Processes Patents (Class 546/327)
  • Patent number: 10259789
    Abstract: 4-Alkoxy-3-hydroxypicolinic acids may be conveniently prepared from 4,6-dibromo-3-hydroxypicolinonitrile in a series of chemical steps selected from bromo substitution, nitrile hydrolysis and halogen reduction that are conducted as a single pot process. 4,6-Dibromo-3-hydroxypicolinonitrile may be prepared from furfural in a series of chemical steps selected from cyano-amination, amine salt formation and bromination-rearrangement. 4-Alkoxy-3-acetoxypicolinic acids may be conveniently prepared from 4-alkoxy-3-hydroxypicolinic acids by treatment with acetic anhydride.
    Type: Grant
    Filed: January 23, 2017
    Date of Patent: April 16, 2019
    Inventors: Gregory T. Whiteker, Peter Borromeo, Fangzheng Li, Gary Roth
  • Patent number: 9884307
    Abstract: The invention solves the problem of the development of microporous layered MOF-type manganese materials based on isonicotinate anions, their synthesis and modification with selected ionic substances and application associated with the adsorption of the molecules and the construction of solid superionic conductors.
    Type: Grant
    Filed: September 2, 2014
    Date of Patent: February 6, 2018
    Assignee: Uniwersytet Jagiellonski
    Inventor: Dariusz Matoga
  • Publication number: 20150141654
    Abstract: Methods of preparing a fluorinated substrate by combining potassium fluoride, a quaternary ammonium salt, and a substrate substituted with at least one chloro, bromo, sulfonyl, or nitro group to thereby provide the fluorinated substrate are disclosed.
    Type: Application
    Filed: November 12, 2014
    Publication date: May 21, 2015
    Inventors: Laura Allen, Melanie Sanford, Shin Hee Lee, Douglas Bland, Yang Cheng, Gary Roth, Joseck M. Muhuhi
  • Publication number: 20150133673
    Abstract: Methods of preparing a fluorinated substrate by combining potassium fluoride, imidazolium salt, and a substrate substituted with at least one chloro, bromo, sulfonyl, or nitro group to thereby provide the fluorinated substrate are disclosed.
    Type: Application
    Filed: November 12, 2014
    Publication date: May 14, 2015
    Inventors: Melanie Sanford, Shin H. Lee, Laura Allen
  • Publication number: 20150133672
    Abstract: Methods of preparing a fluorinated aryl or heteroaryl substrate by combining a quaternary ammonium cyanide and an aryl or heteroaryl substrate substituted with at least one chloro, bromo, sulfonyl, or nitro group to thereby provide a mixture, and combining the mixture with hexafluorobenzene to thereby provide the fluorinated substrate.
    Type: Application
    Filed: November 12, 2014
    Publication date: May 14, 2015
    Inventors: Laura Allen, Melanie Sanford, Douglas Bland
  • Patent number: 8889877
    Abstract: The present invention relates to the preparation of pyridinone carboxylic acid aldehydes such as 5-methoxy-6-(methoxycarbonyl)-4-oxo-1-(2-oxoethyl)-1,4-dihydropyridine-3-carboxylic acid.
    Type: Grant
    Filed: March 22, 2011
    Date of Patent: November 18, 2014
    Assignee: VIIV Healthcare Company
    Inventors: Steven N. Goodman, Matthew David Kowalski, Douglas Matthew Mans, Huan Wang
  • Publication number: 20140031558
    Abstract: Provided herein are fluoropicolinoyl fluorides and processes for their preparation. In some embodiments, provided herein is a process for the preparation of 5-fluoro-6-aryl-picolinoyl fluorides from chloropicolinoyl chlorides.
    Type: Application
    Filed: July 23, 2013
    Publication date: January 30, 2014
    Applicant: Dow AgroSciences LLC
    Inventors: James M. Renga, Yang Cheng, Joseck M. Muhuhi, David E. Podhorez, Gary A. Roth, Scott P. West, Gregory T. Whiteker, Yuanming Zhu
  • Patent number: 8580967
    Abstract: The present invention features compounds that are prodrugs of HIV integrase inhibitors and therefore are useful in the delivery of compounds for the inhibition of HIV replication, the prevention and/or treatment of infection by HIV, and in the treatment of AIDS and/or ARC. For example, the present invention includes methyl 3-(benzyloxy)-1-(2,2-dihydroxyethyl)-4-oxo-1,4-dihydropyridine-2 -carboxylate of the formula P-8: and processes for the preparation thereof.
    Type: Grant
    Filed: July 23, 2009
    Date of Patent: November 12, 2013
    Assignees: Shionogi & Co., Ltd., VIIV Healthcare Company
    Inventors: Brian Alvin Johns, Jason Gordon Weatherhead, Toshikazu Hakogi, Yasunori Aoyama
  • Publication number: 20120088918
    Abstract: The invention relates to a continuous method for producing aromatic carboxylic acid esters by reacting at least one aromatic carboxylic acid of formula (I) Ar—COOH (I), wherein Ar represents an optionally substituted aryl group with 5 to 50 atoms, with at least one alcohol of formula (II) R2—(OH)n (II), wherein R2 represents an optionally substituted hydrocarbon group with 1 to 100 C atoms and n is an integer from 1 to 10, in the presence of at least one transesterification catalyst in a reaction tube, the longitudinal axis of which extends in the direction of propagation of the microwaves of a monomode microwave applicator, under microwave irradiation to form the ester.
    Type: Application
    Filed: June 9, 2010
    Publication date: April 12, 2012
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventors: Matthias Krull, Roman Morschhaeuser
  • Publication number: 20120065405
    Abstract: Disclosed herein cost effective and ecofriendly large scale process for producing pyridine carboxylic acid with high purity and yield at industrial scale.
    Type: Application
    Filed: September 12, 2011
    Publication date: March 15, 2012
    Applicant: JUBILANT LIFE SCIENCES LTD
    Inventors: Shailendra Kumar SINGH, Neeraj TIWARI, Ashutosh AGARWAL
  • Patent number: 8039633
    Abstract: To provide a method for producing a specific nicotinic acid derivative or a salt thereof. A method for producing a nicotinic acid derivative represented by the formula (I): wherein each of X1 and X2 which are independent of each other, is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a haloalkyl group or a haloalkoxy group; R is an alkyl group; and Hal is a chlorine atom or a bromine atom; or a salt thereof, is provided which comprises reacting a compound represented by the formula (II): is wherein X1, X2 and R are as defined above, or a salt thereof, with a halogenating agent.
    Type: Grant
    Filed: April 20, 2006
    Date of Patent: October 18, 2011
    Assignee: Ishihara Sangyo Kaisha, Ltd.
    Inventors: Shigeyuki Nishimura, Fumio Kanamori, Masashi Hisamoto
  • Publication number: 20110201817
    Abstract: Prodrugs of levodopa, methods of making prodrugs of levodopa, methods of using prodrugs of levodopa, and compositions of prodrugs of levodopa are disclosed.
    Type: Application
    Filed: April 27, 2011
    Publication date: August 18, 2011
    Applicant: XenoPort, Inc.
    Inventors: Jia-Ning XIANG, Mark A. Gallop, Cindy X. Zhou, Mark Nguyen, Xuedong Dai, Jianhua Li, Kenneth C. Cundy, Nelson L. Jumbe
  • Publication number: 20110178396
    Abstract: A compound comprising a pyridine carboxamide structure, for use in imaging or treating melanoma, is described. An aromatic ring in the structure is substituted with a radiohalogen atom and the substitution on the amide nitrogen atom is such that the compound binds to melanin.
    Type: Application
    Filed: April 22, 2009
    Publication date: July 21, 2011
    Applicant: CRC FOR BIOMEDICAL IMAGING DEVELOPMENT LTD.
    Inventors: Andrew Katsifis, Ivan Greguric
  • Publication number: 20100311968
    Abstract: Organic compounds having t-butyl ester or BOC carbonate protecting groups are effectively deprotected by heating in a fluorinated alcohol solution.
    Type: Application
    Filed: June 9, 2010
    Publication date: December 9, 2010
    Inventors: Jason Chi-Chung Choy, Saul Jaime-Figueroa
  • Publication number: 20100305330
    Abstract: A process for preparing 2-alkyl-3-halo-6-nitrilpyridine and its carboxylic acid and ester derivatives by reacting 2-alkyl-3-halo-pyridine N-oxide with dimethyl sulfate, followed by reacting the adduct with alkaline cyanide to obtain the target molecule is disclosed. Further treatment of the nitrile with base to obtain the corresponding acid, and esterification are described as well. The process was scaled up to multi-kilogram level that provided satisfactory output.
    Type: Application
    Filed: June 2, 2009
    Publication date: December 2, 2010
    Applicant: Synergetica Changzhou Chemical Company
    Inventors: Heng E. Michael Su, Yizu Wu, Chunming Wu, Haiyan Li, Lee Alan DeWitt
  • Publication number: 20100210837
    Abstract: This disclosure describes the molecular cloning of a pactamycin biosynthetic gene cluster from Streptomyces pactum ATCC 27456, characterization of individual genes in the gene cluster and the proteins encoded thereby as well as uses thereof. The pactamycin gene cluster is located within an 86.35 kilobases genetic locus and includes 53 open reading frames, 26 of which are considered to be the core cluster directly involved in the biosynthesis of pactamycin.
    Type: Application
    Filed: April 18, 2008
    Publication date: August 19, 2010
    Inventor: Taifo Mahmud
  • Patent number: 7745631
    Abstract: The invention discloses an improved process for producing an intermediate to produce large quantity of 2-(Phenyl methyl thio)-3-pyridine carboxylic acid. The process comprises reacting 2-chloro-3-cyanopyridine with benzyl mercaptan in presence of a base and an aprotic solvent. The resulting intermediate 2-(phenyl methyl thio)-3-cyanopyridine is hydrolyzed in presence of a base in an autoclave and isolated under acidic condition to get the desired product.
    Type: Grant
    Filed: June 17, 2004
    Date of Patent: June 29, 2010
    Assignee: Jubilant Organosys Limited
    Inventors: Shailendra Kumar Singh, Ashutosh Agarwal
  • Publication number: 20100160632
    Abstract: The present invention relates to zinc amide bases of the general formula (I) (R1R2N)2—Zn.aMgX12.bLiX2??(I) wherein R1 and R2 are each independently selected from substituted or unsubstituted, linear or branched alkyl, alkenyl, alkynyl or silyl derivatives thereof, and substituted or unsubstituted aryl or heteroaryl, and wherein R1 and R2 can form together a ring structure, or R1 and/or R2 can be part of a polymer structure; X12 is a divalent anion or two monovalent anions that are independent from each other; X2 is a monovalent anion; a is >0; and b is >0. The zinc amide bases can be used, amongst other things, for deprotonation and metallization of aromatics.
    Type: Application
    Filed: May 14, 2008
    Publication date: June 24, 2010
    Inventors: Paul Knochel, Stefan Wunderlich
  • Publication number: 20100137378
    Abstract: Compounds of formula (I) or a pharmaceutically acceptable derivative thereof: wherein X, Y, Z, R2a, R2b, R3a, R3b, R8, R9, and Rx are as defined in the specification, a process for the preparation of such compounds, pharmaceutical compositions comprising such compounds and the use of such compounds in medicine (EP, —receptor antagonists).
    Type: Application
    Filed: December 21, 2005
    Publication date: June 3, 2010
    Applicant: GLAXO GROUP LIMITED
    Inventors: Gerard Martin Paul Giblin, Adrian Hall, David Nigel Hurst, Derek Anthony Rawlings, Tiziana Scoccitti
  • Patent number: 7692020
    Abstract: The invention relates to a process for the preparation of pyridylcarboxylic amides and esters I, Formula (I) wherein Hal, X and R1 have the meanings given in claim 1, which comprises the following steps: (a) heating a mixture consisting essentially of trichloromethylpyridine II, Formula (II), wherein Hal has the meaning given, and 1.0 to 1.5 equivalents of concentrated sulfuric acid, characterized in that the trichloromethylpyridine II in a liquid form is added to the concentrated sulfuric acid at a temperature from 110° C. to 160° C.; and (b) reacting the intermediate product obtained in step (a) with an amine or alcohol III, HXR1, wherein X and R1 have the meaning given, optionally in the presence of a solvent and/or a base.
    Type: Grant
    Filed: October 26, 2006
    Date of Patent: April 6, 2010
    Assignee: BASF SE
    Inventors: Monika Brink, Marcus Knell, Jan Hendrik Wevers
  • Publication number: 20090143595
    Abstract: A process for the preparation of a multi-dimensional microporous metal-organic compound comprising the steps of providing a first reactant which includes at least one metal in ionic form, providing a second reactant which includes a bridging organic ligand, grinding the first and second reactants together, wholly or substantially in the absence of solvent.
    Type: Application
    Filed: August 25, 2006
    Publication date: June 4, 2009
    Applicant: The Queen's University of Belfast
    Inventors: Stuart Lloyd James, Ana Lazuen-Garay, Anne Pichon
  • Patent number: 7511149
    Abstract: Insecticidal sulfoximines are produced efficiently and in high yield by the oxidation of the corresponding sulfilimine with ruthenium tetraoxide or an alkali metal permanganate.
    Type: Grant
    Filed: February 9, 2007
    Date of Patent: March 31, 2009
    Assignee: Dow AgroSciences LLC
    Inventors: Kim E. Arndt, Douglas C. Bland, David E. Podhorez, James R. McConnell
  • Publication number: 20080306278
    Abstract: An improved process for preparing arylethanoldiamines is described. Compounds of this type are known to be useful as agonists at atypical beta-adrenoceptors (also known as beta-3-adrenoceptors).
    Type: Application
    Filed: August 12, 2008
    Publication date: December 11, 2008
    Applicant: SMITHKLINE BEECHAM CORPORATION
    Inventors: Jason William Beames Cooke, Bobby Neal Glover, Ronnie Maxwell Lawrence, Matthew Jude Sharp, Maria Fumiko Tymoschenko
  • Publication number: 20080227984
    Abstract: This invention relates to the selective oxidation of organic compounds. According to the invention organic compounds are selectively oxidized using a peracid or a source of peracid, a transition metal based heterogeneous catalysts and a borate or boric acid in the presence of water. Using the process of the present invention, both excellent conversion and product selectivity maybe obtained.
    Type: Application
    Filed: October 21, 2005
    Publication date: September 18, 2008
    Applicant: U.S. Borax, Inc.
    Inventors: Michael John Greenhill-Hooper, Robert Raja, John Meurig-Thomas
  • Publication number: 20080139817
    Abstract: The invention discloses an improved process for producing an intermediate to produce large quantity of 2-(Phenyl methyl thio)-3-pyridine carboxylic acid. The process comprises reacting 2-chloro-3-cyanopyridine with benzyl mercaptan in presence of a base and an aprotic solvent. The resulting intermediate 2-(phenyl methyl thio)-3-cyanopyridine is hydrolyzed in presence of a base in an autoclave and isolated under acidic condition to get the desired product.
    Type: Application
    Filed: June 17, 2004
    Publication date: June 12, 2008
    Inventors: Shailendra Kumar Singh, Ashutosh Agarwal
  • Patent number: 7371866
    Abstract: A process for catalytically oxidizing alkylaromatic compounds of the formula (I) Ar—CH2—R where Ar is an optionally substituted, aromatic or heteroaromatic 5-membered or 6-membered ring or a ring system having up to 20 carbon atoms where Ar may optionally be fused to a C1-C6-alkyl group in which up to 2 carbon atoms may be replaced by a heteroatom, and R is hydrogen, phenyl, benzyl or heteroaryl, where the phenyl, benzyl or heteroaryl radicals may also be joined to Ar by a bridge, or R together with Ar forms an optionally substituted ring system which may contain one or more optionally substituted heteroatoms, to the corresponding aromatic or heteroaromatic carboxylic acids in a solvent with ozone in the presence of a transition metal catalyst and optionally in the presence of an acid at a temperature between ?70° C. and 110° C. to the corresponding carboxylic acid.
    Type: Grant
    Filed: May 15, 2003
    Date of Patent: May 13, 2008
    Assignee: DSM Fine Chemicals Austria Nfg GmbH & Co KG
    Inventors: Walther Jary, Peter Poechlauer, Thorsten Ganglberger
  • 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: 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
  • Patent number: 6320053
    Abstract: The invention relates to a process for the preparation of hetero)aryloxyheteroarylcarboxylic amide or ester of formula VI wherein A1, A2, A3, A4, A5 Hal, X, R1, and R4 are defined within, which process comprises preparing the heteroarylcarboxylic amide or ester of formula I or a salt thereof,  from a trichoromethyl-heteroaromatic compound of formula II and reacting the compound of formula I with an aromatic or heteroaromatic hydroxyl compound of formula VII, R4—OH  VII optionally in the presence of a base.
    Type: Grant
    Filed: May 4, 2000
    Date of Patent: November 20, 2001
    Assignee: American Cyanamid Company
    Inventors: Marcus Knell, Monika Brink, Jan Hendrik Wevers, Willi Heinz
  • Patent number: 6204276
    Abstract: A germanium complex of germanium and an aromatic or nono-aromatic, carbocyclic or heterocyclic dicarboxylic acid, e.g. germanium bis(pyridine-2,6-dicarboxylate) has anti-infectious, interferon-inducing, and immunomodulating activity.
    Type: Grant
    Filed: March 5, 1999
    Date of Patent: March 20, 2001
    Assignee: Primamedic Ltd.
    Inventors: Vladimir Vsevolodovich Veselovsky, Leonid Leonidovich Danilov, Serguey Dmitrievich Maltsev, Alexander Vasilyevich Pronin, Alexander Naumovich Narovlyansky, Alexander Vladimirovich Sanin, Anna Valentinovna Deyeva, Aleftina Mikhailovna Amchenkova
  • Patent number: 6200933
    Abstract: An agricultural or horticultural fungicide containing 6-(unsubstituted or substituted) phenoxy picolinic acid represented by the general formula (I), as an effective ingredient. wherein R is a halogen atom, a C1 to C4 alkyl group, a C1 to C4 haloalkyl group, a C1 to C4 alkoxy group, a C1 to C4 haloalkoxy group, a C1 to C4 alkylthio group, a C1 to C4 alkylamino group, a di(C1 to C4 alkyl)amino group or a C7 to C8 aralkyl(C1 to C4 alkyl)amino group; n2 is an integer of 0 to 3; Y is a C1 to C4 alkyl group, a C1 to C4 haloalkyl group, a C1 to C4 alkoxy group, a C1 to C4 haloalkoxy group, a C1 to C4 alkylthio group, a C1 to C4 haloalkylthio group or a halogen atom; and m is an integer of 0 to 5, and when m and n2 are not less than 2, Rs and Ys may be the same or different, respectively. The compound is useful as an effective ingredient of agricultural or horticultural fungicides.
    Type: Grant
    Filed: August 9, 1999
    Date of Patent: March 13, 2001
    Assignee: Kureha Kagaku Kabushiki Kaisha
    Inventors: Hisashi Kanno, Yoichi Kanda, Kazuhiko Sunagawa, Takayoshi Eizuka
  • 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: 6169183
    Abstract: A process for preparing pyridinecarboxylic esters of the general formula: wherein R1 is hydrogen, a C1-6-alkyl group, a C1-4-alkoxycarbonyl group, a C1-4-alkoxymethyl group or a fluorinated C1-6-alkyl group, R2 is a C1-4-alkyl group and X is chlorine or bromine. The pyridinecarboxylic esters are obtained by reacing the corresponding 2,3-dihalopyridines with carbon monoxide and a C1-4-alkanol in the presence of a weak base and a complex of palladium with a bis(diphenylphosphine). Pyridinecarboxylic esters are intermediates for preparing herbicides and drugs against fibrotic diseases.
    Type: Grant
    Filed: January 27, 1999
    Date of Patent: January 2, 2001
    Assignee: Lonza, Ltd.
    Inventors: Yves Bessard, Gerhard Stucky, Jean-Paul Roduit
  • Patent number: 6136754
    Abstract: New pyridyl-thiazoles of the formula ##STR1## and new intermediates of the formulae ##STR2## in which all variables have the meaning given in the description.All compounds and their salts and acid adducts are suitable for the protection of plants against attack by undesirable microorganisms.
    Type: Grant
    Filed: January 13, 1999
    Date of Patent: October 24, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd Gallenkamp, Klaus Stenzel, Gerd Hanssler, Stefan Dutzmann, Heinz-Wilhelm Dehne
  • Patent number: 6103906
    Abstract: A process for the preparation of 2,6-pyridinedicarboxylic acid esters of the general formula: ##STR1## wherein R.sup.1 is a C.sub.1 -C.sub.6 -alkyl group, a C.sub.3 -C.sub.6 -cycloalkyl group, an aryl group or an arylalkyl group, and R.sup.2 and R.sup.3 independently of one another are hydrogen or chlorine and R.sup.4 is hydrogen, a C.sub.1 -C.sub.6 -alkyl group, a C.sub.1 -C.sub.6 -alkoxy group or fluorine. The 2,6-pyridinedicarboxylic acid esters are obtained by reaction of the corresponding halopyridines with carbon monoxide and an alcohol of the general formula:R.sup.1 --OH IIIwherein R.sup.1 has the abovementioned meaning, in the presence of a base and of a complex of palladium with a bis-diphenylphosphine. 2,6-Pyridinedicarboxylic acid esters are intermediates for the preparation of compounds having anti-inflammatory action.
    Type: Grant
    Filed: March 12, 1998
    Date of Patent: August 15, 2000
    Assignee: Lonza, Ltd.
    Inventors: Jean-Paul Roduit, Yves Bessard
  • Patent number: 6090824
    Abstract: Compounds of formula I ##STR1## wherein Q.sup.1, Q.sup.2, Q.sup.3, and Q.sup.4 have any of the meanings given in the specification, their N-oxides, and their pharmaceutically acceptable salts are nonpeptide antagonists Substance P and NKA, useful for the treatment of asthma, etc. Also disclosed are pharmaceutical compositions, processes for preparing the compounds of formula I and intermediates.
    Type: Grant
    Filed: November 14, 1996
    Date of Patent: July 18, 2000
    Assignee: Zeneca Limited
    Inventors: Peter R. Bernstein, Bruce T. Dembofsky
  • Patent number: 5925765
    Abstract: A process for preparing pyridinecarboxylic esters of the general formula: ##STR1## wherein R.sup.1 is hydrogen, a C.sub.1 -C.sub.6 -alkyl group, a C.sub.1 -C.sub.4 -alkoxycarbonyl group or a C.sub.1 -C.sub.4 -alkoxymethyl group, R.sup.2 is a C.sub.1 -C.sub.4 -alkyl group and X is chlorine or bromine. The pyridinecarboxylic esters are obtained by reacting the corresponding 2,3-dihalopyridines with carbon monoxide and a C.sub.1 -C.sub.4 -alkanol in the presence of a weak base and a complex of palladium with a bis(diphenylphosphine). Pyridinecarboxylic esters are intermediates for preparing herbicides and drugs against fibrotic diseases.
    Type: Grant
    Filed: July 15, 1997
    Date of Patent: July 20, 1999
    Assignee: Lonza AG
    Inventors: Yves Bessard, Gerhard Stucky, Jean-Paul Roduit
  • Patent number: 5728837
    Abstract: A method has been developed for preparing nicotinic acid with a yield of 82-86% mol, in which method there is no formation of harmful gas wastes and liquid wastes.The process is carried out by gas-phase single-step oxidation of .beta.-picoline with oxygen in the presence of water vapor and a catalyst on the base of oxides of vanadium and titanium, with or without additives, at a temperature of 250.degree.-290.degree. C. and mole ratios O.sub.2 :.beta.-picoline=15-40 and H.sub.2 O:.beta.-picoline=10-70.
    Type: Grant
    Filed: July 17, 1996
    Date of Patent: March 17, 1998
    Assignee: Institut Kataliza Imeni G.K. Boreskova Sibirskogo Otdelenia Rossiiskoi Akademii Nauk
    Inventors: Evgenia Moiseevna Alkaeva, Tamara Vitalievna Andrushkevich, Galina Alexeevna Zenkovets, Mikhail Grigorievich Makarenko
  • Patent number: 5708177
    Abstract: The invention relates to a process for the preparation of optically active ortho-substituted 4-aryl- or heteroaryl-1,4-dihydropyridines by oxidation and subsequent reduction from their opposite enantiomers.
    Type: Grant
    Filed: August 26, 1996
    Date of Patent: January 13, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventor: Alexander Straub
  • Patent number: 5700944
    Abstract: A process for the production of a pyridinecarboxylic acid by the air-oxidation of an alkylpyridine in a liquid phase, in which the conversion of the alkylpyridine is high, the yield of the pyridinecarboxylic acid is therefore high, the content of impurities in the product is decreased, and unreacted raw material and an oxidation intermediate can be recycled without the adverse effect of accumulation of the catalyst and bromine component, the process comprising oxidizing an alkylpyridine with an oxygen-containing gas in a solvent in the presence of a catalyst formed of a heavy metal salt and a bromine compound, the solvent being a lower aliphatic monocarboxylic acid having a water content of 2 to 15% by weight, or the process comprising the step of catalytically hydrogenating an oxidation reaction mixture or an isolated pyridinecarboxylic acid in the presence of a catalyst of a metal belonging to the group VIII of the periodic table.
    Type: Grant
    Filed: May 8, 1996
    Date of Patent: December 23, 1997
    Assignee: Mitsubishi Gas Chemical Company
    Inventors: Toshihiro Hashimoto, Kenichi Nakamura, Makoto Takagawa
  • Patent number: 5693819
    Abstract: A process is described for the selective mono-ortho-hydroxyalkylation of 4-substituted pyridine derivatives. In this case a nucleophilic hydroxyalkylation is carried out on the protonated pyridine derivative under the action of peroxodisulfate.
    Type: Grant
    Filed: December 27, 1993
    Date of Patent: December 2, 1997
    Assignee: Hoechst Atkiengesellschaft
    Inventor: Bernd Scharbert
  • Patent number: 5614636
    Abstract: A process for the preparation of carboxamides of nitrogen-containing aromatic heterocyclic compounds from the corresponding N-heterocyclic compounds by reaction thereof with formamide in the presence of peroxodisulfuric acid or a peroxodisulfate.
    Type: Grant
    Filed: May 27, 1994
    Date of Patent: March 25, 1997
    Assignee: Lonza Ltd.
    Inventors: Jean-Paul Roduit, Alain Wellig, Karin Amacker, Martin Eyer
  • Patent number: 5534635
    Abstract: It has been found that pyridine-2-carboxamides of the formula ##STR1## wherein R is amino or a residue convertible into amino, and pharmaceutically usable acid addition salts of that carboxamide in which R is amino can be prepared in a simple manner and in good yield by reacting 2,5-dichloropyridine in the presence of a palladium-phosphine catalyst with an alkyne of the formulaR.sup.1 --C.tbd.CH IIIwherein R.sup.1 is hydrogen, lower-alkyl, trimethylsilyl or the group --(R.sup.2)(R.sup.3)--COH and R.sup.2 and R.sup.3 each independently are hydrogen or lower-alkyl or together are cyclopentyl or cyclohexyl,oxidizing the resulting alkyne to give 5-chloropyridine-2-carboxylic acid and reacting this acid or a reactive functional derivative thereof with an amino compound of the formulaor with carbon monoxide and an amino compound of formula VI or with carbon monoxide and a lower alkanol which is optionally mixed with water and reacting the resulting acid or the resulting ester with an amino compound of formula VI.
    Type: Grant
    Filed: September 12, 1994
    Date of Patent: July 9, 1996
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michelangelo Scalone, Peter Vogt
  • Patent number: 5380861
    Abstract: It has been found that pyridine-2-carboxamides of the formula ##STR1## wherein R is amino or a residue convertible into amino, and pharmaceutically usable acid addition salts of that carboxamide in which R is amino can be prepared in a simple manner and in good yield by reacting 2,5-dichloropyridine in the presence of a palladium-phosphine catalyst with an alkyne of the formulaR.sup.1 -C.tbd.CH IIIwherein R.sup.1 is hydrogen, lower-alkyl, trimethylsilyl or the group --(R.sup.2)(R.sup.3)--COH and R.sup.2 and R.sup.3 each independently are hydrogen or lower-alkyl or together are cyclopentyl or cyclohexyl,oxidizing the resulting alkyne to give 5-chloropyridine-2-carboxylic acid and reacting this acid or a reactive functional derivative thereof with an amino compound of the formula VI. The compound of formula I in which R is amino is a known compound which is a reversible and highly active MAO-B inhibitor.
    Type: Grant
    Filed: May 25, 1993
    Date of Patent: January 10, 1995
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michelangelo Scalone, Peter Vogt
  • Patent number: 5166352
    Abstract: Pyridinecarboxylic acids and their acid chloride, aliphatic ester and alkylamide derivatives are prepared by passing vapors of a (trichloromethyl)pyridine compound, such as 2,3-dichloro-5-(trichloromethyl)pyridine over gamma-alumina at a temperature of about 250.degree. C. to 450.degree. C. to obtain a pyridinecarboxylic acid chloride compound, such as 2,3-dichloronicotinoyl chloride and, if desired, subsequently converting this compound to its acid, an ester, or an amide, such as 2,3-dichloronicotinic acid, methyl 2,3-dichloronicotinate, or N-methyl-2,3-dichloronicotinamide, by treatment with water, an aliphatic alcohol, or ammonia or an alkylamine, respectively.
    Type: Grant
    Filed: September 12, 1991
    Date of Patent: November 24, 1992
    Assignee: DowElanco
    Inventor: Clark P. Allphin
  • Patent number: 5155271
    Abstract: The invention relates to a process for the preparation of compounds of the formula ##STR1## in which Q is substituted or unsubstituted C.sub.1 -C.sub.6 alkyl, A is a direct bond or a bridging member, s is the number 1 or 2, Z is a radical of the formula --CH.sub.2 CH.sub.2 OH, --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --Y, and Y is a leaving group, and the benzene or napthalene nucleus I can be further substituted, which comprises reacting compounds of the formula ##STR2## with compounds of the formulaQ--OH (3)in which A, s, Z and Q are as defined under formula (1), in the presence of hydrogenation catalysts, and then carrying out further conversion reactions where appropriate.The compounds obtained by the process according to the invention are suitable as intermediates for the preparation of reactive dyes.
    Type: Grant
    Filed: June 25, 1990
    Date of Patent: October 13, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Aeschlimann
  • Patent number: 5081224
    Abstract: This invention relates to processes for producing an olefin-terminated polyester. In one of the processes which comprises reacting an olefin-terminated diester compound with a lactone in the presence of a polymerization catalyst with transesterification ability, the lactone is in a limited amount added to the reaction system. In another process which comprises reacting an olefin-terminated diester compound, a lactone compound, a cyclic acid anhydride and an epoxy compound in the presence of a polymerization catalyst with transesterification ability, the lactone, cyclic acid anhydride and epoxy compound are each in a limited amount added to the reaction system. In accordance with this invention, olefin-terminated polyesters having high terminal modification rates can be synthesized.
    Type: Grant
    Filed: October 12, 1990
    Date of Patent: January 14, 1992
    Assignee: Kanegafuchi Chemical Industry Co., Ltd.
    Inventors: Hiroshi Ando, Kazumasa Hashimoto, Jun Hattori, Kazuya Yonezawa
  • Patent number: 5008276
    Abstract: Fungicidal compounds of the formula (I): ##STR1## and stereoisomers thereof, wherein K is oxygen or sulphur; Z is optionally substituted aryl or optionally substituted heteroaryl; X is O, S(O).sub.n, NR.sup.4, CR.sup.1 R.sup.2, CHR.sup.5, CO, CR.sup.1 (OR.sup.2), C.dbd.CR.sup.1 R.sup.2, CHR.sup.1 CHR.sup.2, CR.sup.1 .dbd.CR.sup.2, CHR.sup.1 CR.sup.2 .dbd.CH, C.dbd.C, OCHR.sup.1, CHR.sup.1 O, OCHR.sup.1 O, S(O).sub.n CHR.sup.1, S(O).sub.n CHR.sup.1 O, CHR.sup.1 S(O).sub.n, CHR.sup.1 OSO.sub.2, NR.sup.4 CHR.sup.1, CHR.sup.1 NR.sup.4, CO.sub.2, O.sub.2 C, SO.sub.2 O, OSO.sub.2, CO.CO, COCHR.sup.1, COCHR.sup.1 O, CHR.sup.1 CO, CHOH.CHR.sup.1, CHR.sup.1.CHOH, ##STR2## CONR.sup.4, OCONR.sup.4, NR.sup.4 CO, CSNR.sup.4, OCS.NR.sup.4, SCO.NR.sup.4, NR.sup.4 CO.sub.2, NR.sup.4 CS, NR.sup.4 CSO, NR.sup.4 COS, NR.sup.4 CONR.sup.4, S(O).sub.n NR.sup.4, NR.sup.4 S(O).sub.n, CS.sub.2, S.sub.2 C, CO.S, SCO, N.dbd.N, N.dbd.CR.sup.1, CR.sup.1 .dbd.N, CHR.sup.1 CHR.sup.2 CH(OH), CHR.sup.1 OCO, CHR.sup.1 SCO, CHR.sup.1 NR.sup.
    Type: Grant
    Filed: October 17, 1988
    Date of Patent: April 16, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Christopher R. A. Godfrey, Stephen P. Heaney, Kenneth Anderton
  • Patent number: 4995902
    Abstract: The invention relates to novel herbicidally active cyclohexanediones of formula I or I' ##STR1## in which R.sup.1 and R.sup.2 independently of one another are each hydrogen; halogen; nitro; cyano; C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 alkoxy; C.sub.1 -C.sub.4 alkyl-S(O).sub.n --; COR.sup.8 ; C.sub.1 -C.sub.4 haloalkoxy; or C.sub.1 -C.sub.4 haloalkyl; R.sup.3, R.sup.4 and R.sup.5 independently of one another are each hydrogen; C.sub.1 -C.sub.4 alkyl; or phenyl or benzyl each unsubstituted or substituted by up to three identical or different substituents from halogen, nitro, cyano, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkyl-S(O).sub.n --, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkyl-S(O).sub.n -- and C.sub.1 -C.sub.4 haloalkoxy; R.sup.6 is hydrogen; C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxycarbonyl; or cyano; R.sup.7 is OH; or O.sup..crclbar. M.sup..sym. ; R.sup.8 is OH; C.sub.1 -C.sub.4 alkoxy; NH.sub.2 ; C.sub.1 -C.sub.4 alkylamino; or di-C.sub.1 - C.sub.
    Type: Grant
    Filed: July 11, 1989
    Date of Patent: February 26, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Hans-Georg Brunner
  • Patent number: RE33478
    Abstract: Certain novel pyridinyloxyphenoxy alkanoic acids, pyridinylthiophenoxy alkanoic acids, derivatives thereof and related compounds are described. More specifically, these novel compounds bear a fluorine substituent in the 3-position of the pyridinyl group and in the 5-position the substituent is selected from chlorine, CF.sub.3, CF.sub.2 Cl or CF.sub.2 H. These novel compounds exhibit surprising preemergent and postemergent activity in the control of grassy weeds.
    Type: Grant
    Filed: October 31, 1988
    Date of Patent: December 11, 1990
    Assignee: The Dow Chemical Company
    Inventors: Howard Johnston, Lillian H. Troxell