Patents Assigned to Sumika Fine Chemicals Co., Ltd.
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Publication number: 20050080278Abstract: The present invention provides a production method of citalopram and intermediates therefor.Type: ApplicationFiled: August 28, 2003Publication date: April 14, 2005Applicant: Sumika Fine Chemicals Co., Ltd.Inventors: Tetsuya Ikemoto, Masami Igi
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Patent number: 6852862Abstract: A process for producing quinoline-3-carboxylic acid represented by formula wherein R1, R2, R3, R4 and R5 have the same meanings as defined below, characterized by reacting 2-aminophenyl ketone represented by formula (1) wherein R1 is an aryl group, a C1-12 alkyl group which may be branched, etc., and R2 and R3 are each a hydrogen atom, a halogen atom, a C1-12 alkyl group which may be branched, etc., with a keto ester represented by formula (2) R4COCH2CO2R5??(2) wherein R4 is a C1-12 alkyl group which may be branched, a C3-6 cycloalkyl group, etc., and R5 is a C1-6 alkyl group which may be branched, in the presence of an acid catalyst in an alcohol solvent while distilling off the alcohol.Type: GrantFiled: February 25, 2002Date of Patent: February 8, 2005Assignees: Sumika Fine Chemicals Co., Ltd., Nissan Chemical Industries, Ltd.Inventors: Susumu Nishizawa, Sadanobu Yoshikawa
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Publication number: 20040267024Abstract: An epoxytriazole derivative (V) useful as an intermediate for anti-fungal agents and an intermediate therefor having high quality can be produced economically and efficiently by the following industrial means. A compound of the following formula (I) is reacted with trimethyloxosulfonium salt and the like in the presence of a base to give compound (II), this compound is converted to compound (IV), and this compound is reacted with 1,2,4-triazole in the presence of a base.Type: ApplicationFiled: May 10, 2004Publication date: December 30, 2004Applicant: Sumika Fine Chemicals Co., Ltd.Inventors: Weiqi Wang, Tetsuya Ikemoto
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Publication number: 20040230066Abstract: Citalopram can be industrially and economically produced and at a high yield by reacting a compound of the following formula [VI] with 3-(dimethylamino)propyl chloride in the presence of at least one of N,N,N′,N′-tetramethylethylenediamine and 1,3-dimethyl-2-imidazolidinone and a condensing agent. The compound of the following formula [III], which is a key compound for the production of citalopram, can be easily produced by subjecting the compound of the following formula [II] to reduction and cyclization.Type: ApplicationFiled: June 14, 2004Publication date: November 18, 2004Applicant: Sumika Fine Chemicals Co., Ltd.Inventors: Tetsuya Ikemoto, Wei-Guo Gao, Masami Igi
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Patent number: 6815548Abstract: A piperidine derivative, which can be used as an intermediate for pharmaceuticals such as paroxetine useful as antidepressants, represented by the general formula (I): wherein R1 is hydrogen atom, benzyloxycarbonyl group or tert-butoxycarbonyl group; R2 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 —CO2R7 group in which R7 is an alkyl group having 1 to 5 carbon atoms, and Z is methylene group or carbonyl group, with proviso that, (A) when R1 is benzyloxycarbonyl group or tert-butoxycarbonyl group, then R2 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 or (3,4-methylenedioxyphenyl)oxymethyl group, and Z is methylene group; or (B) when R1 is hydrogen atom and Z is caType: GrantFiled: January 6, 2003Date of Patent: November 9, 2004Assignee: Sumika Fine Chemicals Co., Ltd.Inventors: Kiyoshi Sugi, Nobushige Itaya, Tadashi Katsura, Masami Igi, Shigeya Yamazaki, Taro Ishibashi, Teiji Yamaoka, Yoshihiro Kawada, Yayoi Tagami
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Publication number: 20040162340Abstract: The present invention provides a method for producing compound (XIV) useful as an intermediate for pharmaceutical agents efficiently and economically on an industrial scale without using ozone oxidation and highly toxic reagent, and an intermediate used for this method. Particularly, the present invention provides a method for producing a compound having an absolute configuration represented by the formula (XV) and an enantiomer thereof without using a technique such as optical resolution and the like, and an intermediate used for this method.Type: ApplicationFiled: December 23, 2003Publication date: August 19, 2004Applicant: Sumika Fine Chemicals Co., Ltd.Inventors: Tetsuya Ikemoto, Dongguo Piao
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Patent number: 6777576Abstract: The present invention relates to production of 2-cyclohexyl-2-hydroxy-2-phenylacetic acid useful as an intermediate for pharmaceutical products, by an industrial means, economically, safely in a good yield. Novel 2-(2′-cyclohexen-1′-yl)-2-hydroxy-2-phenylacetic acid ester obtained by reacting cyclohexene and benzoylformic acid ester in the presence of a Lewis acid is hydrolyzed and reduced to give 2-cyclohexyl-2-hydroxy-2-phenylacetic acid.Type: GrantFiled: November 6, 2001Date of Patent: August 17, 2004Assignee: Sumika Fine Chemicals Co., Ltd.Inventors: Tetsuya Ikemoto, Wei-Guo Gao, Mitsuhiro Takeda, Masami Igi
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Publication number: 20040138496Abstract: 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) 1Type: ApplicationFiled: December 4, 2003Publication date: July 15, 2004Applicant: Sumika Fine Chemicals Co., Ltd.Inventors: Masahide Tanaka, Kozo Matsui, Tadashi Katsura, Mitsuhiro Iwasaki, Hiroshi Maeda, Nobushige Itaya
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Publication number: 20040138447Abstract: Low-hygroscopic anhydrous mirtazapine crystals having a hygroscopic degree of not more than 0.6% by weight when the crystals are stored in the air having a relative humidity of 75% at 25° C. under atmospheric pressure for 500 hours; a process for preparing anhydrous mirtazapine crystals having a hygroscopic degree of not more than 0.6% by weight when the crystals are stored in the air having a relative humidity of 75% at 25° C.Type: ApplicationFiled: December 24, 2003Publication date: July 15, 2004Applicant: Sumika Fine Chemicals Co., Ltd.Inventors: Eiichi Iishi, Yoshiyuki Imamiya
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Publication number: 20040138497Abstract: Citalopram can be industrially and economically produced and at a high yield by reacting a compound of the following formula [VI] with 3-(dimethylamino)propyl chloride in the presence of at least one of N,N,N′,N′-tetramethylethylenediamine and 1,3-dimethyl-2-imidazolidinone and a condensing agent. The compound of the following formula [III], which is a key compound for the production of citalopram, can be easily produced by subjecting the compound of the following formula [II] to reduction and cyclization.Type: ApplicationFiled: December 23, 2003Publication date: July 15, 2004Applicant: Sumika Fine Chemicals Co., Ltd.Inventors: Tetsuya Ikemoto, Wei-Guo Gao, Masami Igi
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Publication number: 20040133031Abstract: 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.Type: ApplicationFiled: December 18, 2003Publication date: July 8, 2004Applicant: Sumika Fine Chemicals Co., Ltd.Inventors: Tetsuya Shintaku, Tadashi Katsura, Nobushige Itaya
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Patent number: 6740770Abstract: 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 13C NMR measurement.Type: GrantFiled: February 24, 2003Date of Patent: May 25, 2004Assignee: Sumika Fine Chemicals Co., Ltd.Inventors: Tetsuya Shintaku, Tadashi Katsura, Nobushige Itaya
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Patent number: 6730803Abstract: The &bgr;-keto ester compound, &bgr;-hydroxy acid compound and acetonide form of a 1,3-diol derivative of the formulas (I), (V) and (VIII) wherein each symbol is as defined in the specification, are useful as a synthetic intermediate for an epothilone derivative being developed as a pharmaceutical agent having an antitumor activity.Type: GrantFiled: September 30, 2002Date of Patent: May 4, 2004Assignee: Sumika Fine Chemicals Co., Ltd.Inventors: Mitsuhiro Iwasaki, Kiyoshi Sugi, Hideto Miyamoto, Nobushige Itaya
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Patent number: 6723845Abstract: Low-hygroscopic anhydrous mirtazapine crystals having a hygroscopic degree of not more than 0.6% by weight when the crystals are stored in the air having a relative humidity of 75% at 25° C. under atmospheric pressure for 500 hours; a process for preparing anhydrous mirtazapine crystals having a hygroscopic degree of not more than 0.6% by weight when the crystals are stored in the air having a relative humidity of 75% at 25° C. under atmospheric pressure for 500 hours, comprising drying crystals of mirtazapine hydrate; a crystal of a mirtazapine hydrate represented by the formula (I): wherein n is an integer of 1 to 5; and a process for preparing crystals of a mirtazapine hydrate, comprising crystallizing a crude mirtazapine using a water-soluble organic solvent and water. The anhydrous mirtazapine crystals can be suitably used, for instance, as an antidepressant.Type: GrantFiled: January 7, 2003Date of Patent: April 20, 2004Assignee: Sumika Fine Chemicals Co., Ltd.Inventors: Eiichi Iishi, Yoshiyuki Imamiya
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Publication number: 20040044232Abstract: The present invention provides a production method of a 5-phthalancarbonitrile compound, which comprises the use of a novel compound of the formula [I] 1Type: ApplicationFiled: August 28, 2003Publication date: March 4, 2004Applicant: Sumika Fine Chemicals Co., Ltd.Inventors: Tetsuya Ikemoto, Masami Igi
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Patent number: 6683207Abstract: 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 R2 is 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.Type: GrantFiled: December 16, 2002Date of Patent: January 27, 2004Assignee: Sumika Fine Chemicals Co., Ltd.Inventors: Masahide Tanaka, Kozo Matsui, Tadashi Katsura, Mitsuhiro Iwasaki, Hiroshi Maeda, Nobushige Itaya
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Publication number: 20030236419Abstract: An epoxytriazole derivative (V) useful as an intermediate for anti-fungal agents and an intermediate therefor having high quality can be produced economically and efficiently by the following industrial means. A compound of the following formula (I) is reacted with trimethyloxosulfonium salt and the like in the presence of a base to give compound (II), this compound is converted to compound (IV), and this compound is reacted with 1,2,4-triazole in the presence of a base.Type: ApplicationFiled: December 31, 2002Publication date: December 25, 2003Applicant: Sumika Fine Chemicals Co., Ltd.Inventors: Weiqi Wang, Tetsuya Ikemoto
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Publication number: 20030233009Abstract: The present invention relates to a production method of 4′-bromomethyl-2-cyanobiphenyl, which includes reacting 4′-methyl-2-cyanobiphenyl with bromine in the presence of a radical initiator and an oxidant. According to the present invention, since bromine can be regenerated by reacting hydrogen bromide, which is by-produced with the progress of bromination, with an oxidant, inhibition of bromination by hydrogen bromide, coloring by bromine and the like can be prevented. Thus, 4′-bromomethyl-2-cyanobiphenyl useful as a starting material of pharmaceutical products can be produced industrially beneficially.Type: ApplicationFiled: December 17, 2002Publication date: December 18, 2003Applicant: Sumika Fine Chemicals Co., Ltd.Inventors: Seiji Yamada, Ken Ishihara, Toshio Nakamatsu
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Patent number: 6660730Abstract: Methods for producing anhydrous mirtazapine crystals that are either (1) substantially free of lower alcohol insolubles or (2) substantially free of residual solvent and have an average particle diameter of from 10 to 50 &mgr;m, are provided, and the resulting anhydrous mirtazapine crystals produced thereby, which are useful in pharmaceuticals.Type: GrantFiled: April 27, 2001Date of Patent: December 9, 2003Assignee: Sumika Fine Chemicals Co., Ltd.Inventors: Chiharu Maeda, Sadanobu Yoshikawa, Eiichi Iishi
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Patent number: 6649768Abstract: A production method including a step for converting a halogen compound of the formula (6) or a salt thereof to a glyoxal compound of the formula (2) or a salt thereof in dimethyl sulfoxide, and a step for reacting the glyoxal compound of the formula (2) or a salt thereof obtained in the previous step with ammonia and an aldehyde compound of the formula (3) or a salt thereof can conveniently produce an imidazole compound of the formula (1) or a salt thereof. The imidazole compound is a synthetic intermediate for a compound useful as pharmaceutical agents and agricultural chemicals. The production method is suitable for industrial scale production. is wherein each symbol is as defined in the specification.Type: GrantFiled: December 4, 2002Date of Patent: November 18, 2003Assignee: Sumika Fine Chemicals Co., Ltd.Inventors: Tetsuya Shintaku, Nobushige Itaya