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Method for synthesizing mirabegron

A synthesis method and solvent technology, applied in the field of chemical drug synthesis, can solve the problems of non-scale-up production, complex post-processing, unfriendly environment, etc., and achieve the effect of convenient post-processing, fewer reaction steps, and environmental friendliness

Inactive Publication Date: 2014-07-02
HEILONGJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The purpose of the present invention is to provide a synthetic method for mirabegron in order to solve the problems of unfriendly environment, many reaction steps, low yield, complicated post-treatment and incapable of scale-up production in the existing mirabegron synthetic method

Method used

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  • Method for synthesizing mirabegron
  • Method for synthesizing mirabegron
  • Method for synthesizing mirabegron

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specific Embodiment approach 1

[0025] Specific embodiment one: the synthetic method of Mirabegron of the present embodiment, carry out according to the following steps:

[0026] 1. Add nitrophenylethylamine and (R)-styrene oxide into the solvent according to the molar ratio of 1:(1.0~1.5), and carry out the ring-opening reaction at 60°C~70°C. After the reaction is completed, Then recrystallize with a recrystallization solvent to obtain (R)-2-((4-nitrophenethyl)amino)-1-phenethyl-1-alcohol;

[0027] Two, the (R)-2-(4-nitrophenethyl) amino)-1-phenethyl-1-alcohol obtained in step 1 is added in the solvent, and then according to the catalyst and (R)-2-(( The molar ratio of 4-nitrophenethyl)amino)-1-phenethyl-1-alcohol is (0.01~0.05): 1, add the catalyst, carry out the reduction reaction at room temperature and hydrogen atmosphere, and wait for the reaction to complete Afterwards, the solvent is evaporated under reduced pressure to obtain (R)-2-((4-aminophenyl)amino)-1-phenethyl-1-alcohol; wherein the solvent i...

specific Embodiment approach 2

[0032] Embodiment 2: The difference between this embodiment and Embodiment 1 is that the solvent described in step 1 is isopropanol, ethyl acetate, dichloromethane, tetrahydrofuran or acetonitrile. Others are the same as in the first embodiment.

specific Embodiment approach 3

[0033] Embodiment 3: The difference between this embodiment and Embodiment 1 or 2 is that the ring-opening reaction is carried out at 60° C. to 65° C. in step 1. Others are the same as in the first or second embodiment.

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Abstract

The invention discloses a method for synthesizing mirabegron, relates to a method for preparing mirabegron, and aims at solving the problems that the existing method for synthesizing the mirabegron is not friendly to environment, more in reaction steps, low in yield, and complicated in post-treatment, and cannot be amplified to produce. The method disclosed by the invention comprises the following steps: 1, carrying out ring-opening reaction by taking p-nitrophenylethylamine and (R)-phenylethylene oxide as initial raw materials; 2, carrying out reduction reaction; 3 carrying out condensation reaction. The method disclosed by the invention is cheap and available in selected raw materials, high in yield, low in cost, friendly to environment and applicable to industrial amplifying production. The method is applied to synthesis of the mirabegron.

Description

technical field [0001] The invention relates to a preparation method of mirabegron, which belongs to the technical field of chemical drug synthesis. Background technique [0002] Mirabegron (Mirabegron), a β3 adrenergic receptor agonist developed by Japan Astellas Pharmaceuticals, is used to treat overactive bladder, and it was launched and sold in Japan on September 16, 2011. On March 28, it was approved by the US Food and Drug Administration (FDA) for the treatment of overactive bladder (OAB) in adults. [0003] Mirabegron: C 21 h 24 N 4 o 2 S, the Chinese chemical name is: (R)-2-(2-amino-1,3-thiazol-4-yl)-4'-[2-[(2-hydroxy-2-phenylethyl)amino]ethyl Base] phenylacetamide. [0004] The preparation method of Mirabegron mainly contains following two kinds: [0005] Method 1 (Maruyama T, Suzuki T, Onda K, et al. Amide derivatives or salts thereof: U.S., 6346532[P]. 2002-2-12.) The synthetic route is as follows: [0006] [0007] This synthetic route mainly uses p-ni...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/40
CPCC07D277/40
Inventor 张华李杨陈仕杰沈明辉王雪微
Owner HEILONGJIANG UNIV
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