Crystals of bicalutamide and process for their production

A manufacturing method and technology of bicalutamide, applied in the directions of organic chemistry methods, chemical instruments and methods, pharmaceutical formulations, etc., can solve problems such as being unsuitable for industrial production of bicalutamide, not economical, expensive, etc.

Inactive Publication Date: 2005-03-30
SUMITOMO CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method uses an expensive trifluoroacetic anhydride reagent and requires cooling when adding trifluoroacetic anhydride, so it is not an economically superior method
Moreover, due to the corrosive and hygroscopic properties of trifluoroacetic anhydride, this method is not suitable for the industrial production of bicalutamide

Method used

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  • Crystals of bicalutamide and process for their production
  • Crystals of bicalutamide and process for their production
  • Crystals of bicalutamide and process for their production

Examples

Experimental program
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preparation example Construction

[0200] Preparation method of bicalutamide crystal

[0201] In the present invention, the method for preparing bicalutamide crystals is characterized in that the method comprises the following steps I-III:

[0202] 1, the preparation step of the solution containing bicalutamide,

[0203] II. the step of adding a hydrocarbon solvent to the solution obtained in step I when required, and

[0204] III. A step of cooling the solution obtained in step I or II to precipitate bicalutamide crystals.

[0205] Step I

[0206] In step I prepare a bicalutamide-containing solution.

[0207] As for the method of preparing the bicalutamide-containing solution, there may be mentioned, for example, a method of adding a solvent to bicalutamide.

[0208] Solvents that can be exemplified include organic solvents such as ethyl acetate, and ethyl acetate is preferred from the viewpoint of solubility.

[0209] The amount of solvent added per 1 g of bicalutamide is generally 1.0ml-10ml, preferably...

reference example 1

[0232] Preparation of monoperoxyphthalic acid

[0233] Deionized water (125ml), Na 2 CO 3 (31.0g, 0.25mol) and 35% H 2 o 2 (29.15 g, 0.3 mol) were successively charged into 500 ml four-necked flasks, and the mixture was stirred in a dry ice-methanol bath at -5°C to 0°C. Phthalic anhydride (37.0 g, 0.25 mol) was added thereto, and the mixture was stirred for 30 minutes. The bath was removed, ethyl acetate (100ml) was added to the mixture, and 98% HO was diluted with deionized water (50ml). 2 SO 4 (15ml) to neutralize the reaction system. After separating the layers, the aqueous layer was extracted with ethyl acetate (60ml). The obtained organic layer (0.64 g) was taken out, and saturated NaI-IPA (isopropanol) solution (5 ml) and 10% acetic acid-IPA solution (20 ml) were added thereto. Boil the mixture for 5 minutes. Titrate with 0.1N aqueous sodium thiosulfate solution. As a result, there was 33.5 g of monoperoxyphthalic acid, and the yield was 76.9%.

reference example 2

[0235] Synthesis of N-methacryloyl-4-cyano-3-trifluoromethylaniline

[0236] The title compound was prepared according to the method described in J. Med. Chem., 1988, 954-959, using 4-cyano-3-trifluoromethylaniline and methacryloyl chloride as starting materials.

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Abstract

The present invention relates to a crystal of bicalutamide having a defined form, as well as economical and industrially practical production methods of bicalutamide and a crystal thereof, which are superior in environmental benignity and safety. Accordingly, the present invention provides a production method of bicalutamide represented by the formula (I): which includes at least a step of reacting a compound represented by the formula (3): with an oxidizing agent, a production method of a crystal of bicalutamide, as well as a crystal form of bicalutamide as defined by X-ray diffraction (XRD) or solid <13>C NMR measurement.

Description

technical field [0001] The present invention relates to a bicalutamide crystal having a prescribed shape and a method for producing the same. Background technique [0002] Bicalutamide represented by structural formula (I) is reported as: [0003] [0004] (hereinafter sometimes referred to as compound of structural formula (I) or compound (I) in this specification) can be used as compounds having antiangrogenic action (JP-B-4-32061, U.S.P No. 4,636,505 and WO01 / 34563). As for the synthetic method of the compound of structural formula (I), known methods include, for example, 4'-cyano-3-(4-fluorophenylthio)-2-hydroxyl-2-methyl- 3'-Trifluoromethylpropionanilide: [0005] [0006] (hereinafter sometimes referred to as structural formula (3) compound or compound (3)) in dichloromethane solution and the method of meta-chloroperbenzoic acid reaction (Howard Tucker etc., J.Med.Chem., Vol.31,954 -959 (1988), and WO 01 / 28990). This method uses dichloromethane as solvent. H...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61KA61PA61P5/28A61P43/00C07CC07C315/02C07C315/06C07C317/26C07C317/46
CPCC07C317/46C07C315/06C07B2200/13C07C315/02A61P43/00A61P5/00A61P5/28
Inventor 新宅哲也桂正板谷信重
Owner SUMITOMO CHEM CO LTD
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