Patents by Inventor Masato Murai
Masato Murai 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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Publication number: 20240150292Abstract: The present invention aims to provide a method for producing a (2S,5R)-5-(protected oxyamino)-piperidine-2-carboxylic acid derivative at a low cost that can be performed under mild reaction conditions not requiring a facility at an extremely low temperature, is safer, can control the quality of the desired product with ease, and shows good workability in the site of production. A method for producing a compound represented by the formula (2) wherein PG1 is an amino-protecting group, PG2 is an amino-protecting group, PG3 is a hydroxyl-protecting group, LG is a leaving group, and R is a hydrocarbon group having 1-8 carbon atoms and optionally having substituent(s), including a step of reacting a compound represented by the formula (1): wherein each symbol is as defined above, with a hydroxylamine derivative represented by the formula PG2NHOPG3 wherein each symbol is as defined above, in the presence of a base in a solvent.Type: ApplicationFiled: December 20, 2023Publication date: May 9, 2024Applicant: API CORPORATIONInventors: Masato MURAI, Jun TAKEHARA, Daiki OKADO
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Patent number: 11897844Abstract: The present invention aims to provide a method for producing a (2S,5R)-5-(protected oxyamino)-piperidine-2-carboxylic acid derivative at a low cost that can be performed under mild reaction conditions not requiring a facility at an extremely low temperature, is safer, can control the quality of the desired product with ease, and shows good workability in the site of production. A method for producing a compound represented by the formula (2): wherein PG1 is an amino-protecting group, PG2 is an amino-protecting group, PG3 is a hydroxyl-protecting group, LG is a leaving group, and R is a hydrocarbon group having 1-8 carbon atoms and optionally having substituent(s), including a step of reacting a compound represented by the formula (1): wherein each symbol is as defined above, with a hydroxylamine derivative represented by the formula PG2NHOPG3 wherein each symbol is as defined above, in the presence of a base in a solvent.Type: GrantFiled: September 24, 2019Date of Patent: February 13, 2024Assignee: API CORPORATIONInventors: Masato Murai, Jun Takehara, Daiki Okado
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Publication number: 20240002340Abstract: A method for producing a compound represented by the formula (1): wherein LG is a leaving group, PG1 is an amino-protecting group, and R is a hydrocarbon group having 1-8 carbon atoms and optionally having substituent(s), comprising reacting a compound represented by the formula (6): with an amino group protecting agent to obtain a compound represented by the formula (7): or a salt thereof; reacting the aforementioned compound represented by the formula (7) with a lactonization agent to obtain a compound represented by the formula (8): reacting the aforementioned compound represented by the formula (8) with an esterification agent to obtain a compound represented by the formula (9): and reacting the aforementioned compound represented by the formula (9) with a leaving group introduction agent.Type: ApplicationFiled: September 7, 2023Publication date: January 4, 2024Applicant: API CORPORATIONInventors: Masato MURAI, Jun TAKEHARA, Daiki OKADO
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Patent number: 11802258Abstract: A fragrance precursor represented by formula (1): wherein R1 represents a hydrogen atom, an alkyl group having a carbon number of 1 to 12, a hydroxy group, a methoxy group or an ethoxy group R2 represents a single bond, an alkylene group having a carbon number of 1 to 2, which may have a substituent, or a vinylene group which may have a substituent; and R3 represents a residue resulting from removal of one hydrogen atom of a hydroxy group from a fragrance alcohol having a carbon number of 5 to 20 or a phenol which may have a substituent.Type: GrantFiled: September 21, 2018Date of Patent: October 31, 2023Assignee: TAKASAGO INTERNATIONAL CORPORATIONInventors: Tadahide Hatakeyama, Shinya Yamada, Masato Murai, Takahiro Ishikawa
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Publication number: 20230192596Abstract: A method for producing acetaminophen may include causing p-nitrophenol to undergo an acetamination reaction to produce the acetaminophen, by passing a solution containing the p-nitrophenol through a column packed with a catalyst while also passing an acetylating agent and hydrogen through the column. The catalyst may be a supported metal catalyst in which a metal element is supported on a synthetic adsorbent, and a reaction temperature of the acetamination reaction is 0° C. to 60° C., and a reaction pressure of the acetamination reaction is 0.1 MPa to 1 MPa. With the method, it is possible to continuously produce acetaminophen safely and inexpensively with high selectivity and good yield, at a low reaction temperature and a low reaction pressure.Type: ApplicationFiled: May 14, 2021Publication date: June 22, 2023Applicant: API CORPORATIONInventors: Masato MURAI, Hirotsugu TANIIKE, Yurie KOBA
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Publication number: 20230180804Abstract: A method for obscuring or masking the odor of p-cresol using olfactory receptor antagonism without affecting the flavor of a food or beverage is provided. The method includes the use of a specific concentration of ambrettolide, isoambrettolide, pentalide, muscone, civetone, ?-2-decenolactone, cinnamic aldehyde, (3-caryophyllene oxide, sclareolide, and ethyl maltol in a food or beverage. A citral-containing product containing one or more of ambrettolide, isoambrettolide, pentalide, muscone, civetone, ?-2-decenolactone, cinnamic aldehyde, (3-caryophyllene oxide, sclareolide, and ethyl maltol, and a flavor composition are provided.Type: ApplicationFiled: May 14, 2021Publication date: June 15, 2023Applicant: TAKASAGO INTERNATIONAL CORPORATIONInventors: Taichi YOSHIDA, Azusa MIKI, Masato MURAI
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Publication number: 20220411884Abstract: The present invention relates to a screening method for materials suppressing one or more offensive odors selected from the group consisting of a 1-octen-3-one odor, a 1,5-octadien-3-one odor, a 1-octen-3-ol odor and a 1,5-octadien-3-ol odor, an offensive odor-suppressing composition for reducing the offensiveness of age-related body odors and/or underarm odors, as well as a flavor composition for reducing off-flavors derived from food and beverage products. By using the screening method of the present invention, candidate substances for materials suppressing a 1-octen-3-one odor, a 1,5-octadien-3-one odor, a 1-octen-3-ol odor and a 1,5-octadien-3-ol odor can be selected respectively from among many test substances.Type: ApplicationFiled: October 30, 2020Publication date: December 29, 2022Applicant: Takasago International CorporationInventors: Azusa MIKI, Masato MURAI, Ikuo TERADA
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Publication number: 20220034866Abstract: The present invention relates to a method for screening a candidate substance for an unpleasant odor masking agent from among test substances using an olfactory receptor that is responsive to an unpleasant odor-causing substance. The screening method of the present invention includes the steps of: adding a test substance and an unpleasant odor-causing substance to an olfactory receptor polypeptide selected from the group consisting of OR2L3 and polypeptides which comprise an amino acid sequence having at least 80% identity to an amino acid sequence of OR2L3 and are responsive to the unpleasant odor-causing substance; measuring a response of the olfactory receptor polypeptide to the unpleasant odor-causing substance; and identifying the test substance that suppresses the response of the olfactory receptor polypeptide as a candidate substance for the unpleasant odor masking agent based on the measured response.Type: ApplicationFiled: July 27, 2021Publication date: February 3, 2022Applicant: Takasago International CorporationInventors: Masato MURAI, Ikuo TERADA
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Publication number: 20220031901Abstract: The present invention relates to a fragrance composition containing a fragrance component which suppresses response strength of at least one olfactory receptor polypeptide, which is selected from the group consisting of OR2L3 and polypeptides that comprise an amino acid sequence having at least 80% identity to an amino acid sequence of OR2L3 and are responsive to an unpleasant odor-causing substance, to the unpleasant odor-causing substance. According to a preferred embodiment of the present invention, an unpleasant odor masking composition containing, as active components, at least one antagonist against an olfactory receptor OR2L3 and a specific component among fragrances which do not exert the effect of suppressing the response of OR2L3, is provided. According to a preferred embodiment of the present invention, unpleasantness caused by at least one unpleasant odor selected from the group consisting of fecal odor, body odor, tobacco odor, breath odor and musty odor can be reduced.Type: ApplicationFiled: July 27, 2021Publication date: February 3, 2022Applicant: Takasago International CorporationInventors: Hisashi MIHARA, Yukari KUWAHARA, Masato MURAI, Tsuyoshi KOBAYASHI, Kenya ISHIDA
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Publication number: 20210403427Abstract: The present invention aims to provide a method for producing a (2S,5R)-5-(protected oxyamino)-piperidine-2-carboxylic acid derivative at a low cost that can be performed under mild reaction conditions not requiring a facility at an extremely low temperature, is safer, can control the quality of the desired product with ease, and shows good workability in the site of production. A method for producing a compound represented by the formula (2): wherein PG1 is an amino-protecting group, PG2 is an amino-protecting group, PG3 is a hydroxyl-protecting group, LG is a leaving group, and R is a hydrocarbon group having 1-8 carbon atoms and optionally having substituent(s), including a step of reacting a compound represented by the formula (1): wherein each symbol is as defined above, with a hydroxylamine derivative represented by the formula PG2NHOPG3 wherein each symbol is as defined above, in the presence of a base in a solvent.Type: ApplicationFiled: September 24, 2019Publication date: December 30, 2021Applicant: API CORPORATIONInventors: Masato MURAI, Jun TAKEHARA, Daiki OKADO
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Publication number: 20210348081Abstract: A method for releasing an aldehyde or ketone of formula (2) by allowing a hydrolase to act on a compound of formula (1) is disclosed. The compound of formula (1) is used as a flavor or fragrance precursor.Type: ApplicationFiled: June 28, 2021Publication date: November 11, 2021Applicant: TAKASAGO INTERNATIONAL CORPORATIONInventors: Shinya YAMADA, Tadahide HATAKEYAMA, Takahiro ISHIKAWA, Masato MURAI
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Publication number: 20210214644Abstract: A fragrance precursor represented by formula (1): wherein R1 represents a hydrogen atom, an alkyl group having a carbon number of 1 to 12, a hydroxy group, a methoxy group or an ethoxy group R2 represents a single bond, an alkylene group having a carbon number of 1 to 2, which may have a substituent, or a vinylene group which may have a substituent; and R3 represents a residue resulting from removal of one hydrogen atom of a hydroxy group from a fragrance alcohol having a carbon number of 5 to 20 or a phenol which may have a substituent.Type: ApplicationFiled: September 21, 2018Publication date: July 15, 2021Applicant: TAKASAGO INTERNATIONAL CORPORATIONInventors: Tadahide HATAKEYAMA, Shinya YAMADA, Masato MURAI, Takahiro ISHIKAWA
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Patent number: 10703719Abstract: A method for producing (2S,5S)/(2R,5R)-5-hydroxypiperidine-2-carboxylic acid represented by the formula (10) below: the method including removing the protecting group from the hydroxyl group in a compound represented by formula (7) below: (wherein P represents a protecting group, R3 represents an alkyl group containing 1 to 4 carbon atoms, and A represents an alkyl group containing 1 to 10 carbon atoms, an aryl group containing 6 to 12 carbon atoms, an alkyloxy group containing 1 to 4 carbon atoms, or an aralkyloxy group containing 7 to 20 carbon atoms) to synthesize a compound represented by formula (8) below: (wherein R3 represents an alkyl group containing 1 to 4 carbon atoms, and A represents an alkyl group containing 1 to 10 carbon atoms, an aryl group containing 6 to 12 carbon atoms, an alkyloxy group containing 1 to 4 carbon atoms, or an aralkyloxy group containing 7 to 20 carbon atoms).Type: GrantFiled: April 27, 2018Date of Patent: July 7, 2020Assignee: API CORPORATIONInventors: Jun Takehara, Masato Murai, Takashi Ohtani, Tomoko Maeda, Tsugihiko Hidaka
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Publication number: 20190338216Abstract: The invention relates to a method for releasing an aldehyde or ketone of formula (2) by allowing a hydrolase to act on a compound of formula (1). The compound of formula (1) is used as a flavor or fragrance precursor. In formula (1), each of R1, R2 and R3 independently represents a hydrogen atom, an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent, an alkenyl group which may have a substituent, an aryl group which may have a substituent, or an aralkyl group which may have a substituent. R1 and R2 or R1 and R3 may form a ring. Ar represents an aryl group which may have a substituent. In formula (2), R1, R2 and R3 have the same definitions as those in formula (1).Type: ApplicationFiled: January 19, 2018Publication date: November 7, 2019Applicant: TAKASAGO INTERNATIONAL CORPORATIONInventors: Shinya YAMADA, Tadahide HATAKEYAMA, Takahiro ISHIKAWA, Masato MURAI
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Patent number: 10370330Abstract: A method for producing (2S,5S)/(2R,5R)-5-hydroxypiperidine-2-carboxylic acid represented by the formula (10) below: the method comprising the step of removing the protecting group from the hydroxyl group in a compound represented by the formula (7) below: (wherein P represents a protecting group, R3 represents an alkyl group containing 1 to 4 carbon atoms, and A represents an alkyl group containing 1 to 10 carbon atoms, an aryl group containing 6 to 12 carbon atoms, an alkyloxy group containing 1 to 4 carbon atoms, or an aralkyloxy group containing 7 to 20 carbon atoms) to synthesize a compound represented by the formula (8) below: (wherein R3 represents an alkyl group containing 1 to 4 carbon atoms, and A represents an alkyl group containing 1 to 10 carbon atoms, an aryl group containing 6 to 12 carbon atoms, an alkyloxy group containing 1 to 4 carbon atoms, or an aralkyloxy group containing 7 to 20 carbon atoms).Type: GrantFiled: April 27, 2018Date of Patent: August 6, 2019Assignee: API CORPORATIONInventors: Jun Takehara, Masato Murai, Takashi Ohtani, Tomoko Maeda, Tsugihiko Hidaka
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Publication number: 20180244620Abstract: A method for producing (2S,5S)/(2R,5R)-5-hydroxypiperidine-2-carboxylic acid represented by the formula (10) below: the method comprising the step of removing the protecting group from the hydroxyl group in a compound represented by the formula (7) below: (wherein P represents a protecting group, R3 represents an alkyl group containing 1 to 4 carbon atoms, and A represents an alkyl group containing 1 to 10 carbon atoms, an aryl group containing 6 to 12 carbon atoms, an alkyloxy group containing 1 to 4 carbon atoms, or an aralkyloxy group containing 7 to 20 carbon atoms) to synthesize a compound represented by the formula (8) below: (wherein R3 represents an alkyl group containing 1 to 4 carbon atoms, and A represents an alkyl group containing 1 to 10 carbon atoms, an aryl group containing 6 to 12 carbon atoms, an alkyloxy group containing 1 to 4 carbon atoms, or an aralkyloxy group containing 7 to 20 carbon atoms).Type: ApplicationFiled: April 27, 2018Publication date: August 30, 2018Applicant: API CORPORATIONInventors: Jun TAKEHARA, Masato MURAI, Takashi OHTANI, Tomoko MAEDA, Tsugihiko HIDAKA
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Publication number: 20180244619Abstract: A method for producing (2S,5S)/(2R,5R)-5-hydroxypiperidine-2-carboxylic acid represented by the formula (10) below: the method including removing the protecting group from the hydroxyl group in a compound represented by formula (7) below: (wherein P represents a protecting group, R3 represents an alkyl group containing 1 to 4 carbon atoms, and A represents an alkyl group containing 1 to 10 carbon atoms, an aryl group containing 6 to 12 carbon atoms, an alkyloxy group containing 1 to 4 carbon atoms, or an aralkyloxy group containing 7 to 20 carbon atoms) to synthesize a compound represented by formula (8) below: (wherein R3 represents an alkyl group containing 1 to 4 carbon atoms, and A represents an alkyl group containing 1 to 10 carbon atoms, an aryl group containing 6 to 12 carbon atoms, an alkyloxy group containing 1 to 4 carbon atoms, or an aralkyloxy group containing 7 to 20 carbon atoms).Type: ApplicationFiled: April 27, 2018Publication date: August 30, 2018Applicant: API CORPORATIONInventors: Jun TAKEHARA, Masato MURAI, Takashi OHTANI, Tomoko MAEDA, Tsugihiko HIDAKA
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Patent number: 9988351Abstract: A method for producing (2S,5S)/(2R,5R)-5-hydroxypiperidine-2-carboxylic acid represented by the formula (10) below: the method including removing the protecting group from the hydroxyl group in a compound represented by formula (7) below: (wherein P represents a protecting group, R3 represents an alkyl group containing 1 to 4 carbon atoms, and A represents an alkyl group containing 1 to 10 carbon atoms, an aryl group containing 6 to 12 carbon atoms, an alkyloxy group containing 1 to 4 carbon atoms, or an aralkyloxy group containing 7 to 20 carbon atoms) to synthesize a compound represented by formula (8) below: (wherein R3 represents an alkyl group containing 1 to 4 carbon atoms, and A represents an alkyl group containing 1 to 10 carbon atoms, an aryl group containing 6 to 12 carbon atoms, an alkyloxy group containing 1 to 4 carbon atoms, or an aralkyloxy group containing 7 to 20 carbon atoms).Type: GrantFiled: September 15, 2017Date of Patent: June 5, 2018Assignee: API CORPORATIONInventors: Jun Takehara, Masato Murai, Takashi Ohtani, Tomoko Maeda, Tsugihiko Hidaka
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Patent number: 9981984Abstract: The present invention aims to provide a method for purifying cis-5-hydroxy-2-piperidinecarboxylic acid with high purity, and a method for producing its derivative. The present invention provides a method for producing a cis-5-hydroxy-2-piperidinecarboxylic acid derivative, which method comprises a step of converting cis-5-hydroxy-2-piperidinecarboxylic acid into a compound(s) of Formula (1) and/or Formula (2) (wherein R1 represents a protective group for an amino group, and R2 represents a C1-C6 alkyl group), and a method for purifying cis-5-hydroxy-2-piperidinecarboxylic acid.Type: GrantFiled: December 19, 2013Date of Patent: May 29, 2018Assignee: API CorporationInventors: Tomoko Maeda, Hisatoshi Uehara, Yasuyo Saito, Masato Murai
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Publication number: 20180002286Abstract: A method for producing (2S,5S)/(2R,5R)-5-hydroxypiperidine-2-carboxylic acid represented by the formula (10) below: the method including removing the protecting group from the hydroxyl group in a compound represented by formula (7) below: (wherein P represents a protecting group, R3 represents an alkyl group containing 1 to 4 carbon atoms, and A represents an alkyl group containing 1 to 10 carbon atoms, an aryl group containing 6 to 12 carbon atoms, an alkyloxy group containing 1 to 4 carbon atoms, or an aralkyloxy group containing 7 to 20 carbon atoms) to synthesize a compound represented by formula (8) below: (wherein R3 represents an alkyl group containing 1 to 4 carbon atoms, and A represents an alkyl group containing 1 to 10 carbon atoms, an aryl group containing 6 to 12 carbon atoms, an alkyloxy group containing 1 to 4 carbon atoms, or an aralkyloxy group containing 7 to 20 carbon atoms).Type: ApplicationFiled: September 15, 2017Publication date: January 4, 2018Applicant: API CORPORATIONInventors: Jun TAKEHARA, Masato MURAI, Takashi OHTANI, Tomoko MAEDA, Tsugihiko HIDAKA