Rings Bonded Directly To Each Other In Acid Moiety Patents (Class 560/59)
  • Patent number: 5300668
    Abstract: 1-[4'-(2"-Ethyl-5",7"-dimethylimidazo[4,5-b]pyridin-3-yl)methylphenyl]cyclo pent-3-ene-1-carboxylic acid and its pharmaceutically acceptable salts inhibit angiotensin II in mammals and are useful in treating conditions such as hypertension, congestive heart failure and glaucoma and as the active ingredient in pharmaceutical compositions for treating such conditions.
    Type: Grant
    Filed: March 10, 1993
    Date of Patent: April 5, 1994
    Assignee: Pfizer Inc.
    Inventor: Paul A. Dasilva Jardine
  • Patent number: 5296601
    Abstract: A process for producing a carboxylic acid ester, which comprises reacting an organic chloride having at least one chlorine atom on its ring of a substituted or unsubstituted, aromatic or heterocyclic hydrocarbon with carbon monoxide and an amine or an alcohol in the presence of a base by using as catalysts a palladium compound and a phosphine compound represented by the general formula (V):(R).sub.2 P--X--P(R).sub.2 (V)wherein R is an alkyl group or a substituted or unsubstituted phenyl group, and X is an alkylene group having 1 to 6 carbon atoms, ##STR1## or a binaphthyl group.
    Type: Grant
    Filed: May 27, 1992
    Date of Patent: March 22, 1994
    Assignee: Nihon Nohyaku Co., Ltd.
    Inventors: Keiji Suto, Masaaki Kudo, Moriharu Yamamoto
  • Patent number: 5296638
    Abstract: An improved process for preparing carboxylated 2-allyl-phenols of general formula (I): ##STR1## is disclosed, which consists of a first step of simultaneous esterification and etherification of a carboxylated phenol, subsequent rearrangement of the resulting product to yield allyl-carboxylated allyl-phenol and end saponification of the latter into carboxylated 2-allyl-phenol.
    Type: Grant
    Filed: August 20, 1992
    Date of Patent: March 22, 1994
    Assignee: Eniricerche S.p.A.
    Inventors: Alessandro Lezzi, Arnaldo Roggero, Ugo Pedretti, Cesarina Bonfanti
  • Patent number: 5294639
    Abstract: Abstract of the Disclosure: .alpha.-Arylacrylic acid derivatives of the general formula I ##STR1## where X is ethylene or ethenylene;Y is a direct bond or oxygen;R.sup.1 is an unsubstituted or substituted mononuclear or dinuclear aromatic or heteroaromatic system;R.sup.2 is cyano, nitro, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio or haloalkylthio;n is 1 or 2, and the radicals may be different if n is 2, and(c m is 0, 1 or 2, and the radicals may be different if m is 2,with the proviso that R.sup.1 is not phenyl when n is 1 and m is 0, their preparation, insecticides and fungicides containing them and methods for their use.
    Type: Grant
    Filed: September 4, 1991
    Date of Patent: March 15, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Reinhard Kirstgen, Albrecht Harreus, Uwe Kardorff, Thomas Kuekenhoehner, Harald Rang, Gisela Lorenz, Eberhard Ammermann, Christoph Kuenast
  • Patent number: 5279764
    Abstract: The invention relates to dihalogenobenzene derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --(Z.sup.2 --A.sup.3).sub.n --R.sup.2wherein R.sup.1, R.sup.2, A.sup.1, A.sup.2, A.sup.3, Z.sup.1, Z.sup.2 and n are as defined in the specification.
    Type: Grant
    Filed: November 23, 1992
    Date of Patent: January 18, 1994
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Volker Reiffenrath, Joachim Krause, Georg Weber, Ulrich Finkenzeller, Andreas Wachtler, Thomas Geelhaar, David Coates, Ian C. Sage, Simon Greenfield
  • Patent number: 5274168
    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: December 4, 1992
    Date of Patent: December 28, 1993
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takayuki Higashii, Masayoshi Minai
  • Patent number: 5271864
    Abstract: Ferroelectric liquid crystal compounds and compositions containing cyclohexenyl derivatives are provided. Specifically provided are compounds of formula: ##STR1## wherein R.sub.1 and R.sub.2 can be an alkyl, cycloalkyl, alkenyl, alkoxy, thioalkyl, alkylsilyl group having from one to about twenty carbon atoms. Y denotes --COO--, --OOC--, --CH.sub.2 O--, or --OCH.sub.2 --; and Ar.sub.1 and Ar.sub.2, independently of one another, can be selected from the group consisting of phenyl rings, halogenated phenyl rings and nitrogen-containing aromatic groups. In preferred embodiments the compounds of this invention contain at least one nitrogen-containing aromatic ring. Ar.sub.1 and Ar.sub.2 can be selected from 1,4-phenyl, mono- or dihalogenated 1,4-phenyl, 2,5-pyridinyl, 2,5-pyrimidyl, 2,5-pyrazinyl, 2,5-thiadiazole, 3,6-pyridazinyl and 1,4-cyclohexyl either or both be chiral racemic groups or chiral nonracemic groups.
    Type: Grant
    Filed: August 7, 1992
    Date of Patent: December 21, 1993
    Assignee: Displaytech, Inc.
    Inventors: Michael D. Wand, Rohini T. Vohra, Kundalika M. More, William N. Thurmes
  • Patent number: 5264152
    Abstract: An optically active compound represented by the formula (I): ##STR1## wherein R is a straight or branched chain alkyl or alkoxy group having 1 to 15 carbon atoms, ##STR2## is a 1,4-cyclohexylene or 1,4-phenylene group, ##STR3## is a 1,4-phenylene or 3-fluoro-1,4-phenylene group, X is a mono-, di- or tri-fluoromethyl group, W is a straight or branched chain or cyclic alkylene group having 1 to 16 carbon atoms or a straight or branched chain alkenylene group having 2 to 16 carbon atoms, Y is a bond or --COO--, and Z is a straight or branched chain alkyl group having 1 to 8 carbon atoms, a phenyl group or a hydrogen atom, which is useful as a component of ferroelectric liquid crystal compositions or as a device utilizing said composition.
    Type: Grant
    Filed: April 7, 1992
    Date of Patent: November 23, 1993
    Assignee: Sharp Kabushiki Kaisha
    Inventors: Makoto Shiomi, Mitsuhiro Koden, Tomoaki Kuratate, Fumiaki Funada
  • Patent number: 5248813
    Abstract: A process for obtaining a substantially pure enantiomer of an aryl-substituted aliphatic carboxylic acid is described. The process utilizes first an enantiomerically enriched mixture the of aryl-substituted aliphatic carboxylic acid obtained from kinetic resolution, diastereomeric crystallization or asymmetric synthesis processes. This enriched mixture is reacted with a base producing a salt that has the following properties:(1) has at least one eutectic point;(2) a composition that is not at the eutectic point; and(3) a eutectic composition that is closer to the racemic composition than is the eutectic composition of said aryl-substituted carboxylic acid.Substantially pure, enantiomeric salt is separated, leaving a mother liquor comprising the solvent and aryl-substituted aliphatic carboxylic acid enriched in the other enantiomer.
    Type: Grant
    Filed: October 14, 1992
    Date of Patent: September 28, 1993
    Assignee: Ethyl Corporation
    Inventors: Thanikavelu Manimaran, G. Patrick Stahly, R. Carl Herndon, Jr.
  • Patent number: 5248447
    Abstract: 2,3-difluorohydroquinone compounds of the formula I ##STR1## in which R.sup.1 and R.sup.2, in each case independently of one another, are alkyl having 1 to 15 C atoms or alkenyl having 3 to 15 C atoms which are unsubstituted, monosubstituted by cyano or at least monosubstituted by fluorine or chlorine, it also being possible for one CH.sub.2 group in these radicals to be replaced by --O--, --CO--, --CO--O--, --O--CO-- or --O--CO--O--,A.sup.1, A.sup.2 and A.sup.3, in each case independently of one another, are(a) trans-1,4-cyclohexylene, in which, in addition, one or two non-adjacent CH.sub.
    Type: Grant
    Filed: April 21, 1992
    Date of Patent: September 28, 1993
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Volker Reiffenrath, Joachim Krause, Andreas Wachtler, Georg Weber, Thomas Geelhaar, David Coates, Ian C. Sage, Simon Greenfield
  • Patent number: 5243065
    Abstract: A liquid-crystalline polymer having the repeating units represented by the following general formula (II): ##STR1## wherein R.sup.1 is ##STR2## wherein a is an integer having a value of 1 to 10,b is an integer having a value of 0 or 1,c is an integer having a value of 1 to 30,X.sup.1 is --COO--, --O-- or a single bond,M.sup.1 is ##STR3## and d is an integer having a value of 1 to 5.The liquid-crystalline polymer exhibits ferroelectricity in a wide temperature range including room temperature and has a high speed of response to electric field.
    Type: Grant
    Filed: October 20, 1992
    Date of Patent: September 7, 1993
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Satoshi Hachiya, Hiroyuki Endo, Shunji Uchida
  • Patent number: 5238603
    Abstract: A liquid crystal compound having specific features suitable to use for a display mode utilizing ferroelectric liquid crystals, particularly a large spontaneous polarization value and a liquid crystal composition using the compound are provided, which compound is an optically active liquid crystalline compound of the formula ##STR1## wherein l and m each are 0 or 1; at least one of R.sup.1 and R.sup.2 is an optically active alkoxy group of the formula ##STR2## wherein R.sup.3 is 2 or 3C alkyl and R.sup.4 is 3-18C alkyl, but R.sup.3 .noteq.R.sup.4 and the other thereof is 1-20C alkyl, alkoxy or alkanoyloxy, halogen or cyano; and A is a specified two or three rings compound.
    Type: Grant
    Filed: April 7, 1992
    Date of Patent: August 24, 1993
    Assignee: Chisso Corporation
    Inventors: Kazutoshi Miyazawa, Naoyuki Yoshida, Masakazu Kaneoya
  • Patent number: 5238602
    Abstract: Compounds of the formula ##STR1## wherein n stands for the number 0 or 1; the rings A.sup.1, A.sup.2 and A.sup.3 represent 1,4-phenylene, 2-fluoro-1,4-phenylene or trans-1,4-cyclohexylene or one of these rings also represents a 2,5-disubstituted pyrimidine ring or a trans-2,5-disubstituted m-dioxane ring; X.sup.1 represents a single covalent bond, --COO--, --OOC--, --CH.sub.2 CH.sub.2 --, p--C.sub.6 H.sub.4 --, --CH.sub.2 CH.sub.2 --p-- C.sub.6 H.sub.4 --, --CH.sub.2 CH.sub.2 --p--C.sub.6 H.sub.4 --CH.sub.2 CH.sub.2 -- or, insofar as the rings A.sup.1 and A.sup.2 represent 1,4-phenylene, also --NON--; R.sup.2 represents 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or alkenyloxy, with the proviso that the oxygen atom in alkenyloxy is linked with a saturated carbon atom; and R.sup.1 signifies 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or, insofar as R.sup.2 represents alkenyloxy, also alkyl, their manufacture, as well as liquid crystalline mixtures and the use for electro-optical purposes.
    Type: Grant
    Filed: May 26, 1987
    Date of Patent: August 24, 1993
    Assignee: Hoffmann La Roche Inc.
    Inventors: Martin Petrzilka, Martin Schadt
  • Patent number: 5235100
    Abstract: A process for the separation of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process comprises:i) separating a racemic mixture of an aliphatic carboxylic acid or ester thereof having the formula: ##STR1## where R.sub.1 is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; cycloalkyl; alkyl-substituted cycloalkyl; C.sub.6 to C.sub.14 aryl; C.sub.1 to C.sub.6 alkylthio; C.sub.2 to C.sub.8 cycloalkylthio; C.sub.6 to C.sub.10 arylthio; C.sub.6 to C.sub.10 arylcarbonyl; C.sub.4 to C.sub.8 cycloalkenyl; trifluoromethyl; halo; or C.sub.4 to C.sub.
    Type: Grant
    Filed: January 24, 1992
    Date of Patent: August 10, 1993
    Assignee: Ethyl Corporation
    Inventors: Azfar A. Choudhury, Abbas Kadkhodayan, Deepak R. Patil
  • Patent number: 5235095
    Abstract: An improved process for the separation of enantiomers of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process involves: (i) forming a salt solution comprising said racemic mixture of a C.sub.1 to C.sub.6 linear or branched aliphatic carboxylic acid and an organic or inorganic base; (ii) treating said salt solution with one-half molar equivalent of a chiral organic nitrogenous base having a base strength no stronger than said organic or inorganic base; and (iii) precipitating from the reaction solution formed in step (ii) the less soluble diastereomeric salt, the improvement being adding to the salt solution of step (ii) an inert organic or inorganic base that is soluble in the salt solution.
    Type: Grant
    Filed: January 24, 1992
    Date of Patent: August 10, 1993
    Assignee: Ethyl Corporation
    Inventors: Abbas Kadkhodayan, Deepak R. Patil, Azfar A. Choudhury
  • Patent number: 5230830
    Type: Grant
    Filed: April 15, 1992
    Date of Patent: July 27, 1993
    Assignee: The Secrteary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: David Coates, Simon Greenfield, Ian C. Sage
  • Patent number: 5229375
    Abstract: Phosphine oxide-terminated allene-ene-yne compounds are disclosed that possess DNA-cleaving, antimicobial and tumor growth-inhibiting properties. Methods of making and using those compounds are also disclosed.
    Type: Grant
    Filed: August 1, 1990
    Date of Patent: July 20, 1993
    Assignee: Scripps Clinic and Research Foundation
    Inventors: Peter E. Maligres, Kyriacos C. Nicolaou
  • Patent number: 5225586
    Abstract: The invention relates to benzocyclobutene capped benzotrifluoride based fluoroaryl ether compounds which are useful in preparing semi-permeable membranes, and films and coatings useful in electronic applications.
    Type: Grant
    Filed: September 13, 1991
    Date of Patent: July 6, 1993
    Assignee: The Dow Chemical Company
    Inventors: Theodore L. Parker, Thomas W. Regulski
  • Patent number: 5214191
    Abstract: 2-Phenylalkanoate esters which are useful as inhibitors of human leukocyte elastase.
    Type: Grant
    Filed: May 22, 1990
    Date of Patent: May 25, 1993
    Assignee: Cortech, Inc.
    Inventors: Gary P. Kirschenheuter, Lyle W. Spruce, John C. Cheronis
  • Patent number: 5209867
    Abstract: Novel derivatives of aromatic carboxylic acid esters which are useful as a dopant for liquid crystal compositions, and smectic liquid crystal compositions containing at least one of said derivatives.
    Type: Grant
    Filed: December 30, 1991
    Date of Patent: May 11, 1993
    Assignee: Sharp Kabushiki Kaisha
    Inventors: Mitsuhiro Koden, Tomoaki Kuratate, Fumiaki Funada
  • Patent number: 5207946
    Abstract: A liquid crystal compound represented by formula (I): ##STR1## wherein R.sub.1 represents an alkyl group having from 3 to 18 carbon atoms; R.sub.2 represents an alkyl group having from 3 to 18 carbon atoms; X represents ##STR2## (A) and (B) each represents a group selected from the group consisting of ##STR3## and * indicates an optically active center.
    Type: Grant
    Filed: July 25, 1990
    Date of Patent: May 4, 1993
    Assignee: Showa Shell Sekiyu K.K.
    Inventors: Koichi Numazawa, Noriko Yamakawa, Yoshiichi Suzuki, Ichiro Kawamura
  • Patent number: 5206389
    Abstract: These acrylates are those of formulae: ##STR1## where R=C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.12 cycloalkyl, aryl, arylalkyl or alkylaryl; Y=C.sub.1 -C.sub.12 alkyl, C.sub.6 -C.sub.12 aryl, heterocyclic radical whose ring contains from 5 to 10 members and whose heteroatom is chosen from N, O and S, an alkylaryl in which the alkyl part contains from 1 to 4 carbon atoms, Y not being able to denote 1,4-phenylene when R denotes methyl; and Z=hydrocarbon radical containing at least 2 C forming with O and the 2 adjacent Cs a ring containing from 4 to 8 members.To prepare them, an acrylate of formula CH.sub.2 .dbd.CH--COOR is reacted with a dialdehyde OHC--Y--CHO in the presence of an effective quantity of at least one functionalisation catalyst.The invention also relates to the preparation of new polymers and copolymers from the said acrylates.
    Type: Grant
    Filed: June 27, 1991
    Date of Patent: April 27, 1993
    Assignee: Atochem
    Inventors: Marie-Christine Berthe, Paul Caubere, Yves Fort
  • Patent number: 5202458
    Abstract: Compounds of the formula I or II ##STR1## in which R, R.sup.0, R.sup.1 and R.sup.2 are as defined in claim 1. The compounds, some of which are novel, are light stabilizers for color photographic recording materials.
    Type: Grant
    Filed: August 5, 1991
    Date of Patent: April 13, 1993
    Assignee: Ciba-Geigy AG
    Inventor: David G. Leppard
  • Patent number: 5198569
    Abstract: The asymmetric hydrogenation of aliphatic .alpha.-keto esters in the presence of rhodium catalysts which contain as chiral ligand a diphosphine of formula IV(R.sub.3).sub.2 P--Q--P(R.sub.3)hd 2 (IV)wherein R.sub.3 is phenyl, C.sub.1 -C.sub.6 alkylphenyl or C.sub.1 -C.sub.6 alkoxyphenyl, and Q is [2,2,1]-bicyloheptan-1,2-ylene or [2,2,1]-bicyclohept-4,5-en-1,2-ylene, gives the corresponding (R)- or(S)-.alpha.-hydroxycarboxylic acid esters in high rates of chemical conversion and in high enantiomer excesses.
    Type: Grant
    Filed: September 11, 1991
    Date of Patent: March 30, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans-Ulrich Blaser, Ulrich Pittelkow, Felix Spindler
  • Patent number: 5198151
    Abstract: A ferroelectric liquid crystal composition suitable to large capacity display which contains from 0.01 to 1% by weight of a liquid crystal or liquid crystal-compatible compound having a fluoroalkyl group in ferroelectric liquid crystals exhibiting a smectic C phase.
    Type: Grant
    Filed: April 6, 1990
    Date of Patent: March 30, 1993
    Assignee: Sharp Kabushiki Kaisha
    Inventors: Tomoaki Kuratate, Mitsuhiro Koden, Fumiaki Funada
  • Patent number: 5198570
    Abstract: Highly fluorinated aryloxyfluoroether esters, acids and alcohols, which are intermediates in the production of vinyl monomers, are provided. Also provided is a process for making aryloxyfluoroether esters by the base catalyzed addition of hydroxyaromatic compounds to perfluorovinylether esters.
    Type: Grant
    Filed: January 31, 1990
    Date of Patent: March 30, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Andrew E. Feiring
  • Patent number: 5191108
    Abstract: The invention relates to catechol carboxylic acid derivatives of the formula ##STR1## wherein, R.sub.1 is ##STR2## acetyl, hydrogen, hydroxy or alkanoyloxy, R.sub.2 is ##STR3## hydroxy, hydrogen or alkanoyloxy, wherein R is hydrogen, lower alkyl or --(CH.sub.2).sub.n --N--(lower alkyl).sub.2,R.sub.3 is hydrogen, lower alkyl or amino,R.sub.4 is hydrogen, lower alkyl, halogen or aminoA is ##STR4## wherein, R.sub.5 is hydrogen or acyl, R.sub.6 is hydrogen, halogen, lower alkyl, aryl or cycloalky, and R.sub.7 and R.sub.8, independently, are hydrogen, lower alkyl or halogen, orA is ##STR5## wherein, R.sub.5 is hydrogen or acyl, R.sub.9 is hydrogen, lower alkyl, R.sub.10 is hydrogen, lower alkyl or halogen, R.sub.11 is hydrogen, lower alkyl, cycloalkyl or halogen, m is 0 or 1, n is an integer of 2-10, provided, that no more than one of R.sub.1 or R.sub.2 can be hydroxy, alkanoyloxy or ##STR6## and when R is hydrogen, salts thereof with pharmaceutically acceptable bases or when R is --(CH.sub.2).sub.
    Type: Grant
    Filed: April 3, 1991
    Date of Patent: March 2, 1993
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Matthew Carson, Ru-Jen L. Han, Ronald A. Lemahieu
  • Patent number: 5188762
    Abstract: A mesomorphic compound represented by the following formula (I): ##STR1## wherein R.sub.1 denotes a linear or branched alkyl group having 2-16 carbon atoms capable of including one or two non-neighboring methylene groups which can be replaced with ##STR2## and capable of including fluorine substituted for hydrogen; A denotes --A.sub.1 -- or --A.sub.1 --A.sub.2 -- and B denotes --B.sub.1 -- or --B.sub.1 --B.sub.2 -- wherein A.sub.1, A.sub.2, B.sub.1 and B.sub.2 respectively denote ##STR3## wherein Y.sub.1 and Y.sub.2 respectively denote H, F, Cl, Br, --CH.sub.3, --CN or --CF.sub.3 ; Z.sub.1 and Z.sub.2 respectively denote ##STR4## Z.sub.3 denotes ##STR5## R.sub.2, R.sub.3 and R.sub.4 respectively denote a linear or branched alkyl group having 1-16 carbon atoms including a methylene group which can be replaced with ##STR6## with proviso that it is not adjacent to the silicon atom; p and q are respectively 0 or 1 with proviso that p+q is 0 or 1; and n is an integer of 1-12.
    Type: Grant
    Filed: May 20, 1991
    Date of Patent: February 23, 1993
    Assignee: Canon Kabushiki Kaisha
    Inventors: Takashi Iwaki, Takao Takiguchi, Takeshi Togano, Yoko Yamada, Shinichi Nakamura
  • Patent number: 5187298
    Abstract: Novel laser-optical recording elements which can be repeatedly erased and recorded on contain recording layers (a) which exhibit enantiotropic, ferroelectric smectic liquid crystalline (S.sub.C*) behavior, so that they can be switched back and forth between two thermodynamically stable, optically distinguishable ferroelectric smectic liquid crystlaline S.sub.C* order states on exposure to a laser beam of sufficient luminous power, by applying an external electric field. The recording layers (a) themselves consist mainly or exclusively of novel polymers P having chiral mesogenic side groups.
    Type: Grant
    Filed: May 18, 1990
    Date of Patent: February 16, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Kark-Heinz Etzbach, Gerhard Wagenblast, Wolfgang Brox, Axel Paul, Volker Bach
  • Patent number: 5184847
    Abstract: Ferrelectric chiral smetic liquid crystal compound are provided which have the formula, for example ##STR1## wherein R is a C.sub.1-20 alkyl group.
    Type: Grant
    Filed: November 4, 1991
    Date of Patent: February 9, 1993
    Assignee: Showa Shell Sekiyu Kabushiki Kaisha
    Inventors: Yoshiichi Suzuki, Hiroyuki Mogamiya, Ichiro Kawamura
  • Patent number: 5175339
    Abstract: A process for producing a dialkyl ester (i.e. BTDE) from its corresponding dianhydride (i.e., BTDA) comprising mixing the dianhydride, an organic solvent, solid catalyst and an alcohol capable of reacting with the dianhydride stirring the solution until the dianhydride and alcohol have reacted to form the dialkyl ester, separating the dialkyl ester from the catalyst and drying the ester to form a solid paticulate product. The product has a purity of over 85%.
    Type: Grant
    Filed: May 14, 1990
    Date of Patent: December 29, 1992
    Assignee: The Standard Oil Company
    Inventors: Eduard P. Babayan, Douglas G. Soden, Anthony Bosch
  • Patent number: 5173289
    Abstract: Aromatic esters and thioesters of the formula ##STR1## are useful in human and veterinary medicine and in cosmetic formulations. In the formula, X represents oxygen or sulfur, r' and 4" 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.'- dissubstituted alkyl having 4-12 carbon atoms or mono- or polycyclic cycloalkyl having 5-12 carbon atoms whose carbon linking carbon is trisubstituted and R.sub.3 and R.sub.4 represent hydrogen or lower alkyl.
    Type: Grant
    Filed: February 16, 1990
    Date of Patent: December 22, 1992
    Assignee: Centre International de Recherches Dermatologiques (C.I.R.D.)
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
  • Patent number: 5167863
    Abstract: There are disclosed an optically active compound represented by the general formula: ##STR1## wherein n, R.sub.1, R.sub.2, R.sub.3, R.sub.4, Q.sub.1, Q.sub.2, Q.sub.3, and M are defined as in the detailed explanation, and *-marked carbon atoms are each an asymmetric carbon atom; a liquid crystal composition comprising at least one optically active compound of said general formula and a liquid crystal optical modulator using the composition thereof.
    Type: Grant
    Filed: July 16, 1990
    Date of Patent: December 1, 1992
    Assignees: Hitachi, Ltd., Takeda Chemical Industries, Ltd.
    Inventors: Teruo Kitamura, Katsumi Kondo, Akio Mukoh, Koichi Matsumura, Mitsuru Kawada, Yoshihiro Sugihara
  • Patent number: 5167862
    Abstract: Compounds which may be used as a dopant or host in a ferroelectric chiral smectic liquid crystal mixture. The compounds are characterized in that they are derivates of an X-hydroxy carboxylic acid and contain the chiral unit (I), in which Ro may be alkyl, alkoxy, halogen, formula (II), where b may be 0 to 3 and the phenyl ring may be substituted, and a is 0 or 1. The chiral unit is combined with a range of mesogenic combinations of groups. Lactic acid derivatives are described in detail (i.e. Ro.dbd.methyl) together with various preparative routes, for example the compound formula (III), which has dopant properties in a range of hosts.
    Type: Grant
    Filed: June 8, 1989
    Date of Patent: December 1, 1992
    Inventors: Lawrence K. M. Chan, David Coates, Peter A. Gemmell, George W. Gray, David Lacey, Kenneth J. Toyne, Daniel J. S. Young
  • Patent number: 5166403
    Abstract: An amine derivative having a liquid crystal property over a wide temperature range and a process for production thereof are disclosed, the amine derivative being represented by formula (I) ##STR1## wherein A represents ##STR2## X.sub.1 and X.sub.2, which may be the same or different, each represents ##STR3## Y represents --O-- or ##STR4## R.sub.1 and R.sub.3, which may be the same or different, each represents a straight chain or branched chain alkyl group having 1 to 18 carbon atoms; R.sub.2 represents a hydrogen atom or a methyl group; m and n each represents 0 or 1; and p and q each represents 1 or 2, provided that p and q are 1 when n is 0, and p and q are not 2 at the same time when n is 1.
    Type: Grant
    Filed: January 14, 1991
    Date of Patent: November 24, 1992
    Assignee: Showa Denko K.K.
    Inventors: Ayako Kurotaki, Shuichi Naijoh, Kimie Nagai, Koro Shirane, Chozo Inoue
  • Patent number: 5166171
    Abstract: 6-Phenoxymethyl-4-hydroxytetrahydropyran-2-ones and 6-thiophenoxymethyl-4-hydroxytetrahydropyran-2-ones and the corresponding dihydroxycarboxylic acid derivatives, salts and esters, processes for the preparation of these compounds, their use as pharmaceuticals, pharmaceutical preparations and novel phenols and thiophenols Compounds of the general formula I ##STR1## and the corresponding open-chain dihydroxycarboxylic acids of the formula II ##STR2## in which X, Y and Z have the meanings given, and pharmacologically tolerated salts thereof with bases and pharmacologically tolerated esters thereof, processes for the preparation of these compounds, their use as pharmaceuticals and pharmaceutical preparations are described. Novel phenols and thiophenols of the formula III ##STR3## in which X, Y and Z have the meanings given, are also described.
    Type: Grant
    Filed: April 2, 1991
    Date of Patent: November 24, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Heiner Jendralla, Gunther Wess, Wilhelm Bartmann, Gerhard Beck
  • Patent number: 5145992
    Abstract: A process for producing an .alpha.-alkoxy acetic acids and salts thereof which comprises reacting an alcohol of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 can be hydrogen, alkyl, alkoxy, halo, phenyl, substituted phenyl, or hydroxy; A can be S, O or --CH.sub.2 --; and Alk is straight or branched chain alkylene, with a base in an aprotic solvent, then reacting the resulting alkoxide with a monohaloacetic acid ester to give an alkoxyacetate followed by reaction of the alkoxyacetate with a hydrogen halide, organic acid or Lewis acid in nitromethane to give the corresponding .alpha.-alkoxyacetic acid which then may be recovered or may optionally be converted to the corresponding salt by contracting the .alpha.-alkoxyacetic acid with a base.
    Type: Grant
    Filed: May 6, 1991
    Date of Patent: September 8, 1992
    Assignee: G. D. Searle & Co.
    Inventors: Richard A. Mueller, Richard A. Partis
  • Patent number: 5141669
    Abstract: Liquid crystal compounds which show a ferroelectric phase and which exhibit high spontaneous polarization values and smectic behavior over a range of temperatures have the formula ##STR1## wherein R.sup.1 is alkyl of from 1 to 16 carbon atoms; alkoxy; haloalkyl; alkoxyalkyl, wherein the alkoxy substituent thereof comprises a chain of carbon atoms including one or more oxygen ether atoms; or alkoxyalkoxy, wherein the alkoxy substituent thereof comprises a chain of carbon atoms including one or more oxygen ether atoms; R.sup.2 is alkyl of from 1 to 4 carbon atoms; each of R.sup.3 and R.sup.4 is alkylene; n is an integer 1 or 2; and W is alkyl of from 1 to 12 carbon atoms or fluoroalkyl of the formula ##STR2## wherein each of X, Y and Z is hydrogen or fluorine, m is zero or an integer from 1 to 6, and at least one of X, Y and Z is fluorine when m is zero.
    Type: Grant
    Filed: June 30, 1989
    Date of Patent: August 25, 1992
    Assignee: Polaroid Corporation
    Inventors: Iris B. K. Bloom, Yunn H. Chiang, William J. Cumming, Russell A. Gaudiana, Richard A. Minns
  • Patent number: 5138090
    Abstract: Substituted biphenyls can be prepared by reduction of appropriate ketones and, if appropriate, subsequent hydrolysis, cyclization, hydrogenation and separation of isomers. The substituted biphenyls can be used as active compounds in medicaments.
    Type: Grant
    Filed: February 27, 1990
    Date of Patent: August 11, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Fey, Rolf Angerbauer, Walter Hubsch, Thomas Philipps, Hilmar Bischoff, Peter Petzinna, Delf Schmidt
  • Patent number: 5137653
    Abstract: This invention provides a novel alkanoyl ester compound represented by general formula (I): ##STR1## (wherein A is of --, --O--, ##STR2## B is ##STR3## l and m are 1 or 2 provided that both are not simultaneously 2, k and n are an integer of 1 or more, respectively, provided that k>n, and R is an alkyl group), a liquid crystal composition containing this compound, a novel alkanoylphenyl compound or a novel alkanoylbiphenyl compound as an intermediate for the production of the above compound, and a method of producing the same. These novel alkanoyl ester compounds are excellent in the stability against light and the like and can take a liquid crystal state at a wide temperature range. Particularly, these compounds form liquid crystals of ferroelectricity having a large spontaneous polarization and a fast response rate by introducing an optically active group into the compound, so that they develop a very excellent effect as a starting material for optoelectronics and its related elements.
    Type: Grant
    Filed: October 18, 1991
    Date of Patent: August 11, 1992
    Assignee: Nippon Mining Co., Ltd.
    Inventors: Toshihiro Hirai, Atsushi Yoshizawa, Isa Nishiyama, Mitsuo Fukumasa, Nobuyuki Shiratori, Akihisa Yokoyama
  • Patent number: 5136090
    Abstract: An aldose reductase inhibitor, comprising a compound of the formula ##STR1## or a pharmaceutically acceptable salt thereof as the effective component, in which R denotes an alkyl of C.sub.1-12, ##STR2## wherein X.sub.1 and X.sub.2 are same or different and are hydrogen or halogen, cyclohexylmethyl, cyclohexyl, tetra-hydro-2H-pyran-1-yl-methyl, carboxy-lower alkyl or cyclo-lower alkyl and n is 2 or 3. These compounds exhibit a superior aldose reductase inhibiting activity with simultaneous high stability, and are for use in the prevention and therapy of diabetic complications.
    Type: Grant
    Filed: August 8, 1991
    Date of Patent: August 4, 1992
    Assignee: Toyo Jozo Kabushiki Kaisha
    Inventors: Yukio Suzuki, Kouichi Kuno, Motoshi Shoda, Masao Yaso, Satoshi Yaginuma, Akira Asahi
  • Patent number: 5133896
    Abstract: Novel cyanohydrin derivatives of general formula (I) wherein R.sup.1 is hydrogen, alkyl, alkoxy, perfluoroalkyl or perfluoroalkoxy, R.sup.2 is alkyl, r is 1 to 10, n and m are 0 or 1, provided if both n and m are 0 then X is (II) or (III), where (F) indicates one or more optional fluorines, p is 0 or 1, Z is a single bond if p is 0 and COO if p is 1; and if one or both of n or m are 1 then X is (IV), where each ring A, B and C is phenyl, fluoro- or chloro-phenyl, cyclohexyl, pyrimidyl, pyridyl, or dioxanyl, A, B and C are single bonds or linking groups, and (a+b+c) is 2 or 3. Liquid crystal materials containing these compounds are also described.
    Type: Grant
    Filed: July 11, 1990
    Date of Patent: July 28, 1992
    Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: David Coates, Simon Greenfield, Ian C. Sage
  • Patent number: 5132041
    Abstract: Disclosed are smetic liquid crystal compounds exhibiting ferroelectric behavior and having the formulaR.sup.1 --OR.sup.2).sub.a O--R.sup.3).sub.b Z--R*wherein R.sup.1 is alkyl or alkoxyalkyl, R.sup.2 and R.sup.3 are each alkylene, a is an integer of at least one, b is zero or one, R* is an optically active group containing an asymmetric center and --Z-- is an organic divalent core radical having parallel or coaxially extending bonds at the terminal ends thereof, the core radical having an axial ratio of at least two and being characterized by an essentially rigid and flat molecular structure. Presence of the ether-interrupted hydrocarbon tail moiety at the terminal end of the compounds provides a lowering in observed temperatures of phase transition.
    Type: Grant
    Filed: June 23, 1987
    Date of Patent: July 21, 1992
    Assignee: Polaroid Corporation
    Inventors: William J. Cumming, Russell A. Gaudiana, Cynthia McGowan, Richard A. Minns, Alaric Naiman
  • Patent number: 5130050
    Abstract: A new tetrastable liquid crystal is provided which is useful for display and switching devices. The liquid crystal has the formula ##STR1## where R.sub.1 is a C.sub.5-18 alkyl group and R.sub.2 is a C.sub.4-15 alkyl group and * is an optically active center.
    Type: Grant
    Filed: October 19, 1990
    Date of Patent: July 14, 1992
    Assignee: Showa Shell Sekiyo Kabushiki Kaisha
    Inventors: Takashi Hagiwara, Noriko Yamakawa, Ichiro Kawamura
  • Patent number: 5124070
    Abstract: Disclosed are herein optically active ester derivatives represented by the formula (I): ##STR1## (wherein R.sub.1 represents an alkyl group having 3 to 20 carbon atoms; R.sub.2 represents an optically active alkyl or alkoxyalkyl group having 3 to 15 carbon atoms optionally substituted by halogen atoms; Y represents --O--, --COO-- or --OCO--; X represents --COO-- or --OCO--; l represents a number of 1 or 2; k and m each represents a number of 0 or 1; n represents a number of 1 to 6), preparation processes therefor, liquid crystal materials containing such ester derivatives as active ingredient, and a light switching element using said liquid crystal materials as liquid crystal element.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: June 23, 1992
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takayuki Higashii, Isao Kurimoto, Shoji Toda, Masayoshi Minai, Takeshi Tani, Chizu Kawakami, Koichi Fujisawa, Kiyoshi Imamura
  • Patent number: 5124353
    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 3, 1989
    Date of Patent: June 23, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Christopher R. A. Godfrey
  • Patent number: 5116531
    Abstract: A liquid crystal compound represented by formula (I): ##STR1## wherein R.sub.1 represents an alkyl group having from 5 to 18 carbon atoms; R.sub.2 represents an alkyl group having from 4 to 15 carbon atoms; X represents a single bond, --O--, ##STR2## and * indicates an optically active center. The compound exhibits three stable states of molecular orientation.
    Type: Grant
    Filed: August 28, 1990
    Date of Patent: May 26, 1992
    Assignee: Showa Shell Sekiyu K.K.
    Inventors: Takashi Hagiwara, Noriko Yamakawa, Ichiro Kawamura
  • Patent number: 5110496
    Abstract: An optically active liquid crystal compound which is represented by the formula: ##STR1## wherein R.sub.1 and R.sub.2 each represents an alkyl or aralkyl group of 4-18 carbon atoms, R.sub.3 represents a haloalkyl group, X represents O, COO, OCO, CO or a single bond, Y represents COO, OCO, CH.sub.2 O or OCH.sub.2, Z represents COO or O, (A) represents a cyclic group shown by ##STR2## (B) represents a cyclic group shown by ##STR3## and l shows that the cyclic groups are substituted by at least one halogen atom.
    Type: Grant
    Filed: March 1, 1991
    Date of Patent: May 5, 1992
    Assignees: Showa Shell Sekiyu Kabushiki Kaisha, Teikoku Chemical Industry Co., Ltd.
    Inventors: Hiroyuki Mogamiya, Noriko Yamakawa, Yoshiichi Suzuki, Hitoshi Suenaga, Yasuhiro Hasegawa
  • Patent number: 5110497
    Abstract: An optically active compound represent by formula (I): ##STR1## wherein R.sub.1 represents a fluoroalkyl group having from 1 to 18 carbon atoms; R.sub.2 represents an alkyl group having from 1 to 16 carbon atoms and an aralkyl group having from 6 to 16 carbon atoms; R.sub.3 represents C.sub.2 F.sub.5, CF.sub.3, CHF.sub.2, or CH.sub.2 F; X represents a single bond, --O--, --COO--, or --OCO--; Y represents --COO--, --OCO--, --CH.sub.2 O--, or --OCH.sub.2 --; Z represents --COO-- or --O--; (A) and (B) each represent a cyclic group; and * indicates an optically active center, and a liquid crystal composition containing at least one of said optically active compounds are disclosed. The compound is useful not only as a liquid crystal compound but as a chiral dopant to provide a liquid crystal composition exhibiting a chiral smectic phase.
    Type: Grant
    Filed: January 28, 1991
    Date of Patent: May 5, 1992
    Assignee: Showa Shell Sekiyu K.K.
    Inventors: Yoshiichi Suzuki, Shigenori Sakuma, Noriko Yamakawa
  • Patent number: 5105004
    Abstract: The new aromatic ethers of the formulae ##STR1## can be used for the preparation of plastics which, in turn, can be processed further to give moulded articles, films, foils and filaments. The plastics prepared from the new aromatic ethers are distinguished by exceptional dimensional stability under heat.
    Type: Grant
    Filed: November 13, 1990
    Date of Patent: April 14, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Knud Reuter, Dieter Freitag, Gunther Weymans, Rolf Dhein, Paul J. Mayska, Karsten-Josef Idel, Volker Eckhardt, Uwe Westeppe