Chalcogen Attached Indirectly To The Six-membered Hetero Ring By Nonionic Bonding (e.g., Sulfato Betaines, Etc.) Patents (Class 546/339)
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Patent number: 5770108Abstract: A novel pyrimidine compound represented by the following Formulas (1) and (2), a liquid crystal composition containing said compound and a liquid crystal element having excellent characteristics such as high speed response, orientation and high contrast ratio. ##STR1## wherein R.sub.1 and R.sub.2 each represent a linear or branched alkyl or alkenyl group, an alkoxyl or alkenyloxy group; R.sub.3 and R.sub.4 each represent a linear or branched alkyl group or alkenyl group; A.sub.1 and A.sub.2 each represent a substituted or unsubstituted 1,4-phenylene group, a pyridine-2,5-diyl or trans-1,4-cyclohexylene group; X.sub.1 and X.sub.2 each represent a single bond, --COO--, --OCO--, --OCH.sub.2 or --CH.sub.2 O-- group; Y.sub.1 and Y.sub.2 each represent --COO-- or --OCO-- group; and a, b, p, q, m and n each represent 0 or 1, provided that a+b+p+q is not 0.Type: GrantFiled: June 21, 1996Date of Patent: June 23, 1998Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Yoshiyuki Totani, Motokazu Hirao, Atsuo Otsuji, Tsutomu Ishida, Hiroe Kayashima, Masakatsu Nakatsuka
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Patent number: 5763461Abstract: Compounds of the formula ##STR1## wherein Pyr is chosen from the group consisting of pyridyl, pyrazyl, pyrimidyl, quinolyl, indolyl and 7-azaindolyl or any of these substituted with one or two substitutents chosen from alkyl, alkoxy, hydroxy, halo, cyano, nitro, hydroxyalkyl, alkoxyalkyl, alkanoyl, fluoroalkyl or the N-oxide of any of these;Y is an alkylene bridge of 3-9 carbon atoms;R.sub.1 and R.sub.2 are each independently chosen from hydrogen, halo, alkyl, alkenyl, amino, alkylthio, hydroxy, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylaikyl, alkylsulfonylalkyl, alkoxy, nitro, carboxy, alkoxycarbonyl, dialkylaminoalkyl, alkylaminoalkyl, aminoalkyl, difluoromethyl, trifluoromethyl or cyano;R.sub.Type: GrantFiled: March 21, 1997Date of Patent: June 9, 1998Assignee: SanofiInventors: David J. Aldous, Thomas R. Bailey, Guy Dominic Diana, Gee-Hong Kuo, Theodore J. Nitz
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Patent number: 5763624Abstract: 1-pyridiniumpropane-3-sulphonate is obtained by reacting 1-allylpyridinium chloride (3) and alkaline bisulfite, in an aqueous solution, in the presence of radical initiators, such as oxygen, hydrogen peroxide, peroxides, alkylhydroperoxides and alkaline or ammonium persulfates.Type: GrantFiled: June 4, 1996Date of Patent: June 9, 1998Assignee: Galvanevet S.p.A.Inventors: Francesco Minisci, Francesca Fontana, Anna Serri, Roberto Baima
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Patent number: 5759443Abstract: Objects of this invention are cyclopentyl compounds of the general formula ##STR1## wherein k signifies a whole number of 4 to 18;n signifies 0 or 1;Y.sup.1, Y.sup.2 signify a single bond, --O--, --COO-- or --OOC--;rings A, B, C each independently signify optionally mono- or difluorinated 1,4-phenylene, pyrimidine-2,5-diyl, pyridine-2,5-diyl, pyrazine-2,5-diyl, naphthalene-2,6-diyl, quinoline-2,6-diyl, thiophene-2,5-diyl, thiazole-2,5-diyl or 1,3,4-thiadiazole-2,5-diyl and ring C also signifies trans-1,4-cyclohexylene or trans-1,3-dioxane-2,5-diyl;Z.sup.1 signifies a single bond, --COO--,--OOC-- or --C.tbd.C--;Z.sup.2 signifies --COO--, --OOC--, --OCH.sub.2 --, --CH.sub.2 O-- or --(CH.sub.2).sub.Type: GrantFiled: June 26, 1997Date of Patent: June 2, 1998Assignee: Rolic AGInventors: Jurg Funfschilling, Alois Villiger
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Patent number: 5747422Abstract: Substituted 2-phenylpyridines I ##STR1## where substituents have the meaning described in the specification and their use as herbicides; for the desiccation/defoliation of plants.Type: GrantFiled: July 3, 1997Date of Patent: May 5, 1998Assignee: BASF AktiengesellschaftInventors: Peter Schafer, Gerhard Hamprecht, Elisabeth Heistracher, Ralf Klintz, Hartmann Konig, Helmut Walter, Karl-Otto Westphalen, Ulf Misslitz
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Patent number: 5744058Abstract: Dienes of the formula I ##STR1## in which n is 0, 1, 2, 3, 4 or 5,r is 1, 2 or 3,s is 1 or 2, ##STR2## is trans-1,4-cyclohexylene or trans-1,3-dioxane-2,5-diyl, ##STR3## is trans-1,4-cyclohexylene, trans-1,3-dioxane-2,5-diyl, unfluorinated or mono- or polyfluorinated 1,4-phenylene, in which one or two CH groups may also be replaced by N, or the central part ##STR4## Z is a single bond, a bridging member selected from the group consisting of --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --C.tbd.C--, --CO--O--, --CH.sub.2 O--, --OCH.sub.2 -- and --O--CO--, or any desired combination of two such bridging members, where two O atoms are not linked directly to one another, andR is --CN, --NCS, halogen or an alkyl, alkenyl, alkoxy or alkenyloxy group, in each case having up to 12 carbon atoms and in each case unsubstituted or monosubstituted or polysubstituted by fluorine and/or chlorine.Type: GrantFiled: June 2, 1995Date of Patent: April 28, 1998Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Volker Reiffenrath, Bernhard Rieger
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Patent number: 5739144Abstract: Compounds of general formula (1) ##STR1## are described wherein Y is a halogen atom or a group --OR.sup.1, where R.sup.1 is an optionally substituted alkyl group; X is --O--, --S-- or --N(R.sup.7)--, where R.sup.7 is a hydrogen atom or an alkyl group; R.sup.2 is an optionally substituted cycloalkyl or cycloalkenyl group; R.sup.3 and R.sup.4, which may be the same or different, is each a hydrogen atom or an alkyl, --CO.sub.2 R.sup.8 (where R.sup.8 is a hydrogen atom or an alkyl, aryl, or aralkyl group), --CONR.sup.9 R.sup.10 (where R.sup.9 and R.sup.10 which may be the same or different is each a hydrogen atom or an alkyl, aryl or aralkyl group), --CSNR.sup.9 R.sup.10, --CN, --CH.sub.2 CN group; Z is --(CH.sub.2).sub.n -- (where n is zero or an integer 1, 2 or 3; R.sup.5 is an optionally substituted monocyclic or bicyclic aryl group optionally containing one or more heteroatoms selected from oxygen, sulphur or nitrogen atoms; R.sup.Type: GrantFiled: October 17, 1995Date of Patent: April 14, 1998Assignee: Celltech Therapeutics LimitedInventors: Graham John Warrellow, Valerie Anne Cole, Rikki Peter Alexander
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Patent number: 5733850Abstract: Substituted 2-phenylpyridines I ##STR1## where the substituents have the meaning given in the specification and their use.Type: GrantFiled: July 3, 1997Date of Patent: March 31, 1998Assignee: BASF AktiengesellschaftInventors: Peter Schafer, Gerhard Hamprecht, Elisabeth Heistracher, Ralf Klintz, Hartmann Konig, Albrecht Harreus, Norbert Gotz, Helmut Walter, Karl-Otto Westphalen, Ulf Misslitz
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Patent number: 5728838Abstract: A process for the preparation of a compound of structural formula I ##STR1## wherein R.sup.1 is alkyl, alkenyl, phenyl or substituted phenyl, which comprises the addition of R.sup.1 to an intermediate 2: ##STR2## by treatment of 2 with (R.sup.1).sub.3 M followed by reductive removal of the sulfinyl group.Type: GrantFiled: April 2, 1997Date of Patent: March 17, 1998Assignee: Merck & Co., Inc.Inventors: Ioannis Houpis, Audrey Molina, Ralph P. Volante
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Patent number: 5723621Abstract: A novel process for producing a biaryl compound represented by formula (III), which is useful as a medicine, an agricultural chemical and an electrooptical liquid-crystal display material:Ar--Ar' (III)(wherein Ar and Ar' each independently represents a substituted or unsubstituted aromatic group) which comprises the steps of (i) reacting a trialkoxysilyl-substituted aromatic compound represented by formula (I):Ar--Si(OR).sub.3 (I)(wherein Ar has the same meaning as defined above and R represents an alkyl group having from 1 to 5 carbon atoms) with a fluoride ion source in the presence of a solvent, and then (ii) adding thereto an aromatic compound represented by formula (II):X--Ar' (II)(wherein X represents an eliminating group and Ar' has the same meaning as defined above) and a catalyst comprising a transition metal of tenth group to conduct a further reaction.Type: GrantFiled: May 14, 1996Date of Patent: March 3, 1998Assignee: Chisso CorporationInventors: Koichi Shibata, Shuichi Matsui, Kazutoshi Miyazawa
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Patent number: 5723622Abstract: A synthetic method for making pyridin-propyl-sulphobetaine, without any risks for the human beings and the environment is described. It comprises reacting a pyridine substituted alkyldihalogenide and then sulphonating in water with an alkylhalogenide solvent, so as to provide pyridin-propyl-sulphobetaine which can be separated from water leaving therein water the halogenides.Type: GrantFiled: July 3, 1996Date of Patent: March 3, 1998Inventors: Giuseppe Faranda, Luciano Antonio Vailati, Claudio Valzesi, Enrico Borroni
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Patent number: 5720899Abstract: A novel liquid crystalline compound having a high elastic constant ratio (K.sub.33 /K.sub.11) and an improved solubility thereof in other liquid crystal materials, at low temperatures, and a liquid crystal composition containing the same are provided. The liquid crystalline compound is expressed by the formula (1): ##STR1## wherein Q represents CF.sub.3, CF.sub.2 H or CFH.sub.2 ; A.sub.1, A.sub.2 and A.sub.3 each independently represent trans-1,4-cyclohexylene group, 1,4-phenylene group, wherein one or more hydrogen atoms on its six-membered ring may be replaced by F, Cl or CN, pyridine-2,5-diyl group or 1,3-pyrimidine-2,5-diyl; ring B represents 1,4-phenylene group or trans-1,4-cyclohexylene group; Z.sub.1, Z.sub.2 and Z.sub.3 each independently represent covalent bond, --C.dbd.C--, --C.tbd.C--, --OCO--, --COO--, --CH.sub.2 O--, --OCH.sub.2 --, --(CH.sub.2).sub.2 -- or --(CH.sub.2).sub.4 --; l and m each independently represent an integer of 0 to 5; o and p each independently represent 0 or 1; L.sub.1 and L.Type: GrantFiled: December 30, 1996Date of Patent: February 24, 1998Assignee: Chisso CorporationInventors: Tomoyuki Kondo, Kazutoshi Miyazawa, Atsuko Fujita, Noriyuki Ohnishi, Yasuyuki Goto, Etsuo Nakagawa, Shinichi Sawada
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Patent number: 5707544Abstract: The present invention is concerned with chromophore-containing photo cross-linkable liquid crystalline compounds having the formula ##STR1## wherein A.sup.1 and A.sup.2 each represent a cross-linkable, mesogenic group; andA.sup.3 represents a dichroic group.as well as liquid crystalline mixtures which contain such compounds and their use in the cross-linked state as optical components.Type: GrantFiled: May 20, 1996Date of Patent: January 13, 1998Assignee: Rolic AGInventor: Stephen Kelly
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Patent number: 5707547Abstract: The present invention relates to trans-olefin compounds represented by the general formula (1) useful as an ingredient of liquid crystal composition, trans-olefin compounds useful as intermediate of pesticides, medical drugs, liquid crystal materials and the like, a process for producing those trans-olefin compounds, a liquid crystal composition containing the trans-olefin compound as an active ingredient, and a liquid crystal element using the liquid crystal composition. ##STR1## (In the general formula (1), R.sup.1, A.sup.1, A.sup.2, A.sup.3, Z and R.sup.2 are same as defined in the specification. Also, m, p, q, n, r, s and t are each an integer as defined in the specification.Type: GrantFiled: July 29, 1994Date of Patent: January 13, 1998Assignee: Sumitomo Chemical Company, LimitedInventors: Yukari Fujimoto, Naoyuki Takano, Takayuki Higashii, Masayoshi Minai, Chizu Sekine, Kayoko Ueda, Koichi Fujisawa, Kyoko Endo, Takeshi Tani
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Patent number: 5700943Abstract: This invention relates to a process of making a compound of formula I ##STR1## where R.sub.1 contains an .alpha.,.beta.-unsaturated carbonyl group & R.sub.n is hydrogen or nonhydrogen radicals which do not have a functional group which interferes with the coupling reaction, which process comprises coupling a thiolphenol or phenylalkylmercaptan with a chloromethylpyridine in the presence of DBU under an inert atmosphere. These compounds are leukotriene antagonists and as such can be used in treating various diseases associated with leukotrienes.Type: GrantFiled: December 20, 1994Date of Patent: December 23, 1997Assignee: SmithKline Beecham CorporationInventor: Robert A. Daines
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Patent number: 5686473Abstract: In accordance with the present invention, there is provided a class of pyridine compounds which are modulators of acetylcholine receptors. The compounds of the invention displace acetylcholine receptor ligands from their binding sites.Type: GrantFiled: June 7, 1995Date of Patent: November 11, 1997Assignee: Sibia Neurosciences, Inc.Inventors: Nicholas D. Cosford, Jean-Michel Vernier
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Patent number: 5686608Abstract: A process for preparing polycyclic aromatic compounds by cross-coupling aromatic boron compounds with aromatic halogen compounds or perfluoroalkylsulfonates in the presence of metallic palladium as catalyst comprises adding to the reactiona) at least one water-soluble complexing ligand andb) sufficient water for the reaction mixture to form an aqueous phase.The reaction of the invention proceeds chemoselectively so that even electrophilic groups such as esters or nitriles do not have an adverse effect on the course of the reaction.The use according to the invention of a water-soluble complexing ligand in an aqueous phase enables polycyclic aromatic compounds to be prepared in very good yields and at the same time very high purity, in particular without contamination by the complexing ligands.Type: GrantFiled: April 24, 1995Date of Patent: November 11, 1997Assignee: Hoechst AktiengesellschaftInventors: Steffen Haber, Javier Manero
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Patent number: 5686619Abstract: 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: March 6, 1995Date of Patent: November 11, 1997Assignee: Cytec Technology Corp.Inventors: William Elliott Bay, Matthew A. Brown, David R. Kilanowski
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Patent number: 5679285Abstract: Vinylene compounds of the formula I ##STR1## in which R, A.sup.1, Z.sup.1, X, L.sup.1, L.sup.2 and m have the meaning given in claim 1 are suitable as components of liquid-crystalline media.Type: GrantFiled: February 15, 1996Date of Patent: October 21, 1997Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Ekkehard Bartmann, Sabine Schoen, Kazuaki Tarumi
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Patent number: 5679792Abstract: Compounds of formula I ##STR1## in which R.sup.1 and R.sup.2 are, for example, an alkyl chain,A is a mesogenic group, andM is a spacer group,are highly suitable as components of liquid-crystal mixtures.Type: GrantFiled: June 1, 1995Date of Patent: October 21, 1997Assignee: Hoechst AktiengesellschaftInventors: Claus Escher, Gerhard Illian, Hubert Schlosser, Rainer Wingen
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Patent number: 5679696Abstract: This invention is directed to the pharmaceutical use of phenyl compounds, which are linked to an aryl moiety by various linkages, for inhibiting tumor necrosis factor. The invention is also directed to the compounds, their preparation and pharmaceutical compositions containing these compounds. Furthermore, this invention is directed to the pharmaceutical use of the compounds for inhibiting cyclic AMP phosphodiesterase.Type: GrantFiled: June 7, 1995Date of Patent: October 21, 1997Assignee: Rhone-Poulenc Rorer LimitedInventors: Garry Fenton, Andrew David Morley, Malcolm Norman Palfreyman, Andrew James Ratcliffe, Brian William Sharp, Keith Alfred James Stuttle, Sukanthini Thurairatnam, Bernard Yvon Jack Vacher
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Patent number: 5677455Abstract: Methyl (3R,6E)-3-?(tert-butyldimethylsilyl)oxy!-7-?2',6'-diisopropyl-4'-(4"-fluor ophenyl)-5'-(methoxymethyl)pyridin-3'-yl!-5-oxy-6-heptenoate or other 3-oxy-5-oxo-6-heptenoic acid derivative is prepared by the reaction of an aromatic aldehyde and an oxyglutaric acid derivative in an aliphatic alcohol containing a small amount of water in the presence of an alkali metal carbonate or hydrogen carbonate.Type: GrantFiled: September 6, 1995Date of Patent: October 14, 1997Assignee: Ube Industries, Ltd.Inventors: Katsumasa Harada, Akio Matsushita, Yasuhiro Kawachi, Hiroshi Sasaki
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Patent number: 5674880Abstract: Compounds of formula (1) ##STR1## are described wherein Y represents a halogen atom or a group --OR.sup.1, where R.sup.1 is an optionally substituted alkyl group; R.sup.2 represents an optionally substituted cycloalkyl or cycloalkenyl group; R.sup.3 is a monocyclic or bicyclic aryl group optionally containing one or more heteroatoms selected from oxygen or sulphur atoms or a group --N(R.sup.4)-- where R.sup.4 is a hydrogen atom or an alkyl group; X is --O--, --S--, or --N(R.sup.4)--, where R.sup.5 is a hydrogen or an alkyl group; with the proviso that when X is --O-- then R.sup.3 is not a 3-cyanamino-6-pyridazinyl or a 3-chloro-6-pyridazinyl group; and the salts, solvates, hydrates and N-oxides thereof.The compounds are selective and potent inhibitors of phosphodiesterase IV and are useful for the prophylaxis and treatment of inflammatory diseases and the alleviation of conditions associated with central nervous malfunction.Type: GrantFiled: June 6, 1995Date of Patent: October 7, 1997Assignee: Celltech Therapeutics LimitedInventors: Ewan Campbell Boyd, Michael Anthony William Eaton, Graham John Warrellow
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Patent number: 5672609Abstract: The present invention is directed to compounds of Formula I: ##STR1## wherein: n is 2 or 3;R is dimethylamino, diethylamino, 1-piperidinyl, 1-pyrrolidinyl, 4-morpholinyl, or 1-hexamethyleneimino;R.sup.1 is hydrogen, loweralkyl of C.sub.1 -C.sub.4, phenyl, or mono or di-substituted phenyl wherein each substituent is independently halo, methyl, hydroxy, C.sub.1 -C.sub.6 -alkoxy, benzyloxy, C.sub.1 -C.sub.6 -alkanoyloxy, benzoyloxy, substituted benzoyloxy bearing 1 to 3 substituents each of which is independently halo, C.sub.1 -C.sub.4 -loweralkyl, or C.sub.1 -C.sub.4 -loweralkoxy, C.sub.1 -C.sub.5 -alkoxycarbonyloxy, or C.sub.4 -C.sub.6 -alkylsulfonyloxy;R.sup.2 is hydrogen, hydroxy, C.sub.1 -C.sub.6 -alkoxy, benzyloxy, C.sub.1 -C.sub.6 -alkanoyloxy, benzoyloxy, substituted benzoyloxy bearing 1 to 3 substituents each of which is independently halo, C.sub.1 -C.sub.4 -loweralkyl, or C.sub.1 -C.sub.4 -loweralkoxy, C.sub.1 -C.sub.5 -alkoxycarbonyloxy, or C.sub.4 -C.sub.Type: GrantFiled: July 18, 1996Date of Patent: September 30, 1997Assignee: Eli Lilly and CompanyInventors: Henry Uhlman Bryant, Don Richard Finley, Ken Matsumoto
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Patent number: 5662828Abstract: A compound having an unsaturated side chain represented by the formula: ##STR1## in which A and B are the same and different and represent an aromatic or heterocyclic group or either one of A and B represents a single bond; X.sub.1, X.sub.2 and X.sub.3 are the same or different and represent a hydrogen atom or a lower alkyl group; R.sub.1 represents a saturated or unsaturated alkyl group which may be substituted with a halogen atom or an alkoxyalkyl group which may be substituted with a halogen atom; X represents --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --C.tbd.C-- or a single bond; n is an integer of 0 to 6; q is an integer of 1 to 15; p and s are each 0 or 1; and the asterisk * indicates an asymmetric carbon atom, which is useful as an intermediate of a liquid crystal or a monomer of a liquid crystalline polymer.Type: GrantFiled: June 6, 1995Date of Patent: September 2, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Yoshiaki Tsubata, Kayoko Ueda, Koichi Fujisawa, Takayuki Higashii, Masayoshi Minai, Naoyuki Takano, Yukari Fujimoto
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Patent number: 5658489Abstract: A diphenylacetylene compound of the formula [1]: ##STR1## wherein R is a C.sub.1 -C.sub.12 alkyl group, a C.sub.2 -C.sub.12 alkenyl group or a C.sub.2 -C.sub.16 alkoxyalkyl group; X.sup.1, X.sup.2, X.sup.3, X.sup.4, Y.sup.1, Y.sup.2, Y.sup.3 and Y.sup.4 are independently from each other a --CH-- group, a --CF-- group or a nitrogen atom;A is a hydrogen atom, a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group, a cyano group, a 4-R.sup.1 -(cycloalkyl) group, 4-R.sup.1 -(cycloalkenyl) group or a R.sup.1 --(O).sub.m group in which R.sup.1 is a C.sub.1 -C.sub.12 alkyl group, a C.sub.2 -C.sub.12 alkenyl group or a C.sub.2 -C.sub.12 alkynyl group; and m is 0 or 1, which has an excellent anisotropy of refractive index and a low viscosity and is useful as a component of a liquid crystal composition.Type: GrantFiled: October 13, 1994Date of Patent: August 19, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Takayuki Higashii, Yukari Fujimoto, Masayoshi Minai, Tsutomu Matsumoto
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Patent number: 5658942Abstract: Compounds of formula (I): ##STR1## in which: R represents hydrogen, methyl or hydroxy; X represents an alkyl, alkenyl, cycloalkyl, aryl, aralkyl, or heterocyclic group; A represents a single bond, or an alkylene, alkenylene, alkynylene or alkadienylene group; Y represents hydrogen, or an aryl, cycloalkyl or heterocyclic group; have valuable antihypercholesteremic activities and may be used in the treatment of disorders arising from a blood cholesterol imbalance in humans and other animals.Type: GrantFiled: March 7, 1995Date of Patent: August 19, 1997Assignee: Sankyo Company, LimitedInventors: Masaaki Kurabayashi, Hiroshi Kogen, Hiroshi Kadokawa, Hideshi Kurihara, Kazuo Hasegawa, Masao Kuroda
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Patent number: 5648021Abstract: This invention relates to novel phenanthrene derivatives of the formula (I) which are particularly suitable for use in liquid-crystal mixtures. The compounds of formula (I) have a broad range of applications. Depending on the choice of substituents, they can be used as base materials from which liquid-crystalline phases are predominantly composed. They can also be added to liquid-crystalline base materials to modify the dielectric and/or optical anisotropy of a dielectric and to optimize its threshold voltage or viscosity. Liquid-crystalline mixtures containing compounds of formula (I) are particularly suitable for use in electrooptical switching and display devices.Type: GrantFiled: January 13, 1995Date of Patent: July 15, 1997Assignee: Hoechst AktiengesellschaftInventors: Rainer Wingen, Barbara Hornung
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Patent number: 5646158Abstract: This invention relates to certain 1,3,3-(trisubstituted)cyclohex-1-ene monomers and related compounds which are useful in treating allergic and inflammatory diseases and for inhibiting the production of Tumor Necrosis Factor (TNF).Type: GrantFiled: February 27, 1996Date of Patent: July 8, 1997Assignee: SmithKline Beecham CorporationInventors: Siegfried B. Christensen, IV, Joseph M. Karpinski, M. Dominic Ryan, Paul E. Bender
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Patent number: 5643914Abstract: This invention relates to a compound of formula 1 ##STR1## or an N-oxide, or a pharmaceutically acceptable salt, where A is CH.sub.2 and Z is S(O).sub.q where q is 0, 1 or 2, CH.sub.2, CHOH, CO, NR.sub.x, or O, orA is C.dbd.O and Z is NR.sub.x ;m is 0-5;R.sub.x is hydrogen or lower alkyl;R is C.sub.1 to C.sub.20 -aliphatic, unsubstituted or substituted five-membered heteroaryl-C.sub.1 to C.sub.10 -aliphatic-O--, unsubstituted or substituted phenyl-C.sub.1 to C.sub.10 -aliphatic where substituted p from the group consisting of lower alkoxy, lower alkyl, trihalomethyl, and halo, or R is C.sub.1 to C.sub.20 -aliphatic-O--, or R is unsubstituted or substituted phenyl-C.sub.1 to C.sub.10 -aliphatic-O-- where substituted phenyl has one or more radicals selected from the group consisting of lower alkoxy, lower alkyl, trihalomethyl, and halo;R.sub.1 is R.sub.4, --(C.sub.1 to C.sub.5 aliphatic)R.sub.4, --(C.sub.1 to C.sub.5 aliphatic)CHO, --(C.sub.1 to C.sub.5 aliphatic)CH.sub.2 OR.sub.5;R.sub.2 and R.sub.Type: GrantFiled: December 19, 1994Date of Patent: July 1, 1997Assignee: SmithKline Beecham CorporationInventor: Robert A. Daines
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Patent number: 5633257Abstract: Compounds of general formula (1) ##STR1## are described wherein Y is a halogen atom or a group --OR.sup.1, wherein R.sup.1 is an optionally substituted alkyl group; X is --O--, --S--, or --N(R.sup.6), wherein R.sup.6 is a hydrogen atom or an optionally substituted alkyl group; R.sup.2 is an optionally substituted cycloalkyl or cycloalkenyl group; R.sup.3 and R.sup.4, which may be the same or different, is each a hydrogen atom or an optionally substituted alkyl, --CO.sub.2 R.sup.7 (wherein R.sup.7 is a hydrogen atom, am optionally substituted alkyl, aralkyl, aryl, aryloxyalkyl, alkanoyloxyalkyl or aroyloxyalkyl group), --CONR.sup.8 R.sup.9 (where R.sup.8 and R.sup.9, which may be the same or different, is as defined for R.sup.7), --CSNR.sup.8 R.sup.9, --CN or --CH.sub.2 CN group; Z is --(CH.sub.2).sub.n -- where n is zero or an integer 1, 2 or 3; R.sup.Type: GrantFiled: March 9, 1994Date of Patent: May 27, 1997Assignee: Celltech Therapeutics LimitedInventors: Graham J. Warrellow, Valerie A. Cole, Rikki P. Alexander
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Patent number: 5630962Abstract: 2-Fluoropyridines, processes for their preparation and their use in ferroelectric liquid crystal mixturesA 2-fluoropyridine of the formula (I) ##STR1## in which the symbols have the following meaning: R.sup.1, R.sup.2, independently of one another, are, for example, H or straight-chain or branched alkyl, A.sup.1, A.sup.2, A.sup.3, A.sup.4, identical or different, are, for example, 1-phenylene, pyrazine-2,5-diyl or trans-1,4-cyclohexylene, M.sup.1, M.sup.2, M.sup.3, M.sup.4, identical or different, are, for example, --O-- or --CO--O--, R.sup.3, R.sup.4, R.sup.6, R.sup.7, independently of one another, are, for example, H or straight-chain or branched alkyl, M.sup.5 is, for example, --O--CO-- or a single bond, k, l, m, n, o, p, q, r are zero or one, with the proviso that the sum of k+m+p+r is less than 4 and greater than zero, can advantageously be used as a component in ferroelectric liquid crystal mixtures.Type: GrantFiled: May 11, 1995Date of Patent: May 20, 1997Assignee: Hoechst AktiengesellschaftInventors: Hubert Schlosser, Rainer Wingen, Gerd Illian, Claus Escher
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Patent number: 5629323Abstract: Amide Derivatives of formula (I) wherein R.sup.1 is a mono or bicyclic heteroaryl radical, R.sup.2 is cycloalkyl, R.sup.3 and R.sup.4 each represent hydrogen or lower alkyl, and R.sup.5 is a group of formula (A) or (B) or (C): R.sup.8 --CH.sub.2 --CH.sub.2 -- or (D) or (E): R.sup.9 OCH.sub.2 CHOHCH.sub.2 -- or (F): R.sup.9 OCH.sub.2 CH.sub.2 -- and their pharmaceutically acceptable salts are 5-HT.sub.1A binding agents and may be used, for example, as anxiolytics.Type: GrantFiled: May 25, 1995Date of Patent: May 13, 1997Assignee: John Wyeth & Brother, Ltd.Inventors: Ian A. Cliffe, Anderson D. Ifill
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Tri-substituted (aryl or heteroaryl) derivatives and pharmaceutical compositions containing the same
Patent number: 5622977Abstract: Compounds of the general formula (1) ##STR1## are described wherein Y is halogen or --OR.sup.1, where R.sup.1 is a substituted or unsubstituted alkyl; X is --O--, --S-- or --N(R.sup.8)--, where R.sup.8 is hydrogen or alkyl; R.sup.2 is substituted or unsubstituted alkyl, alkenyl, cycloalkyl or cycloalkenyl; R.sup.3 is hydrogen, halogen or --OR.sup.9, where R.sup.9 is hydrogen or substituted or unsubstituted alkyl, alkenyl, alkoxyalkyl, or alkanoyl, or formyl, carboxamido or thiocarboxamido; R.sup.4 and R.sup.5, which may be the same or different, are each --(CH.sub.2).sub.n Ar, where Ar is a monocyclic or bicyclic aryl group or monocyclic or bicyclic heteroaryl and n is integer of 0 to 3; R.sup.6 is hydrogen or substituted or unsubstituted alkyl; R.sup.7 is hydrogen or substituted or unsubstituted alkyl; and the salts, solvates, hydrates and N-oxides thereof.Type: GrantFiled: June 7, 1995Date of Patent: April 22, 1997Assignee: Celltech Therapeutics LimitedInventors: Graham J. Warrellow, Ewan C. Boyd, Rikki P. Alexander, John C. Head -
Patent number: 5618849Abstract: A compound represented by formula IAr.sub.1 --O--M--O--Ar.sub.2 Iwherein Ar.sub.1 and Ar.sub.2 are independently substituted phenyl or substituted pyridinyl, the substituents on said phenyl or pyridinyl being independently selected from one, two or three of (C.sub.1 -C.sub.10) alkyl, (C.sub.1 -C.sub.10) alkoxy, halogen, carbamyl, (C.sub.1 -C.sub.10) alkoxycarbonyl, oxazoyl, and (C.sub.1 -C.sub.10) alkyl substituted by halogen, (C.sub.1 -C.sub.10) alkoxy, hydroxy, or (C.sub.1 -C.sub.10) alkoxycarbonyl; ##STR1## (C.sub.4 -C.sub.8) alkylene, (C.sub.4 -C.sub.8) alkenylene or (C.sub.4 -C.sub.8)-alkynylene;O is oxygen;or pharmaceutically acceptable salts thereof.as well as pharmaceutical compositions containing the compounds and methods of treating or preventing viral infections, especially picornaviral infections, are disclosed.Type: GrantFiled: May 19, 1995Date of Patent: April 8, 1997Assignee: Schering CorporationInventors: Viyyoor M. Girijavallabhan, Ashit K. Ganguly, Richard W. Versace
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Patent number: 5618931Abstract: Compounds of the formula ##STR1## wherein the symbols have the meaning described in the specification have retinoid-like biological activity.Type: GrantFiled: December 29, 1994Date of Patent: April 8, 1997Assignee: AllerganInventors: Richard L. Beard, Min Teng, Alan T. Johnson, Vidyasagar Vuligonda, Roshantha A. Chandraratna
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Patent number: 5618821Abstract: Compounds of the formula ##STR1## wherein Q is chosen from the group consisting of pyridyl, pyrazyl, pyrimidyl, quinolyl, indolyl and 7-azaindolyl or any of these substituted with one or two substituents;Y is an alkylene bridge of 3-9 carbon atoms;R.sub.1 and R.sub.2 are each independently chosen from hydrogen, halo, alkyl, alkenyl, amino, alkylthio, hydroxy, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkoxy, nitro, carboxy, alkoxycarbonyl, dialkylaminoalkyl, alkylaminoalkyl, aminoalkyl, difluoromethyl, trifluoromethyl or cyano;R.sub.3 is alkoxycarbonyl, alkyltetrazolyl, substituted or unsubstituted phenyl or heterocyclyl, the N-oxide thereof, or a pharmaceutically acceptable acid addition salt thereof is an effective antipicornaviral agent.Type: GrantFiled: May 26, 1995Date of Patent: April 8, 1997Assignee: Sanofi, S.A.Inventors: David J. Aldous, Thomas R. Bailey, Guy D. Diana, Gee-Hong Kuo, Theodore J. Nitz
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Patent number: 5614548Abstract: Quaternary amine-containing ether lipid analogs of the formulaR.sub.1 --X--R.sub.2 --N.sup.+ (R.sub.3) (R.sub.4) (R.sub.5) Z.sup.-are disclosed. R.sub.1 represents a hydrophobic group and R.sub.2 represents the backbone of the molecule, with the quaternary amine being linked directly to the backbone. Pharmaceutical compositions including these compounds and methods of combating tumors with these compounds are disclosed. Also disclosed is a method of combating viral infections with both these compounds and ET-18-OMe and its analogs.Type: GrantFiled: September 8, 1994Date of Patent: March 25, 1997Assignee: Wake Forest UniversityInventors: Claude Piantadosi, Khalid S. Ishaq, Canio J. Marasco, Jr., Larry W. Daniel, Louis S. Kucera, Edward J. Modest, Barry P. Goz
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Patent number: 5614634Abstract: Leukotriene-B.sub.4 analogs of formula I ##STR1## in which R.sup.1 means radical COOR.sup.2 with R.sup.2 meaning a hydrogen atom or a (C.sub.1 -C.sub.4)-alkyl group or R.sup.1 means radical CH.sub.2 OH,B means an alkylene group with 1-3 C atoms in the chain, a radical ##STR2## or a radical ##STR3## with R.sup.3 meaning a hydrogen atom, a carboxy or methoxycarbonyl group, A means groups ##STR4## --NH--CO--, --CO--NH--, --OCH.sub.2 --, --CH.dbd.CH--, --C.tbd.C--, --COCH.sub.2 -- or --CHOH--CH.sub.2 --,X means N or CH,D means groups or ##STR5## and . . . . . means a single or double bond, as well as optionally their salts with physiologically harmless bases, process for their production and their pharmaceutical use.Type: GrantFiled: June 5, 1995Date of Patent: March 25, 1997Assignee: Schering AktiengesellschaftInventors: Josef Heindl, Werner Skuballa, Bernd Buchmann, Wolfgang Frohlich, Roland Ekerdt, Claudia Giesen
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Patent number: 5610310Abstract: The present invention describes novel cyclic diol derivatives represented by formula I and II: ##STR1## in which Y represents O, S, SO, SO.sub.2, (CH.sub.2).sub.m wherein m is zero or an integer of 1 to 5, or NR.sup.a group wherein R.sup.a is hydrogen, lower alkyl, lower alkoxycarbonyl, aryl, arylalkyl or acyl;R.sup.1 represents an alkyl or alkylcarbamoyl group;R.sup.2 represents a group having formula T--(CH.sub.2).sub.n --V (X.sup.-)q, wherein T refers to a simple covalent bond, a CO, PO.sub.3.sup.-, C(O)O, or CONR.sup.b group wherein R.sup.b is hydrogen, lower alkyl or acyl;n refers to an integer of from 1 to 10;V represents either (i) the group indicated by formula --.sup.+ NR.sup.5 R.sup.6 R.sup.7 wherein R.sup.5, R.sup.6 and R.sup.7 stands for identical or different lower alkyl group, or two or three of R.sup.5, R.sup.6 and R.sup.7 taken together with the adjacent nitrogen form heterocyclic ammonio group, or (ii) the group indicated by the formula ##STR2## wherein R.sup.Type: GrantFiled: June 7, 1995Date of Patent: March 11, 1997Assignees: Pohang Iron & Steel Co., Ltd, Research Institute of Industrial Science & TechnologyInventors: Soon H. Woo, Sung K. Chung, Soo H. Ban, Byoung E. Kim, Si H. Kim
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Patent number: 5608071Abstract: Compounds of the formula ##STR1## which are intermediates in the preparation of hydantoin aldose reductase inhibitors and methods of preparing these intermediates.Type: GrantFiled: April 26, 1995Date of Patent: March 4, 1997Assignee: Pfizer Inc.Inventor: George J. Quallich
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Patent number: 5605915Abstract: Compounds of the formula ##STR1## wherein the symbols have the meaning defined in the specification.Type: GrantFiled: May 31, 1996Date of Patent: February 25, 1997Assignee: AllerganInventors: Vidyasagar Vuligonda, Richard L. Beard, Alan T. Johnson, Min Teng, Tae K. Song, Roshantha A. Chandraratna
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Patent number: 5596008Abstract: A class of substitute pyridyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula I ##STR1## wherein R.sup.1 is haloalkyl; wherein R.sup.2 is aryl optionally substituted at a substitutable position with one or more radicals independently selected from alkylsulfinyl, alkyl, cyano, carboxyl, alkoxycarbonyl, haloalkyl, hydroxyl, hydroxyalkyl, haloalkoxy, amino, alkylamino, arylamino, nitro, halo, alkoxy and alkylthio; wherein R.sup.3 is aryl substituted at a substitutable position with a radical selected from alkylsulfonyl and sulfamyl; and wherein R.sup.4 is selected from halo, alkoxy and alkynyloxy; or a pharmaceutically-acceptable salt thereof.Type: GrantFiled: February 10, 1995Date of Patent: January 21, 1997Assignee: G. D. Searle & Co.Inventor: Len F. Lee
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Patent number: 5589103Abstract: A mesomorphic compound of the formula (I) according to claim 1 is suitable as a component for a liquid crystal composition providing improved response speed and decreased. The mesomorphic compound of the formula (I) is characterized by having at least one terminal cyclic group free from a side chain and also having a core structure including at least one group ##STR1## The above liquid crystal composition is useful as an element of a liquid crystal device and a display apparatus providing a good display characteristics.Type: GrantFiled: January 4, 1994Date of Patent: December 31, 1996Assignee: Canon Kabushiki KaishaInventors: Yoko Yamada, Takao Takiguchi, Takashi Iwaki, Takeshi Togano, Shinichi Nakamura, Ikuo Nakazawa
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Patent number: 5580888Abstract: Compounds of general formula (1) ##STR1## are described wherein Y is a halogen atom or a group --OR.sup.1, wherein R.sup.1 is an optionally substituted alkyl group; X is --O--, --S-- or --N(R.sup.6)--, where R.sup.6 is a hydrogen atom or an alkyl group; R.sup.2 is an optionally substituted alkyl, alkenyl, cycloalkyl or cycloalkenyl group; R.sup.3 and R.sup.4, which may be the same or different, is each a group --(CH.sup.2).sub.n Ar, where Ar is a monocyclic or bicyclic aryl group optionally containing one or more heteroatoms selected from oxygen, sulphur or nitrogen atoms and n is zero or an integer 1, 2 or 3; R.sup.5 is a hydrogen atom or an optionally substituted alkyl group; and the salts, solvates, hydrates and N-oxides. Compounds according to the invention are potent, selective and orally active PDE IV inhibitors and are useful in the prophylaxis and treatment of asthma.Type: GrantFiled: June 5, 1995Date of Patent: December 3, 1996Assignee: Celltech Therapeutics LimitedInventors: Graham J. Warrellow, Ewan C. Boyd, Rikki P. Alexander
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Patent number: 5571449Abstract: Partially fluorinated benzene derivatives of the formula I ##STR1## in which R, A.sup.1, A.sup.2, Z.sup.1, Z.sup.2, L.sup.1, L.sup.2 and m are as defined in claim 1, are suitable as components of liquid-crystalline media.Type: GrantFiled: January 19, 1995Date of Patent: November 5, 1996Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Ekkehard Bartmann, Herbert Plach, Rudolf Eidenschink
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Patent number: 5559133Abstract: A compound represented by formula I, Ar.sub.1 --O--M--O--Ar.sub.2, wherein Ar.sub.1 and Ar.sub.2 are independently substituted phenyl or substituted pyridinyl, the substituents on said phenyl or pyridinyl being independently selected from one, two or three of (C.sub.1 -C.sub.10) alkyl, (C.sub.1 -C.sub.10) alkoxy, halogen, carbamyl, (C.sub.1 -C.sub.10) alkoxycarbonyl, oxazoyl, and (C.sub.1 -C.sub.10) alkyl substituted by halogen, (C.sub.1 -C.sub.10) alkoxy, hydroxy, or (C.sub.1 -C.sub.10) alkoxycarbonyl; ##STR1## O is oxygen; R' is (C.sub.1 -C.sub.3 alkyl or H; A is oxygen or sulfur; Q is selected from hydrogen, halogen, nitro, (C.sub.1 -C.sub.6) alkyl, (C.sub.1 C.sub.6) perhaloalkyl, (C.sub.1 -C.sub.6) alkylthio (C.sub.1 -C.sub.Type: GrantFiled: December 16, 1993Date of Patent: September 24, 1996Assignee: Schering CorporationInventors: Viyyoor M. Girijavallabhan, Ashit K. Ganguly, Richard W. Versace, Anil K. Saksena, Patrick A. Pinto
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Patent number: 5554641Abstract: The small nonpeptides of the instant invention are tachykinin antagonists. The compounds are highly selective and functional NK.sub.3 antagonists expected to be useful in the treatment of pain, depression, anxiety, panic, schizophrenia, neuralgia, addiction disorders, inflammatory diseases, gastrointestinal disorders, vascular disorders, and neuropathological disorders.Type: GrantFiled: March 20, 1995Date of Patent: September 10, 1996Inventors: David C. Horwell, Martyn C. Pritchard, Jennifer Raphy
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Patent number: 5554758Abstract: A compound of the formula:A--CH.sub.2 CH.sub.2 --O--B[wherein A stands for an aromatic ring residue, a group shown by R.sup.1 --CO-- (wherein R.sup.1 stands for an aliphatic hydrocarbon residue, aromatic hydrocarbon residue, a heterocyclic residue, an aromatic alipahtic hydrocarbon residue or an alicyclic hydrocarbon residue) or R.sup.2 --CH.dbd.CH-- (wherein R.sup.2 stands for an aliphatic hydrocarbon residue an aromatic hydrocarbon residue a heterocyclic residue an aromatic aliphatic hydrocarbon residue or an alicyclic hydrocarbon residue), and B stands for an aromatic ring residue], can be obtained in high yield, at high purity level by short reaction time, by reacting a compound of the formula:A--CH.sub.2 CH.sub.2 --X(wherein A is of the same meaning as defined above, and X stands for a leaving group) with a compound represented by the general formula:MO--B(wherein M stands for an alkali metal atom or an alkaline earth metal atom and B is of the same meaning as defined above) in a non-aqueous solvent.Type: GrantFiled: June 7, 1995Date of Patent: September 10, 1996Assignee: Takeda Chemical Industries, Ltd.Inventors: Yukio Mizuno, Miichiro Arita
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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