Patents by Inventor Susumu Akutagawa
Susumu Akutagawa 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: 5352763Abstract: An optically active oligomer obtained by polycondensation of an (R)-3-hydroxyalkanoic acid alkyl ester and at least one of a diol, a diamine and an amino alcohol and an optically active polymer obtained by copolymerization of said oligomer and a monomer selected from diisocyanic acid esters, dicarboxylic acid derivatives, and dichlorosilanes are disclosed. Novel functional polymers with biodegradability and hydrolyzability are produced with industrial advantage.Type: GrantFiled: January 15, 1993Date of Patent: October 4, 1994Assignee: Takasago International CorporationInventors: Akio Yamaguchi, Yoji Hori, Takashi Imai, Motoki Suzuki, Susumu Akutagawa
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Patent number: 5264547Abstract: An optically active 7-substituted-1,4-dioxepan-5-one derivative represented by the general formula (I): ##STR1## wherein R represents an alkyl group having from 1 to 5 carbon atoms; and * means an asymmetric carbon atom, is disclosed. An optically active polymer represented by formula (II): ##STR2## wherein R and * are as defined above; and n is an integer of 25 or more, obtained by ring opening polymerization of the optically active 7-substituted-1,4-dioxepan-5-one derivative represented by formula (I) is also disclosed. A process for producing the optically active polymer represented by formula (II) is further disclosed, comprising subjecting an optically active 7-substituted-1,4-dioxepan-5-one derivative represented by formula (I) to ring opening polymerization in the presence of at least one catalyst selected from the group consisting of (i) an organotin compound, (ii) an organoaluminum compound and water, and (iii) an organozinc compound and water.Type: GrantFiled: March 2, 1993Date of Patent: November 23, 1993Assignee: Takasago International CorporationInventors: Akio Yamaguchi, Yoji Hori, Susumu Akutagawa
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Patent number: 5221755Abstract: An optically active 7-substituted-1,4-dioxepan-5-one derivative represented by the general formula (I): ##STR1## wherein R represents an alkyl group having from 1 to 5 carbon atoms; and * means an asymmetric carbon atom, is disclosed. An optically active polymer represented by formula (II): ##STR2## wherein R and * are as defined above; and n is an integer of 25 or more, obtained by ring opening polymerization of the optically active 7-substituted-1,4-dioxepan-5-one derivative represented by formula (I) is also disclosed. A process for producing the optically active polymer represented by formula (II) is further disclosed, comprising subjecting an optically active 7-substituted-1,4-dioxepan-5-one derivative represented by formula (I) to ring opening polymerization in the presence of at least one catalyst selected from the group consisting of (i) an organotin compound, (ii) an organoaluminum compound and water, and (iii) an organozinc compound and water.Type: GrantFiled: April 10, 1992Date of Patent: June 22, 1993Assignee: Takasago International CorporationInventors: Akio Yamaguchi, Yoji Hori, Susumu Akutagawa
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Patent number: 5210332Abstract: An iridium-optically active phosphine complex represented by formula (I):[H.sub.2 Ir(L.sup.1)(L.sup.2)]Y (I)wherein L.sup.1 represents an optically active phosphine compound represented by formula (II): ##STR1## wherein Ar represents a phenyl group or a p- and/or m-lower alkyl-substituted phenyl group, or formula (III): ##STR2## L.sup.2 represents a tertiary phosphine compound represented by formula (IV): ##STR3## wherein Z represents a lower alkoxy group or a di-lower alkylamino group; and A represents an integer of from 1 to 3; Y represents BF.sub.4, PF.sub.6, ClO.sub.4, or BPh.sub.4, wherein Ph represents a phenyl group,and a process for producing an optically active alcohol using the above complex as an enantioselective catalyst are disclosed. The complex exhibits excellent catalytic activity to give high enantioselective yields in enantioselective synthesis, particularly enantioselective hydrogenation.Type: GrantFiled: March 20, 1992Date of Patent: May 11, 1993Assignee: Takasago International CorporationInventors: Takanao Taketomi, Susumu Akutagawa, Hidenori Kumobayashi, Hidemasa Takaya, Kazushi Mashima
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Patent number: 5159093Abstract: An iridium-optically active phosphine complex represented by formula (I):[H.sub.2 Ir(L.sup.1)(L.sup.2)]Y (I)wherein L.sup.1 represents an optically active phosphine compound represented by formula (II): ##STR1## wherein Ar represents a phenyl group or a p- and/or m-lower alkyl-substituted phenyl group, or formula (III): ##STR2## L.sup.2 represents a tertiary phosphine compound represented by formula (IV): ##STR3## wherein Z represents a lower alkoxy group or a di-lower alkylamino group; and A represents an integer of from 1 to 3; Y represents BF.sub.4, PF.sub.6, ClO.sub.4, or BPh.sub.4, wherein Ph represents a phenyl group, and a process for producing an optically active alcohol using the above complex as an enantioselective catalyst are disclosed. The complex exhibits excellent catalytic activity to give high enantioselective yields in enantioselective synthesis, particularly enantioselective hydrogenation.Type: GrantFiled: October 1, 1991Date of Patent: October 27, 1992Assignee: Takasago International CorporationInventors: Takanao Taketomi, Susumu Akutagawa, Hidenori Kumobayashi, Hidemasa Takaya, Kazushi Mashima
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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: 4962242Abstract: A process for producing an optically active alcohol represented by formula (I): ##STR1## wherein R.sub.1 is an alkyl group having from 2 to 11 carbon atoms, an alkenyl group having from 3 to 11 carbon atoms, an alkadienyl group having from 6 to 11 carbon atoms, a cyclohexyl group, an cyclohexylmethyl group, or a cyclohexylethyl group, provided that the olefin in the alkenyl group or alkadienyl group is not conjugated to the olefin at the 2-position thereof; and * means an asymmetric carbon atom,is disclosed, comprising subjecting an olefinic alcohol represented by formula (II): ##STR2## wherein R.sub.1 is the same as defined above to asymmetric hydrogenation in the presence of, as a catalyst, a ruthenium-optically active phosphine complex.According to the process of the invention, the desired optically active alcohols which are useful not only as intermediates for the manufacture of perfumes and vitamin E but also as liquid crystal materials can be produced with high optical purities.Type: GrantFiled: June 25, 1987Date of Patent: October 9, 1990Assignee: Takasago Perfumery Co., Ltd.Inventors: Nobuo Yamada, Toshiyuki Takezawa, Noboru Sayo, Misao Yagi, Hidenori Kumobayashi, Susumu Akutagawa, Hidemasa Takaya, Shinichi Inoue, Ryoji Noyori
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Patent number: 4962230Abstract: A process for producing an optically active carboxylic acid represented by formula (I): ##STR1## wherein R.sup.1, and R.sup.2, and R.sup.3 each represents a hydrogen atom, an alkyl group, an alkenyl group, or a phenyl or naphthyl group which may have a substituent, provided that all of R.sup.1, R.sup.2, and R.sup.3 are not simultaneously a hydrogen atom; when R.sup.1 and R.sup.2 are simultaneously a hydrogen atom, then R.sup.3 is not a methyl group; and that when R.sup.3 is a hydrogen atom, then R.sup.1 and R.sup.2 are each a group other then a hydrogen atom,is disclosed, comprising asymmetrically hydrogenating an .alpha.,.beta.-unsaturated carboxylic acid represented by formula (II): ##STR2## wherein R.sup.1, R.sup.2, and R.sup.3 are the same as defined above, in the presence of a ruthenium-optically active phosphine complex as a catalyst.Type: GrantFiled: November 16, 1987Date of Patent: October 9, 1990Assignee: Takasago International CorporationInventors: Hidemasa Takaya, Tetsuo Ohta, Ryoji Noyori, Noboru Sayo, Hidenori Kumobayashi, Susumu Akutagawa
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Patent number: 4933482Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a .beta.-keto acid derivative in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.Type: GrantFiled: June 9, 1988Date of Patent: June 12, 1990Assignee: Takasago International CorporationInventors: Noboru Sayo, Takao Saito, Hidenori Kumobayashi, Susumu Akutagawa, Ryoji Noyori, Hidemasa Takaya
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Patent number: 4916252Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a 1,3-diketone in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.Type: GrantFiled: June 16, 1988Date of Patent: April 10, 1990Assignee: Takasago International CorporationInventors: Noboru Sayo, Takao Saito, Hidenori Kumobayashi, Susumu Akutagawa, Ryoji Noyori, Hidemasa Takaya
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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: 4851537Abstract: A process for preparing an N-acyltetrahydroisoquinoline represented by formula (II) ##STR1## wherein A represents a phenylene ring substituted with a hydroxyl group, a lower alkoxy group, an acetoxy group, or a benzyloxy group; R represents a hydrogen atom, a lower alkyl group, or a phenyl group; and X represents a hydrogen atoms, a phenyl group, or a phenyl group substituted with a hydroxyl group, a lower alkoxy group, or an acetoxy group, which comprises asymmetrically hydrogenating an N-acyl-1-methylenetetrahydroisoquinoline or N-acyl-1-benzylidenetetrahydroisoquinoline represented by formula (I) ##STR2## wherein A, R, and X are as defined above, in the presence of an optically active ruthenium-phosphine complex as a catalyst. The process exclusively and efficiently provides a useful isomer of the N-acyltetrahydroisoquinoline of high purity which is useful as an intermediate for synthesizing isoquinoline type alkaloids as pharmaceuticals without involving optical resolution of a racemate.Type: GrantFiled: April 15, 1987Date of Patent: July 25, 1989Assignee: Takasago Perfumery Co., Ltd.Inventors: Ryoji Noyori, Masato Kitamura, Hidemasa Takaya, Hidenori Kumobayashi, Susumu Akutagawa
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Patent number: 4766225Abstract: A ruthenium-phosphine complex represented by formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom, a methyl group, or a methoxy group; and R.sup.2 represents a lower alkyl group, a halogenated lower alkyl group, a phenyl group, or a phenyl group substituted with a lower alkyl group. The complex is inexpensive and exhibits excellent performance as a catalyst for various organic syntheses, particularly for asymmetric hydrogenation.Type: GrantFiled: December 9, 1987Date of Patent: August 23, 1988Assignee: Takasago International CorporationInventors: Noboru Sayo, Takanao Taketomi, Hidenori Kumobayashi, Susumu Akutagawa
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Patent number: 4766227Abstract: A ruthenium-phosphine complex represented by formula (I): ##STR1## wherein R represents a hydrogen atom, a methyl group, or a methoxy group; and X represents ClO.sub.4, BF.sub.4, or PF.sub.6. The ruthenium-phosphine complex is inexpensive and exhibits excellent performance as a catalyst for various organic syntheses, particularly for asymmetric hydrogenation.Type: GrantFiled: December 9, 1987Date of Patent: August 23, 1988Assignee: Takasago International CorporationInventors: Noboru Sayo, Takanao Taketomi, Hidenori Kumobayashi, Susumu Akutagawa
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Patent number: 4764629Abstract: A ruthenium-phosphine complex represented by formula (I): ##STR1## wherein R represents a hydrogen atom, a methyl group, or a methoxy group; S represents a tertiary amine; when y is 0, then x is 2, z is 4, and p is 1; and when y is 1, then x is 1, z is 1, and p is 0. The complex is inexpensive and exhibits excellent performance as a catalyst for various organic syntheses, and particularly asymmetric hydrogenation.Type: GrantFiled: November 25, 1987Date of Patent: August 16, 1988Assignee: Takasago International CorporationInventors: Noboru Sayo, Takanao Taketomi, Hidenori Kumobayashi, Susumu Akutagawa
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Patent number: 4739084Abstract: A ruthenium-phosphine complex having a 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl or its derivative as a ligand and carboxyl groups bonded to the ruthenium atom thereof is disclosed. The complex is inexpensive and exhibits excellent performances as a catalyst for various organic syntheses, and particularly for asymmetric hydrogenation.Type: GrantFiled: April 15, 1987Date of Patent: April 19, 1988Assignee: Takasago Perfumery Co., Ltd.Inventors: Hidemasa Takaya, Tetsuo Ohta, Ryoji Noyori, Nobuo Yamada, Toshiyuki Takezawa, Noboru Sayo, Takanao Taketomi, Hidenori Kumobayashi, Susumu Akutagawa
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Patent number: 4739085Abstract: A ruthenium-phosphine complex represented by formula (I):[RuH.sub.l (R-BINAP).sub.m ]X.sub.n' (I)wherein R-BINAP is a tertiary phosphine represented by formula (II): ##STR1## R is a hydrogen atom or a methyl group; X is a ClO.sub.4, BF.sub.4, or PF.sub.6 ; and when l is 0, then m is 1 and n' is 2, and when l is 1, then m is 2 and n' is 1, is disclosed. The complex is inexpensive and exhibits excellent performances as a catalyst for various organic syntheses, and particularly for asymmetric hydrogenation.Type: GrantFiled: June 15, 1987Date of Patent: April 19, 1988Assignee: Takasago Perfumery Co., Ltd.Inventors: Hidemasa Takaya, Tetsuo Ohta, Ryoli Noyori, Noboru Sayo, Hidenori Kumobayashi, Susumu Akutagawa
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Patent number: 4705895Abstract: A phosphine compound represented by formula: ##STR1## wherein R represents a hydrogen atom or an acetyl group; and Ph represents a phenyl group. The phosphine compound is capable of forming a complex with a metallic element, e.g., rhodium, ruthenium, palladium, etc., which exhibits high performances as a catalyst for asymmetric syntheses.Type: GrantFiled: November 21, 1986Date of Patent: November 10, 1987Assignee: Takasago Perfumery Co., Ltd.Inventors: Tamon Okano, Hidenori Kumobayashi, Susumu Akutagawa, Jitsuo Kiji, Hisatoshi Konishi, Keiichi Fukuyama, Yasunobu Shimano
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Patent number: 4695631Abstract: A process for the preparation of enamines or imines by isomerization of allylamine derivatives is described. Allylamine derivatives represented by formula (I): ##STR1## are isomerized using as a catalyst a rhodium complex represented by formula (IV):[Rh(olefin)L].sup.+ X.sup.- (IV)to form enamines or imines represented by, respectively, formula (II) or formula (III): ##STR2## All of the symbols in the above formulae are as described. These enamines or imines are useful intermediates for the preparation of a number of organic compounds.Type: GrantFiled: June 30, 1982Date of Patent: September 22, 1987Assignee: Takasago Perfumery Co., Ltd.Inventors: Seinosuke Otsuka, Kazuhide Tani, Tsuneaki Yamagata, Susumu Akutagawa, Hidenori Kumobayashi, Misao Yagi
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Patent number: 4691037Abstract: A ruthenium-phosphine complex represented by the formula (I)Ru.sub.x H.sub.y Cl.sub.z (R--BINAP).sub.2 (S).sub.p (I)wherein R--BINAP represents tertiary phosphine represented by the formula (II) ##STR1## R which is the same represents hydrogen, methyl or t-butyl, S represents tertiary amine, y represents 0 or 1, and when y is 0, x represents 2, z represents 4 and p represents 1, and when y is 1, x represents 1, z represents 1 and p represents 0.Type: GrantFiled: January 6, 1986Date of Patent: September 1, 1987Assignee: Takasago Perfumery Co., Ltd.Inventors: Sadao Yoshikawa, Masahiko Saburi, Takao Ikariya, Youichi Ishii, Susumu Akutagawa