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Preparation methods for mirabegron and intermediate thereof

A technology of intermediates and compounds, which is applied in the field of drug synthesis, can solve the problems of harsh reaction conditions, complicated operation, and high cost, and achieve the effects of mild reaction conditions, simple operation, and favorable industrial production

Inactive Publication Date: 2013-11-13
SHANGHAI INST OF PHARMA IND +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved by the present invention is that in order to overcome the defects of complex operation, high cost, harsh reaction conditions and unsuitability for large-scale industrial production in the existing method for preparing Mirabegron, a kind of Mirabegron is provided. The preparation method of its intermediate

Method used

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  • Preparation methods for mirabegron and intermediate thereof
  • Preparation methods for mirabegron and intermediate thereof
  • Preparation methods for mirabegron and intermediate thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] The preparation of embodiment 1 (R)-2-{N-benzyl-[2-(4-nitrophenyl) ethyl] amino}-1-phenylethanol [Ⅰ]

[0022] (R)-Styrene oxide (2.31g, 19.2mmol) and N-benzyl-4-nitrophenethylamine (3.28g, 12.8mmol) in 12ml of isopropanol were refluxed for 20h. The solvent was evaporated under reduced pressure, recrystallized from n-hexane / isopropyl ether, and dried to obtain 3.61 g of yellow solid I, with a yield of 75%. 1 H-NMR (CDCl 3 )δ: 1.28(1H,s) 2.69~2.98(6H,m), 3.57(1H,d,J=13.2Hz), 3.95(1H,d,J=13.2Hz), 4.67~4.69(1H,m) , 7.21~7.36 (12H, m), 8.10~8.12 (2H, m).

Embodiment 2

[0023] The preparation of embodiment 2 (R)-2-[(4-aminophenethyl) amino]-1-phenylethanol [Ⅱ]

[0024] Compound Ⅰ (3.0g, 8.0mmol), 10%Pd / C (0.15g) and methanol (25ml) were placed in a hydrogenation reactor, filled with 1MPa hydrogen, reacted at room temperature (10℃~30℃) for 30h, filtered, and the filtrate was concentrated , and dried to give Ⅱ (1.03g, yield 100%, HPLC purity 99.8%).

Embodiment 3

[0025] Preparation of Example 3 (R)-2-[(4-aminophenethyl)amino]-1-phenylethanol [Ⅱ]

[0026] Compound Ⅰ (3.0g, 8.0mmol), 10%Pd / C (0.03g) and methanol (25ml) were placed in a hydrogenation reactor, filled with 10MPa hydrogen, reacted at room temperature (10°C-30°C) for 30h, filtered, and the filtrate was concentrated , and dried to give Ⅱ (1.03g, yield 100%).

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Abstract

The invention discloses a preparation method for mirabegron. The preparation method comprises the following steps: 1, reducing a compound I in an alcoholic solvent in a hydrogen environment under the catalysis of palladium-carbon so as to obtain a compound II; and 2, mixing the compound II obtained in step 1 with 2-amino-4-thiazole acetic acid in water in an environment with a pH value of 1 to 7 under the action of a condensing agent and carrying out acylation so as to obtain mirabegron, wherein reaction temperature is 10 to 30 DEG C. The invention further discloses a preparation method for an intermediate II of mirabegron, and the preparation method comprises the step of reducing the compound I in the alcoholic solvent in the hydrogen environment under the catalysis of palladium-carbon so as to obtain the compound II. The preparation methods provided by the invention have the advantages of easiness, low cost, mild reaction conditions and suitability for industrial production.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to (R)-2-(2-aminothiazol-4-yl)-4'-[2-[(2-hydroxy-2-phenylethyl)amino]ethyl]acetyl The preparation method of phenylaniline (Miraveron) and its intermediates. Background technique [0002] Overactive Bladder (OAB) is a syndrome characterized by symptoms of urinary urgency, often accompanied by frequent urination and nocturia, with or without urge incontinence; it does not include acute urinary tract infection or other Form of symptoms caused by localized lesions of the bladder urethra. The disease has a high incidence rate all over the world and has a great impact on the lives of patients, so it has been paid more and more attention by scholars at home and abroad. It is currently estimated that 50 to 100 million people worldwide suffer from OAB. [0003] Mirabegron is an epinephrine beta developed by Astellas Corporation of Japan 3 Receptor agonist, used for the treatment o...

Claims

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Application Information

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IPC IPC(8): C07C215/30C07C213/00C07D277/40
Inventor 岑均达黄伟李强
Owner SHANGHAI INST OF PHARMA IND
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