Halogen Containing Patents (Class 568/634)
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Patent number: 4853151Abstract: Dispirotetradecanes of the formula I ##STR1## wherein R.sup.1 and R.sup.2 are each independently of each other alkyl containing 1 to 12 carbon atoms wherein one or more non-adjacent CH.sub.2 groups may also be replaced by --O--, --CO--, --CO--O--, --O--CO--, --O--COO-- and/or --CH.dbd.CH-- (trans), one of the radicals R.sup.1 and R.sup.2 also being H, F, Cl, Br, I, CN, NO.sub.2, NCS,A.sup.1 and A.sup.2 are each independently of each other trans-1,4-cyclohexylene wherein one or two non-adjacent CH.sub.2 groups may be replaced by --O-- and/or --S--, or 1,4-phenylene wherein one or more CH groups may also be replaced by N, with it also being possible optionally for A.sup.1 and A.sup.2 to be substituted laterally or axially by F, Cl, CN, CH.sub.3,Z.sup.1 and Z.sup.2 are each independently of each other --C--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 -- or a single bond,m and n are each 0, 1 or 2,(m+n) 0, 1 or 2,X.sup.1, X.sup.2, X.sup.3 and X.sup.Type: GrantFiled: August 11, 1987Date of Patent: August 1, 1989Assignee: Merck Patent Gesellschaft Mit Beschrankfter HaftungInventors: Fritz Vogtle, Wolfgang Calaminus
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Patent number: 4846998Abstract: Cyclohexane derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 Iin whichR.sup.1 and R.sup.2 are each an alkyl group having 1-10 C atoms, in which one or two non-adjacent CH.sub.2 groups can also be replaced by O atoms and/or --CO-- groups and/or --CO--O-- groups and/or --CH.dbd.CH-- groups, one of the radicals R.sup.1 and R.sup.2 also being H, F, Cl, Br, CN or R.sup.3 --A.sup.3 --Z.sup.2 --,A.sup.1 is --A--, A.sup.4 --A-- or --A--A.sup.4 --,A is a trans-1,4-cyclohexylene group which can be substituted in the 2-, 3-, 5- and/or 6-position one or more times by F and/or Cl and/or Br and/or CN and/or an alkyl group or a fluorinated alkyl group which each have 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-- groups and/or --CO--O-- groups, and which may also be substituted in the 1- and/or 4-position,A.sup.2, A.sup.3 and A.sup.Type: GrantFiled: November 21, 1986Date of Patent: July 11, 1989Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Ludwig Pohl, Bernhard Scheuble, Reinhard Hittich, Rudolf Eidenschink, Hans A. Kurmeier, Andreas Wachtler
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Patent number: 4824920Abstract: The resins resulting from converting dicyclopentadiene-phenol adducts to their corresponding vinylbenzyl ethers are an excellent matrix in which to embed fibers to produce a composite. Such resins, especially as a blend of materials with varying molecular weight distribution, are amorphous materials whose glass transition temperature is well under the curing temperature, and whose solubility permits solutions with high solids content so as to afford coatings with high resin content. The extensively crosslinked polymer resulting from therma, photochemical, or free radical initiated polymerization has excellent thermal and electrical properties for use in multilayer circuit boards.Type: GrantFiled: November 30, 1987Date of Patent: April 25, 1989Assignee: Allied-Signal Inc.Inventors: Joseph J. Zupancic, Jeffrey P. Conrad, James A. Wrezel, Andrew M. Zweig, Jean M. J. Frechet
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Patent number: 4791139Abstract: A compound of formula: ##STR1## wherein W represents one or more substituents selected from halo, alkyl, alkoxy, alkoxyalkyl, haloalkyl and haloalkoxy or W represents a bidentate group linking adjacent carbon atoms selected from alkylene and alkylenedioxy; Y is a group of formula ##STR2## wherein X is a group of formula --(CF.sub.2).sub.n R.sup.3, where R.sup.3 is selected from hydrogen, chloro and fluoro, and n is one or two, R.sup.1 is selected from hydrogen, chloro, fluoro and hydroxy and R.sup.2 is selected from methyl, cyano, ethynyl and hydrogen; Q is selected from carbon bearing a hydrogen atom and nitrogen; and Z represents one or more substituents selected from fluoro, benzyl, phenoxy, chlorophenoxy, fluorophenoxy and bromophenoxy, or any isomer thereof. Processes for preparing these compounds and intermediates for use therein, insecticidal compositions containing these compounds and the use thereof are also disclosed.Type: GrantFiled: February 25, 1987Date of Patent: December 13, 1988Assignee: Imperial Chemical Industries PLCInventors: Michael J. Bushell, Robin A. E. Carr
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Patent number: 4772755Abstract: A method for synthesizing a tri-substituted phenyl compound (I) by using a 1,2-addition followed by a 1,4-addition to 1,4-benzoquinone (II): ##STR1## wherein X is hydroxy, alkoxy or alkanoyloxy, Ar.sup.1 is an organic group and R is an unsubstituted or substituted alkyl group.Type: GrantFiled: March 19, 1987Date of Patent: September 20, 1988Assignee: McNeilab, Inc.Inventors: Dennis C. Liotta, Cynthia A. Maryanoff, Vasken Paragamian
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Patent number: 4731450Abstract: A process for the perfluoroalkylation of aromatic derivatives. In a first stage, an aromatic derivative, sulfur dioxide and a metal selected from the group consisting of zinc, aluminum, manganese, cadmium, magnesium, tin, iron, nickel and cobalt, are brought into contact in a solvent, preferably a polar aprotic solvent. In a second stage, a perfluoroalkyl bromide or iodide is added to react with the aromatic derivative.Type: GrantFiled: May 21, 1986Date of Patent: March 15, 1988Assignee: Rhone-Poulenc Specialites ChimiquesInventors: Claude Wakselman, Marc Tordeux
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Patent number: 4725683Abstract: Novel intermediates useful in the preparation of fluorophenoxyphenoxypropionates and derivatives thereof which possess herbicidal activity selectively in the presence of broadleaf crops.Type: GrantFiled: August 12, 1985Date of Patent: February 16, 1988Assignee: The Dow Chemical CompanyInventors: Richard B. Rogers, B. Clifford Gerwick, III
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Patent number: 4723005Abstract: New anisotropic compounds of the formula (1) are useful in liquid crystal mixtures for electrooptical displays; at least one of the end groups of the compounds (1) is an alkyl group which carries cyano or halogen in a terminal or non-terminal position. This offers advantages for longitudinal polarization and/or cross-polarization of the anisotropic compounds with the aid of the comparatively highly polarizing cyano or halogen substituents, in particular high clear points, low .DELTA..epsilon./.epsilon..perp. values and/or negative .DELTA..epsilon. values.Type: GrantFiled: September 10, 1984Date of Patent: February 2, 1988Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Tuong Huynh-Ba, Maged A. Osman
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Patent number: 4707295Abstract: Bicyclooctane derivatives of the formula IR.sup.1 --A.sup.1 --A.sup.2 --R.sup.2 IwhereinR.sup.1 and R.sup.2 independently of one another are each an alkyl group which has 1-12 C atoms and in which it is also possible for one or two non-adjacent CH.sub.2 groups to be replaced by O atoms and/or CO groups and/or --O13 CO groups and/or --CO--O groups and/or --CH.dbd.CH-- groups, one of the radicals R.sup.1 and R.sup.2 being also --A.sup.3 --R.sup.3,A.sup.1 is a 1,4-cyclohexylene group which is unsubstituted or substituted in the 1-position and/or 2-position and/or 3-position and/or 4-position by alkyl which has in each case 1-5 C atoms and is unsubstituted or substituted or fluorinated, and in which it is also possible for one or two non-adjacent CH.sub.2 groups to be replaced by one or two different groupings from the group --O--, --CO--, --CH.dbd.CH--, --S--, --SO-- or --SO.sub.2 --, or is substituted by F, Cl, Br, CN and/or CHO,A.sup.2 is a 1,4-bicyclo[2.2.2] octylene group,--A.sup.3 --R.sup.3 is --Cy--R.sup.Type: GrantFiled: March 24, 1986Date of Patent: November 17, 1987Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Ludwig Pohl, Bernhard Scheuble, Andreas Wachtler, Reinhard Hittich, Peter Fuss
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Patent number: 4690948Abstract: Ring opened halogenated Resorcyclic Acid Lactone (RAL) derivatives having the structure: ##STR1## are used to increase rumen fermentation efficiency.Type: GrantFiled: December 1, 1986Date of Patent: September 1, 1987Assignee: International Minerals & Chemical Corp.Inventor: Jing-Jong Lu
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Patent number: 4686024Abstract: The present invention relates to novel perfluoro chemicals (PFC), particularly perfluorocyclic ethers and polyfluorinated compounds containing a few chlorine atoms and to a method for the preparation thereof.Type: GrantFiled: February 1, 1985Date of Patent: August 11, 1987Assignee: The Green Cross CorporationInventors: Kirby V. Scherer, Jr., Taizo Ono, Kouichi Yamanouchi, Kazumasa Yokoyama
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Patent number: 4686289Abstract: New anisotropic compounds with a cross-polarizing substituent have the formula (1) ##STR1## The increase in .epsilon..perp. is achieved by the polarizing group X, preferably the cyano group or a halogen atom, which is not laterally on the ring, as with the known compounds, but is on the bridge, that is to say is part of the main bridge bonding rings A and B to one another. Ring A has the formula (1a) or (1b) given herein and is always cycloaliphatic, while ring B can be identical to ring A or is an aromatic ring of the formula (1c) or (1d) herein. R.sup.1 and R.sup.2 are identical or different end groups of the formula (1e) herein.The radical X on the bridge causes less widening of the molecule than a radical X on a ring, which provides comparatively higher clear points and moreover enables aromatic rings to be omitted from the anisotropic compounds.Type: GrantFiled: February 25, 1986Date of Patent: August 11, 1987Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Tuong Huynh-Ba, Maged A. Osman
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Patent number: 4680310Abstract: Tetrahydronaphthalene derivatives of the formula ##STR1## wherein Y, m, n, R and R.sup.1 to R.sup.9 are as set forth herein, are described.These compounds have a pronounced calcium-antagonistic and anti-arrhythmic activity and can accordingly be used as medicaments, especially for the control or prevention of angina pectoris, ischaemia, arrhythmias and high blood pressure. The compounds of formula I can be prepared by the amination of a compound of the formula ##STR2## with a corresponding N-methyl-phenylalkylamine and optional subsequent O-acylation. Compounds of formula II and IV are also described and are within the scope of the invention.Type: GrantFiled: October 10, 1985Date of Patent: July 14, 1987Assignee: Hoffmann-La Roche Inc.Inventors: Urs Hengartner, Henri Ramuz
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Patent number: 4666925Abstract: Compounds of the formula ##STR1## wherein Q is 0 or S, R.sup.1 and R.sup.2 are H, halogen, (halo)alkyl or (halo)alkoxy or together are methylenedioxy, R.sup.3 is isopropyl optionally fluoro-substituted and R.sup.4 are the residues of certain alcohols of the pyrethroid type, are useful as insecticides.Type: GrantFiled: September 23, 1985Date of Patent: May 19, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventor: King M. Sun
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Patent number: 4628123Abstract: A process for the synthesis of 2-methoxy-6-bromo-naphthalene, wherein the 2-methoxy-naphthalene is brominated by means of Br.sub.2 to 1,6-dibromo-2-methoxy-naphthalene and the latter is then dehalogenated, without any separation from the liquid medium of reaction, by addition of iron.Type: GrantFiled: October 22, 1985Date of Patent: December 9, 1986Assignee: Montedison S.p.A.Inventor: Giampiero Borsotti
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Patent number: 4627933Abstract: Compounds of the formulaR.sup.1 --Q.sup.1 --(CH.sub.2).sub.m --(COO).sub.n --(CH.sub.2).sub.p --Q.sup.2 --R.sup.2whereinR.sup.1 and R.sup.2 are each independently alkyl or alkoxy each of 1-12 C atoms, F, Cl, Br, CN or --Q.sup.3 --R.sup.3, or one of R.sup.1 and R.sup.2 can also be H;Q.sup.1, Q.sup.2 and Q.sup.3 are each independently 1,4-phenylene, 1,4-cyclohexylene, 1,4-bicyclo(2,2,2)-octylene or 1,3-dioxane-2,5-diyl, each of which is unsubstituted or substituted by 1-4 fluorine, chlorine or bromine atoms;R.sup.3 is alkyl or alkoxy each of 1-8 C atoms, H, F, Cl, Br or CN;m is 1, 2, 3, 4, 5 or 6; n is 0 or 1; and p is 0, 1, 2, 3, 4 or 5; the sum of (m+p) being 2, 4 or 6 and the sum of (m+n+p) being at least 3;but with the proviso that Q.sup.3 is unsubstituted 1,4-phenylene or 1,4-phenylene substituted by a fluorine, chlorine or bromine atom, only when n=1 or (m+p)=6 or at least one of R.sup.1 or R.sup.3 is F, Cl or Br or none of R.sup.1 to R.sup.3 is CN or two of the radicals R.sup.1 to R.sup.Type: GrantFiled: July 7, 1983Date of Patent: December 9, 1986Assignees: Merck Patent Gesellschaft mit beschrankter Haftung, The Secretary of State for Defense in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: Rudolf Eidenschink, Joachim Krause, Beatrice M. Andrews, George W. Gray, Neil Carr
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Patent number: 4622163Abstract: New anisotropic compounds with a cross-polarizing substituent have the formula (1) ##STR1## The increase in .epsilon..perp. is achieved by the polarizing group X, preferably the cyano group or a halogen atom, which is not laterally on the ring, as with the known compounds, but is on the bridge, that is to say is part of the main bridge bonding rings A and B to one another. Ring A has the formula (1a) or (1b) given herein and is always cycloaliphatic, while ring B can be identical to ring A or is an aromatic ring of the formula (1c) or (1d) herein. R.sup.1 and R.sup.2 are identical or different end groups of the formula (1e) herein. The radical X on the bridge causes less widening of the molecule than a radical X on a ring, which provides comparatively higher clear points and moreover enables aromatic rings to be omitted from the anisotropic compounds.Type: GrantFiled: September 10, 1984Date of Patent: November 11, 1986Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Tuong Huynh-Ba, Maged A. Osman
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Patent number: 4595763Abstract: Aromatic hydroxyl- or thiol-containing compounds are methylated by contacting with methyl trichloroacetate at elevated temperatures in the presence of an initiator.Type: GrantFiled: June 27, 1983Date of Patent: June 17, 1986Assignee: The Dow Chemical CompanyInventors: James M. Renga, Pen-Chung Wang
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Patent number: 4556745Abstract: A liquid crystal composition includes at least one compound of Formula (I) as follows:A--CH.sub.2.CH.sub.2 --B Formula (I)where A and B are substituted ring structures which include terminal alkyl groups, A being selected from: ##STR1## where R'.sub.1 is an alkyl group R.sub.1, an alkoxy group R.sub.1 O, an alkylcarbonyloxy group R.sub.1 CO.O or an alkoxycarbonyloxy group R.sub.1 OCO.O; ##STR2## where R.sub.1 is an alkyl group; or ##STR3## where R.sub.1 is an alkyl group; and B being selected from: ##STR4## where R'.sub.2 is an alkyl group R.sub.2, an alkoxy group OR.sub.2, an alkylcarbonyloxy group OCO.R.sub.2 or an alkoxycarbonyloxy group OCO.OR'.sub.2 ; and X is hydrogen or a cyano group or a methyl group or a halogen; ##STR5## where R.sub.2 is an alkyl group; or ##STR6## where R.sub.2 is an alkyl group; ##STR7## being a trans-1,4-disubstituted cyclohexane ring and ##STR8## a 1,4-disubstituted bicyclo(2,2,2)octane ring.Type: GrantFiled: March 26, 1984Date of Patent: December 3, 1985Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: Neil Carr, George W. Gray
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Patent number: 4540829Abstract: New compositions of matter are disclosed which are allylated di and polycyclopentadiene diphenols. These new compositions are useful in thermoset resin compositions comprising styrene, a dicyclopentadiene-modified unsaturated polyesteramide and said allylated di and polycyclopentadiene diphenol(s).Type: GrantFiled: June 18, 1984Date of Patent: September 10, 1985Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 4538003Abstract: Process for the monoalkylation/monoarylation of dihaloaromatic compounds by treating the latter with selected magnesium or zinc organometallic reagents in the presence of a nickel/bidentate or tridentate phosphorus ligand. The products are intermediates to agricultural and pharmaceutical compounds.Type: GrantFiled: February 24, 1984Date of Patent: August 27, 1985Assignee: E. I. Du Pont de Nemours and CompanyInventor: Wilson Tam
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Patent number: 4518808Abstract: Disclosed is a process for the preparation of certain dichloro-hydroxy and alkoxy aromatic compounds by reacting the corresponding unchlorinated compound with sulfuryl chloride in the presence of acetic acid, propionic acid or lower alkyl esters thereof.Type: GrantFiled: September 29, 1983Date of Patent: May 21, 1985Assignee: Eastman Kodak CompanyInventors: Richard H. S. Wang, Garry L. Myers
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Patent number: 4499310Abstract: A process and intermediates for preparing 6-(lower alkoxy)-5-(trifluoromethyl)-1-naphthalenecarboxylic acid derivatives are disclosed. The derivatives are useful for preparing aldose reductase inhibitors. With reference to the process, 1,1,1-trifluoro-5-(2-methylphenyl)-2,3-pentadione 3-oxime is cyclized to give a key intermediate 3,4-dihydro-1-hydroxy-5-methyl-1-(trifluoromethyl)-2(1H)-naphthalenone oxime; and 3,4-dihydro-1-hydroxy-5-methyl-1-(trifluoromethyl)-2(1H)-naphthalenone is aromatized to 5-methyl-1-(trifluoromethyl)-2-naphthalenol with a dehydrating agent.Type: GrantFiled: June 22, 1983Date of Patent: February 12, 1985Assignee: Ayerst, McKenna & Harrison, Inc.Inventors: Kazimir Sestanj, Steven Fung, Nedumparambil A. Abraham, Francesco Bellini
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Patent number: 4486598Abstract: Novel compounds of the following general formula: ##STR1##Type: GrantFiled: February 22, 1982Date of Patent: December 4, 1984Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4476131Abstract: Tricyclic benzo fused compounds of the formula ##STR1## and pharmaceutically acceptable cationic and acid addition salts thereof, wherein n is zero, 1 or 2, and t is 1 or 2; M is CH or N, R.sub.1 is H or certain acyl groups; Q is CO.sub.2 R.sub.4, COR.sub.5, C(OR.sub.7)R.sub.5 R.sub.6, CN, CONR.sub.9 R.sub.10, CH.sub.2 NR.sub.9 R.sub.10, CH.sub.2 NHCOR.sub.11, CH.sub.2 NHSO.sub.2 R.sub.12, 5-tetrazolyl or when n is 1, Q and OR.sub.1 together form a lactone or certain reduced derivatives thereof; and Z is certain alkyl, alkoxy, alkoxyalkyl, aralkyl, aralkoxy, aryloxyalkyl or aralkoxyalkyl groups, are valuable central nervous system active agents, methods for their use, pharmaceutical compositions containing them and certain intermediates therefor.Type: GrantFiled: March 16, 1982Date of Patent: October 9, 1984Assignee: Pfizer Inc.Inventors: James F. Eggler, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4421739Abstract: The invention provides compounds which are particularly valuable for use as the active ingredient in sun tan lotions and creams and the like. These compounds have the general formula: ##STR1## in which Y denotes hydrogen or the radical SO.sub.3 H or a salt thereof with an organic or inorganic base, and Z denotes the radical --CH.sub.2 Br or --CHBrBr or a radical Z' which denotes the radical --CH.sub.2 I, --CH.sub.2 R, --CHR'R', --CHO or --COOR", in which R denotes --NR.sub.1 R.sub.2, --N.sup.+ R.sub.1 R.sub.2 R.sub.3, --OR.sub.4, --OCOR.sub.5, --SR.sub.6, --CN, -COOR" or --SSO.sub.3 Na, in which R.sub.1 and R.sub.2 independently denote hydrogen, C.sub.1-18 alkyl or hydroxyalkyl, or R.sub.1 and R.sub.2, together with the nitrogen atom to which they are attached, denote a heterocyclic ring, R.sub.3 denotes C.sub.1-4 alkyl or hydroxyalkyl or sulphonatopropyl, R.sub.4 denotes hydrogen, alkyl, polyoxyethylene, aryl which is optionally substituted, menthyl or dialkylaminoalkyl, R.sub.Type: GrantFiled: March 14, 1978Date of Patent: December 20, 1983Assignee: L'OrealInventors: Claude Bouillon, Charles Vayssie
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Patent number: 4408077Abstract: A process and intermediates for preparing 6-(lower alkoxy)-5-(trifluoromethyl)-1-naphthalenecarboxylic acid derivatives are disclosed. The derivatives are useful for preparing aldose reductase inhibitors. With reference to the process, 1,1,1-trifluoro-5-(2-methylphenyl)-2,3-pentadione 3-oxime is cyclized to give a key intermediate 3,4-dihydro-1-hydroxy-5-methyl-1-(trifluoromethyl)-2(1H)-naphthalenone oxime; and 3,4-dihydro-1-hydroxy-5-methyl-1-(trifluoromethyl)-2(1H)-naphthalenone is aromatized to 5-methyl-1-(trifluoromethyl)-2-naphthalenol with a dehydrating agent.Type: GrantFiled: November 13, 1981Date of Patent: October 4, 1983Assignee: Ayerst, McKeena & Harrison, Inc.Inventors: Kazimir Sestanj, Steven Fung, Nedumparambil A. Abraham, Francesco Bellini
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Patent number: 4357078Abstract: Novel liquid crystal compounds exhibiting a low dielectric anisotropy have a structural formula: ##STR1## where R.sub.1 is an alkyl group, R.sub.2 is a group containing an alkyl group R and is either an alkyl group R, an alkoxy group OR, an alkylcarbonyloxy group OCOR or an alkoxycarbonyloxy group OCOOR, R.sub.1 and R containing up to 18 carbon atoms, ##STR2## is a trans-1,4-disubstituted cyclohexane ring ##STR3## or a 1,4-disubstituted bicyclo(2,2,2)octane ring ##STR4## and Ar is a 1,4 disubstituted benzene ring ##STR5## a 3-fluoro-1,4 disubstituted benzene ring ##STR6## or a 2,6 disubstituted naphthalene ring ##STR7## These compounds may be used in liquid crystal mixture compositions for use in a number of known electro-optic effects.The compounds may be prepared by routes in which the individual steps involved are known.Type: GrantFiled: January 27, 1981Date of Patent: November 2, 1982Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: Neil Carr, George W. Gray, Stephen M. Kelly
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Patent number: 4351950Abstract: Novel substituted arylene compounds and methods for their preparation and use are disclosed. These new compounds are useful as anti-arteriosclerotic agents.Type: GrantFiled: January 2, 1980Date of Patent: September 28, 1982Assignee: Warner-Lambert CompanyInventor: Ila Sircar
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Patent number: 4338316Abstract: The disclosure relates to 9.beta.-aryloxy prostane derivatives, for example 16-(3-chlorophenoxy)-11.alpha.,15.alpha.-dihydroxy-16-methyl-9.beta.-pheno xy-18,19,20-trinor-5-cis,13-trans-prostadienoic acid, which possess high activity as abortifacients, cervical softeners, inducers of parturition or inhibitors of gastric acid production in mammals. These properties are typical of prostaglandin analogues of the E series, but chemically the new 9.beta.-aryloxy prostane derivatives are prostaglandin F series analogues and are therefore more stable than the E series analogues previously used for the above purposes. The new derivatives are manufactured by known analogy processes, and are formulated in conventional manner.Type: GrantFiled: September 26, 1979Date of Patent: July 6, 1982Assignee: Imperial Chemical Industries LimitedInventor: Peter R. Marsham
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Patent number: 4335055Abstract: Compounds of the formula I ##STR1## in which Z, Z.sub.1, R, m and p are as defined in patent claim 1, can be obtained in a simple and economical manner by a novel process wherein a halide of the formula II ##STR2## is reacted with a substituted or unsubstituted vinylbenzene or vinylnaphthalene derivative in the presence of a base and of certain palladium catalysts, such as palladium acetate. The compounds (I) or functional derivatives preparable therefrom are useful, for example, for the preparation of known dyes or fluorescent brighteners, or can be used directly as fluorescent brighteners or as scintillators.Type: GrantFiled: May 8, 1981Date of Patent: June 15, 1982Assignee: Ciba-Geigy CorporationInventors: Hans-Ulrich Blaser, Dieter Reinehr, Alwyn Spencer
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Patent number: 4321359Abstract: A method for polymerizing octafluoronaphthalene and the resulting perfluorocompounds prepared therefrom. Polymerization is accomplished by reacting the octafluoronaphthalene monomer with a mono or difluoroxyperfluoroalkane.Type: GrantFiled: August 29, 1980Date of Patent: March 23, 1982Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: Madeline S. Toy, Roger S. Stringham
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Patent number: 4314086Abstract: Aliphatic/aromatic ethers are prepared by reacting an aliphatic halide with either an alkali or alkaline earth metal, or ammonium phenolate or naphtholate, in an inert organic solvent, and in the presence of at least one tertiary amine sequestering agent having the formula:N--CHR.sub.1 CHR.sub.2 --O--CHR.sub.3 --CHR.sub.4 --O--.sub.n R.sub.5 ].sub.Type: GrantFiled: June 20, 1980Date of Patent: February 2, 1982Assignee: Rhone-Poulenc IndustriesInventors: Gerard Soula, Daniel Michelet
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Patent number: 4306075Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet antiaggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), and methano (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2',9-methano (or 2',9-metheno)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.Type: GrantFiled: December 22, 1980Date of Patent: December 15, 1981Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4306076Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet anti-aggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), and methano (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2',9-methano (or 2',9-metheno)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.Type: GrantFiled: December 22, 1980Date of Patent: December 15, 1981Assignee: The Upjohn CompanyInventor: Norman A. Nelson
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Patent number: 4288386Abstract: The Ullman reaction for the preparation of diaryl ethers by coupling aryl halides with metal phenolates is conducted in the presence of at least one tertiary amine sequestering agent having the formula:N--CHR.sub.1 --CHR.sub.2 --O--CHR.sub.3 --CHR.sub.4 --O--.sub.n R.sub.5 ].sub.Type: GrantFiled: May 12, 1980Date of Patent: September 8, 1981Assignee: Rhone-Poulenc IndustriesInventors: Gerard Soula, Louis Linguenheld
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Patent number: 4224244Abstract: Novel 9-phenyl 5,6-dimethyl-nona-2,4,6,8-tetraenoic acid, tetraenal or tetraenol derivatives useful as anti-tumor agents.Type: GrantFiled: May 9, 1979Date of Patent: September 23, 1980Assignee: Hoffmann-La Roche Inc.Inventors: Werner Bollag, Rudolf Ruegg, Gottlieb Ryser
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Patent number: 4196120Abstract: Substituted 3-azabicyclo[3.1.0]hexanes, acid addition salts, method of use and method of preparation are described. The compounds have anxiolytic and analgesic activity.Type: GrantFiled: October 6, 1978Date of Patent: April 1, 1980Assignee: American Cyanamid CompanyInventors: William J. Fanshawe, Joseph W. Epstein, Lantz S. Crawley, Corris M. Hofmann, Sidney R. Safir
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Patent number: 4188495Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl of 1 to 5 carbon atoms or --CO--(CH.sub.2).sub.p --NR'R" wherein p is 0 or an integer from 1 to 4; each of R' and R" when taken individually is hydrogen or alkyl of 1 to 4 carbon atoms; R' and R" when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrollo, pyrrolidino, morpholino and N-alkylpiperazino having from 1 to 4 carbon atoms in the alkyl group;R.sub.2 is selected from hydrogen, alkanoyl of 1 to 6 carbon atoms and benzoyl;R.sub.3 is selected from hydrogen, methyl and ethyl;R.sub.4 is selected from hydrogen, alkyl of 1 to 6 carbon atoms and benzyl;Z is selected from:(a) alkylene having from one to nine carbon atoms;(b) --(alk.sub.1).sub.m --X--(alk.sub.2).sub.n -- wherein each of (alk.sub.1) and (alk.sub.2) is alkylene having from 1 to 9 carbon atoms, with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.Type: GrantFiled: November 14, 1977Date of Patent: February 12, 1980Assignee: Pfizer Inc.Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4163865Abstract: An improvement in a process for the preparation of a pinacol of the formula ##STR1## wherein R.sup.1 and R.sup.2 are identical or different and represent optionally substituted aliphatic, cycloaliphatic, araliphatic or an aromatic hydrocarbon radical by reducing a ketone of the formula ##STR2## wherein R.sup.1 and R.sup.2 have the abovementioned meanings with a base metal, the improvement comprising carrying out the reduction in the presence of an organic halogen compound and in the presence of a phosphoric acid amide, phosphoric acid ester and/or carboxylic acid amide.Type: GrantFiled: April 3, 1978Date of Patent: August 7, 1979Assignee: Bayer AktiengesellschaftInventors: Heinrich Wolfers, Hans Rudolph, Hans-Jurgen Rosenkranz
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Patent number: 4152356Abstract: This invention relates to a method of producing a dibenzocycloheptene compound of the structure ##STR1## in high yields which comprises: (a) hydrogenating an anthracene derivative in the 9,10 position to form a 9,10-dihydroanthracene derivative, (b) selectively mono-carbonylating one of the hydrogens in the 9,10 position to form a monoaldehyde, (c) reducing the aldehyde to form the corresponding alcohol and (d) dehydrating and expanding the center ring to form the dibenzocycloheptene compound.Type: GrantFiled: April 24, 1978Date of Patent: May 1, 1979Assignee: Exxon Research & Engineering Co.Inventor: Chang J. Kim
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Patent number: 4137272Abstract: A new process, which can be carried out on the technical scale, had been found for the preparation of 2-alkoxy-6-bromo-naphthalenes, especially suitable as starting compounds for the synthesis of estrogens, which comprises brominating 2-hydroxy-naphthalene-1-carboxylic acid with bromine, decarboxylating the 6-bromo-2-hydroxynaphthalene-1-carboxylic acid by heating the reaction mixture at 100 - 125.degree. C, and alkylating the 6-bromo-2-hydroxy-naphthalene formed. The process can be conducted easily and with high yields.Type: GrantFiled: April 28, 1977Date of Patent: January 30, 1979Assignee: Hoechst AktiengesellschaftInventors: Theodor Papenfuhs, Kurt Gengnagel