Patents by Inventor Masaki NAGAHAMA
Masaki NAGAHAMA 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: 12187664Abstract: High purity 2-naphthylacetonitrile with fewer impurities that is useful as a starting material or intermediate for the synthesis of various pharmaceutical products, agricultural chemicals, and chemical products, and a production method thereof. A high purity 2-naphthylacetonitrile having an HPLC purity of 2-naphthylacetonitrile of not less than 95 area %, and containing naphthalene compounds represented by the formulas (a)-(j) at a content of a predetermined area % or below. A method for producing high purity 2-naphthylacetonitrile.Type: GrantFiled: March 27, 2023Date of Patent: January 7, 2025Assignee: API CORPORATIONInventors: Masaki Nagahama, Daiki Okado, Hirotsugu Taniike
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Publication number: 20240391860Abstract: Salicylic acid is produced with high productivity by reacting 2-halogenated benzoic acid in an aqueous solvent at a reaction temperature of 155° C. or higher and 300° C. or lower in the presence of a copper source and a ligand. Preferably, the method further includes a purification step A in which the obtained salicylic acid is brought into contact with a styrene-based synthetic adsorbent and/or a purification step B in which the obtained salicylic acid is brought into contact with zeolite. The compound is led to raw materials for various pharmaceuticals or intermediates thereof (for example, acetylsalicylic acid).Type: ApplicationFiled: August 26, 2022Publication date: November 28, 2024Applicant: API CORPORATIONInventors: Hirotsugu TANIIKE, Shunsuke TSUJI, Masaki NAGAHAMA, Yurie KOBA
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Publication number: 20240360086Abstract: An object of the present invention is to provide a novel method capable of producing rosuvastatin calcium and intermediates therefor efficiently, inexpensively and with high purity. The present invention provides a method of efficiently producing rosuvastatin calcium and intermediates therefor having a high purity at an industrial scale, without using an extremely low temperature reaction or a special asymmetric catalyst.Type: ApplicationFiled: June 21, 2024Publication date: October 31, 2024Applicant: API CORPORATIONInventors: Tomoko MAEDA, Yasumasa DEKISHIMA, Hiroshi KAWABATA, Masaki NAGAHAMA, Naoyuki WATANABE, Kosuke ITO
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Publication number: 20240351978Abstract: The present invention provides a method for industrially producing a highly pure aromatic nitrile compound and a highly pure aromatic carboxylic acid compound safely and highly efficiently at low costs. Compound (2) is subjected to Willgerodt reaction in the presence of an additive as necessary, and the obtained amide compound (3) is hydrolyzed and neutralized to give carboxylic acid compound (4). Carboxylic acid compound (4) is reacted with a halogenating agent in the presence of a catalyst as necessary in an organic solvent, and further reacted with an amidating agent, and the obtained amide compound (5) or (6) is reacted with a dehydrating agent to give nitrile compound (1). Alternatively, carboxylic acid compound (4) is reacted with a halogenating agent and a compound represented by the formula R6SO2R7 in the presence of a catalyst as necessary in an organic solvent to give nitrile compound (1).Type: ApplicationFiled: June 10, 2024Publication date: October 24, 2024Applicant: API CORPORATIONInventors: Masaki NAGAHAMA, Hideki OOMIYA, Daiki OKADO, Hirotsugu TANIIKE
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Patent number: 12091390Abstract: An object of the present invention is to provide a novel method capable of producing rosuvastatin calcium and intermediates therefor efficiently, inexpensively and with high purity. The present invention provides a method of efficiently producing rosuvastatin calcium and intermediates therefor having a high purity at an industrial scale, without using an extremely low temperature reaction or a special asymmetric catalyst.Type: GrantFiled: June 17, 2019Date of Patent: September 17, 2024Assignee: API CORPORATIONInventors: Naoyuki Watanabe, Tomoko Maeda, Yasumasa Dekishima, Hiroshi Kawabata, Masaki Nagahama
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Patent number: 12084404Abstract: The present invention provides high purity 2-naphthylacetonitrile with fewer impurities that is useful as a starting material or intermediate for the synthesis of various pharmaceutical products, agricultural chemicals, and chemical products, and a production method thereof. A high purity 2-naphthylacetonitrile having an HPLC purity of 2-naphthylacetonitrile of not less than 95 area %, and containing naphthalene compounds represented by the formulas (a)-(j) at a content of a predetermined area % or below. A method for producing high purity 2-naphthylacetonitrile, including the following step 1 and step 2: step 1: a step of subjecting 2?-acetonaphthone to a Willgerodt reaction in the presence of an additive where necessary, and hydrolyzing the obtained amide compound to give 2-naphthylacetic acid; step 2: a step of reacting the 2-naphthylacetic acid obtained in step 1, a halogenating agent and sulfamide in the presence of a catalyst as necessary in an organic solvent to give 2-naphthylacetonitrile.Type: GrantFiled: May 25, 2022Date of Patent: September 10, 2024Assignee: API CORPORATIONInventors: Masaki Nagahama, Daiki Okado, Hirotsugu Taniike
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Patent number: 12054448Abstract: The present invention provides a method for industrially producing a highly pure aromatic nitrile compound and a highly pure aromatic carboxylic acid compound safely and highly efficiently at low costs. Compound (2) is subjected to Willgerodt reaction in the presence of an additive as necessary, and the obtained amide compound (3) is hydrolyzed and neutralized to give carboxylic acid compound (4). Carboxylic acid compound (4) is reacted with a halogenating agent in the presence of a catalyst as necessary in an organic solvent, and further reacted with an amidating agent, and the obtained amide compound (5) or (6) is reacted with a dehydrating agent to give nitrile compound (1). Alternatively, carboxylic acid compound (4) is reacted with a halogenating agent and a compound represented by the formula R6SO2R7 in the presence of a catalyst as necessary in an organic solvent to give nitrile compound (1).Type: GrantFiled: April 26, 2019Date of Patent: August 6, 2024Assignee: API CORPORATIONInventors: Masaki Nagahama, Hideki Oomiya, Daiki Okado, Hirotsugu Taniike
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Patent number: 12037307Abstract: The present invention provides high purity 2-naphthylacetonitrile with fewer impurities that is useful as a starting material or intermediate for the synthesis of various pharmaceutical products, agricultural chemicals, and chemical products, and a production method thereof. A high purity 2-naphthylacetonitrile having an HPLC purity of 2-naphthylacetonitrile of not less than 95 area %, and containing naphthalene compounds represented by the formulas (a)-(j) at a content of a predetermined area % or below. A method for producing high purity 2-naphthylacetonitrile, including the following step 1 and step 2: step 1: a step of subjecting 2?-acetonaphthone to a Willgerodt reaction in the presence of an additive where necessary, and hydrolyzing the obtained amide compound to give 2-naphthylacetic acid; step 2: a step of reacting the 2-naphthylacetic acid obtained in step 1, a halogenating agent and sulfamide in the presence of a catalyst as necessary in an organic solvent to give 2-naphthylacetonitrile.Type: GrantFiled: May 25, 2022Date of Patent: July 16, 2024Assignee: API CORPORATIONInventors: Masaki Nagahama, Daiki Okado, Hirotsugu Taniike
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Publication number: 20240158328Abstract: A method for producing a cyclohexenone compound, comprising: an isomerization step of bringing a reaction raw material including the compound represented by the following formula (4) into contact with an isomerization catalyst in a solvent to obtain the compound represented by the following formula (3). Preferably, an addition step of reacting the compound (1) and methyl vinyl ketone in a solvent in the presence of a base to obtain compound (2); a cyclization step of reacting compound (2) in a solvent in the presence of a strong acid to obtain compound (3); and an isomerization step of bringing compound (4) contained as an impurity in the reaction product of the cyclization step into contact with an isomerization catalyst in a solvent are performed in order.Type: ApplicationFiled: February 15, 2022Publication date: May 16, 2024Applicant: API CORPORATIONInventors: Masaki NAGAHAMA, Hirotsugu TANIIKE, Jun INOUE
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Publication number: 20240109840Abstract: A method for producing a 2-(halogenated methyl)naphthalene represented by general formula (1): where X is a halogen atom. The method includes a halogenation process of reacting 2-methylnaphthalene with a halogenating agent under light irradiation, in an organic solvent selected from a halogenated hydrocarbon, an aliphatic ester and an aliphatic hydrocarbon.Type: ApplicationFiled: August 27, 2021Publication date: April 4, 2024Applicant: API CORPORATIONInventors: Shunsuke TSUJI, Masaki NAGAHAMA, Hirotsugu TANIIKE
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Publication number: 20230227400Abstract: High purity 2-naphthylacetonitrile with fewer impurities that is useful as a starting material or intermediate for the synthesis of various pharmaceutical products, agricultural chemicals, and chemical products, and a production method thereof. A high purity 2-naphthylacetonitrile having an HPLC purity of 2-naphthylacetonitrile of not less than 95 area %, and containing naphthalene compounds represented by the formulas (a)-(j) at a content of a predetermined area % or below. A method for producing high purity 2-naphthylacetonitrile.Type: ApplicationFiled: March 27, 2023Publication date: July 20, 2023Applicant: API CORPORATIONInventors: Masaki NAGAHAMA, Daiki OKADO, Hirotsugu TANIIKE
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Patent number: 11643386Abstract: High purity 2-naphthylacetonitrile with fewer impurities can be used as a starting material or intermediate for synthesizing various pharmaceutical products, agricultural chemicals, and chemical products, and a production method thereof. A high purity 2-naphthylacetonitrile having an HPLC purity of 2-naphthylacetonitrile of not less than 95 area %, and containing naphthalene compounds represented by the formulas (a)-(j) at a content of a predetermined area % or below. A method for producing high purity 2-naphthylacetonitrile, may include: subjecting 2?-acetonaphthone to a Willgerodt reaction in the presence of an additive where necessary, and hydrolyzing the obtained amide compound to give 2-naphthylacetic acid; and reacting the 2-naphthylacetic acid obtained in the subjecting, a halogenating agent and sulfamide in the presence of a catalyst as necessary in an organic solvent to give 2-naphthylacetonitrile.Type: GrantFiled: October 28, 2020Date of Patent: May 9, 2023Assignee: API CORPORATIONInventors: Masaki Nagahama, Daiki Okado, Hirotsugu Taniike
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Patent number: 11623943Abstract: The present invention provides a method of industrially and safely producing lacosamide high in diastereomeric excess at a high yield and a low cost. Adopting a particular isomerization-crystallization condition makes it possible to a method of industrially and safely producing lacosamide high in diastereomeric excess at a high yield and a low cost. Additionally, an intermediate efficacious for producing lacosamide is provided.Type: GrantFiled: March 9, 2021Date of Patent: April 11, 2023Assignee: API CORPORATIONInventor: Masaki Nagahama
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Publication number: 20220281806Abstract: The present invention provides high purity 2-naphthylacetonitrile with fewer impurities that is useful as a starting material or intermediate for the synthesis of various pharmaceutical products, agricultural chemicals, and chemical products, and a production method thereof. A high purity 2-naphthylacetonitrile having an HPLC purity of 2-naphthylacetonitrile of not less than 95 area %, and containing naphthalene compounds represented by the formulas (a)-(j) at a content of a predetermined area % or below. A method for producing high purity 2-naphthylacetonitrile, including the following step 1 and step 2: step 1: a step of subjecting 2?-acetonaphthone to a Willgerodt reaction in the presence of an additive where necessary, and hydrolyzing the obtained amide compound to give 2-naphthylacetic acid; step 2: a step of reacting the 2-naphthylacetic acid obtained in step 1, a halogenating agent and sulfamide in the presence of a catalyst as necessary in an organic solvent to give 2-naphthylacetonitrile.Type: ApplicationFiled: May 25, 2022Publication date: September 8, 2022Applicant: API CORPORATIONInventors: Masaki NAGAHAMA, Daiki OKADO, Hirotsugu TANIIKE
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Publication number: 20220009880Abstract: High purity 2-naphthylacetonitrile with fewer impurities can be used as a starting material or intermediate for synthesizing various pharmaceutical products, agricultural chemicals, and chemical products, and a production method thereof. A high purity 2-naphthylacetonitrile having an HPLC purity of 2-naphthylacetonitrile of not less than 95 area %, and containing naphthalene compounds represented by the formulas (a)-(j) at a content of a predetermined area % or below. A method for producing high purity 2-naphthylacetonitrile, may include: subjecting 2?-acetonaphthone to a Willgerodt reaction in the presence of an additive where necessary, and hydrolyzing the obtained amide compound to give 2-naphthylacetic acid; and reacting the 2-naphthylacetic acid obtained in the subjecting, a halogenating agent and sulfamide in the presence of a catalyst as necessary in an organic solvent to give 2-naphthylacetonitrile.Type: ApplicationFiled: October 28, 2020Publication date: January 13, 2022Applicant: API CORPORATIONInventors: Masaki NAGAHAMA, Daiki OKADO, Hirotsugu TANIIKE
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Patent number: 11136287Abstract: The present invention provides an industrially-preferable method for safely producing N-benzyl-2-bromo-3-methoxypropionamide at a high yield but at low cost. The method for producing of the present invention includes: in sequence, an amidation process that causes diacrylic anhydride to react with benzylamine in a solvent to obtain N-benzylacrylamide; a bromination process that causes N-benzylacrylamide to react with bromine in a solvent to obtain N-benzyl-2,3-dibromopropionamide; and a methoxylation process that causes N-benzyl-2,3-dibromopropionamide to react with methanol in the presence of a base to obtain N-benzyl-2-bromo-3-methoxypropionamide.Type: GrantFiled: November 21, 2017Date of Patent: October 5, 2021Assignee: API CORPORATIONInventors: Masaki Nagahama, Kenta Saito
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Publication number: 20210188904Abstract: The present invention provides a method of industrially and safely producing lacosamide high in diastereomeric excess at a high yield and a low cost. Adopting a particular isomerization-crystallization condition makes it possible to a method of industrially and safely producing lacosamide high in diastereomeric excess at a high yield and a low cost. Additionally, an intermediate efficacious for producing lacosamide is provided.Type: ApplicationFiled: March 9, 2021Publication date: June 24, 2021Applicant: API CORPORATIONInventor: Masaki NAGAHAMA
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Patent number: 10975117Abstract: The present invention provides a method of industrially and safely producing lacosamide high in diastereomeric excess at a high yield and a low cost. Adopting a particular isomerization-crystallization condition makes it possible to a method of industrially and safely producing lacosamide high in diastereomeric excess at a high yield and a low cost. Additionally, an intermediate efficacious for producing lacosamide is provided.Type: GrantFiled: November 11, 2016Date of Patent: April 13, 2021Assignee: API CORPORATIONInventor: Masaki Nagahama
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Publication number: 20210078940Abstract: The present invention provides a method for industrially producing a highly pure aromatic nitrile compound and a highly pure aromatic carboxylic acid compound safely and highly efficiently at low costs. Compound (2) is subjected to Willgerodt reaction in the presence of an additive as necessary, and the obtained amide compound (3) is hydrolyzed and neutralized to give carboxylic acid compound (4). Carboxylic acid compound (4) is reacted with a halogenating agent in the presence of a catalyst as necessary in an organic solvent, and further reacted with an amidating agent, and the obtained amide compound (5) or (6) is reacted with a dehydrating agent to give nitrile compound (1). Alternatively, carboxylic acid compound (4) is reacted with a halogenating agent and a compound represented by the formula R6SO2R7 in the presence of a catalyst as necessary in an organic solvent to give nitrile compound (1).Type: ApplicationFiled: April 26, 2019Publication date: March 18, 2021Applicant: API CORPORATIONInventors: Masaki NAGAHAMA, Hideki OOMIYA, Daiki OKADO, Hirotsugu TANIIKE
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Patent number: 10815201Abstract: Production of pitavastatin calcium safely on an industrial scale with a high yield and high selectivity at low cost. A method of producing pitavastatin calcium including step (i) for acetalizing a compound represented by the formula (1) to give a compound represented by the formula (3), step (ii) for reacting a compound represented by the formula (3) with an acid to give a compound represented by the formula (4), and step (iii) for hydrolyzing a compound represented by the formula (4) and reacting same with a calcium compound.Type: GrantFiled: April 17, 2020Date of Patent: October 27, 2020Assignee: API CORPORATIONInventors: Naoyuki Watanabe, Takanobu Iura, Hideki Oomiya, Masaki Nagahama