Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Synthesis method of Mirabegron

A synthetic method, aminomethyl technology, applied in the direction of organic chemistry, etc., can solve the problems of low mirabegron yield, high processing cost, and human health hazards, and achieve a green and environmentally friendly reaction process with fewer reaction steps and good The effect of market competitiveness

Active Publication Date: 2020-03-06
SUZHOU UUGENE BIOPHARMA
View PDF5 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The yield of Mirabegron prepared by this method is low, and the steps are long. In the reaction step, borane dimethyl sulfide and high temperature and high pressure are used, wherein borane dimethyl sulfide is harmful to human health, and high temperature and high pressure are not only dangerous but also Processing costs will be high

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthesis method of Mirabegron
  • Synthesis method of Mirabegron
  • Synthesis method of Mirabegron

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] At room temperature, add methanol 300ml, R-2 (aminomethyl) benzyl alcohol 137 grams, 2-(2-aminothiazol-5-yl)-N-[4-(2-chloro-ethyl) -Phenyl]-acetamide 295g and 111g of triethylamine, heat the mixed solution to 60-65°C, stir and reflux for 8h, pump the reaction solution into 500g of water while it is hot, cool to 10-15°C, filter 380 g of off-white solid Mirabegron was obtained with a yield of 96% and a purity of 99.9%.

Embodiment 2

[0030] At room temperature, 300 ml of isopropanol, 137 grams of R-2 (aminomethyl) benzyl alcohol, 2-(2-aminothiazol-5-yl)-N-[4-(2-chloro-ethane base)-phenyl]-acetamide 295g and 111g of triethylamine, warm up the mixture to 60-65°C, stir and reflux for 8h, pump the reaction liquid into 500g of water while it is hot, and cool down to 10-15°C , and filtered to obtain 360g off-white solid mirabegron, with a yield of 91% and a purity of 99.47%.

Embodiment 3

[0032] At room temperature, add methanol 300ml, R-2 (aminomethyl) benzyl alcohol 137 grams, 2-(2-aminothiazol-5-yl)-N-[4-(2-chloro-ethyl) -Phenyl]-acetamide 295g and 141g of triethylamine, heat the mixture to 60-65°C, stir and reflux for 8h, pump the reaction liquid into 500g of water while it is hot, cool down to 10-15°C, filter 370 g of off-white solid mirabegron was obtained, with a yield of 94% and a purity of 98.3%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
wavelengthaaaaaaaaaa
Login to View More

Abstract

The invention discloses a synthesis method of Mirabegron. The synthesis method comprises the following processing steps of S1, under the room-temperature condition, adding R-2 (amino-N-methylbenzylamine) benzyl alcohol,2-(2-Aminothiazole-5-based)-N-[4-(2-Chloro-Ethyl)-Phenyl]-Acetamide and triethylamine to a solvent, and performing reflowing for 8h; S2, after the reaction is finished, pumping reaction liquid into water, and performing filtering to obtain the Mirabegron. In the step S1, the solvent is one or more of methanol, ethanol, propanol, dichloromethane, tri- chloromethane, acetone, butanone and toluene. An organic solvent which has stimulability is not used, a borane-methyl sulfide complex having high risk is not used, high temperature and high pressure are not adopted, the reactionprocess is green and environmental-friendly, clean production is realized, the cost is reduced, and the synthesis method has good market competitiveness.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a synthesis method of mirabegron. Background technique [0002] Mirabegron is used to treat overactive bladder in adults. The clinical trial data show that compared with the existing clinical treatment of adults with overactive bladder, mirabegron has the characteristics of rapid onset of action, good tolerance, no sexual dysfunction for patients, and small adverse reactions. Its chemical name is 2-amino-N-[4-[2-[[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-4-thiazoleacetamide, and its chemical formula is : [0003] [0004] There is a patent application (publication number: EP1440969,2004, A1) in the literature about the synthesis of Mirabegron in the prior art, and this patent application relates to the preparation method of Mirabegron, and the steps of the preparation method are as follows: a) in an organic solvent, Condensate D-mandelic acid ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/40
CPCC07D277/40
Inventor 高元崔槐杰宗杨磊
Owner SUZHOU UUGENE BIOPHARMA
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com