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Method for preparing bicalutamide by oxidization

An oxidant and oxidation reaction technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of high production cost and complicated processing, and achieve the effects of no explosion danger, good color and mild reaction conditions

Inactive Publication Date: 2012-01-18
宁波人健药业集团股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The post-treatment of such oxidants is also complicated during oxidation, and the production cost is relatively high

Method used

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  • Method for preparing bicalutamide by oxidization
  • Method for preparing bicalutamide by oxidization
  • Method for preparing bicalutamide by oxidization

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Compound 1 (10.0g, 0.025mol) was dissolved in acetone (50ml), and the reaction temperature was -10°C. Potassium monopersulfate (7.6g, 0.05mol) was added in batches under stirring, and the temperature was maintained for 20h. The reaction solution was poured into water (200ml) and stirred for 30min. Filter, wash the filter cake with water, and blow dry at 50°C to obtain 9.0 g of white bicalutamide solid, with a yield of 84.2%, a melting point of 190-192°C, and an HPLC content of 97.2%.

Embodiment 2

[0035] Compound 1 (10.0 g, 0.025 mol) was dissolved in acetone (50 ml), and the reaction temperature was -10°C. Potassium monopersulfate (11.4 g, 0.075 mol) was added in batches under stirring, and the temperature was maintained for 20 h. The reaction solution was poured into water (200ml) and stirred for 30min. After filtration, the filter cake was washed with water, and air-dried at 50°C to obtain 10.1 g of white bicalutamide solid, with a yield of 94.2%, a melting point of 191-193°C, and an HPLC content of 99.1%.

Embodiment 3

[0037] Compound 1 (10.0 g, 0.025 mol) was dissolved in acetone (50 ml), and the reaction temperature was -10°C. Potassium monopersulfate (15.2 g, 0.10 mol) was added in batches under stirring, and the temperature was maintained for 20 h. The reaction solution was poured into water (200ml) and stirred for 30min. After filtration, the filter cake was washed with water, and air-dried at 50°C to obtain 10.5 g of white bicalutamide solid, with a yield of 97.5%, a melting point of 192-194°C, and an HPLC content of 99.3%.

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Abstract

The invention relates to a method for preparing bicalutamide by oxidization of N-(4-cyan-3-trifluoromethylphenyl)-3-(4-fluorophenylthio)-2-methyl-2-hydroxylpropionamide. The method comprises the step of carrying out oxidization reaction on N-(4-cyan-3-trifluoromethylphenyl)-3-(4-fluorophenylthio)-2-methyl-2-hydroxylpropionamide which is used as a raw material in a solvent in the present of an oxidant so as to prepare the bicalutamide. The method is characterized in that the oxidant is potassium monopersulfate or a complex salt of potassium monopersulfate. Compared with the prior art, the method provided by the invention has the advantages that the bicalutamide is prepared by using potassium monopersulfate or the complex salt of potassium monopersulfate as the oxidant; the oxidant can be abundantly supplied on the market, is cheap in price and available, and cost is greatly reduced; and reaction conditions are mild, and no wastes which can pollute environment are generated.

Description

technical field [0001] The invention relates to a preparation method of an antineoplastic drug bicalutamide. Background technique [0002] Bicalutamide, as a non-steroidal antiandrogen compound, can feedback-inhibit the secretion of gonadotropes from the anterior pituitary gland, which can reduce the production of androgen but has almost no androgen activity. Bicalutamide was successfully developed by British company Astra Zeneca and first launched in the UK in 1995. This drug is used to treat prostate cancer, and it is the most widely used antiandrogen drug. Prostate cancer has a high incidence worldwide and is the second leading cause of death among men. Inhibiting the level of androgen in the body is a common method for the treatment of prostate cancer. Bicalutamide has been widely used in the treatment of prostate cancer because of its strong efficacy, convenient administration and few side effects. [0003] Bicalutamide is produced by oxidation of a bicalutamide thi...

Claims

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Application Information

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IPC IPC(8): C07C317/46C07C315/02
Inventor 顾华平郑飞
Owner 宁波人健药业集团股份有限公司
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