Patents by Inventor Chojiro Higuchi
Chojiro Higuchi has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 4962222Abstract: .alpha.-L-Aspartyl-L-phenylalanine methyl ester having low hygroscopicity is prepared by bringing a cake of .alpha.-L-aspartyl-L-phenylalanine methyl ester, which cake has been obtained by solid-liquid separation through a desired preparation process of .alpha.-L-aspartyl-L-phenylalanine methyl ester, into contact with an organic solvent of uniform phase so as to treat the cake with the organic solvent, subjecting the resulting mixture of the cake and organic solvent to solid-liquid separation to obtain a cake, and then drying the last-mentioned cake at a temperature not higher than 60.degree. C. The organic solvent is dry or contains water in an amount up to 30 wt.%.Type: GrantFiled: January 25, 1989Date of Patent: October 9, 1990Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Ryuichi Mita, Toshio Katoh, Chojiro Higuchi, Takeshi Oura, Akihiro Yamaguchi
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Patent number: 4918216Abstract: .alpha.-L-aspartyl-L-phenylalanine methyl ester or the hydrohalide thereof is prepared by esterifying .alpha.-L-aspartyl-L-phenylalanine or .alpha.-L-aspartyl-L-phenylalanine which has been formed in situ by treating an N-protected-.alpha.-L-aspartyl-L-phenylalanine in an aqueous solution of sulfuric acid or a methanol-containing aqueous solution of sulfuric acid in the presence of an alkali metal halide or alkaline earth metal halide in a medium composed of sulfuric acid, water and methanol, thereby to allow the resulting .alpha.-L-aspartyl-L-phenyl-alanine methyl ester to precipitate as its corresponding hydrohalide, and then isolating the hydrohalide; and when the preparation of the methyl ester is desired, neutralizing the hydrohalide.Type: GrantFiled: May 25, 1989Date of Patent: April 17, 1990Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Ryuichi Mita, Toshio Katoh, Chojiro Higuchi, Takeshi Oura, Akihiro Yamaguchi
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Patent number: 4897506Abstract: A method for preparing .alpha.-L-aspartyl-L-phenylalanine methyl ester having improved solubilization by the isolation thereof from an aqueous medium containing at least one additive selected from the group consisting of sodium alginate, sodium salt of carboxymethylcellulose, sodium starch glycolate and sodium polyacrylate.Type: GrantFiled: October 12, 1988Date of Patent: January 30, 1990Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Ryuichi Mita, Takeshi Oura, Toshio Katoh, Chojiro Higuchi, Akihiro Yamaguchi, Masanobu Ajioka
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Patent number: 4801732Abstract: This invention relates to an improved process for preparing .alpha.-L-aspartyl-L-phenylalanine methyl ester. More specifically, it relates to a process for preparing .alpha.-L-aspartyl-L-phenylalanine methyl ester which comprises treating, as a raw material, N-formyl-.alpha.-L-aspartyl-L-phenylalanine in methanol in the presence of an acid to form .alpha.-L-aspartyl-L-phenylalanine dimethyl ester, hydrolyzing the .alpha.-L-aspartyl-L-phenylalanine dimethyl ester by bringing it into contact with hydrochloric acid in the presence of methanol as desired, separating the thereby-precipitated .alpha.-L-aspartyl-L-phenylalanine methyl ester hydrochloride and neutralizing the hydrochloride. Further, this invention also provides a process for preparing .alpha.-L-aspartyl-L-phenylalanine methyl ester capable of using, as a raw material, N-formyl-.alpha.-L-aspartyl-L-phenylalanine which contains N-formyl-.beta.-L-aspartyl-L-phenylalanine in an amount of 30% by weight or less.Type: GrantFiled: March 22, 1988Date of Patent: January 31, 1989Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Ryuichi Mita, Takeshi Oura, Chojiro Higuchi, Toshio Katoh, Akihiro Yamaguchi
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Patent number: 4780561Abstract: Disclosed herein is a process for preparing .alpha.-L-aspartyl-L-phenylalanine methyl ester or its hydrochloride from 5-benzyl-3,6-dioxo-2-piperazine acetic acid or its methyl ester, prepared without using L-penylalanine methyl ester which involves problems in its stability, as a raw material. Specifically, the process comprises: bringing 5-benzyl-3,6-dioxo-2-piperazine acetic acid in the presence of methanol or 5-benzyl-3,6-dioxo-2-piperazine acetic acid methyl ester in the presence or absence of methanol into contact with hydrochloric acid; isolating the thereby deposited .alpha.-L-aspartyl-L-phenylalanine methyl ester hydrochloride; and neutralizing said hydrochloride with an alkali as required. Preparation processes of 5-benzyl-3,6-dioxo-2-piperazine acetic acid or its methyl ester are also disclosed.Type: GrantFiled: December 9, 1987Date of Patent: October 25, 1988Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Ryuichi Mita, Takeshi Oura, Toshio Katoh, Chojiro Higuchi, Akihiro Yamaguchi
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Patent number: 4778916Abstract: The present invention relates to a process for preparing .alpha.-L-aspartyl-L-phenylalanine methyl ester or its hydrochloride. .alpha.-L-aspartyl-L-phenylalanine methyl ester or its hydrochloride is prepared by a process comprising: condensating N-formyl-L-aspartic acid anhydride and L-phenylalanine in water or in water containing methanol at a pH in the range of 7-12 to form N-formyl-.alpha.-L-aspartyl-L-phenylalanine; acidifying the reaction mixture successively with hydrochloric acid in the presence of methanol without isolating the N-formyl-.alpha.-L-aspartyl-L-phenylalanine so as to bring it into contact with hydrochloric acid in the presence of methanol for reaction and thereby to deposit .alpha.-L-aspartyl-L-phenylalanine methyl ester hydrochloride; separating the .alpha.-L-aspartyl-L-phenylalanine methyl ester hydrochloride; and neutralizing said hydrochloride as required.Type: GrantFiled: November 17, 1987Date of Patent: October 18, 1988Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Ryuichi Mita, Toshio Katoh, Chojiro Higuchi, Takeshi Oura, Akihiro Yamaguchi
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Patent number: 4745210Abstract: This invention relates to an improved process for preparing N-formyl-.alpha.- aspartyl phenylalanine. More specifically, it relates to a process for preparing N-formyl-.alpha.-aspartyl phenylalanine by condensating N-formyl aspartic acid anhydride and phenylalanine which comprises effecting the condensation reaction in a water medium while maintaining the pH during the reaction in the range of 7-12 and at a reaction temperature of 50.degree. C. or below.Type: GrantFiled: December 4, 1985Date of Patent: May 17, 1988Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Ryuichi Mita, Toshio Katoh, Chojiro Higuchi, Takeshi Oura, Akihiro Yamaguchi
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Patent number: 4675439Abstract: A process for preparing an N-acylphenylalanine represented by the formula (II): ##STR1## wherein R.sub.3 and R.sub.4 mean individually a hydrogen atom or an alkyl, alkoxy, phenoxy, hydroxy or methylenedioxy group, and R denotes a methyl or phenyl group, which comprises catalytically reducing an N-acyl-.beta.-phenylserine represented by the formula (I): ##STR2## wherein R.sub.1 and R.sub.2 mean individually a hydrogen atom or an alkyl, alkoxy, phenoxy, benzyloxy or methylenedioxy group, and R has the same meaning as defined in the formula (II), in the presence of a reducing catalyst or both reducing catalyst and acid, in a solvent.Type: GrantFiled: November 4, 1985Date of Patent: June 23, 1987Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Ryuichi Mita, Toshio Katoh, Chojiro Higuchi, Akihiro Yamaguchi
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Patent number: 4612388Abstract: Disclosed herein is a process for producing an N-acyl-substituted or unsubstituted phenylalanine comprising hydrolyzing a 2-substituted-4-substituted or unsubstituted benzylidene-5-oxazolone with alkali, adjusting pH of the reaction solution containing its hydrolysis product with acid at 5-9 and reducing the resultant reaction solution catalytically in the presence of a palladium or platinum reducing catalyst.In accordance with the process of the present invention, time duration required for effecting the reduction can be shortened markedly in comparison with the reduction in an aqueous strong alkaline solution. Moreover, the catalyst recovered after completion of the reduction can be used repeatedly without any additional treatment and without any observed lowering in its activity. Accordingly, the reduction using the recovered catalyst may proceed in practically the same time as in the case of using a fresh catalyst.Type: GrantFiled: April 3, 1985Date of Patent: September 16, 1986Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Ryuichi Mita, Toshio Katoh, Chojiro Higuchi, Akihiro Yamaguchi
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Patent number: 4605759Abstract: In the production of a .beta.-phenylserine by reacting glycine with a benzaldehyde in the presence of an alkali and treating the product with an acid, a novel process which comprises carrying out the reaction in a mixed solvent composed of water and a hydrophobic organic solvent. The presence of a phase transfer catalyst or a surface-active agent in this reaction system promotes the reaction and the .beta.-phenylserine can be obtained in a high yield.Type: GrantFiled: July 31, 1984Date of Patent: August 12, 1986Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Ryuichi Mita, Toshio Katoh, Chojiro Higuchi, Akihiro Yamaguchi
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Patent number: 4484003Abstract: .beta.-Chloroalanine is prepared by reacting in an aqueous medium an aziridine-2-carboxylate with hydrogen chloride in an amount of 2.0-5.0 moles per mole of the aziridine-2-carboxyalte and causing the thus-formed .beta.-chloroalanine to selectively crystallize out from the liquid reaction mixture. Since the solution recovered after the isolation of the crystallized .beta.-chloroalanine still contains .beta.-chloroalanine and by-produced .alpha.-chloro-.beta.-alanine dissolved therein, they may be converted into an aziridine-2-carboxylate by treating them with a base to recirculate it for reuse.Type: GrantFiled: December 29, 1982Date of Patent: November 20, 1984Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Masaharu Ohoka, Toshio Katoh, Ryuichi Mita, Nobuyuki Kawashima, Chojiro Higuchi, Nobuhiro Kawashima, Akihiro Yamaguchi, Shousuke Nagai, Takao Takano
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Patent number: 4453008Abstract: DL-cystein is produced by reacting a .beta.-halogenoalanine with a trithiocarbonate to obtain the mono(aminocarboxyethyl) ester of trithiocarbonate and then subjecting the ester to acid decomposition. The above process requires mild reaction conditions, is easy to carry out its reactions and can afford DL-cystein with high yield. It is thus an excellent production process of DL-cystein from the industrial viewpoint.Type: GrantFiled: January 14, 1983Date of Patent: June 5, 1984Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Ryuichi Mita, Masaharu Ohoka, Chojiro Higuchi, Toshio Katoh, Nobuyuki Kawashima, Akihiro Yamaguchi, Shousuke Nagai, Takao Takano
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Patent number: 4393000Abstract: A process for producing aziridine-2-carboxylic acid or its salts is provided which comprises treating an alpha-halogeno-beta-aminopropionitrile or its mineral acid salt with an alkali or alkaline earth metal hydroxide in water or in a water-containing organic solvent. In a preferred embodiment, aziridine-2-carboxylic acid or its salt is produced by treating the reaction mixture containing an alpha-halogeno-beta-aminopropionitrile obtained by reacting an alpha, beta-dihalogenopropionitrile or an alpha-halogenoacrylonitrile with ammonia, with an alkali or alkaline earth metal hydroxide in the presence of water without isolating the alpha-halogeno-beta-aminopropionitrile from the reaction mixture beforehand.Type: GrantFiled: December 9, 1980Date of Patent: July 12, 1983Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Ryuichi Mita, Chojiro Higuchi, Toshio Kato, Nobuyuki Kawashima, Akihiro Yamaguchi, Shosuke Nagai, Takao Takano
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Patent number: 4342700Abstract: An oxidation-reducing reagent for a wet desulfurization process, which comprises (a) one or more compounds selected from the group consisting of salts of substituted anthraquinonesulfonic acids of the general formulas: ##STR1## wherein M stands for a sodium atom, a potassium atom or an ammonium group, and n is an integer of 1 or 2, or (b) a mixture of a salt of anthraquinone-2,7-disulfonic acid and one or more compounds shown by the general formula (I) and/or (II), as well as a process for preparing the compounds of the general formulas (I) and (II).Type: GrantFiled: February 4, 1981Date of Patent: August 3, 1982Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Katsuya Sakai, Ryuichi Mita, Toshio Kato, Chojiro Higuchi, Hisamichi Murakami
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Patent number: 4338259Abstract: A process for producing an alpha-halogeno-beta-aminopropionitrile which comprises reacting an alpha,beta-dihalogenopropionitrile with ammonia in water and/or an organic solvent. Action of a mineral acid on the reaction product gives a mineral acid salt of an alpha-halogeno-beta-aminopropionitrile. An isolated alpha-halogeno-beta-aminopropionitrile and a sulfate thereof are also provided.Type: GrantFiled: July 30, 1980Date of Patent: July 6, 1982Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Ryuichi Mita, Akihiro Yamaguchi, Toshio Kato, Chojiro Higuchi, Hisamichi Murakami
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Patent number: 4304933Abstract: Production of DL-serine by heating a strong acid type cation exchange resin having aziridine-2-carboxylic acid absorbed thereto. Specifically, an industrial process for producing DL-serine is provided which comprises treating an alpha-halogeno-beta-aminopropionitrile or its mineral acid salt in water or a water-containing organic solvent with an alkali or alkaline earth metal hydroxide to form an alkali or alkaline earth metal aziridine-2-carboxylate, treating the reaction mixture with a strong acid type cation exchange resin to cause adsorption of aziridine-2-carboxylic acid, and thereafter heating the cation-exchange resin.Type: GrantFiled: December 2, 1980Date of Patent: December 8, 1981Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Ryuichi Mita, Chojiro Higuchi, Toshio Kato, Nobuyuki Kawashima, Akihiro Yamaguchi, Shosuke Nagai, Takao Takano
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Patent number: 4276187Abstract: An oxidation-reducing reagent for a wet desulfurization process, which comprises (a) one or more compounds selected from the group consisting of salts of substituted anthraquinonesulfonic acids of the general formulas: ##STR1## wherein M stands for a sodium atom, a potassium atom or an ammonium group, and n is an integer of 1 or 2, or (b) a mixture of a salt of anthraquinone-2,7-disulfonic acid and one or more compounds shown by the general formula (I) and/or (II), as well as a process for preparing the compounds of the general formulas (I) and (II).Type: GrantFiled: April 4, 1979Date of Patent: June 30, 1981Assignee: Mitsui Toatsu Chemicals IncorporatedInventors: Katsuya Sakai, Ryuichi Mita, Toshio Kato, Chojiro Higuchi, Hisamichi Murakami