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Terbutaline derivative D as well as preparation method and application thereof

A technology for terbutaline derivatives, applied in the field of terbutaline derivative D and its preparation, capable of solving the problems of not providing the use of terbutaline derivatives

Pending Publication Date: 2022-05-27
HARVEST PHARMA HUNAN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This patent provides a variety of synthesis methods of terbutaline derivatives, but does not provide the use of terbutaline derivatives, which has certain limitations

Method used

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  • Terbutaline derivative D as well as preparation method and application thereof
  • Terbutaline derivative D as well as preparation method and application thereof
  • Terbutaline derivative D as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Take a 250ml three-necked flask, add 9.8g of 3,5-dimethoxyphenylacetic acid, 7.3g of tert-butylamine, 50g of dichloromethane, 6.7g of HOBT, and 11.5g of EDCI, react at room temperature, and monitor by HPLC until the reaction is complete. The reaction was added dropwise to 100 g of water, extracted with dichloromethane, the organic layer was washed with water until neutral, allowed to stand for separation, and the organic phase was concentrated under reduced pressure to obtain about 13 g of Intermediate 1 with a liquid phase purity of 98.0%.

Embodiment 2

[0036] Take a 250ml three-necked flask, dissolve the above-mentioned intermediate 1 with 13g of tetrahydrofuran, dropwise add a solution of borane in tetrahydrofuran (150ml, 1.0M), stir for 15 minutes after the dropwise addition, and then reflux for reaction until the reaction is complete. Then 20 g of methanol was added to continue refluxing for 8 h, and the solvent was removed under reduced pressure. 50 g of ethyl acetate and 100 g of water were added to the residue, then 2 ml of concentrated hydrochloric acid was added to adjust the pH to 3, the mixture was left to stand for separation, and the organic layer was discarded. Add 50 g of ethyl acetate to the aqueous layer, adjust the pH to 7.5-8.5 with sodium hydroxide, stand for separation, discard the aqueous layer, and wash the organic layer with water until neutral. The organic phase was concentrated under reduced pressure to obtain Intermediate 2 with a purity of 95.0%.

Embodiment 3

[0038] Take a 250ml three-necked flask, add Intermediate 2 and 60g of dichloromethane, cool to below 0°C, add 25g of boron tribromide dropwise, stir for 15 minutes after the dropwise addition, and then stir for 3h below 0°C until the reaction is complete. The reaction solution was poured into 100 g of ice water, left to stand for separation, and the organic layer was discarded. Add 50 g of ethyl acetate to the aqueous layer, adjust the pH to 7.5-8.5 with sodium hydroxide, stand for separation, discard the aqueous layer, and wash the organic layer with water until neutral. The organic phase was concentrated under reduced pressure to obtain intermediate 3 with a purity of 97.0%.

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PUM

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Abstract

The invention discloses a terbutaline derivative D and a synthesis method thereof, the structure of the terbutaline derivative D is as shown in a structural formula (I), and the specific synthesis route is as follows: 3, 5-dimethoxyphenylacetic acid and tert-butylamine are taken as raw materials, and the terbutaline derivative D is obtained through condensation, reduction, deprotection and substitution reaction. The terbutaline derivative D disclosed by the invention is simple in synthesis method, an intermediate generated in the synthesis process can be used as a terbutaline impurity, and a final product can be used as a bambuterol impurity for quality research.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular, the invention relates to a terbutaline derivative D and a preparation method and application thereof. Background technique [0002] Terbutaline, chemically named 5-(1-hydroxy-2-tert-butylaminoethyl)benzene-1,3-diol, is an epinephrine beta 2 Receptor agonists that increase mucociliary cleansing function, which is reduced due to obstructive pulmonary disease, thereby accelerating the clearance of mucus secretions. It is clinically suitable for bronchial asthma, chronic bronchitis, emphysema and other lung diseases with bronchospasm. [0003] [0004] Bambuterol, a prodrug of terbutaline, can be metabolized into terbutaline in the body, thereby relaxing bronchial smooth muscle, has anti-asthmatic effect, and also has the effect of inhibiting the release of inflammatory mediators by mast cells. It can be used clinically to treat asthma, emphysema, bronchitis, etc. [0005] ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C271/44C07C269/06C07C215/52
CPCC07C271/44C07C215/52Y02P20/55
Inventor 李海龙陈永刘芳洁陈蓉
Owner HARVEST PHARMA HUNAN CO LTD
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