Rings Bonded Directly To Each Other In Acid Moiety Patents (Class 560/102)
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Patent number: 5952386Abstract: The present invention provides dihalopropene compounds of the general formula: ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.10 alkyl or the like; L is C(.dbd.O)NH or the like; R.sub.2, R.sub.3 and R.sub.4 are independently halogen or the like; R.sub.5, R.sub.6 and R.sub.7 are independently hydrogen or the like; m is an integer of 0 to 4; n is an integer of 0 to 2; X is chlorine or the like; Y is oxygen or the like; and Z is oxygen or the like, which have excellent insecticidal activity so that they are satisfactorily effective for the control of noxious insects.Type: GrantFiled: September 24, 1997Date of Patent: September 14, 1999Assignee: Sumitomo Chemical Company, LimitedInventors: Sanshiro Matsuo, Taro Hirose, Keiichi Izumi, Masaya Suzuki, Noriyasu Sakamoto, Kazunori Tsushima, Shigeru Saito, Hirotaka Takano
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Patent number: 5945561Abstract: Certain novel substituted (5,6)-dihydroanthracenyl compounds of the general formula ##STR1## wherein A, n, p, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are as defined in the specification exhibit retinoid-like properties and are particularly useful in the prevention of post-surgical adhesions.Type: GrantFiled: April 24, 1998Date of Patent: August 31, 1999Assignee: Bristol-Myers Squibb CompanyInventors: John E. Starrett, Jr., Kenneth M. Tramposch, Xina Nair, Peter R. Reczek, Anna Ericsson, Anne Marinier, Alain Martel, Fred C. Zusi
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Patent number: 5922901Abstract: It is contemplated to provide an industrially adapted method for producing a dimerization product of acrylonitrile, which method is capable of producing a straight chain dimer of acrylonitrile efficiently at a high yield in a simple manner using a highly active catalyst exhibiting superior stability, without suffering from occurrence of difficulty removable by-products. In the method according to the present invention, acrylonitrile is subjected to dimerization in the presence of a ruthenium complex composed of a central atom of ruthenium and ligands including cyclopentadiene or its derivative coordinating thereto. The dimerization product, such as adiponitrile, 1,4-dicyanobutene or 1,4-dicyanobutadiene, is useful as an intermediate for producing hexamethylenediamine and adipic acid, both serving for the starting material of nylon 66, or as an intermediate for producing, for example, an antirusting agent and a vulcanization accelerator for rubbers.Type: GrantFiled: February 26, 1997Date of Patent: July 13, 1999Assignee: Mitsui Chemicals, Inc.Inventors: Yasuhiko Suzuki, Yoshihisa Kiso
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Patent number: 5922898Abstract: The present invention provides a process for preparing biaryl compounds comprising reacting an arylmetal reagent selected from arylmagnesium reagents and aryllithium reagents with an arylhalide in the presence of a catalyst system comprising a catalyst selected from nickel catalysts and palladium catalysts and a cocatalyst selected from zinc cocatalysts and cadmium cocatalysts. The present invention specifically provides a process for the preparation of 2-(4'-methylphenyl)benzonitrile comprising reacting a 4-methylphenylmagnesium reagent with a 2-halobenzonitrile in the presence of a catalyst system comprising a catalyst selected from nickel catalysts and palladium catalysts and a zinc cocatalyst.Type: GrantFiled: November 7, 1997Date of Patent: July 13, 1999Assignee: Catalytica Pharmaceuticals, Inc.Inventors: Joseph Arthur Miller, Robert Patrick Farrell
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Patent number: 5877342Abstract: Novel pharmaceutically/cosmetically-active adamantyl-substituted biaromatic compounds have the structural formula (I): ##STR1## wherein Ar is a radical having one of the formulae (a')-(f'): ##STR2## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular, bone and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.Type: GrantFiled: December 2, 1996Date of Patent: March 2, 1999Assignee: Centre International De Recherches Dermatologiquies GaldermaInventors: Jean-Michel Bernardon, Bruno Charpentier
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Patent number: 5874608Abstract: The present invention relates to a process for the preparation of compounds of the formula (1)R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 ArCOOR (1)in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are hydrogen, a halogen, an alkyl or alkoxy group having 1 to 6 carbon atoms or OR, NHR, NR.sub.2, SR or COOR, in which R is an alkyl radical having 1 to 4 carbon atoms, Ar is an aryl radical having 6 to 12 carbon atoms and the radical R shown in formula (1) has the above meaning, by reacting a compound of the formula (2)R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 ArCOOH (2)in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are hydrogen, a halogen, an alkyl or alkoxy group having 1 to 6 carbon atoms, OH, NH.sub.2, NHR, SH or COOH and Ar has the same meaning as in formula (1), with a sulfate of the formula (RO).sub.2 SO.sub.2, in which R has the above meaning, in the presence of a water-insoluble tertiary amine and water at a temperature of 10.degree.Type: GrantFiled: May 19, 1997Date of Patent: February 23, 1999Assignee: Hoechst AktiengesellschaftInventors: Ralf Pfirmann, Theodor Papenfuhs
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Patent number: 5856557Abstract: A 2,2',5,5',6,6'-hexafluorobiphenyl-3,3',4,4'-tetracarboxylic acid precursor as an intermediate material for a highly functional fluororesin may be produced at a high yield by reacting tetrafluorophthalonitrile with an alkali metal iodide.Type: GrantFiled: June 12, 1997Date of Patent: January 5, 1999Assignee: Ube Industries, Ltd.Inventors: Yumiki Noda, Takashi Honma
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Patent number: 5851427Abstract: Photocross-linkable naphthyl derivatives include compounds of the formula: ##STR1## wherein R.sup.1 and R.sup.2 each independently signify a cross-linkable group;S.sup.1 and S.sup.2 signify --(CY.sub.2).sub.m -, --O(CY.sub.2).sub.m -, --(CY.sub.2).sub.m O--, --(CY.sub.2).sub.m COO--, --(CY.sub.2).sub.m OOC--, --(Si?(CH.sub.3).sub.2 !O).sub.m -, --OCH.sub.2 (Si?(CH.sub.3).sub.2 !O).sub.m Si?(CH.sub.3).sub.2 !CH.sub.2 O-- or --NHCH.sub.2 (Si?(CH.sub.3).sub.2 !O).sub.m Si?(CH.sub.3).sub.2 !CH.sub.2 NH--;Y signifies hydrogen, fluorine or methyl;a signifies 0 or 1;b signifies 1 or 2, with the proviso that a+b=2;m signifies a whole number of 1 to 16;A.sup.1 and A.sup.2 each independently signify 1,4-phenylene, which is optionally mono- or multiply-substituted with halogen, cyano, methyl, methoxy and/or acetyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, trans-1,4-cyclohexylene or trans-1,3-dioxane-2,5-diyl; andZ.sup.1 and Z.sup.2 each independently signify a single bond, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.Type: GrantFiled: February 23, 1996Date of Patent: December 22, 1998Assignee: Rolic AGInventor: Stephen Kelly
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Patent number: 5851424Abstract: The present invention is concerned with photo cross-linkable liquid crystalline compounds of the general formula ##STR1## wherein A.sup.1 and A.sup.2 each represent a cross-linkable, mesogenic residue,liquid crystalline mixtures which contain such compounds and their use in the cross-linked state as optical components.Type: GrantFiled: July 25, 1996Date of Patent: December 22, 1998Assignee: Rolic AGInventor: Stephen Kelly
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Patent number: 5837163Abstract: A liquid crystal compound represented by formula (I): ##STR1## wherein R.sub.1 represents an alkyl group having from 3 to 18 carbon atoms; R.sub.2 represents an alkyl group having from 3 to 18 carbon atoms; X represents ##STR2## Y represents ##STR3## (A) and (B) each represents a group selected from the group consisting of ##STR4## and ##STR5## and * indicates an optically active center.Type: GrantFiled: September 30, 1992Date of Patent: November 17, 1998Assignee: Showa Shell Sekiyu K.K.Inventors: Koichi Numazawa, Noriko Yamakawa, Yoshiichi Suzuki, Ichiro Kawamura
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Patent number: 5820785Abstract: Disclosed are derivatives of fluoroalkylethynyl- and difluoroalkylethynylbenzenes of the formula (I) herein. These compounds exhibit useful properties as liquid crystal compounds and are useful in nematic liquid crystal mixtures.Type: GrantFiled: November 18, 1996Date of Patent: October 13, 1998Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Hubert Schlosser, Dietmar Jungbauer
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Patent number: 5808124Abstract: Compounds of the formula ##STR1## where the symbols have the meaning described in the application, have retinoid-like or retinoid antagonist-like biological activity.Type: GrantFiled: June 21, 1996Date of Patent: September 15, 1998Assignee: AllerganInventors: Richard L. Beard, Min Teng, Alan T. Johnson, Vidyasagar Vuligonda, Roshantha A. Chandraratna
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Patent number: 5800733Abstract: The present invention is concerned with photo cross-linkable liquid crystalline compounds in the formula ##STR1## wherein for example: A,B,C,D,E,F independently is pyridine-2,5-diyl, pyrimidine-2,5-diyl, trans-1,4-cyclohexylene, trans-1,3-dioxane-2,5-diylZ.sup.1, Z.sup.2, Z.sup.7 independently is --(CH.sub.2).sub.s O--, --COO--, --(CH.sub.2).sub.s COO--Z.sup.3, Z.sup.4, Z.sup.8 independently is a single bond, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O--Z.sup.5, Z.sup.6 independently is --(CH.sub.2).sub.s --m, n, q and r independently is 0, 1 or 2;s is a whole number of 1 to 16;R.sup.1, R.sup.2 independently is CH.sub.2 .dbd.CH--COO--, CH.sub.2 .dbd.C(CH.sub.3)--COO--R.sup.3 is H, CH, COOC.sub.n H.sub.2n+1, CnH.sub.2n+1 ; n=1 . . . 10X.sup.1, X.sup.2 and X.sup.3 independently is hydrogen, halogen, cyano or lower alkyl.The invention is also related to liquid crystalline mixtures and their use for electro-optical purpose.Type: GrantFiled: July 25, 1996Date of Patent: September 1, 1998Assignee: Rolic AGInventor: Stephen Kelly
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Patent number: 5792876Abstract: A process is described for producing acetals comprising reacting an aldehyde or a ketone with an alcohol in the presence of a titanium compound having an acetylacetone as a ligand, or in the presence of a compound selected from the group consisting of stannous chloride dihydrate, cerium chloride hexahydrate and bismuth chloride. The process can be used in the synthesis of unstable acetals or when water exists in the reaction mixture, and therefore the process can be used for a wide variety of applications.Type: GrantFiled: November 6, 1996Date of Patent: August 11, 1998Assignee: Kuraray Co., Ltd.Inventors: Hideharu Iwasaki, Masahiko Kitayama, Takashi Onishi
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Patent number: 5786379Abstract: Novel pharmaceutically/cosmetically-active adamantyl-substituted biaromatic compounds have the structural formula (I): ##STR1## wherein Ar is a radical having one of the formulae (a')-(f'): ##STR2## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular, bone and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.Type: GrantFiled: December 2, 1996Date of Patent: July 28, 1998Assignee: Centre International de Recherches Dermatologiques GaldermaInventor: Jean-Michel Bernardon
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Patent number: 5776977Abstract: Compounds of formula I, ##STR1## wherein the substituents R.sub.1 -R.sub.4 and a have the given meanings and show an activity against inflammatory conditions.Type: GrantFiled: August 5, 1996Date of Patent: July 7, 1998Assignee: Hoechst AktiengesellschaftInventors: Ramachandra Ganapati Naik, Vilas Narayan Mumbaikar, Rangarajan Vasumathy, Aftab Dawoodbhai Lakdawala, Mandakini Vithalrao Shirole, Bansi Lal, Jurgen Blumbach, Klaus Ulrich Weithmann, Robert Ryder Bartlett
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Patent number: 5760276Abstract: Compounds of the formula ##STR1## wherein the symbols have the meaning defined in the specification, have retinoid-like, retinoid antagonist or retinoid inverse agonist-like biological activity.Type: GrantFiled: March 6, 1997Date of Patent: June 2, 1998Assignee: AllerganInventors: Richard L. Beard, Alan T. Johnson, Min Teng, Vidyasagar Vuligonda, Roshantha A. Chandraratna
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Patent number: 5755994Abstract: A novel liquid crystalline compound having a large dielectric anisotropy value, a small change in the threshold voltage depending upon temperatures, and an improved solubility in other liquid crystal materials at low temperatures, and a liquid crystal composition containing the compound are provided,which liquid crystalline compound is expressed by the formula (1) ##STR1## wherein R is H or an alkyl group of 1 to 10C; l is an integer of 1 to 9; m, n and o are each independently 0 or 1; A.sub.1, A.sub.2 and A.sub.3 are each independently trans-1,4-cyclohexylene group, 1,4-phenylene group, one or more H atoms on the ring of which group may be replaced by F, or the like group; Z.sub.1, Z.sub.2 and Z.sub.3 are each independently --COO--, etc., but at least one of them is --COO--; X is CF.sub.3, etc.; and Y.sub.1, and Y.sub.2 are each independently H or F.Type: GrantFiled: February 22, 1996Date of Patent: May 26, 1998Assignee: Chisso CorporationInventors: Tomoyuki Kondo, Shuichi Matsui, Yasuyuki Koizumi, Koichi Shibata, Yasuhiro Haseba, Norihisa Hachiya, Etsuo Nakagawa, Kazutoshi Miyazawa
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Patent number: 5741438Abstract: Optically active biphenyl derivatives including optically active biphenyl carboxylic acid derivative, hydroxybiphenyl derivative, alkoxybiphenylalkanol derivative and alkoxybiphenylalkanol derivative have the following structural formula: ##STR1## wherein R.sup.1 represents an alkyl group of 3-20 carbon atoms, R.sup.2 represents an alkyl group or alkoxyalkyl group of 1-20 carbon atoms which may optionally be substituted with at least one halogen atom. X represents --O--, --COO-- or --OCO--, m represents 0 or 1, n represents an integer of 1-6 and p represents 0 or 1, and the * mark represents an asymmetric carbon atom. These optically active biphenyl derivatives are useful as a ferroelectric liquid crystal material or its component having a sufficient spontaneous polarization and by which a high speed response is possible and which further exhibits a ferroelectric liquid crystal phase in a temperature region around room temperature.Type: GrantFiled: May 30, 1995Date of Patent: April 21, 1998Assignee: Sumitomo Chemical Company, LimitedInventors: Isao Kurimoto, Takayuki Higashii, Shoji Toda, Masayoshi Minai, Chizu Sekine, Takeshi Tani
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Patent number: 5728864Abstract: A liquid crystal compound of the formula (1) ##STR1## wherein R is a linear alkyl group having 6 to 12 carbon atoms,both X and Y are hydrogen atoms or one of X and Y is a fluorine atom and the other is a hydrogen atom,A is --CF.sub.3 or --C.sub.2 F.sub.5,m is an integer of 2 to 4,n is an integer of 2 to 4, andC* is an asymmetric carbon,having a ferrielectric phase in its phase sequence, or a ferrielectric liquid crystal composition containing the liquid crystal compound of the formula (1) having a ferrielectric phase, may be injected between substrates provided with nonlinear active elements, such as thin film transistors or diodes formed on each pixel, to form an active matrix liquid crystal display device.Type: GrantFiled: April 12, 1996Date of Patent: March 17, 1998Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Yuki Motoyama, Tomoyuki Yui, Masahiro Johno, Maki Ito, Takahiro Matsumoto, Hiroshi Mineta
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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: 5700393Abstract: The present invention is concerned with photo cross-linkable liquid crystalline compounds of the general formula ##STR1## wherein A.sup.1 and A.sup.2 each are a cross-linkable mesogenic residue; andA.sup.3 is (R,R)- or (S,S)-trans-1,2-cyclohexyl-diyl,liquid crystalline mixtures which contain such compounds and their use in the cross-linked state as optical components.Type: GrantFiled: July 26, 1996Date of Patent: December 23, 1997Assignee: Rolic AGInventor: Stephen Kelly
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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: 5663416Abstract: 2-Phenylalkanoate esters which are useful as inhibitors of human leukocyte elastase.Type: GrantFiled: April 5, 1995Date of Patent: September 2, 1997Assignee: Cortech Inc.Inventors: Gary P. Kirschenheuter, Lyle W. Spruce, John C. Cheronis
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Patent number: 5648514Abstract: 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: July 15, 1997Assignee: AllerganInventors: Alan T. Johnson, Min Teng, Vidyasagar Vuligonda, Richard L. Beard, Samuel J. Gillett, Tien T. Duong, Roshantha A. Chandraratna
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Patent number: 5643948Abstract: Compounds having anti-inflammatory and other activities are disclosed. The compounds are derived from diterpenes of the phorbol-, resiniferonol- and ingenol-classes.Type: GrantFiled: September 13, 1993Date of Patent: July 1, 1997Assignee: Procyon Pharmaceuticals, Inc.Inventors: Paul E. Driedger, James Quick
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Patent number: 5643495Abstract: 1,2,2,2-Tetrafluoroethyl ethers of the formula IR--(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --Z.sup.2 A.sup.3 --O--CHF--CF.sub.3(I)are suitable as components of liquid-crystalline media whereinR is H, a substituted or unsubstituted alkyl or alkenyl radical having 1 to 15 carbon atoms,A.sup.1 and A.sup.2 are each, independently of one another, a(a) trans-1,4-cyclohexylene radicals and derivatives thereof in which, in addition, one or more non-adjacent CH.sub.2 groups is optionally replaced by --O-- and/or --S--,(b) 1,4-phenylene radicals and derivatives thereof in which, in addition, one or two CH groups is optionally replaced by N, or(c) radical from the group consisting of 1,4-cyclohexenylene, 1,4-bicyclo(2,2,2)octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl and 1,2,3,4-tetrahydronaphthalene-2,6-diyl,wherein radicals (a) and (b) are optionally substituted by one or two fluorine atoms,Z.sup.1 and Z.sup.2 are each, independently of one another, --CO--O--, --O--CO--, --CH.sub.Type: GrantFiled: September 12, 1995Date of Patent: July 1, 1997Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Ekkehard Bartmann, Ulrich Finkenzeller
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Patent number: 5618969Abstract: The present invention provides an industrially advantageous process for preparing a 2-alkyl-3-(biphenyl-4-yl)methyl-3H-imidazo[4,5-b]pyridine derivative represented by the following formula (II) which is a precursor of an antagonist against an angiotensin II receptor useful as an antihypertensive drug, a biphenyl derivative which is a precursor of the substituent of the pyridine derivative, a process for the preparation thereof, and an intermediate useful for the preparation of the biphenyl derivative: ##STR1##Type: GrantFiled: October 19, 1995Date of Patent: April 8, 1997Assignees: Eisai Co., Ltd., Eisai ChemicalInventors: Yoshio Urawa, Ken Furukawa, Toshikazu Shimizu, Yoji Yamagishi, Tomio Tsurugi, Tomio Ichino
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Patent number: 5618839Abstract: The present invention relates to a compound of formula I ##STR1## or a nontoxic pharmaceutically acceptable salt, physiologically hydrolyzable ester or solvate thereof, in whichX is --O--CO--, --NH--CO--, --CS--NH--, --CO--O--, --CO--NH--, --COS--, --SCO--, --SCH.sub.2 --, --CH.sub.2 --CH.sub.2 --, --C.tbd.C--, --CH.sub.2 --NH--, --COCH.sub.2 --, --NHCS--, --CH.sub.2 S--, --CH.sub.2 O--, --OCH.sub.2 --, --NHCH.sub.2 -- or --CR.sup.5 .dbd.CR.sup.6 --;R.sup.m and R.sup.k are independently hydrogen, halogen, C.sub.1-6 alkyl, hydroxy, C.sub.1-6 alkyloxy or nitro;n is zero or one;R.sup.4 is --(CH.sub.2).sub.t --Y, C.sub.1-6 alkyl, or C.sub.3-6 cycloalkyl;R.sup.1 is --CO.sub.2 Z, C.sub.1-6 alkyl, CH.sub.2 OH, --CONHR.sup.y, or CHO;R.sup.2 and R.sup.3 are independently hydrogen or C.sub.1-6 alkyl;R.sup.a and R.sup.b are independently hydrogen or C.sub.1-6 alkyl; but when n is one, R.sup.a and R.sup.Type: GrantFiled: May 2, 1996Date of Patent: April 8, 1997Assignee: Bristol-Myers Squibb CompanyInventors: John E. Starrett, Jr., Kuo-Long Yu, Muzammil M. Mansuri, David R. Tortolani, Peter R. Reczek
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Patent number: 5597839Abstract: Di(aromatic) compounds corresponding to the following formula: ##STR1## in which: Ar represents either ##STR2## X represents a divalent radical, Z represents O, S or a divalent radical,and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent a hydrogen atom or various organic radicals, and the salts of the compounds of formula (I) when R.sub.1 is a carboxylic acid function.Use in human and veterinary medicine and in cosmetics.Type: GrantFiled: April 28, 1995Date of Patent: January 28, 1997Assignee: Centre International de Recherches Dermatologiques Galderma (Cird Galderma)Inventors: Jean-Michel Bernardon, William R. Pilgrim
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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: 5557002Abstract: The present invention provides an industrially advantageous process for preparing a 2-alkyl-3-(biphenyl-4-yl)methyl-3H-imidazo[4,5-b]pyridine derivative represented by the following formula (II) which is a precursor of an antagonist against an angiotensin II receptor useful as an antihypertensive drug, a biphenyl derivative which is a precursor of the substituent of the pyridine derivative, a process for the preparation thereof, and an intermediate useful for the preparation of the biphenyl derivative: ##STR1## The 2-alkyl-3-(biphenyl-4-yl)methyl-3H-imidazo[4,5-b]pyridine derivative can be prepared in a high yield according to the present invention from a 2-amino-5-halogeno-3-nitropyridine derivative through amidation, N-alkylation and reductive cyclization. The halogen atom introduced at the 5-position as a protective group against nitration can be eliminated simultaneously in the step which is conducted thereafter. Thus, this process is industrially advantageous.Type: GrantFiled: June 6, 1995Date of Patent: September 17, 1996Assignees: Eisai Co., Ltd., Eisai Chemical Co., Ltd.Inventors: Yoshio Urawa, Ken Furukawa, Toshikazu Shimizu, Yoji Yamagishi, Tomio Tsurugi, Tomio Ichino
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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: 5536874Abstract: There is provided a process for preparing an arylacetic acid or arylpropionic acid divative from an arylcarbinol which comprises the step of subjecting said arylcarbinol to suitable carbonylation conditions for a sufficient period of time and under suitable pressure and temperature to form said acid derivative, with the proviso that said carbonylation conditions include conducting the reaction in a two-phase system wherein one phase is an aqueous medium which contains (1) a catalyst which is a water-soluble metal complex consisting essentially of a Group VIII metal and a hydrophilic ligand such as palladium complexed with trisulfonated triphenylphosphine, and (2) optionally an acid, and wherein the second phase comprises said arylcarbinol.Type: GrantFiled: November 30, 1994Date of Patent: July 16, 1996Assignee: Hoechst Celanese CorporationInventors: Roger A. Sheldon, Leendert Maat, Georgios Papadogianakis
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Patent number: 5514825Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen or alkyl of 1 to 10 carbons; R.sub.2 and R.sub.3 are hydrogen, or alkyl of 1 to 6 carbons and the substituted ethynyl group occupies either the 2 or the 3 position of the tetrahydronaphthalene nucleus; m is an integer having the value of 0-3; o is an integer having the value 0-4; Y is a phenyl group, or heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, and imidazolyl, said groups being optionally substituted with one or two R.sub.2 groups; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.13 O, --COR.sub.7, CR.sub.Type: GrantFiled: December 29, 1994Date of Patent: May 7, 1996Assignee: Allergan, Inc.Inventors: Vidyasagar Vuligonda, Min Teng, Richard L. Beard, Alan T. Johnson, Tien T. Duong, Yuan Lin, Roshantha A. Chandraratna
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Patent number: 5492917Abstract: Novel compounds of the general structural formula I: ##STR1## have endothelin antagonist activity and are therefore useful in treating cardiovascular disorders, such as hypertension, pulmonary hypertension, postischemic renal failure, vasospasm, cerebral and cardiac ischemia, myocardial infarction, endotoxic shock, inflammatory diseases including Raynaud's disease and asthma.Type: GrantFiled: September 29, 1993Date of Patent: February 20, 1996Assignee: Merck & Co., Inc.Inventors: Ralph A. Rivero, Peter D. Williams, Daniel F. Veber
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Patent number: 5486310Abstract: Optically active compounds of the formula ##STR1## wherein rings A, B and C each independently are unsubstituted or each are 1,4-phenylene substituted with at least one of halogen-, cyano-, methyl- or methoxy in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen; R.sup.1 is a radical of an optically active terpene alcohol after cleavage of the hydroxy group or a group --(CH.sub.2).sub.m --C*HX.sup.1 --R.sup.3 ; R.sup.2 is a radical of an optically active terpene alcohol after cleavage of the hydroxy group or a group --(CH.sub.2).sub.n --C*HX.sup.2 --R.sup.4 ; m and n each independently stand for the number 0 or 1: C* denotes a chiral carbon atom; X.sup.1 and X.sup.2 each independently are fluorine, chlorine, cyano, methyl or methoxy; R.sup.3 and R.sup.4 each independently denote a group R, phenyl or phenyl substituted with R, with the proviso that R.sup.3 is different from X.sup.1 and R.sup.4 is different from X.sup.Type: GrantFiled: February 18, 1994Date of Patent: January 23, 1996Assignees: Hoffmann-La Roche Inc., Niopic Moscow Research and Production AssociationInventors: Richard Buchecker, Nina I. Chernova, Alexander V. Ivaschenko, Marina V. Loseva, Olga S. Petrashevich, Evgeniy P. Pozhidaev, Arnold Z. Rabinovich, Martin Schadt
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Patent number: 5476965Abstract: Provided are enzymatic methods for the selective hydrolytic resolution of certain enantiomers of a pharmaceutical compound, the pharmaceutical compound comprising a (.+-.) mixture of a .alpha.-substituted 2-methyl proprionic acid derivative. Specifically provided is the selective enzymatic resolution of either the R(+) or S(-) enantiomer of (.+-.)-ethyl ciprofibrate. Also provided are substantially pure enantiomers of R(+) and S(-) ciprofibrate.Type: GrantFiled: February 18, 1994Date of Patent: December 19, 1995Assignee: Genencor International, Inc.Inventors: Matthew W. Chase, Charles T. Goodhue, Robert Seemayer, Gregory M. Whited
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Patent number: 5475132Abstract: R.sub.3, R.sub.4 and R.sub.5, each represents a hydrogen or halogen atom (at least one of R.sub.3, R.sub.4 and R.sub.5 being other than hydrogen or halogen); optionally substituted amino; optionally halogenated or hydroxylated alkyl, alkoxy, alkylalkoxy or alkylthio; or R.sub.3 and R.sub.4 (in the 3- and 4-positions) can together form a single divalent radical with 3 or 4 members containing 1 or 2 non-adjacent oxygen atoms; are useful as agricultural fungicides.Type: GrantFiled: May 27, 1994Date of Patent: December 12, 1995Assignee: Rhone-Poulenc AgrochimieInventors: Regis Pepin, Christian Schmitz, Guy-Bernard Lacroix, Philippe Dellis, Christine Veyrat
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Patent number: 5472970Abstract: Allylaminoesters of the formula (I): ##STR1## in which: R.sub.1 is H or low-molecular-weight alkyl,R.sub.2 is low-molecular-weight alkyl, cycloalkyl, or low-molecular-weight phenylcycloalkyl, pyridyl or phenyl, low-molecular-weight phenylalkyl, low-molecular-weight diphenylalkyl, low-molecular-weight phenylalkenyl, in which the phenyl cycle may be mono-, di- or trisubstituted by chlorine atoms, low-molecular-weight alkyl radicals, low-molecular-weight alkoxy, or trifluoromethyl, acetamide or acetyloxy radicals, their racemic forms, their (S) enantiomers and their addition salts. Also, antiallergic drugs containing the same.Type: GrantFiled: September 19, 1994Date of Patent: December 5, 1995Assignee: Institut de Recherche Jouveinal S.A.Inventors: Alain P. Calvet, Agnes G. Grouhel, Jean-Louis Junien
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Patent number: 5458806Abstract: Fluoromethyl ketones of the formula I ##STR1## are suitable as components of liquid-crystalline media wherein R is H, a substituted or unsubstituted alkyl or alkenyl radical having 1 to 15 carbon atoms,A.sup.1 and A.sup.2 are each, independently of one another, a(a) trans-1,4-cyclohexylene radicals and derivatives thereof in which, in addition, one or more non-adjacent CH.sub.2 groups is optionally replaced by --O-- and/or --S--,(b) 1,4-phenylene radicals and derivatives thereof in which, in addition, one or two CH groups is optionally replaced by N, or(c) radical from the group consisting of 1,4-cyclohexenylene, 1,4-bicyclo(2,2,2)octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl and 1,2,3,4-tetrahydronaphthalene-2,6-diyl,wherein radicals (a) and (b) are optionally substituted by one or two fluorine atoms,Z.sup.1 and Z.sup.2 are each, independently of one another, --CO--O--, --O--CO--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --C.tbd.Type: GrantFiled: May 4, 1994Date of Patent: October 17, 1995Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Ekkehard Bartmann, Herbert Plach
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Patent number: 5454974Abstract: Compounds of the formula ##STR1## wherein X.sup.1 denotes fluorine or chlorine and X.sup.2 denotes hydrogen, fluorine or chlorine; R.sup.1 is 3E-alkenyl, 4-alkenyl, 2E-alkenyloxy or 3-alkenyloxy; n stands for the number 0 or 1; one of the groups Y.sup.1 and Y.sup.2 is a single covalent bond, --COO--, --OOC--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O-- or --OCH.sub.2 -- and the other of the groups Y.sup.1 and Y.sup.2 is a single covalent bond; and rings A.sup.1 and A.sup.2 each individually are substituted or unsubstituted trans-1,4-cyclohexylene, in which optionally 2 non-adjacent CH.sub.2 groups are replaced by oxygen, or substituted or unsubstituted 1,4-phenylene, in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen; with the proviso that X.sup.2 denotes fluorine or chlorine and/or Y.sup.1 or Y.sup.2 denotes --CH.sub.2 O-- or --OCH.sub.2 -- when simultaneously X.sup.1 is fluorine and R.sup.1 is 3E-alkenyl,and their use for liquid crystalline mixtures and electro-optical purposes.Type: GrantFiled: January 6, 1994Date of Patent: October 3, 1995Assignee: Hoffmann-La Roche Inc.Inventors: Arthur Boller, Richard Buchecker, Martin Schadt, Alois Villiger
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Patent number: 5447659Abstract: Disclosed are novel active benzene derivatives represented by the general formula (I): ##STR1## (wherein X represents --CCO--, --OCO--, --CH.sub.2 C-- or --OCH.sub.2 --; A represents a hydrogen atom, a halogen atom or an alkyl or alkoxyl group having 1 to 20 carbon atoms; R represents an alkyl group having 1 to 20 carbon atoms; l and m each represents a number of 1 or 2, n represents a number of 0 or 1, but when n is 0 the sum of l and m is 3 or less; and * indicates asymmetric carbon atom), a process for producing the same, liquid-crystalline substances containing said derivatives as active ingredient, and optical switching elements utilizing the liquid crystal compositions containing said liquid-crystalline substances.Type: GrantFiled: May 31, 1994Date of Patent: September 5, 1995Assignee: Sumitomo Chemical Company, LimitedInventors: Takayuki Higashii, Masayoshi Minai
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Patent number: 5434302Abstract: The present process is directed to preparing optically active 2-aryl alkyl aldehydes by various processes through the use of an optically active amine, (-)-2'-amino-3-phenyl propane. The aldehyde formed can then be oxidized to produce the corresponding acid.Type: GrantFiled: February 18, 1994Date of Patent: July 18, 1995Inventor: H. Henrich Paradies
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Patent number: 5424005Abstract: A composition of (R)-isomer and (S)-isomer of a liquid crystal compound represented by the formula; ##STR1## wherein X represents --O-- or a direct bond, Z represents a halogen-substituted alkyl group selected from a group consisting of --CF.sub.3, --CHF.sub.2, --CH.sub.2 F, --C.sub.2 F.sub.5, --CClF.sub.2, -CCl.sub.2 F, --CCl.sub.2 CF.sub.3, and --C.sub.3 F.sub.7, m represents an integer of from 1 to 20, n represents an integer of from 1 to 20, and * represents an asymmetric carbon, and the optical purity of said composition is high enough to exhibit optically tristable states in S*(3) phase when electric voltage is applied.Type: GrantFiled: June 30, 1992Date of Patent: June 13, 1995Assignee: Showa Shell Sekiyu K.K.Inventors: Yoshiichi Suzuki, Hiroyuki Mogamiya, Ichiro Kawamrua
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Patent number: 5424414Abstract: Novel tethered hapten intermediates and related conjugates based on 3- phenyl-1-adamantaneacetic acid, as well as methods for making and using such conjugates. Haptens based on the above core structure may be substituted at any position on the phenyl ring, especially at the para position. Using tethered intermediates, immunogens, tracers, solid supports and labeled oligonucleotides are all described; as are methods for using the intermediates to prepare the conjugates, methods of using the conjugates to make and purify anitbodies, as assay tracers, and in nucleic acid hybridization assays. Kits containing haptenated oligonucleotides and anti-hapten conjugates are also described.Type: GrantFiled: April 21, 1993Date of Patent: June 13, 1995Assignee: Abbott LaboratoriesInventor: Philip G. Mattingly
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Patent number: 5418254Abstract: A class of 2,3-substituted cyclopenta-2,4-dienyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula II: ##STR1## wherein each of R.sup.1 and R.sup.2 is independently selected from hydrido, lower alkyl, lower hydroxyalkyl, halo, lower haloalkyl, lower alkoxycarbonyl and carboxyl; and wherein each of R.sup.3 through R.sup.12 is independently selected from hydrido, halo, lower alkyl, lower alkylthio, cyano, hydroxyl, mercapto, lower haloalkyl, lower haloalkoxy, lower alkoxy, lower hydroxyalkyl, lower alkoxyalkyl, lower alkylsulfonyl, lower haloalkylsulfonyl and sulfamyl; provided R.sup.5 and R.sup.10 are not both hydrido or methoxy; or a pharmaceutically suitable salt or prodrug thereof.Type: GrantFiled: May 4, 1994Date of Patent: May 23, 1995Assignee: G. D. Searle & Co.Inventors: Horng-Chih Huang, David R. Reitz
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Patent number: 5416243Abstract: Cyclofluoralkylated fullerene compounds are prepared by reacting the fullerenes with a fluoroalkene as exemplified by tetrafluoroethylene or perfluoromethyl vinyl ether under thermolysis conditions as exemplified by temperatures of 200.degree. C., pressure and a halocarbon solvent, the products being useful as lubricants or additive thereto as well as in cooling systems, adhesives and polymers.Type: GrantFiled: August 29, 1994Date of Patent: May 16, 1995Assignee: E. I. DuPont de Nemours and CompanyInventors: Paul G. Bekiarian, Paul J. Fagan, Paul J. Krusic
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Patent number: 5391817Abstract: Certain novel biaryl compounds are effective phospholipase A.sub.2 (PLA.sub.2) inhibitors.Type: GrantFiled: December 21, 1993Date of Patent: February 21, 1995Assignee: Bristol-Myers SquibbInventors: Dane Springer, Bing-Yu Luh, Katharine M. Greene, Joanne J. Bronson, Muzammil M. Mansuri
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Patent number: 5391650Abstract: A compound having at least one 2-hydroxy-1,3-propylidene, 2-acetoxy-1,3-propylidene, or 2-alkoxy-1,3-propylidene moiety between two benzocyclobutene end moieties is prepared by (a) contacting a diepoxide species with a benzocyclobutene species containing a functionality capable of reacting with an epoxy group, (b) contacting an epoxy-containing benzocyclobutene species with a species containing two functionalities capable of reacting with an epoxy group, (c) contacting an epoxy-containing benzocyclobutene species with a benzocyclobutene species containing a functionality capable of reacting with an epoxy group, (d) contacting epichlorohydrin with benzocyclobutene species capable of reacting with an epoxy group, or (e) contacting epihalohydrin with benzocyclobutene species and difunctional species, wherein both species contain functionalities capable of reacting with epoxy groups.Type: GrantFiled: December 30, 1992Date of Patent: February 21, 1995Assignee: The Dow Chemical CompanyInventors: David J. Brennan, Jerry E. White, Daniel M. Scheck, Robert A. Kirchhoff, Charles Z. Hotz