Halogen Attached Indirectly To The Six-membered Hetero Ring By Nonionic Bonding Patents (Class 546/346)
  • Patent number: 4668792
    Abstract: Substituted [1,1'-biphenyl]-3-ylmethyl compounds carrying leaving groups are intermediates to insecticidal esters.
    Type: Grant
    Filed: December 20, 1983
    Date of Patent: May 26, 1987
    Assignee: FMC Corporation
    Inventor: Ernest L. Plummer
  • Patent number: 4650875
    Abstract: (Trichloromethyl)pyridine compounds are reacted in the liquid phase with HF in the presence of a metal halide catalyst at superatmospheric pressures to form (trifluoromethyl)pyridine compounds in a high yield.
    Type: Grant
    Filed: May 9, 1983
    Date of Patent: March 17, 1987
    Assignee: The Dow Chemical Company
    Inventor: George S. Fujioka
  • Patent number: 4649201
    Abstract: Ferric chloride is removed from mixtures with chlorinated and/or fluorinated pyridines and methylpyridines by extraction with diol solvents. For example, the ferric chloride in halopyridine mixtures containing 2,3,5,6-tetrachloropyridine was removed by extraction with ethylene glycol. The purified halopyridines are useful intermediates for the production of insecticides, herbicides, and fungicides.
    Type: Grant
    Filed: December 27, 1985
    Date of Patent: March 10, 1987
    Assignee: The Dow Chemical Company
    Inventor: David D. Friese
  • Patent number: 4649202
    Abstract: A 4-cyclohexenylpyridine is brominatively aromatized to the corresponding 4-phenylpyridine by brominating the cyclohexenylpyridine, such as a 4-(halocyclohexenyl)pyridine, especially a 4-(4-halocyclohex-3-enyl)pyridine hydrochloride, and heating the brominated product in the presence or absence of any added base or hydrogen acceptor to form, e.g., a 4-(halophenyl)pyridine. The invention is of particular utility in the manufacture of intermediates of antibacterial 1-alkyl-1,4-dihydro-4-oxo-7-(4-pyridyl)-3-quinolinecarboxylic acids.
    Type: Grant
    Filed: March 22, 1985
    Date of Patent: March 10, 1987
    Assignee: Ethyl Corporation
    Inventors: Paul F. Ranken, Venkataraman Ramachandran
  • Patent number: 4645771
    Abstract: The disclosure concerns novel 1-benzyl-1,2,3,6-tetrahydropyridine derivatives of the formula: ##STR1## wherein R.sup.1 is hydrogen or a (1-4C)-alkyl radical, and benzene ring A bears one or two substituents selected from combinations of halogeno, (1-4C)-alkyl, (1-4C)-alkoxy, hydroxy, nitro, cyano, carboxamido, carboxyl, [(1-4C)-alkoxy]carbonyl, hydroxymethylene, amino, (1-4C)-alkanoylamino, (1-4C)-alkylsulphonamido, [(1-4C)-alkoxy]carbonyloxy, (1-4C)-alkanoyloxy and optionally substituted benzoyloxy radicals, and their pharmaceutically acceptable salts; pharmaceutical compositions thereof; analogy processes for their manufacture; and methods of medical treatment employing such derivatives.The compounds of formula I are inhibitors of the aggregation of blood platelets and are of application in the treatment or prophylaxis of thrombosis or occlusive vascular disease.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: February 24, 1987
    Assignee: Imperial Chemical Industries PLC
    Inventor: Stuart D. Mills
  • Patent number: 4636565
    Abstract: Preparation of 2,3-dichloro-5-trichloromethylpyridine in high yields and purity by chlorinating 2-chloro-5-trichloromethylpyridine at 70.degree. to 250.degree. C. with chlorine in the presence of a catalyst containing one or more molybdenum, tungsten or ruthenium compounds.
    Type: Grant
    Filed: March 13, 1985
    Date of Patent: January 13, 1987
    Assignee: The Dow Chemical Company
    Inventors: John A. Werner, Charles A. Wilson, Craig E. Mixan
  • Patent number: 4634771
    Abstract: There is disclosed a method for the conversion of a carboxylic acid group on the ring of an aromatic or N-heteroaromatic compound to a trichloromethyl group which comprises contacting the aromatic or N-heteroaromatic compound with a phenylphosphonous dichloride, phosphorus trichloride and chlorine.
    Type: Grant
    Filed: July 25, 1985
    Date of Patent: January 6, 1987
    Assignee: Stauffer Chemical Company
    Inventors: Kyung S. Shim, Arthur D. F. Toy, James B. Heather
  • Patent number: 4626593
    Abstract: Vinyl pyridines including vinyl stilbazole materials and vinyl styrylpyridine oligomer materials are disclosed. These vinylpyridines form copolymers with bismaleimides which copolymers have good fire retardancy and decreased brittleness. The cure temperatures of the copolymers are substantially below the cure temperatures of the bismaleimides alone. Reinforced composites made from the cured copolymers are disclosed as well.
    Type: Grant
    Filed: April 22, 1985
    Date of Patent: December 2, 1986
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: John A. Parker, Alvin H. Heimbuch, Ming-Ta S. Hsu, Timothy S. Chen
  • Patent number: 4625035
    Abstract: Novel 2,3-difluoro-5-(trifluoromethyl)pyridine is prepared by fluorinating 3-chloro-2-fluoro-5-(trifluoromethyl)pyridine under favorable conditions. The compound is useful as a chemical intermediate in the preparation of herbicides.
    Type: Grant
    Filed: October 21, 1985
    Date of Patent: November 25, 1986
    Assignee: The Dow Chemical Company
    Inventor: John A. Werner
  • Patent number: 4604243
    Abstract: An olefin, especially an activated olefin, is arylated by reaction with an arylamine, such as an aniline, in an inert polar organic solvent and in the presence of an alkyl nitrite, a hydrogen halide, and a catalytic amount of a copper catalyst having the copper in an oxidation state below +2.
    Type: Grant
    Filed: July 25, 1985
    Date of Patent: August 5, 1986
    Assignee: Ethyl Corporation
    Inventor: Robert I. Davidson
  • Patent number: 4604467
    Abstract: A 4-cyclohexenylpyridine is brominatively aromatized to the corresponding 4-phenylpyridine by brominating the cyclohexenylpyridine, such as a 4-(halocyclohexenyl)pyridine, especially a 4-(4-halocyclohex-3-enyl)pyridine hydrohalide, and heating the brominated product in an inert solvent and in the presence of a base to form, e.g., a 4-(halophenyl)pyridine. The invention is of particular utility in the manufacture of intermediates of antibacterial 1-alkyl- 1,4-dihydro-4-oxo-7-(4-pyridyl)-3-quinolinecarboxylic acids.
    Type: Grant
    Filed: March 25, 1985
    Date of Patent: August 5, 1986
    Assignee: Ethyl Corporation
    Inventors: Venkataraman Ramachandran, Paul F. Ranken
  • Patent number: 4590279
    Abstract: (Trifluoromethyl)pyridine compounds are prepared by contacting (trichloromethyl)pyridine compounds with hydrogen fluoride in the presence of a catalytic amount of a catalyst selected from the group consisting of FeCl.sub.2, FeF.sub.2 and mixtures thereof under liquid phase conditions. The (trifluoromethyl)pyridine compounds are useful as intermediates for the preparation of agricultural chemicals.
    Type: Grant
    Filed: August 4, 1983
    Date of Patent: May 20, 1986
    Assignee: The Dow Chemical Company
    Inventors: Alexander P. Fung, Charles A. Wilson
  • Patent number: 4577028
    Abstract: Novel 5-haloalkyl-pyridines suitable for producing pesticidal compositions, particularly insecticides, and corresponding to the formula ##STR1## wherein R is a C.sub.2 -C.sub.10 -alkyl group which is uniformly or nonuniformly substituted by 1 to 21 halogen atoms, and X is halogen;processes for producing them, as well as to the novel starting products and intermediates used or intermediately produced or formed in the production processes.
    Type: Grant
    Filed: October 14, 1982
    Date of Patent: March 18, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Pierre Martin, Eginhard Steiner
  • Patent number: 4567273
    Abstract: (Trifluoromethyl)pyridine compounds are prepared in high yields and with a high selectivity by using a mercury or silver fluorinating agent, i.e., HgF.sub.2, AgF, AgF.sub.2, in a liquid phase halogen exchange process.
    Type: Grant
    Filed: March 14, 1984
    Date of Patent: January 28, 1986
    Assignee: The Dow Chemical Company
    Inventor: Alexander P. Fung
  • Patent number: 4564681
    Abstract: Preparation of high yields of mixtures rich in 3-chloro-2-trichloromethyl pyridine by maintaining a chlorine to alpha-picoline weight ratio of at least about 8:1 when feeding alpha-picoline hydrochloride and excess chlorine to reactor means at a temperature in the range of about 135.degree. C. to about 170.degree. C. and in the absence of a catalyst, the reactants being contained in a well mixed diluent producing essentially no hydrogen chloride by reaction with chlorine in the indicated temperature range.
    Type: Grant
    Filed: September 24, 1982
    Date of Patent: January 14, 1986
    Assignee: Kalama Chemical, Inc.
    Inventors: Michael J. Marinak, John L. Simonson
  • Patent number: 4563446
    Abstract: Novel compounds of the formula: ##STR1## wherein R.sup.2 is an aromatic or heterocyclic group, which may optionally be substituted, R.sup.2 is a methyl group, a hydroxymethyl group, a nitroxymethyl group, a formyl group, a nitrogen-containing five-membered ring-methyl group, an acetal-methyl group, a trialkylsilyloxymethyl group, an alkyl- or aryl-sulfonyloxymethyl group, an alkyl- or aryl-sulfonylaminocarbonyloxymethyl group, an acyloxymethyl group, an alkoxycarbonyloxymethyl group, a halogenomethyl group, an alkoxymethyl group, an aryloxymethyl group, a cyano group, a carbamoyl group which may optionally be substituted, a carbamoyloxymethyl group which may optionally be substituted, a thiocarbamoyloxymethyl group which may optionally be substituted, and an alkoxycarbonyl group, n is an integer of 1 to 20, and ##STR2## provided that n is an integer of 9 to 20 when ##STR3## and, at the same time, R.sup.
    Type: Grant
    Filed: July 19, 1984
    Date of Patent: January 7, 1986
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Shinji Terao, Kohei Nishikawa
  • Patent number: 4563529
    Abstract: A trifluoromethylpyridine selected from the group consisting of .alpha.-trifluoromethylpyridine, .gamma.-trifluoromethylpyridine, a bis(trifluoromethyl)pyridine and chlorides thereof which have 1 to 3 chlorine atoms in its pyridine nucleus is produced by reacting a pyridine derivative selected from the group consisting of .alpha.-picoline, .gamma.-picoline and a lutidine with chlorine and anhydrous hydrogen fluoride at a temperature of 300.degree. to 600.degree. C. in a vapor phase in the presence of a diluent and a catalyst comprising a fluoride of a metallic element selected from the group consisting of aluminum, chromium, iron, nickel, manganese, cobalt and copper.
    Type: Grant
    Filed: June 4, 1981
    Date of Patent: January 7, 1986
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Yasuhiro Tsujii, Shigeyuki Nishimura
  • Patent number: 4556661
    Abstract: Novel pyridine and pyrazine derivatives of the formula ##STR1## wherein R.sup.4 is 3-pyridyl, 3-pyridyl-1-oxide, 2-pyrazinyl, 2-pyrazinyl-1-oxide, 2-pyrazinyl-4-oxide or 2-pyrazinyl-1,4-dioxide, and R, R.sup.1, R.sup.2 and R.sup.3 are as hereinafter set forth, processes for their preparation, fungicidal compositions containing said compounds, and methods for the use of such compounds or compositions for combatting fungi in agriculture and in horticulture are disclosed. Novel starting materials and fungicidal active substances of the formula ##STR2## wherein R.sup.4' is 3-pyridyl or 2-pyrazinyl, and R and R.sup.1" as hereinafter set forth, which are used for the preparation of the compounds of formula I, and their N-oxides, as well as fungicidal compositions containing these compounds as the active substance, are also described.
    Type: Grant
    Filed: August 27, 1982
    Date of Patent: December 3, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Franz Dorn, Francois Montavon, Milos Suchy
  • Patent number: 4554352
    Abstract: 4-(Bromophenyl)pyridines, useful in preparing bactericides, are prepared by reacting a 4-phenylpyridine with bromine in the presence of an excess of a Lewis acid catalyst, preferably aluminum chloride.
    Type: Grant
    Filed: September 29, 1983
    Date of Patent: November 19, 1985
    Assignee: Ethyl Corporation
    Inventor: Paul F. Ranken
  • Patent number: 4552964
    Abstract: A 4-(1-chlorovinyl)pyridine, preferably 4-(1-chlorovinyl)pyridine itself, is reacted with a butadiene, preferably chloroprene, to prepare a 4-(1-chlorocyclohex-3-enyl)pyridine. The preferred products are useful as intermediates in the preparation of antibacterial 1-alkyl-1,4-dihydro-4-oxo-7-pyridinyl-3-quinolinecarboxylic acids.
    Type: Grant
    Filed: September 16, 1983
    Date of Patent: November 12, 1985
    Assignee: Ethyl Corporation
    Inventor: Venkataraman Ramachandran
  • Patent number: 4552963
    Abstract: The yield of Diels-Alder product obtained by reacting a haloprene with a 4-vinylpyridine is increased by conducting the reaction in the presence of a boron trifluoride catalyst, preferably a boron trifluoride etherate. The product obtained by the reaction, a mixture of 4-(chlorocyclohex-3-enyl)pyridines, is useful in the production of antibacterial 1-alkyl-1,4-dihydro-4-oxo-7-pyridinyl-3-quinolinecarboxylic acids.
    Type: Grant
    Filed: May 23, 1983
    Date of Patent: November 12, 1985
    Assignee: Ethyl Corporation
    Inventor: Venkataraman Ramachandran
  • Patent number: 4550167
    Abstract: Diels-Alder products obtained by reacting a haloprene with a 4-vinylpyridine, i.e., mixtures of 4-(halocyclohex-3-enyl)pyridine isomers, are reacted with a relatively strong acid, i.e., an acid having a dissociation constant of at least 1.7.times.10.sup.-5 at 25.degree. C., to form salts which are readily separated and/or reduced.
    Type: Grant
    Filed: May 23, 1983
    Date of Patent: October 29, 1985
    Assignee: Ethyl Corporation
    Inventor: Venkataraman Ramachandran
  • Patent number: 4547577
    Abstract: Preparation of 3-chloro-2-fluoro-5-(trifluoromethyl)pyridine in a liquid phase halogen exchange reaction from 2,3-dichloro-5-(trichloromethyl)pyridine in the absence of a catalyst.
    Type: Grant
    Filed: June 8, 1984
    Date of Patent: October 15, 1985
    Assignee: The Dow Chemical Company
    Inventors: Janice E. Gatlin, Mark A. VanDort, Curtis L. Volkmann
  • Patent number: 4546192
    Abstract: Ring-fluorinated pyridine compounds are contacted with a chlorinating agent, preferably in the presence of a catalyst, under favorable conditions to yield pyridine compounds having a chlorine substituted in the ring-fluorine position(s).
    Type: Grant
    Filed: September 23, 1982
    Date of Patent: October 8, 1985
    Assignee: The Dow Chemical Company
    Inventors: George S. Fujioka, Alexander P. Fung
  • Patent number: 4540793
    Abstract: 4-(1-Chlorovinyl)pyridines are prepared by heating an acid salt of 4-(1,2-dichloroethyl)pyridine in an inert solvent until dehydrohalogenation is effected.
    Type: Grant
    Filed: September 16, 1983
    Date of Patent: September 10, 1985
    Assignee: Ethyl Corporation
    Inventor: Venkataraman Ramachandran
  • Patent number: 4521428
    Abstract: Novel 4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridines of formula ##STR1## wherein R is an unsubstituted or by an alkyl group of from 1 to 4 carbon atoms substituted pyridyl, pyridyl 1-oxide or naphthyl group and Alk is a straight or branched chain alkylene group of from 2 to 4 carbon atoms are anorexigenic agents useful for treating obesity.
    Type: Grant
    Filed: August 16, 1983
    Date of Patent: June 4, 1985
    Assignee: Sanofi
    Inventors: Dino Nisato, Marco Frigerio, Giovanna F. Miranda
  • Patent number: 4499276
    Abstract: 2(6)-(Trichloromethyl)pyridines are reduced to the corresponding 2(6)-(dichloromethyl)pyridines by treatment with a strong base and an anionic reductant derived from a reductant source material selected from the group consisting of chloroform, dimethylsulfoxide, dimethylsulfone, and a ketone having a base-abstractable hydrogen, said treatment taking place in the presence of a polar, non-hydroxylic solvent and/or a phase transfer catalyst.
    Type: Grant
    Filed: March 14, 1983
    Date of Patent: February 12, 1985
    Assignee: The Dow Chemical Company
    Inventors: Sudarshan K. Malhotra, Jon A. Orvik
  • Patent number: 4499277
    Abstract: 2(6)-(Trichloromethyl)pyridines are reduced to the corresponding 2(6)-(dichloromethyl)pyridines by treatment with a strong base and an anionic reductant derived from a reductant source material selected from the group consisting of dialkylphosphite and trialkylphosphite said treatment taking place in the presence of a polar, non-hydroxylic solvent and/or a phase transfer catalyst.
    Type: Grant
    Filed: March 14, 1983
    Date of Patent: February 12, 1985
    Assignee: The Dow Chemical Company
    Inventors: Sudarhshan K. Malhotra, Jon A. Orvik
  • Patent number: 4493932
    Abstract: 2-Fluoro-pyridine compounds are contacted with a chlorinating agent at superatmospheric pressures to yield 2-chloro-pyridine compounds.
    Type: Grant
    Filed: September 13, 1982
    Date of Patent: January 15, 1985
    Assignee: The Dow Chemical Company
    Inventor: John A. Werner
  • Patent number: 4490535
    Abstract: 4-(3- and 4-chlorocyclohex-3-enyl)pyridines, useful as intermediates in the preparation of pesticides and bactericides, are prepared by reacting a 4-vinylpyridine with chloroprene.
    Type: Grant
    Filed: June 20, 1983
    Date of Patent: December 25, 1984
    Assignee: Ethyl Corporation
    Inventor: Thomas J. Walter
  • Patent number: 4477673
    Abstract: The invention relates to compounds of the formula I ##STR1## wherein R' is bound in the 4- or 5-position, R and R' are --CH.sub.2 OH, --CH.sub.2 CH.sub.2 OH, --CH.sub.2 CH.sub.2 OCH.sub.2 C.sub.6 H.sub.5, --CH.sub.2 --X, --CH.sub.2 P.sup..sym. (Y).sub.3 X.sup..crclbar., --CH.sub.2 P(O)(C.sub.1-3 alkoxy).sub.2 or --CH.dbd.CH.sub.2, R" is C.sub.1-10 alkyl, X is a halogen atom, X.sup..crclbar. is the anion corresponding to X and Y is phenyl or phenyl which is substituted by a C.sub.1 -C.sub.5 alkyl group. These compounds can be obtained by a novel simple process in good to very good yield by co-cyclotrimerizing nitriles R"--CN with alkynes HC.dbd.C--Z (Z is --CH.sub.2 OH, --CH.sub.2 CH.sub.2 OH or --CH.sub.2 CH.sub.2 OCH.sub.2 C.sub.6 H.sub.5), in the presence of a cobalt(I) catalyst, dehydrating the resultant pyridines either to compounds of the formula I, in which R and R" are --CH.dbd.CH.sub.
    Type: Grant
    Filed: January 17, 1983
    Date of Patent: October 16, 1984
    Assignee: Ciba-Geigy Corporation
    Inventor: Jurgen Kaschig
  • Patent number: 4474602
    Abstract: Substituted pyridyl compounds, e.g. 2,6-dichloro-4(2-(2,2,2-trichloroethyl)oxiranyl) pyridine; herbicidal compositions containing such compounds and method for the control of undesired vegetation using these compositions.
    Type: Grant
    Filed: January 19, 1982
    Date of Patent: October 2, 1984
    Assignee: The Dow Chemical Company
    Inventors: Lowell D. Markley, John M. Soper
  • Patent number: 4472408
    Abstract: The invention relates to 4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridines of formula ##STR1## in which R represents a cyano, acetyl or cycloalkyl group of from 3 to 7 carbon atoms and Alk represents a straight or branched alkylene of from 1 to 4 carbon atoms, as well as to the salts thereof, having an anorectic activity, to a process for preparing same and to pharmaceutical compositions containing said compounds, useful in the treatment of obesity.
    Type: Grant
    Filed: March 3, 1982
    Date of Patent: September 18, 1984
    Assignee: Sanofi
    Inventors: Dino Nisato, Emilio Crisafulli, Alberto Bianchetti, Paolo Carminati
  • Patent number: 4448967
    Abstract: 3-Chloro-5-trifluoromethylpyridine and/or 2,3-dichloro-5-trifluoromethylpyridine are produced by selective vapor-phase chlorination of 3-trifluoromethylpyridine or 2-chloro-5-trifluoromethylpyridine in the presence of a copper catalyst.
    Type: Grant
    Filed: August 20, 1982
    Date of Patent: May 15, 1984
    Assignee: Imperial Chemical Industries PLC
    Inventor: Graham Whittaker
  • Patent number: 4443449
    Abstract: Compounds of formula I ##STR1## in which R.sub.1 is H or C.sub.1-3 alkyl; R.sub.2 is H or C.sub.1-3 alkyl; R.sub.3 and/or R.sub.4 are H, C.sub.1-3 alkyl, C.sub.3-6 alkenyl, C.sub.3-6 alkynyl, C.sub.3-7 cycloalkyl or R.sub.3 and R.sub.4 together with the nitrogen atom form a heterocyclic ring system; R.sub.5 and/or R.sub.6 are H, halo, CF.sub.3, or C.sub.1-3 alkyl (with the proviso that R.sub.5 and R.sub.6 cannot both be H or methyl) or R.sub.5 and R.sub.6 together with the carbon atoms to which they are attached form a second benzene ring and R.sub.7 and/or R.sub.8 are H or C.sub.1-3 alkyl show therapeutic activity in the treatment of depression. Pharmaceutical compositions and processes for preparing compounds of formula I are disclosed.
    Type: Grant
    Filed: April 5, 1982
    Date of Patent: April 17, 1984
    Assignee: The Boots Company Limited
    Inventors: James E. Jeffery, Eric C. Wilmshurst
  • Patent number: 4429132
    Abstract: 3-Trichloromethylpyridines are produced from 3-methylpyridines by reaction with chlorine in the vapor phase in the presence of a metal oxide or metal halide catalyst.
    Type: Grant
    Filed: April 27, 1982
    Date of Patent: January 31, 1984
    Assignee: Imperial Chemical Industries PLC
    Inventor: Graham Whittaker
  • Patent number: 4423234
    Abstract: Improved yields of biaromatic compounds, e.g., unsymmetrical biphenyl compounds, result by incorporating metallic copper in a non-aqueous diazonium-type coupling reaction.
    Type: Grant
    Filed: May 17, 1982
    Date of Patent: December 27, 1983
    Assignee: FMC Corporation
    Inventors: Ernest L. Plummer, David E. Seelye
  • Patent number: 4420434
    Abstract: The instant invention relates to the use of ion-pair complexes derived from anionic perfluoroalkyl sulfonates, carboxylates, phosphates and phosphonates and cationic perfluoroalkyl surfactants. Such complexes are capable of reducing the surface tension of aqueous solutions dramatically even at extremely low concentrations, and are useful as wetting, spreading and leveling agents and are especially preferred as components in so-called aqueous film forming foam compositions for fighting polar and non-polar solvent and fuel fires.
    Type: Grant
    Filed: January 9, 1981
    Date of Patent: December 13, 1983
    Assignee: Ciba-Geigy Corporation
    Inventor: Robert A. Falk
  • Patent number: 4419514
    Abstract: Method for converting carboxylic acid groups to trichloromethyl groups which comprises contacting a compound containing a carboxylic acid group with a phenylphosphonic dichloride and phosphorus pentachloride and recovering the thus produced product.
    Type: Grant
    Filed: May 18, 1981
    Date of Patent: December 6, 1983
    Assignee: The Dow Chemical Company
    Inventors: Lennon H. McKendry, Michael J. Ricks, Richard B. Rogers
  • Patent number: 4417055
    Abstract: A pyridine derivative having the formula ##STR1## wherein X.sup.2 and Y.sup.2 represents hydrogen atom or chlorine atom is produced by reacting a pyridine compound having the formula ##STR2## wherein X.sup.1 and Y.sup.1 represent hydrogen atom or chlorine atom, with chlorine and anhydrous hydrogen fluoride by a vapor phase reaction in the presence of a catalyst at a temperature of 250.degree. to 600.degree. C. using as the catalyst a fluoride of a metal selected from the group consisting of copper, vanadium, tin, bismuth, zirconium, magnesium, barium, zinc, calcium, potassium and sodium.
    Type: Grant
    Filed: March 9, 1982
    Date of Patent: November 22, 1983
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Yasuhiro Tsujii, Shigeyuki Nishimura
  • Patent number: 4405792
    Abstract: 4-(Chlorophenyl)pyridines in which the chlorine atom is in the 3- or 4-position of the phenyl group are prepared by reacting a 4-vinyl pyridine with chloroprene to form a 4-(3- or 4-chlorocyclohex-3-enyl)pyridine and then catalytically dehydrogenating the 4-(3- or 4-chlorocyclohex-3-enyl)pyridine to form a 4-(3- or 4-chlorophenyl)pyridine. The 4-(3- and 4-monochlorocyclohex-3-enyl)pyridines are novel compounds.
    Type: Grant
    Filed: September 8, 1981
    Date of Patent: September 20, 1983
    Assignee: Ethyl Corporation
    Inventor: Thomas J. Walter
  • Patent number: 4393214
    Abstract: 2-chloro-5-trifluoromethylpyridine or a 2-chloro-5-perchlorofluoromethylpyridine is prepared by chlorination of 3-trifluoromethylpyridine or a 3-perchlorofluoromethylpyridine respectively in the vapor phase at a temperature in the range from 100.degree. C. to 500.degree. C.
    Type: Grant
    Filed: March 13, 1981
    Date of Patent: July 12, 1983
    Assignee: Imperial Chemical Industries PLC
    Inventors: Norman L. Roberts, Graham Whitaker
  • Patent number: 4348525
    Abstract: [Hydroxy(organosulfonyloxy)iodo]arenes are synthesized in neutral organic solvents by the reaction of ring-substituted [hydroxy(organosulfonyloxy)iodo]benzenes with iodoarenes via ligand transfer. The produced compounds are reacted with (triorganosilyl) arenes or (trihalosilyl)arenes in neutral organic solvents to produce diaryliodonium salts. The diaryliodonium salt synthesis proceeds in regiospecific fashion, aryliodination occurring at the point of attachment of the silicon atom in the silylarenes.
    Type: Grant
    Filed: April 9, 1981
    Date of Patent: September 7, 1982
    Assignee: The University of Akron
    Inventors: Gerald F. Koser, Richard H. Wettach
  • Patent number: 4339455
    Abstract: A 1-(3-pyridyl)-2,2,2-trihaloethyl compound of the formula I ##STR1## in which n is 0 or 1, R represents methyl and X is iodide, R' represents a radical of the formula II ##STR2## wherein V, Y and Z each represent a chlorine or bromine atom, A represents a radical of the general formula III ##STR3## in which B' is oxygen or sulphur and B stands for a member of the group consisting of an aliphatic radical having from 1-10 C-atoms of the group consisting of alkenyl radicals and alkyl radicals of the branched and straight chain type, the phenyl radical, an aralkyl radical having from 7-12 C-atoms and an amino group of the general formula IV ##STR4## in which F and D are identical or different, and represent a member of the group consisting of hydrogen, aliphatic radicals of the branched or straight chain type and having from 1-10 C-atoms, the phenyl radical, a substituted phenyl radical containing at least one substituent selected from the group consisting of lower alkoxy, lower alkanoyl, lower alkyl ester, COOH
    Type: Grant
    Filed: July 17, 1979
    Date of Patent: July 13, 1982
    Assignee: Consortium fur Elektrochemische Industrie GmbH
    Inventors: Fritz Sauter, Otto Eberle, Beate Suss, Rudolf Weissgerber
  • Patent number: 4327220
    Abstract: Reducing trichloromethyl substituent on pyridine ring to dichloromethyl using a copper catalyst and a reducing agent.
    Type: Grant
    Filed: December 29, 1980
    Date of Patent: April 27, 1982
    Assignee: The Dow Chemical Company
    Inventor: Jon A. Orvik
  • Patent number: 4311703
    Abstract: Novel azacycloalkanes, azacycloalkenes and derivatives thereof and methods of preparing same are described. These compounds are useful as antidepressants, anticonvulsants, tranquilizers and analgetics.
    Type: Grant
    Filed: August 1, 1980
    Date of Patent: January 19, 1982
    Assignee: American Hoechst Corporation
    Inventors: Lawrence L. Martin, Helen H. Ong, Vernon B. Anderson, Charles A. Crichlow
  • Patent number: 4288599
    Abstract: Pyridine derivatives having a trifluoromethyl group at .beta.-position thereof are produced by reacting .beta.-picoline with chlorine and hydrogen fluoride in a vapor phase at high temperature for a short time. The reaction condition can be mild and the yield of the object compound is increased by reacting them in the presence of a specific metal fluodie. The pyridine derivatives useful as starting materials for agricultural chemicals and medicines can be continuously obtained by a simple reaction at high yield.
    Type: Grant
    Filed: February 26, 1980
    Date of Patent: September 8, 1981
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Yasuhiro Tsujii, Shigeyuki Nishimura
  • Patent number: 4283397
    Abstract: Disclosed are antibiotic cephalosporins (I) of the formula: ##STR1## wherein the stylized radical attached to the 7-amino nitrogen of the cephalosporin moiety represents a nitrogen-containing heterocyclic group (mono- or polycyclic); R is, inter alia, hydrogen, alkyl, heterocyclylalkyl, aryl, alkenyl, aralkyl, --NR.sub.2, --OR, COOR, CONR.sub.2 or CN; A is H or is conventionally known in the cephalosporin art; R.sup.2 is H, or loweralkoxyl; p is 1 or 2; and R.degree. is H or CH.sub.3. Also disclosed are the pharmaceutically acceptable salt and ester derivatives of I; processes for the preparation of such compounds; pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.
    Type: Grant
    Filed: August 1, 1979
    Date of Patent: August 11, 1981
    Assignee: Merck & Co., Inc.
    Inventor: John Hannah
  • Patent number: 4282219
    Abstract: Disclosed are antibiotic cephalosporins (I) of the formula: ##STR1## Wherein the stylized radical attached to the 7-amino nitrogen of the cephalosporin moiety represents a nitrogen-containing heterocyclic group (mono- or polycyclic); R is, inter alia, hydrogen, alkyl, heterocyclylalkyl, aryl, alkenyl, aralkyl, -NR.sub.2, -OR, COOR, CONR.sub.2 or CN; R.degree. is hydrogen or methyl; and R.sup.2 is H, or loweralkoxyl. Also disclosed are the pharmaceutically acceptable salt and ester derivatives of I; processes for the preparation of such compounds; pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.
    Type: Grant
    Filed: August 1, 1979
    Date of Patent: August 4, 1981
    Assignee: Merck & Co., Inc.
    Inventor: John Hannah
  • Patent number: 4277608
    Abstract: 4a-Arylhexahydro-1H-2-pyrindines and 4a-aryloctahydroquinolines analgesic agonists and antagonists are prepared doubly alkylating a 4-aryltetrahydropyridine with an .alpha.,.omega.-dihaloalkane.
    Type: Grant
    Filed: April 18, 1980
    Date of Patent: July 7, 1981
    Assignee: Eli Lilly and Company
    Inventors: Dennis M. Zimmerman, Roger L. Robey