Halogen In Acid Moiety Patents (Class 560/62)
  • 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: 5183925
    Abstract: The invention relates to leukotriene-B.sub.4 derivatives of formula I, ##STR1## in which n=1-10,R.sub.1 means radical CH.sub.2 OH, radical COOR.sub.4, radical CONHR.sub.5 or radical CONR.sub.6 R.sub.7,A means a cis, trans or trans, trans--CH.dbd.CH--CH.dbd.CH group or tetramethylene group,B means an alkylene group with up to 10 C atoms,D means a direct compound, oxygen, sulfur, a --C.tbd.C group or a --CH.dbd.CR.sub.8 group,B and D together mean a direct bond,R.sub.2 means a hydrogen atom or an acid radical of an organic acid with 1-15 C atoms andR.sub.3 means a hydrogen atom, an optionally substituted alkyl radical with 1-10 C atoms,a cycloalkyl radical with 3-10 C atoms, an optionally substituted aryl radical with 6-10 C atoms or a 5-6 member heterocyclic radical and if R.sub.4 means a hydrogen atom, their salts with physiologically compatible bases and their cyclodextrin clathrates, process for their production and their pharmaceutical use.
    Type: Grant
    Filed: November 19, 1990
    Date of Patent: February 2, 1993
    Assignee: Schering Aktiengesellschaft
    Inventors: Josef Heindl, Werner Skuballa, Bernd Buchmann, Wolfgang Frohlich, Rolalnd Ederdt
  • Patent number: 5179097
    Abstract: Novel choline salts of non-steroidal anti-inflammatory carboxylic acids and anti-lipidemic carboxylic acids are described. Additionally, blends of choline salts with the above carboxylic acids are also described. The new salts and compositions offer new therapeutic advantages.
    Type: Grant
    Filed: June 10, 1991
    Date of Patent: January 12, 1993
    Inventor: Isaac A. Angres
  • Patent number: 5177244
    Abstract: This invention provides a process and intermediates for preparing 2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylic acids.
    Type: Grant
    Filed: May 7, 1992
    Date of Patent: January 5, 1993
    Assignee: Eli Lilly and Company
    Inventor: Christopher R. Schmid
  • 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: 5145874
    Abstract: Provided are cyclic hydrocarbons of Formula I ##STR1## with an aminoalkyl sidechain that are useful for treating phospholipase A2 mediated conditions, diabetes, and obesity.
    Type: Grant
    Filed: February 25, 1991
    Date of Patent: September 8, 1992
    Assignee: The Upjohn Company
    Inventors: Roy A. Johnson, Gordon L. Bundy, Gilbert A. Youngdale, Douglas R. Morton, Donald P. Wallach, deceased, by Vera M. Wallach, legal representative
  • Patent number: 5130048
    Abstract: The subject application discloses a chiral nonracemic composition of the general formula:R.sub.1 --Ar--O--CH.sub.2 --C*HX--C*HY--CH.sub.2 --O--R.sub.2wherein R.sub.1 is an achiral tail of two to sixteen carbons; Ar is an achiral FLC core of at least two rings; * denotes a chiral carbon; X and Y are halogens; and R.sub.2 is one to ten carbon atoms. The --O--CH.sub.2 --C*HX--C*HY--CH.sub.2 --O-- segment comprises the chiral proximal segment of the chiral tail; the proximal segment is selected from the enantiomers 2R,3R-dihalo and 2S,3S-dihalo. R.sub.2 is the distal segment of the chiral tail.
    Type: Grant
    Filed: July 20, 1990
    Date of Patent: July 14, 1992
    Assignee: Displaytech, Inc.
    Inventors: Michael Wand, William N. Thurmes, David Walba
  • 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: 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: 5120869
    Abstract: A herbicidal compound of formula (I): ##STR1## wherein X is O, S(O).sub.n or NR.sup.a where R.sup.a is H or alkyl and n is 0, 1 or 2;R.sup.1 is H or halo;R.sup.2 is N or CR.sup.3 where R.sup.3 is halo or NO.sub.2 ;R.sup.4 is H, halo, NO.sub.2, alkyl, haloalkyl, CN, CO.sub.2 alkyl, cycloalkyl, phenyl, COalkyl, COphenyl, CHO,OH, NH.sub.2, NHCOalkyl or alkoxyR.sup.5 is H, halo or optionally substituted alkyl;R.sup.6 is H, halo or optionally substituted alkyl; provided that at least one of R.sup.5 and R.sup.6 is halo;R.sup.7 is CN, CHO, COOR.sup.8, CONR.sup.8 R.sup.9, where R.sup.8 is H, optionally substituted alkyl, alkenyl, alkynyl or aryl and R.sup.9 is a group R.sup.8, SO.sub.2 alkyl, NR.sup.10 R.sup.11 or N.sup.+ R.sup.10 R.sup.11 R.sup.12 Z.sup.- where Z is an agriculturally acceptable anion e.g. chloride and R.sup.10, R.sup.11 and R.sup.12 are independently selected from hydrogen and alkyl. Processes for the preparation of these compounds and compositions containing them are also described.
    Type: Grant
    Filed: November 7, 1989
    Date of Patent: June 9, 1992
    Assignee: Imperial Chemical Industries plc
    Inventor: David Cartwright
  • Patent number: 5116987
    Abstract: The invention describes a method of synthesizing a compound of the formula ##STR1## in which X=O or NR,Z=an electron-attracting group,R=H, CN or NO.sub.2,R.sub.1 +R.sub.2 +N--C.dbd.X=a 5-membered or 6-membered heterocycle, andR.sub.3 =H, R.sub.4 =OH or R.sub.3 +R.sub.4 =a bond,said method involving intermediates of the formula ##STR2## in which R.sub.5 =H, Br or N(R.sub.1)CXR.sub.2. This method of synthesis does not involve the epoxide derivative of the chroman.The novel compounds of formula (IX) form a further subject of the invention.
    Type: Grant
    Filed: September 20, 1991
    Date of Patent: May 26, 1992
    Assignee: Sanofi
    Inventors: Georges Garcia, Daniel Mettefeu, Richard Roux
  • 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: 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: 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: 5047172
    Abstract: Novel compounds characterized by increased spontaneous polarization values as one of the important specific features required for ferroelectric liquid crystal compositions, a liquid crystal composition containing the same, and an optical switching element utilizing the composition as a liquid crystal.
    Type: Grant
    Filed: September 19, 1989
    Date of Patent: September 10, 1991
    Assignee: Chisso Corporation
    Inventors: Shinichi Saito, Takashi Inukai, Hiromichi Inoue, Kazutoshi Miyazawa, Kouji Ohno, Makoto Ushioda
  • Patent number: 5043257
    Abstract: Azo dyes of the formula ##STR1## where X is alkyl or alkoxy each of 1 to 4 carbon atoms or halogen, X' is hydrogen, alkyl or alkoxy each of 1 to 4 carbon atoms or halogen, Y and Y' are independently of each other hydrogen or halogen, Z is hydrogen, alkyl or alkoxy or alkylthio each of 1 to 4 carbon atoms, or halogen, M is a 1-, 2- or 3-valent metal cation, ammonium or an organic ammonium compound, m is 1, 2 or 3 and n is 2 to 10, are suitable for use as image dyes in photographic silver dye bleach materials.The dyes of the invention can also be used to dye textile materials.
    Type: Grant
    Filed: December 8, 1989
    Date of Patent: August 27, 1991
    Assignee: Ilford Limited
    Inventors: Kurt Baettig, Gerald C. Jan
  • Patent number: 5041638
    Abstract: An alkenoic acid derivative of the formula ##STR1## in which X and Y are identical or different and represent sulfur, sulfoxide, sulfone, an alkylene chain, --SCH.sub.2 --, or oxygen or a direct bond,W represents --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --,o represents a number 1 to 5,A and B are identical or different and represent carboxyl, carboxymethylene, tetrazolyl or tetrazolylmethylene, or --CO.sub.2 R.sup.9 or --CH.sub.2 CO.sub.2 R.sup.9 or --CONR.sup.10 R.sup.11 or nitrilen represents a number 1 to 10,m represents a number 0 to 7,T and Z are identical or different and represent oxygen or a direct bond andR.sup.2, R.sup.3, R.sup.8 are identical or different and represent hydrogen, alkyl, alkoxy, halogen, trifluoromethyl, trifluoromethoxy, cyano or nitro andR.sup.9 is lower alkyl and R.sup.10 and R.sup.11 are hydrogen, lower alkyl, alkylsulfonyl or arylsulfonyl or together are an alkylene chain to form a ringand pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: May 9, 1989
    Date of Patent: August 20, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ulrich Rosentreter, Harold C. Kluender, Trevor S. Abram, Peter Norman, Steven R. Tudhope
  • Patent number: 5032314
    Abstract: A compound capable of shortening the response time of liquid crystal display elements and a composition containing the same are provided, which compound is expressed by the formula ##STR1## wherein R.sup.1 represents a linear or branched chain alkyl group or alkoxy group, each of 1C-18C; Ar represents ##STR2## wherein X represents H, halogen atom, cyano group or methyl; A represents --COO-- or --CH.sub.2 O--; R.sup.2 represents a C.sub.1 -C.sub.18 alkyl, A C.sub.2 -C.sub.18 alkanoyl, a C.sub.3 -C.sub.18 alkoxycarbonyl or a C.sub.4 -C.sub.18 2-alkoxypropanoyl; C having a symbol * attached thereonto represents asymmetric carbon atom; and when R.sup.
    Type: Grant
    Filed: February 4, 1988
    Date of Patent: July 16, 1991
    Assignee: Chisso Corporation
    Inventors: Makoto Ushioda, Shinichi Saito, Kouji Ohno, Kazutoshi Miyazawa, Hiromichi Inoue
  • Patent number: 5021453
    Abstract: Compounds of formula (I) and (II): ##STR1## are HMG-CoA reductase inhibitors.
    Type: Grant
    Filed: June 6, 1990
    Date of Patent: June 4, 1991
    Assignee: Merck & Co., Inc.
    Inventors: Henry Joshua, Kenneth E. Wilson, Michael S. Schwartz, Ta J. Lee, Gerald E. Stokker
  • Patent number: 5012017
    Abstract: A method for preparing substituted phenoxyphenols which are useful in the preparation of herbicidal (phenoxyphenoxy)propionates is disclosed. The process involves the oxidation of substituted phenoxyphenones to the corresponding phenoxyphenyl esters and their conversion to the desired phenoxyphenol. Novel intermediates for the process are similarly disclosed.
    Type: Grant
    Filed: February 21, 1989
    Date of Patent: April 30, 1991
    Assignee: DowElanco
    Inventors: Jon A. Orvik, Norman R. Pearson, Anthony P. Haag, Timothy J. Adaway, Larry D. Kershner, Andrew S. Kende
  • 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: 5008439
    Abstract: A method for synthesizing 2-(4-hydroxyphenoxy)alkanoic acid esters by reacting a hydroxyaromatic ketone derivative with a 2-substituted alkanoic acid ester under basic conditions and thereafter oxidizing the intermediate with subsequent hydrolysis.
    Type: Grant
    Filed: March 21, 1988
    Date of Patent: April 16, 1991
    Assignee: Hoechst Celanese Corporation
    Inventors: Varadaraj Elango, Kenneth G. Davenport
  • Patent number: 4997591
    Abstract: The chiral smetic liquid-crystalline compounds of the general formula (I)M.sub.1.sup.* --B--M.sub.2.sup.* (I)solidify on cooling from the liquid-crystalline phase in glassy form, as a result of which they are suitable for materials for displaying and storing information. Such materials may be used in electro-optic data stores or display components which are based on the ferroelectric or electroclinic switching effect in a chiral or chirally doped, smetic liquid-crystalline phase.In the general formula, M.sub.1.sup.*, M.sub.2.sup.* stand for chiral smetogenic groups and --B-- is, as bridging link, a typical bivalent group.
    Type: Grant
    Filed: August 11, 1989
    Date of Patent: March 5, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerd Heppke, Feodor Oestreicher
  • Patent number: 4985442
    Abstract: 2-Substituted-1-naphthols are 5-lipoxygenase inhibitors which make them useful in the treatment of inflammation, obstructive lung diseases and/or psoriasis. Useful 2-substituent groups are alkyls, alkenyls, alkynyls, cycloalkyls, cycloalkenyls, the groups CH.sub.2 --C.tbd.C--(CH.sub.2).sub.m R.sup.5 and CH.dbd.CH--(CH.sub.2).sub.n R.sup.5 (where m is 1-4, n is 0-3 and R.sup.5 includes phenyl, COOR.sup.9, where R.sup.9 is H or alkyl of 1-4 carbons, AR.sup.6 (where A is a methylene chain and R.sup.6 is a variety of groups including Cl, Br, I, CHO, CN, COOR.sup.9, NH.sub.2, SC(NH)NH.sub.2, phenyl, P(O)(OR.sup.9).sub.2, etc.), and CHR.sup.7 R.sup.21 (where R.sup.7 is a variety of aromatic and heterocyclic groups and R.sup.21 is H, optionally substituted phenyl and a variety of heterocyclic groups).
    Type: Grant
    Filed: March 23, 1989
    Date of Patent: January 15, 1991
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Douglas G. Batt
  • Patent number: 4983629
    Abstract: 11-Haloprostane derivatives of general Formula I ##STR1## wherein X is F, Cl or Br,R.sub.1 is the residue CH.sub.2 OH or ##STR2## wherein R.sub.2 means a hydrogen atom, an alkyl, cycloalkyl, aryl, phenacyl or heterocyclic residue,A is a --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--group,B is a --CH.sub.2 --CH.sub.2 -- or trans--CH.dbd.CH-- or a --C.tbd.C--group,W is an ethylenedioxymethylene group or a hydroxymethylene group,D and E together mean a direct bond orD is a C.sub.1-10 -alkylene group,E is an oxygen or sulfur atom, a direct bond, a --C.tbd.C--bond or a --CR.sub.6 .dbd.CR.sub.7 -group with R.sub.6 and R.sub.7 meaning a hydrogen atom, a chlorine atom or an alkyl group,R.sub.4 is a hydroxy group,R.sub.5 is a hydrogen atom, an alkyl, a cycloalkyl, an aryl or a heterocyclic group, andthe salts thereof with physiologically compatible bases, processes for their preparation, and use thereof as agents inhibiting gastric acid secretion.
    Type: Grant
    Filed: June 21, 1989
    Date of Patent: January 8, 1991
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Claus-Steffen Sturzebecher, Walter Elger
  • 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: 4913721
    Abstract: Compounds of formula (I): ##STR1## and stereoisomers thereof, wherein V is an oxygen or a sulphur atom; X and Y, which may be the same or different, are hydrogen or halogen atoms, or optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkynyl, haloalkyl, alkoxy, haloalkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted acyloxy, optionally substituted amino, acylamino, nitro, nitrile, --CO.sub.2 R.sup.3, --CONR.sup.4 R.sup.5, or --COR.sup.6 groups; or the groups X and Y, when they are in adjacent positions on the phenyl ring, may join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; and Z is optionally substituted methylene, optionally substituted amino, oxygen or sulphur and when Z is a substituted methylene group, the substituent may join the 2-position of the phenyl ring to form a non-aromatic fused ring; R.sup.1 and R.
    Type: Grant
    Filed: October 31, 1988
    Date of Patent: April 3, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Christopher R. A. Godfrey
  • Patent number: 4902334
    Abstract: A plant metabolism regulating agent comprising as an active ingredient an alpha,beta or beta,gamma-un-saturated carboxylic acid or its derivative. It is useful for controlling the metabolism of a plant, facilitating the growth of a beneficial plant such as cereals by inhibiting the growth of undesirable plants or eradicating them, regulating the growth of a plant and dwarfing a plant.
    Type: Grant
    Filed: October 31, 1984
    Date of Patent: February 20, 1990
    Assignee: Teijin Limited
    Inventors: Shizuo Azuma, Toshiyuki Hiramatsu, Teizo Yamaji, Yataro Ichikawa
  • Patent number: 4888050
    Abstract: Certain novel fluorophenoxy compounds, principally aryloxyfluorophenoxyalkanoic acids and derivatives thereof, are described. More specifically, these novel compounds bear 1 to 4 fluorine substituents on the phenyl ring. These novel compounds exhibit surprising preemergent and postermergent activity when used according to the method of the invention in the control of grassy weeds.
    Type: Grant
    Filed: February 11, 1988
    Date of Patent: December 19, 1989
    Assignee: The Dow Chemical Company
    Inventor: Richard B. Rogers
  • 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: 4871470
    Abstract: Cyclohexane derivatives of formula I ##STR1## wherein R is an alkyl group which has 1-12 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by O, --CO--O-- or --OCO--,A.sup.1 and A.sup.2 each independently of one another are trans-1,4-cyclohexylene or unsubstituted or fluorine-substituted 1,4-phenylene, and one of the groups A.sup.1 and A.sup.2 can also be a single bond,X is --CN, halogen, OH, --COOR.sup.1, --OOCR.sup.1, --COR.sup.1, --OR.sup.1 or R.sup.1 andR.sup.1 is an alkyl group which has 1-12 C atoms and in which one or two CH.sub.2 groups can also be replaced by O, but excluding direct links between two O atoms,with the proviso that, in the case of X=CN, A.sup.2 is trans-1,4-cyclohexylene or fluorine-substituted, 1,4-phenylene, are suitable as components of liquid-crystalline phases.
    Type: Grant
    Filed: October 30, 1987
    Date of Patent: October 3, 1989
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Andreas Wachtler, Joachim Krause, Rudolf Eidenschink, Georg Weber
  • Patent number: 4870104
    Abstract: 11-Haloprostane derivatives of general formula I ##STR1## wherein X is F, Cl or Br,R.sub.1 is the residue CH.sub.2 OH or ##STR2## wherein R.sub.2 means a hydrogen atom, an alkyl, cycloalkyl, aryl, phenacyl or heterocyclic residue,A is a --CH.sub.2 --CH.sub.2 -- or cis-CH.dbd.CH-group,B is a --CH.sub.2 --CH.sub.2 -- or trans-CH.dbd.CH-- or a --C.tbd.C-group,W is an ethylenedioxymethylene group or a hydroxymethylene group,D and E together mean a direct bond orD is a C.sub.1-10 -alkylene group,E is an oxygen or sulfur atom, a direct bond, a --C.tbd.C-bond or a --CR.sub.6 .dbd.CR.sub.7 -group with R.sub.6 and R.sub.7 meaning a hydrogen atom, a chlorine atom or an alkyl group,R.sub.4 is a hydroxy group,R.sub.5 is a hydrogen atom, an alkyl, a cycloalkyl, an aryl or a heterocyclic group, andthe salts thereof with physiologically compatible bases, processes for their preparation, and use thereof as agents inhibiting gastric acid secretion.
    Type: Grant
    Filed: November 12, 1986
    Date of Patent: September 26, 1989
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Claus-Steffen Sturzebecher, Walter Elger
  • Patent number: 4866198
    Abstract: Novel Calixarene derivatives useful as accelerators in cyanoacrylate adhesive compositions are represented by the formula ##STR1## wherein m+n=4,6 or 8n=an integer greater than or equal to 1/2 (m+n)R.sup.9 is aryl, hydrocarbylaryl, aryloxy, hydrocarbylaryloxy,substituted aryl, substituted hydrocarbylaryl, substituted aryloxy or substituted hydrocarbylaryloxy; or when R.sup.10 is aryl, hydrocarbylaryl,substituted aryl or substituted hydrocarbylaryl, R.sup.9 is hydrocarbyl,hydrocarbyloxy, substituted hydrocarbyl or substituted hydrocarbyloxy;R.sup.10 is H, hydrocarbyl, aryl, hydrocarbylaryl, substituted hydrocarbyl, substituted aryl or substituted hydrocarbylaryl;R.sup.11 is H, hydrocarbyl or substituted hydrocarbyl;provided that neither R.sup.9 or R.sup.11 is substituted with a basic N-containing group.
    Type: Grant
    Filed: August 24, 1987
    Date of Patent: September 12, 1989
    Assignee: Loctite Corporation
    Inventor: Stephen J. Harris
  • Patent number: 4845264
    Abstract: A novel phenoxycarboxylic acid of formula (I) is disclosed. The compound is effective as herbicide for eradicating broad-leaved weeds. A combination of the phenoxycarboxylic acid and a N-phosphonomethylglycine or a glufosinate which is known as a herbicide is very effective for eradicating both broad-leaved weeds and narrow-leaved weeds.
    Type: Grant
    Filed: March 1, 1988
    Date of Patent: July 4, 1989
    Assignee: Teijin Limited
    Inventors: Shizuo Azuma, Toshiyuki Hiramatsu, Koji Nakagawa, Yataro Ichikawa
  • Patent number: 4808750
    Abstract: Novel fluorophenoxyphenoxypropionates and derivatives thereof possess herbicidal activity selectively in the presence of broadleaf crops. Preemergent and postemergent applications are contemplated.
    Type: Grant
    Filed: July 14, 1986
    Date of Patent: February 28, 1989
    Assignee: The Dow Chemical Company
    Inventors: Richard B. Rogers, B. Clifford Gerwick, III
  • Patent number: 4804777
    Abstract: Process for the preparation of an aryloxyacetic acid by oxidation of aryloxyethanol of the formula: ##STR1## wherein m represents 1 or 2,n represents the numeral which results from the difference between 6 and m and R either individually or independently of one another represents hydrogen, alkyl, cycloalky, aryl, aralkyl, alkoxy, cycloalkoxy, aryloxy, halogen, alkylcarbonyl, arylcarbonyl, carboxyl or nitro, or represents a benzene ring fused to the phenyl ring, in an aqueous alkaline reaction medium at a temperature in the range of 0.degree. C. to the boiling point of the reaction medium in the presence of a catalytic amount of a catalyst comprised of palladium, silver and optionally antimony, and carbon to form the corresponding alkali metal ester and contacting the alkali metal with a mineral acid.
    Type: Grant
    Filed: October 9, 1987
    Date of Patent: February 14, 1989
    Assignee: Eastman Kodak Company
    Inventors: Charles E. Sumner, Jr., Eric J. Fugate
  • Patent number: 4789685
    Abstract: 9-fluoroprostane derivatives of Formula I ##STR1## wherein R.sub.1 is CH.sub.2 OH or ##STR2## wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is the residue ##STR3## wherein R.sub.3 is an acid residue or R.sub.2 and A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--,B is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH-- or --C.tbd.C,W is a free or functionally modified hydroxymethylene group wherein the OH-group can be in the .alpha.- or .beta.- position,D and E jointly are a direct bond orD is straight-chain or branched alkylene or alkenylene of 1-10 carbon atoms which can optionally be substituted by fluorine atoms, and E is oxygen or sulfur, a direct bond, --C.tbd.C-- or --CR.sub.6 .dbd.CR.sub.7 -- wherein R.sub.6 and R.sub.7 differ from each other and each is hydrogen, chlorine, or alkyl,R.sub.4 is a free or functionally modified hydroxy group, andR.sub.5 is hydrogen, an optionally substituted aliphatic group, e.g.
    Type: Grant
    Filed: January 20, 1987
    Date of Patent: December 6, 1988
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Michael-Harold Town
  • Patent number: 4789744
    Abstract: A process for the effective analytical or preparative resolution of the enantiomers of 2-(4-aryloxyphenoxy)propionic acids or the C.sub.1 -C.sub.4 alkyl esters thereof which comprises converting a racemic or partially resolved mixture of said 2-(4-aryloxyphenoxy)propionic acids or the C.sub.1 -C.sub.4 alkyl esters thereof to a pair of diastereomeric terpene esters by reaction with an optically active terpene alcohol and separating the diastereomers of the terpene ester by liquid chromatography with a silica column.
    Type: Grant
    Filed: August 5, 1987
    Date of Patent: December 6, 1988
    Assignee: The Dow Chemical Company
    Inventor: John W. Russell
  • Patent number: 4786731
    Abstract: A method for the chromatographic resolution and analysis of the enantiomers of 2-(phenyl or phenoxy)propionic acids or the C.sub.1 -C.sub.4 alkyl esters thereof which comprises converting a racemic or partially resolved mixture of said 2-(phenyl or phenoxy)propionic acids or the C.sub.1 -C.sub.4 alkyl esters thereof to a pair of diastereomeric 2-amino-1-alkanol derivatives by reaction with an optically active 2-amino-1-alkanol, and analyzing the diastereomeric mixture by gas chromatography.
    Type: Grant
    Filed: August 5, 1987
    Date of Patent: November 22, 1988
    Assignee: The Dow Chemical Company
    Inventor: John W. Russell
  • Patent number: 4786732
    Abstract: A method for the effective chromatographic resolution and analysis of the enantiomers of 2-(4-aryloxyphenoxy)propionic acids which comprises dissolving a 2-(4-aryloxyphenoxy)propionic acid in a suitable solvent, injecting the solution into a liquid chromatographic system and eluting the components from the column using an eluent contain R-(-)- or S-(+)-2-pyrrolidinemethanol and an alkanoic acid in a suitable solvent.
    Type: Grant
    Filed: August 5, 1987
    Date of Patent: November 22, 1988
    Assignee: The Dow Chemical Company
    Inventor: John W. Russell
  • Patent number: 4766220
    Abstract: The invention relates to the preparation of optically active aryloxyalkanoic acid derivatives of the formula ##STR1## in which Ar represents an optionally substituted phenyl, naphthyl, phenoxy or pyridyloxy radical, R represents a C.sub.1 -C.sub.4 -alkyl radical and A represents a --COOR.sub.1, ##STR2## or --CO--Z radical, Z being halogen. It consists in reacting an aqueous or aqueous-organic solution of an optically active alkali metal salt of a 2-halogeno-alkanoic acid with an aqueous solution of an alkali metal salt of the phenol of the formula Ar-OH at an elevated temperature under a pressure less than the vapor pressure of water at the chosen temperature.It permits the preparation of aryloxyalkanoic acid derivatives with a very high content of the isomer having the D configuration, which can be used as herbicides.
    Type: Grant
    Filed: July 30, 1985
    Date of Patent: August 23, 1988
    Assignee: Rhone-Poulenc Agrochimie
    Inventor: Georges Gras
  • Patent number: 4757155
    Abstract: A process for the preparation of optically active 2-[4-(2',4'-dihalophenoxy)phenoxy]propionic acids of at least 75 percent enantiomeric excess of the desired optical isomer which comprises contacting a 2-chloropropionic acid or a lower alkyl ester or an alkali metal salt thereof, having an optical purity of greater than 90 percent of the opposite configuration, with from 2 to 10 molar equivalents of a 4-(2',4'-dihalphenoxy)phenol in an aqueous base.
    Type: Grant
    Filed: December 22, 1986
    Date of Patent: July 12, 1988
    Assignee: The Dow Chemical Company
    Inventor: Jimmy J. Tai
  • Patent number: 4750931
    Abstract: Certain novel fluorophenoxy compounds, principally aryloxyfluorophenoxyalkanoic acids and derivatives thereof, are described. More specifically, these novel compounds bear 1 to 4 fluorine substituents on the phenyl ring. These novel compounds exhibit surprising preemergent and postemergent activity when used according to the method of the invention in the control of grassy weeds.
    Type: Grant
    Filed: October 15, 1985
    Date of Patent: June 14, 1988
    Assignee: The Dow Chemical Company
    Inventor: Richard B. Rogers
  • Patent number: 4744918
    Abstract: Liquid crystal phases containing at least one optically active compound of the formula IR.sup.1 --X.sup.1 --CHR.sup.o (CH.sub.2).sub.p X.sup.2 --R.sup.2 Iwherein X.sup.1 and X.sup.2 independently of one another are each --CO--O-- or --O--CO--, one of X.sup.1 and X.sup.2 may also be --O--, R.sup.1 and R.sup.2 independently of one another are each a group --(A.sup.1 --Z).sub.m --(A.sup.2).sub.n -Y, whereinA.sup.1 and A.sup.2 in each case independently of one another are a 1,4-phenylene, pyrimidine-2,5-diyl, pyrazine-2,5-diyl, pyridine-2,5-diyl, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,3-dithiane-2,5-diyl or 1,4-bicyclo(2,2,2)-octylene group, it also being possible for this to be monosubstituted or polysubstituted by F, Cl, Br, CN and/or alkyl groups with up to 12 C atoms, and it being possible for 1 or 2 non-adjacent CH.sub.2 groups in the alkyl groups to be replaced by O atoms,Z is --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, --CH.dbd.N--, --N.dbd.CH--, --N.dbd.N--, --N(O).
    Type: Grant
    Filed: July 11, 1985
    Date of Patent: May 17, 1988
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Gerd Heppke, Feodor Oestreicher
  • Patent number: 4739101
    Abstract: The present invention relates to a method for the preparation of fibrates of the formula I according to the mechanism: ##STR1## in which R.sub.1 represents especially a halogen atom (in particular F, Cl or Br, the preferred halogen atom being Cl) or an acetyl, (4-chlorophenyl)hydroxymethyl, 4-chlorobenzoyl or 2-(4-chlorobenzamido)ethyl group and R.sub.2 represents a C.sub.1 -C.sub.4 alkyl group in which the hydrocarbon chain is linear or branched, the reaction V+VI being carried out without a solvent.
    Type: Grant
    Filed: April 27, 1987
    Date of Patent: April 19, 1988
    Assignee: Fournier Innovation et Synergie
    Inventors: Jean-Pierre Bourgogne, Roland Sornay
  • Patent number: 4731466
    Abstract: The invention concerns compounds having the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 can mean identical or different radicals in any desired position on the benzene ring, namely fluoro, chloro, bromo, iodo, cyano, or nitro radicals, alkyl radicals having from 1 to 4 carbon atoms, cyclo alkyl radicals having from 3 to 7 carbon atoms, phenyl, phenylsulfonyl and phenoxy radicals and hydrogen;n can mean a number with the value of 1 or 2 andx can mean CH.sub.2, and where n=1, O--CH.sub.2 as well.The named componds show efficiency as fungicides.
    Type: Grant
    Filed: April 30, 1987
    Date of Patent: March 15, 1988
    Assignee: The Dow Chemical Company
    Inventors: Gerhard Staiger, Peter Kinzel
  • Patent number: 4725683
    Abstract: Novel intermediates useful in the preparation of fluorophenoxyphenoxypropionates and derivatives thereof which possess herbicidal activity selectively in the presence of broadleaf crops.
    Type: Grant
    Filed: August 12, 1985
    Date of Patent: February 16, 1988
    Assignee: The Dow Chemical Company
    Inventors: Richard B. Rogers, B. Clifford Gerwick, III
  • Patent number: 4717417
    Abstract: New dextrorotatory enantiomers of phenoxy propionic acid derivatives of the formula ##STR1## in which R.sup.1 represents a radical of the formula ##STR2## wherein X.sup.1 represents hydrogen or halogen,X.sup.2 represents halogen or trifluoromethyl,X.sup.3 represents halogen or trifluoromethyl,X.sup.4 represents hydrogen or halogen andX.sup.5 represents hydrogen or halogen,Y represents oxygen or the radical SO.sub.m,whereinm represents 0, 1 or 2,R.sup.2 represents hydrogen or methyl,n represents 1 or 2 andR.sup.3 and R.sup.4 independently of one another represent hydrogen, halogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, nitro, cyano or alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy group, and their use as herbicides.
    Type: Grant
    Filed: March 14, 1986
    Date of Patent: January 5, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Koichi Moriya, Uwe Priesnitz, Hans-Jochem Riebel, Ludwig Eue, Robert R. Schmidt