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Synthesis method of bambuterol hydrochloride impurity D

A technology of bambuterol hydrochloride and its synthesis method, which is applied in the field of organic chemical synthesis, can solve the problems of less impurity D in bambuterol hydrochloride, etc., and achieve the effect of easy-to-obtain raw materials, easy operation, and short steps

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 D

Method used

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  • Synthesis method of bambuterol hydrochloride impurity D
  • Synthesis method of bambuterol hydrochloride impurity D
  • Synthesis method of bambuterol hydrochloride impurity D

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-1

[0044] Dissolve 25 g of the compound of formula 1 [1-(3,5-dihydroxyphenyl)ethanone] in 200 ml of ethyl acetate, add 90 g of potassium carbonate and 10 ml of pyridine. Weigh 47 g of N,N-dimethylcarbamoyl chloride and dissolve it in 60 ml of ethyl acetate, and slowly drop it into the reaction system at room temperature. After the dropwise addition was completed, the mixture was stirred overnight at room temperature. Add 200 ml of purified water and stir well for 1 hour, separate liquid extraction, extract the aqueous phase with ethyl acetate (100 ml*2), combine the organic phases, and wash with 200 ml of 2% H 2 SO 4 Wash once with aqueous solution, once with 200 ml of saturated brine, dry over anhydrous sodium sulfate for 2 hours, filter, concentrate under reduced pressure to remove ethyl acetate, and obtain the compound of formula 2 [5-acetyl-1,3-phenylene- Bis(N,N-dimethylcarbamate)] 42 g, yield: 86.9%, purity: 98%.

[0045] The characterization data of the compound of gain...

Embodiment 2

[0050] Example 2 Synthesis and preparation of bambuterol hydrochloride impurity D[5-(1-hydroxyethyl)-1,3-phenylene-bis(N,N-dimethylcarbamate)]

Embodiment 2-1

[0052] Take 3.5 grams of formula 2 compound [5-acetyl-1,3-phenylene-bis(N,N-dimethylcarbamate)] and dissolve it in 35 milliliters of anhydrous methanol, and reduce the temperature of the reaction system to 0- 5°C, then 1.45 g of NaBH 4 Add to the above solution several times. Stir at room temperature (25-30° C.) for 2 hours, concentrate to dryness under reduced pressure, add 80 ml of ethyl acetate and 50 ml of purified water, and separate and extract. The aqueous phase was extracted with ethyl acetate (50 ml*2), washed with water (100 ml*2), washed with saturated brine (100 ml), dried over anhydrous sodium sulfate for 2 hours, filtered, and washed with an appropriate amount of ethyl acetate, and the Concentrate under reduced pressure to obtain 3.1 grams of bambuterol hydrochloride impurity D[5-(1-hydroxyethyl)1,3-phenylene-bis(N,N-dimethylcarbamate)], yield: 88.0 %, the purity is 99%.

[0053] The characterization data of bambuterol hydrochloride impurity D[5-(1-hydroxyethy...

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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 D. The synthesis method of the bambuterol hydrochloride impurity D does not disclose a literature report yet, so the synthesis method of the bambuterol hydrochloride impurity D 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 impurity D of bambuterol hydrochloride. 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-t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C269/00C07C269/06C07C271/44
Inventor 程宜兴张娟朱金龙朱毅杨鑫杰
Owner 上海宏冠医药科技有限公司
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