Rings Bonded Directly To Each Other In Acid Moiety Patents (Class 560/59)
  • Patent number: 5100579
    Abstract: Polyphenyl-based liquid crystal compounds represented by the following general formula (1) and liquid crystal composition containing the same: ##STR1## wherein R.sup.1 represents a straight or branched C.sub.1-18 alkyl group, haloalkyl group, aralkyl group or haloaralkyl group with or without optically active carbon, R.sup.2 represents a straight or branched C.sub.1-6 alkyl group, haloalkyl group or aralkyl group with or without optically active carbon, W represents (1) --OCO-- or --COO--, in which case T represents a halogen atom or a methyl group, or (2) a single bond, --O-- or --OCOO--, in which case T represents a halogen atom, X represents --OCO--, --COO--, --C.dbd.C--, --CH.dbd.N--, --N.dbd.CH, Y represents single bond, --O--, --COO--, --OCO--, --CH.sub.2 --, --OCH.sub.2 --, --COOCH.sub.2 -- or --OCOCH.sub.2 --, Z.sub.1 and Z.sub.2 represents a hydrogen or halogen atom, a cyano group or nitro group, Z.sub.1 may be the same or different from Z.sub.
    Type: Grant
    Filed: October 6, 1989
    Date of Patent: March 31, 1992
    Assignee: Ajinomoto Co., Inc.
    Inventors: Ryoichi Higuchi, Takao Sakurai, Tatsuru Tabohashi, Naoko Mikami, Kiriko Akaiwa, Eri Yamamoto, Koji Takeuchi
  • Patent number: 5098602
    Abstract: This invention provides a novel halogen-containing ester compound represented by the following general formula (I): ##STR1## (wherein R is an alkyl group, A is selected from a single bond, --O--, --COO-- and --CO--, both of X and Y are halogen atoms or either one of X and Y is a halogen atom and the other is a hydrogen atom, each of m and n is 0 or 1, m+n=0 or 1, each of k and l is an integer of 1 or more, provide k<l), a liquid crystal composition and a light switching element each containing the above compound as well as a novel fluorophenol compound represented by the following general formula (II): ##STR2## (wherein each of k and l is an integer of 1 or more, provided k<l) as an intermediate for the synthesis of the above ester compound and a method of producing the same.
    Type: Grant
    Filed: May 2, 1989
    Date of Patent: March 24, 1992
    Assignee: Nippon Mining Co., Ltd.
    Inventors: Toshihiro Hirai, Atsushi Yoshizawa, Isa Nishiyama, Mitsuo Fukumasa, Nobuyuki Shiratori, Akihisa Yokoyama
  • Patent number: 5096613
    Abstract: An optically active fluorine-containing alcohol of ##STR1## where R.sub.2 is a C.sub.1-18 alkyl and n is 2-10, and liquid crystal compound of ##STR2## wherein R.sub.1 and R.sub.2 each is a C.sub.1-18 alkyl, X is O, COO or OCO, Y is COO, OCO, CH.sub.2 O or OCH.sub.2, Z is COO or O, (A) and (B) each is for example ##STR3## and p is zero or one, which is prepared from (I) above.
    Type: Grant
    Filed: August 24, 1990
    Date of Patent: March 17, 1992
    Assignee: Showa Shell Sekiyu Kabushiki Kaisha
    Inventors: Yoshiichi Suzuki, Yasunori Sadamune, Noriko Yamakawa
  • Patent number: 5076947
    Abstract: An optically active compound having a high twistability and almost no change in the intrinsic pitch depending on temperature, and a liquid crystal composition comprising the compound are provided, which optically active compound is expressed by the formula ##STR1## wherein R.sup.1 and R.sup.2 each represent 1-20C alkyl or alkoxy, halogen or H; l, m and n each represent 0 or 1; and ##STR2## wherein Y represents H, halogen or cyano.
    Type: Grant
    Filed: June 6, 1989
    Date of Patent: December 31, 1991
    Assignee: Chisso Corporation
    Inventors: Masakazu Kaneoya, Manabu Uchida, Naoyuki Yoshida, Kazutoshi Miyazawa
  • Patent number: 5072023
    Abstract: A process is described in which a lactone ##STR1## is reacted with an alkylester X.sup.1 --CH.sub.
    Type: Grant
    Filed: February 15, 1990
    Date of Patent: December 10, 1991
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Jeffrey A. Robl
  • Patent number: 5069814
    Abstract: A benzoic acid derivative having a large positive dielectric anisotropy value and a superior compatibility, reducing the threshold voltage value of the resulting liquid crystal cell and being very effective for broadening the mesomorphic range of the resulting liquid crystal composiiton and reducing the driving voltage, and a liquid crystal composition containing the derivative are provided, which benzoic acid derivative is expressed by the formula ##STR1## wherein R represents an alkyl group of 1 to 10 carbon atoms and A represents ##STR2##
    Type: Grant
    Filed: February 14, 1990
    Date of Patent: December 3, 1991
    Assignee: Chisso Corporation
    Inventors: Toshiharu Suzuki, Yasuyuki Goto, Kisei Kitano
  • Patent number: 5068389
    Abstract: The invention relates to tertiary alcohols of the formula I ##STR1## wherein R.sup.1, A.sup.1, Z.sup.1, m, A.sup.2, Y, Q.sup.1, Q.sup.2, Q.sup.3 and Z.sup.2 have the meanings indicated in claim 1, and also to a process for the preparation of these compounds.
    Type: Grant
    Filed: May 3, 1990
    Date of Patent: November 26, 1991
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Andreas Wachtler, Rudolf Eidenschink, Joachim Krause, Hans-Adolf Kurmeier
  • Patent number: 5059345
    Abstract: An optically active compound represented by the general formula (I) of:R--Z--COO--(Ph).sub.k --Ph(Y)--CO--(CH.sub.2).sub.m C*HE L (1)In the general formula (I); R is an alkyl or alkoxy group having 4 to 22 carbon atoms; Z is the one selected from the group consisting of --Ph--, --Ph(X)--, --Ph--Ph--, Ph(X)--Ph--, --Ph--cy--, --Ph(X)--cy-- and --py--Ph-- is a 1,4-substituted phenylene group; --Ph--Ph-- is a 4,4'-substituted diphenylene group; --cy-- is a trans-1,4-cyclohexane group, --py is 2,5-substituted pyrimide group; X is a halogen atom at the ortho-position to R; k is zero or 1, Y is the one selected from the group consisting of H, OH, halogen atoms and methyl group; C* is an asymmetric carbon atom; E is the one selected from the group consisting of methyl group, halogen atoms and CF.sub.3 ; L is an alkyl, aryl or aralkyl group having not more than 10 carbon atoms; and m is an integer of zero to 6 where m takes zero when Y is H and Z is --Ph-- or --Ph--Ph--.
    Type: Grant
    Filed: November 3, 1988
    Date of Patent: October 22, 1991
    Assignee: Nippon Telegraph and Telephone Corporation
    Inventors: Shogo Kobayashi, Shigeki Ishibashi, Toshio Horie, Shinji Tsuru, Kouzaburou Nakamura, Tohru Maruno
  • Patent number: 5051527
    Abstract: The invention lies in novel ferroelectric liquid crystal compounds particularly represented by the general formulae, having a good responsibility in relation to the applied electric field and a wide range of phase transition points inclusive of the room temperature so as to be useful alone as the liquid crystal material but also to be mixed with other liquid crystal compounds for expanding the phase transition points to a desired range and making the response speed of the liquid crystal composition faster. ##STR1## In the formulae, m and n are same or different with each other and represent an integral of 1-20.
    Type: Grant
    Filed: February 28, 1989
    Date of Patent: September 24, 1991
    Assignee: Showa Shell Sekiyu K.K.
    Inventors: Yoshiichi Suzuki, Takashi Hagiwara, Hiroyuki Mogamiya
  • Patent number: 5032314
    Abstract: A compound capable of shortening the response time of liquid crystal display elements and a composition containing the same are provided, which compound is expressed by the formula ##STR1## wherein R.sup.1 represents a linear or branched chain alkyl group or alkoxy group, each of 1C-18C; Ar represents ##STR2## wherein X represents H, halogen atom, cyano group or methyl; A represents --COO-- or --CH.sub.2 O--; R.sup.2 represents a C.sub.1 -C.sub.18 alkyl, A C.sub.2 -C.sub.18 alkanoyl, a C.sub.3 -C.sub.18 alkoxycarbonyl or a C.sub.4 -C.sub.18 2-alkoxypropanoyl; C having a symbol * attached thereonto represents asymmetric carbon atom; and when R.sup.
    Type: Grant
    Filed: February 4, 1988
    Date of Patent: July 16, 1991
    Assignee: Chisso Corporation
    Inventors: Makoto Ushioda, Shinichi Saito, Kouji Ohno, Kazutoshi Miyazawa, Hiromichi Inoue
  • Patent number: 5013479
    Abstract: Disclosed are herein optically active ether derivatives represented by the formula (I): ##STR1## (wherein X represents --COO-- or --OCO--; A represents an alkyl or alkoxyl group having 3 to 15 carbon atoms; R represents an alkyl or alkyloxyalkyl group having 1 to 20 carbon atoms; l and m each represents a number of 1 to 2; and * indicates an asymmetric carbon atom), preparation processes therefor, liquid crystal materials containing such ether derivatives as active ingredient, and an optical switching element using said liquid crystal materials as liquid crystal element.
    Type: Grant
    Filed: April 18, 1990
    Date of Patent: May 7, 1991
    Assignees: Sumitomo Chemical Company, Limited, Hitachi, Ltd.
    Inventors: Masayoshi Minai, Takayuki Higashii
  • Patent number: 5002693
    Abstract: Disclosed are novel active benzene derivatives represented by the general formula (I): ##STR1## (wherein X represents --COO--, --OCO--, --CH.sub.2 O-- or --OCH.sub.2 --; A represents a hydrogen atom, a halogen atom or an alkyl or alkoxyl group having 1 to 20 carbon atoms; R represents an alkyl group having 1 to 20 carbon atoms; l and m each represents a number of 1 or 2, n represents a number of 0 or 1, but when n is 0 the sum of l and m is 3 or less; and * indicates asymmetric carbon atom), a process for producing the same, liquid-crystalline substances containing said derivatives as active ingredient, and optical switching elements utilizing the liquid crystal compositions containing said liquid-crystalline substances.
    Type: Grant
    Filed: March 18, 1988
    Date of Patent: March 26, 1991
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takayuki Higashii, Masayoshi Minai
  • Patent number: 5001128
    Abstract: Disclosed are novel 3-hydroxy-3-methylglutarylcoenzyme A reductase inhibitors useful as antihypercholesterolemic agents represented by the formula ##STR1## and the corresponding ring-opened hydroxy acids and esters derived therefrom and pharmaceutically acceptable salts thereof.Pharmaceutical compositions containing said compounds and method of inhibiting the biosynthesis of cholesterol therewith are also disclosed.
    Type: Grant
    Filed: December 15, 1989
    Date of Patent: March 19, 1991
    Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.
    Inventors: Kent W. Neuenschwander, Anthony C. Scotese
  • Patent number: 4992429
    Abstract: Disclosed are novel substituted cyclohexenyl phosphinylhydroxybutyrates as 3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors useful as antihypercholesterolemic agents represented by the formula: ##STR1## and pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: August 24, 1989
    Date of Patent: February 12, 1991
    Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.
    Inventors: John W. Ullrich, Kent W. Neuenschwander, John R. Regan
  • Patent number: 4985172
    Abstract: Arylcarboxylates of 2-hydroxypropionates are known, amongst other compounds, as dopes for converting tilted smectic liquid-crystal phases into ferroelectric liquid-crystal phases.The novel chiral aryloxypropionates of the general formula ##STR1## are two-fold chiral and in which the symbols have the following meaning: R.sup.1 denotes a straight-chain alkyl or alkoxy radical having 1 to 16 carbon atoms or a branched alkyl or alkoxy radical having 4 to 16 carbon atoms, it being possible for one or two non-adjacent CH.sub.2 groups to be replaced by a sulfur and/or oxygen atom;A denotes one, two or three aromatic or heteroaromatic rings which are linked to one another directly or via one or two COO groups;B denotes a chemical bond or one or two aromatic or heteroaromatic rings which are linked directly to one another;R.sup.2(a) if B is a chemical bond, denotes an alkyl radical having 2 to 10 carbon atoms which contains an asymmetrical carbon atom which is substituted by CH.sub.3, halogen or a COOC.sub.2 H.sub.
    Type: Grant
    Filed: May 5, 1989
    Date of Patent: January 15, 1991
    Assignee: Hoechst AG
    Inventors: Rainer Wingen, Hans-Rolf Dubal, Wolfgang Hemmerling, Ingrid Muller, Dieter Ohlendorf
  • Patent number: 4979805
    Abstract: A ferroelectric liquid crystal composition containing an optically active mesomorphic compound represented by the following formula (I) or (II): ##STR1## wherein R.sub.1 and R.sub.2 are respectively an alkyl, and C with * represents an asymmetric carbon atom. The mesomorphic compound provides the ferroelectric liquid crystal composition with an extended operational life in a liquid crystal device.
    Type: Grant
    Filed: December 1, 1989
    Date of Patent: December 25, 1990
    Assignee: Canon Kabushiki Kaisha
    Inventors: Kazuo Yoshinaga, Kazuharu Katagiri
  • Patent number: 4966726
    Abstract: The new compounds produced from a molecular structural element with two chirality centers and at least one mesogenic structural element are defined by the general formula (I) ##STR1## in which the symbols have the following meaning: Y.sup.1 =H, (C.sub.1 -C.sub.10)alkyl, MC--CH.sub.2 or MC--CO, MC denoting the molecular radical of a mesogenic carboxylic acid after splitting off a COOH group,Y.sup.2 =(C.sub.1 -C.sub.10)alkyl, MC--CH.sub.2 or MC--CO, it being possible for Y.sup.1 and Y.sup.2 to jointly represent a MC--CH group, which is then part of a dioxolane ring,X=COOR.sup.1, CONH.sub.2, CONR.sup.2 R.sup.3 or C.tbd.N,R.sup.1 =(C.sub.1 -C.sub.10)alkyl or MC--CH.sub.2, andR.sup.2, R.sup.3 =H and (C.sub.1 -C.sub.4)alkyl or, independently of each other, (C.sub.1 -C.sub.4)alkyl.Said esters preferably find application as dopants in twistable liquid crystal phases in which they produce temperature compensation and twisting.
    Type: Grant
    Filed: July 18, 1988
    Date of Patent: October 30, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunter Scherowsky, Manel Gunaratne
  • Patent number: 4959173
    Abstract: An optically active ester of the formula ##STR1## wherein p is 0 or 1, q is 1 or 2, r is 1 or 2, q+r is 3, and s is 0 or 1. R.sub.1 and R.sub.2 in the above formula are each independently selected from the group consisting of C.sub.6-18 straight chain alkyl and an optically active group of the formula ##STR2## and in which m is 2 to 5, n is 1 or 2, X is hydrogen or chlorine, R.sub.3 is hydrogen or C.sub.1-11 straight chain alkyl, and C.sup.* represents a chiral carbon atom, with the proviso that when n is 1 and X is hydrogen, R.sub.3 is C.sub.1-11 straight chain alkyl. When q is 2 and r is 1 and R.sub.1 is C.sub.6-18 straight chain alkyl, p is 1; on the other hand, when q is 1 and r is 2 and R.sub.2 is an optically active group of the above formula, s is 1. One of R.sub.1 and R.sub.2 is an optically active group of the above formula, and the other of R.sub.1 and R.sub.2 is C.sub.6-18 straight chain alkyl.
    Type: Grant
    Filed: September 8, 1988
    Date of Patent: September 25, 1990
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Toshihiro Shibata, Norio Kurosawa, Masaki Kimura
  • Patent number: 4957940
    Abstract: Certain bicyclo [2.2.1] heptane and bicyclo [2.2.2] octane substituted tetrahydro-2H-pyran-2-ones and the corresponding ring-opened acids derived therefrom are potent inhibitors of the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMG-CoA reductase) and are useful as hypocholesterolemic and hypolipidemic agents.
    Type: Grant
    Filed: November 21, 1989
    Date of Patent: September 18, 1990
    Assignee: Warner-Lambert Company
    Inventor: Bruce D. Roth
  • Patent number: 4952337
    Abstract: Biphenyl egters of formula (I), ##STR1## wherein formula (II) represents formula (III) or formula (IV), R.sub.1 represents C.sub.3 -C.sub.12 alkyl, alkoxy, alkylcarbonyloxy, alkoxycarbonyl or alkoxycarbonyloxy, j is O or 1 R.sub.2 represents C.sub.3 -C.sub.12 alkyl or alkoxy, one of Q.sub.1 or Q.sub.2 is fluorine and the other is hydrogen, provided that when j is O and formula (II) is formula (III) and both R.sub.1 and R.sub.2 are n-alkyl, then the total number of carbon atoms in R.sub.1 and R.sub.2 is more than 12. These compounds may be used as constituents of liquid crystal mixtures which show a room temperature ferroelectric smectic phase, and a number of such mixtures are described.
    Type: Grant
    Filed: June 9, 1988
    Date of Patent: August 28, 1990
    Assignee: The Secretary of State for Defence in her Majesty's Government of the United Kingdom, of Great Britain and Northern Ireland
    Inventors: Madeline J. Bradshaw, Edward P. Raynes, David I. Bishop, Ian C. Sage, John A. Jenner
  • Patent number: 4943386
    Abstract: A liquid crystalline compound represented by formula ##STR1## wherein R denotes an alkyl or alkoxy group having 1 to 20 carbon atoms,m and n are each 0 or 1, provided m and n are not 1 at the same time. ##STR2## X and Y each denote a hydrogen atom, a halogen atom or a nitro group, provided X and Y are not hydrogen atoms at the same time, andQ* denotes an optically active group having an asymmetric carbon atom and a linear or cyclic alkyl or alkenyl group which may be substituted by a halogen atom, or the like.
    Type: Grant
    Filed: October 4, 1988
    Date of Patent: July 24, 1990
    Assignees: Dainippon Ink & Chemicals, Inc., Kawamura Institute of Chemical Research
    Inventors: Sadao Takehara, Toru Fujisawa, Yoshi Arai, Jitsuo Kurokawa
  • Patent number: 4943384
    Abstract: Cyclohexane derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 IwhereinR.sup.1 and R.sup.2 are each H or an alkyl group which has 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-groups, and/or --CO--O-- groups and/or --CH.dbd.CH-- groups, or are F, Cl, Br, CN or R.sup.3 --A.sup.3 --Z.sup.2 --,A.sup.1 is --A--, A.sup.4 --Z.sup.o --A-- or --A--Z.sup.o --A.sup.4 --,A is a trans-1,4-cyclohexylene or 1,4-cyclohexenylene group which is unsubstituted or is monosubstituted or polysubstituted in the 2-, 3-, 5- and/or 6-position by F and/or Cl and/or Br and/or CN and/or an alkyl group or a fluorinated alkyl group each of which has 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-- groups and/or --CO--O-- groups, which trans-1,4-cyclohexylene or 1,4-cyclohexenylene group can optionally also be substituted in the 1-position and/or 4-position and one or two CH.sub.
    Type: Grant
    Filed: November 21, 1986
    Date of Patent: July 24, 1990
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Wolfgang Sucrow, Herbert Wolter, Rudolf Eidenschink
  • Patent number: 4940727
    Abstract: Novel 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase inhibitors are useful as anti-hypercholesterolemic agents and are represented by the following general structural formulae (I) and (II): ##STR1##
    Type: Grant
    Filed: October 6, 1988
    Date of Patent: July 10, 1990
    Assignee: Merck & Co., Inc.
    Inventors: Edward S. Inamine, Otto D. Hensens, David R. Houck, Ta J. Lee, Robert L. Smith, Wasyl Halczenko, George D. Hartman, Gerald E. Stokker
  • Patent number: 4925658
    Abstract: Aromatic esters and thioesters have the formula ##STR1## wherein X represents oxygen or sulfur,R.sub.1 represents --CH.sub.2 OH, --CH(OH)--CH.sub.3, --COOR.sub.5 or ##STR2## R.sub.5 represents hydrogen, lower alkyl, lower alkenyl, monohydroxyalkyl or polyhydroxyalkyl,r' and r" represent hydrogen, lower alkyl, monohydroxyalkyl, polyhydroxyalkyl, aryl or benzyl optionally substituted, the residue of an amino acid or aminated sugar, or taken together form a heterocycle,R.sub.2 represents .alpha.,.alpha.'-disubstituted alkyl having 4-12 carbon atoms or mono- or polycyclic cycloalkyl having 5-12 carbon atoms whose carbon linking carbon is trisubstituted,R.sub.3 represents hydrogen, lower alkyl, or --Si(CH.sub.3).sub.2 R'.sub.3 wherein R'.sub.3 represents lower alkyl, andR.sub.4 represents hydrogen or lower alkyl, andthe salts of these aromatic esters and thioesters of formula (I) when R.sub.5 represents hydrogen.
    Type: Grant
    Filed: January 19, 1989
    Date of Patent: May 15, 1990
    Assignee: Centre International De Recherches dermatologiques (CIRD)
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
  • Patent number: 4925591
    Abstract: Disclosed is a mesomorphic compound having a .beta.-hydroxycarboxyl group as the chiral source, which is represented by the formula: ##STR1## wherein m and n are integers of from 1 to 18, X.sub.1 and X.sub.2 independently represent fluorine, chlorine or hydrogen, Y represents ##STR2## or --O--, Z represents a direct bond, ##STR3## --CH hd 2O-- or --OCH.sub.2 --, and * indicates the asymmetric carbon. The mesomorphic compound is valuable as a ferroelectric liquid crystal or an additive to a ferroelectric liquid crystal or to a compound showing the SmC phase and having no chiral group.
    Type: Grant
    Filed: December 22, 1988
    Date of Patent: May 15, 1990
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Jun Nakauchi, Mioko Uematsu, Keiichi Sakashita, Yoshitaka Kageyama, Seiji Hayashi, Kenji Mori
  • Patent number: 4923633
    Abstract: A compound suitable for use in a ferroelectric smectic liquid crystal composition having a structure which contains two chiral centers derived from alpha hydroxy carboxylic acid groups and having the formula: ##STR1## wherein R.sub.1 is n-alkoxy containing 1-12 carbo atoms and R.sub.2 is n-alkyl containing 1-12 carbon atoms. Methods of preparation and details of liquid crystal mixtures containing these compounds are described.
    Type: Grant
    Filed: November 30, 1987
    Date of Patent: May 8, 1990
    Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: George W. Gray, David Lacey, Kenneth J. Toyne, David Coates, Adam Jackson, Richard M. Scrowston
  • Patent number: 4921632
    Abstract: Liquid Crystal compounds represented by the following formula are disclosed. ##STR1## wherein R and R' are independently selected from alkyl groups containing 1.about.20 carbon atoms; X is --O--, --O--CO--O-- or direct bond; A.sub.1 and A.sub.2 are independently cyclic groups (such as phenylene and biphenylene), said cyclic groups may be substituted with 1.about.4 fluorine, chlorine or bromine atoms, or 1 or 2 substituent groups selected from the group consisting of cyano, nitro and trifluoromethyl groups; Y is --CO--O--, --O--CO--, --C.tbd.C--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.dbd.N--, --N.dbd.CH--, --N.dbd.N--, --CH.sub.2 S--, --SCH.sub.2 -- or direct bond; and * represents asymmetric atom providing optical activity.
    Type: Grant
    Filed: August 19, 1988
    Date of Patent: May 1, 1990
    Assignees: NEC Corporation, Sanyo Chemical Industries, Ltd.
    Inventors: Toyokazu Nakamura, Yuzi Kato, Shohei Naemura, Chizuka Tani, Masahiro Satoh, Kunikiyo Yoshio, Hiroshi Kishiki, Hiroshi Hoshino
  • Patent number: 4917817
    Abstract: 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: Grant
    Filed: July 21, 1988
    Date of Patent: April 17, 1990
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiroyuki Nohira, Masanao Kamei, Hideki Kanazawa, Tetsuya Abe, Yoko Yamada, Yuko Etoh
  • Patent number: 4913721
    Abstract: Compounds of formula (I): ##STR1## and stereoisomers thereof, wherein V is an oxygen or a sulphur atom; X and Y, which may be the same or different, are hydrogen or halogen atoms, or optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkynyl, haloalkyl, alkoxy, haloalkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted acyloxy, optionally substituted amino, acylamino, nitro, nitrile, --CO.sub.2 R.sup.3, --CONR.sup.4 R.sup.5, or --COR.sup.6 groups; or the groups X and Y, when they are in adjacent positions on the phenyl ring, may join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; and Z is optionally substituted methylene, optionally substituted amino, oxygen or sulphur and when Z is a substituted methylene group, the substituent may join the 2-position of the phenyl ring to form a non-aromatic fused ring; R.sup.1 and R.
    Type: Grant
    Filed: October 31, 1988
    Date of Patent: April 3, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Christopher R. A. Godfrey
  • Patent number: 4914224
    Abstract: An optically active carboxylic acid derivative represented by the general formula ##STR1## wherein R represents a normal alkyl group having 1 to 20 carbon atoms, m and n represent 0 or 1 but are not 1 at the same time, X represents a hydrogen or halogen atom, Y represents a hydrogen or fluorine atom, provided that when Y is a hydrogen atom, X is a halogen atom, and that when n is 0, Y is ahydrogen atom, and Q* represents an optically active alkyl or 1-alkoxyethyl group having an asymmetric carbon atom.
    Type: Grant
    Filed: January 28, 1987
    Date of Patent: April 3, 1990
    Assignees: Dainippon Ink and Chemicals, Inc., Kawamura Institute of Chemical Research
    Inventors: Tadao Shoji, Sadao Takehara, Toru Fujisawa, Masashi Osawa, Hiroshi Ogawa, Yoshi Arai, Jitsuo Kurokawa
  • Patent number: 4914244
    Abstract: Difluorochloromethoxybenzenes are prepared by reacting phenols with trichloromethyl chloroformate (=di-phosgene) in the presence of hydrogen fluoride.
    Type: Grant
    Filed: January 14, 1987
    Date of Patent: April 3, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventor: Albrecht Marhold
  • Patent number: 4911861
    Abstract: Polyphenyl-based liquid crystal compounds represented by the following general formula (1) and liquid crystal composition containing the same: ##STR1## wherein R.sup.1 represents a straight or branched C.sub.1-18 alkyl group, haloalkyl group, aralkyl group or haloaralkyl group with or without optically active carbon, R.sup.2 represents a straight or branched C.sub.1-6 alkyl group, haloalkyl group or aralkyl group with or without optically active carbon, W represents (1) --OCO-- or --COO--, in which case T represents a halogen atom or a methyl group, or (2) a single bond, --O-- or --OCOO--, in which case T represents a halogen atom, X represents --OCO--, --COO--, --C.dbd.C--, --CH.dbd.N--, --N.dbd.CH, Y represents single bond, --O--, --COO--, --OCO--, --CH.sub.2 --, --OCH.sub.2 --, --COOCH.sub.2 -- or --OCOCH.sub.2 --, Z.sub.1 and Z.sub.2 represent a hydrogen or halogen atom, a cyano group or nitro group, Z.sub.1 may be the same or different from Z.sub.
    Type: Grant
    Filed: November 16, 1987
    Date of Patent: March 27, 1990
    Assignee: Ajinomoto Co., Inc.
    Inventors: Ryoichi Higuchi, Takao Sakurai, Tatsuru Tabohashi, Naoko Mikami, Kiriko Akaiwa, Eri Yamamoto, Koji Takeuchi
  • Patent number: 4911862
    Abstract: An optically active carboxylic acid derivative represented by the general formula ##STR1## wherein R represents a normal alkyl group having 1 to 20 carbon atoms, m and n represent 0 or 1 but are not 1 at the same time, X represents a hydrogen or halogen atom, Y represents a hydrogen or fluorine atom, provided that when Y is a hydrogen atom, X is a halogen atom, and that when n is 0, Y is a hydrogen atom, and Q* represents an optically active alkyl or 1-alkoxyethyl group having an asymmetric carbon atom.
    Type: Grant
    Filed: June 23, 1988
    Date of Patent: March 27, 1990
    Assignees: Dainippon Ink and Chemicals, Inc., Kawamura Institute of Chemical Research
    Inventors: Tadao Shoji, Sadao Takehara, Toru Fujisawa, Masashi Osawa, Hiroshi Ogawa, Yoshi Arai, Jitsuo Kurokawa
  • Patent number: 4911863
    Abstract: The invention relates to ferroelectric smectic liquid crystal mixtures and compounds. The invention also relates to electro-optical devices incorporating these mixtures.
    Type: Grant
    Filed: December 21, 1987
    Date of Patent: March 27, 1990
    Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Ian C. Sage, John A. Jenner, Hans A. Kurmeier, Pauluth Detlef, Claus Escher, Eike Poetsch
  • Patent number: 4906402
    Abstract: A compound having ferroelectric liquid crystal properties of the formula: ##STR1## wherein A is the residue of a liquid crystal material or a liquid crystal compatible material;X is O or S;n is 0 or 1;Y is any inert group which does not cause the melting point of the compound of Formula I to exceed 200.degree. C.;R.sup.1 is selected from H, C.sub.1-4 -alkyl and halogen; andR.sup.2 is C.sub.1-4 -alkyl or halogen;provided that R.sup.1 and R.sup.2 are different. In a suitable environment the compound is capable of alignment in two metastable states and is therefore suitable for use in multiplex-addressed, liquid crystal devices, such as flat bed large area screens and displays.
    Type: Grant
    Filed: September 1, 1987
    Date of Patent: March 6, 1990
    Assignee: Imperial Chemical Industries, PLC
    Inventors: David A. Jackson, Peter A. Gemmell
  • Patent number: 4904409
    Abstract: An optically active compound having characteristics necessary for realizing liquid crystal compositions provided with suitable characteristics, particularly a negative temperature characteristic and a very high twistability, and a liquid crystal composition containing the compound are provided, which optically active compound is expressed by the formula ##STR1## wherein R.sup.1 and R.sup.2 are 1-20 C alkyl or alkoxy or H; l, m and n are 0 or 1; X is F, Cl, Br or CN; and ##STR2## each independently represent ##STR3## wherein Y is H, halogen or CN.
    Type: Grant
    Filed: September 1, 1988
    Date of Patent: February 27, 1990
    Assignee: Chisso Corporation
    Inventors: Kazutoshi Miyazawa, Ohno Kouji, Naoyuki Yoshida, Masakazu Kaneoya
  • Patent number: 4898877
    Abstract: Novel circulation-active cyclohexenecarboxylates of the formula ##STR1## in which R.sup.1 is an organic radical,R.sup.2 is an optionally substituted aryl radical,R.sup.3 is an optionally substituted alkyl or aryl radical,X and Y are --CN, --COR.sup.4, --SO.sub.2 R.sup.4, --COOR.sup.5, --CONR.sup.6 R.sup.7 or --SO.sub.2 NR.sup.6 R.sup.7, andR.sup.4, R.sup.5, R.sup.6 and R.sup.7 are various organic radicals.
    Type: Grant
    Filed: February 18, 1988
    Date of Patent: February 6, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Meyer, Eckhard Schwenner, Martin Bechem, Rainer Gross, Matthias Schramm, Michael Kayser, Siegbert Hebisch
  • Patent number: 4897397
    Abstract: Certain aryl-alkynoic, alkenoic and alkanoic acids and derivatives and their use in treating inflammation, allergy and hyperproliferative skin disease are disclosed.
    Type: Grant
    Filed: December 16, 1988
    Date of Patent: January 30, 1990
    Assignee: Schering Corporation
    Inventors: Neng Y. Shih, David J. Blythin
  • Patent number: 4897216
    Abstract: 2,3-Difluorophenol derivatives of the formula ##STR1## wherein R.sup.1 and R.sup.2, in each case independently of one another, are an alkyl group having 1 to 15 C atoms in which, in addition, one or two nonadjacent CH.sub.2 groups may be replaced by --O--, --CO--, --CH.dbd.CH-- and/or --C.tbd.C--;A is 1,4-phenylene which is unsubstituted or substituted by one or two fluorines, or is trans-1,4-cyclohexylene or a single bond; andL.sup.1 and L.sup.2, in each case independently of one another, are H or F,are suitable as components of liquid-crystalline media.
    Type: Grant
    Filed: March 9, 1989
    Date of Patent: January 30, 1990
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Volker Reiffenrath, Joachim Krause, Andreas Wachtler, Georg Weber, Thomas Geelhaar
  • Patent number: 4886619
    Abstract: Compounds are provided which comprise a fluorocarbon terminal portion and a chiral hydrocarbon terminal portion, said terminal portions being connected by a central core, said compounds having tilted smectic mesophases or having latent tilted smectic mesophases which develop when said compounds having said latent mesophases are in admixture with said compounds having tilted smectic mesophases or said compounds having latent tilted smectic mesophases.
    Type: Grant
    Filed: May 29, 1987
    Date of Patent: December 12, 1989
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Eugene P. Janulis
  • Patent number: 4886623
    Abstract: 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: Grant
    Filed: December 23, 1987
    Date of Patent: December 12, 1989
    Assignee: Takasago International Corporation
    Inventors: Shigeru Mitsuhashi, Hitoshi Kondo, Tetsuharu Okazaki, Shinji Endoh, Hiroko Kudo, Akio Yamaguchi, Haruki Tsuruta, Susumu Akutagawa
  • Patent number: 4882085
    Abstract: An optically active lactic acid derivative represented by the following formula (I): ##STR1## wherein R represents a linear, branched or cyclic saturated or unsaturated hydrocarbon group having 1 to 18 carbon atoms; C* represents an asymmetric carbon atom; l is 0 or 1; m is 1 or 2; A represents a group selected from the following groups (a) and (b):(a) hydroxyl group, halogen, benzyloxy group, phenoxy group, toluenesulfonic acid group, acetyloxy group trifluoroacetyloxy group; ##STR2## (wherein R' is an alkyl group or alkoxy group having 4 to 18 carbon atoms, n is 0 or 1, ##STR3## with proviso that when A is selected from the group in the above group (a), l is 1 and m is 1 or 2; and when A is selected from the groups in the above group (b), m=n=1 when l is 0, or m and n are 0, 1 or 2 and m+n is 1 or 2 when l is 1, and ##STR4##
    Type: Grant
    Filed: December 28, 1988
    Date of Patent: November 21, 1989
    Assignee: Canon Kabushiki Kaisha
    Inventors: Kazuo Yoshinaga, Kazuharu Katagiri, Akira Tsuboyama, Hiroyuki Kitayama, Kenji Shinjo, Chieko Hioki
  • Patent number: 4880561
    Abstract: Disclosed is an optically active cyclopropane compound represented by the formula (1): ##STR1## wherein R is an alkyl or cycloalkyl group, n is 0 or 1, Y.sup.4 is --CO.sub.2 CH.sub.2 --, --OCO-- or --OCH.sub.2 --, Y.sup.1, Y.sup.2 and Y.sup.3 independently represent --CO.sub.2 --, --OCO--, --O--, a direct bond or --CH.sub.2 O--, Z.sup.1, Z.sup.2, and Z.sup.3 independently represent ##STR2## A.sup.1, A.sup.2 and A.sup.3 independently represent fluorine, bromine, chlorine, a cyano group or hydrogen, and the mark ##STR3## indicates an asymmetric carbon atom. The optically active cyclopropane compound includes a compound which exhibits a ferroelectric liquid crystalline characteristic, and a compound which does not exhibit a ferroelectric liquid characteristic when used alone, but, can be used as a constituent of a ferroelectric liquid crystal composition.
    Type: Grant
    Filed: April 16, 1987
    Date of Patent: November 14, 1989
    Assignee: Ajinomoto Co., Inc.
    Inventors: Tatsuru Tabohashi, Takao Sakurai, Ryoichi Higuchi, Naoko Mikami, Eri Yamamoto, Koji Takeuchi
  • Patent number: 4873018
    Abstract: An optically active 2-fluoro-1-alkanol compound represented by the formula (Ia): ##STR1## wherein R is an alkyl group having 1-16 carbon atoms, and C* is an asymmetric carbon atom; and an optically active compound derived from the fluoroalkanol and represented by the formula (Ib): ##STR2## wherein R and C* are the same as above, m is 1 or 2, n is 0 or 1, and A is a releasable substitutent. Because of the fluorine atom directly attached to an asymmetric carbon atom, these compounds are particularly effective in increasing a spontaneous polarization, improving a electric field responsive characteristic of a liquid crystal composition, and controlling the liquid crystal state.
    Type: Grant
    Filed: October 27, 1987
    Date of Patent: October 10, 1989
    Assignees: Canon Kabushiki Kaisha, Yamakawa Yakuhin Kogyo Kabushiki Kaisha
    Inventors: Hiroyuki Nohira, Masanao Kamei, Shinichi Nakamura, Kazuo Yoshinaga, Mariko Kai, Kazuharu Katagiri
  • Patent number: 4871472
    Abstract: Compounds of the formula I ##STR1## wherein R.sup.1 and R.sup.2 each independently of one another are R, OR, OCOR, COOR or OCOOR,is alkyl with 1 to 15 C atoms, wherein one or more CH.sub.2 groups which are not adjacent and are not linked by O can also be replaced by --O--, --CO--, --O--CO--, --CO--O--, --CH--halogen, --CHCN-- and/or --CH.dbd.CH--,A.sup.1, A.sup.2 and A.sup.3 each independently of one another are 1,4-phenylene or trans-1,4-cyclohexylene,m, n and o are each 0 or 1,m+n+o is 0, 1 or 2,Z.sup.1 and Z.sup.2 each independently of one another are --CH.sub.2 --O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 -- or a single bond andX is F, Cl, Br, I or CN,with the provisos given in claim 1, can be used as components of ferroelectric liquid crystal phases.
    Type: Grant
    Filed: October 9, 1987
    Date of Patent: October 3, 1989
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Joachim Krause, Volker Reiffenrath, Thomas Geelhaar
  • Patent number: 4871470
    Abstract: Cyclohexane derivatives of formula I ##STR1## wherein R is an alkyl group which has 1-12 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by O, --CO--O-- or --OCO--,A.sup.1 and A.sup.2 each independently of one another are trans-1,4-cyclohexylene or unsubstituted or fluorine-substituted 1,4-phenylene, and one of the groups A.sup.1 and A.sup.2 can also be a single bond,X is --CN, halogen, OH, --COOR.sup.1, --OOCR.sup.1, --COR.sup.1, --OR.sup.1 or R.sup.1 andR.sup.1 is an alkyl group which has 1-12 C atoms and in which one or two CH.sub.2 groups can also be replaced by O, but excluding direct links between two O atoms,with the proviso that, in the case of X=CN, A.sup.2 is trans-1,4-cyclohexylene or fluorine-substituted, 1,4-phenylene, are suitable as components of liquid-crystalline phases.
    Type: Grant
    Filed: October 30, 1987
    Date of Patent: October 3, 1989
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Andreas Wachtler, Joachim Krause, Rudolf Eidenschink, Georg Weber
  • Patent number: 4867903
    Abstract: A fluoroalkane derivative represented by the formula: ##STR1## wherein R denotes an alkyl group having 1-16 carbon atoms, C* denotes an asymmetric carbon atom, R.sup.1 denotes an alkyl or alkoxy group having 1-16 carbon atoms; ##STR2## respectively denote a phenylene group ##STR3## a cyclohexylene group ##STR4## or a pyrimidinylene group ##STR5## p is 0 or 1, q is 0 or 1 when p is 1, r is 0 or 1; and l, m and n are respectively 0 or a positive integer satisfying the relationship of l+m+n.gtoreq.1. The fluoroalkane derivative has a fluorine atom providing a large dipole moment and directly connected to an asymmetric carbon atom, so that it provides a high speed responsive characteristic through an increased spontaneous polarization when contained in a liquid crystal composition, especially a ferroelectric liquid crystal composition.
    Type: Grant
    Filed: March 6, 1987
    Date of Patent: September 19, 1989
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiroyuki Nohira, Masanao Kamei, Shinichi Nakamura, Kazuharu Katagiri
  • Patent number: 4855321
    Abstract: Novel 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase inhibitors which are useful as antihypercholesterolemic agents and are represented by the following general structural formulae (I) and (II): ##STR1## and pharmaceutically acceptable salts of the compounds (II) in which Z is hydrogen are disclosed.
    Type: Grant
    Filed: July 18, 1988
    Date of Patent: August 8, 1989
    Assignee: Merck & Co., Inc.
    Inventors: Robert L. Smith, Gerald E. Stokker
  • Patent number: 4853151
    Abstract: Dispirotetradecanes of the formula I ##STR1## wherein R.sup.1 and R.sup.2 are each independently of each other alkyl containing 1 to 12 carbon atoms wherein one or more non-adjacent CH.sub.2 groups may also be replaced by --O--, --CO--, --CO--O--, --O--CO--, --O--COO-- and/or --CH.dbd.CH-- (trans), one of the radicals R.sup.1 and R.sup.2 also being H, F, Cl, Br, I, CN, NO.sub.2, NCS,A.sup.1 and A.sup.2 are each independently of each other trans-1,4-cyclohexylene wherein one or two non-adjacent CH.sub.2 groups may be replaced by --O-- and/or --S--, or 1,4-phenylene wherein one or more CH groups may also be replaced by N, with it also being possible optionally for A.sup.1 and A.sup.2 to be substituted laterally or axially by F, Cl, CN, CH.sub.3,Z.sup.1 and Z.sup.2 are each independently of each other --C--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 -- or a single bond,m and n are each 0, 1 or 2,(m+n) 0, 1 or 2,X.sup.1, X.sup.2, X.sup.3 and X.sup.
    Type: Grant
    Filed: August 11, 1987
    Date of Patent: August 1, 1989
    Assignee: Merck Patent Gesellschaft Mit Beschrankfter Haftung
    Inventors: Fritz Vogtle, Wolfgang Calaminus
  • Patent number: 4852977
    Abstract: Novel lactic acid derivatives which may be used as a component of a ferroelectric smectic liquid crystal mixture, which derivatives have the general formula: ##STR1## in which R.sub.1 is alkyl or alkoxy and R.sub.2 is alkyl. Liquid crystalline compositions containing these compounds are also described.
    Type: Grant
    Filed: August 19, 1986
    Date of Patent: August 1, 1989
    Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Lawrence K. M. Chan, David Coates, Peter A. Gemmell, George W. Gray, David Lacey, Kenneth J. Toyne, Daniel J. S. Young