Halogen In Acid Moiety Patents (Class 560/65)
  • Patent number: 5130454
    Abstract: Polytetrahydrofuran derivatives of the general formula ##STR1## where n is from 2 to 70, X is the bridge member --NH-- or --O-- and R.sup.1 and R.sup.4 are each hydrogen or various radicals.
    Type: Grant
    Filed: December 19, 1990
    Date of Patent: July 14, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Eckhard Hickmann, Ulrich Koehler, Hardo Siegel
  • Patent number: 5128062
    Abstract: An optically active compound of the formula: ##STR1## wherein R is alkyl or alkoxy, R* is an optically active alkyl group, X is alkyl or halogen, Y is a single bond ##STR2## and C* is an asymmetric carbon, is chemically stable and shows or induces large spontaneous polarization and is useful in a chiral liquid crystal composition.
    Type: Grant
    Filed: June 6, 1990
    Date of Patent: July 7, 1992
    Assignees: Wako Pure Chemical Industries, Ltd., Nippon Telegraph and Telephone Corporation
    Inventors: Shogo Kobayashi, Shigeki Ishibashi, Fumiyoshi Urano, Takaaki Negishi
  • 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: 5114613
    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 groups 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: September 13, 1989
    Date of Patent: May 19, 1992
    Assignee: Canon Kabushiki Kaisha
    Inventors: Kazuo Yoshinaga, Kazuharu Katagiri, Akira Tsuboyama, Hiroyuki Kitayama, Kenji Shinjo, Chieko Hioki
  • 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: 5110498
    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 or an aralkyl group having from 7 to 18 carbon atoms; R.sub.2 represents an alkenyl group having from 1 to 18 (preferably from 3 to 14) carbon atoms; R.sub.3 represents CF.sub.3 or C.sub.2 F.sub.5 ; X represents a single bond, --O--, --COO--, or --OCO--; Y represents --COO--, --OCO--, --CH.sub.2 O--, or --OCH.sub.2 --; A and B each represents a cyclic group; and * indicates an optically active center.The compound of formula (I) exhibits three stable states of molecular orientation.
    Type: Grant
    Filed: December 27, 1990
    Date of Patent: May 5, 1992
    Assignee: Showa Shell Sekiyu K.K.
    Inventors: Yoshiichi Suzuki, Shigenori Sakuma, Noriko Yamakawa
  • 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: 5095147
    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: April 26, 1991
    Date of Patent: March 10, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Rudolf Gassen, Bernd Baasner
  • Patent number: 5086067
    Abstract: This invention relates to a compound of the formula: ##STR1## or a pharmaceutically acceptable salt thereof wherein X is oxygen, sulfur, --CH.dbd.CH-- or --CH.dbd.N--; wherein R.sub.1 is alkyl, alkenyl or alkynyl of about 1 to 20 carbon atoms; wherein R is --CO.sub.2 R.sup.2, tetrazole, methylsulfonamide or benzenesulfonamide, wherein R.sup.2 is hydrogen, alkyl of 1 to 6 carbon atoms or a pharmaceutically acceptable cation and R.sup.3 is hydroxyl or halogen, having utility as LTB.sub.4 synthesis inhibitors.
    Type: Grant
    Filed: December 18, 1989
    Date of Patent: February 4, 1992
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Richard A. Haack, Julie M. Miyashiro
  • Patent number: 5082589
    Abstract: Compounds of the formula ##STR1## wherein m represents is the number of 0 to 1; A is a single convalent bond, --CH.sub.2 --CH.sub.2 --, --OCH.sub.2 --, --COO-- or --OOC--; rings B, C and D are 1,4-phenylene optionally substituted with cyano, halogen or lower alkyl; Y.sup.1 and Y.sup.2 are hydrogen or one of them also is cyano; and R.sup.1 and R.sup.2 each represents C.sub.1 -C.sub.18 -alkyl or C.sub.2 -C.sub.18 alkenyl, either of which is optionally halogen-substituted, in which one CH.sub.2 group or two non-adjacent CH.sub.2 groups is/are optionally replaced by oxygen: with the provisos that at least one of R.sup.1 and R.sup.2 has a chiral carbon atom or R.sup.1 is straight-chain C.sub.4-18 -alkoxy and R.sup.2 is straight C.sub.3-18 -alkyl or a C--C double bond or both when A is --COO-- and at least one of R.sup.1 and R.sup.
    Type: Grant
    Filed: February 27, 1990
    Date of Patent: January 21, 1992
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Richard Buchecker, Hans-Jurgen Fromm, Stephen Kelly, Martin Schadt
  • Patent number: 5081283
    Abstract: Novel intermediates for fungicides, comprising fluorocyclopropyl derivatives of the formula ##STR1## in which R represents alkyl, optionally substituted aryl or optionally substituted aralkyl,X represents hydrogen, chlorine or bromine andR.sup.1 represents hydroxyl, alkoxy, alkyl or halogen.
    Type: Grant
    Filed: April 26, 1991
    Date of Patent: January 14, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Rudolf Gassen, Bernd Baasner
  • Patent number: 5079245
    Abstract: The compounds 2-trifluoromethyl-7-substituted-6,7,8,9-tetrahydro-[5H]-benzocycloheptenes are disclosed and disclosed to be useful in the treatment of metabolic illnesses such as diabetes, obesity, and their complications. A perferred compound is 2-trifluoromethyl-7-amino-6,7,8,9-tetrahydro-[5H-benzocycloheptane.
    Type: Grant
    Filed: July 5, 1989
    Date of Patent: January 7, 1992
    Assignee: Adir et Compagnie
    Inventors: Michel Wierzbicki, Pierre Hugon, Jacques Duhault, Francoise Lacour
  • 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: 5072022
    Abstract: The invention relates to a novel herbicide composition, which comprises the (S) enantiomer or racemate of a compound of the general formula (I), ##STR1## wherein R stands for a methyl or ethyl group, as active ingredient in an amount of 0.01 to 95% by weight together with one or more solid and/or liquid carrier(s), preferably grist(s) of native or synthetic material(s) and/or with inert solvents(s), preferably xylene(s) and/or cyclohexanone; and optionally with surface active agents(s), preferably anionic and/or nonionic emulsifying or dispersing agent(s).The invention further relates to the above compounds of the general formula (I) as well as to a process for the preparation thereof.The compounds according to the invention possess an outstanding herbicidal effect (over 90%) and advantageous selectivity threshold values against cultivated plants.
    Type: Grant
    Filed: December 21, 1989
    Date of Patent: December 10, 1991
    Assignee: Budapest Vegyimuvek
    Inventors: Jozsef Bakos, Balint Heil, Imre Toth, Bela des, Istvan Gebhardt, Ferenc Bihari, Anna Durkonee Ponacz, Gyula Eifert, Jeno Kiraly, Eva Konok nee Horvath, Laszlo Lukacs, Agnes Meszaros nee Szekrenyesi, Bela Radvany, Lajos Sarosi
  • 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: 5066673
    Abstract: Substituted benzyl 2-phenylalk(en)-1-ylcyclopropanecarboxylates of the general formula I ##STR1## where R.sup.1 is halogen or in each case low molecular weight, alkyl, alkoxy, haloalkyl or haloalkoxy (n=1 to 5),R.sup.2 is halogen or, in each case low molecular weight, alkyl or haloalkyl,R.sup.3, R.sup.4 are halogen or each is an electron in a double bond formed by them together,R.sup.5 is hydrogen or, in each case low molecular weight, alkyl, alkenyl, alkynyl or cyano,R.sup.6 is halogen or alkyl (n=1 to 4),R.sup.7 is halogen (p=0 to 25),and their use for combating pests.
    Type: Grant
    Filed: February 22, 1990
    Date of Patent: November 19, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Winfried Zombik, Hans Theobald, Bernd Wolf, Ludwig Schuster, Peter Hofmeister, Christoph Kuenast
  • 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: 5045229
    Abstract: Difluoromethylene compounds of the formula IR.sup.1 --(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --Q--CF.sub.2 --(A.sup.3 --Z.sup.2).sub.n --A.sup.4 --R.sup.2 Iin which R.sup.1, R.sup.2, A.sup.1, A.sup.2, A.sup.3, A.sup.4, Z.sup.1, Z.sup.2, m and n are as defined herein and Q is --CO--, --O-- or --S--, can be used as components of liquid-crystalline media for liquid-crystal and electrooptical display elements.
    Type: Grant
    Filed: March 16, 1990
    Date of Patent: September 3, 1991
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Ekkehard Bartmann, Reinhard Hittich, Hans-Adolf Kurmeier, Eike Poetsch, Herbert Plach
  • Patent number: 5026899
    Abstract: The invention relates to novel 2-acyl-1,3-cyclohexanediones and the oxime ethers thereof with herbicidal and plant growth regulating properties.The novel 2-acyl-1,3-cyclohexanediones and the oxime ethers thereof are of the formula I ##STR1## wherein A is a 2- or 7-membered alkylene bridge, or a 3- to 7-membered alkenylene bridge which may be mono- or polyunsaturated,n is 0, 1 or 2,R.sub.1 is C.sub.1 -C.sub.4 alkyl or benzyl,R.sub.2 is C.sub.1 -C.sub.6 alkyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; or is C.sub.3 -C.sub.6 cycloalkyl; or phenyl, benzyl or phenylethyl, the phenyl ring of each of which may be substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, cyano or nitro,X is oxygen or a radical --NOR.sub.3, andR.sub.3 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl or C.sub.3 -C.
    Type: Grant
    Filed: December 13, 1989
    Date of Patent: June 25, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Hans Tobler
  • Patent number: 5026895
    Abstract: The invention relates to novel fungicidally active compounds, a process for the preparation thereof, composition comprising the said composition as active ingredient and their use for agricultural purpose.The novel (trifluoromethyl)-phenoxy benzoic acid derivate can be described by formula (I), ##STR1## wherein X is hydrogen or halogen, preferably chlorine, nitro or trifluoromethyl,Y is hydrogen or halogen, preferably chlorine,Z is hydrogen, trifluoromethyl or nitro,V is hydrogen, halogen, preferably chlorine, or nitro,W is hydrogen, nitro or trifluoromethyl,R.sub.1 is alkyl having 1-4 carbon atoms, preferably ethyl, hydrogen, alkali metal, preferably sodium, potassium, or ammonium or ammonium-ion having a formula (II),NH.sub.3.sup.+ R.sub.2 (II)whereinR.sub.
    Type: Grant
    Filed: November 12, 1985
    Date of Patent: June 25, 1991
    Assignee: Budapesti Vegyimuvek
    Inventors: Jozsef Bakos, Balint Neil, Laszlo Kollar, Szilard Toros, Gvula Eifert, Ferenc Bihari, Peter Boros, Anna Durko nee Ponacz, Istvan Kuronya, Istvan Magyari, Judit Timar, Peter Bohus, Laszlo Wohl
  • Patent number: 5026896
    Abstract: Novel trisubstituted benzoic acid intermediates which are useful in the preparation of certain herbicidal 2-(2,3,4-trisubstituted benzoyl)-1,3-cyclohexanediones are described.
    Type: Grant
    Filed: May 8, 1990
    Date of Patent: June 25, 1991
    Assignee: ICI Americas Inc.
    Inventor: William J. Michaely
  • Patent number: 5025017
    Abstract: Seco-mevinic acid derivatives are provided which has the structure ##STR1## including all stereoisomers thereof, wherein Z is ##STR2## R is H, alkali metal or lower alkyl, R.sup.1 is H, lower alkyl, aryl, lower alkoxy, cycloalkyl, heteroaryl, aralkyl, heteroaralkyl or heterocyclic; R.sup.2 is lower alkyl, cycloalkyl or aralkyl, and X is O or NR.sup.5 wherein R.sup.5 is H or lower alkyl, and are HMG CoA reductase inhibitors and thus are useful as antihypercholesterolemic agents and in treating atherosclerosis. New intermediates for preparing the above seco-mevinic acid derivatives are also provided.
    Type: Grant
    Filed: September 28, 1989
    Date of Patent: June 18, 1991
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Donald S. Karanewsky
  • Patent number: 5025036
    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 cycloalkyl, 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: May 3, 1989
    Date of Patent: June 18, 1991
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Matthew Carson, Ru-Jen L. Han, Ronald A. LeMahieu
  • Patent number: 5019298
    Abstract: Disclosed are optically active aromatic carboxylic acid derivatives represented by the formula (I): ##STR1## (wherein R.sub.2 represents an alkoxyalkyl group having 1 to 20 carbon atoms or an alkyl group having 1 to 20 carbon atoms, which alkyl group may be substituted with a halogen atom; represents a number of 1 or 2; m represents a number of 0 or 1; and * indicates asymmetric carbon atom) and a process for producing such derivatives through the following reaction steps: ##STR2## The optically active aromatic carboxylic acid derivatives represented by the above-described formula (I) are useful as a liquid crystal material and can be also utilized as an intermeidate for the preparation of pharmaceuticals, agricultural chemicals and the like.
    Type: Grant
    Filed: April 25, 1988
    Date of Patent: May 28, 1991
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masayoshi Minai, Takayuki Higashii
  • Patent number: 5013476
    Abstract: A ferroelectric liquid crystal mixture containing at least one compound of the formula ##STR1## wherein n stands for the number 0 or 1; X.sup.1 represents a single covalent bond, --COO-- or --OOC-- and X.sup.2 represents a single covalent bond, --COO--, --OOC--, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 -- or --CH.sub.2 O--; rings A.sup.1, A.sup.2 and A.sup.3 each independently signify 1,4-phenylene optionally substituted with cyano, halogen or lower alkyl or pyrimidin-2,5-diyl, pyrazin-2,5-diyl, when n is 1, trans-1,4-cyclohexylene or trans-m-dioxan-2,5-diyl; with the proviso that one of the rings present stands for pyrimidin-2,5-diyl or pyrazin-2,5-diyl when a further ring signifies trans-1,4-cyclohexylene or when n stands for the number 0 and X.sup.1 stands for a single covalent bond; and R.sup.1 signifies an optionally halogen-substituted alkenyl group with up to 18 carbon atoms in which optionally 1 or 2 non-adjacent CH.sub.2 groups are replaced by --O-- and/or a C.dbd.C double bond; with the proviso that R.
    Type: Grant
    Filed: November 17, 1987
    Date of Patent: May 7, 1991
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Arthur Boller, Richard Buchecker, Hans-Jurgen Fromm, Stephen Kelly, Martin Schadt, Alois Villiger
  • Patent number: 5010105
    Abstract: Compounds of Formula (I) and (II): ##STR1## are HMG-CoA reductase inhibitors.
    Type: Grant
    Filed: May 9, 1990
    Date of Patent: April 23, 1991
    Assignee: Merck & Co., Inc.
    Inventor: Ta J. Lee
  • Patent number: 5008440
    Abstract: A herbicide composition, which comprises (S)-1'-methoxycarbonylethyl 2-bromo-5-(2-chloro-4-trifluoromethylphenoxy) benzoate or (S)-1'-ethoxycarbonylethyl 2-bromo-5-(2-chloro-4-trifluoromethylphenoxy)benzoate as active ingredient in an amount of 0.01 to 95.0% by weight together with one or more solid and/or liquid carriers, preferably grists of native or synthetic materials; and/or with inert solvents, preferably xylenes and/or cyclohexanone; and optionally with surface active agents, preferably anionic and/or nonionic emulsifying or dispersing agents.
    Type: Grant
    Filed: December 21, 1989
    Date of Patent: April 16, 1991
    Assignee: Budapesti Vegyimuvek
    Inventors: Jozsef Bakos, Balint Heil, Imre Toth, Bela des, Istvan Gebhardt, Ferenc Bihari, Anna Durko nee Ponacz, Gyula Eifert, Jeno Kiraly, Eva Konok nee Horvath, Laszlo Lukacs, Agnes Meszaros nee Szekrenyesi, Bela Radvany, Lajos Sarosi
  • Patent number: 5002960
    Abstract: Compounds of the formulas: ##STR1## wherein Het is an oxazole or oxazine moiety; X is O, S or SO, n is an integer from 3 to 9, Y is an aliphatic bridge; and the various R groups represent hydrogen or various substituents as described herein, are useful as antiviral agents, especially against picornaviruses. N-(Chloroalkyl)amide intermediates for the compounds of Formula I are also active as antiviral agents. Related compounds outside the scope of the above formulas are also disclosed. Also disclosed are novel intermediates, N-halo-alkyl-4-(isoxazol-5-yl)alkoxybenzamides, also useful as antiviral agents.
    Type: Grant
    Filed: June 12, 1989
    Date of Patent: March 26, 1991
    Assignee: Sterling Drug, Inc.
    Inventor: Guy D. Diana
  • Patent number: 5001148
    Abstract: Antihypercholesterolemic activity, due to competitive inhibition of HMG CoA reductase, has been found in compounds of the formula ##STR1## wherein: R.sup.1, R.sup.2 and R.sup.3 are independently selected from:(1) alkyl,(2) substituted alkyl in which one or more substituents are selected from(a) halogen,(b) hydroxyl,(c) alkoxy,(d) alkoxycarbonyl,(e) acyloxy,(f) cycloalkyl,(g) phenyl,(h) substituted phenyl in which one or more substituents are X or Y,(i) alkyl-S(O).sub.n,(j) cycloalkyl-S(O).sub.n,(k) phenyl-S(O).sub.n,(l) substituted phenyl-S(O).sub.n in which one or more substituents are X or Y, and(m) oxo,(3) alkoxy,(4) alkenyl,(5) cycloalkyl,(6) substituted cycloalkyl in which one or more substituents are selected from(a) alkyl,(b) substituted alkyl in which one or more substituents are selected from(i) halogen,(ii) hydroxy,(iii) alkoxy,(iv) alkoxycarbonyl(v) acyloxy(vi) phenyl(vii) substituted phenyl in which one or more substituents are X and Y,(viii) alkyl-S(O).sub.n,(ix) cycloalkyl-S(O).sub.
    Type: Grant
    Filed: June 7, 1989
    Date of Patent: March 19, 1991
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Jeffrey O. Saunders, Eric M. Gordon
  • Patent number: 5001256
    Abstract: Novel trisubstituted benzoic acid intermediates which are useful in the preparation of certain herbicidal 2-(2,3,4-trisubstituted benzoyl)-1,3-cyclohexanediones are described.
    Type: Grant
    Filed: July 31, 1989
    Date of Patent: March 19, 1991
    Assignee: ICI Americas Inc.
    Inventors: William J. Michaely, Jeff K. Curtis
  • Patent number: 4992468
    Abstract: Compounds of the following formula, useful for treating diseases affected by retinoids, are disclosed herein.
    Type: Grant
    Filed: July 26, 1989
    Date of Patent: February 12, 1991
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 4992577
    Abstract: A process for preparing a compound of the formula ##STR1## in which Y is halogen, alkyl or cycloalkyl optionally substituted by halogen or C.sub.1-4 -alkoxy, alkenyl optionally substituted by halogen, aryl, heteroaryl or alkoxycarbonyl,X is hydrogen, halogen or optionally halogen-substituted alkyl, orX and Y, together with the adjacent C atom, form a saturated cycloalkphatic ring having up to 6 C atoms, andR is hydrogen or C.sub.1 -C.sub.4 -alkyl, comprising reacting an aldehyde of the formula ##STR2## with 2-methylbutan-3-one of the formula ##STR3## in the presence of a hydrohalic acid thereby to form a 4,4-dimethyl-3-halogeno-1-hexen-5-one of the formula ##STR4## in which Hal is halogen, halogenating said compound to produce a compound of the formula ##STR5## and reacting said compound with a base of the formulaR--OM (VI)in whichM is one equivalent of an alkali or alkaline earth metal ion.Compounds IV and V are new. By suitable conditions the trans isomer is selectively produced.
    Type: Grant
    Filed: May 22, 1989
    Date of Patent: February 12, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Lantzsch, Dieter Arlt, Manfred Jautelat
  • Patent number: 4966915
    Abstract: An L-dopa derivative represented by formula (I) ##STR1## wherein one of R.sup.1 and R.sup.2 denotes a hydrogen atom and the other denotes a group of formula R--CO-- in which R denotes an alkyl, alkenyl, optionally substituted cycloalkyl, optionally substituted phenyl, optionally substituted aralkyl, lower alkoxy or optionally substituted aralkyloxy group,and its acid addition salt. The compounds are useful in the medical field, especially in the treatment of a series of diseases called Parkinson's disease or Parkinsonism.
    Type: Grant
    Filed: September 16, 1988
    Date of Patent: October 30, 1990
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Yoshimi Tsuchiya, Masahiro Hayashi, Hiroshi Takehana, Akihiro Hisaka, Yoshio Sawasaki, Masaki Ihara
  • 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: 4946865
    Abstract: A compound of the formula: ##STR1## wherein X is a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.3 alkyl group or a C.sub.1 -C.sub.3 alkoxy group and Y is a hydrogen atom, a halogen atom, a cyano group, a formyl group, an ethylene-dioxymethyl group, a hydroxyl group, a hydroxymethyl group or a group of either one of the formulas: --CH.dbd.N--OR.sup.1, --COOR.sup.2, --CONH--R.sup.2 and --CH(OR.sup.3).sub.2 in which R.sup.1 is a hydrogen atom, a C.sub.1 -C.sub.3 alkyl group, a C.sub.3 -C.sub.5 alkenyl group, a C.sub.3 -C.sub.5 alkynyl group, a halo(C.sub.3 -C.sub.5)alkynyl group or a C.sub.1 -C.sub.3 alkyl group substituted with a phenyl group or a cyano group, R.sup.2 is a hydrogen atom, a C.sub.1 -C.sub.3 alkyl group, a C.sub.3 -C.sub.5 alkenyl group or a C.sub.3 -C.sub.5 alkynyl group and R.sup.3 is a C.sub.1 -C.sub.
    Type: Grant
    Filed: December 24, 1986
    Date of Patent: August 7, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Junya Takahashi, Shigeko Nakamura
  • Patent number: 4946845
    Abstract: Psoriasis in mammals is relieved by topically administering naphthalenes of the formula: ##STR1## wherein: R.sup.1 and R.sup.2 are the same and are lower alkoxy or optionally substituted phenoxy,R.sup.3 is lower alkyl, lower alkoxy, or halo and m is 0, 1 or 2 or R.sup.3 is optionally substituted phenyl, optionally substituted phenyl lower alkyl, optionally substituted phenyl lower alkoxy, amino, lower alkylamino, lower dialkylamino, cyano, or S(O).sub.n R wherein R is lower alkyl; optionally substituted phenyl; optionally substituted phenyl lower alkyl; or optionally substituted heterocyclic aryl of three to nine ring atoms containing one or two heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and the pharmaceutically acceptable acid addition salts thereof; and m is 1 and n is 0, 1 or 2;at least one of X or Y is C(O)W and the other X or Y is different and is hydrogen, C(O)W or R.sup.
    Type: Grant
    Filed: November 25, 1988
    Date of Patent: August 7, 1990
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: D. V. Krishna Murthy, Michael C. Venuti, John M. Young
  • 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: 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: 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: 4918213
    Abstract: An optically active, generally mesomorphic compound represented by the following formula (I): ##STR1## wherein R.sub.1 denotes an alkyl group having 1-18 carbon atoms, R.sub.2 denotes an alkyl group having 1-12 carbon atoms; X denotes a single bond, --O--, ##STR2## Y denotes a single bond, ##STR3## --CH.sub.2 O-- or --OCH.sub.2 --; Z denotes --OCH.sub.2 --, ##STR4## respectively denotes ##STR5## C* denotes an asymmetric carbon atom; k, m and n are respectively 0, 1 or 2 with proviso that k+m+n amounts to 2 or 3; and p is 1 or 2.
    Type: Grant
    Filed: July 25, 1988
    Date of Patent: April 17, 1990
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiroyuki Nohira, Masanao Kamei, Hideki Kanazawa, Yoko Yamada, Yuko Etoh
  • 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: 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: 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: 4904814
    Abstract: Process for the preparation of tert-alkyl esters of the formula I ##STR1## in which m is 1 or 2, R is C.sub.4 -C.sub.12 tert-alkyl and X, if m=1, is unsubstituted or halogen-substituted alkyl, cycloalkyl, unsubstituted or substituted aryl or aralkyl, or an aromatic heterocyclic radical and, if m=2, is a direct bond, --CH.sub.2).sub.n, in which n can be an integer from 1 to 8, or 1,2-, 1,3- or 1,4-phenylene, by reaction of an ester of the formula II ##STR2## in which R.sub.1 is methyl or ethyl, with an alcohol ROH in the presence of a catalyst customary for transesterifications.
    Type: Grant
    Filed: February 8, 1988
    Date of Patent: February 27, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Urs Frei, Rudolf Kirchmayr
  • 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: 4866199
    Abstract: An optically active ester compound is provided represented by the following general formula: ##STR1## wherein R.sub.1 is a normal alkyl group having from 6 to 18 carbon atoms; m is zero or one, n is zero or one, and m+n is one or two; X is --CO--O-- or --O--CO--; p is 3 to 6; Y is a hydrogen atom or chlorine atom; R.sub.2 is hydrogen or a normal alkyl group having from 1 to 11 carbon atoms but may be a hydrogen atom only when Y is a chlorine atom; and *C represents an asymmetric carbon atom. The ester compound of the present invention is useful as a ferroelectric liquid crystal compound.
    Type: Grant
    Filed: March 8, 1988
    Date of Patent: September 12, 1989
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Toshihiro Shibata, Masaki Kimura, Norio Kurosawa
  • Patent number: 4855482
    Abstract: The present invention provides a novel bis(phenoxymethyl)benzene derivative or bis(naphthoxymethyl)benzene derivative, which improves the stability of image on a heat sensitive recording paper composed of a leuco dye and a developer.
    Type: Grant
    Filed: June 26, 1987
    Date of Patent: August 8, 1989
    Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo
    Inventors: Ryuzo Ueno, Shinichi Katsura, Yoshirou Uchiyama, Satomi Inoue