Halogen Attached Indirectly To The Six-membered Hetero Ring By Nonionic Bonding Patents (Class 546/346)
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Patent number: 4668792Abstract: Substituted [1,1'-biphenyl]-3-ylmethyl compounds carrying leaving groups are intermediates to insecticidal esters.Type: GrantFiled: December 20, 1983Date of Patent: May 26, 1987Assignee: FMC CorporationInventor: Ernest L. Plummer
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Patent number: 4650875Abstract: (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: GrantFiled: May 9, 1983Date of Patent: March 17, 1987Assignee: The Dow Chemical CompanyInventor: George S. Fujioka
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Patent number: 4649201Abstract: 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: GrantFiled: December 27, 1985Date of Patent: March 10, 1987Assignee: The Dow Chemical CompanyInventor: David D. Friese
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Patent number: 4649202Abstract: 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: GrantFiled: March 22, 1985Date of Patent: March 10, 1987Assignee: Ethyl CorporationInventors: Paul F. Ranken, Venkataraman Ramachandran
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Patent number: 4645771Abstract: 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: GrantFiled: September 30, 1982Date of Patent: February 24, 1987Assignee: Imperial Chemical Industries PLCInventor: Stuart D. Mills
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Patent number: 4636565Abstract: 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: GrantFiled: March 13, 1985Date of Patent: January 13, 1987Assignee: The Dow Chemical CompanyInventors: John A. Werner, Charles A. Wilson, Craig E. Mixan
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Patent number: 4634771Abstract: 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: GrantFiled: July 25, 1985Date of Patent: January 6, 1987Assignee: Stauffer Chemical CompanyInventors: Kyung S. Shim, Arthur D. F. Toy, James B. Heather
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Patent number: 4626593Abstract: 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: GrantFiled: April 22, 1985Date of Patent: December 2, 1986Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: John A. Parker, Alvin H. Heimbuch, Ming-Ta S. Hsu, Timothy S. Chen
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Patent number: 4625035Abstract: 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: GrantFiled: October 21, 1985Date of Patent: November 25, 1986Assignee: The Dow Chemical CompanyInventor: John A. Werner
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Patent number: 4604243Abstract: 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: GrantFiled: July 25, 1985Date of Patent: August 5, 1986Assignee: Ethyl CorporationInventor: Robert I. Davidson
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Patent number: 4604467Abstract: 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: GrantFiled: March 25, 1985Date of Patent: August 5, 1986Assignee: Ethyl CorporationInventors: Venkataraman Ramachandran, Paul F. Ranken
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Patent number: 4590279Abstract: (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: GrantFiled: August 4, 1983Date of Patent: May 20, 1986Assignee: The Dow Chemical CompanyInventors: Alexander P. Fung, Charles A. Wilson
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Patent number: 4577028Abstract: 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: GrantFiled: October 14, 1982Date of Patent: March 18, 1986Assignee: Ciba-Geigy CorporationInventors: Pierre Martin, Eginhard Steiner
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Patent number: 4567273Abstract: (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: GrantFiled: March 14, 1984Date of Patent: January 28, 1986Assignee: The Dow Chemical CompanyInventor: Alexander P. Fung
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Patent number: 4564681Abstract: 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: GrantFiled: September 24, 1982Date of Patent: January 14, 1986Assignee: Kalama Chemical, Inc.Inventors: Michael J. Marinak, John L. Simonson
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Patent number: 4563446Abstract: 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: GrantFiled: July 19, 1984Date of Patent: January 7, 1986Assignee: Takeda Chemical Industries, Ltd.Inventors: Shinji Terao, Kohei Nishikawa
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Patent number: 4563529Abstract: 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: GrantFiled: June 4, 1981Date of Patent: January 7, 1986Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Yasuhiro Tsujii, Shigeyuki Nishimura
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Patent number: 4556661Abstract: 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: GrantFiled: August 27, 1982Date of Patent: December 3, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Franz Dorn, Francois Montavon, Milos Suchy
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Patent number: 4554352Abstract: 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: GrantFiled: September 29, 1983Date of Patent: November 19, 1985Assignee: Ethyl CorporationInventor: Paul F. Ranken
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Patent number: 4552964Abstract: 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: GrantFiled: September 16, 1983Date of Patent: November 12, 1985Assignee: Ethyl CorporationInventor: Venkataraman Ramachandran
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Patent number: 4552963Abstract: 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: GrantFiled: May 23, 1983Date of Patent: November 12, 1985Assignee: Ethyl CorporationInventor: Venkataraman Ramachandran
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Patent number: 4550167Abstract: 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: GrantFiled: May 23, 1983Date of Patent: October 29, 1985Assignee: Ethyl CorporationInventor: Venkataraman Ramachandran
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Patent number: 4547577Abstract: 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: GrantFiled: June 8, 1984Date of Patent: October 15, 1985Assignee: The Dow Chemical CompanyInventors: Janice E. Gatlin, Mark A. VanDort, Curtis L. Volkmann
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Patent number: 4546192Abstract: 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: GrantFiled: September 23, 1982Date of Patent: October 8, 1985Assignee: The Dow Chemical CompanyInventors: George S. Fujioka, Alexander P. Fung
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Patent number: 4540793Abstract: 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: GrantFiled: September 16, 1983Date of Patent: September 10, 1985Assignee: Ethyl CorporationInventor: Venkataraman Ramachandran
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Patent number: 4521428Abstract: 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: GrantFiled: August 16, 1983Date of Patent: June 4, 1985Assignee: SanofiInventors: Dino Nisato, Marco Frigerio, Giovanna F. Miranda
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Patent number: 4499276Abstract: 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: GrantFiled: March 14, 1983Date of Patent: February 12, 1985Assignee: The Dow Chemical CompanyInventors: Sudarshan K. Malhotra, Jon A. Orvik
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Patent number: 4499277Abstract: 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: GrantFiled: March 14, 1983Date of Patent: February 12, 1985Assignee: The Dow Chemical CompanyInventors: Sudarhshan K. Malhotra, Jon A. Orvik
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Patent number: 4493932Abstract: 2-Fluoro-pyridine compounds are contacted with a chlorinating agent at superatmospheric pressures to yield 2-chloro-pyridine compounds.Type: GrantFiled: September 13, 1982Date of Patent: January 15, 1985Assignee: The Dow Chemical CompanyInventor: John A. Werner
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Patent number: 4490535Abstract: 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: GrantFiled: June 20, 1983Date of Patent: December 25, 1984Assignee: Ethyl CorporationInventor: Thomas J. Walter
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Patent number: 4477673Abstract: 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: GrantFiled: January 17, 1983Date of Patent: October 16, 1984Assignee: Ciba-Geigy CorporationInventor: Jurgen Kaschig
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Patent number: 4474602Abstract: 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: GrantFiled: January 19, 1982Date of Patent: October 2, 1984Assignee: The Dow Chemical CompanyInventors: Lowell D. Markley, John M. Soper
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Patent number: 4472408Abstract: 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: GrantFiled: March 3, 1982Date of Patent: September 18, 1984Assignee: SanofiInventors: Dino Nisato, Emilio Crisafulli, Alberto Bianchetti, Paolo Carminati
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Patent number: 4448967Abstract: 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: GrantFiled: August 20, 1982Date of Patent: May 15, 1984Assignee: Imperial Chemical Industries PLCInventor: Graham Whittaker
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Patent number: 4443449Abstract: 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: GrantFiled: April 5, 1982Date of Patent: April 17, 1984Assignee: The Boots Company LimitedInventors: James E. Jeffery, Eric C. Wilmshurst
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Patent number: 4429132Abstract: 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: GrantFiled: April 27, 1982Date of Patent: January 31, 1984Assignee: Imperial Chemical Industries PLCInventor: Graham Whittaker
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Patent number: 4423234Abstract: Improved yields of biaromatic compounds, e.g., unsymmetrical biphenyl compounds, result by incorporating metallic copper in a non-aqueous diazonium-type coupling reaction.Type: GrantFiled: May 17, 1982Date of Patent: December 27, 1983Assignee: FMC CorporationInventors: Ernest L. Plummer, David E. Seelye
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Patent number: 4420434Abstract: 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: GrantFiled: January 9, 1981Date of Patent: December 13, 1983Assignee: Ciba-Geigy CorporationInventor: Robert A. Falk
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Patent number: 4419514Abstract: 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: GrantFiled: May 18, 1981Date of Patent: December 6, 1983Assignee: The Dow Chemical CompanyInventors: Lennon H. McKendry, Michael J. Ricks, Richard B. Rogers
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Patent number: 4417055Abstract: 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: GrantFiled: March 9, 1982Date of Patent: November 22, 1983Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Yasuhiro Tsujii, Shigeyuki Nishimura
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Patent number: 4405792Abstract: 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: GrantFiled: September 8, 1981Date of Patent: September 20, 1983Assignee: Ethyl CorporationInventor: Thomas J. Walter
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Patent number: 4393214Abstract: 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: GrantFiled: March 13, 1981Date of Patent: July 12, 1983Assignee: Imperial Chemical Industries PLCInventors: Norman L. Roberts, Graham Whitaker
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Patent number: 4348525Abstract: [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: GrantFiled: April 9, 1981Date of Patent: September 7, 1982Assignee: The University of AkronInventors: Gerald F. Koser, Richard H. Wettach
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Patent number: 4339455Abstract: 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, COOHType: GrantFiled: July 17, 1979Date of Patent: July 13, 1982Assignee: Consortium fur Elektrochemische Industrie GmbHInventors: Fritz Sauter, Otto Eberle, Beate Suss, Rudolf Weissgerber
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Patent number: 4327220Abstract: Reducing trichloromethyl substituent on pyridine ring to dichloromethyl using a copper catalyst and a reducing agent.Type: GrantFiled: December 29, 1980Date of Patent: April 27, 1982Assignee: The Dow Chemical CompanyInventor: Jon A. Orvik
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Patent number: 4311703Abstract: Novel azacycloalkanes, azacycloalkenes and derivatives thereof and methods of preparing same are described. These compounds are useful as antidepressants, anticonvulsants, tranquilizers and analgetics.Type: GrantFiled: August 1, 1980Date of Patent: January 19, 1982Assignee: American Hoechst CorporationInventors: Lawrence L. Martin, Helen H. Ong, Vernon B. Anderson, Charles A. Crichlow
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Process for producing pyridine derivatives having a trifluoromethyl group at .beta.-position thereof
Patent number: 4288599Abstract: 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: GrantFiled: February 26, 1980Date of Patent: September 8, 1981Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Yasuhiro Tsujii, Shigeyuki Nishimura -
Patent number: 4283397Abstract: 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: GrantFiled: August 1, 1979Date of Patent: August 11, 1981Assignee: Merck & Co., Inc.Inventor: John Hannah
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Patent number: 4282219Abstract: 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: GrantFiled: August 1, 1979Date of Patent: August 4, 1981Assignee: Merck & Co., Inc.Inventor: John Hannah
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Patent number: 4277608Abstract: 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: GrantFiled: April 18, 1980Date of Patent: July 7, 1981Assignee: Eli Lilly and CompanyInventors: Dennis M. Zimmerman, Roger L. Robey