Patents by Inventor Shigeru Mitsuhashi
Shigeru Mitsuhashi 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: 6403804Abstract: Disclosed is a process for preparing an optically active oxazolidinone derivative comprising allowing hydrazine to react on an optically active ester having a hydroxyl group at the 3-position which is represented by formula (II): wherein R1 represents a lower alkyl group having 1 to 4 carbon atoms, a phenyl group, a methoxymethyl group, a benzyloxymethyl group, a benzyloxycarbonylaminomethyl group which may have a substituent or substituents on the benzene ring thereof, an acylaminomethyl group having 3 to 10 carbon atoms, or an alkyloxycarbonylaminomethyl group having 3 to 6 carbon atoms; R2 and R3, which may be the same or different, each represent a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, a phenyl group, an acetylaminomethyl group, a benzoylaminomethyl group, or a benzyl group; and * indicates an asymmetric carbon atom, and subjecting the resulting hydrazide to Curtius rearrangement.Type: GrantFiled: December 7, 1999Date of Patent: June 11, 2002Assignee: Takasago International CorporationInventors: Kenzo Sumi, Takashi Imai, Shigeru Mitsuhashi, Hideki Nara, Takashi Miura
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Patent number: 6093345Abstract: An optically active compound represented by formula (I): wherein A represents ##STR1## wherein R.sup.2 represents an alkyl group having from 8 to 12 carbon atoms; R.sup.1 represents a straight chain alkyl group having from 2 to 5 carbon atoms; X represents a fluorine atom or a methyl group; n represents 1 or 2; m represents an integer of from 0 to 3; and C* represents an asymmetric carbon atom, and a liquid crystal composition containing the same are disclosed. The compound exhibits large spontaneous polarization and low viscosity and, when added to an achiral base liquid crystal composition, induces a chiral nematic phase in which the helical pitch has small temperature dependence.Type: GrantFiled: July 14, 1993Date of Patent: July 25, 2000Assignee: Takasago International CorporationInventors: Shigeru Mitsuhashi, Yoshimasa Matsushima, Takashi Imai, Kiichi Mori, Mamoru Yamada, Hiroshi Sugiyama, Misao Yagi, Hitoshi Kondo, Toshimitsu Hagiwara
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Patent number: 5837877Abstract: A process for preparing optically active 4-hydroxy-2-pyrrolidone comprising asymmetrically hydrogenating an N-substituted-4-amino-3-oxobutanoic ester represented by formula (I): ##STR1## wherein R.sup.1 represents a benzyloxycarbonyl group, the benzene ring of which may be substituted; and R.sup.2 represents a lower alkyl group having 1 to 4 carbon atoms, in the presence of a ruthenium-optically active phosphine complex as a catalyst to obtain an optically active N-substituted-4-amino-3-hydroxybutanoic ester, deblocking, and cyclizing the ester. A series of the reactions can be carried out in one pot.Type: GrantFiled: January 29, 1997Date of Patent: November 17, 1998Assignee: Takasago International CorporationInventors: Shigeru Mitsuhashi, Hidenori Kumobayashi
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Patent number: 5777103Abstract: A process for producing cyclohexylazetidinone expressed by the formula(IV) comprises condensing the magnesium enolate compound expressed by the formula (II) with acyloxyazetidinone expressed by the formula (III), wherein Me is a methyl group; R.sup.1 is a hydroxyl-protecting group, R.sup.2 is an acyl group, and X is a halogen atom.Type: GrantFiled: February 28, 1997Date of Patent: July 7, 1998Assignee: Takasago International CorporationInventors: Takaji Matsumoto, Toshiyuki Murayama, Shigeru Mitsuhashi, Takashi Miura
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Patent number: 5430171Abstract: T-butyl (R)-(-)-4-cyano-3-hydroxybutyrate having an optical purity of 99%ee or higher and a process for producing the same are disclosed, the process comprising cyanogenation of a t-butyl (S)-(-)-4-halogeno-3-hydroxybutyrate obtained by enantioselective hydrogenation of a t-butyl 4-halogenoacetoacetate. Recrystallization of the resulting crude product gives the optically active compound with high optical purity.Type: GrantFiled: July 11, 1994Date of Patent: July 4, 1995Assignee: Takasago International CorporationInventors: Shigeru Mitsuhashi, Kazutoshi Sakurai, Hidenori Kumobayashi
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Patent number: 5349107Abstract: Disclosed herein is a process for producing a .gamma.-hydroxyketone (2), which comprises asymmetrically hydrogenating a .gamma.-diketone (1) in the presence of a ruthenium-optically active phosphine complex as a catalyst ##STR1## wherein R.sup.1 and R.sup.2 mean individually an alkyl or phenyl group which may have a substituent group. According to the invention, optically active .gamma.-hydroxyketones useful in synthesizing optically active moiety in, biodegradable polymers, perfumes, intermediates for synthesizing medicines and the like can be efficiently prepared.Type: GrantFiled: October 1, 1993Date of Patent: September 20, 1994Assignee: Takasago International CorporationInventors: Seiji Watanabe, Shigeru Mitsuhashi, Hidenori Kumobayashi
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Patent number: 5286883Abstract: A (3R,5S)-3,5,6-trihydroxyhexanoic acid derivative and a process of producing the (3R,5S)-3,5,6-trihydroxyhexanoic acid derivative which comprises the step of enantioselectively hydrogenating an (S)-5,6-dihydroxy-3-oxohexanoic acid derivative with a specific ruthenium-optically active phosphine complex represented as a catalyst are disclosed. The (3R,5S)-3,5,6-trihydroxyhexanoic acid derivative which is a useful compound capable of being easily converted into a lactone moiety, which is the active part of an inhibitor on HMG-CoA reductase, can be easily and efficiently obtained under a mild reaction condition with a high selectivity for the syn-diol form.Type: GrantFiled: November 13, 1992Date of Patent: February 15, 1994Assignee: Takasago International CorporationInventors: Kazutoshi Sakurai, Shigeru Mitsuhashi, Hidenori Kumobayashi
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Patent number: 5275756Abstract: A fluorine-containing optically active compound represented by formula (I): ##STR1## wherein R.sub.1 represents a straight chain alkyl or alkoxy group having from 6 to 14 carbon atoms or a 4-alkylphenyl or 4-alkoxyphenyl group having from 8 to 12 carbon atoms; R.sub.2 represents a straight chain alkyl group having from 1 to 8 carbon atoms; C.sup.* represents an asymmetric carbon atoms; and X represents a hydrogen atom or a fluorine atom, provided that X represents a fluorine atom when R.sub.1 contains a phenyl group, and a liquid crystal composition containing the same are disclosed. The compound (I) has large spontaneous polarization and low viscosity to achieve a fast response time. In the N.sup.* phase of the compound (I), the helical pitch has small temperature dependence.Type: GrantFiled: July 31, 1991Date of Patent: January 4, 1994Assignee: Takasago International CorporationInventors: Akio Yamaguchi, Shigeru Mitsuhashi, Mamoru Yamada, Minzo Sakaguchi, Hiroshi Sugiyama, Hiroko Konuma, Hitoshi Kondo, Toshimitsu Hagiwara
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Patent number: 5049308Abstract: A liquid crystal compound represented by formula: ##STR1## wherein R.sub.1 represents a straight chain alkyl group having from 4 to 18 carbon atoms; R.sub.2 represents a straight chain alkyl group having from 2 to 6 carbon atoms or a branched alkyl group having from 3 to 6 atoms and having a methyl group as a side chain; and m and n each represents 1 or 2, is disclosed.The liquid crystal compound of formula (I) is optically and electrically stable and exhibits fast electro-optical switching in image display.Type: GrantFiled: June 27, 1989Date of Patent: September 17, 1991Assignee: Takasago International CorporationInventors: Shigeru Mitsuhashi, Hitoshi Kondo, Tetsuharu Okazaki, Shinji Endoh, Hiroko Kudo, Akio Yamaguchi, Haruki Tsuruta, Susumu Akutagawa
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Patent number: 4886623Abstract: A liquid crystal compound represented by formula: ##STR1## wherein R.sub.1 represents a straight chain alkyl group having from 4 to 18 carbon atoms; R.sub.2 represents a straight chain alkyl group having from 2 to 6 carbon atoms or a branched alkyl group having from 3 to 6 atoms and having a methyl group as a side chain; and m and n each represents 1 or 2, is disclosed.The liquid crystal compound of formula (I) is optically and electrically stable and exhibits fast electro-optical switching in image display.Type: GrantFiled: December 23, 1987Date of Patent: December 12, 1989Assignee: Takasago International CorporationInventors: Shigeru Mitsuhashi, Hitoshi Kondo, Tetsuharu Okazaki, Shinji Endoh, Hiroko Kudo, Akio Yamaguchi, Haruki Tsuruta, Susumu Akutagawa
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Patent number: 4520212Abstract: Myrcenol is produced in an effecient, high yield and economical process by deaminating 7-hydroxygeranyl dialkylamine or 7-hydroxyneryl dialkylamine with a specific palladium-phosphine-cation complex catalyst represented by the formula[<.cndot.:PdL].sup.+ X.sup.-wherein <.cndot.: represents .eta.-allyl, L represents a tertiary phosphine, and X represents a counter anion.Type: GrantFiled: December 21, 1983Date of Patent: May 28, 1985Assignee: Takasago Perfumery Co., Ltd.Inventors: Shigeru Mitsuhashi, Hidenori Kumobayashi, Susumu Akutagawa