Halogen Attached Indirectly To The Six-membered Hetero Ring By Nonionic Bonding Patents (Class 546/346)
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Patent number: 5599941Abstract: New N-substituted 4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridines useful in the treatment of intestinal motility disorders, of the following general formula ##STR1## wherein A represents a group -E-G or -L-M, where-E- is a straight or branched alkylene radical of from 2 to 4 carbon atoms,-G represents a radical selected from the group consisting of naphthyl mono-substituted with hydroxy or (C.sub.1 -C.sub.4)alkoxy; naphthyl di-substituted with hydroxy, (C.sub.1 -C.sub.4)alkoxy or (C.sub.1 -C.sub.4)alkyl; or napthyl substituted with methylenedioxy,-L- is a -Q-CH(OH)-- group wherein -Q- is a straight or branched alkylene radical of from 1 to 3 carbon atoms, and-M represents a radical selected from the group consisting of naphthyl; naphthyl mono- or di-substituted with hydroxy, (C.sub.1 -C.sub.4)alkoxy or (C.sub.1 -C.sub.4)alkyl or naphthyl substituted with methylenedioxy; pyridyl; or (C.sub.1 -C.sub.4)alkyl-pyridyl,and their salts with mineral or organic acids.Type: GrantFiled: May 31, 1995Date of Patent: February 4, 1997Assignee: SanofiInventors: Umberto Guzzi, Constantino Palmieri, Tiziano Croci
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Patent number: 5596101Abstract: New N-substituted 4-(3-trifluoromethylpheny1)-1,2,3,6-tetrahydropyridines useful in the treatment of intestinal motility disorders, of the following general formula ##STR1## wherein A represents a group --E--G or --L--M, where--E-- is a straight or branched alkylene radical of from 2 to 4 carbon atoms,--G represents a radical selected from the group consisting of naphthyl mono-substituted with hydroxy or (C.sub.1 -C.sub.4)alkoxy; naphthyl di-substituted with hydroxy, (C.sub.1 -C.sub.4)alkoxy or (C.sub.1 -C.sub.4)alkyl; or naphthyl substituted with methylenedioxy,--L-- is a --Q--CH(OH)-- group wherein --Q-- is a straight or branched alkylene radical of from 1 to 3 carbon atoms, and--M represents a radical selected from the group consisting of naphthyl; naphthyl mono- or di-substituted with hydroxy, (C.sub.1 -C.sub.4)alkoxy or (C.sub.1 -C.sub.4)alkyl or naphthyl substituted with methylenedioxy; pyridyl; or (C.sub.1 -C.sub.4)alkyl-pyridyl,and their salts with mineral or organic acids.Type: GrantFiled: May 31, 1995Date of Patent: January 21, 1997Assignee: SanofiInventors: Umberto Guzzi, Costantino Palmieri, Tiziano Croci
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Patent number: 5578595Abstract: Novel 2-(2,2-difluorocyclopropyl)-acetic acid derivatives of formula I ##STR1## wherein A is oxygen or --NR.sub.1 --,B is C.sub.2 -C.sub.6 alkylene,D is oxygen, sulfur or --O--CH.sub.2 --,E is phenyl; phenyl substituted by from one to three substituents selected from the group halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 haloalkyl and C.sub.1 -C.sub.4 alkoxy; a five-membered aromatic heterocycle having from one to three hetero atoms selected from the group nitrogen, oxygen and sulfur; a five-membered aromatic heterocycle having from one to three hetero atoms selected from the group nitrogen, oxygen and sulfur that is substituted by one or two substituents selected from the group halogen, C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.3 haloalkyl; a six-membered aromatic heterocycle having from one to three nitrogen atoms; or a six-membered aromatic heterocycle having from one to three nitrogen atoms that is substituted by one or two substituents selected from the group halogen, C.sub.1 -C.sub.4 alkyl and C.Type: GrantFiled: March 21, 1995Date of Patent: November 26, 1996Assignee: Ciba-Geigy CorporationInventor: Manfred B oger
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Patent number: 5569774Abstract: Chlorine-substituted olefins I ##STR1## (R.sup.1 =organic radical; R.sup.2 =--CN, --CO--R.sup.3, --CO--S--R.sup.3, --CO--O--R.sup.3 --CO--N(R.sup.4,R.sup.5); R.sup.3 =organic radical; R.sup.4, R.sup.5 =H, organic radical)are prepared by reacting oxiranes II ##STR2## in the presence of a carboxamide (IIIa) or of a lactam (IIIb) in liquid phase with a chlorinating agent (IV). The products I are important intermediates for dyes, drugs and crop protection agents.Type: GrantFiled: September 20, 1994Date of Patent: October 29, 1996Assignee: BASF AktiengesellschaftInventors: Bernd Schaefer, Irene Troetsch-Schaller
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Patent number: 5559238Abstract: New N-substituted 4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridines useful in the treatment of intestinal motility disorders, of the following general formula ##STR1## wherein A represents a group --E--G or --L--M, where--E-- is a straight or branched alkylene radical of from 2 to 4 carbon atoms,--G represents a radical selected from the group consisting of naphthyl mono-substituted with hydroxy or (C.sub.1 -C.sub.4)alkoxy; naphthyl di-substituted with hydroxy, (C.sub.1 -C.sub.4)alkoxy or (C.sub.1 -C.sub.4)alkyl; or naphthyl substituted with methylenedioxy,--L-- is a --Q--CH(OH)-- group wherein --Q-- is a straight or branched alkylene radical of from 1 to 3 carbon atoms, and--M represents a radical selected from the group consisting of naphthyl; naphthyl mono- or di-substituted with hydroxy, (C.sub.1 -C.sub.4)alkoxy or (C.sub.1 -C.sub.4)alkyl or naphthyl substituted with methylenedioxy; pyridyl; or (C.sub.1 -C.sub.4)alkyl-pyridyl,and their salts with mineral or organic acids.Type: GrantFiled: June 7, 1995Date of Patent: September 24, 1996Assignee: SanofiInventors: Umberto Guzzi, Costantino Palmieri, Tiziano Croci
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Patent number: 5550236Abstract: A process for preparing polycyclic aromatic compounds by cross-coupling aromatic boronic acids with aromatic halogen compounds or perfluoroalkylsulfonates in the presence of metallic palladium, if desired applied to a support material, as catalyst, wherein the coupling is carried out in the presence of a ligand and a base. The process of the invention allows the yield of polycyclic aromatic compounds to be significantly increased in comparison with processes not using a ligand and thus allows a yield optimum for the Pd(0)-catalyzed cross-coupling of aromatic boronic acids with aromatic halogen compounds to be achieved.Type: GrantFiled: April 24, 1995Date of Patent: August 27, 1996Assignee: Hoechst AktiengesellschaftInventors: Hubert Schlosser, Rainer Wingen, Javier Manero
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Patent number: 5521316Abstract: Provided is a process for preparing chloroalkyl pyridinium hydrochloride compounds and various regioisomers and analogs thereof having substantially high purity levels and yields and a free-flowing, non-dusting form.Type: GrantFiled: May 20, 1994Date of Patent: May 28, 1996Assignee: Cytec Technology Corp.Inventor: William E. Bay
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Patent number: 5484929Abstract: A process for the selective chlorination of pyridine, a lower alkyl pyridine or 3-cyanopyridine includes passing the pyridine compound, chlorine and an inert gas through a two stage reaction. In a first reaction zone, these materials are subjected to a hot spot controlled at a temperature of about 350.degree. to about 500.degree. C. The materials are then subsequently passed through a second reaction zone at a relatively lower temperature, for example below about 340.degree. C.Type: GrantFiled: September 21, 1993Date of Patent: January 16, 1996Assignee: Reilly IndustriesInventor: Joseph E. Toomey
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Patent number: 5484932Abstract: Compounds such as ##STR1## wherein R is F, CF.sub.3, CF.sub.2 H, CHF CF.sub.3 or CF.sub.2 CF.sub.3, as well as related compounds containing chlorine, are used as solvents in halogenation processes.Type: GrantFiled: June 2, 1994Date of Patent: January 16, 1996Assignee: Bayer AktiengesellschaftInventor: Albrecht Marhold
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Patent number: 5482942Abstract: This invention relates to novel 4-(3,4-dioxocyclobuten-1-yl)chromenes and dihydronaphthalenones and 3-(3,4-dioxocyclobuten-1-yl)indenes and salts thereof having smooth muscle relaxing activity, to their use in the treatment of hypertension as well as for treatment of peripheral vascular disease, congestive heart failure, disorders involving excessive smooth muscle contraction of the urinary tract such as incontinence or of the gastrointestinal tract such as irritable bowel syndrome, asthma, and hair loss and to pharmaceutical compositions containing an invention compound. The present invention discloses compounds represented by the formula (I): ##STR1## wherein: R.sub.1 and R.sub.2, independent from each other, are selected from the following: C.sub.1-6 perfluoroalkoxy, C.sub.1-6 perfluoroalkyl, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxyl, C.sub.1-6 alkoxycarbonyl, nitro, cyano, halogen, C.sub.1-6 alkylsulfonamido, C.sub.1-6 perfluoroalkylsulfonamido, amino, C.sub.1-6 acylamino, C.sub.Type: GrantFiled: June 28, 1994Date of Patent: January 9, 1996Assignee: American Home Products CorporationInventors: Richard M. Soll, Paul J. Dollings
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Patent number: 5478497Abstract: Compounds of the formula ##STR1## wherein rings A, B and C, Z.sup.1, Z.sup.2, Z.sup.3, R.sup.1, R.sup.2 and R.sup.3 are defined in the specification, their manufacture, liquid crystalline mixtures which contain such compounds and the use of these compounds for electro-optical purposes.Type: GrantFiled: February 1, 1995Date of Patent: December 26, 1995Assignee: Hoffmann-La Roche Inc.Inventors: Richard Buchecker, Martin Schadt, Alois Villiger
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Patent number: 5475165Abstract: Aryl halide, such as idodobenzene, is reacted with perfluoromethoxycarboxylate, such as CF.sub.3 OCF.sub.2 CO.sub.2 K, in the presence of CuI and an inert aprotic polar solvent to obtain trifluoromethylaryl.Type: GrantFiled: January 18, 1995Date of Patent: December 12, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventors: Keith W. Palmer, Paul R. Resnick
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Patent number: 5475112Abstract: A method for producing a substituted pyridine derivative of the formula (II): ##STR1## wherein each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 is a hydrogen atom, a halogen atom or an alkyl group, and m is an integer of from 1 to 3, which comprises reducing a substituted trichloromethylpyridine derivative of the formula (I): ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined above, with use of acetic acid, hydrochloric acid or sulfuric acid, as a proton donor, and zinc, tin or a mixture thereof, as a reducing agent.Type: GrantFiled: October 4, 1994Date of Patent: December 12, 1995Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Takao Awazu, Hiroshi Okada, Masamitsu Matsumoto
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Patent number: 5462945Abstract: New N-substituted 4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridines useful in the treatment of intestinal motility disorders, of the following general formula ##STR1## wherein A represents a group --E--G or --L--M, where--E-- is a straight or branched alkylene radical of from 2 to 4 carbon atoms,--G represents a radical selected from the group consisting of naphthyl mono-substituted with hydroxy or (C.sub.1 -C.sub.4)alkoxy; naphthyl di-substituted with hydroxy, (C.sub.1 -C.sub.4)alkoxy or (C.sub.1 -C.sub.4)alkyl; or naphthyl substituted with methylenedioxy,--L-- is a --Q--CH(OH)-- group wherein --Q-- is a straight or branched alkylene radical of from 1 to 3 carbon atoms, and--M represents a radical selected from the group consisting of naphthyl; naphthyl mono- or di-substituted with hydroxy, (C.sub.1 -C.sub.4)alkoxy or (C.sub.1 -C.sub.4)alkyl or naphthyl substituted with methylenedioxy; pyridyl; or (C.sub.1 -C.sub.4)alkyl-pyridyl,and their salts with mineral or organic acids.Type: GrantFiled: October 26, 1993Date of Patent: October 31, 1995Assignee: SanofiInventors: Umberto Guzzi, Costantino Palmieri, Tiziano Croci
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Patent number: 5453218Abstract: This invention provides chiral nonracemic compounds of formula ##STR1## wherein * indicates a chiral carbon, R.sub.1 and R.sub.2, independently of one another, can be an alkyl, alkenyl or alkynyl group wherein one or more non-neighboring CH.sub.2 groups can be replaced with an O, S or a silyl group (R.sub.A SiR.sub.B) wherein R.sub.A and R.sub.B, independently of one another, are alkyl or alkenyl having from one to six carbon atoms; R.sub.1 having from about 3 to 20 carbon atoms, and R.sub.2 having from 1 to about 18 carbon atoms; X is O, S, CO, COO, OCO, COS or a single bond where Ar is a liquid crystal core moiety having two or three aromatic rings of the formula--(Cyc).sub.n --(A).sub.a --Ph.sub.1 --(B).sub.b --Ph.sub.2 --(C).sub.c --(Ph.sub.3).sub.m --whereinPh.sub.1, Ph.sub.2 and Ph.sub.Type: GrantFiled: February 8, 1994Date of Patent: September 26, 1995Assignee: Displaytech, Inc.Inventors: Michael D. Wand, Kundalika M. More, William N. Thurmes
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Patent number: 5447657Abstract: The present invention provides compounds of the general formula: ##STR1## wherein R is an alkyl group with 1 to 12 carbon atoms or a group of the formula ##STR2## Ring A.sup.1 is 1,4-phenylene, which is unsubstituted or substituted with fluorine, pyridine-2,5-diyl or pyrimidine-2,5-diyl;Ring A.sup.2 is trans-1,4-cyclohexylene or trans-1,3-dioxane-2,5-diyl;R.sup.1 is an alkyl, alkenyl or alkoxyalkyl group with 1 to 12 and, respectively, 2 to 12 carbon atoms;X.sup.1 is fluorine, chlorine, bromine, trifluoromethyl, trifluoromethoxy or difluoromethoxy; andX.sup.2, X.sup.3 each independently are hydrogen or fluorine.The invention is also concerned with liquid crystal mixtures which contain these compounds and with the use of these compounds and mixtures for electro-optical purposes.Type: GrantFiled: March 8, 1994Date of Patent: September 5, 1995Assignee: Hoffmann-La Roche Inc.Inventors: Martin Schadt, Alois Villiger
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Patent number: 5446134Abstract: Bis(perfluorosulphonyl)methanes, process for preparing same and uses thereof. The compounds of the invention are based on the formula (1/nM)+[(R.sub.F SO.sub.2).sub.2 CY].sup.- in which Y denotes an electron-attracting group chosen from --C.dbd.N and RZ groupings in which Z denotes a carbonyl grouping, sulphonyl grouping or a phosphonyl grouping and R denotes an organic monovalent grouping, M denotes a metal having valency n or an organic group capable of existing in the cationic form, R.sub.F denotes a perfluoroalkyl or perfluoroaryl grouping. Said compounds are especially useful in the production of electrochemical devices.Type: GrantFiled: July 8, 1993Date of Patent: August 29, 1995Assignees: Centre National de la Recherche Scientifique, Hydro QuebecInventors: Michel Armand, Djamila Benrabah, Jean-Yves Sanchez
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Patent number: 5442072Abstract: The invention relates to a novel process for preparing chloromethylpyridines of the general formula (I) ##STR1## in which n represents the numbers 0,1,2 or 3 andX represents halogen,by reacting aminomethylpyridines of the general formula (II) ##STR2## with a nitrosating or diazotizing agent in the presence of a diluent and optionally in the presence of hydrogen chloride at temperatures between -20.degree. C. and +50.degree. C. and then working up in a conventional manner.Type: GrantFiled: June 24, 1994Date of Patent: August 15, 1995Assignee: Bayer AktiengesellschaftInventors: Helmut Kraus, Hans Lindel, Hans-Joachim Diehr
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Ferroelectric liquid crystal compounds containing halogenated cores and chiral haloalkoxy tail units
Patent number: 5422037Abstract: The subject application discloses chiral nonracemic compositions of the general formula: ##STR1## wherein R.sub.1 is an achiral tail of two to sixteen carbons; Ar is an achiral FLC core of at least two rings; * denotes a chiral or potentially chiral carbon; Q and D are H or a methyl group, provided that q and D are not both methyl; X and Z are halides and Y is H or a halide; and R.sub.2 is one to ten carbon atoms. The --O--C*HQ--C*DX--C*HY-- segment comprises the chiral proximal segment of the chiral tail. Z can be an ortho halide alone, or ortho and meta halides on adjacent carbons on the aromatic ring of the core adjacent to the proximal segment. R.sub.2 is the distal segment of the chiral tail.Type: GrantFiled: January 19, 1993Date of Patent: June 6, 1995Assignee: Displaytech, Inc.Inventors: Michael Wand, Rohini Vohra, David Walba -
Patent number: 5356563Abstract: Optically active compounds of the formula ##STR1## wherein m stands for the number 1 and R.sup.2 is an unsubstituted or halogen-substituted alkyl or alkenyl group in which optionally one methylene group is replaced by oxygen and/or optionally one methylene group is replaced by an ester group --COO-- or --OOC--; or m stands for the number 0 or 1 and R.sup.2 denotes a group of the formula ##STR2## R.sup.1 and R.sup.3 each independently represent an alkyl or alkenyl group in which optionally one methylene group is replaced by oxygen; Z.sup.1, Z.sup.2 and Z.sup.3 each independently are a single covalent bond, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --COO-- or --OOC--; n stands for the number 0 or 1; rings A.sup.1 and A.sup.2 each independently are unsubstituted or halogen, cyano and/or methyl-substituted 1,4-phenylene in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen; and C.sup.* denotes a chiral carbon atom; with the proviso that simultaneously R.sup.Type: GrantFiled: June 9, 1993Date of Patent: October 18, 1994Assignee: Hoffmann-La Roche Inc.Inventors: Richard Buchecker, Stephen Kelly, Frans Leenhouts
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Patent number: 5352822Abstract: The present invention discloses pesticidally active compounds of formula (II) ##STR1## or a salt thereof, wherein Q is an monocyclic aromatic ring, or fused bicyclic ring system of which at least one ring is aromatic containing 9 or 10 atoms of which one may be nitrogen and the rest carbon each ring system being optionally substituted, or Q is a dihalovinyl group or a group R.sup.6 --C.tbd.C-- where R.sup.6 is C.sub.1-4 alkyl, tri C.sub.1-4 alkylsilyl, halogen or hydrogen; R.sup.2, R.sup.3 , R.sup.4 and R.sup.5 are the same or different with at least one being hydrogen and the others being independently selected from hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 haloalkyl; and R.sup.1 is selected from hydrogen and C.sub.1-8 hydrocarbyl optionally substituted by dioxalanyl, halo, cyano, trifluoromethyl, trifluoromethylthio or C.sub.1-6 alkoxy and X.sup.1 is hydrogen, fluoro or chloro.Type: GrantFiled: April 7, 1993Date of Patent: October 4, 1994Assignee: Roussel UclafInventors: Robert J. Blade, George S. Cockerill, John E. Robinson
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Patent number: 5329011Abstract: A process for the preparation of a 2-chloro-5-chloro-methyl-pyridine, of the formula (I) ##STR1## comprising reacting a 2-alkoxy-5-alkoxymethylpyridine derivative of the formula (II) ##STR2## in which R.sup.1 represents alkyl, with a chlorinating agent, if appropriate, in the presence of a diluent and if appropriate, in the presence of a reaction auxiliary, at a temperature between 0.degree.C. and 200.degree.C.Type: GrantFiled: June 7, 1993Date of Patent: July 12, 1994Assignee: Bayer AktiengesellschaftInventor: Klaus Jelich
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Patent number: 5326902Abstract: Oxyalkyne compounds corresponding to the formula I ##STR1## in which the substituent Y in the meta- or para-position is R.sup.1 represents CH.sub.3 or NH.sub.2, R.sup.2 represents H or CH.sub.3, R.sup.3 represents H, C.sub.1-3 -alkyl or COCH.sub.3, and Ar represents an aromatic residue selected from the group ##STR2## with the proviso that the substituents R.sup.4, R.sup.5 and R.sup.6 are the same or different and each substituent represents H, F, Cl, Br, C.sub.1-6 -alkyl, CF.sub.3 or C.sub.1-6 -alkoxy, and R.sup.7 represents H, F, Cl, Br, C.sub.1-3 -alkyl or CF.sub.3,in the form of their racemates or mixtures of diastereoisomers or in optically active form, which are suitable active ingredients in pharmaceutical compositions.Type: GrantFiled: March 24, 1993Date of Patent: July 5, 1994Assignee: Gruenenthal GmbHInventors: Ulrich Seipp, Werner Vollenberg, Werner Englberger, Cornelia Geist, Michael Haurand
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Patent number: 5324841Abstract: The invention relates to a method of chlorinating a side chain methyl group of 2-chloro-methylpyridine. The method comprising the steps of:(a) reacting said 2-chloro-methylpyridine with chlorine radical so that hydrogen chloride and/or hydrochloride of 2-chloro-methylpyridine are formed; and (b) neutralizing said hydrogen chloride and/or said hydrochloride of said 2-chloro-methyl-pyridine with a basic solution so as to chlorinating a side chain methyl group of said 2-chloro-methylpyridine.Type: GrantFiled: February 24, 1993Date of Patent: June 28, 1994Assignee: Central Glass CompanyInventors: Yasunobu Nishimura, Yukikazu Itou, Asao Morino, Katuya Nishihara, Shinya Kawamura
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Patent number: 5319088Abstract: 2,3,5,6-Tetrachloropyridine, and 2,3-dichloro-5-(trichloromethyl)pyridine are prepared by selectively chlorinating polychlorinated .beta.-picolines in the vapor phase between about 250.degree. and 450.degree. C. in the presence of specific Lewis acid halide catalysts on an inorganic support. The gamma position on the pyridine ring is usually not chlorinated in the starting material or reaction products. These compounds are useful intermediates to produce insecticides and herbicides.Type: GrantFiled: November 26, 1991Date of Patent: June 7, 1994Assignee: DowElancoInventors: Clark P. Allphin, Michael A. DesJardin, Arnold D. Harley
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Patent number: 5313001Abstract: Process for the preparation of .alpha.-fluorostyrene from fluoroolefins: ##STR1## Z=hydrogen, fluorine, chlorine X=iodine, bromine, chlorine.A halogenated aromatic (I) is reacted with a fluorine-substituted ethylene (II) in the presence of a palladium catalyst to give an .alpha.-fluorostyrene (III), it being possible for R to be a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.4 -alkyl group, a C.sub.1 -C.sub.5 -alkoxy group, an amino, alkylamino or dialkylamino group, an aryl radical or a fused aryl or heteroaryl ring, a hydroxyl or hydroxyalkyl group, a trifluoromethyl or perfluoroalkyl group or a nitro group.Type: GrantFiled: November 17, 1992Date of Patent: May 17, 1994Assignee: Hoechst AktiengesellschaftInventors: Walter Heitz, Arno Knebelkamp
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Use of 4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine derivatives as free radical scavengers
Patent number: 5292745Abstract: The invention concerns the use of a compound of formula (I) ##STR1## wherein R and R.sub.1, each independently, represent a hydrogen atom or a methyl group, and its pharmaceutically acceptable acid addition salts, as free radical scavengers. The pharmaceutical compositions containing these compounds may be employed in the treatment and/or prevention of pathological processes involving cell damage due to the formation of free radicals.The invention also concerns the compounds of formula (I) wherein at least one of R and R.sub.1 is methyl, which are new compounds, as well as the process for the preparation thereof and the pharmaceutical compositions containing them.Type: GrantFiled: February 4, 1992Date of Patent: March 8, 1994Assignee: Elf SanofiInventors: Michel Heaulme, Umberto Guzzi -
Patent number: 5292761Abstract: The invention relates to compounds of formula I: ##STR1## in which R.sub.1 represents a naphthyl radical, a dihydronaphthyl radical, a tetrahydronaphthyl radical, a quinolyl radical or a 1,4-benzodioxanyl radical, A represents a single bond, a double bond, a methylene radical, a radical of formula z.sub.1 :--CH.dbd. (z.sub.1)or a radical of formula z.sub.2 :.dbd.Ch-- (z.sub.2)the ring B represents a piperidyl radical, a pyrrolidinyl radical, or a 1,2,3,6-tetrahydropyridyl radical, and R.sub.2 represents: a hydrogen atom, a benzyl radical, or an alkyl radical having 1 to 6 carbon atoms, on condition that in one of these cases R.sub.1 is other than a naphthyl (y.sub.1), dihydronaphthyl (y.sub.2) or tetrahydronaphthyl (y.sub.3) radical and B is other than a piperidinyl radical, or an aminoalkyl radical having 1 to 6 carbon atoms, a cyanoalkyl radical having 1 to 6 carbon atoms, or a radical of formula w.sub.1 : ##STR2## in which n is 1-6 and R.sub.Type: GrantFiled: November 5, 1992Date of Patent: March 8, 1994Assignee: Adir et CompagnieInventors: Gilbert Lavielle, Michel Laubie, Francis Colpaert
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Patent number: 5292452Abstract: Compounds of the formula ##STR1## wherein Z.sup.1 denotes a single covalent bond or --CH.sub.2 Ch.sub.2 --; ring A.sup.1 represents 1,4-phenylene, pyrimidine-2,5-diyl, pyridine-2,5-diyl or, when Z.sup.1 stands for --CH.sub.2 CH.sub.2 --, also trans-1,4-cyclohexylene; X.sup.1 stands for fluorine or chlorine; X.sup.2 signifies fluorine, chlorine or hydrogen, with the proviso that X.sup.2 only signifies hydrogen when X.sup.1 is chlorine or when ring A.sup.1 signifies pyridine-2,5-diyl and Z.sup.1 signifies --CH.sub.2 CH.sub.2 --; and R.sup.1 signifies 1E-alkenyl with 2 to 12 carbon atoms,their manufacture, liquid crystalline mixtures which contain these compounds and their use for electro-optical purposes.Type: GrantFiled: August 19, 1991Date of Patent: March 8, 1994Assignee: Hoffmann-La Roche Inc.Inventors: Richard Buchecker, Alfred Germann, Martin Schadt, Alois Villiger
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Patent number: 5290944Abstract: A method for producing a dichloromethylpyridine of the formula (II): ##STR1## wherein each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 which are independent of one another, is a hydrogen atom, a halogen atom, an alkoxy group or a phenoxy group which may be substituted, provided that R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are not simultaneously hydrogen atoms, which comprises reacting a trichloromethylpyridine of the formula (I): ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined above, with a reducing agent, wherein:(1) a dialkyl phosphite or a trialkyl phosphite is used as the reducing agent, and the reaction is conducted in the presence of a basic substance and an alcohol solvent, or(2) a trialkyl phosphine or triphenyl phosphine is used as the reducing agent, and the reaction is conducted in the presence of an alcohol solvent.Type: GrantFiled: December 14, 1992Date of Patent: March 1, 1994Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Rikuo Nasu, Taku Shimura, Isamu Katsuyama
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Patent number: 5284599Abstract: A mesomorphic compound represented by the following formula (I):R.sub.1 --A.sub.1 --B.sub.1 --A.sub.2 --R.sub.2 (I),wherein R.sub.1 and R.sub.2 respectively denote a linear or branched alkyl group having 3-18 carbon atoms capable of including one or non-neighboring two or more methylene groups which can be replaced with at least one species of --Z--, ##STR1## CH.dbd.CH-- and --C.tbd.C--, wherein Z denotes --O-- or --S-- and R.sub.3 denotes hydrogen or an alkyl group having 1-5 carbon atoms; B.sub.1 denotes ##STR2## A.sub.1 denotes a single bond, ##STR3## A.sub.2 denotes a single bond, --A.sub.3 -- or --A.sub.3 --A.sub.4 -- wherein A.sub.3 and A.sub.4 respectively denote any one of ##STR4## and Y.sub.1 and Y.sub.2 respectively denote any one of hydrogen, fluorine, chlorine, bromine, --CH.sub.3, --CN and --CF.sub.3.Type: GrantFiled: July 20, 1992Date of Patent: February 8, 1994Assignee: Canon Kabushiki KaishaInventors: Takashi Iwaki, Takao Takiguchi, Takeshi Togano, Yoko Yamada, Shinichi Nakamura
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Patent number: 5284956Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is alkyl or trans-4-alkylcyclohexyl andR.sup.2 is alkyl, alkoxy or trans-4-alkylcyclohexyl their preparation, liquid crystalline mixtures containing these compounds and their use for electro-optical purposes.Type: GrantFiled: March 25, 1992Date of Patent: February 8, 1994Assignees: Hoffmann-La Roche Inc., Niopic Moscow Research and Production AssociationInventors: Richard Buchecker, Assya I. Pavluchenko, Vladimir F. Petrov, Martin Schadt, Natalia I. Smirnova, Victor V. Titov
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Patent number: 5283338Abstract: 2-Chloropyridine derivatives of the formula (I) ##STR1## in which R represents hydrogen, C.sub.1 -C.sub.4 -alkyl or halogen andn represents 0 to 4,are obtained in good yields and high purity when a 2-aminopyridine derivative of the formula (II) ##STR2## in which R and n have the above definitions,is reacted with nitrosyl chloride in a hydrogen chloride-saturated aqueous solution at temperatures between -10.degree. C. and +50.degree. C. with simultaneous introduction of hydrogen chloride.Type: GrantFiled: April 1, 1992Date of Patent: February 1, 1994Assignee: Bayer AktiengesellschaftInventors: Gunther Cramm, Hans Lindel, Guido Steffan
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Patent number: 5266573Abstract: A method of prophylaxis and/or treatment of intestinal motility disorders, in particular of constipation, in mammals which comprises administering to a mammal in need of such a treatment a prophylactically and/or therapeutically effective amount of a compound of formula (I) ##STR1## wherein Alk represents a straight or branched (C.sub.1 -C.sub.4)alkylene radical, andR represents a cyano, acetyl, (C.sub.3 -C.sub.7)cycloalkyl, phenyl, p-tolyl, pyridyl, pyridyl 1-oxide, or naphthyl group, or of a pharmaceutically acceptable salt thereof.Type: GrantFiled: March 29, 1993Date of Patent: November 30, 1993Assignee: Elf SanofiInventors: Tiziano Croci, Alberto Bianchetti, Luciano Manara
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Patent number: 5262420Abstract: A pyridine compound of the formula ##STR1## wherein X is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms or a haloalkoxyl group having 1 to 4 carbon atoms, n is 1 to 5, and when n is 2 or more, Xs may be identical to or different from each other, A is an alkyl residue or alkene residue in which a portion connecting the aryl group with the 4-position of the pyridyl group has 3 to 8 carbon atoms, or an alkapolyene residue in which said portion has 4 to 8 carbon atoms and 2 to 4 double bonds; the alkyl residue, alkene residue, and alkapolyene residue may have an alkyl side chain having 1 to 4 carbon atoms, an alkylidene side chain having 1 to 4 carbon atoms or 1 to 16 halogen atoms, and when there are 2 or more side chains, the side chains may be identical to or different from each other, and R.sup.1 and R.sup.Type: GrantFiled: May 21, 1992Date of Patent: November 16, 1993Assignee: Idemitsu Kosan Co., Ltd.Inventors: Izumi Terada, Katsuhiko Matsuzaki, Kazuyoshi Nonoshita, Fumio Fujita
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Patent number: 5247093Abstract: A process for the selective chlorination of pyridine or a lower alkyl pyridine includes passing the pyridine compound, chlorine and an inert gas through a two stage reaction. In a first reaction zone, these materials are subjected to a hot spot controlled at a temperature of about 350.degree. to about 500.degree. C. The materials are then subsequently passed through a second reaction zone at a relatively lower temperature, for example below about 340.degree. C.Type: GrantFiled: December 15, 1992Date of Patent: September 21, 1993Assignee: Reilly Industries, Inc.Inventor: Joseph E. Toomey
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Patent number: 5244597Abstract: Optically active compounds of the formula ##STR1## wherein m stands for the number 1 and R.sup.2 is an unsubstituted or halogen-substituted alkyl or alkenyl group in which optionally one methylene group is replaced by oxygen and/or optionally one methylene group is replaced by an ester group --COO-- or --OOC--; or m stands for the number 0 or 1 and R.sup.2 denotes a group of the formula ##STR2## R.sup.1 and R.sup.3 each independently represent an alkyl or alkenyl group in which optionally one methylene group is replaced by oxygen; Z.sup.1, Z.sup.2 and Z.sup.3 each independently are a single covalent bond, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --COO-- or --OOC--; n stands for the number 0 or 1; rings A.sup.1 an A.sup.2 each independently are unsubstituted or halogen, cyano and/or methyl-substituted 1,4-phenylene in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen; and C* denotes a chiral carbon atom; with the proviso that simultaneously R.sup.Type: GrantFiled: June 11, 1992Date of Patent: September 14, 1993Assignee: Hoffmann-La Roche Inc.Inventors: Richard Buchecker, Stephen Kelly, Frans Leenhouts
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Patent number: 5233043Abstract: A process for the preparation of a 2-alkoxy-5-alkoxymethylpyridine derivative of the formula (II) ##STR1## in which R.sup.1 represents alkyl, comprising reacting a 3-dichloromethylpyridine, of the formula III, ##STR2## with an alcohol of the formula R.sup.1 --OH (IV) and with the corresponding alkali metal alkoxide of this alcohol, at a temperature between 0.degree. C. and 150.degree. C.Type: GrantFiled: December 2, 1991Date of Patent: August 3, 1993Assignee: Bayer AktiengesellschaftInventor: Klaus Jelich
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Patent number: 5225607Abstract: This invention relates to novel fluorinated ethers, useful as insecticides and acaricides, to processes and intermediates for their preparation, to insecticidal and acaricidal compositions thereof and to methods of combating and controlling insect and acarine pests therewith.Type: GrantFiled: December 30, 1987Date of Patent: July 6, 1993Assignee: Imperial Chemical Industries PLCInventors: Michael J. Bushell, Robin A. E. Carr, Alan J. Whittle
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Patent number: 5204476Abstract: The invention relates to fluorophenylpyridines of the formula I: ##STR1## where R.sup.1 and R.sup.2 are substituted and unsubstituted monovalent organic radicals.Type: GrantFiled: December 18, 1990Date of Patent: April 20, 1993Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Andreas Wachtler, Eike Poetsch, Thomas Geelhaar, Reinhard Hittich, Volker Reiffenrath, Hans-Michael Kompter
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Patent number: 5198549Abstract: In the chlorination of the side chain of an alkylated nitrogen heteroaromatic such as pyridine or pyrimidine by reaction with elemental chlorine, the reaction is effected in acetronitrile as solvent.Type: GrantFiled: May 13, 1991Date of Patent: March 30, 1993Assignee: Bayer AktiengesellschaftInventor: Andreas Gunther
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Patent number: 5194619Abstract: The compounds of the formula I or Ia ##STR1## in which R.sup.1 is alkyl, aryl, alkoxy, alkenyl, arylalkyl, alkylaryl, aryloxy, fluoroalkyl, halogenoaryl, alkynyl, trialkylsilyl or a heteroaromatic radical,R.sup.2, R.sup.3 and R.sup.4, in addition to hydrogen, have the meanings given under R.sup.1 andR.sup.5 is hydrogen, alkyl, fluoroalkyl or alkenyl, can be obtained in a one-stage process by reaction of a compound II ##STR2## with (substituted) cyclopentadiene in the presence of a base. The compounds I and Ia are suitable as ligands for metallocene complexes which are used as catalysts in olefin polymerization.Type: GrantFiled: February 14, 1992Date of Patent: March 16, 1993Assignee: Hoechst AktiengesellschaftInventors: Dieter Reuschling, Jurgen Rohrmann, Gerhard Erker, Reiner Nolte, Michael Aulbach, Astrid Weiss
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Patent number: 5180520Abstract: The subject application discloses chiral nonracemic compositions of the general formula: ##STR1## wherein R.sub.1 is an achiral tail of two to sixteen carbons; Ar is an achiral FLC core of at least two rings; * denotes a chiral or potentially chiral carbon; Q is H or a methyl group; X and Z are halides and Y is H or a halide; and R.sub.2 is one to ten carbon atoms. The --O--C*HQ--C*HX--C*HY-- segment comprises the chiral proximal segment of the chiral tail. Z can be an ortho halide alone, or ortho and meta halides on adjacent carbons on the aromatic ring of the core adjacent to the proximal segment. R.sub.2 is the distal segment of the chiral tail.Type: GrantFiled: July 20, 1990Date of Patent: January 19, 1993Assignee: University Research CorporationInventors: Michael Wand, Rohini Vohra, David Walba
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Patent number: 5175167Abstract: Hetarylalkenes of the general formula I ##STR1## where Ar is hetaryl,A is C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.3 -C.sub.8 -cycloalkyl-C.sub.1 -C.sub.3 -alkyl or unsubstituted or monosubstituted, disubstituted or trisubstituted aryl or aralkyl, ##STR2## Z is whereR is hydrogen, C.sub.2 -C.sub.4 -acyl, unsubstituted or substituted benzoyl, C.sub.1 -C.sub.4 -alkylsulfonyl, unsubstituted or C.sub.1 -C.sub.4 -alkyl-substituted phenylsulfonyl or a radical R.sup.1,R.sup.1 is C.sub.1 -C.sub.4 -alkyl or unsubstituted or substituted phenyl or benzyland Hal is fluorine, chlorine, bromine or iodine,and B is unsubstituted or substituted mononuclear or dinuclear aryl, aralkyl or hetaryl,and their N-oxides and addition salts, the preparation of these substances, intermediates for this purpose and the preparation thereof, fungicides containing hetarylalkenes and a corresponding method for controlling harmful fungi.Type: GrantFiled: February 8, 1991Date of Patent: December 29, 1992Assignee: BASF AktiengesellschaftInventors: Bernhard Zipperer, Manfred Lauer, Norbert Goetz, Thomas Zierke, Eberhard Ammermann, Gisela Lorenz
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Patent number: 5167855Abstract: The subject application discloses chiral nonracemic compositions of the general formula:R.sub.1 --(Ar)--O--C*H(CH.sub.3)--C*HX--C*HY--R.sub.2wherein: R.sub.1 is an achiral tail of two to sixteen carbons; Ar is an achiral FLC core of at least two rings; * denotes a chiral or potentially chiral carbon; X is a halide and Y is H or a halide; R.sub.2 comprises the distal segment of the chiral tail and has one to ten carbon atoms; the --O--C*H(CH.sub.3)--C*HY--C*HY--CH.sub.2 --O-- segment comprises the chiral proximal segment of the chiral tail, and the proximal segment is selected from the diastereomers and enantiomers:1S-methyl-2S-halo1S-methyl-2R-halo1R-methyl-2R,3R-dihalo1R-methyl-2R,3S-dihalo1R-methyl-2S,3S-dihalo1R-methyl-2S,3R-dihalo1R-methyl-2R-halo1R-methyl-2S-halo1S-methyl-2S,3S-dihalo1S-methyl-2S,3R-dihalo1S-methyl-2R,3R-dihalo1S-methyl-2R,3S-dihalo.Type: GrantFiled: July 20, 1990Date of Patent: December 1, 1992Assignee: University Research CorporationInventors: Michael Wand, Rohini Vohra, David Walba
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Patent number: 5162329Abstract: .beta.-picoline derivatives of the formula ##STR1## where A is CR.sup.1 R.sup.2, R.sup.1 and R.sup.2 independently of each other are hydrogen, alkyl, alkenyl or alkynyl, or R.sup.1 and R.sup.2 together form a methylene chain,B is one of the groups CH.sub.2, CHOR.sup.3, CHalR.sup.4, C.dbd.O or C.dbd.N-O-R.sup.5, R.sup.3 being hydrogen, alkyl, haloalkyl, cycloalkyl, alkenyl, acyl, phenyl, benzyl or benzoyl, where the phenyl ring is substituted or unsubstituted, R.sup.4 being hydrogen, fluorine, chlorine, bromine or iodine, R.sup.5 being hydrogen, alkyl, haloalkyl, cycloalkyl, alkenyl, phenyl or benzyl, the phenyl ring being substituted or unsubstituted,Ar is a substituted or unsubstituted aryl radical,their N-oxides and plant-tolerated acid addition salts, and fungicides containing these compounds.Type: GrantFiled: May 23, 1991Date of Patent: November 10, 1992Assignee: BASF AktiengesellschaftInventors: Oliver Wagner, Bernhard Zipperer, Norbert Goetz, Michael Keil, Eberhard Ammermann, Gisela Lorenz
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Patent number: 5160662Abstract: Optically active compounds having the following formulae (1), (2) or (3) ##STR1## wherein R and R' are C.sub.1-20 alkyl groups; X and Y.sub.1 are --, O, S, or divalent groups such as COO, OOC and OCOO; m is 0 or 1; n is 0 to 5; A.sub.2 is a cyclic group, such as p,p'-biphenylene, 2,6-naphthylene, 2,5-pyrimidinylene-1,4-phenylene, A.sub.1 -Y.sub.2 -pyridylene or A.sub.4 -Y.sub.2 -A.sub.5 ; Y.sub.2 is CH.sub.2 CH.sub.2 or C.tbd.C; A.sub.3 is 2,6-naphthylene, A.sub.1 -Y.sub.2 -pyridylene or A.sub.6 -CH.sub.2 CH.sub.2 -A.sub.7 ; and A.sub.1, A.sub.4, A.sub.5, A.sub.6 and A.sub.7 are cyclic groups, such as 1,4-phenylene and/or 4,4'-biphenylene.Type: GrantFiled: February 27, 1990Date of Patent: November 3, 1992Assignee: Sanyo Chemical Industries, Ltd.Inventors: Masahiro Satoh, Tetsuya Watanabe, Kunikiyo Yoshio, Hiroshi Kishiki
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Patent number: 5151428Abstract: A pyridine derivative of the formula: ##STR1## wherein R.sup.1 is, the same or different, each a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.3 alkoxy gorup, a C.sub.1 -C.sub.3 haloalkoxy group, a cyano group or a nitro group; R.sup.2 is, the same or different, each a hydrogen atom, a halogen atom or a methyl group; R.sup.3 is a halogen atom or a C.sub.1 -C.sub.3 alkyl group; R.sub.4 is a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group; R.sup.5 is, the same or different, each a halogen atom, a C.sub.1 -C.sub.3 alkyl group, a C.sub.1 -C.sub.3 haloalkyl group, a C.sub.1 -C.sub.3 alkoxy group or a C.sub.1 -C.sub.3 haloalkoxy group; X is an oxygen atom, a sulfur atom, a carbonyl group, a sulfinyl group, a sulfonyl group, an imino group or a methylene group; Y is an oxygen atom or a sulfur atom; l is an integer of 1 to 5; m is an integer of 1 to 3; and n is an integer of 1 to 4, which is useful for control of insect pest.Type: GrantFiled: May 24, 1991Date of Patent: September 29, 1992Inventors: Noriyasu Sakamoto, Hirosi Kisida, Hiroaki Fujimoto, Kimitoshi Umeda, Noritada Matsuo
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Patent number: 5137923Abstract: Lipophilic quaternary ammonium salicylate, characterized in that it corresponds to the formula: ##STR1## in which: (i) R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be identical or different, denote an alkyl or alkylcycloalkyl radical, optionally substituted or interrupted;(ii) R.sub.3 and/or R.sub.4 denote(s) a group:R.sub.8 --OC.sub.2 H.sub.3 R.sub.7 ].sub.n [OCH.sub.2 CHOH--CH.sub.2 ].sub.pin which: 0.ltoreq.n.ltoreq.4 and p denotes 0 or 1; R.sub.8 denotes H or an alkyl, alkenyl, alkylcycloalkyl or alkylaryl radical;(iii) R.sub.4 denotes an alkylphenyl radical;(iv), (v) R.sub.1 and R.sub.2 can form a saturated or unsaturated aromatic or non-aromatic heterocycle;(vi) R.sub.1, R.sub.2 and R.sub.3 form polycyclic derivatives with the nitrogen atoms; R.sub.5 denotes a group corresponding to the formula: ##STR2## in which n is an integer varying between 0 and 10.Type: GrantFiled: June 21, 1990Date of Patent: August 11, 1992Assignee: L'OrealInventors: Michel Philippe, Henri Sebag, Michel Hocquaux, Bernard Jacquet, Jean P. Laugier
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Patent number: RE35177Abstract: A pyridine-compound is reacted with fluorine together with a .[.Bronsted.]. .Iadd.Bronsted .Iaddend.acid-compound or Lewis acid to form a N-fluoropyridinium salt which is very active to other compounds but is very selective for the preparation of a desired product and this product is very useful for a fluorine-introducing agent which makes it useful for the preparation of fluoro-compounds such as thyroid inhibitor.Type: GrantFiled: February 17, 1994Date of Patent: March 12, 1996Assignees: Sagami Chemical Research Center, Chichibu Onoda Cement CorporationInventors: Teruo Umemoto, Kyoichi Tomita, Kosuke Kawada, Ginjiro Tomizawa