synthesis and preparation of bambuterol hydrochloride impurity B[5-(1,2-dihydroxyethyl)-1,3-phenylene-bis(N,N-dimethylcarbamate)]

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Abstract

The invention relates to the field of organic chemical synthesis, in particular to a synthesis method of a bambuterol hydrochloride impurity B. The synthesis method of the bambuterol hydrochloride impurity B does not disclose a literature report yet, so the synthesis method of the bambuterol hydrochloride impurity B has important commercial value. The process has the characteristics of being high in raw material availability, short in steps, easy to operate and the like.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, in particular to a method for synthesizing bambuterol hydrochloride impurity B. Background technique [0002] Bambuterol hydrochloride is an ultra-long-acting bronchodilator, belonging to the third generation 2 , an adrenergic receptor agonist, is the biscarbamate prodrug of terbutaline. The drug is hydrolyzed and oxidized into terbutaline in the body to exert its drug effect, and its first-pass metabolism is significantly smaller than that of terbutaline , The absorption is not affected by food, and the effective effect lasts up to 24 hours. Moreover, the side effect is small, the administration is convenient, and it has great medical value for asthma patients who are prone to attack or aggravate at night or in the morning, so it is considered as an ideal anti-asthma drug. [0003] The chemical name of Bambuterol Hydrochloride is 1-[bis-(3',5'-N,N-dimethylcarbamoyloxy)phenyl]-2-N-tert...

Claims

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Application Information

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IPC IPC(8): C07C269/06C07C271/44C07D303/16C07D301/28
Inventor 张娟朱毅程宜兴朱金龙杨鑫杰
Owner 上海宏冠医药科技有限公司
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