Polycyclo Ring System Patents (Class 568/929)
  • Patent number: 9364803
    Abstract: The invention generally relates to methods for forming mixed droplets. In certain embodiments, methods of the invention involve forming a droplet, and contacting the droplet with a fluid stream, wherein a portion of the fluid stream integrates with the droplet to form a mixed droplet.
    Type: Grant
    Filed: February 10, 2012
    Date of Patent: June 14, 2016
    Assignee: Raindance Technologies, Inc.
    Inventors: Yevgeny Yurkovetsky, Darren Roy Link, Jonathan William Larson
  • Publication number: 20150141712
    Abstract: The present invention relates to a novel a process for the preparation of 9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-ylamine which process comprises a) reacting cyclopentadiene in the presence of a radical initiator and CXCl3, wherein X is chloro or bromo, to a compound of formula I1, or aa) reacting cyclopentadiene with CXCl3, wherein X is chloro, in the presence of a metal catalyst to a compound of formula I1, wherein X is chloro, b) reacting the compound of formula I1 with a base in the presence of an appropriate solvent to the compound of formula III, c) and converting the compound of formula III in the presence of 1,2-dehydro-6-nitrobenzene to the compound of formula IV, and d) hydrogenating the compound of formula IV in the presence of a metal catalyst.
    Type: Application
    Filed: January 23, 2015
    Publication date: May 21, 2015
    Applicants: SYNGENTA PARTICIPATIONS AG, SYNGENTA CROP PROTECTION LLC
    Inventors: Denis Gribkov, Bjorn Antelmann, Fanny Giordano, Harald Walter, Alain De Mesmaeker
  • Patent number: 8680337
    Abstract: The present invention relates to a process for the preparation of compounds of formula I wherein R1 and R2 are each independently of the other hydrogen or C1-C5alkyl and R3 is CF3 or CF2H, by a) reaction of a compound of formula II wherein R1 and R2 are as defined for formula I, with at least one reducing agent to form a compound of formula III wherein R1 and R2 are as defined for formula I, and b) reaction of that compound with at least one reducing agent to form a compound of formula IV wherein R1 and R2 are as defined for formula I, and (c) reaction of that compound with a compound of formula V wherein Q is chlorine, fluorine, bromine, iodine, hydroxy or C1-C6alkoxy and R3 is as defined for formula I, to form the compound of formula I; and to novel intermediates for use in that process.
    Type: Grant
    Filed: May 7, 2013
    Date of Patent: March 25, 2014
    Assignee: Sungenta Limited
    Inventors: Hans Tobler, Harald Walter, Josef Ehrenfreund, Camilla Corsi, Fanny Giordano, Martin Zeller, Gottfried Seifert, Shailesh Shah, Neil George, Ian Jones, Paul Bonnett
  • Publication number: 20130253225
    Abstract: The present invention relates to a process for the preparation of compounds of formula I wherein R1 and R2 are each independently of the other hydrogen or C1-C5alkyl and R3 is CF3 or CF2H, by a) reaction of a compound of formula II wherein R1 and R2 are as defined for formula I, with at least one reducing agent to form a compound of formula III wherein R1 and R2 are as defined for formula I, and b) reaction of that compound with at least one reducing agent to form a compound of formula IV wherein R1 and R2 are as defined for formula I, and (c) reaction of that compound with a compound of formula V wherein Q is chlorine, fluorine, bromine, iodine, hydroxy or C1-C6alkoxy and R3 is as defined for formula I, to form the compound of formula I; and to novel intermediates for use in that process.
    Type: Application
    Filed: May 7, 2013
    Publication date: September 26, 2013
    Applicants: SYNGENTA LIMITED, SYNGENTA CROP PROTECTION, LLC
    Inventors: Hans Tobler, Harald Walter, Josef Ehrenfreund, Camilla Corsi, Fanny Giordano, Martin Zeller, Gottfried Seifert, Shailesh Shah, Neil George, Ian Jones, Paul Bonnett
  • Patent number: 8207207
    Abstract: The invention relates to a fungicidally active compound of formula (I): as defined in claim 1; to the preparation of these compounds, to novel intermediates used in the preparation of these compounds, to agrochemical compositions which comprise at least one of the novel compounds as active ingredient, to the preparation of the compositions mentioned and to the use of the active ingredients or compositions in agriculture or horticulture for controlling or preventing infestation of plants by phytopathogenic microorganisms, preferably fungi.
    Type: Grant
    Filed: April 23, 2010
    Date of Patent: June 26, 2012
    Assignee: Syngenta Crop Protection LLC
    Inventors: Hans Tobler, Harald Walter, Josef Ehrenfreund, Camilla Corsi
  • Patent number: 8183416
    Abstract: The invention relates to a fungicidally active compound of formula (I): where Het is a 5- or 6-membered heterocyclic ring containing one to three heteroatoms, each independently selected from oxygen, nitrogen and sulphur, the ring being substituted by the groups R6, R7 and R8; R1 is hydrogen, C1-4 alkyl, C1-4 haloalkyl, C1-4alkoxy, C1-4haloalkoxy, CH2C?CR9, CH2CR10?CHR11, CH?C?CH2 or COR12; R2 and R3 are each, independently, hydrogen, halo, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl or C1-4 haloalkoxy; R4 and R5 are each independently selected from halo, cyano and nitro; or one of R4 and R5 is hydrogen and the other is selected from halo, cyano and nitro; R6, R7 and R8 are each, independently, hydrogen, halo, cyano, nitro, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy(C1-4)alkyl, C1-4haloalkoxy(C1-4)alkyl or C1-4haloalkoxy, provided that at least one of R6, R7 and R8 is not hydrogen; R9, R10 and R11 are each, independently, hydrogen, halo, C1-4 alkyl, C1-4 haloalkyl or C1-4 alkoxy(C1-4)alkyl; and R12 is hydrogen,
    Type: Grant
    Filed: April 23, 2010
    Date of Patent: May 22, 2012
    Assignee: Syngenta Crop Protection, Inc.
    Inventors: Hans Tobler, Harald Walter, Josef Ehrenfreund, Camilla Corsi
  • Publication number: 20120059198
    Abstract: A molecular species is covalently attached to elemental carbon by exposing the carbon to a reaction mixture containing a strong base and a compound of the formula (I) or (II) in which X denotes a covalently attached atom or group capable of forming an X? anion and each Z is a moiety comprising a plurality of atoms, but which does not have a hydrogen atom directly attached to the atom which itself is directly attached to the —CH2X or —CHX group. The carbon substrate may be graphite or carbon nanotubes.
    Type: Application
    Filed: February 12, 2010
    Publication date: March 8, 2012
    Applicant: Schlumberger Technology Corporation
    Inventors: Fenglou Zou, Nathan lawrence, Timothy Jones
  • Publication number: 20110152563
    Abstract: Disclosed herein is a method for synthesizing terpenoid compounds, as well as compositions comprising terpenoids and methods for their use. In one aspect the process is represented by the scheme wherein G is X is and R1, R2 and R3 independently are selected from H, acyl, lower alkyl and aralkyl; and Y is —O—, —S— or —NH—, and R4 is selected from H, acyl, lower alkyl and aralkyl.
    Type: Application
    Filed: August 10, 2009
    Publication date: June 23, 2011
    Inventors: Joseph P. Noel, Justin A. Ramsey, Thomas J. Baiga
  • Publication number: 20110112275
    Abstract: The present invention relates to condensed aromatic compounds with multiple ring bridging of the general formulae (1), (2), (3), (4) and (5). The invention furthermore relates to the use of the compounds according to the invention in an organic electronic device and to a process for the preparation of the compounds according to the invention. The invention furthermore relates to an electronic device which comprises the compounds according to the invention.
    Type: Application
    Filed: October 1, 2009
    Publication date: May 12, 2011
    Applicant: Merck Patent GmbH
    Inventors: Amir Hossain Parham, Christof Pflumm, Holger Heil, Arne Buesing
  • Publication number: 20100204482
    Abstract: The invention relates to a fungicidally active compound of formula (I): where Het is a 5- or 6-membered heterocyclic ring containing one to three heteroatoms, each independently selected from oxygen, nitrogen and sulphur, the ring being substituted by the groups R6, R7 and R8; R1 is hydrogen, C1-4 alkyl, C1-4 haloalkyl, C1-4alkoxy, C1-4haloalkoxy, CH2C?CR9, CH2CR10?CHR11, CH?C?CH2 or COR12; R2 and R3 are each, independently, hydrogen, halo, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl or C1-4 haloalkoxy; R4 and R5 are each independently selected from halo, cyano and nitro; or one of R4 and R5 is hydrogen and the other is selected from halo, cyano and nitro; R6, R7 and R8 are each, independently, hydrogen, halo, cyano, nitro, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy(C1-4)alkyl, C1-4haloalkoxy(C1-4)alkyl or C1-4haloalkoxy, provided that at least one of R6, R7 and R8 is not hydrogen; R9, R10 and R11 are each, independently, hydrogen, halo, C1-4 alkyl, C1-4 haloalkyl or C1-4 alkoxy(C1-4)alkyl; and R12 is hydrogen,
    Type: Application
    Filed: April 23, 2010
    Publication date: August 12, 2010
    Applicant: SYNGENTA CROP PROTECTION, INC.
    Inventors: Hans Tobler, Harald Walter, Josef Ehrenfreund, Camilla Corsi
  • Patent number: 7732469
    Abstract: The invention relates to a fungicidally active compound of formula (I): where Het is a 5- or 6-membered heterocyclic ring containing one to three heteroatoms, each independently selected from oxygen, nitrogen and sulphur, the ring being substituted by the groups R6, R7 and R8; R1 is hydrogen, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy, CH2 C?CR9, CH2 CR10?CHR11, CH?C?CH2 or COR12; R2 and R3 are each, independently, hydrogen, halo, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl or C1-4 haloalkoxy; R4 and R5 are each independently selected from halo, cyano and nitro; or one of R4 and R5 is hydrogen and the other is selected from halo, cyano and nitro; R6, R7 and R8 are each, independently, hydrogen, halo, cyano, nitro, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy(C1-4)alkyl, C1-4 haloalkoxy(C1-4)alkyl or C1-4 haloalkoxy, provided that at least one of R6, R7 and R8 is not hydrogen; R9, R10 and R11 are each, independently, hydrogen, halo, C1-4 alkyl, C1-4 haloalkyl or C1-4 alkoxy(C1-4)alkyl; and R12 is hydrogen
    Type: Grant
    Filed: October 23, 2006
    Date of Patent: June 8, 2010
    Assignee: Syngenta Crop Protection, Inc.
    Inventors: Hans Tobler, Harald Walter, Josef Ehrenfreund, Camilla Corsi
  • Publication number: 20100056621
    Abstract: The present invention relates to agonists of the hTAS2R14 bitter taste receptor and its role in bitter taste transduction. The invention also relates to assays for screening molecules that modulate, e.g. suppress or block hTAS2R14 bitter taste transduction or bitter taste response.
    Type: Application
    Filed: April 20, 2005
    Publication date: March 4, 2010
    Applicant: Deutsches Institut fur Ernahrungsforschung
    Inventors: Maik Behrens, Anne Brockhoff, Bernd Bufe, Christina Kuhn, Wolfgang Meyerhof, Marcel Winnig
  • Publication number: 20090163569
    Abstract: The present invention relates to a process for the preparation of compounds of formula (I) wherein R1 and R2 are each independently of the other hydrogen or C1-C5alkyl and R3 is CF3 or CF2H, by a) reaction of a compound of formula (II) wherein R1 and R2 are as defined for formula (I), with at least one reducing agent to form a compound of formula (III) wherein R1 and R2 are as defined for formula (I), and b) reaction of that compound with at least one reducing agent to form a compound of formula (IV) wherein R1 and R2 are as defined for formula (I), and (c) reaction of that compound with a compound of formula (V) wherein Q is chlorine, fluorine, bromine, iodine, hydroxy or C1-C6alkoxy and R3 is as defined for formula (I), to form the compound of formula (I); and to novel intermediates for use in that process.
    Type: Application
    Filed: September 14, 2006
    Publication date: June 25, 2009
    Applicants: SYNGENTA CROP PROTECTION, INC., SYNGENTA LIMITED
    Inventors: Hans Tobler, Harald Walter, Josef Ehrenfreund, Camilla Corsi, Fanny Giordano, Martin Zeller, Gottfried Seifert, Shailesh Shah, Neil George, Ian Kevin Jones, Paul Edward Bonnett
  • Publication number: 20080227835
    Abstract: The invention relates to a fungicidally active compound of formula (I): where Het is a 5- or 6-membered heterocyclic ring containing one to three heteroatoms, each independently selected from oxygen, nitrogen and sulphur, the ring being substituted by the groups R6, R7 and R8; R1 is hydrogen, C1-4alkyl, C1-4haloalkyl, C1-4alkoxy, C1-4haloalkoxy, CH2C?CR9, CH2CR10?CHR11, CH?C?CH2 or COR12; R2 and R3 are each, independently, hydrogen, halo, C1-4alkyl, C1-4 alkoxy, C1-4 haloalkyl or C1-4haloalkoxy; R4 and R5 are each independently selected from halo, cyano and nitro; or one of R4 and R5 is hydrogen and the other is selected from halo, cyano and nitro; R6, R7 and R8 are each, independently, hydrogen, halo, cyano, nitro, C1-4alkyl, C1-4haloalkyl, C1-4 alkoxy(C1-4)alkyl, C1-4 haloalkoxy(C1-4)alkyl or C1-4 haloalkoxy, provided that at least one of R6, R7 and R8 is not hydrogen; R9, R10 and R11 are each, independently, hydrogen, halo, C1-4 alkyl, C1-4 haloalkyl or C1-4 alkoxy(C1-4)alkyl; and R12 is hydrogen, C1-6 alk
    Type: Application
    Filed: October 23, 2006
    Publication date: September 18, 2008
    Applicant: SYNGENTA CROP PROTECTION, INC.
    Inventors: Hans Tobler, Harald Walter, Josef Ehrenfreund, Camilla Corsi
  • Publication number: 20080167474
    Abstract: The present invention provides azulenyl nitrones, such as those having the following general formula: (I) compositions comprising the same and methods of their use for the treatment or prevention of oxidative, ischemic, ischemia/reperfusion-related and chemokine-mediated conditions.
    Type: Application
    Filed: September 22, 2005
    Publication date: July 10, 2008
    Applicant: FLORIDA INTERNATIONAL UNIVERSITY
    Inventors: David A. Becker, James J. Ley
  • Publication number: 20080145708
    Abstract: The present invention relates to the improvement of organic electroluminescent devices, in particular blue-emitting devices, by using compounds of the formula (1) as dopants in the emitting layer.
    Type: Application
    Filed: March 20, 2006
    Publication date: June 19, 2008
    Applicant: Merck Patent GmbH
    Inventors: Holger Heil, Philip Stoessel, Horst Vestweber, Rocco Fortte
  • Patent number: 7265251
    Abstract: A process for the nitration of conjugated alkenes of formula (I) wherein R, R1, R2, R3 and R4 have the meanings reported in the description, which allows to obtain the corresponding ?-nitro-alkenes, characterised in that the nitrating agent is a mixture of an inorganic nitrite and iodine in the presence of an oxidising agent is described.
    Type: Grant
    Filed: October 12, 2005
    Date of Patent: September 4, 2007
    Assignee: Zambon Group S.p.A.
    Inventors: Maurizio Paiocchi, Aldo Belli, Francesco Ponzini, Marco Villa
  • Patent number: 7211685
    Abstract: A compound of the formula [I] wherein R1 is optionally substituted aryl group or optionally substituted heteroaryl group; R2 is optionally substituted C1-6 alkyl group, C3-7 cycloalkyl group and the like; R3 is hydrogen atom, C1-6 alkyl group, hydroxyl group and the like; R4 is hydrogen atom, C1-6 alkyl group and the like; R5 and R6 are each C1-6 alkyl group and the like; R7 is optionally substituted aryl group or optionally substituted heteroaryl group; X1, X2 and X3 are each C1-6 alkylene group and the like; and X4 and X5 are each a single bond, methylene group and the like, a salt thereof, a solvate thereof or a prodrug thereof, and a pharmaceutical composition containing the compound, particularly a calcium receptor antagonist and a therapeutic agent for osteoporosis, are provided.
    Type: Grant
    Filed: November 12, 2004
    Date of Patent: May 1, 2007
    Assignee: Japan Tobacco Inc.
    Inventors: Yuko Shinagawa, Takeo Katsushima, Takashi Nakagawa
  • Patent number: 6943257
    Abstract: The present invention provides a process for preparing an aromatic bromide or aromatic iodide from an aromatic amine derivative using nitrite anion and halodimethylsulfonium 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 or nitrogen; R1, R2, R3, R4 and R5 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 R1, R2, R3, R4 and R5 may combine to form a ring.
    Type: Grant
    Filed: September 21, 2001
    Date of Patent: September 13, 2005
    Inventors: Woon Phil Baik, Jung Min Kim, Young Sam Kim, Cheol Hun Yoon, Shin Jong Kim, Seok Woo Lee
  • Publication number: 20040006235
    Abstract: In a process for the preparation of ring compounds via a combinatorial synthesis, the reaction procedure is based on a Suzuki coupling, subsequent halo-demetallation and finally a further Suzuki coupling. The Suzuki couplings are each carried out with a boronic acid or a boronic acid ester. The reaction procedure uses provides novel ring compounds and uses novel synthesis units used for this purpose. The novel ring compounds are suitable for use as constituents in liquid-crystalline mixtures.
    Type: Application
    Filed: March 17, 2003
    Publication date: January 8, 2004
    Applicant: Merck Patent GmbH
    Inventors: Detlef Pauluth, Peer Kirsch, Peter Baeuerle, Oliver Deeg
  • Patent number: 6403789
    Abstract: A halogenating agent of the formula (1) and a method of halogenating hydroxyl group wherein R1 and R2 are the same or different and are each ethyl, propyl, isopropyl, butyl, isobutyl or allyl; X is chlorine atom or bromine atom; and Y is chlorine ion, bromine ion, dichlorophosphate ion, dibromophosphate ion, chlorosulfonate ion, bromosulfonate ion, chlorooxalate ion or bromooxalate ion.
    Type: Grant
    Filed: September 26, 2000
    Date of Patent: June 11, 2002
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Daisuke Suzuki, Ryo Kikuchi, Masaru Yasui
  • Patent number: 6362381
    Abstract: Aromatic hydrocarbons are nitrated by a process in which the aromatic hydrocarbon is reacted in the liquid phase with an oxide of nitrogen selected from NO, N2O3, NO2 and N2O4 and with an oxygen-containing gas stream in the presence of a heterogeneous oxidic catalyst, wherein at least 0.1 mol %, based on the aromatic hydrocarbon, of water is present at the beginning of the reaction.
    Type: Grant
    Filed: September 6, 2001
    Date of Patent: March 26, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Eiermann, Klaus Ebel
  • Patent number: 6271411
    Abstract: A process is disclosed for preparing 2-aryl-substituted indenes by reacting an indene with an arene compound substituted with an halogen atom, preferably a iodine atom, or with an organosulphonate group, said reaction being carried out in a basic medium in the presence of a palladium catalyst. The compounds obtainable by this process can be used to prepare metallocene compounds with transition metals such as titanium, zirconium or hafnium, which are useful as catalyst components in the polymerization of olefins.
    Type: Grant
    Filed: December 11, 1998
    Date of Patent: August 7, 2001
    Assignee: Montell Technology Company bv
    Inventors: Ilya E. Nifant'ev, Yuri A. Dubitsky, Alexander A. Sitnikov
  • Patent number: 6242657
    Abstract: In the reaction of aromatic compounds with nitrating acids comprising HNO3 and, if appropriate, H2SO4 and/or H2O and/or H3PO4 to form aromatic nitro compounds, according to the invention an amount of from 0.5 to 20,000 ppm of one or more surface-active substances from the group of the anionic, cationic, zwitterionic or nonionic surface-active substances is added to the reaction mixture.
    Type: Grant
    Filed: April 26, 2000
    Date of Patent: June 5, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd-Michael König, Johannes Dühr, Hans-Joachim Raatz, Manfred Kaczorowski
  • Patent number: 6197825
    Abstract: The present invention relates to chromotropic nitrone spin trapping agents, methods of making these agents, compositions comprising same, and methods of their use. In particular, azulenyl nitrones of the present invention are effective agents for trapping free radical species and find use as efficient antioxidants in physicochemical and biological systems. Accordingly, the invention also relates to spin adducts formed from the combination of azulenyl nitrones with free radicals. The compounds of the present invention are readily prepared from available starting materials and find further use in assays and in a number of diagnostic, prophylactic and therapeutic applications, including but not limited to the alleviation, modulation and inhibition of the negative effects of carbon-centered or oxygen-centered radical species and other products of oxidation. Moreover, the combination adducts may be calorimetrically detected and, optionally, isolated and characterized to obtain valuable information (e.g.
    Type: Grant
    Filed: May 28, 1998
    Date of Patent: March 6, 2001
    Assignee: Florida International University
    Inventor: David Alan Becker
  • Patent number: 6194567
    Abstract: A halogenating agent of the formula (1) and a method of halogenating hydroxyl group wherein R1 and R2 are the same or different and are each ethyl, propyl, isopropyl, butyl, isobutyl or allyl; X is chlorine atom or bromine atom; and Y is chlorine ion, bromine ion, dichlorophosphate ion, dibromophosphate ion, chlorosulfonate ion, bromosulfonate ion, chlorooxalate ion or bromooxalate ion.
    Type: Grant
    Filed: October 13, 1999
    Date of Patent: February 27, 2001
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Daisuke Suzuki, Ryo Kikuchi, Masaru Yasui
  • Patent number: 5886242
    Abstract: The invention relates to chiral compounds containing at least one divalent or polyvalent chiral group, at least one polymerizable group, at least one spacer and at least one mesogenic group, and to their use as polymerizable, chiral dopes for the preparation of cholesteric networks.The novel compounds are suitable for use in electro-optical displays or as chiral dopes for nematic or cholesteric liquid crystals in order to produce layers which reflect in colors.
    Type: Grant
    Filed: January 12, 1998
    Date of Patent: March 23, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Karl-Heinz Etzbach, Paul Delavier, Karl Siemensmeyer, Gerhard Wagenblast, Lothar Laupichler, Volkmar Vill
  • Patent number: 5728901
    Abstract: A process for preparing a nitrated arene which comprises reacting an arene and nitric acid in the presence of a water tolerant Lewis acid catalyst under process conditions sufficient to form the nitrated arene and recovering the nitrated arene. Suitable Lewis acid catalysts are represented by the formula M.sup.n (A.sub.1).sub.x (A.sub.2).sub.n-x whereinM is selected from the group consisting of La, Pr, Nd, Sm, Eu, Gd, Dy, Ho, Er, Tm, Yb, Sc, Hf, Lu and Li;A.sub.1 and A.sub.2 are independently selected from a perfluoroalkylsulfonate, a fluorosulfonate, a hexafluorophosphate or a nitrate;n is the common oxidation state of M andx is 1, 2, 3 or 4 with the proviso that x is never greater than n.The catalysts of the process are isolatable from water and can be recycled for subsequent process cycles.
    Type: Grant
    Filed: October 4, 1996
    Date of Patent: March 17, 1998
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Dorai Ramprasad, Francis Joseph Waller, Anthony Gerard Barrett, David Christopher Braddock
  • Patent number: 5430157
    Abstract: A series of tetrahydrophenanthrenes are useful as inhibitors of 5.alpha.-reductase.
    Type: Grant
    Filed: December 13, 1993
    Date of Patent: July 4, 1995
    Assignee: Eli Lilly and Company
    Inventor: James E. Audia
  • Patent number: 5313009
    Abstract: A continuous process to nitrate a nitratable aromatic compound in a nitronium ion solution in a nitrator. The process comprises feeding into the nitrator nitronium ion solution of a composition within an area defined by connecting three points in a ternary phase diagram of nitric acid, sulfuric acid and water. The three points correspond to first about 82% of sulfuric acid and 18% nitric acid, secondly about 55% sulfuric acid and about 45% water and, thirdly, 100% sulfuric acid, with the nitric acid preferably being below about 3%. The nitratable aromatic compound is introduced in a manner such that a fine emulsion of hydrocarbon in the nitronium ion solution is formed with the hydrocarbon evenly distributed in the acid phase. The acid and the nitratable aromatic compound are brought into intimate contact in a plug-flow nitrator that contains mixing elements.
    Type: Grant
    Filed: October 14, 1993
    Date of Patent: May 17, 1994
    Assignee: NRM International Technologies C.V.
    Inventors: Alfred A. Guenkel, John M. Rae, Edward G. Hauptmann
  • Patent number: 5237077
    Abstract: The present invention relates to a process for producing an aromatic nitro compound by introducing a nitrogen oxide gas and ozone-containing oxygen or air into a halogenated organic solvent dissolving or suspending therein an aromatic compound, thereby subjecting the aromatic compound to nitration. By the use of a system comprising the nitrogen oxide and ozone-containing oxygen or air as the nitrating agent, the aromatic nitro compound can be produced under mild conditions without using any mineral acid. In addition, the various disadvantages due to the use of mineral acid in the conventional process can be avoided by the process of the present invention.
    Type: Grant
    Filed: March 27, 1992
    Date of Patent: August 17, 1993
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Hitomi Suzuki, Takashi Murashima, Kenkichi Tsukamoto
  • Patent number: 5212301
    Abstract: Introduction of a fluoro substituent into an aromatic ring adjacent an electron donating group is difficult producing mixed isomers and low yields of desired products.A process for the introduction of a fluoro substituent into a substantially adjacent position to an electron-donating group into an aromatic compound in high yield is disclosed.The fluoroaromatic compounds are useful as synthetic intermediates for example in the manufacture of agrochemicals, pharmaceuticals and dyestuffs.
    Type: Grant
    Filed: May 8, 1992
    Date of Patent: May 18, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: John S. Moilliet, Richard D. Chambers, Michael H. Rock
  • Patent number: 5210339
    Abstract: An improved process for the nitration of a substituted or unsubstituted benzocyclobutene compound in a reaction mixture comprising a nitrating agent, an unhalogenated carboxylic acid anhydride, clay and a solvent to produce a corresponding nitrobenzocyclobutene compound, is that wherein:(a) the solvent has a density above that of the nitrating agent or an extractable precursor thereof;(b) the reaction mixture is heated at a temperature such that solvent is removed from the reaction mixture to a site outside the reaction mixture to extract nitrating agent or extractable precursor thereof; and(c) the thus-extracted nitrating agent or precursor thereof is fed into the reaction mixture to nitrate the benzocyclobutene compound.
    Type: Grant
    Filed: April 15, 1992
    Date of Patent: May 11, 1993
    Assignee: The Dow Chemical Company
    Inventors: P. J. Thomas, R. Garth Pews
  • Patent number: 4973770
    Abstract: Process for the mononitration of a nitratable organic compound, such as benzene, with a mixed acid in which one of the reactants is delivered into a body of the other reactant in the form of ultra-fine droplets through an atomizing nozzle or similar orifice. The process is economic to construct and operate, is safe and simple to control and leads to a low cost, substantially pure product.
    Type: Grant
    Filed: December 15, 1988
    Date of Patent: November 27, 1990
    Assignee: C-I-L, Inc.
    Inventor: Colin M. Evans
  • 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: 4853151
    Abstract: Dispirotetradecanes of the formula I ##STR1## wherein R.sup.1 and R.sup.2 are each independently of each other alkyl containing 1 to 12 carbon atoms wherein one or more non-adjacent CH.sub.2 groups may also be replaced by --O--, --CO--, --CO--O--, --O--CO--, --O--COO-- and/or --CH.dbd.CH-- (trans), one of the radicals R.sup.1 and R.sup.2 also being H, F, Cl, Br, I, CN, NO.sub.2, NCS,A.sup.1 and A.sup.2 are each independently of each other trans-1,4-cyclohexylene wherein one or two non-adjacent CH.sub.2 groups may be replaced by --O-- and/or --S--, or 1,4-phenylene wherein one or more CH groups may also be replaced by N, with it also being possible optionally for A.sup.1 and A.sup.2 to be substituted laterally or axially by F, Cl, CN, CH.sub.3,Z.sup.1 and Z.sup.2 are each independently of each other --C--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 -- or a single bond,m and n are each 0, 1 or 2,(m+n) 0, 1 or 2,X.sup.1, X.sup.2, X.sup.3 and X.sup.
    Type: Grant
    Filed: August 11, 1987
    Date of Patent: August 1, 1989
    Assignee: Merck Patent Gesellschaft Mit Beschrankfter Haftung
    Inventors: Fritz Vogtle, Wolfgang Calaminus
  • Patent number: 4755276
    Abstract: A nitro-substituted pitch demonstrates softening point temperatures in the range of 75.degree.-250.degree. C. and a coking value of at least about 40%. Such pitch is produced by reacting a tar with a nitrating agent at a temperature below 150.degree. C. and above about 0.degree. C.
    Type: Grant
    Filed: November 17, 1986
    Date of Patent: July 5, 1988
    Assignee: Union Carbide Corporation
    Inventor: Irwin C. Lewis
  • Patent number: 4570011
    Abstract: The invention is a process for the preparation of an aromatic hydrocarbon with a cyclobutene ring fused to the aromatic hydrocarbon which comprises, dissolving an ortho alkyl halomethyl aromatic hydrocarbon in an inert solvent and pyrolyzing the solution of ortho alkyl halomethyl aromatic hydrocarbon in the inert solvent under conditions such that the ortho alkyl and halomethyl substituents form a cyclobutene ring thereby forming an aromatic hydrocarbon having a fused cyclobutene ring.
    Type: Grant
    Filed: May 21, 1984
    Date of Patent: February 11, 1986
    Assignee: The Dow Chemical Company
    Inventor: Ying-Hung So
  • Patent number: 4495372
    Abstract: A process for mon-nitrating a plynuclear aromatic compound essentially in the absence of sulfuric acid and a solvent comprising adding nitric acid to a liquid aromatic compound wherein the molar ratio of nitric acid to the aromatic compound in from 0.75/1 ot 2/1 and the reaction temperature is from 50.degree. to 100.degree. C.
    Type: Grant
    Filed: November 5, 1982
    Date of Patent: January 22, 1985
    Assignee: Uniroyal, Inc.
    Inventor: Joseph A. Feiccabrino
  • Patent number: 4447662
    Abstract: Aromatic hydrocarbons are nitrated by reacting the aromatic hydrocarbon in a nitrogen tetroxide-containing liquid reaction medium, in the presence of a beta-dicarbonyl compound having a "W" configuration with a carbonyl group at each apex of the "W", preferably at a pressure and temperature sufficient to maintain the nitrogen tetroxide in the liquid state. Addition of an inert organic co-solvent to the liquid nitrogen tetroxide for the metal acetylacetonate promoted nitration of benzene essentially eliminates the production of dinitrobenzenes.
    Type: Grant
    Filed: June 10, 1982
    Date of Patent: May 8, 1984
    Assignee: Air Products and Chemicals, Inc.
    Inventors: David S. Ross, Robert M. Johnson, Jr., Ripudaman Malhotra
  • Patent number: 4415744
    Abstract: Aromatic compounds are nitrated in the vapor phase via a process comprising contacting the aromatic compound with a nitrating agent in the presence of a nitration promotion catalyst which comprises the adduct of:(a) an alumina-silica-metal oxide combination represented by the formula:(Al.sub.2 O.sub.3).sub.a (SiO.sub.2).sub.b (M.sub.2/n O).sub.cwherein M is a metal cation selected from the group consisting of the lanthanides or rare earths, Groups 1b, 2b, 5b, 6b, 7b, and 8 of the Periodic Table of the Elements, and mixtures thereof, and a, b, and c represent weight percent of the Al.sub.2 O.sub.3, SiO.sub.2, and M.sub.2/n O components, respectively, in the alumina-silica-metal oxide combination, with a being 0 to 100, b being 0 to 100, and c being 0 to 50, and n represents an integer from 1 to 7 of the valence of the metal cation, with the proviso that the sum of (a+b) must be greater than 0, and(b) a catalytically effective amount of sulfur trioxide.
    Type: Grant
    Filed: October 21, 1981
    Date of Patent: November 15, 1983
    Assignee: Monsanto Company
    Inventors: Ignatius Schumacher, Kang-Bo Wang
  • Patent number: 4386007
    Abstract: Liquid crystalline naphthalene derivatives of the formula ##STR1## wherein ring A is 1,4-phenylene, trans-1,4-cyclohexylene or 1,4-cyclohex-1-enylene and ring system BC is 2,6-naphthylene, 3,4-dihydro-2,6-naphthylene or 1,2,3,4-tetrahydro-2,6-naphthylene, with the proviso that A is not 1,4-phenylene when BC is 2,6-naphthylene; and R.sub.1 and R.sub.2, which are identical or different, are each alkyl of up to 8 C atoms or, when the rings to which they are bonded are aromatic, also can be alkoxy, alkanoyloxy or alkoxycarbonyloxy having up to 8 C atoms in each case; or one of R.sub.1 and R.sub.2 also can be CN, halogen, CF.sub.3 or NO.sub.2 are valuable components for liquid crystalline dielectrics.
    Type: Grant
    Filed: December 5, 1980
    Date of Patent: May 31, 1983
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Joachim Krause, Michael Romer, Ludwig Pohl
  • Patent number: 4374293
    Abstract: Allylbenzene is converted to indene by means of a tungsten-containing catalyst.
    Type: Grant
    Filed: August 14, 1981
    Date of Patent: February 15, 1983
    Assignee: The Standard Oil Co.
    Inventors: J. D. Burrington, R. K. Grasselli, C. T. Kartisek
  • Patent number: 4335055
    Abstract: Compounds of the formula I ##STR1## in which Z, Z.sub.1, R, m and p are as defined in patent claim 1, can be obtained in a simple and economical manner by a novel process wherein a halide of the formula II ##STR2## is reacted with a substituted or unsubstituted vinylbenzene or vinylnaphthalene derivative in the presence of a base and of certain palladium catalysts, such as palladium acetate. The compounds (I) or functional derivatives preparable therefrom are useful, for example, for the preparation of known dyes or fluorescent brighteners, or can be used directly as fluorescent brighteners or as scintillators.
    Type: Grant
    Filed: May 8, 1981
    Date of Patent: June 15, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans-Ulrich Blaser, Dieter Reinehr, Alwyn Spencer
  • Patent number: 4331613
    Abstract: A process for the preparation of an optionally substituted trifluoromethyl-naphthalene which comprises contacting a compound of the formula ##STR1## in which R.sup.1 denotes hydrogen, alkyl, aralkyl, aryl, aryloxy, arylthio, polyhalogenoalkoxy, polyhalogenoalkylthio, halogen, nitro, halogenocarbonyl, halogenosulphonyl, alkylsulphonyl or arylsulphonyl, it being possible for the aromatic nuclei contained in the substituents R.sup.1 to be in turn substituted by halogen, alkyl, polyhalogenoalkoxy or polyhalogenoalkylthio,R.sup.2 represents hydrogen, halogen or alkyl andR.sup.3, R.sup.4, R.sup.5 and R.sup.6 denote hydrogen, orR.sup.3 and R.sup.4 or R.sup.4 and R.sup.5 in each case together denote a fused-on aromatic ring, and wherein, in the case where R.sup.3 and R.sup.4 together form a fused-on aromatic ring,R.sup.5 and R.sup.6 independently of one another can also denote, in addition to hydrogen, halogen, nitro, halogenocarbonyl or halogenosulphonyl, and wherein, in the case where R.sup.4 and R.sup.
    Type: Grant
    Filed: June 23, 1980
    Date of Patent: May 25, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albrecht Marhold, Erich Klauke
  • Patent number: 4252739
    Abstract: This invention provides a convenient and commercially adaptable process for the preparation of vinylcyclopropane derivatives in high yields. The process involves reacting an alkylating agent and an activated methylene compound in the presence of an onium compound, an alkali metal compound and water, which while only necessary in trace amounts can be present in substantial quantities.
    Type: Grant
    Filed: August 20, 1979
    Date of Patent: February 24, 1981
    Assignee: Emery Industries, Inc.
    Inventors: Richard G. Fayter, Jr., John F. White, Eugene G. Harris
  • Patent number: 4241229
    Abstract: The wash liquor resulting from the nitration of aromatic compounds is contacted with a quantity of the same aromatic compound being nitrated and the resultant solution is recycled to the nitration process.
    Type: Grant
    Filed: August 8, 1979
    Date of Patent: December 23, 1980
    Assignee: American Cyanamid Company
    Inventor: Verner Alexanderson
  • Patent number: 4234470
    Abstract: A process for the continuous catalytic vapor-phase mononitration of aromatic compounds, especially benzene, using as the catalyst an .alpha.-fluorosulfonic acid polymer admixed with a complement inert to the nitration reaction and dimensionally stable under the reaction conditions.
    Type: Grant
    Filed: April 23, 1979
    Date of Patent: November 18, 1980
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Frederick R. Lawrence
  • Patent number: 4207266
    Abstract: This invention relates to a novel process for the direct trifluoromethylation of aromatic compounds via carbon tetrachloride and hydrogen fluoride in the presence of strong Bronsted or Lewis acids which give an acidic reaction (increase in concentration of H.sub.2 F.sup.+ ions) in anhydrous hydrogen fluoride.
    Type: Grant
    Filed: March 9, 1979
    Date of Patent: June 10, 1980
    Assignee: Rohm and Haas Company
    Inventor: Thomas R. Opie