Halogen In Acid Moiety Patents (Class 560/65)
  • Patent number: 5332856
    Abstract: Bi-aromatic esters have the formula ##STR1## wherein R.sub.1 represents H, OH, --CH.sub.3, --CH.sub.2 OH, --CH(OH)CH.sub.3, --COOR.sub.9, ##STR2## or SO.sub.2 R.sub.10 ; R.sub.9 represents H, C.sub.1 -C.sub.6 alkyl or mono or polyhydroxyalkyl; R.sub.10 represents OH, C.sub.1 -C.sub.6 alkyl or ##STR3## r' and r'' represent H, C.sub.1 -C.sub.6 alkyl, aryl, aralkyl, mono or polyhydroxyalkyl, or r' and r'' taken together form a heterocycle; R.sub.2 represents H, C.sub.1 -C.sub.6 alkyl, OR.sub.9, F or --CF.sub.3 ; R.sub.3, R.sub.4 and R.sub.5 represent H, F, OH, --CH.sub.3, --OCH.sub.3, --CF.sub.3, --COOH or --CH.sub.2 OH; R.sub.6 and R.sub.8 represent H, .alpha.-substituted C.sub.3 -C.sub.15 alkyl, .alpha.,.alpha.'-disubstituted C.sub.4 -C.sub.12 alkyl, C.sub.3 -C.sub.12 cycloalkyl, C.sub.5 -C.sub.12 mono or polycyclic cycloalkyl whose linking carbon is trisubstituted, --SR.sub.11, --SO.sub.2 R.sub.11 or --SOR.sub.11 ; R.sub.11 represents C.sub.1 -C.sub.6 alkyl or cycloalkyl; R.sub.6 and R.sub.
    Type: Grant
    Filed: December 16, 1992
    Date of Patent: July 26, 1994
    Assignee: Centre International de Recherches Dermatologiques Galderma (CIRD Galderma)
    Inventors: Braham Shroot, Jean-Michel Bernardon, William R. Pilgrim
  • Patent number: 5330739
    Abstract: Compounds having the structure ##STR1## wherein (Z--COO is the residue of an iodinated aromatic acid; R is alkyl, cycloalkyl, aryl, aralkyl, ##STR2## or alkenyl; R.sup.1 is H, alkyl, cycloalkyl, aryl, aralkyl, or --CH.sub.2 --.sub.m CO.sub.2 R.sup.3 ;R.sup.2 is H, alkyl, cycloalkyl, aryl, aralkyl, --CH.sub.2 --.sub.n CO.sub.2 R.sup.4, or a ##STR3## group, wherein Z, R and R.sup.1 are as defined above;or R.sup.1 and R.sup.2, taken together with the carbon atom to which they are attached represent cycloalkyl;R.sup.3 is H, alkyl, cycloalkyl, aryl or aralkyl;R.sup.4 is H, alkyl, cycloalkyl, aryl or aralkyl; andm, n and p are independently an integer of from 0 to 17;provided that R.sup.1 and R.sup.2 can not both be H;are useful in the preparation of x-ray contrast compositions for medical imaging.
    Type: Grant
    Filed: December 4, 1992
    Date of Patent: July 19, 1994
    Assignee: Sterling Winthrop Inc.
    Inventor: Carl R. Illig
  • Patent number: 5330678
    Abstract: Disclosed are novel liquid crystal compounds containing a naphthalene ring, having an excellent light leaking ratio at tristable states, and represented by the following formula: ##STR1## wherein R.sub.1 is a C.sub.6 -C.sub.16 linear alkyl group or C.sub.6 -C.sub.16 linear alkoxy group, R.sub.2 is a C.sub.4 -C.sub.12 linear alkyl group, R.sub.3 is a C.sub.1 -C.sub.3 alkyl group or C.sub.1 -C.sub.3 haloalkyl group, and C having an asterisk indicates an asymmetric atom.The liquid crystal compounds are expected to find their applications in electrooptical devices and liquid crystal displays utilizing a S*.sub.(3) liquid crystal phase which shows tristable states.
    Type: Grant
    Filed: May 25, 1993
    Date of Patent: July 19, 1994
    Assignee: Showa Shell Sekiyu Kabushiki Kaisha
    Inventors: Nobuhiro Okabe, Hiroyuki Mogamiya, Noriko Yamakawa
  • Patent number: 5328639
    Abstract: A liquid crystal composition, comprising: at least one optically active mesomorphic compound having an asymmetric carbon atom to which a fluorine atom is directly bonded.
    Type: Grant
    Filed: December 31, 1992
    Date of Patent: July 12, 1994
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiroyuki Nohira, Masanao Kamei, Shinichi Nakamura, Kazuharu Katagiri, Masahiro Terada, Masataka Yamashita, Yoko Yamada, Kenji Shinjo, Takashi Iwaki, Chieko Hioki, Akio Yoshida, Toshiharu Uchimi
  • Patent number: 5326898
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently are hydrogen, lower alkyl of 1 to 6 carbons, halogen or lower alkoxy of 1 to 6 carbons; R.sub.5 and R.sub.5 ' independently are hydrogen or lower alkyl of 1 to 6 carbons; Y is oxygen or sulfur; Z is n-alkyl having 2 to 10 carbons, cyclo or branch-chained alkyl of 3 to 10 carbons, and straight chain alkenyl having 2 to 10 carbons, or cyclo or branched chained alkenyl of 3 to 10 carbons, and the Z-Y substituent is in a 1,2 (ortho) or 1,3 (meta) position on the phenyl ring relative to the ethene moiety; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3 to 6 carbons, cycloalkyl having 3 to 6 carbons, alkenyl having 2 to 6 carbons and 1 or 2 double bonds, alkynyl having 2 to 6 carbons and 1 or 2 triple bonds; B is COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.
    Type: Grant
    Filed: February 11, 1992
    Date of Patent: July 5, 1994
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 5324451
    Abstract: A compound represented by formula (I): ##STR1## wherein R.sub.1 represents an alkyl group having from 1 to 18 carbon atoms; R.sub.2 represents an alkyl group having from 2 to 16 carbon atoms; rings A, B, C, and D each represents a 1,4-phenylene group or a 1,4-phenylene group having one or two halogen atoms; Y represents a single bond, ##STR2## m and n each represents 0 or 1; p represents 0, 1, or 2; q represents 0 or an integer of from 1 to 6; and C* and C** each represents an asymmetric carbon atom in an (S)- or (R)-configuration, and a liquid crystal composition containing the compound of formula (I). The compound of formula (I) is a chiral liquid crystal compound exhibiting large spontaneous polarization, a long helical pitch, an SC* phase in a broad temperature range including room temperature, satisfactory orientation, and a high rate of response.
    Type: Grant
    Filed: April 20, 1992
    Date of Patent: June 28, 1994
    Assignees: Dainippon Ink and Chemicals, Inc., Kawamura Institute of Chemical Research
    Inventors: Sadao Takehara, Tadao Shoji, Hiroshi Ogawa, Toru Fujisawa, Masashi Osawa
  • Patent number: 5318770
    Abstract: Methods and compositions are disclosed for enhancing .sup.19 F magnetic resonance imaging which utilize trifluorometyl derivatives of iodinated X-ray contrast media. Typical magnetic resonance contrast media within the scope of the present invention include bis(trifluoromethyl)benzene derivatives, tris(trifluoromethyl)benzene derivatives, tetrakis(trifluoromethyl)benzene derivatives, and other related trifluoromethylated benzene derivatives.
    Type: Grant
    Filed: October 25, 1991
    Date of Patent: June 7, 1994
    Assignee: Mallinckrodt Medical, Inc.
    Inventors: David H. White, Steven R. Woulfe, Youlin Lin, Mills T. Kneller
  • Patent number: 5312564
    Abstract: A novel optically active liquid crystal compound and a liquid crystal composition containing the same are provided, which compound is expressed by the formula ##STR1## wherein R.sub.1 is alkyl or alkoxy of 4-18 C; R.sub.2 is alkyl, alkoxy, acyl or alkoxymethyl of 4-18C; but either one of R.sub.1 or R.sub.2 is an optically active group; either one of X.sub.1 or X.sub.2 is halogen atom and the other is H; m and n each are 0 or 1 and m+n is 0 or 1.
    Type: Grant
    Filed: December 31, 1992
    Date of Patent: May 17, 1994
    Assignee: Chisso Corporation
    Inventors: Kazutoshi Miyazawa, Hiromichi Inoue, Shinichi Saito, Takashi Inukai, Kanetsugu Terashima, Mitsuyoshi Ichihashi
  • 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: 5296612
    Abstract: A process for producing an enyne derivative, and intermediate, which is useful for preparing compounds showing strong inhibiting activities against squalane epoxidase of Eumycetes and strong anti-cholesterol activities. The process comprises reacting a compound of the formula: ##STR1## wherein W is a halogen atom, with an acetylene derivative, in the presence of a palladium catalyst, to obtain a compound of the formula: ##STR2## and, if necessary, N-alkylating this compound.
    Type: Grant
    Filed: November 12, 1992
    Date of Patent: March 22, 1994
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Susumu Nakagawa, Akira Asai, Satoru Kuroyanagi, Makoto Ishihara, Yoshiharu Tanaka
  • Patent number: 5294366
    Abstract: In accordance with the present invention, there are provided carboxylate compounds and liquid compositions thereof represented by the following formula (A) ##STR1## wherein R.sup.1 represents one group selected from the group consisting of alkyl group having 6 to 18 carbon atoms, alkoxy group having 6 to 18 carbon atoms and halogenated alkyl group of 6 to 18 carbon atoms, C* represents an asymmetric carbon atom, and R.sup.2 represents a group represented by the following formula (A)--(CH.sub.2).sub.m --CH.sub.3 or (B)--(CH.sub.2).sub.n --COOR.sub.3 wherein m represents an integer of 2 to 6, n represents an integer of 0 to 5, and R.sup.3 represents alkyl group having 1 to 10 carbon atoms.
    Type: Grant
    Filed: September 4, 1991
    Date of Patent: March 15, 1994
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Toyozi Shimizu, Hideo Yamaoka, Shinichi Nishiyama, Shoichi Miyakoshi, Tooru Yamanaka, Nobuyuki Doi
  • 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: 5276205
    Abstract: Novel insecticides have the formula ##STR1## in which R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.2 -C.sub.5 carboalkoxy, C.sub.2 -C.sub.5 alkylcarbonyl, nitro or cyano;R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkylthio, C.sub.3 haloalkenoxy, nitro, cyano, C.sub.2 -C.sub.5 alkylcarbonyl, C.sub.1 -C.sub.4 alkylsulfonyl or C.sub.2 -C.sub.5 carboalkoxy;R.sub.3 is hydrogen, halogen, C.sub.1 -C.sub.4 haloalkyl or C.sub.1 -C.sub.4 alkoxy;provided that:R.sub.1, R.sub.2 and R.sub.3 are not all hydrogen; orR.sub.1 and R.sub.2 taken together are C.sub.2 -C.sub.4 alkylene, C.sub.2 -C.sub.4 alkyleneoxy, C.sub.1 -C.sub.2 perhaloalkyleneoxy, C.sub.1 -C.sub.4 alkylenedioxy or halo-C.sub.1 -C.sub.3 alkylenedioxy;R.sub.
    Type: Grant
    Filed: May 11, 1989
    Date of Patent: January 4, 1994
    Assignee: ICI Americas Inc.
    Inventor: Karl J. Fisher
  • 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: 5262082
    Abstract: Fluorine-containing liquid crystal compounds are provided. The compounds comprise a fluorocarbon terminal portion having at least one catenary ether oxygen and a hydrocarbon terminal portion, the terminal portion being connected by a central core, the compounds having smectic mesophases or having latent smectic mesophases.
    Type: Grant
    Filed: April 28, 1992
    Date of Patent: November 16, 1993
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Eugene P. Janulis, Gilbert C. Johnson, Patricia M. Savu, Terence D. Spawn
  • Patent number: 5262086
    Abstract: (R)- and (S)-enantiomer composition represented by the formula (I) having sufficient high optical purity for exhibiting optically tristable states in S*(3) phase; ##STR1## wherein Ra means a C.sub.5 -C.sub.14 alkyl group or a C.sub.5 -C.sub.14 alkoxy group, preferably a C.sub.5 -C.sub.14 alkyl group, Rb means a C.sub.4 -C.sub.12 normal alkyl group or a C.sub.4 -C.sub.12 branched alkyl group, X means a ##STR2## group or a ##STR3## group, Z means a fluorine containing alkyl group, preferably a trifluoromethyl group and * shows an optically active carbon.
    Type: Grant
    Filed: June 26, 1992
    Date of Patent: November 16, 1993
    Assignee: Showa Shell Sekiyu Kabushiki Kaisha
    Inventors: Yoshiichi Suzuki, Horiyuki Mogamiya, Ichiro Kawamura
  • Patent number: 5260475
    Abstract: The hydroxybenzoic acids, e.g., salicylic acid and parahydroxybenzoic acid, are esterified by reacting same with a halocarbon, advantageously a halogenated derivative of an aliphatic, cycloaliphatic, cyclo- or arylaliphatic hydrocarbon, in essentially homogeneous liquid phase and in the presence of a nonquaternizable tertiary amine.
    Type: Grant
    Filed: June 24, 1991
    Date of Patent: November 9, 1993
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jean-Roger Desmurs, Serge Ratton
  • Patent number: 5248817
    Abstract: A novel procedure for bromination of aromatic moieties utilizes N-bromosuccinimide or dibromodimethylhydantoin in an aqueous alkali medium. The bromination procedure is employed for the preparation of an intermediate used in the preparation of remoxipride, an antipsychotic compound.
    Type: Grant
    Filed: July 8, 1992
    Date of Patent: September 28, 1993
    Assignee: Merck & Co., Inc.
    Inventors: Joseph Auerbach, Steven A. Weissman
  • 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: 5236620
    Abstract: Derivatives of difluorobenzene of the formula IR.sup.1 --(--A.sup.o --).sub.m --Z.sup.1 --A.sup.1 --Z.sup.2 --A.sup.2 --R.sup.2 Iwherein R.sup.1, R.sup.2, A.sup.o, A.sup.1, A.sup.2, Z.sup.1, Z.sup.2 and m have the meaning indicated in patent claim 1, their preparation and their use as components of liquid-crystal media.
    Type: Grant
    Filed: May 15, 1989
    Date of Patent: August 17, 1993
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Volker Reiffenrath, Joachim Krause, Andreas Wachtler, Georg Weber, Thomas Geelhaar
  • 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: 5230827
    Abstract: Derivatives of 2,3-Difluorobenzoic acid compounds of the formula I ##STR1## in which R.sup.1 and R.sup.2, independently of one another, are each an alkyl group having 1 to 15 C atoms, in which, in addition, one or two non-adjacent CH.sub.2 groups may be replaced by --O--, --CO--, --CH.dbd.CH-- and/or --C.tbd.C--, andA.sup.1 and A.sup.2, independently of one another, are each 1,4-phenylene which is unsubstituted or substituted by one or two fluorine atoms, and in which, in addition, one or two CH groups may be replaced by N, or are trans1,4-cyclohexylene, or one of the two A.sup.1 and A.sup.2 groups is alternatively a single bond,are suitable as components of liquid-crystalline phases.
    Type: Grant
    Filed: May 12, 1989
    Date of Patent: July 27, 1993
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Volker Reiffenrath, Joachim Krause, Andreas Wachtler, Georg Weber, Thomas Geelhaar
  • Patent number: 5230826
    Abstract: Compounds of the formula ##STR1## wherein X.sup.1 denotes fluorine or chlorine and X.sup.2 denotes hydrogen, fluorine or chlorine; R.sup.1 is 3E-alkenyl, 4-alkenyl, 2E-alkenyloxy or 3-alkenyloxy; n stands for the number 0 or 1; one of the groups Y.sup.1 and Y.sup.2 is a single covalent bond, --COO--, --OOC--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O-- or --OCH.sub.2 -- and the other of the groups Y.sup.1 and Y.sup.2 is a single covalent bond; and rings A.sup.1 and A.sup.2 each individually are substituted or unsubstituted trans-1,4-cyclohexylene, in which optionally 2 non-adjacent CH.sub.2 groups are replaced by oxygen, or substituted or unsubstituted 1,4-phenylene, in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen; with the proviso that X.sup.2 denotes fluorine or chlorine and/or Y.sup.1 or Y.sup.2 denotes --CH.sub.2 O-- or --OCH.sub.2 -- when simultaneously X.sup.1 is fluorine and R.sup.1 is 3E-alkenyl,and their use for liquid crystalline mixtures and electro-optical purposes.
    Type: Grant
    Filed: October 26, 1988
    Date of Patent: July 27, 1993
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Arthur Boller, Richard Buchecker, Martin Schadt, Alois Villiger
  • Patent number: 5231183
    Abstract: A process for producing an enyne derivative, and intermediate, which is useful for preparing compounds showing strong inhibiting activities against squalane.epoxidase of Eumycetes and strong anti-cholesterol activities. The process comprises reacting a compound of the formula:Z--CH.sub.2 --CH.dbd.CH--W [I]wherein W is a halogen atom, and Z is a leaving group, with an amine in the presence of a base, if necessary, to obtain a compound of the formula: ##STR1## then reacting an acetylene derivative to this compound in the presence of a palladium catalyst, to obtain a compound of the formula: ##STR2## and, if necessary, N-alkylating this compound.
    Type: Grant
    Filed: March 27, 1992
    Date of Patent: July 27, 1993
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Susumu Nakagawa, Akira Asai, Satoru Kuroyanagi, Makoto Ishihara, Yoshiharu Tanaka
  • 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: 5217644
    Abstract: A mesomorphic compound represented by the following formula (I): ##STR1## wherein R.sup.1 denotes analkyl group having 1-18 carbon atoms; R.sup.2 denotes an alkyl group having 1-12 carbon atoms; A and B respectively denote ##STR2## Z.sup.1 and Z.sup.2 respectively denote --H, 'CH.sub.3, --OCH.sub.3, --CN or halogen; m and n respectively denote 0, 1 or 2 and p denotes 1 or 2 with proviso that m+n+p =2 or 3; X denotes a single bond, ##STR3## denotes an asymmetric carbon atom.
    Type: Grant
    Filed: January 29, 1991
    Date of Patent: June 8, 1993
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiroyuki Nohira, Yoko Yamada, Shinichi Nakamura, Akira Sakaigawa, Yasumasa Tashiro, Yoshio Aoki
  • Patent number: 5211879
    Abstract: This invention provides novel ester compounds represented by the following general formula (1): ##STR1## (wherein R.sup.1 and R.sup.2 are alkyl groups and may be the same or not, A and B are selected from a single bond and --COO--, X is selected from ##STR2## optically active bodies thereof and liquid crystal compositions containing at least one of these compounds.
    Type: Grant
    Filed: October 29, 1990
    Date of Patent: May 18, 1993
    Assignee: Nippon Mining Co., Ltd.
    Inventors: Nobuyuki Shiratori, Isa Nishiyama, Atsushi Yoshizawa, Toshihiro Hirai
  • Patent number: 5208388
    Abstract: 2,2-Difluorocyclopropyl derivatives of the formula ##STR1## in which R represents alkyl, optionally substituted aryl or optionally substituted aralkyl andX represents hydroxymethyl, 2-hydroxyethyl, isocyanato, amino, amino hydrohalide or a radical of the formula --CO--R.sup.1, whereR.sup.1 represents hydrogen, hydroxyl, alkoxy, alkyl, halogen or amino,are intermediates for fungicides.
    Type: Grant
    Filed: September 20, 1991
    Date of Patent: May 4, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Rudolf Gassen, Bernd Baasner
  • Patent number: 5207947
    Abstract: Liquid crystal compound of the formula ##STR1## wherein R.sub.1 and R.sub.2 each is a C.sub.1-18 alkyl group or an aralkyl group, R' is a haloalkyl group, X is --0--, --CO--, --COO-- or direct bond, Y is --COO--, --OCO-- or --CH.sub.2 O--, (A) and (B) each is ##STR2## and p and l each is zero or one.
    Type: Grant
    Filed: June 11, 1991
    Date of Patent: May 4, 1993
    Assignee: Showa Shell Sekiyu Kabushiki Kaisha
    Inventors: Yoshiichi Suzuki, Noriko Yamakawa, Yoshihiko Aihara, Hiroyuki Mogamiya, Toru Ooide, Tadaaki Isozaki, Yuvra Negi, Shigenori Sakuma
  • 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: 5204018
    Abstract: Compounds of the formula ##STR1## wherein n stands for the number 0 or 1; R.sup.1 denotes a group R.sup.3 or R.sup.3 --A.sup.3 --Z.sup.2 -- and R.sup.2 denotes a group R.sup.4 or R.sup.4 --A.sup.4 --Z.sup.3 --; ring A.sup.1 signifies unsubstituted or halogen-, cyano- and/or methyl-substituted 1,4-phenylene in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen; A.sup.3, A.sup.4 and ring A.sup.2 each independently represent unsubstituted or halogen-, cyano- and/or methyl-substituted 1,4-phenylene in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen or trans-1,4-cyclohexylene, trans-1,3-dioxane-2,5-diyl, 1-cyano-trans-1,4-cyclohexylene, bicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, tetralin-2,6-diyl or trans-decalin-2,6-diyl; Z.sup.1, Z.sup.2 and Z.sup.3 each independently signify a single covalent bond, --COO--, --OOC--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.tbd.C--, --(CH.sub.2).sub.3 O--, --O(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 -- or the trans form of --CH.
    Type: Grant
    Filed: January 22, 1991
    Date of Patent: April 20, 1993
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Stephen Kelly
  • Patent number: 5204019
    Abstract: 4-Q.sup.1 -4'-Q.sup.2 -2,3-Difluorobiphenyls whereinQ.sup.1 and Q.sup.2 independently of one another are each R or R-A.sup.1 -A.sup.2 -Z in whichR (sic) alkyl having 1-15 C atoms or alkenyl having 3-15 C atoms each of which is unsubstituted or monosubstituted by cyano or at least monosubstituted by fluorine or chlorine, and in which in each case one or two non-adjacent CH.sub.2 groups can also be replaced by --O--, --CO--, --O--CO, --CO--O-- or --O--COO--, (sic) --COO--, --O--CO--, --CH.sub.2 O, --O--CH.sub.2 --, --CH.sub.2 CH.sub.2 -- or a single bond, andA.sup.1 and A.sup.2 independently of one another . . (sic) each 1,4-phenylene which is unsubstituted or substituted by one or two fluorine atoms, and in which one or two CH groups can also be replaced by N, or trans-1,4-cyclohexylene wherein one or two non-adjacent CH.sub.2 groups can also be replaced by --O--, and one of the two groups A.sup.1 and A.sup.2 can also be a single bond,subject to the proviso that Z is --CO--O, --O--CO--, --CH.sub.2 O--, --OCH.
    Type: Grant
    Filed: May 15, 1989
    Date of Patent: April 20, 1993
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Volker Reiffenrath, Joachim Krause, Andreas Wachtler, Georg Weber, Ulrich Finkenzeller, David Coates, Ian C. Sage, Simon Greenfield, George W. Gray, Michael Hird, David Lacey, Kenneth J. Toyne
  • Patent number: 5204454
    Abstract: Prepolymer polyols containing mesogenic moieties useful as reactants for the preparation of resinous materials are disclosed. Synthesized by condensing a polyether polyol with bifunctional mesogenic diacids, or diesters, the compounds of the invention are characterized by their reasonably low melt temperature which renders them suitable as additive materials in polymeric molding compositions and as precursors for the preparation of resinous materials.The liquid crystalline properties of the prepolymers of the invention were found to depend on the type and molecular weight of the glycols and on the molar ratio between the glycols and the mesogenic reactant.
    Type: Grant
    Filed: July 19, 1991
    Date of Patent: April 20, 1993
    Assignee: Miles Inc.
    Inventors: Randall A. Rodenhouse, Dittmar K. Nerger, Douglas A. Wicks
  • Patent number: 5204020
    Abstract: Liquid crystal compounds represented by the formula; ##STR1## in which Ra means an alkyl group of 1-20 carbon atoms or an alkoxy group of 1-20 carbon atoms; Rb means an aliphatic alkyl group, a branched alkyl group or an aralkyl group respectively of 1-20 carbon atoms, an alkoxy group of 1-20 carbon atoms, or an alkanoyl methyl group having 1-20 carbon atoms in the alkyl; ##STR2## Z means a fluorinated alkyl or a fluorinated haloalkyl; m is an integer of from 1 to 3; n is an integer of from 0 to 2 where when n is 0, Y is a single bond; and * shows an optically active center, which have a larger spontaneous polarization, high speed of response and good orientation, and show tristable liquid crystal phase.
    Type: Grant
    Filed: April 29, 1992
    Date of Patent: April 20, 1993
    Assignee: Showa Shell Sekiyu K.K.
    Inventors: Yoshiichi Suzuki, Hiroyuki Mogamiya, Ichiro Kawamura
  • Patent number: 5200550
    Abstract: Bi-aromatic esters have the formula ##STR1## wherein R.sub.1 represents H, OH, --CH.sub.3, --CH.sub.2 OH, --CH(OH)CH.sub.3, --COOR.sub.9, ##STR2## or SO.sub.2 R.sub.10 ; R.sub.9 represents H, C.sub.1 -C.sub.6 alkyl or monoor polyhydroxyalkyl; R.sub.10 represents OH, C.sub.1 -C.sub.6 alkyl or ##STR3## r' and r" represent H, C.sub.1 -C.sub.6 alkyl, aryl, aralkyl, mono or polyhydroxyalkyl, or r' and r" taken together form a heterocycle; R.sub.2 represents H, C.sub.1 -C.sub.6 alkyl, OR.sub.9, F or --CF.sub.3 ; R.sub.3, R.sub.4 and R.sub.5 represent H, F, OH, --CH.sub.3, --OCH.sub.3, --CF.sub.3, --COOH or --CH.sub.2 OH; R.sub.6 and R.sub.8 represent H, .alpha.-substituted C.sub.3 -C.sub.15 alkyl, .alpha.,.alpha.'-disubstituted C.sub.4 -C.sub.12 alkyl, C.sub.3 -C.sub.12 cycloalkyl, C.sub.5 -C.sub.12 mono or polycyclic cycloalkyl whose linking carbon is trisubstituted, --SR.sub.11, --SO.sub.2 R.sub.11 or --SOR.sub.11 ; R.sub.11 represents C.sub.1 -C.sub.6 alkyl or cycloalkyl; R.sub.6 and R.sub.
    Type: Grant
    Filed: July 17, 1990
    Date of Patent: April 6, 1993
    Assignee: Centre International de Recherces Dermatologiques Galderma (Cird Galderma)
    Inventors: Braham Shroot, Jean-Michel Bernardon
  • 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: 5190692
    Abstract: Four ring esters and ethers of formula I ##STR1## wherein R.sup.1 and R.sup.2 independently from each other are alkyl or alkenyl with up to 9 carbon atoms or such residues wherein one CH.sub.2 group is replaced by oxygen,m and n are each 1 or 2, the sum of m and n being 3,X.sup.1 and X.sup.2 are each hydrogen or fluorine, andQ is --CH.sub.2 -- or --CO--with the proviso that in case m=2 Q is --CH.sub.2 -- and/or at least one of X.sup.1 and X.sup.2 is F are suitable as components of liquid crystal media.
    Type: Grant
    Filed: March 13, 1990
    Date of Patent: March 2, 1993
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: David Coates, Simon Greenfield
  • 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: 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: 5183934
    Abstract: Disclosed is a novel compound 2-trifluoromethyl-4-hydroxybenzoic acid represented by the formula: ##STR1##
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: February 2, 1993
    Assignee: Showa Shell Sekiyu Kabushiki Kaisha
    Inventor: Yoshiichi Suzuki
  • Patent number: 5167696
    Abstract: A compound of formula (I): ##STR1## in which Ar is an optionally substituted aryl or heterocyclic ring system; W is O or NR.sup.1 where R.sup.1 is hydrogen or lower alkyl;A is .dbd.CH or >CH.sub.2 and G is .dbd.C--R.sup.2, >CR.sup.3 R.sup.4 or >C.dbd.R.sup.5 such that --G--A-- is --CR.sup.2 .dbd.CH--, where R.sup.2 is H or CR.sup.6 R.sup.7 XR.sup.8 ; or --G--A-- is CR.sup.3 R.sup.4 --CH.sub.2 where CR.sup.3 R.sup.4 is CH--CR.sup.6 R.sup.7 XR.sup.8, CH--OCR.sup.6 R.sup.7 XR.sup.8, C(R.sup.9)OCOR.sup.10, CR.sup.9 R.sup.10, C(R.sup.9)OR.sup.10, C(OR.sup.9)OR.sup.10, or CH--CH.sub.2 (CO.sub.2 R.sup.11); or --G--A-- is --CR.sup.5 --CH.sub.2 -- where R.sup.5 is .dbd.CR.sup.7 XR.sup.8, .dbd.NOCR.sup.6 R.sup.7 XR.sup.8, .dbd.NOR.sup.11 or .dbd.NOCOR.sup.11 ;X is (CH.sub.2).sub.n, CH.dbd.CH, CH(OR.sup.20)CH.sub.2, or COCH.sub.2 ;n is 0, 1 or 2;R.sup.6 and R.sup.7 are independently selected from H, optionally substituted alkyl, alkenyl or alkynyl, halogen, NR.sup.9 R.sup.10, or R.sup.6 and R.sup.
    Type: Grant
    Filed: February 7, 1991
    Date of Patent: December 1, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Ewan J. T. Chrystal, John E. D. Barton, David Cartwright
  • Patent number: 5167861
    Abstract: Novel ferroelectric liquid crystal compounds showing three stable liquid crystal states so as to give particular optical response wave shape as well as particular optical and electric responses to impressed voltage of triangle wave shape in comparison with usual ferroelectric liquid crystals of bistable phase, whereby it is possible to provide electrooptical devices having larger picture area at lower cost. Typical compounds are represented by ##STR1## wherein n is an integer of 3-18 and m is an integer of 5-12.
    Type: Grant
    Filed: July 7, 1989
    Date of Patent: December 1, 1992
    Assignee: Showa Shell Sekiyu K.K.
    Inventors: Yoshiichi Suzuki, Takashi Hagawara
  • Patent number: 5166404
    Abstract: Oxydiphthalic acid esters of the formula ##STR1## where Z is H or alkyl, and X is halo, X' is H or halo, or X and X' together represent an oxygen atom; are prepared by the esterification reaction of the corresponding halo-oxydiphthalic anhydride or dioxydiphthalic anhydride with an alkanol.
    Type: Grant
    Filed: October 4, 1991
    Date of Patent: November 24, 1992
    Assignee: Occidental Chemical Corporation
    Inventors: Jeffrey S. Stults, Willis T. Schwartz, Frank J. Dinan
  • Patent number: 5156763
    Abstract: Laterally fluorinated 4-cyanophenyl and 4'-cyanobiphenyl benzoates are diosed of general formula I: ##STR1## in which R is R.sup.1 or R.sup.1 O, wherein R.sup.1 is C.sub.1 -C.sub.12 alkyl, m and n are 0 or 1 provided that (n+m) is 0 or 1, each of a, b, c and d are independently 0 or 1, provided (a+b+c+d) is not zero, but excluding the case where a and b are 0 and one of c and d is 0, being useful constituents of nematic liquid crystal materials.
    Type: Grant
    Filed: August 30, 1990
    Date of Patent: October 20, 1992
    Assignee: The Secretary of State for 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, Michael Hird, Damien G. McDonnell
  • 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: 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: 5131945
    Abstract: Compounds of formula I ##STR1## are useful as herbicides, effective against dicotyledonous weeds.
    Type: Grant
    Filed: July 13, 1990
    Date of Patent: July 21, 1992
    Assignee: Shell Research Limited
    Inventors: Hans-Joachim Bissinger, Ludwig Schoeder, Helmut Baltruschat, Manfred Garrecht, Erich Raddatz, Wolfgang Fruhstorfer
  • Patent number: 5130475
    Abstract: Disclosed herein is a derivative of 1,5-diphenyl-1H-1,2,4-triazole-3-carboxamide represented by the following formula (I): ##STR1## wherein R represents an alkyl group of 2 to 10 carbon atoms, which is substituted by fluorine atom(s), and X represents a hydrogen atom or a fluorine atom, a process for producing the derivative and a herbicidal compositions containing the derivative of 1,5-diphenyl-1H-1,2,4-triazole-3-carboxamide as an active ingredient.
    Type: Grant
    Filed: November 26, 1991
    Date of Patent: July 14, 1992
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Takafumi Shida, Hideo Arabori, Takeo Watanabe, Shiro Yamazaki, Hiroyasu Shinkawa