Halogen Containing Patents (Class 568/588)
  • Patent number: 8674142
    Abstract: The invention relates to the use of polycyclic aromatic hydrocarbons (PAHs) such as naphthalene and its alkyl, aryl, or heteroatom substituted analogs, that act as catalysts in the presence of an alkali metal (Li, K, Na) for the reduction of electron-deficient and electron-rich triaryl phosphines to their corresponding alkali metal diaryl phosphide salts. The process is also useful for the catalysis of triaryl phosphine chalcogen adducts such as the sulfides, oxides, and selenides, diaryl(halo)phosphines, triaryl phosphine-borane adducts, and tetra-aryl bis(phosphines) that can also be reduced to their corresponding alkali metal diaryl phosphide salts. The invention also relates to small molecule PAHs and polymer tethered PAHs naphthenics.
    Type: Grant
    Filed: March 11, 2010
    Date of Patent: March 18, 2014
    Assignee: PMC Organometallix, Inc.
    Inventors: Nicholas J. Rodak, Gary S. Silverman, Stephen W. Carson
  • Publication number: 20130274283
    Abstract: Premature termination codons readthrough compounds, composition thereof, and methods of making and using the same are provided.
    Type: Application
    Filed: February 11, 2013
    Publication date: October 17, 2013
    Applicant: THE REGENTS OF THE UNIVERSITY OF CALIFORNIA
    Inventors: Richard A. GATTI, Liutao DU, Robert DAMOISEAUX, Chih-Hung LAI, Michael JUNG, Jin-Mo KU, Carmen BERTONI
  • Patent number: 8410316
    Abstract: The compound (I) or a salt thereof has an excellent controlling activity against pests. Then the compound (I) or a salt thereof is useful for an active ingredient of a pesticidal composition.
    Type: Grant
    Filed: August 31, 2011
    Date of Patent: April 2, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shigeyuki Itoh, Atsushi Iwata
  • Publication number: 20120178931
    Abstract: Provided is a process by which pyrimidinylacetonitrile derivatives can be prepared easily and efficiently from industrially available raw materials. Also provided are intermediates for the synthesis of the derivatives. A process for the preparation of pyrimidinylacetonitrile derivatives represented by general formula (3) [wherein X is a halogen atom, and R is an alkoxymethyl group], characterized by reacting a 2,4-dihalogeno-6-nitrobenzene derivative represented by general formula (1) [wherein X and R are each as defined above] with 4,6-dimethoxy-2-cyanomethylpyrimidine represented by general formula (2) [wherein Me represents a methyl group] in the presence of a base; and intermediates for the synthesis of the pyrimidinylacetonitrile derivatives.
    Type: Application
    Filed: August 23, 2010
    Publication date: July 12, 2012
    Applicant: IHARA CHEMICAL INDUSTRY CO., LTD
    Inventor: Kentaro Kawazoe
  • Patent number: 7109164
    Abstract: New thyroid receptor ligands are provided which have the general formula in which: X is —O—, —S—, —CH2—, —CO—, or —NH—; Y is —(CH2)n— where n is an integer from 1 to 5, or cis- or trans-ethylene; R1 is halogen, trifluoromethyl, or alkyl of 1 to 6 carbons or cycloalkyl of 3 to 7 carbons; R2 and R3 are the same or different and are hydrogen, halogen, alkyl of 1 to 4 carbons or cycloalkyl of 3 to 6 carbons, at least one of R2 and R3 being other than hydrogen; R4 is hydrogen or lower alkyl; R5 is hydrogen or lower alkyl; R6 is carboxylic acid, or esters or prodrugs; R7 is hydrogen or an alkanoyl or an aroyl. In addition, a method is provided for preventing, inhibiting or treating a disease associated with metabolism dysfunction or which is dependent upon the expression of a T3 regulated gene, wherein a compound as described above is administered in a therapeutically effective amount.
    Type: Grant
    Filed: August 30, 2004
    Date of Patent: September 19, 2006
    Assignee: Bristol-Myers Squibb Company
    Inventors: Todd J. Friends, Denis E. Ryono, Minsheng Zhang
  • Patent number: 7091270
    Abstract: The present invention provides novel pentabromobenzyl alkyl ethers serving as highly effective flame retardants in polymers. The invention further provides a fire retarded polymer composition comprising said pentabromobenzyl alkyl ethers.
    Type: Grant
    Filed: January 23, 2000
    Date of Patent: August 15, 2006
    Assignee: Bromine Compounds Ltd.
    Inventors: Joseph Zilberman, Alon Tavor, Dorit Canfi, David Ioffe, Grigory Titelman, Samuel Bron, Olga Weinberg
  • Patent number: 6800605
    Abstract: New thyroid receptor ligands are provided which have the general formula in which: X is —O—, —S—, —CH2—, —CO—, or —NH—; Y is —(CH2)n— where n is an integer from 1 to 5, or cis- or trans-ethylene; R1 is halogen, trifluoromethyl, or alkyl of 1 to 6 carbons or cycloalkyl of 3 to 7 carbons; R2 and R3 are the same or different and are hydrogen, halogen, alkyl of 1 to 4 carbons or cycloalkyl of 3 to 6 carbons, at least one of R2 and R3 being other than hydrogen; R4 is hydrogen or lower alkyl; R5 is hydrogen or lower alkyl; R6 is carboxylic acid, or esters or prodrugs; R7 is hydrogen or an alkanoyl or an aroyl. In addition, a method is provided for preventing, inhibiting or treating a disease associated with metabolism dysfunction or which is dependent upon the expression of a T3 regulated gene, wherein a compound as described above is administered in a therapeutically effective amount.
    Type: Grant
    Filed: January 16, 2001
    Date of Patent: October 5, 2004
    Assignee: Bristol-Myers Squibb Company
    Inventors: Todd J. Friends, Denis E. Ryono, Minsheng Zhang
  • Patent number: 6576303
    Abstract: Novel liquid crystal compound having a negative and absolutely large value of dielectric anisotropy, being excellent in compatibility with other liquid crystalline compounds at a low temperature and being stable chemically and physically, as well as a liquid crystal composition comprising this compound, and a liquid crystal display device comprising this liquid crystal composition are provided, said compound is expressed by the general formula (1): R1—A1—B1—A2—B2—A3—B3—Z—B4—A4—R2  (1) wherein A1, A2, A3 and A4 represent a single bond, 1,4-cyclohexylene, 1,4-phenylene which may be substituted with a fluorine atom(s) or the like; B1, B2, B3 and B4 represent a single bond, 1,2-ethylene, 1,2-ethenylene, 1,2-ethynylene, oxymethylene, methyleneoxy or the like; R1 and R2 represent an alkyl group having 1 to 10 carbon atoms or the like; and Z represents (I) to (VI): wherein X represents H or F, and Y represents difluoromethyl gr
    Type: Grant
    Filed: August 24, 2000
    Date of Patent: June 10, 2003
    Assignee: Chisso Corporation
    Inventors: Norio Tamura, Atsuko Fujita, Hiroyuki Tekeuchi, Fusayuki Takeshita, Etsuo Nakagawa
  • Patent number: 6462044
    Abstract: The present invention describes novel nitrosated and/or nitrosylated phosphodiesterase inhibitors, and novel compositions containing at least one nitrosated and/or nitrosylated phosphodiesterase inhibitor, and, optionally, one or more compounds that donate, transfer or release nitric oxide, elevate endogenous levels of endothelium-derived relaxing factor, stimulate endogenous synthesis of nitric oxide or is a substrate for nitric oxide synthase and/or one or more vasoactive agents. The present invention also provides novel compositions containing at least one phosphodiesterase inhibitor, and one or more compounds that donate, transfer or release nitric oxide, elevate endogenous levels of endothelium-derived relaxing factor, stimulate endogenous synthesis of nitric oxide or is a substrate for nitric oxide synthase and/or one or more vasoactive agents.
    Type: Grant
    Filed: August 30, 2001
    Date of Patent: October 8, 2002
    Assignee: NitroMed, Inc.
    Inventors: David S. Garvey, Inigo Saenz de Tejada, Richard A. Earl, Subhash P. Khanapure
  • Patent number: 6448449
    Abstract: A process for the preparation of (R)-1-(2,3-difluoro-6-nitrophenoxy)-propan-2-ol, which is a useful intermediate in the synthesis of the widely used antibiotic Levofloxacin is provided. A process for the preparation of (R)-1-(2,3-difluoro-6-nitrophenoxy)-2-trimethylsiloxypropane is also described. The process includes the ring opening of (R)-propylene oxide with 2,3-difluoro-6-nitrophenyl trimethylsilyl ether in the presence of an optically active Co(salen) catalyst. The trimethylsilyl group of the reactant is transferred to the product aryloxy alcohol, which serves to protect the secondary alcohol in situ. Upon isolation, the trimethylsilyl group is removed and the resulting regioisomeric mixture purified to yield the desired (R)-1-(2,3-difluoro-6-nitrophenoxy)-propan-2-ol in high purity and yield.
    Type: Grant
    Filed: April 20, 2001
    Date of Patent: September 10, 2002
    Assignee: Rhodia ChiRex, Inc.
    Inventor: Jay Francis Larrow
  • Patent number: 6333080
    Abstract: A liquid crystalline alkenyltolan derivative expressed by the general formula CtH2t−1—G—(CH2)m—A1—B1—(A2—B2)n—(A3—B3)p—A4—X wherein A1, A2, A3, and A4 independently represent a 1,4-cyclohexylene, 1,4-phenylene in which one or two hydrogen atoms may be replaced by a fluorine atom(s), dioxane-2,5-diyl, or pyrimidine-2,5-diyl group; B1, B2, and B3 independently represent a covalent bond, an 1,2-ethylene, 1,2-ethenylene, 1,2-ethynylene, oxymethylene, methylenoxy, carbonyloxy, or 1,4-butylene group provided that at least one of B1, B2, and B3 represents an 1,2-ethynylene group; G represents a covalent bond or an oxygen atom; CtH2t−1 represents an alkenyl group having t carbon atoms; n and p are each 0 or 1; and X represents an alkyl group having 1 to 10 carbon atoms.
    Type: Grant
    Filed: May 6, 1999
    Date of Patent: December 25, 2001
    Assignee: Chisso Corporation
    Inventors: Norio Tamura, Atsuko Fujita, Shuichi Matsui, Kazutoshi Miyazawa, Norihisa Hachiya, Etsuo Nakagawa
  • Patent number: 6331543
    Abstract: The present invention describes novel nitrosated and/or nitrosylated phosphodiesterase inhibitors, and novel compositions containing at least one nitrosated and/or nitrosylated phosphodiesterase inhibitor, and, optionally, one or more compounds that donate, transfer or release nitric oxide, elevate endogenous levels of endothelium-derived relaxing factor, stimulate endogenous synthesis of nitric oxide or is a substrate for nitric oxide synthase and/or one or more vasoactive agents. The present invention also provides novel compositions containing at least one phosphodiesterase inhibitor, and one or more compounds that donate, transfer or release nitric oxide, elevate endogenous levels of endothelium-derived relaxing factor, stimulate endogenous synthesis of nitric oxide or is a substrate for nitric oxide synthase and/or one or more vasoactive agents.
    Type: Grant
    Filed: September 1, 1999
    Date of Patent: December 18, 2001
    Assignee: NitroMed, Inc.
    Inventors: David S. Garvey, Inigo Saenz de Tejada, Richard A. Earl, Subhash P. Khanapure
  • Patent number: 6316658
    Abstract: N-Cyclopropyl-2-difluoromethoxy-3-halogenoanilines which serve as important intermediates in the preparation of quinolonecarboxylic acids useful as synthetic antimicrobial agents from industrially inexpensive and easily available raw materials; and intermediates for the preparation thereof. Specifically, compounds represented by the general formula (1), (2) and (3), wherein X is halogeno; and Y is nitro or amino, (2) wherein X is halogeno; and R1 is lower alkyl, (3) wherein X is halogeno; and R is hydrogen or —CH═C(CO2R2)2, R2 being lower alkyl.
    Type: Grant
    Filed: April 11, 2000
    Date of Patent: November 13, 2001
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Yasuo Yoshida, Hiroaki Takeuchi
  • Patent number: 6172268
    Abstract: A method for producing an optically active 1-substituted 2-propanol of the following formula 1, which comprises reacting a hydroxy aromatic compound of the following formula 2 with an optically active propylene oxide in the presence of a catalyst: AOH  Formula 2 CH3C*H(OH)CH2OA  Formula 1 wherein A is a univalent aromatic group, and C* is an asymmetric carbon atom.
    Type: Grant
    Filed: January 28, 2000
    Date of Patent: January 9, 2001
    Assignee: Asahi Glass Company, Limited
    Inventors: Toshihiko Tohma, Tomoyuki Asai
  • Patent number: 5998636
    Abstract: Substituted N-phenyl- and N-heteroarylalkylcarbamates of the formula I ##STR1## in which Q is a group ##STR2## R is halogen, trifluoromethyl, cyano, nitro or C.sub.1 -C.sub.3 haloalkoxy;Z is hydrogen or halogen; orZ and R together in the 2- and 3-position of the phenyl ring form a group --OCF.sub.2 O--;R.sub.1 is C.sub.1 -C.sub.5 alkyl;R.sub.2, R.sub.3, R.sub.4 and R.sub.5, independently of one another, are hydrogen, methyl or ethyl;X is oxygen, sulfur, --SO-- or --SO.sub.2 --;Y is hydrogen, halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkoxy or cyano;n is 0, 1 or 2;n.sub.1 is 0 or 1; andm is 0 or 1,with the proviso that m is 1 if Q is group (1) or (2);and the diastereomers and enantiomers thereof,exhibit pre- and post-emergence herbicidal properties. The preparation of these compounds and their use as herbicidally active ingredients are described.
    Type: Grant
    Filed: August 4, 1998
    Date of Patent: December 7, 1999
    Assignee: Novartis Finance Corporation
    Inventors: Hermann Rempfler, Fredrik Cederbaum, Felix Spindler, Willy Urs Lottenbach
  • Patent number: 5871675
    Abstract: The invention relates to a novel process for the production of tinted mouldings, in particular tinted contact lenses, in which a crosslinkable tinted polymer comprising units containing a crosslinkable group and units containing a reactive dye radical is crosslinked in solution, and to tinted mouldings, in particular tinted contact lenses, obtainable by this process.
    Type: Grant
    Filed: September 18, 1997
    Date of Patent: February 16, 1999
    Assignee: Novartis AG.
    Inventors: Achim Muller, Thomas Pohlmann, Bernhard Seiferling
  • Patent number: 5831114
    Abstract: Substituted N-phenyl- and N-heteroarylalkylcarbamates of formula (I), in which Q is a group (1), (2) or (3); R is halogen, trifluoromethyl, cyano, nitro or C.sub.1 -C.sub.3 haloalkoxy; Z is hydrogen or halogen; or Z and R together in the 2- and 3-position of the phenyl ring form a group --OCF.sub.2 O--; R.sub.1 is C.sub.1 -C.sub.5 alkyl; R.sub.2, R.sub.3, R.sub.4 and R.sub.5, independently of one another, are hydrogen, methyl or ethyl; X is oxygen, sulfur, --SO-- or --SO.sub.2 --, Y is hydrogen, halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkoxy or cyano; n is 0, 1 or 2; n.sub.1 is 0 or 1; and m is 0 or 1, with the proviso that m is 1 if Q is group (1) or (2); and the diastereomers and enantiomers thereof, exhibit pre- and post-emergence herbicidal properties. The preparation of these compounds and their use as herbicidally active ingredients are described.
    Type: Grant
    Filed: May 28, 1997
    Date of Patent: November 3, 1998
    Assignee: Novartis Finance Corporation
    Inventors: Hermann Rempfler, Fredrik Cederbaum, Felix Spindler, Willy Urs Lottenbach
  • Patent number: 5643495
    Abstract: 1,2,2,2-Tetrafluoroethyl ethers of the formula IR--(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --Z.sup.2 A.sup.3 --O--CHF--CF.sub.3(I)are suitable as components of liquid-crystalline media whereinR is H, a substituted or unsubstituted alkyl or alkenyl radical having 1 to 15 carbon atoms,A.sup.1 and A.sup.2 are each, independently of one another, a(a) trans-1,4-cyclohexylene radicals and derivatives thereof in which, in addition, one or more non-adjacent CH.sub.2 groups is optionally replaced by --O-- and/or --S--,(b) 1,4-phenylene radicals and derivatives thereof in which, in addition, one or two CH groups is optionally replaced by N, or(c) radical from the group consisting of 1,4-cyclohexenylene, 1,4-bicyclo(2,2,2)octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl and 1,2,3,4-tetrahydronaphthalene-2,6-diyl,wherein radicals (a) and (b) are optionally substituted by one or two fluorine atoms,Z.sup.1 and Z.sup.2 are each, independently of one another, --CO--O--, --O--CO--, --CH.sub.
    Type: Grant
    Filed: September 12, 1995
    Date of Patent: July 1, 1997
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Ekkehard Bartmann, Ulrich Finkenzeller
  • Patent number: 5585036
    Abstract: This invention provides chiral nonracemic compounds of general formula I which are useful as components of FLC compositions in SSFLC and DHFLC devices: ##STR1## wherein Z is a C.dbd.O group or a CH.sub.2 group, R.sub.F is a partially or fully fluorinated alkyl or alkenyl group, R.sub.2 is selected from an alkyl, alkenyl or alkynyl group in which one or more CH.sub.2 groups can optionally be substituted with one or two halogen atoms or in which one or more non-neighboring CH.sub.2 can be replaced with an O, S or an alkyl silyl group, S.sub.1 (R.sub.A)(R.sub.B), in which R.sub.A and R.sub.B, independently of one another, are small alkyl or alkenyl groups having from one to six carbon atoms, * indicates the chiral carbon and where Ar can be a one, two, or three aromatic ring LC core moieties. In particular, the core can have one to three, aromatic rings which are optionally linked by linking groups including O, S, CH.sub.2 S, SCH.sub.2, CH.sub.2 CH.sub.2, CH.sub.2 O, OCH.sub.2, CH.sub.2 CO.sub.2, CH.sub.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: December 17, 1996
    Assignee: Displaytech, Inc.
    Inventors: Michael D. Wand, Kundalika M. More, William N. Thurmes
  • Patent number: 5463138
    Abstract: Difluoromethoxyarenes and difluoromethylthioarenes of the general formula (I),Ar--Q--CHF.sub.2 (I)in whichAr represents optionally substituted aryl, andQ represents oxygen or sulphur,(which can be used as intermediates for preparing biologically active products) are obtained in very good yields and in a high degree of purity by reacting hydroxyarenes or mercaptoarenes of the general formulaAr--Q--H (II)with chlorodifluoromethane (ClCHF.sub.2) in the presence of an aqueous alkali metal hydroxide or alkaline earth metal hydroxide at temperatures of between 20.degree. C. and 120.degree. C.
    Type: Grant
    Filed: May 18, 1994
    Date of Patent: October 31, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventor: Klaus-Helmut Muller
  • Patent number: 5453218
    Abstract: This invention provides chiral nonracemic compounds of formula ##STR1## wherein * indicates a chiral carbon, R.sub.1 and R.sub.2, independently of one another, can be an alkyl, alkenyl or alkynyl group wherein one or more non-neighboring CH.sub.2 groups can be replaced with an O, S or a silyl group (R.sub.A SiR.sub.B) wherein R.sub.A and R.sub.B, independently of one another, are alkyl or alkenyl having from one to six carbon atoms; R.sub.1 having from about 3 to 20 carbon atoms, and R.sub.2 having from 1 to about 18 carbon atoms; X is O, S, CO, COO, OCO, COS or a single bond where Ar is a liquid crystal core moiety having two or three aromatic rings of the formula--(Cyc).sub.n --(A).sub.a --Ph.sub.1 --(B).sub.b --Ph.sub.2 --(C).sub.c --(Ph.sub.3).sub.m --whereinPh.sub.1, Ph.sub.2 and Ph.sub.
    Type: Grant
    Filed: February 8, 1994
    Date of Patent: September 26, 1995
    Assignee: Displaytech, Inc.
    Inventors: Michael D. Wand, Kundalika M. More, William N. Thurmes
  • Patent number: 5446186
    Abstract: The synthesis and compound of a new caged calcium which is an ortho-nitrophenyl derivative of EGTA and various intermediates. It is synthesized in ten steps and 24% overall yield. The photosensitive chelator, nitrophenyl-EGTA, has a K.sub.d for Ca.sup.2+ of 80 nM and for Mg.sup.2+ of 8.8 mM. Upon exposure to ultra-violet light (in the region of 350 nm), the chelator is cleaved, yielding iminodiacetic acid photoproducts with known low Ca-affinity (K.sub.d =1 mM). The quantum yield of photolysis of nitrophenyl-EGTA in the presence of Ca.sup.a+ is 0.23 and in the absence of Ca.sup.2+ is 0.20. In experiments with chemically skinned skeletal muscle fibers, a fully relaxed fiber equilibrated with nitrophenyl-EGTA:Ca.sup.2+ complex, in the presence of physiological [Mg.sup.2+ ] (i.e. 1.0 mM), produced maximal contraction after a single flash from a frequency doubled ruby laser (347 nm). Half-maximal tension was achieved in 18 ms at 15.degree. C.
    Type: Grant
    Filed: November 9, 1993
    Date of Patent: August 29, 1995
    Inventors: Graham C. R. Ellis-Davies, Jack H. Kaplan
  • Patent number: 5401436
    Abstract: An optically active compound of the formula (I): ##STR1## R is a halogen atom, a cyano group, an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, --R' or --O--R' group; R' is a ##STR2## group, wherein Y is a halogen atom, a hydroxyl group, an alkoxy group having 1 to 18 carbon atoms or an acyloxy group having 1 to 18 carbon atoms; X is a direct bond or a ##STR3## group; m, n and p each are each 0 or 1, provided that at least one of m, n and p is 1; and , represents an asymetric carbon atom.
    Type: Grant
    Filed: December 11, 1992
    Date of Patent: March 28, 1995
    Assignee: Asahi Denka Kogko Kabushiki Kaisha
    Inventors: Seiichi Takano, Kunio Ogasawara, Toshihiro Shibata, Masaki Kimura, Norio Kurosawa
  • Patent number: 5393776
    Abstract: This invention relates to structurally novel acyclic tocotrienol analogs, which are useful for cholesterol/lipid lowering in cases of hypercholesterolemia and hyperlipidemia, and for atherosclerosis. Also provided are pharmaceutical compositions and a method of use employing those compositions.
    Type: Grant
    Filed: May 13, 1994
    Date of Patent: February 28, 1995
    Assignee: Bristol-Myers Squibb Company
    Inventor: Bradley C. Pearce
  • Patent number: 5393885
    Abstract: Compounds of the formula ##STR1## in which R.sub.1 is halogen, C.sub.1 -C.sub.3 alkyl, halo-C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, halo-C.sub.1 -C.sub.3 alkoxy or cyano and/or two substituents R.sub.1 which are bonded to adjacent C atoms of the phenyl ring together are --O--CH.sub.2 --O--; R.sub.2 is hydrogen, halogen or methyl;R.sub.3 is fluorine, chlorine, bromine or C.sub.1 -C.sub.3 alkyl; R.sub.4 is hydrogen or C.sub.1 -C.sub.3 alkyl;either R.sub.5 is hydrogen, C.sub.1 -C.sub.4 alkyl, ##STR2## --COCO--R.sub.8,--CO--R.sub.9 or S(O).sub.m --N(R.sub.10)--COO--R.sub.11 andR.sub.6 is C.sub.1 -C.sub.6 alkyl, halo-C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.6 alkenyl, halo-C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.5 alkynyl, halo-C.sub.3 -C.sub.5 alkynyl, C.sub.1 -C.sub.3 alkoxy-C.sub.1 -C.sub.3 alkyl, C.sub.3 -C.sub.6 cycloalkyl, unsubstituted or substituted phenyl; or R.sub.5 and R.sub.6 together are --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 --; R.sub.7 is hydrogen, halogen or C.sub.1 -C.sub.3 alkyl; R.
    Type: Grant
    Filed: February 22, 1994
    Date of Patent: February 28, 1995
    Assignee: Ciba-Geigy Corporation
    Inventor: Friedrich Karrer
  • Patent number: 5290477
    Abstract: An optically active compound represented by formula (I): ##STR1## wherein R.sup.1 represents an alkyl group having from 3 to 9 carbon atoms; R.sup.2 represents an alkyl group having from 3 to 7 carbon atoms; m and n each represent 1 or 2 provided that they do not simultaneously represent 1; and C.sup.*1 and C.sup.*2, both represent an optically active carbon atom, and a liquid crystal composition containing the same are disclosed. The compound exhibits chiral nematic and smectic phases and are excellent as a chiral dopant for ferroelectric liquid crystal compositions or nematic liquid crystal compositions.
    Type: Grant
    Filed: July 29, 1993
    Date of Patent: March 1, 1994
    Assignee: Takasago International Corporation
    Inventors: Hitoshi Kondo, Mika Tadokoro, Hiroshi Sugiyama, Toshimitsu Hagiwara, Takashi Imai, Mamoru Yamada, Keisuke Itakura
  • Patent number: 5225607
    Abstract: This invention relates to novel fluorinated ethers, useful as insecticides and acaricides, to processes and intermediates for their preparation, to insecticidal and acaricidal compositions thereof and to methods of combating and controlling insect and acarine pests therewith.
    Type: Grant
    Filed: December 30, 1987
    Date of Patent: July 6, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael J. Bushell, Robin A. E. Carr, Alan J. Whittle
  • Patent number: 5220076
    Abstract: The invention relates to new peroxide perfluoropolyethers having formula: ##STR1## wherein: A and B are end groups,X represents a (R'O).sub.m R" group where R' is selected from the class consisting of --CF.sub.2 --, --CF.sub.2 --CF.sub.2 -- and ##STR2## and R" is a perfluoroalkyl group; the value of "m" ranging from 0 to 6. The invention relates also to processes for preparing said perfluoropolyethers and other classes of non peroxide perfluoropolyethers derived therefrom.
    Type: Grant
    Filed: May 29, 1992
    Date of Patent: June 15, 1993
    Assignee: Ausimont S.r.l.
    Inventors: Antonio Marraccini, Antonio Pasquale, Anna M. Staccione, Giuseppe Marchionni
  • Patent number: 5200111
    Abstract: An optically active compound of the formula (I): ##STR1## R is a halogen atom, a cyano group, an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms --R' or --O--R' group; R' is a ##STR2## group, wherein Y is a halogen atom, a hydroxyl group, an alkoxy group having 1 to 18 carbon atoms or an acyloxy group having 1 to 18 carbon atoms; X is a direct bond or a ##STR3## group; m, n and p each are each 0 or 1, provided that at least one of m, n and p is 1; and * represents an asymetric carbon atom. The optically active compound can impart a desired helical pitch to a liquid crystal composition.
    Type: Grant
    Filed: March 20, 1989
    Date of Patent: April 6, 1993
    Assignee: Asahi Denka Kogyo Kabushiki Kaisha
    Inventors: Seiichi Takano, Kunio Ogasawara, Toshihiro Shibata, Masaki Kimura, Norio Kurosawa
  • Patent number: 5183587
    Abstract: A liquid crystal compound having a relatively low viscosity, a superior compatibility with other liquid crystalline compounds and suitable for preparing a liquid crystal device having a high response rate, and a superior liquid crystal composition containing the compound are provided, which compound is expressed by the formula ##STR1## wherein R.sup.1 is H, F, Cl, CN or 1-20C alkyl or alkenyl in which alkenyl one --CH.sub.2 -- group or two not adjacent --CH.sub.2 -- groups may be replaced by --O-- and in which alkenyl the position and number of the double bond may be optionally chosen; A.sup.1, A.sup.2 and A.sup.3 are ##STR2## the H atom(s) of which ##STR3## may be replaced by F, Cl or methyl; B.sup.1 and B.sup.2 are --CH.sub.2 CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 -- or single bond; n is 0 or 1; and m is 0 to 20.
    Type: Grant
    Filed: December 22, 1989
    Date of Patent: February 2, 1993
    Assignee: Chisso Corporation
    Inventors: Kisei Kitano, Makoto Ushioda, Manabu Uchida, Toshiharu Suzuki
  • Patent number: 5136114
    Abstract: The invention relates to a new process for the preparation of geminal diarylalkanes of the formula ##STR1## by Friedel-Crafts alkylation of aromatic compounds with specific aliphatic halogen compounds (addition compounds of CCl.sub.4 , to .alpha.-olefins), to new geminal diarylalkanes and the aralkyl compounds resulting as intermediates.
    Type: Grant
    Filed: April 30, 1990
    Date of Patent: August 4, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventor: Dieter Arlt
  • Patent number: 5105021
    Abstract: A higher yield of the difluorohalomethoxybenzene produced by the reaction of a metal phenolate with dibromodifluoromethane or bromochlorodifluoromethane can be obtained by conducting the addition of a metal alcoholate or a metal hydride as a reaction initiator to a solution or a suspension of an aprotic polar solvent containing the metal phenolate and dibromodifluoromethane or bromochlorodifluoromethane.
    Type: Grant
    Filed: April 12, 1990
    Date of Patent: April 14, 1992
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Hideyuki Akieda, Naoki Sato, Koichi Morinaga, Yoshinori Ide, Ryuichi Mita, Mitsumasa Umemoto
  • Patent number: 5104559
    Abstract: A lubricating compound having the structure:R.sup.1 --R.sub.f --O--Ar--R.sup.2wherein R.sup.1 is a monovalent radical selected from the group consisting of fluoride, unsubstituted aryloxys, substituted aryloxys, unsubstituted arylthios, substituted arylthios, perfluoroalkoxys, and perfluoro (3,6-dimethyl-1, 4-dioxanyl-2-oxy), R.sup.
    Type: Grant
    Filed: November 26, 1990
    Date of Patent: April 14, 1992
    Assignee: The Dow Chemical Company
    Inventors: Chester E. Pawloski, Muthiah N. Inbasekaran
  • Patent number: 5105020
    Abstract: The invention concerns a cycloalkane derivative of the formula I, ##STR1## wherein Ar.sup.1 is optionally substituted phenyl or naphthyl;A.sup.1 is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo(3-6C)alkylene;Ar.sup.2 is optionally substituted phenylene, or a 6 membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 is hydrogen, (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl, cyano-(1-4C)alkyl or (2-4C)alkanoyl, or optionally substituted banzoyl; andR.sup.2 and R.sup.3 together form a (3-6C)alkylene group which defines an optionally substituted ring having 4 to 7 ring atoms; or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.
    Type: Grant
    Filed: December 22, 1989
    Date of Patent: April 14, 1992
    Assignees: Imperial Chemistries Industries PLC, ICI Pharma
    Inventor: Jean-Marc M. M. Girodeau
  • Patent number: 5030761
    Abstract: A compound of the formula: ##STR1## wherein X is a chlorine atom or a bromine atom, which is useful as a herbicide.
    Type: Grant
    Filed: November 21, 1983
    Date of Patent: July 9, 1991
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Eiki Nagano, Shunich Hashimoto, Ryo Yoshida, Hiromichi Oshio, Katsuzo Kamoshita
  • Patent number: 5030760
    Abstract: A compound of the formula: ##STR1## wherein X is a chlorine atom or a bromine atom and R is a C.sub.1 -C.sub.8 alkyl group except isopropyl, which is useful as a herbicide.
    Type: Grant
    Filed: September 18, 1984
    Date of Patent: July 9, 1991
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Eiki Nagano, Shunichi Hashimoto, Ryo Yoshida, Hiroshi Matsumoto, Katsuzo Kamoshita
  • Patent number: 5013475
    Abstract: An optically active ester compound useful as a component of a ferroelectric liquid crystal composition is represented by the following formula: ##STR1## wherein R is C.sub.1-18 alkyl or C.sub.1-18 alkoxyl; R' is C.sub.1-18 alkyl or C.sub.
    Type: Grant
    Filed: October 27, 1989
    Date of Patent: May 7, 1991
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Toshihiro Shibata, Masaki Kimura, Norio Kurosawa
  • Patent number: 4997987
    Abstract: Preparation of 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) from 3,5-dichloroanisole. Nitration of 3,5-dichloroanisole under relatively mild conditions gave 3,5-dichloro-2,4,6-trinitroanisole in high yield and purity. Ammonolysis of this latter compound gave the desired TATB. Another route to TATB was through the treatment of the 3,5-dichloro-2,4,6-trinitroanisole with thionyl chloride and dimethylformamide to yield 1,3,5-trichloro-2,4,6-trinitrobenzene. Ammonolysis of this product produced TATB.
    Type: Grant
    Filed: June 8, 1990
    Date of Patent: March 5, 1991
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventors: Donald G. Ott, Theodore M. Benziger
  • Patent number: 4968836
    Abstract: The invention relates to a process for the preparation of cyclopropanecarbaldehydes of formula ##STR1## in which R.sub.1 is C.sub.1 -C.sub.4 alkyl or benzyl, which comprises (a) reacting a tetrahydrofuran of formula ##STR2## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 -cycloalkyl that is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro or cyano, with a halogenating agent to form a 1,2,4-trihalobutyl ether of formula ##STR3## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 cycloalkyl that is unsubstituted or substituted by halogen C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.
    Type: Grant
    Filed: January 30, 1990
    Date of Patent: November 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans-Ruedi Kanel, John G. Dingwall
  • Patent number: 4960950
    Abstract: Disclosed is a novel process for effecting an ether interchange reaction by heating together in the presence of a basic catalyst, a nitroaromatic ether or thioether and an organic compound containing at least one hydroxyl or mercapto group. The novelty resides particularly in carrying out the interchange in an inert solvent while sparging the heated reactants thereby to remove at least a portion of solvent along with an evolving alcohol or thiol.The process is particularly adapted to the capping of organic polyols with nitroaromatic ether groups. The capped products are useful as intermediates for the preparation of high molecular weight polyamines which in turn find utility in various polymer applications.
    Type: Grant
    Filed: March 28, 1988
    Date of Patent: October 2, 1990
    Assignee: The Dow Chemical Company
    Inventor: Visweswara R. Durvasula
  • Patent number: 4952733
    Abstract: Preparation of 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) from 3,5-dichloroanisole. Nitration of 3,5-dichloroanisole under relatively mild conditions gave 3,5-dichloro-2,4,6-trinitroanisole in high yield and purity. Ammonolysis of this latter compound gave the desired TATB. Another route to TATB was through the treatment of the 3,5-dichloro-2,4,6-trinitroanisole with thionyl chloride and dimethylformamide to yield 1,3,5-trichloro-2,4,6-trinitrobenzene. Ammonolysis of this product produced TATB.
    Type: Grant
    Filed: December 21, 1988
    Date of Patent: August 28, 1990
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventors: Donald G. Ott, Theodore M. Benziger
  • Patent number: 4876376
    Abstract: A process for the halogenation (bromination or chlorination)/nitration/fluorination of aromatic derivatives substituted by at least one group containing a halogenoalkyl unit. The aromatic derivative is reacted with a halogen and a nitrating agent in liquid hydrofluoric acid. The products obtained are useful as intermediates for the synthesis of compounds having a plant-protecting or pharmaceutical activity.
    Type: Grant
    Filed: December 15, 1987
    Date of Patent: October 24, 1989
    Assignee: Rhone-Poulenc Specialistes Chimiques
    Inventors: Michael Desbois, Camille Disdier
  • Patent number: 4837364
    Abstract: A process for the preparation of (pentafluoroethoxy)- and (pentafluoroethylthio)benzene derivatives either from phenol, thiophenol or from halobenzene. A halobenzene is reacted with trifluoroethanol or a phenol or a thiophenol is reacted with a compound of the formula CF.sub.3 --CH.sub.2 --O--R'. The product is chlorinated and the chlorinated product is fluorinated in liquid hydrofluoric acid in the presence of a Lewis acid.The compounds obtained by the process of the present invention are used as synthesis intermediates in the phytosanitary, pharmaceutical and veterinary industries, and are used in lubricants.
    Type: Grant
    Filed: March 28, 1986
    Date of Patent: June 6, 1989
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventors: Michel Desbois, Bernard Langlois
  • Patent number: 4816596
    Abstract: A process for preparing substituted or unsubstituted trifluoroethoxy- or trifluoroethylthiobenzenes by reaction of a phenol or thiophenol, both of which may be substituted or unsubstituted, with a compound of the formula CF.sub.3 --CH.sub.2 --O--R', where R' is a moiety selected from the group consisting of trifluoroacetyl, methanesulfonyl, paratoluenesulfonyl, trichloromethanesulfonyl and chlorosulfonyl, in the presence of a strong alkaline base and a complexing agent of the formula:N--CHR.sub.1 --CHR.sub.2 --O--(CHR.sub.3 --CHR.sub.4 --O).sub.n --R.sub.5 ].sub.3 (II)wherein n is an integer from 0 to 10 (0 is less than or equal to n is less than or equal to 10), R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be identical or different, are selected from the group consisting of a hydrogen atom and an alkyl moiety having from 1 to 4 carbon atoms, and R.sub.5 denotes an alkyl or cycloalkyl moiety having from 1 to 12 carbon atoms, a phenyl moiety or a moiety of the formula: --C.sub.m H.sub.2m --C.sub.6 H.sub.
    Type: Grant
    Filed: March 28, 1986
    Date of Patent: March 28, 1989
    Assignee: Rhone-Polenc Specialites Chimoues
    Inventor: Bernard Langlois
  • Patent number: 4766243
    Abstract: A process for the electrophilic ring fluorination of aromatic compounds which comprises reacting a fluorinating agent from the group consisting of CF.sub.3 OF and CF.sub.2 (OF).sub.2 with an aromatic compound of the formula ##STR1## where X is selected from the group consisting of ##STR2## and ##STR3## and Y is selected from the group consisting of --H, --CF.sub.3, --CN, --NO.sub.2, --Cl, and CH.sub.3.
    Type: Grant
    Filed: August 10, 1984
    Date of Patent: August 23, 1988
    Assignee: Occidental Chemical Corporation
    Inventor: Michael J. Fifolt
  • Patent number: 4736068
    Abstract: A compound of the formula: ##STR1## wherein X is a chlorine atom or a bromine atom and R is a C.sub.3 -C.sub.4 alkenyl group or a C.sub.3 -C.sub.4 alkynyl group, which is useful as a herbicide.
    Type: Grant
    Filed: September 3, 1986
    Date of Patent: April 5, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Eiki Nagano, Shunichi Hashimoto, Ryo Yoshida, Hiroshi Matsumoto, Katsuzo Kamoshita
  • Patent number: 4695657
    Abstract: A process for the preparation of compounds containing a difluoromethylene group in a position .alpha. to an oxygen atom. An alcohol or a phenol is brought into contact with trifluoroacetic acid or a halide or anhydride thereof in anhydrous liquid hydrofluoric acid, in the presence of boron trifluoride, in a quantity such that the absolute pressure of boron trifluoride is at least about one bar. The compounds obtained according to the invention are used as synthesis intermediates in the pharmaceutical, plant-protection, and dye industries, as anesthetics and as additives for lubricating oils.
    Type: Grant
    Filed: December 17, 1985
    Date of Patent: September 22, 1987
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Michel Desbois
  • Patent number: 4678811
    Abstract: New substituted benzyl-type ethers of formula I ##STR1## in which R.sub.1 is aryl or aryl substituted by C.sub.1-4 -alkyl, halo-C.sub.1-4 -alkyl, phenyl-C.sub.1-4 -alkyl, C.sub.2-4 -alkenyl, halo-C.sub.2-4 -alkenyl, phenyl-C.sub.2-4 -alkenyl, C.sub.2-4 -alkynyl, halo-C.sub.2-4 -alkynyl, phenyl-C.sub.2-4 -alkynyl, C.sub.1-4 -alkoxy, halo-C.sub.1-4 -alkoxy, phenyl-C.sub.1-4 -alkoxy, C.sub.2-4 -alkenyloxy, halo-C.sub.2-4 -alkenyloxy, phenyl-C.sub.2-4 -alkenyloxy, C.sub.2-4 -alkynyloxy, halo-C.sub.2-4 -alkynyloxy, phenyl-C.sub.2-4 -alkynyloxy, alkylsulfonyloxy, haloalkylsulfonyloxy, arylsulfonyloxy, halo, cyano, nitro, aryloxy, haloaryloxy, C.sub.1-4 -alkyl-aryloxy, or nitroaryloxy,R.sub.2 is hydrogen or C.sub.1-4 alkyl,R.sub.3 is hydrogen, cyano or ethynyl,R.sub.4 is phenyl or pyridyl or one of these groups substituted by one or more of C.sub.1-6 -alkyl, halo-C.sub.1-6 -alkyl, phenyl-C.sub.1-6 -alkyl, C.sub.1-6 -alkyl interrupted by an O--, N-- or S-- atom, C.sub.2-4 -alkenyl, halo-C.sub.2-4 -alkenyl, phenyl-C.
    Type: Grant
    Filed: October 17, 1985
    Date of Patent: July 7, 1987
    Assignee: Schering Aktiengesellschaft
    Inventors: Helga Franke, Heinrich Franke, Hans-Rudolf Kruger, Hartmut Joppien
  • Patent number: 4595763
    Abstract: Aromatic hydroxyl- or thiol-containing compounds are methylated by contacting with methyl trichloroacetate at elevated temperatures in the presence of an initiator.
    Type: Grant
    Filed: June 27, 1983
    Date of Patent: June 17, 1986
    Assignee: The Dow Chemical Company
    Inventors: James M. Renga, Pen-Chung Wang
  • Patent number: 4558040
    Abstract: Certain miticidal (2-alkyl-3,4-dihydro-2H-1-benzopyran-8-yl)diazenecarboxylic acid esters.
    Type: Grant
    Filed: December 3, 1984
    Date of Patent: December 10, 1985
    Assignee: Shell Oil Company
    Inventors: Kurt H. Pilgram, Richard D. Skiles