Sumitomo Chemical Company, Limited

Sumika Fine Chemicals, Co.,ltd.

Tadashi Katsura

Nobushige Itaya

Kiyoshi Sugi

Masayoshi Minai

Masami Igi

Yoshihiro Kawada

Tetsuya Shintaku

Hiroshi Shiratani

Taro Ishibashi

Yayoi Tagami

Teiji Yamaoka

Tadashi Mizuno

Masahide Tanaka

Hiroshi Maeda

Gohfu Suzukamo

Taketo Hayashi

Shigeya Yamazaki

Kozo Matsui

Mitsuhiro Iwasaki

Kazuhiko Hamada

Fujio Masuko

Nobuhiro Arai

A method for producing N-methacryloyl-4-cyano-3-trifluoromethylaniline, wherein 4-cyano-3-trifluoromethylaniline is crystallized from a mixed solvent of methanol and water, and the obtained 4-cyano-3-trifluoromethylaniline is reacted with methacryloyl chloride improved separation property even in industrial production in a large scale.

Method for producing N-methacryloyl-4-cyano-3-trifluoromethylaniline

The present invention provides a method of crystallization of bicalutamide comprising adding an acetone solution containing bicalutamide to water; crystals of bicalutamide wherein particle size distribution of the crystals is 1 to 10 &#x3bc;m of Dp, 10 to 25 &#x3bc;m of Dpand 25 to 100 &#x3bc;m of Dp, and the crystals are obtainable by the method described above; and crystals of bicalutamide, wherein particle size distribution of the crystals is 1 to 3 &#x3bc;m of Dp, 2 to 5 &#x3bc;m of Dpand 5 to 15 &#x3bc;m of Dp.

Method of crystallization of bicalutamide

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 solidC NMR measurement.

Crystal of bicalutamide and production method thereof

The present invention provides a process for recovering 1,3-dimethyl-2-imidazolidinone comprising extracting 1,3-dimethyl-2-imidazolidinone from an aqueous solution containing it with n-butanol in the presence of an inorganic salt to obtain n-butanol layer and, subjecting the n-butanol layer to distillation. As 1,3-dimethyl-2-imidazolidinone can be recoverable at high purity from an aqueous solution containing 1,3-dimethyl-2-imidazolidinone easily and efficiently without using alkali, the present process is industrially advantageous.

Process for recovering 1,3-dimethyl-2-imidazolidinone

The present invention relates to a production method of (R)-3-hydroxy-3-(2-phenylethyl)hexanoic acid which comprises optical resolution of racemic 3-hydroxy-3-(2-phenylethyl)hexanoic acid with an optically active amine of the formula (VIII)wherein Ris 3,4-dimethoxyphenyl or 2-chlorophenyl. According to the present invention, (R)-3-hydroxy-3-(2-phenylethyl)hexanoic acid useful as a starting material of a pharmaceutical agent can be efficiently produced with a high optical purity and a relatively high total yield.

Production method of racemic 3-hydroxy-3-(2-phenylethyl)hexanoic acid C1-6 alkyl ester

Process for preparing a piperidine derivative

Production method of (R)-3 hydroxy-3-(2-phenylethyl) hexanoic acid and intermediate thereof

Piperidine derivative and process for preparing the same

A process for preparing tert-butyl 4&prime;-methyl-2-biphenylcarboxylate characterized in that 4&prime;-methyl-2-biphenylcarboxylic acid is reacted with isobutene in the presence of an acid catalyst. According to the present invention, tert-butyl 4&prime;-methyl-2-biphenylcarboxylate having high quality can be conveniently and industrially advantageously prepared in a high yield under mild reaction conditions such as ambient temperatures without complicated procedures or any hazardous solvents.

Process for producing tert-butyl 4&prime;-methyl-2-biphenylcarboxlate

The present invention provides a crystalline or crystallized acid addition salt of Losartan useful for obtaining highly pure 2-n-butyl-4-chloro-1-&lsqb;&lsqb;2&prime;-(1H-tetrazol-5-yl)&lsqb;1,1&prime;-biphenyl&rsqb;-4-yl&rsqb;methyl&rsqb;-1H-imidazole-5-methanol (Losartan), and a purification method of Losartan that includes production of the crystalline or crystallized acid addition salt.

Crystalline or crystallized acid addition salt of losartan and purification method of losartan

A process for preparing a tert-alkyl carboxylic acid ester represented by the formula (III):

Process for preparing tert-alkyl ester from carboxylic acid

A process for preparing a 2-cyanobiphenyl compound represented by the formula (II): ##STR1## wherein R.sup.1 is an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or hydrogen atom, from a phenylmagnesium chloride compound represented by the formula (I): ##STR2## wherein R.sup.1 is as defined above. According to the process, a 2-cyanobiphenyl compound represented by the formula (II) can be economically, simply, industrially and advantageously prepared.

Process for preparing 2-cyanobiphenyl compound

A piperidine derivative, which can be used as an intermediate for pharmaceuticals such as paroxetine useful as antidepressants, represented by the general formula (I): ##STR1## wherein R.sup.1 is hydrogen atom, benzyloxycarbonyl group or tert-butoxycarbonyl group; R.sup.2 is hydroxymethyl group, an alkylsulfonyloxymethyl group having an alkyl moiety of 1 to 2 carbon atoms, phenylsulfonyloxymethyl group which may have methyl group at the 4-position, (3,4-methylenedioxyphenyl)oxymethyl group, carboxyl group or --CO.sub.2 R.sup.7 group in which R.sup.7 is an alkyl group having 1 to 5 carbon atoms, and Z is methylene group or carbonyl group.

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Osaka, Japan

Tadashi Katsura