Halogen Attached Indirectly To The Six-membered Hetero Ring By Nonionic Bonding Patents (Class 546/346)
  • Patent number: 6770463
    Abstract: There is provided a process for the preparation of a chiral insecticidal and acaricidal compound of formula I. Also provided are intermediate compounds useful in the process of the present invention.
    Type: Grant
    Filed: August 2, 2001
    Date of Patent: August 3, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: John Francis Chiarello, Brian Lee Buckwalter, Timothy Claude Barden
  • Publication number: 20040092728
    Abstract: The present invention provides a process for producing aromatic bromide or aromatic iodide from an aromatic amine derivative using nitrite ion and holodimethylsulfonium halide generated in situ from hydrobromic acid/DMSO or hydriodic acid/DMSO. The process for producing compounds of the formula (1) is disclosed (1) wherein X is bromine or iodine: Y is carbon C or nitrogen; R1, R?2?, R3, R4 which may be the same or different and are selected independently from the group consisting of a hydrogen, a hologen, a C1-C8 alkyl, a C1-C10 alkoxy, a nitro, a formyl, an aryl, a benzyl, a C2-C10 alkylcarbonyl and an arylcarbonyl, provided that adjacent groups as selected from among R1, R2, R3, R4 and R1 may combine to form a ring.
    Type: Application
    Filed: November 25, 2002
    Publication date: May 13, 2004
    Inventors: Woon Phil Baik, Jung Min Kim, Young Sam Kim, Cheol Hun Yoon, Shin Jong Kim, Seok Woo Lee
  • Patent number: 6699853
    Abstract: The present invention relates to 4-Haloalkyl-3-heterocyclylpyridines, 4-haloalkyl-5-heterocyclyl-pyrimidines and 4-trifluoromethyl-3-oxadiazolylpyridines, Processes for Their Preparation, Compositions Comprising Them, and Their Use as Pesticides More particularly, the present invention relates to 4-trifluoromethyl-3-oxadiazolylpyridines of the formula (I′), to processes for their preparation, to compositions comprising them and to the use of these compounds for controlling animal pests, in particular insects, spider mites, ectoparasites and helminths: wherein X, Y are as defined in the description.
    Type: Grant
    Filed: January 24, 2002
    Date of Patent: March 2, 2004
    Assignee: Hoechst Schering AgrEvo GmbH
    Inventors: Sven Harmsen, Henricus Maria Martinus Bastiaans, Wolfgang Schaper, Jörg Tiebes, Uwe Döller, Daniela Jans, Ulrich Sanft, Waltraud Hempel, Maria-Theresia Thönessen, Thomas Taapken, Burkhard Rook, Manfred Kern
  • Patent number: 6667401
    Abstract: The present invention relates to a process for the preparation of compounds of the formula (I) in which R1, A, D, X and Z have the meanings given in the description, by reacting compounds of the formula (II)  in which A, D and X have the meanings given above, with a base and in the presence of a diluent, and subsequently reacting the reaction mixture with the mixture of CCMP/CMP (2-chloro-5-chloromethylpyridine/2-chloro-5-methylpyridine) and the corresponding hydrochlorides.
    Type: Grant
    Filed: March 26, 2002
    Date of Patent: December 23, 2003
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hermann Seifert, Uwe Stelzer
  • Publication number: 20030225116
    Abstract: Substituted 4-phenyl-1-(1-phenylcyclohexyl)-1,2,3,6-tetrahydropyridine (compounds), methods for the production thereof, pharmaceutical compositions containing said compounds, and methods of treatment of pain and other diseases using the pharmaceutical compositions.
    Type: Application
    Filed: March 7, 2003
    Publication date: December 4, 2003
    Applicant: Gruenental GmbH
    Inventors: Boris Chizh, Michael Sattlegger, Claudia Hinze, Bernd Sundermann, Angelika Kerwer-Thomas, Gisela Henn
  • Patent number: 6656957
    Abstract: A compound of formula I wherein X represents an optionally halo-substituted (C2-4)alkynylene group bonded via vicinal unsaturated carbon atoms.
    Type: Grant
    Filed: November 27, 2000
    Date of Patent: December 2, 2003
    Assignees: Novartis AG, Sibia Neurosciences Inc.
    Inventors: Hans Allgeier, Yves Auberson, Michel Biollaz, Nicholas David Cosford, Fabrizio Gasparini, Roland Heckendorn, Edwin Carl Johnson, Rainer Kuhn, Mark Andrew Varney, Gönül Veliçelebi
  • Publication number: 20030149272
    Abstract: The invention concerns a method for preparing a polyaromatic compound comprising at least a chain formation of two aromatic cycles. The method for preparing a polycyclic aromatic compound comprising at least a chain formation of two aromatic cycles is characterised in that it consists in reacting an aromatic compound bearing a leaving group and an alkaline organometallic compound, in the presence of an efficient amount of a nickel catalyst, said element being optionally complexed with at least a co-ordination agent or ligand.
    Type: Application
    Filed: November 4, 2002
    Publication date: August 7, 2003
    Inventors: Henri-Jean Cristau, Corinne Bouchitte, Marc Taillefer, Jean-Francis Spindler, Thierry Schlama
  • Patent number: 6491989
    Abstract: Fluorinated naphthalene derivatives of the formula (I) R1(—A1—M1)a(—A2—M2)b—B—(—M3—A3)c—(M4—A4)d—R2  (I) where B is  having the meaning  and R1(—A1—M1)a(—A2—M2) and (—M3—A3)(M4—A4)R2 are mesogenic radicals, are suitable as components of liquid-crystal mixtures, in particular ferroelectric liquid-crystal mixtures.
    Type: Grant
    Filed: July 10, 2000
    Date of Patent: December 10, 2002
    Assignee: Aventis Reseach & Technologies GmbH & Co. KG
    Inventors: Javier Manero, Wolfgang Schmidt, Barbara Hornung
  • Patent number: 6489334
    Abstract: The invention relates to a method of crystallizing a tetrahydropyridine derivative, to the novel crystalline forms thereby obtained and to the pharmaceutical compositions containing said tetrahydropyridine derivative in a given crystalline form as the active principle.
    Type: Grant
    Filed: September 6, 2001
    Date of Patent: December 3, 2002
    Assignee: Sanofi-Synthelabo
    Inventors: Antoine Caron, Bruno Franc, Olivier Monnier
  • Patent number: 6485797
    Abstract: A ferroelectric liquid crystal mixture, especially useful for operation in the &tgr;Vmin−mode, comprises a 5-Arylindane derivative of the formula (I), wherein Y is CH, CF or N and R1(—A1—M1)a(—A2—M2)b—, (M3—A3—)cR2 are mesogenic groups.
    Type: Grant
    Filed: August 31, 2000
    Date of Patent: November 26, 2002
    Assignee: Aventis Research & Technologies GmbH & Co. KG
    Inventors: Wolfgang Schmidt, Javier Manero, Barbara Hornung, Rainer Wingen, Ayako Ogawa
  • Patent number: 6417361
    Abstract: The invention disclose a hydrogen fluoride containing composition comprising hydrogen fluoride and a compound which is liquid in the standard state (25° C., 1 atmosphere) and has a boiling point of 120° C. or more and pka of 12 or more at 25° C., and use of the composition for a fluorination agent. The compound which can be preferably used is represented by the formula (1): wherein R1 to R4 are a substituted or unsubstituted alkyl or aryl group and can be the same or different, and R1 or R2 or R3 and R4 can bond to form a ring having a nitrogen atom or a nitrogen atom and other hetero atom, or R1 and R3 can bond to form a ring having a nitrogen atom or a nitrogen atom and other hetero atom.
    Type: Grant
    Filed: October 13, 2000
    Date of Patent: July 9, 2002
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Hidetoshi Hayashi, Hiroshi Sonoda, Ken'ichi Goto, Kouki Fukumura, Junko Naruse, Hideaki Oikawa, Teruyuki Nagata, Takashi Shimaoka, Tsuyoshi Yasutake, Hideki Umetani, Toshio Kitashima
  • Patent number: 6392050
    Abstract: The invention relates to a process for preparing substituted pyridines in a simple and cost-effective manner in good yields by reacting substituted 1,4-dihydropyridines with methyl nitrite in the presence of an acid that contains less than 20% by weight of oxidizing components.
    Type: Grant
    Filed: June 4, 2001
    Date of Patent: May 21, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Norbert Lui, Hans Panskus, Albert Schnatterer
  • Publication number: 20020032351
    Abstract: There is provided a process for the preparation of a chiral insecticidal and acaricidal compound of formula I.
    Type: Application
    Filed: August 2, 2001
    Publication date: March 14, 2002
    Applicant: BASF Aktiengesellschaft
    Inventors: John Francis Chiarello, Brian Lee Buckwalter, Timothy Claude Barden
  • Publication number: 20020026057
    Abstract: The invention relates to a method of crystallizing a tetrahydropyridine derivative, to the novel crystalline forms thereby obtained and to the pharmaceutical compositions containing said tetrahydropyridine derivative in a given crystalline form as the active principle.
    Type: Application
    Filed: September 6, 2001
    Publication date: February 28, 2002
    Inventors: Antoine Caron, Bruno Franc, Olivier Monnier
  • Patent number: 6309561
    Abstract: Fluorine-containing, chiral liquid crystal compounds comprise (a) a chiral fluorochemical terminal portion comprising (i) at least one chiral center, which can optionally be heteroatom-substituted; (ii) a terminal fluoroalkyl, fluoroether, perfluoroalkyl, or perfluoroether group; and (iii) an alkylene or fluoroalkylene group optionally containing at least one catenary ether oxygen atom; (b) a chiral or achiral terminal portion consisting of a hydrocarbon or hydrocarbon ether group, and, when chiral, comprising at least one chiral center, which can optionally be heteroatom-substituted; and (c) a central core connecting the terminal portions; the alkylene or fluoroalkylene group of the chiral fluorochemical terminal portion having at least 3 in-chain atoms and being located between the chiral center of the chiral fluorochemical terminal portion and the central core. The compounds have smectic mesophases or latent smectic mesophases and are useful, for example, in liquid crystal display devices.
    Type: Grant
    Filed: December 24, 1997
    Date of Patent: October 30, 2001
    Assignee: 3M Innovative Properties Company
    Inventors: Masakazu Hasegawa, Michael P. Keyes, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
  • Patent number: 6268503
    Abstract: A series of compounds capable of deriving an intermediate for the production of compound (A) of the following formula, which is an anti-HIV drug, and a production method thereof. To be specific, 4-(pyridin-2-yl)benzaldehyde hydrazone, a production method of this compound, and a production method from this compound to N-(tert-butoxycarbonyl)-N′-[4-(pyridin-2-yl)phenylmethylidene]hydrazine. In addition, a salt of 2-(4-bromomethylphenyl)pyridine, 2-(4-dibromomethylphenyl)pyridine and a salt thereof, production methods of these compounds, and production methods to derive 4-(pyridin-2-yl)benzaldehyde which is a production intermediate for 4-(pyridin-2-yl)benzaldehyde hydrazone from these compounds.
    Type: Grant
    Filed: July 7, 2000
    Date of Patent: July 31, 2001
    Assignee: Sumika Fine Chemicals Co., Ltd.
    Inventors: Kozo Matsui, Kiyoshi Sugi, Yoshihide Umemoto, Tetsuya Shintaku, Nobushige Itaya
  • Patent number: 6184425
    Abstract: The present invention relates to a process for preparing fluorine-containing compounds by reacting a compound which contains fluorine-exchangeable halogen with a fluoride or a mixture of fluorides with the formula I MeF  (I), in which Me is an alkaline earth metal ion, NH4+-ion or alkali metal ion, in the presence of a compound or a mixture of compounds of the formula (II) in which A1, A2, A3, A4, A5, A6, A7, A8 independently of one another are identical or different and are a straight-chain or branched alkyl or alkenyl having 1 to 12 carbon atoms, cycloalkyl having 4 to 8 carbon atoms, an aryl having 6 to 12 carbon atoms, or an aralkyl having 7 to 12 carbon atoms, or A1 A2, A3A4, A5A6, and A7A8 independently of one another are identical or different and are connected to one another directly or by way of O or N—A9 to form a ring having 3 to 7 ring members, A9 is an alkyl having 1 to 4 carbon atoms and B− is a monovalent acid radical or the equivalent of a polyval
    Type: Grant
    Filed: July 7, 1999
    Date of Patent: February 6, 2001
    Assignee: Aventis Research & Technologies GmbH & Co.
    Inventors: Alexander Kolomeitsev, Sergej Pasenok
  • Patent number: 6184384
    Abstract: Described are preferred processes for preparing 3,5-dichloropyridines by dechlorinating higher-chlorinated pyridine compounds such as 2,3,5,6-tetrachloropyridine in an acidic medium in the presence of zinc and optionally a quaternary ammonium catalyst.
    Type: Grant
    Filed: July 15, 1999
    Date of Patent: February 6, 2001
    Assignee: Reilly Industries, Inc.
    Inventors: Phillip B. Lawin, Z. Jason Yang, L. Mark Huckstep
  • Patent number: 6162810
    Abstract: A new family of inadone and tetralone tubulin-binding compounds (TBs) is disclosed. Unlike classical TBs, which inhibit mitosis among affected dividing cells, the TBs of the invention possess two unique properties: (1) they induce apoptosis among stationary phase (non-dividing) malignant cells, yet do not impair the viability of normal nonproliferating cells; and, (2) they affect cells which have acquired MDR more powerfully than they affect cells without MDR. Thus, the TBs of the invention provide means to target malignant cells for chemotherapy, even after previous therapies have failed, without affecting normal cells and tissues in the host.
    Type: Grant
    Filed: September 4, 1998
    Date of Patent: December 19, 2000
    Assignee: The Regents of the University of California
    Inventors: Dennis A. Carson, Hsien C. Shih, Howard B. Cottam, Lorenzo Leoni
  • Patent number: 6147082
    Abstract: The invention relates to a novel class of compounds that have structures related to certain naturally occurring or synthetic chalcones. The invention also relates to pharmaceutical compositions comprising the compounds and methods for treating certain disorders using the pharmaceutical compositions. The invention further relates to process for synthesizing the novel class of compounds.
    Type: Grant
    Filed: December 8, 1999
    Date of Patent: November 14, 2000
    Inventors: Ezio Bombardelli, Piero Valenti
  • Patent number: 6118006
    Abstract: The invention relates to a method for the preparation of 1-[2-(2-naphthyl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyri dine and its pharmaceutically acceptable salts by reacting 2-(2-bromoethyl)naphthalene with 4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine or one of its salts, and to a universal method for the preparation of the same product and its salts by the reduction of naphthylacetic acid, treatment of the resulting 2-naphthylethanol with hydrobromic acid and treatment of the 2-(2-bromoethyl)naphthalene with 4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine or one of its salts.
    Type: Grant
    Filed: June 22, 1999
    Date of Patent: September 12, 2000
    Assignee: Sanofi-Synthelabo
    Inventors: Michel Buj, Robert Filhol
  • Patent number: 6066766
    Abstract: 4-Chlorobiphenyls are prepared by reacting a haloaromatic with an aryl Grignard compound, where halogen is chlorine, bromine or iodine, in the presence of a palladium catalyst of the formula (IV) ##STR1##
    Type: Grant
    Filed: August 3, 1999
    Date of Patent: May 23, 2000
    Assignee: Clariant GmbH
    Inventors: Steffen Haber, Stefan Scherer, Andreas Meudt, Antje Noerenberg
  • Patent number: 6051288
    Abstract: An object of the present invention is to provide a novel liquid crystalline compound having a large dielectric anisotropy, small change in threshold voltage depending on temperature, and an improved solubility to other liquid crystal materials at low temperatures, and expressed by the following general formula (1): ##STR1## wherein R represents, for example, an alkyl group or alkoxy group having 1 to 10 carbon atoms, m and n are independently 0 or 1, A.sub.1, A.sub.2, and A.sub.3 are independently, for example, trans-1,4-cyclohexylene group, 1,4-phenylene group one or more hydrogen atoms on the ring of which may be replaced by F, Z.sub.1, Z.sub.2, and Z.sub.3 independently represent --COO--, --OCO--, --(CH.sub.2).sub.2 --, --CH.sub.2 O--, --OCH.sub.2 --, or a covalent bond provided that at least one of Z.sub.1, Z.sub.2, and Z.sub.3 represents ester bond, --CH.sub.2 O--, or --OCH.sub.2 --, X represents, for example, CF.sub.3, CF.sub.2 H, and Y represents H or F.
    Type: Grant
    Filed: September 26, 1997
    Date of Patent: April 18, 2000
    Assignee: Chisso Corporation
    Inventors: Tomoyuki Kondo, Yasuhiro Haseba, Yasuyuki Koizumi, Kazutoshi Miyazawa, Norihisa Hachiya, Etsuo Nakagawa
  • Patent number: 6034090
    Abstract: The invention relates to compounds of the formula in which: Y is --CH-- or --N--; R.sub.1 is hydrogen, a halogen or a CF.sub.3, (C.sub.1 -C.sub.4)alkyl or (C.sub.1 -C.sub.4)alkoxy group; R.sub.2 is a methyl or ethyl group; R.sub.3 and R.sub.4 are each hydrogen or a (C.sub.1 -C.sub.3)alkyl; and X is:(a) a (C.sub.1 -C.sub.6)alkyl, a (C.sub.1 -C.sub.6)alkoxy, a (C.sub.3 -C.sub.7)carboxyalkyl, a (C.sub.1 -C.sub.4)alkoxy-carbonyl(C.sub.1 -C.sub.6)alkyl, a (C.sub.3 -C.sub.7)carboxyalkoxy or a (C.sub.1 -C.sub.4)alkoxycarbonyl-(C.sub.1 -C.sub.6)alkoxy;(b) a radical selected from (C.sub.3 -C.sub.7)cycloalkyl, (C.sub.3 -C.sub.7)cycloalkoxy, (C.sub.3 -C.sub.7)-cycloalkylmethyl, (C.sub.3 -C.sub.7)cycloalkylamino and cyclohexenyl, it being possible for said radical to be substituted by a halogen, hydroxyl, (C.sub.1 -C.sub.4)-alkoxy, carboxyl, (C.sub.1 -C.sub.4)alkoxycarbonyl, amino or mono- or di-(C.sub.1 -C.sub.4)-alkylamino; or(c) a group selected from a phenyl, phenoxy, phenylamino, N-(C.sub.1 -C.sub.
    Type: Grant
    Filed: July 27, 1999
    Date of Patent: March 7, 2000
    Assignee: Sanofi-Synthlabo
    Inventors: Marco Baroni, Rosanna Cardamone, Jacqueline Fournier, Umberto Guzzi
  • Patent number: 6030547
    Abstract: Fluorine-containing, chiral liquid crystal compounds comprise (a) a chiral fluorochemical terminal portion comprising (i) at least one chiral center, which can optionally be heteroatom-substituted; (ii) a terminal fluoroalkyl, fluoroether, perfluoroalkyl, or perfluoroether group; and (iii) an alkylene or fluoroalkylene group optionally containing at least one caternary ether oxygen atom; (b) a chiral or achiral terminal portion consisting of a hydrocarbon or hydrocarbon ether group, and, when chiral, comprising at least one chiral center, which can optionally be heteroatom-substituted; and (c) a central core connecting the terminal portions; the alkylene or fluoroalkylene group of the chiral fluorochemical terminal portion having at least 3 in-chain atoms and being located between the chiral center of the chiral fluorochemical terminal portion and the central core. The compounds have smectic mesophases or latent smectic mesophases and are useful, for example, in liquid crystal display devices.
    Type: Grant
    Filed: December 24, 1997
    Date of Patent: February 29, 2000
    Assignee: 3M Innovative Properties Company
    Inventors: Masakazu Hasegawa, Michael P. Keyes, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
  • Patent number: 6022492
    Abstract: Difluorophenylpyrimidylpyridine derivatives of the formula (I) ##STR1## wherein X is N and Y is CH or X is CH and Y is N;R.sup.1 and R.sup.2 are identical or different and area) an unbranched or branched alkyl chain having 1 to 20 carbon atoms, whereaa) one or more non-adjacent and non-terminal CH.sub.2 groups may be replaced by --O--, --CO--O--, --O--CO--, --O--CO--O-- or --Si(CH.sub.3).sub.2 --, and/orab) one or more H atoms may be replaced by F, and/orac) the terminal CH.sub.3 group may be replaced by one of the following chiral groups (optically active or racemic): ##STR2## R.sup.3, R.sup.4 and R.sup.5 are identical or different and are hydrogen or a straight-chain or branched alkyl radical having 1-16 carbon atoms (with or without an asymmetrical carbon atom), where, in addition, one or more non-adjacent non-terminal CH.sub.2 groups may be replaced by --O--, and/or where one or more H atoms of the alkyl radical may be substituted by --F; R.sup.4 and R.sup.5 may alternatively together be --(CH.sub.2).sub.
    Type: Grant
    Filed: January 14, 1999
    Date of Patent: February 8, 2000
    Assignee: Hoescht Research & Technology Deutchland GmbH & Co.
    Inventors: Toshiaki Nonaka, Ji Li, Ayako Takeichi, Barbara Hornung, Javier Manero, Wolfgang Schmidt, Rainer Wingen
  • Patent number: 6010980
    Abstract: Substituted 2-phenylpyridines I and their salts ##STR1## where n=0, 1;R.sup.1 =halogen, C.sub.1 -C.sub.4 -haloalkyl;R.sup.2 and R.sup.3 =H, halogen;R.sup.4 =CN, halogen;R.sup.5 =--CO--O-(C.sub.1 -C.sub.4 -alkylene)-CO--OR.sup.6, --CO--O-(C.sub.1 -C.sub.4 -alkylene)-CO--N(R.sup.7)R.sup.8, --O-(C.sub.1 -C.sub.4 -alkylene)-CO--O-(C.sub.1 -C.sub.4 -alkylene)-CO--OR.sup.6, --O-(C.sub.1 -C.sub.4 -alkylene)-CO--O-(C.sub.1 -C.sub.4 -alkylene)-CO--N(R.sup.7) R.sup.8, --S-(C.sub.1 -C.sub.4 -alkylene)-CO--O-(C.sub.1 -C.sub.4 -alkylene)-CO--OR.sup.6 or --S-(C.sub.1 -C.sub.4 -alkylene)-CO--O-(C.sub.1 -C.sub.4 -alkylene)-CO--N(R.sup.7)R.sup.8 ;R.sup.6 =H, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.3 -C.sub.4 -alkynyl;R.sup.7 =H, C.sub.1 -C.sub.4 -alkyl, carboxy-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxycarbonyl-C.sub.1 -C.sub.4 -alkyl;R.sup.8 =H or C.sub.1 -C.sub.4 -alkyl,are used as herbicides and for the desiccation/defoliation of plants.
    Type: Grant
    Filed: March 13, 1998
    Date of Patent: January 4, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Schafer, Gerhard Hamprecht, Elisabeth Heistracher, Olaf Menke, Cyrill Zagar, Michael Rack, Norbert Gotz, Albrecht Harreus, Karl-Otto Westphalen, Helmut Walter, Ulf Misslitz
  • Patent number: 5990314
    Abstract: This invention relates to a compound of formula I ##STR1## These compounds are leukotriene antagonists and as such can be used in treating various diseases associated with leukotrienes.
    Type: Grant
    Filed: June 7, 1996
    Date of Patent: November 23, 1999
    Assignee: SmithKline Beecham Corporation
    Inventor: Robert A. Daines
  • Patent number: 5972241
    Abstract: Fluorine-containing, chiral liquid crystal compounds comprise (a) a chiral fluorochemical terminal portion containing at least one methylene group and optionally containing at least one catenary ether oxygen atom; (b) a saturated, chiral or achiral, hydrocarbon terminal portion; and (c) a central core connecting the terminal portions. The compounds have smectic mesophases or latent smectic mesophases and are useful, for example, in liquid crystal display devices.
    Type: Grant
    Filed: November 6, 1997
    Date of Patent: October 26, 1999
    Assignee: 3M Innovative Properties Company
    Inventors: Gilbert C. Johnson, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
  • Patent number: 5961958
    Abstract: The present invention discloses compositions containing a transfer agent and/or bactericidal compounds, and hydrophobic materials which form, upon application to dental surfaces, adhesive, protective and bacteria-inhibiting barriers.
    Type: Grant
    Filed: July 16, 1996
    Date of Patent: October 5, 1999
    Assignee: Four Star Partners
    Inventors: Andrew M. Homola, Ronald K. Dunton
  • Patent number: 5942625
    Abstract: Chloromethylpyridine hydrochlorides such as 3-chloromethylpyridine hydrochloride, an important pharmaceutical intermediate, are prepared in high yield and high purity by reacting the corresponding pyridyl carbinol with a slight excess of thionyl chloride, in solution in an inert solvent such as toluene. The pyridyl carbinol solution is added to the thionyl chloride gradually and under its surface, to prevent the formation of impurities. The product is recovered by applying vacuum or nitrogen purge to the reaction mixture to assist precipitation, followed by filtration and washing.
    Type: Grant
    Filed: November 6, 1998
    Date of Patent: August 24, 1999
    Assignee: Delmar Chemicals
    Inventors: Yuan Wang, Lu Wei Liu, Alexandre L'Heureux, Olivier Lepage, Diane Phelan
  • Patent number: 5925645
    Abstract: The 2-aryl-substituted pyridines are prepared by reacting pyridylaldehydes with organometallic compounds and then selectively reducing the products. The 2-aryl-substituted pyridines are suitable as active compounds in medicaments, in particular in medicaments for the treatment of arteriosclerosis.
    Type: Grant
    Filed: March 13, 1997
    Date of Patent: July 20, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunter Schmidt, Rolf Angerbauer, Arndt Brandes, Michael Logers, Matthias Muller-Gliemann, Hilmar Bischoff, Delf Schmidt, Stefan Wohlfeil
  • Patent number: 5922880
    Abstract: The dihalopropene compounds of the general formula ?I! have excellent insecticidal/acaricidal activity, so that they are satisfactorily effective for the control of noxious insects, mites and ticks.
    Type: Grant
    Filed: May 20, 1997
    Date of Patent: July 13, 1999
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noriyasu Sakamoto, Sanshiro Matsuo, Masaya Suzuki, Taro Hirose, Kazunori Tsushima, Kimitoshi Umeda
  • Patent number: 5886186
    Abstract: The subject invention features substituted N-heteroaromatic compounds, libraries of substituted N-heteroaromatic compounds, and methods of synthesis thereof. For example, the present invention provides methods for synthesizing substituted N-heteroaromatic compounds, and is particularly amenable to the generation of libraries of substituted N- heteroaromatic compounds by combinatorial chemistry. The methods of the invention generally feature the reaction of O-linked heteroaromatic N-oxides with nucleophiles to produce substituted N-heteroaromatic compounds.
    Type: Grant
    Filed: October 25, 1995
    Date of Patent: March 23, 1999
    Assignee: Versicor, Inc.
    Inventors: Robert L. Smith, Gnanasambandam Kumaravel, Donald E. Kuhla
  • Patent number: 5869506
    Abstract: The present invention provides a fluoropropene compound represented by Formula I: ##STR1## wherein R.sup.1 represents a C.sub.1 -C.sub.10 alkyl group or other groups, Z represents an oxygen atom or other groups, R.sup.2, R.sup.3, and R.sup.4 each independently represent a C.sub.1 -C.sub.3 alkyl group or other groups, r represents an integer of 0 to 2, and X represents a halogen atom or other groups.
    Type: Grant
    Filed: January 30, 1997
    Date of Patent: February 9, 1999
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Keiichi Izumi, Hiroshi Ikegami, Masaya Suzuki, Noriyasu Sakamoto, Hirotaka Takano
  • Patent number: 5861109
    Abstract: Liquid crystal compounds of formula I may be used by themselves or they may be mixed with other liquid crystal compounds to give useful liquid crystal mixtures which may then be used in liquid crystal devices. The materials exhibit smectic mesophases and may therefore be used in ferroelectric, ferrielectric, antiferroelectric, themochromic and electroclinic devices. They may also be used as long pitch materials.
    Type: Grant
    Filed: January 24, 1996
    Date of Patent: January 19, 1999
    Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland of Defence Evaluation Research Agency
    Inventors: John W. Goodby, Peter Styring, Christa Loubser, Philippus L Wessels
  • Patent number: 5856286
    Abstract: The invention provides a fluorinated surfactant for use with halocarbon and hydrofluoroether solvents. Additionally, the invention provides drying, dry cleaning, and soil repellency compositions containing a halocarbon or hydrofluoroether and a fluorinated surfactant.
    Type: Grant
    Filed: June 23, 1997
    Date of Patent: January 5, 1999
    Assignee: AlliedSignal Inc.
    Inventors: David Nalewajek, Leonard Michael Stachura, Gary John Zyhowski
  • Patent number: 5852189
    Abstract: Relatively pure tertiaryaminoalkyllithium initiators suitable for anionic polymerization reactions are prepared at low temperatures in an organic ether by reacting an equivalent excess of lithium metal with a tertiaryaminoalkylhalide. The lithium initiators are very stable at moderate temperatures when the ether is replaced by an aliphatic, a cycloaliphatic, or an aromatic solvent. Yields of the initiator in excess of 98% are readily achieved.
    Type: Grant
    Filed: December 31, 1996
    Date of Patent: December 22, 1998
    Assignee: Bridgestone Corporation
    Inventors: William L. Hergenrother, Michael L. Kerns, David F. Lawson
  • Patent number: 5756497
    Abstract: This invention relates to certain novel benzoxazinone compounds and derivatives thereof, their synthesis, and their use as oxytocin receptor antagonists. One application of these compounds is in the treatment of preterm labor in mammals, especially humans. The ability of the compounds to relax uterine contractions in mammals also makes them useful for treating dysmenorrhea and stopping labor prior to cesarean delivery.
    Type: Grant
    Filed: February 27, 1997
    Date of Patent: May 26, 1998
    Assignee: Merck & Co., Inc.
    Inventors: Ian M. Bell, Roger M. Freidinger, Peter D. Williams
  • Patent number: 5720899
    Abstract: A novel liquid crystalline compound having a high elastic constant ratio (K.sub.33 /K.sub.11) and an improved solubility thereof in other liquid crystal materials, at low temperatures, and a liquid crystal composition containing the same are provided. The liquid crystalline compound is expressed by the formula (1): ##STR1## wherein Q represents CF.sub.3, CF.sub.2 H or CFH.sub.2 ; A.sub.1, A.sub.2 and A.sub.3 each independently represent trans-1,4-cyclohexylene group, 1,4-phenylene group, wherein one or more hydrogen atoms on its six-membered ring may be replaced by F, Cl or CN, pyridine-2,5-diyl group or 1,3-pyrimidine-2,5-diyl; ring B represents 1,4-phenylene group or trans-1,4-cyclohexylene group; Z.sub.1, Z.sub.2 and Z.sub.3 each independently represent covalent bond, --C.dbd.C--, --C.tbd.C--, --OCO--, --COO--, --CH.sub.2 O--, --OCH.sub.2 --, --(CH.sub.2).sub.2 -- or --(CH.sub.2).sub.4 --; l and m each independently represent an integer of 0 to 5; o and p each independently represent 0 or 1; L.sub.1 and L.
    Type: Grant
    Filed: December 30, 1996
    Date of Patent: February 24, 1998
    Assignee: Chisso Corporation
    Inventors: Tomoyuki Kondo, Kazutoshi Miyazawa, Atsuko Fujita, Noriyuki Ohnishi, Yasuyuki Goto, Etsuo Nakagawa, Shinichi Sawada
  • Patent number: 5716542
    Abstract: A liquid crystal compound represented by formula (I) and a liquid crystal composition containing the same. The compound exhibits an antiferroelectric liquid crystal phase and has good compatibility with known liquid crystal compounds. ##STR1## wherein R.sup.1 represents a straight-chain or branched alkyl, alkoxy, alkoxycarbonyl, alkanoyloxy or alkoxycarbonyloxy group having 4 to 16 carbon atoms; R.sup.2 represents a straight-chain alkyl group having 4 to 10 carbon atoms or a branched alkyl group containing 1 to 3 carbon atoms in its branch and 4 to 12 carbon atoms in total; X represents an oxygen or sulfur atom; rings A and B each represent an F-substituted or unsubstituted phenylene group, a cyclohexylene group or a divalent nitrogen-containing heterocyclic group, provided that either one of rings A and B is the nitrogen-containing heterocyclic group; ring C represents an F-substituted or unsubstituted phenylene group; and C* represents an asymmetric carbon atom.
    Type: Grant
    Filed: April 24, 1996
    Date of Patent: February 10, 1998
    Assignee: Takasago International Corporation
    Inventors: Yukiharu Iwaya, Mamoru Yamada, Hitoshi Kondo, Toshimitsu Hagiwara
  • Patent number: 5702637
    Abstract: Fluorine-containing, chiral liquid crystal compounds comprise (a) a chiral fluorochemical terminal portion containing at least one methylene group and optionally containing at least one catenary ether oxygen atom; (b) a saturated, chiral or achiral, hydrocarbon terminal portion; and (c) a central core connecting the terminal portions. The compounds have smectic mesophases or latent smectic mesophases and are useful, for example, in liquid crystal display devices.
    Type: Grant
    Filed: April 19, 1995
    Date of Patent: December 30, 1997
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Gilbert C. Johnson, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
  • Patent number: 5686608
    Abstract: A process for preparing polycyclic aromatic compounds by cross-coupling aromatic boron compounds with aromatic halogen compounds or perfluoroalkylsulfonates in the presence of metallic palladium as catalyst comprises adding to the reactiona) at least one water-soluble complexing ligand andb) sufficient water for the reaction mixture to form an aqueous phase.The reaction of the invention proceeds chemoselectively so that even electrophilic groups such as esters or nitriles do not have an adverse effect on the course of the reaction.The use according to the invention of a water-soluble complexing ligand in an aqueous phase enables polycyclic aromatic compounds to be prepared in very good yields and at the same time very high purity, in particular without contamination by the complexing ligands.
    Type: Grant
    Filed: April 24, 1995
    Date of Patent: November 11, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Steffen Haber, Javier Manero
  • Patent number: 5686619
    Abstract: Provided is a process for preparing chloroalkyl pyridinium hydrochloride compounds and various regioisomers and analogs thereof having substantially high purity levels and yields and a free-flowing, non-dusting form.
    Type: Grant
    Filed: March 6, 1995
    Date of Patent: November 11, 1997
    Assignee: Cytec Technology Corp.
    Inventors: William Elliott Bay, Matthew A. Brown, David R. Kilanowski
  • Patent number: 5658489
    Abstract: A diphenylacetylene compound of the formula [1]: ##STR1## wherein R is a C.sub.1 -C.sub.12 alkyl group, a C.sub.2 -C.sub.12 alkenyl group or a C.sub.2 -C.sub.16 alkoxyalkyl group; X.sup.1, X.sup.2, X.sup.3, X.sup.4, Y.sup.1, Y.sup.2, Y.sup.3 and Y.sup.4 are independently from each other a --CH-- group, a --CF-- group or a nitrogen atom;A is a hydrogen atom, a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group, a cyano group, a 4-R.sup.1 -(cycloalkyl) group, 4-R.sup.1 -(cycloalkenyl) group or a R.sup.1 --(O).sub.m group in which R.sup.1 is a C.sub.1 -C.sub.12 alkyl group, a C.sub.2 -C.sub.12 alkenyl group or a C.sub.2 -C.sub.12 alkynyl group; and m is 0 or 1, which has an excellent anisotropy of refractive index and a low viscosity and is useful as a component of a liquid crystal composition.
    Type: Grant
    Filed: October 13, 1994
    Date of Patent: August 19, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takayuki Higashii, Yukari Fujimoto, Masayoshi Minai, Tsutomu Matsumoto
  • Patent number: 5653911
    Abstract: A novel liquid crystalline compound having a high elastic constant ratio (K.sub.33 /K.sub.11) and an improved solubility thereof in other liquid crystal materials, at low temperatures, and a liquid crystal composition containing the same are provided. The liquid crystalline compound is expressed by the formula (1): ##STR1## wherein Q represents CF.sub.3, CF.sub.2 H or CFH.sub.2 ; A.sub.1, A.sub.2 and A.sub.3 each independently represent trans-1,4-cyclohexylene group, 1,4-phenylene group, wherein one or more hydrogen atoms on its six-membered ring may be replaced by F, Cl or CN, pyridine-2,5-diyl group or 1,3-pyrimidine-2,5-diyl; ring B represents 1,4-phenylene group or trans-1,4-cyclohexylene group; Z.sub.1, Z.sub.2 and Z.sub.3 each independently represent covalent bond, --C.dbd.C--, --C.tbd.C--, --OCO--, --COO--, --CH.sub.2 O--, --OCH.sub.2 --, --(CH.sub.2).sub.2 -- or --(CH.sub.2).sub.4 --; l and m each independently represent an integer of 0 to 5; o and p each independently represent 0 or 1; L.sub.1 and L.
    Type: Grant
    Filed: April 27, 1995
    Date of Patent: August 5, 1997
    Assignee: Chisso Corporation
    Inventors: Tomoyuki Kondo, Kazutoshi Miyazawa, Atsuko Fujita, Noriyuki Ohnishi, Yasuyuki Goto, Etsuo Nakagawa, Shinichi Sawada
  • Patent number: 5643914
    Abstract: This invention relates to a compound of formula 1 ##STR1## or an N-oxide, or a pharmaceutically acceptable salt, where A is CH.sub.2 and Z is S(O).sub.q where q is 0, 1 or 2, CH.sub.2, CHOH, CO, NR.sub.x, or O, orA is C.dbd.O and Z is NR.sub.x ;m is 0-5;R.sub.x is hydrogen or lower alkyl;R is C.sub.1 to C.sub.20 -aliphatic, unsubstituted or substituted five-membered heteroaryl-C.sub.1 to C.sub.10 -aliphatic-O--, unsubstituted or substituted phenyl-C.sub.1 to C.sub.10 -aliphatic where substituted p from the group consisting of lower alkoxy, lower alkyl, trihalomethyl, and halo, or R is C.sub.1 to C.sub.20 -aliphatic-O--, or R is unsubstituted or substituted phenyl-C.sub.1 to C.sub.10 -aliphatic-O-- where substituted phenyl has one or more radicals selected from the group consisting of lower alkoxy, lower alkyl, trihalomethyl, and halo;R.sub.1 is R.sub.4, --(C.sub.1 to C.sub.5 aliphatic)R.sub.4, --(C.sub.1 to C.sub.5 aliphatic)CHO, --(C.sub.1 to C.sub.5 aliphatic)CH.sub.2 OR.sub.5;R.sub.2 and R.sub.
    Type: Grant
    Filed: December 19, 1994
    Date of Patent: July 1, 1997
    Assignee: SmithKline Beecham Corporation
    Inventor: Robert A. Daines
  • Patent number: 5633257
    Abstract: Compounds of general formula (1) ##STR1## are described wherein Y is a halogen atom or a group --OR.sup.1, wherein R.sup.1 is an optionally substituted alkyl group; X is --O--, --S--, or --N(R.sup.6), wherein R.sup.6 is a hydrogen atom or an optionally substituted alkyl group; R.sup.2 is an optionally substituted cycloalkyl or cycloalkenyl group; R.sup.3 and R.sup.4, which may be the same or different, is each a hydrogen atom or an optionally substituted alkyl, --CO.sub.2 R.sup.7 (wherein R.sup.7 is a hydrogen atom, am optionally substituted alkyl, aralkyl, aryl, aryloxyalkyl, alkanoyloxyalkyl or aroyloxyalkyl group), --CONR.sup.8 R.sup.9 (where R.sup.8 and R.sup.9, which may be the same or different, is as defined for R.sup.7), --CSNR.sup.8 R.sup.9, --CN or --CH.sub.2 CN group; Z is --(CH.sub.2).sub.n -- where n is zero or an integer 1, 2 or 3; R.sup.
    Type: Grant
    Filed: March 9, 1994
    Date of Patent: May 27, 1997
    Assignee: Celltech Therapeutics Limited
    Inventors: Graham J. Warrellow, Valerie A. Cole, Rikki P. Alexander
  • Patent number: 5629323
    Abstract: Amide Derivatives of formula (I) wherein R.sup.1 is a mono or bicyclic heteroaryl radical, R.sup.2 is cycloalkyl, R.sup.3 and R.sup.4 each represent hydrogen or lower alkyl, and R.sup.5 is a group of formula (A) or (B) or (C): R.sup.8 --CH.sub.2 --CH.sub.2 -- or (D) or (E): R.sup.9 OCH.sub.2 CHOHCH.sub.2 -- or (F): R.sup.9 OCH.sub.2 CH.sub.2 -- and their pharmaceutically acceptable salts are 5-HT.sub.1A binding agents and may be used, for example, as anxiolytics.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: May 13, 1997
    Assignee: John Wyeth & Brother, Ltd.
    Inventors: Ian A. Cliffe, Anderson D. Ifill
  • Patent number: 5618829
    Abstract: A pharmaceutical composition which comprises a pharmaceutically effective amount of a compound of the formula ##STR1## wherein R.sup.1 represents a hydrogen atom,R.sup.2 represents --(CH.sub.2).sub.m -Awherein m is an integer of 0 to 3, andA represents pyridyl which is unsubstituted or is substituted by C.sub.1 -C.sub.3 alkyl said alkyl being unsubstituted or substituted by phenyl, and R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 each independently represent a hydrogen atom, a halogen atom, C.sub.1 -C.sub.5 alkyl which is unsubstituted or is substituted with a halogen atom or --OR.sup.13 wherein R.sup.13 represents a hydrogen atom or C.sub.1 -C.sub.5 alkyl which is unsubstituted or is substituted with a halogen atom or phenyl, or when their adjacent substituents are taken together, they represent C.sub.1 -C.sub.3 oxyalkylene having one or two oxygen atoms;or a pharmaceutically acceptable salt thereof, anda pharmaceutically acceptable carrier therefor.
    Type: Grant
    Filed: January 25, 1994
    Date of Patent: April 8, 1997
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Hisao Takayanagi, Yasunori Kitano, Tamaki Yano, Hiroe Umeki, Hiroto Hara