Patents by Inventor Hiroyuki Nohira
Hiroyuki Nohira 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: 5281362Abstract: An optically active compound represented by the following formula (I): ##STR1## wherein R.sub.1 denotes an alkyl or alkoxy group having 1-18 carbon atoms; R.sub.2 denotes an alkyl group having 1-12 carbon atoms; A denotes ##STR2## X denotes and C* denotes an optically active asymmetric carbon atom. The optically active compound, when included as a component, provides a ferroelectric liquid crystal composition or device showing an improved electro-field response characteristic.Type: GrantFiled: February 12, 1992Date of Patent: January 25, 1994Assignee: Canon Kabushiki KaishaInventors: Hiroyuki Nohira, Takao Takiguchi, Takashi Iwaki, Takeshi Togano, Yoko Yamada, Shinichi Nakamura, Akira Sakaigawa
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Patent number: 5217644Abstract: A mesomorphic compound represented by the following formula (I): ##STR1## wherein R.sup.1 denotes analkyl group having 1-18 carbon atoms; R.sup.2 denotes an alkyl group having 1-12 carbon atoms; A and B respectively denote ##STR2## Z.sup.1 and Z.sup.2 respectively denote --H, 'CH.sub.3, --OCH.sub.3, --CN or halogen; m and n respectively denote 0, 1 or 2 and p denotes 1 or 2 with proviso that m+n+p =2 or 3; X denotes a single bond, ##STR3## denotes an asymmetric carbon atom.Type: GrantFiled: January 29, 1991Date of Patent: June 8, 1993Assignee: Canon Kabushiki KaishaInventors: Hiroyuki Nohira, Yoko Yamada, Shinichi Nakamura, Akira Sakaigawa, Yasumasa Tashiro, Yoshio Aoki
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Patent number: 5194177Abstract: An optically active compound represented by the following formula (I): ##STR1## wherein R.sub.1 denotes a linear or branched alkyl group having 1-18 carbon atoms optionally including one or non-neighboring two or more methylene groups which can be replaced with --X-- or ##STR2## with the proviso that X denotes O or S and Y denotes halogen; R.sub.2 denotes a linear alkyl group having 4-8 carbon atoms: and C* denotes an optically active asymmetric carbon atom. The mesomorphic compound is effective for providing a ferroelectric liquid crystal composition showing improved response characteristics and also effective for suppressing occurrence of reverse domain.Type: GrantFiled: January 21, 1992Date of Patent: March 16, 1993Assignee: Canon Kabushiki KaishaInventors: Hiroyuki Nohira, Takao Takiguchi, Takashi Iwaki, Takeshi Togano, Yoko Yamada, Shinichi Nakamura
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Patent number: 5191112Abstract: Optical resolution of (.+-.)-2-(3-benzoyl)-phenylpropionic acid is attained effeciently in high yield by the use of a specific optically active amine which is represented by the general formula [I]: ##STR1## wherein R.sup.1 either stands for a hydrogen atom, a chlorine atom, a bromine atom, a methyl group, or an isopropyl group or participates, as a divalent group, in forming a benzene ring in combination with two carbon atoms adjoining each other in a benzene ring to which the substituent, R.sup.1, is bonded, R.sup.2 stands for a lower alkyl group, a hydroxymethyl group, an .alpha.-hydroxybenzyl group, or a ##STR2## group (R.sup.3 standing for a hydrogen atom, a chlorine atom, a bromine atom, or a methyl group), n for 0 or 1, and * for the center of optical activity.Type: GrantFiled: August 24, 1990Date of Patent: March 2, 1993Assignee: Nissan Chemical Industries, Ltd.Inventors: Hiroyuki Nohira, Kazutaka Arai
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Patent number: 5171470Abstract: A bifunctional optically active liquid crystal intermediate compound represented by the following Formula (I): X--Y--C.sub.* H(M)--CH.sub.2 --OH is disclosed, wherein X represents CH.sub.2 .dbd.CH--, HOCH.sub.2 --CH.sub.2 --, HSCH.sub.2 --CH.sub.2 --, HOCH.sub.2 --, HOOC--, HOCH.sub.2 CH.dbd.CH--, CH.sub.3 CH(OH)-- or HOCH.sub.2 C.sub.* H(Z)--; Y represents --CH.sub.2).sub.n or --CH.sub.2 (.sub.m O).sub.l CH.sub.2 --, where n represents an integer of 1 to 18, m represents an integer of 1 to 12, and l represents an integer of 1 to 4; M and Z each represents halogen atom, an alkyl group or an alkoxy group, said halogen atom being selected from the group consisting of I, Cl, Br and F, and said alkyl group or alkoxy group having 1 to 8 carbon atoms; and the mark * represents an asymmetric carbon atom. A process for preparing the intermediate compound is also disclosed.Type: GrantFiled: August 7, 1990Date of Patent: December 15, 1992Assignees: Canon Kabushiki Kaisha, Hiroyuki NohiraInventors: Hiroyuki Nohira, Takahiro Ishizuka, Kazuo Yoshinaga
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Optically active compound, process for producing same and liquid crystal composition containing same
Patent number: 5126071Abstract: An optically active functional compound represented by the following formula (1) is disclosed: ##STR1## wherein R denotes an alkyl group having 1-14 carbon atoms; --X-- denotes ##STR2## Y denotes a single bond, ##STR3## or --O--; n=0, 1 or 2; and C* denotes an asymmetric carbon atom. The compound of the formula (1) may be produced through an optically active compound of the following formula (2) or (3): ##STR4## The compounds of the above formulas (1)-(3) are all characterized by a trifluoromethyl group providing a large spontaneous polarization attached to an asymmetric carbon atom.Type: GrantFiled: August 7, 1991Date of Patent: June 30, 1992Assignee: Canon Kabushiki KaishaInventors: Hiroyuki Nohira, Masanao Kamei, Hideki Kanazawa, Tetsuya Abe, Yoko Yamada, Yuko Etoh -
Patent number: 5098600Abstract: There is provided a liquid crystal compound represented by the following general formula (I), a liquid crystal composite including at least one kind of above liquid crystal compound and a liquid crystal device in which the liquid crystal composite is disposed between a pair of electrode substrates. ##STR1## In the above formula (I), R.sub.1 is a straight chain alkyl having 1-12 carbon atoms. R.sub.2 is a straight chain or branched chain alkyl, which may have a substituted radical, having 1-18 carbon atoms and in which one or more than two methylene, which do not adjoin, may be substituted by --Y--, ##STR2## --CH.dbd.CH--, or --C.vertline.C--. Y is O or S. A is --A.sub.1 -- or --A.sub.1 --A.sub.2 --, and B is --B.sub.1 -- or --B.sub.1 --B.sub.2 --. A.sub.1, A.sub.2, B.sub.1, and B.sub.2 each is selected from ##STR3## and a single bond. Z is hydrogen, halogen, cyano or methyl. X.sub.1 is a single bond when A is a single bond and is --CH.sub.2 O--, ##STR4## in other cases. n is 0 or 1, ##STR5## --OCH.sub.Type: GrantFiled: December 20, 1990Date of Patent: March 24, 1992Assignee: Canon Kabushiki KaishaInventors: Shinichi Nakamura, Yoko Yamada, Hiroyuki Nohira, Takao Takiguchi, Takashi Iwaki, Takeshi Togano
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Patent number: 5087728Abstract: A process for producing a carboxylic acid or an ester thereof represented by formula (I): ##STR1## wherein: R represents a hydrogen atom or a lower alkyl group; R.sup.1 represents a lower alkyl group; CH.sub.2 COOR.sup.3, wherein R.sup.3 represents a hydrogen atom or a lower alkyl group; or NHR.sup.4, wherein R.sup.4 represents a formyl group, an acetyl group, a benzoyl group, or a chloroacetyl group, andR.sup.2 represents a hydrogen atom, a lower alkyl group, or a phenyl group,which comprises hydrogenating an unsaturated compound represented by formula (II): ##STR2## wherein R, R.sup.1, and R.sup.2 are as defined above, in the presence of a rhodium or ruthenium complex catalyst having, as a ligand, BICHEP which means 2,2'-bis(dicyclohexylphoshino)-6,6'-dimethyl-1,1'-biphenyl represented by formula (III): ##STR3## is disclosed.Type: GrantFiled: July 11, 1990Date of Patent: February 11, 1992Assignee: Takasago International CorporationInventors: Hiroyuki Nohira, Hidemasa Takaya, Akira Miyashita
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Patent number: 5075031Abstract: A mesomorphic compound represented by the formula: ##STR1## wherein R.sub.1 denotes an alkyl group having 1-16 carbon atoms; R.sub.2 denotes an alkyl group having 2-10 carbon atoms; X denotes a single bond or --O--; Y denotes --OCH.sub.2 --, ##STR2## Z denotes a single bond, ##STR3## respectively and independently denote ##STR4## k, l and n are respectively 0, 1 or 2 satisfying the relation of k+l+n=2 or 3; C* denotes an asymmetric carbon atom. The mesomorphic compound, when added as a component, provides a liquid crystal composition showing an improved field respective characteristic or is effective in preventing occurrence of a reverse domain.Type: GrantFiled: December 20, 1989Date of Patent: December 24, 1991Assignee: Canon Kabushiki KaishaInventors: Hiroyuki Nohira, Takashi Kimura, Yoko Yamada, Kazushige Yamagishi
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Patent number: 5073306Abstract: An optically active, generally mesomorphic compound represented by the following formula (I): ##STR1## wherein R.sub.1 denotes an alkyl group having 1-18 carbon atoms, R.sub.2 denotes an alkyl group having 1-12 carbon atoms; X denotes a single bond, --O--, ##STR2## Y denotes a single bond, ##STR3## --CH.sub.2 O-- or --OCH.sub.2 --; Z denotes --OCH.sub.2 --, ##STR4## C* denotes an asymmetric carbon atom; k, m and n are respectively 0, 1 or 2 with proviso that k+m+n amounts to 2 or 3; and p is 1 or 2.Type: GrantFiled: July 25, 1989Date of Patent: December 17, 1991Assignee: Canon Kabushiki KaishaInventors: Hiroyuki Nohira, Masanao Kamei, Hideki Kanazawa, Yoko Yamada, Yuko Etoh
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Patent number: 5066826Abstract: A process for the racemization of optically active 4-phenylbutanoic acid esters which comprises treating optically active 4-phenylbutanoic acid esters of the general formula (1) ##STR1## wherein R.sup.1 represents a hydroxy group, a hydroxy group protected by vinyl ester, or a lower acyloxy group and R.sup.2 represents a lower alkyl group with a base selected from the group consisting of alkali metal alcoholates, alkali metal hydrides, and alkali metal amides is provided.Type: GrantFiled: September 26, 1990Date of Patent: November 19, 1991Assignee: Kuraray Company, Ltd.Inventors: Hiroyuki Nohira, Takashi Onishi, Kazuo Yamamoto, Noriaki Kumagai
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Patent number: 5021593Abstract: A ruthenium-optically active phosphine complex having, as a ligand, BICHEP which means 2,2'-bis(dicyclohexylphosphino)-6,6'-dimethyl-1,1'-biphenyl represented by formula (I): ##STR1## is disclosed, which can catalyze asymmetric syntheses, such as asymmetric hydrogenation, asymmetric isomerization, and asymmetric silylation, exhibiting excellent catalytic activity and providing high optical purity.Type: GrantFiled: July 11, 1990Date of Patent: June 4, 1991Assignee: Takasago International CorporationInventors: Hiroyuki Nohira, Hidemasa Takaya, Akira Miyashita
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Optically active compound, process for producing same and liquid crystal composition containing same
Patent number: 4999130Abstract: An optically active 2-cyano-2-methyl-alkanoic acid represented by the formula: ##STR1## is produced by optical resolution of the corresponding racemic mixture thereof with an optically active amine and is reduced to provide an optically active 2-cyano-2-methyl-1-alkanol represented by the formula: ##STR2## wherein R.sub.1 denotes an alkyl groups having 3-10 carbon atoms, R.sub.2 denotes an alkyl group having 2-10 carbon atoms and C* denotes an asymmetric carbon atom. These compounds are characterized by having a CN group with a large dipole moment directly attached to an asymmetric carbon atom and are effective for controlling the liquid crystal state of a liquid crystal composition when added thereto.Type: GrantFiled: August 27, 1990Date of Patent: March 12, 1991Assignees: Canon Kabushiki Kaisha, Yamakawa Chemical Industry Co., Ltd.Inventors: Hiroyuki Nohira, Takashi Kimura, Tetsuya Abe, Yoko Yamada, Kazuhige Yamagishi -
Patent number: 4978666Abstract: A novel (-)-optically active piperazine derivative of the formula: ##STR1## (wherein the mark of * indicates an optically active carbon) shows an increased cerebral circulation-improving effect as well as an enhanced safety.Type: GrantFiled: August 7, 1989Date of Patent: December 18, 1990Assignee: Nippon Chemiphar Co., Ltd.Inventors: Hiroyuki Nohira, Mitsuo Masaki, Masao Yamamoto
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Patent number: 4950772Abstract: Disclosed is a method of racemization of optically active tetrahydrofuran-2-carboxylic acid. (+)-Tetrahydrofuran-2-carboxylic acid is useful as a side chain intermediate of the antibiotics of penem series, and is prepared by optical resolution of racemic compound. The remaining (+)-isomer should be racemized and reused as the material for further optical resolution. The racemization can be, in accordance with the present invention, carried out by heating the optically active tetrahydrofuran-2-carboxylic acid to a temperature of 100.degree. C. or higher in the presence of a strong base.Type: GrantFiled: October 31, 1989Date of Patent: August 21, 1990Assignee: Yamakawa Chemical Industry Co., Ltd.Inventors: Hiroyuki Nohira, Shoko Takebayashi, Atsushi Yuzawa, Masami Yajima
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Patent number: 4918213Abstract: An optically active, generally mesomorphic compound represented by the following formula (I): ##STR1## wherein R.sub.1 denotes an alkyl group having 1-18 carbon atoms, R.sub.2 denotes an alkyl group having 1-12 carbon atoms; X denotes a single bond, --O--, ##STR2## Y denotes a single bond, ##STR3## --CH.sub.2 O-- or --OCH.sub.2 --; Z denotes --OCH.sub.2 --, ##STR4## respectively denotes ##STR5## C* denotes an asymmetric carbon atom; k, m and n are respectively 0, 1 or 2 with proviso that k+m+n amounts to 2 or 3; and p is 1 or 2.Type: GrantFiled: July 25, 1988Date of Patent: April 17, 1990Assignee: Canon Kabushiki KaishaInventors: Hiroyuki Nohira, Masanao Kamei, Hideki Kanazawa, Yoko Yamada, Yuko Etoh
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Patent number: 4917817Abstract: An optically active functional compound represented by the following formula (1) is disclosed: ##STR1## wherein R denotes an alkyl group having 1-14 carbon atoms; -X- denotes ##STR2## denotes a single bond, ##STR3## n=0, 1 or 2; and C* denotes an asymmetric carbon atom. The compound of the formula (1) may be produced through an optically active compound of the following formula (2) or (3): ##STR4## The compounds of the above formulas (1)-(3) are all characterized by a trifluoromethyl group providing a large spontaneous polarization attached to an asymmetric carbon atom.Type: GrantFiled: July 21, 1988Date of Patent: April 17, 1990Assignee: Canon Kabushiki KaishaInventors: Hiroyuki Nohira, Masanao Kamei, Hideki Kanazawa, Tetsuya Abe, Yoko Yamada, Yuko Etoh
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Patent number: 4904822Abstract: A process for the optical resolution of (.+-.)-2-hydroxy-4-phenylbutanoic acid which comprises treating (.+-.)-2-hydroxy-4-phenylbutanoic acid with an optically active 1-(p-tolyl)ethylamine or an optically active N-(2-hydroxy)ethyl-.alpha.-methylbenzylamine as a resolving agent is provided by the present invention.According to the invention, (-)-2-hydroxy-4-phenylbutanoic acid, which is useful as a starting substance for the synthesis of angiotensin converting enzyme-inhibiting pharmaceuticals, can especially be obtained in a highly pure state and in a high yield.Type: GrantFiled: February 9, 1989Date of Patent: February 27, 1990Assignee: Kuraray Co., Ltd.Inventors: Hiroyuki Nohira, Shinichi Yoshida
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Patent number: 4904410Abstract: An optically active mesomorphic compound is represented by the following formula (I): ##STR1## wherein R.sub.1 and R.sub.2 are respectively an alkyl group having 1 to 16 carbon atoms, and C* denotes an asymmetric carbon atom. The mesomorphic compound has a fluorine atom directly connected to the asymmetric carbon atom and is effectively used as a liquid crystal component providing an increased spontaneous polarization and an improved responsiveness.Type: GrantFiled: March 28, 1988Date of Patent: February 27, 1990Assignee: Canon Kabushiki KaishaInventors: Hiroyuki Nohira, Masanao Kamei, Shinichi Nakamura, Takashi Iwaki, Kazuharu Katagiri, Yoko Yamada
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Patent number: 4892675Abstract: An optically active polymer comprises recurring units of the following formula: ##STR1## wherein l is an integer of 5-1000, n is an integer of 1-3, m is an integer of 2-20, and * denotes the location of an asymmetric center. The optically active polymer has a good mutual solubility with a low-molecular weight mesomorphic compound and is easily mixed with the latter to provide a uniform liquid crystal composition which shows ferroelectricity and better film formability and stability than the low-molecular weight mesamorphic compound alone.Type: GrantFiled: June 7, 1988Date of Patent: January 9, 1990Assignees: Canon Kabushiki Kaisha, Nissan Chemical Industries, Ltd.Inventors: Hiroyuki Nohira, Kazutaka Arai, Kazuo Yoshinaga