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Method for synthesizing terbutaline

A technology of terbutaline and compound, applied in the field of synthesizing terbutaline, can solve the problems of carcinogenicity and residue

Pending Publication Date: 2020-01-31
SUZHOU HOMESUN PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] During the synthesis process of this route, intermediate II-1 (α-bromo-3,5-dibenzyloxyacetophenone) will be produced. This structure is clearly considered by the FDA as a genotoxic impurity containing a warning structure, and there will be Obvious carcinogenic effect, because the intermediate is produced during the synthesis process, so there will inevitably be residues in the final product, resulting in the risk of clinical use of the raw material synthesized by this synthesis route

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  • Method for synthesizing terbutaline
  • Method for synthesizing terbutaline

Examples

Experimental program
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Embodiment 1

[0035] (1) Preparation of compound II:

[0036] Add 40g of compound I to a 200mL reaction flask, then add 100mL of tetrahydrofuran, add 10g of selenium dioxide at room temperature, and react at room temperature for 24 hours. After the reaction is completed, the reaction solution is filtered, and the filtrate is washed with saturated saline and used directly for the next reaction.

[0037] (2) Preparation of compound III:

[0038] Add the treatment solution obtained in step (1) into a 200mL reaction bottle, raise the temperature to 40-45°C, add dropwise a tetrahydrofuran solution of 0.4g / mL tert-butylamine (12g tert-butylamine dissolved in 30mL tetrahydrofuran), and add dropwise for about 30 minutes After the dropwise reaction, continue the heat preservation reaction for 2 hours. After the reaction, control the temperature at 40-45° C. to evaporate the solvent under reduced pressure, add 80 mL of methanol to the distillation residue, and stir for 30 minutes to completely dissol...

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Abstract

The invention discloses a method for synthesizing terbutaline. The method comprises the following steps: reacting a compound I with selenium dioxide to obtain a compound II; reacting the compound II with tert-butylamine to obtain a compound III; reacting the compound III with a reducing agent to obtain a compound IV; and reacting the compound IV with a catalyst to remove benzyloxy to obtain terbutaline. The synthesis method has the advantage that the generation of impurity alpha-bromo-3, 5-dibenzyloxyacetophenone is avoided.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a method for synthesizing terbutaline. Background technique [0002] Terbutaline, chemical name: 5-(1-hydroxy-2-tert-butylaminoethyl) benzene-1,3-diol, clinically used for the treatment of bronchial asthma, asthmatic bronchitis, emphysema, etc. drug. This product is a β2-receptor stimulant with bronchodilator effect. It is highly selective to bronchial smooth muscle, has little excitatory effect on the heart, and has no central effect. For bronchial asthma, asthmatic bronchitis, obstructive emphysema and other lung diseases with bronchospasm. It is especially suitable for asthma patients with cardiovascular diseases such as hypertension and coronary heart disease. [0003] The existing terbutaline conventional production synthetic route is as follows: [0004] [0005] During the synthesis process of this route, intermediate II-1 (α-bromo-3,5-dibenzyloxyacetophenone) wil...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/00C07C215/30
CPCC07C213/00C07C213/02C07C249/02C07C45/28C07C215/30C07C217/66C07C251/16C07C49/86Y02P20/55
Inventor 樊超陆红彬杨磊
Owner SUZHOU HOMESUN PHARMA
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