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Preparation method of medicine (R)-Bicalutamide for resisting prostatic cancer

An anti-prostate cancer and bicalutamide technology, applied in the field of organic compound preparation, can solve the problem of high production cost and achieve the effects of short reaction time, low environmental pollution and high yield

Active Publication Date: 2010-10-20
湖北省医药工业研究院有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this route uses highly toxic solvents such as benzene and toluene, and flammable and explosive reagents such as sodium hydride, which requires column chromatography purification, and the cost of industrial production is relatively high.

Method used

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  • Preparation method of medicine (R)-Bicalutamide for resisting prostatic cancer

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Experimental program
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Embodiment Construction

[0016] 1. (2R)-1-(2-methacryloyl)tetrahydropyrrole-2-carboxylic acid (Compound I)

[0017] Add D-proline (15g, 0.13mol) acetone (120ml) and 6mol / L sodium hydroxide solution (90ml) dropwise at 0-5°C (the dropping speed should keep the system temperature at 0-5°C) 2-formazol Acryloyl chloride (13.6g, 0.20mol), control the pH above 13, add Bi to rise to room temperature and react for 3h, evaporate acetone and add dilute sulfuric acid (40ml) to adjust the pH to about 2, add sodium chloride to saturation, and use ethyl acetate (100ml×3) extraction, drying over anhydrous sodium sulfate, suction filtration, evaporation of part of the solvent from the filtrate, cooling and adding n-hexane until it becomes cloudy, cooling and crystallizing with ice liquid to give compound I (16.1g) as a white solid, melting point 101-103°C , yield 66.8%.

[0018] 2(3R)-Bromomethyl-3-methyltetrahydropyrrolo[2,1-c][1,4]-oxazine-1,4-dione (Compound II)

[0019] Compound I (16.1g, 0.088mol) in DMF (65ml)...

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Abstract

The invention relates to a preparation method of a medicine (R)-Bicalutamide for resisting prostatic cancer, which comprises the following steps: taking (R)-3-bromine-2-hydroxy-2-methylpropionate as a raw material; carrying out acylation reaction, condensation reaction and oxidizing reaction to obtain the (R)-Bicalutamide, wherein the acylation reaction is carried out in the following steps: dissolving the (R)-3-bromine-2-hydroxy-2-methylpropionate, 4-cyan-3-(trifluoro-methyl)aniline and 4-dimethylamino pyridine into N, N- dimethyl acetamide, dropwise adding thionyl chloride at temperature between minus 10 and minus15 DEG C, then preserving the temperature and reacting for 1-5h after finishing adding the thionyl chloride, heating to room temperature for reaction for 8-12h, and purifying to obtain the (R)-3-bromine-2-hydroxy-2-methyl-N-[4-cyan-3-(trifluoro-methyl phenyl)] propionamide. The preparation method is simple in operation, has short reaction time and high yield, and is suitable for industry production.

Description

Technical field: [0001] The invention relates to the technical field of organic compound preparation, more specifically to a preparation method of anti-prostate cancer drug (R)-bicalutamide. Background technique: [0002] Prostate cancer is currently the most common malignant tumor in men, and its incidence rate ranks second among male cancers. In the drug treatment of prostate cancer, anti-androgen drugs alone or in combination have been widely used clinically as a treatment method for simultaneously blocking the androgen function of the testis and adrenal gland. The non-steroidal androgen antagonist bicalutamide is a relatively new non-steroidal anti-androgen drug developed by Zeneca. The trade name is Casodex. It is a pure anti-androgen drug with specific action Strong, orally effective, convenient administration, good tolerance, and a long half-life. It is the best evaluated and most widely used drug in the treatment of prostate cancer today. [0003] Bicalutamide is ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/46C07C315/02
Inventor 章平荣凌飒刘红王海邹军犬肖志梅刘洁
Owner 湖北省医药工业研究院有限公司
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