Benzene Ring Bonded Directly To The Cyano Group Patents (Class 558/411)
  • Patent number: 5723621
    Abstract: 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: Grant
    Filed: May 14, 1996
    Date of Patent: March 3, 1998
    Assignee: Chisso Corporation
    Inventors: Koichi Shibata, Shuichi Matsui, Kazutoshi Miyazawa
  • Patent number: 5695686
    Abstract: Brightener mixtures containing from 75% by weight to 100% by weight, based on the weight of the mixture, of the bisstyryl compounds of the formulae I and II ##STR1## in a weight ratio from 10:90 to 70:30, formulations containing the novel mixtures, and also their use for optically brightening synthetic, semisynthetic or natural polymer materials.
    Type: Grant
    Filed: March 13, 1996
    Date of Patent: December 9, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Manfred Hauptreif, Norbert Leppert, Karl-Heinz Etzbach, Helmut Reichelt, Peter Raatz, Manfred Herrmann
  • Patent number: 5688945
    Abstract: The present invention relates to novel derivatives of 3-hydroxyanthranilic acid, 3-HANA, of the general formula I ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and selected from H and alkyl; X is selected from alkylthio, arylthio, aryloxy, halogen and cyano; R.sup.3, R.sup.4 are the same or different and selected from halogen, methyl, fluoroalkyl, cyano and Z--R.sup.5 wherein Z is selected from CH.sub.n, NH.sub.m, O, S, SO.sub.2 and CO wherein n=1 or 2; m=0 or 1 and R.sup.5 is selected from alkyl, aryl and fluoroalkyl; or R.sup.3 and R.sup.4 together form a saturated or unsaturated ring system Y--V--Z wherein Y and Z, independently of each other, are as defined for Z above and V is selected from C.sub.1 -C.sub.3 alkylene or alkenylene, --N.dbd., --N.dbd.N-- and ##STR2## wherein R.sub.
    Type: Grant
    Filed: December 20, 1996
    Date of Patent: November 18, 1997
    Assignees: Astra Aktiebolag, The University of Maryland at Baltimore
    Inventors: Susanna Karin Maria Bjork, Birgitta Kristina Gotthammar, Mats Torbjorn Linderberg, Johan Per Luthman, Kerstin Margareta Irma Persson, Robert Schwarcz
  • Patent number: 5686639
    Abstract: The invention relates to divalent immonium salts which are near infrared dyes of the formula (I).(R.sub.2 NAr).sub.2 --N.sup.+ .dbd.Ar'.dbd.N.sup.+ R.sub.2 +2X.sup.-(I)wherein:R.dbd.C.sub.1 to C.sub.6 alkyl; Ar=divalent phenyl which may or may not be ring substituted with one or more alkyl, alkoxy, halogen, nitro, cyano or carboalkoxy groups; Ar'=quinoidal phenyl which may or may not be ring substituted with one or more alkyl, alkoxy, halogen, nitro, cyano or carboalkoxy groups; and X=an anion of a strong acid. A double charged dye cation having an SbF.sub.6 anion associated with the dye can act both a near IR dye and an epoxy curative.
    Type: Grant
    Filed: April 20, 1995
    Date of Patent: November 11, 1997
    Assignee: Epolin, Inc.
    Inventor: Murray S. Cohen
  • Patent number: 5665777
    Abstract: Compounds of formula ##STR1## or a pharmaceutically acceptable salt thereof inhibit matrix metalloproteinases and TNF.alpha. secretion and are useful in the treatment of inflammatory disease states. Also disclosed are matrix metalloproteinases and TNF.alpha. secretion inhibiting compositions and a method for inhibiting matrix metalloproteinases and TNF.alpha. secretion.
    Type: Grant
    Filed: November 14, 1995
    Date of Patent: September 9, 1997
    Assignee: Abbott Laboratories
    Inventors: Stephen W. Fesik, James B. Summers, Jr., Steven K. Davidsen, George S. Sheppard, Douglas H. Steinman, George M. Carrera, Jr., Alan Florjancic, James H. Holms
  • Patent number: 5661183
    Abstract: The present invention relates to novel derivatives of 3-hydroxyanthranilic acid, 3-HANA of general formula (I), wherein R.sup.1 and R.sup.2 are the same or different and selected from H and alkyl; X is selected from alkylthio, arylthio, aryloxy, halogen and cyano; R.sup.3, R.sup.4 are the same or different and selected from halogen, methyl, fluoroalkyl, cyano and Z-R.sup.5 wherein Z is selected from CH.sub.n, NH.sub.m, O, S, SO.sub.2 and CO wherein n=1 or 2; m=0 or 1 and R.sup.5 is selected from alkyl, aryl and fluoroalkyl; or R.sup.3 and R.sup.4 together form a saturated or unsaturated ring system Y-V-Z wherein Y and Z, independently of each other, are as defined for Z above and V is selected from C.sub.1 -C.sub.3 alkylene or alkenylene, --N.dbd., --N.dbd.N-- and (a), wherein R.sub.7 .dbd.
    Type: Grant
    Filed: May 4, 1995
    Date of Patent: August 26, 1997
    Assignees: The University of Maryland, Astra Aktiebolag
    Inventors: Susanna Karin Maria Bjork, Birgitta Kristina Gotthammar, Mats Torbjorn Linderberg, Johan Per Luthman, Kerstin Margareta Irma Persson, Robert Schwarcz
  • Patent number: 5639887
    Abstract: Compounds of the general formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are herein described, A is a straight or branched (C.sub.2 -C.sub.12)alkyl or a phenyl moiety and B is a moiety of the formula: ##STR2## The compounds are effective in potentiating the activity of chemotherapeutic anti-cancer agents by increasing the sensitivity of multi-drug resistant cells to such chemotherapeutic agents.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: June 17, 1997
    Assignee: American Cyanamid Company
    Inventors: Dennis Powell, Rolf Paul, William A. Hallett, Dan M. Berger, Minu D. Dutia
  • Patent number: 5609791
    Abstract: A novel liquid crystal material having a carbon chain containing a conjugated diene as a terminal substituent of the molecule and exhibiting superior characteristics is provided, which is a diene derivative expressed by the formula (I) ##STR1## wherein R and R' each independently represent 1-5C alkyl; A and B each independently represent 1,4-cyclohexylene or 1,4-phenylene; n is 0 or 1; m is an integer of 0 to 2; X and X' each independently represent H atom or F atom when A is 1,4-phenylene or represent H atom when A is 1,4-cyclohexylene; Y is alkyl, halogen or CN, alkoxy, methyl group substituted by 1-3 halogen atoms or trihaloalkoxy when A is 1,4-phenylene, or represent alkyl, alkoxy, methyl group substituted by 1-3 halogen atoms or trihaloalkoxy when A is 1,4-cyclohexylene; and R and R' are not simultaneously alkyl chain of 4 or more carbon atoms.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: March 11, 1997
    Assignee: Chisso Corporation
    Inventors: Atsuko Fujita, Shuichi Matsui, Yuichi Onji, Makoto Ushioda, Yasuyuki Goto
  • Patent number: 5608101
    Abstract: Substituted aryl or heteroaryl in particular benzoyl bicycloalkane-diones and related compounds, intermediates therefor, synthesis thereof, and the use of said diones for the control of weeds.
    Type: Grant
    Filed: May 23, 1995
    Date of Patent: March 4, 1997
    Inventors: Shy-Fuh Lee, Takashi Nishizaka, Kenichi Komatsubara
  • Patent number: 5565191
    Abstract: Stilbene derivatives of formula (I) ##STR1## wherein A, R.sub.1 and R.sub.2 are as defined in the following, are useful for the protection against UV radiation.
    Type: Grant
    Filed: December 13, 1994
    Date of Patent: October 15, 1996
    Assignee: 3V Inc.
    Inventor: Giuseppe Raspanti
  • Patent number: 5536833
    Abstract: A process for preparing compounds of the formula ##STR1## where a, b, c, R.sub.1, R.sub.2, and R.sub.3 are as defined herein including the step of alkylating a phenol of formula ##STR2## with an acetylene of formula ##STR3## where X is chlorine; bromine; --OC(O)--R.sub.5, where R.sub.5 is alkyl, aryl or substituted aryl; or --OCO.sub.2 R.sub.6, where R.sub.6 is alkyl or ##STR4## in the presence of a catalytic amount of a cuprous or cupric salt. The compounds of formula I are intermediates useful in the preparation of pyranyl cyanoguanidine derivatives.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: July 16, 1996
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Jollie D. Godfrey, Jr., Richard H. Mueller, Thomas C. Sedergran, Nachimuthu Soundararajan
  • Patent number: 5527945
    Abstract: Diphenylheteroalkyl derivatives of the formula I ##STR1## where A and R.sup.1 -R.sup.6 have the meanings specified in the description, and the preparation thereof are described.The substances are suitable for controlling diseases and as cosmetic agents.
    Type: Grant
    Filed: August 31, 1994
    Date of Patent: June 18, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Janssen, Hans-Heiner Wuest
  • Patent number: 5521151
    Abstract: We disclose a novel nitrile, i.e. 5,6,7,8-tetrahydro-3,5,5,6,7,8,8-heptamethyl-2-naphthalenecarbonitrile, a perfuming ingredient having a musky, earthy odor, and which is remarkably stable in particularly aggressive media such as for instance antiperspirant bases. This compound may present itself as a racemate or in the form of one of its optically active isomers.Said isomers can be obtained from aldehydes, namely (-)-(6S,7S) and (+)-(6R,7R)-5,6,7,8-tetrahydro-3,5,5,6,7,8,8-heptamethyl-2-naphtalenecarba ldehyde, which aldehydes are not only useful as starting products for the preparation of the corresponding nitriles, but also as perfuming ingredients.
    Type: Grant
    Filed: December 29, 1994
    Date of Patent: May 28, 1996
    Assignee: Firmenich S.A.
    Inventors: Charles Fehr, Francois Delay, Pierre-Alain Blanc, Nathalie Chaptal-Gradoz
  • Patent number: 5519162
    Abstract: A method for removing hydrogen cyanide from a hydrogen cyanide-contaminated organic liquid includes the steps of contacting the hydrogen cyanide-contaminated organic liquid with a metal alkoxide to generate a metal cyanide salt and an alkanol and then separating the organic liquid from the metal cyanide salt and the alkanol.
    Type: Grant
    Filed: August 23, 1994
    Date of Patent: May 21, 1996
    Assignee: Rohm and Haas Company
    Inventors: Sudhir K. Agarwal, Rajiv M. Banavali, Bharati D. Chheda, Samuel F. Reed, Jr.
  • Patent number: 5514683
    Abstract: The compounds of the formula I ##STR1## and their pharmaceutical acceptable salts, which are defined herein, are ligands for cholecystokinin and/or gastrin receptors.
    Type: Grant
    Filed: August 9, 1994
    Date of Patent: May 7, 1996
    Assignee: James Black Foundation Limited
    Inventors: Sarkis B. Kalindjian, Caroline M. R. Low, Iain M. McDonald, Robert A. D. Hull, Nigel P. Shankley, Ildiko M. Buck, Katherine I. M. Steel, Jonathan M. R. Davies, David J. Dunstone, Elaine A. Harper, Michael J. Pether, Michael J. Bodkin, Matthew J. Tozer, Martin L. Hudson
  • Patent number: 5478835
    Abstract: Disclosed is a tricyclic compound represented by the formula (I): ##STR1## wherein each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently represents hydrogen, C1-6 alkyl, C1-6 alkoxy, C1-6 alkylthio, amino, C1-6 alkylamino, halogenated C1-6 alkyl, halogenated C1-6 alkoxy, halogen, nitro, cyano, carboxy, C1-6 alkoxycarbonyl, hydroxymethyl, CR.sup.9 R.sup.10 CO.sub.2 R.sup.11 (wherein each of R.sup.9, R.sup.10 and R.sup.11 independently represents hydrogen or C1-6 alkyl) or CONR.sup.12 R.sup.13 (wherein each of R.sup.12 and R.sup.13 independently represents hydrogen or C1-6-alkyl); R.sup.5 represents hydrogen or C1-6 alkyl; each of R.sup.6, R.sup.7 and R.sup.8 independently represents hydrogen, C1-6 alkyl, hydroxy, C1-6 alkoxy, C1-6 alkanoyloxy, C1-6 alkylthio, thiocyanato or halogen; X represents CH or N; Y.sup.1 -Y.sup.2 represents CH.sub.2 -O, CH.sub.2 -S(O).sub.n, (wherein n represents 0, 1, or 2), CH.sub.2 CH.sub.2, CH.dbd.CH or CON(R.sup.14) (wherein R.sup.
    Type: Grant
    Filed: May 2, 1994
    Date of Patent: December 26, 1995
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Toshiaki Kumazawa, Masashi Yanase, Hiroyuki Harakawa, Hiroyuki Obase, Shoji Oda, Shiro Shirakura, Koji Yamada, Kazuhiro Kubo
  • Patent number: 5470994
    Abstract: Sulfonium and oxysulfonium salts, useful as photoinitiators, have directly attached to the sulfur atom thereof:at least one aromatic or heterocyclic aromatic substituent containing at least 14 aromatic atoms and having a removable positive hydrogen ion, said substituent exhibiting a higher energy occupied molecular orbital than at least one other substituent directly attached to said sulfur atom;and at least one substituent comprising an electron withdrawing group and exhibiting a lower energy unoccupied molecular orbital than at least one other substituent directly attached to said sulfur atom;said salt being capable, upon exposure to visible radiation, of undergoing irreversible intramolecular rearrangement to form a Bronsted acid comprising the anion of said salt and said removable positive hydrogen ion.
    Type: Grant
    Filed: April 5, 1990
    Date of Patent: November 28, 1995
    Assignee: Eastman Kodak Company
    Inventors: Franklin D. Saeva, David T. Breslin
  • Patent number: 5468421
    Abstract: A liquid crystalline compound which has a low viscosity and is electrically and chemically stable and compatible with other known liquid crystalline compounds at low temperatures, and a liquid crystal composition containing the same, which compound is a phenyl-4-cyclohexylbutylcyclohexane derivative expressed by the formula: ##STR1## wherein R represents a hydrogen atom or a linear or branched alkyl group of 1 to 15 carbon atoms, and X.sub.1, X.sub.2 and X.sub.3 are each independent and X.sub.1 and X.sub.3 each represent a hydrogen atom or a halogen atom and X.sub.2 represents a hydrogen atom or a linear or branched alkyl group of 1 to 15 carbon atoms (wherein one --CH.sub.2 CH.sub.2 -- bond may be replaced by a --CH.dbd.CH-- bond and one non-adjacent --CH.sub.2 -- bond may be replaced by an oxygen atom), a halogen atom, a cyano group, a trifluoromethyl group or a trifluoromethoxy group.
    Type: Grant
    Filed: April 28, 1993
    Date of Patent: November 21, 1995
    Assignee: Chisso Corporation
    Inventors: Shuichi Matsui, Yasuyuki Goto, Yuichi Onji, Atsuko Fujita
  • Patent number: 5463059
    Abstract: A process for preparing compounds of the formula ##STR1## where a, b, c, R.sub.1, R.sub.2, and R.sub.3 are as defined herein including the step of alkylating a phenol of formula ##STR2## with an acetylene of formula ##STR3## where X is chlorine; bromine; --OC(O)--R.sub.5, where R.sub.5 is alkyl, aryl or substituted aryl; or --OCO.sub.2 R.sub.6, where R.sub.6 is alkyl or ##STR4## in the presence of a catalytic amount of a cuprous or cupric salt. The compounds of formula I are intermediates useful in the preparation of pyranyl cyanoguanidine derivatives.
    Type: Grant
    Filed: October 1, 1993
    Date of Patent: October 31, 1995
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Jollie D. Godfrey, Jr., Richard H. Mueller, Thomas C. Sedergran, Nachimuthu Soundararajan
  • Patent number: 5449810
    Abstract: A novel liquid crystal material having a carbon chain containing a conjugated diene as a terminal substituent of the molecule and exhibiting superior characteristics is provided, which is a diene derivative expressed by the formula (I) ##STR1## wherein R and R' each independently represent 1-5C alkyl; A and B each independently represent 1,4-cyclohexylene or 1,4-phenylene; n is 0 or 1; m is an integer of 0 to 2; X and X' each independently represent H atom or F atom when A is 1,4-phenylene or represent H atom when A is 1,4-cyclohexylene; Y is alkyl, halogen or CN, alkoxy, methyl group substituted by 1-3 halogen atoms or trihaloalkoxy when A is 1,4-phenylene, or represent alkyl, alkoxy, methyl group substituted by 1-3 halogen atoms or trihaloalkoxy when A is 1,4-cyclohexylene; and R and R' are not simultaneously alkyl chain of 4 or more carbon atoms.
    Type: Grant
    Filed: April 1, 1993
    Date of Patent: September 12, 1995
    Assignee: Chisso Corporation
    Inventors: Atsuko Fujita, Shuichi Matsui, Yuichi Onji, Makoto Ushioda, Yasuyuki Goto
  • Patent number: 5417882
    Abstract: Liquid-crystalline compounds of the formulae I and II,Z.sup.1 --(X.sup.1 --R.sup.1 --Y--M).sub.m IZ.sup.2 --(X.sup.2 --R.sup.1 --Y--M).sub.n IIwhereZ.sup.1 is the radical of an m-valent alcohol an m-valent acid or certain trivalent triazine derivatives; Z.sup.2 is an n-valent radical of a monocyclic or polycyclic aromatic compound; X.sup.1 is a chemical bond or --CO--; X.sup.2 is --O--, --S--, --CO--O--, --O--CO--, --SO.sub.2 --, --SO.sub.2 --O--, --O--SO.sub.2 --O--, --NR.sup.4 --, --CO--NR.sup.4 --NR.sup.4 --O-- or --CO--N<, where R.sup.4 is H or C.sub.1 -C.sub.8 -alkyl; m and n are 3 to 6; R.sup.1 is a C.sub.2 -C.sub.20 -bridge having 2 to 12 bridging members, which may be interrupted by --O--, --S-- or --NR.sup.4 --, each of these hetero units being separated by at least 2 carbon atoms; Y is a chemical bond, --O--, --S--, --CO--O--, --O--CO--, --NR.sup.4 --, --CO--NR.sup.4 -- or --NR.sup. 4 --CO--; M is a mesogenic group.
    Type: Grant
    Filed: March 11, 1992
    Date of Patent: May 23, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Volker Bach, Karl-Heinz Etzbach, Karl Siemensmeyer, Gerhard Wagenblast
  • Patent number: 5414125
    Abstract: A diamino-alpha-alkylstilbene useful as an epoxy resin curing agent is represented by the following Formula I: ##STR1## wherein R is independently hydrogen, a C.sub.1 -C.sub.10 hydrocarbyl(oxy) group or a halogen, nitro, nitrile, phenyl or --CO--R.sup.1 group wherein R.sup.1 is independently hydrogen or a C.sub.1 -C.sub.3 hydrocarbyl group; each R.sup.4 is independently hydrogen or a C.sub.1 -C.sub.10 hydrocarbyl group; and Y is a ##STR2## group wherein n=0 or 1.
    Type: Grant
    Filed: July 23, 1993
    Date of Patent: May 9, 1995
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5401434
    Abstract: A novel liquid crystal compound having an intermediate group of a cis-1,4-substituted 2-butenyl group, low viscosity and a broad mesomorphic temperature range is provided, which compound is expressed by the following formula: ##STR1## wherein R.sup.1 represents an alkyl group of 1 to 10 carbon atoms, n represents 1 or 2, X represents a hydrogen atom, an alkyl group, a halogen atom, a cyano group, an alkoxy group, a methyl group substituted by 1 to 3 halogen atom(s) or a trihaloalkoxy group, and Y and Y' each independently represents a hydrogen atom, or a halogen atom.
    Type: Grant
    Filed: April 1, 1993
    Date of Patent: March 28, 1995
    Assignee: Chisso Corporation
    Inventors: Atsuko Fujita, Shuichi Matsui, Yuichi Onji, Makoto Ushioda, Yasuyuki Goto
  • Patent number: 5387747
    Abstract: The present invention relates to the derivatives of the formula ##STR1## and their tautomeric forms, as well as their addition salts, and to their use in therapeutics, especially for the treatment and prevention of cardiovascular diseases and in particular for the treatment of hypertension, cardiac insufficiency and diseases of the arterial wall, especially atherosclerosis.
    Type: Grant
    Filed: April 16, 1993
    Date of Patent: February 7, 1995
    Assignee: Laboratoires Upsa
    Inventors: Nicole Bru-Magniez, Timur Gungor, Jean-Marie Teulon
  • Patent number: 5380910
    Abstract: A method for producing an asymmetric biaryl derivative which comprises dehalogenocoupling halogenated benzene derivatives, wherein a bromobenzene derivative of the formula: ##STR1## wherein R is a lower alkyl group or a lower alkoxy group, which is attached at the 3- or 4-position, and a 2-chlorobenzene derivative of the formula: ##STR2## wherein R' is a cyano group or an alkoxycarbonyl group, are reacted in pyridine in the presence of triphenylphosphine, an anhydrous nickel compound and a reducing metal to obtain an asymmetric biaryl derivative of the formula: ##STR3## wherein R and R' are as defined above, and R is attached at the 3- or 4-position.
    Type: Grant
    Filed: March 29, 1993
    Date of Patent: January 10, 1995
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventor: Hiroyuki Kageyama
  • Patent number: 5373023
    Abstract: The invention provides compounds which are tetrahydronaphthalene derivatives of the formula (I) ##STR1## wherein R.sub.1 represents a halogen atom, a cyano group, a nitro group, an unbranched (C.sub.1 -C.sub.6) alkoxy group, a (C.sub.1 -C.sub.6 cycloalkyl) (C.sub.1 -C.sub.2 alkoxy) group or an aryl (C.sub.1 -C.sub.2 alkoxy) group,R.sub.2 represents a (C.sub.1 -C.sub.4) alkyl group, an aryl group optionally substituted with at least one methoxy group, a pyridyl group or a benzodioxanyl group,R.sub.3 represents a hydrogen atom or a (C.sub.1 -C.sub.2) alkyl group, and n=0 to 3, or are addition salts with pharmaceutically acceptable acids. The compounds of the invention have anti-ischaemic activity.
    Type: Grant
    Filed: August 4, 1993
    Date of Patent: December 13, 1994
    Assignee: SYNTHELABO
    Inventors: Paul Howard Williams, Christian Hoornaert, Jean Claude Muller
  • Patent number: 5370822
    Abstract: A novel liquid crystal compound exhibiting a low driving voltage, a liquid crystal phase within a broad temperature range and a good compatibility with other known liquid crystal compounds at low temperatures is provided, which compound is expressed by the formula ##STR1## wherein R is H or a linear or branched alkyl group of 1-10C, X is H or F, and the vinyl group has a transconfiguration. This compound has a high dielectric anisotropy value for its relatively low viscosity and can drive liquid crystal display elements under a low voltage, and further exhibits a liquid crystal phase within a broad temperature range of about room temperature to about 200.degree. C., and exhibits a good compatibility with many other liquid crystalline compounds such as ester compounds, Schiff's base compounds, biphenyls, phenylcyclohexanes, heterocyclic compounds, fluorine compounds, etc., particularly a good compatibility at low temperatures, and hence can provide improved liquid crystal materials.
    Type: Grant
    Filed: September 10, 1993
    Date of Patent: December 6, 1994
    Assignee: Chisso Corporation
    Inventors: Shuichi Matsui, Yuichi Onji, Atsuko Fujita, Tomoyuki Kondo, Yasuyuki Goto
  • Patent number: 5356558
    Abstract: A tolane derivative, a liquid crystal composition containing the derivative, and a liquid crystal display device including the composition, in which the tolane derivative is represented by the following general formula: ##STR1## wherein R represents a straight-chain alkyl group having 1 to 10 carbon atoms, and each of X.sub.1, X.sub.2, X.sub.3 and X.sub.4 represents a fluorine atom or a hydrogen atom wherein at least one X represents a fluorine atom, and Y represents a nitrile group or a straight-chain alkyl group having 1 to 10 carbon atoms.By blending the above-described compound with a general liquid crystal composition, a liquid crystal composition is provided which exhibits a wide practical temperature range as well as a large anisotropy of refractive index.
    Type: Grant
    Filed: July 21, 1993
    Date of Patent: October 18, 1994
    Assignee: Seiko Epson Corporation
    Inventors: Shuhei Yamada, Shuji Ikukawa, Jun Ito, Jitsuko Nakayama
  • Patent number: 5329054
    Abstract: Activated carboxylic acids and esters such as pentafluorobenzoic acid are rapidly decarboxylated in high yields by reacting the acid or ester with an alkanolamine reagent which catalyzes the reaction.
    Type: Grant
    Filed: July 19, 1993
    Date of Patent: July 12, 1994
    Assignee: Albemarle Corporation
    Inventors: Kevin J. Theriot, Niomi L. Krzystowczyk, Yueh-Dong Chen, Edward A. Burt, Lawrence H. Shepherd, Jr.
  • Patent number: 5321046
    Abstract: Disclosed herein are novel unsymmetrical dithiol ketals which are useful in the treatment or prevention of hypercholesterolemia, hyperlipoproteinemia, and atherosclerosis.
    Type: Grant
    Filed: October 27, 1992
    Date of Patent: June 14, 1994
    Assignee: Bristol-Myers Squibb Company
    Inventors: Sing-Yuen Sit, John J. Wright, Jeff A. Field
  • Patent number: 5288895
    Abstract: The subject of the invention is a process for the preparation of 4-methyl-2'-cyanobiphenyl of formula: ##STR1## wherein a benzonitrile halide of general formula: ##STR2## in which Hal represents a halogen atom, is reacted, in the presence of a manganese salt, with an organometallic derivative of general formula: ##STR3## in which X represents a halogen atom, and the complex obtained is then hydrolysed, which provides the desired compound.
    Type: Grant
    Filed: April 6, 1993
    Date of Patent: February 22, 1994
    Assignee: Elf Sanofi
    Inventors: Michel Bouisset, Alain Boudin
  • Patent number: 5288901
    Abstract: There are provided important pyrroline and glycine intermediates, methods for the preparation of said intermediates and the use thereof in the manufacture of arylpyrrole insecticidal agents.
    Type: Grant
    Filed: April 8, 1992
    Date of Patent: February 22, 1994
    Assignee: American Cyanamid Company
    Inventors: Robert F. Doehner, Jr., Jerry M. Barton, David G. Kuhn
  • Patent number: 5283352
    Abstract: Catechol compounds of formula I ##STR1## where R.sub.1, R.sub.2, R.sub.3 and X are as described herein are effective Catechol-O-methyltransferase inhibitors.
    Type: Grant
    Filed: December 7, 1992
    Date of Patent: February 1, 1994
    Assignee: Orion-yhtyma Oy
    Inventors: Reijo J. Backstrom, Kalevi E. Heinola, Erkki J. Honkanen, Seppo K. Kaakkola, Pekka J. Kairisalo, Inge-Britt Y. Linden, Pekka I. Mannisto, Erkki A. O. Nissinen, Pentti Pohto, Aino K. Pippuri, Jarmo J. Pystynen
  • Patent number: 5279764
    Abstract: The invention relates to dihalogenobenzene derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --(Z.sup.2 --A.sup.3).sub.n --R.sup.2wherein R.sup.1, R.sup.2, A.sup.1, A.sup.2, A.sup.3, Z.sup.1, Z.sup.2 and n are as defined in the specification.
    Type: Grant
    Filed: November 23, 1992
    Date of Patent: January 18, 1994
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Volker Reiffenrath, Joachim Krause, Georg Weber, Ulrich Finkenzeller, Andreas Wachtler, Thomas Geelhaar, David Coates, Ian C. Sage, Simon Greenfield
  • Patent number: 5264502
    Abstract: An epoxy resin composition useful as a molded article is cured with a combination of curing agents including diamino-alpha-alkylstilbenes and other curing agents wherein the epoxy resin and/or the other curing agent can contain rodlike mesogenic moieties.
    Type: Grant
    Filed: April 10, 1991
    Date of Patent: November 23, 1993
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5260285
    Abstract: Novel substituted imidazopyridazines of formula (I) which are useful as angiotensin II antagonists, are disclosed.
    Type: Grant
    Filed: November 25, 1991
    Date of Patent: November 9, 1993
    Assignee: Merck & Co., Inc.
    Inventors: Eric E. Allen, William J. Greenlee, Prasun K. Chakravarty, Malcolm MacCoss, Arthur A. Patchett, Thomas F. Walsh
  • Patent number: 5256694
    Abstract: Novel diarylacetylenes of the formula I ##STR1## where A, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 have the meanings stated in the description, are useful for the treatment of disorders.
    Type: Grant
    Filed: May 22, 1992
    Date of Patent: October 26, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Heiner Wuest, Fritz-Frieder Frickel, Axel Nuerrenbach
  • Patent number: 5238603
    Abstract: A liquid crystal compound having specific features suitable to use for a display mode utilizing ferroelectric liquid crystals, particularly a large spontaneous polarization value and a liquid crystal composition using the compound are provided, which compound is an optically active liquid crystalline compound of the formula ##STR1## wherein l and m each are 0 or 1; at least one of R.sup.1 and R.sup.2 is an optically active alkoxy group of the formula ##STR2## wherein R.sup.3 is 2 or 3C alkyl and R.sup.4 is 3-18C alkyl, but R.sup.3 .noteq.R.sup.4 and the other thereof is 1-20C alkyl, alkoxy or alkanoyloxy, halogen or cyano; and A is a specified two or three rings compound.
    Type: Grant
    Filed: April 7, 1992
    Date of Patent: August 24, 1993
    Assignee: Chisso Corporation
    Inventors: Kazutoshi Miyazawa, Naoyuki Yoshida, Masakazu Kaneoya
  • Patent number: 5233054
    Abstract: Halophthalic anhydrides are prepared by the liquid phase reaction of a brominating agent with halogen substituted hexa- or tetra-hydrophthalic anhydrides.
    Type: Grant
    Filed: June 26, 1991
    Date of Patent: August 3, 1993
    Assignee: Occidental Chemical Corporation
    Inventors: David Y. Tang, Mary K. Cocoman, Harry E. Buckholtz
  • Patent number: 5223387
    Abstract: A color light-sensitive material comprising a support provided thereon at least one light-sensitive silver salt layer combined with an image forming compound represented by formula (I) ##STR1## wherein Dye represents a cyan dye group or a precursor thereof represented by formula (II) defined in the specification;X represents a chemical bond or a linking group;Y represents a group which releases Dye corresponding to or countercorresponding to light-sensitive silver salt having an imagewise latent image and makes a difference in diffusibility between the dye thus released and the compound represented by formula (I), provided that Dye and X are linked to each other by A or E in formula (II); andq represents an integer of 1 or 2, provided that when q is 2, the two groups (Dye--X) may be the same or different.
    Type: Grant
    Filed: September 8, 1992
    Date of Patent: June 29, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Masaaki Tsukase, Kozo Sato, Hiroyuki Hirai
  • Patent number: 5220048
    Abstract: Benzocyclobutene-1,2-dichlorides, -bromides and -iodides which are substituted in the benzene ring are accessible in good yields and short reaction times by reacting substituted 1,2-(dichloromethyl or dibromomethyl)-benzenes with NaI in acetonitrile as the solvent. They can be used together with dienophils, for example 1,4-quinones, in Diels-Alder reactions.
    Type: Grant
    Filed: May 24, 1989
    Date of Patent: June 15, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Marcus Baumann, Walter Fischer, Vratislav Kvita, Carl W. Mayer
  • Patent number: 5214187
    Abstract: Novel benzonitriles, benzaldehydes and benzyl alcohols of the formula I ##STR1## where R.sup.1 is methyl or ethyl, R.sup.2 is alkyl, alkenyl, cycloalkyl, cycloalkenyl, bicycloalkyl, bicycloalkenyl, or C.sub.1 -C.sub.5 -alkyl-substituted cycloalkyl, cycloalkenyl, bicycloalkyl or bicycloalkenyl, X is hydrogen, chlorine or fluorine and Z is --CN, CHO or ##STR2## where R.sup.3 is hydrogen, cyano, C.sub.2 -C.sub.4 -alkynyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.1 -C.sub.4 -alkyl, with the proviso that R.sup.2 is not --CH.sub.2 --CH.dbd.CH--B when B is hydrogen, alkyl or alkenyl and at the same time R.sup.1 is methyl and Z is ##STR3## and with the proviso that R.sup.2 is not methyl or ethyl when R.sup.1 is methyl and at the same time Z is ##STR4## and furthermore with the proviso that R.sup.2 is not methyl when R.sup.1 is methyl or ethyl and at the same time Z is --CN or --CHO.
    Type: Grant
    Filed: September 18, 1992
    Date of Patent: May 25, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Wolf, Hans Theobald, Norbert Goetz
  • Patent number: 5182296
    Abstract: A naphthyloxazolidone derivative of the formula: ##STR1## wherein R.sup.1 is hydrogen atom, hydroxy group, nitro group, amino group, sulfo group, aminosulfoyul group, a lower alkenyloxy group, a lower alkynyloxy group, a mono or di(lower alkyl)aminocarbonyloxy group, a lower alkanoyloxy group or a lower alkoxy group which may have a substituent selected from an aryl group, a cycloalkyl group, an oxygen-containing heteromonocyclic group, hydroxy group, a lower alkoxy group, cyano group, a di(lower alkyl)amino group, aminocarbonyl group, a lower alkoxycarbonyl group, a lower alkanoyloxy group, a lower alkylthio group, a lower alkylsulfinyl group and a lower alkylsulfonyl group; R.sup.2 is hydroxy group, a lower alkoxy group, a lower alkylsulfonyloxy group, triazo group or an amino group which may have a substituent selected from a lower alkyl group and a lower alkanoyl group, and a pharmaceuticaly acceptable salt thereof are disclosed.
    Type: Grant
    Filed: October 18, 1990
    Date of Patent: January 26, 1993
    Assignee: Tanabe Seiyaky Co., Ltd.
    Inventors: Hideo Nakai, Koichiro Yamada, Shumihiro Nomura, Mamoru Matsumoto, Hiroshi Iwata
  • Patent number: 5164502
    Abstract: Chloro and bromophenols and N-acylanilines are fluorinated in an ortho or para position with an N-fluoropyridinium salt to obtain fluorohalophenols and N-acylfluorohaloanilines, which can be further converted to fluorophenols and N-acylfluoroanilines by reduction. Thus, o-fluorophenol is obtained by fluorination of p-bromophenol with 2-chloro-6-(trichloromethyl)pyridinium fluoroborate and reduction of the product obtained with sodium formate and a palladium catalyst. N-Fluoropyridinium salts having trichloromethyl substituents are disclosed.
    Type: Grant
    Filed: November 8, 1991
    Date of Patent: November 17, 1992
    Assignee: DowElanco
    Inventors: Alexander P. Fung, M. Moklesur Rahman, Thomas J. Dietsche
  • Patent number: 5152826
    Abstract: An herbicide compound of the formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, nitro; cyano; C.sub.1 -C.sub.2 haloalkyl, or R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are alkylene having 2 to 5 carbon atoms;R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.3 and R.sup.4 together are oxo;R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.5 and R.sup.6 together are alkylene having 2 to 5 carbon atoms;R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n --wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.
    Type: Grant
    Filed: October 16, 1991
    Date of Patent: October 6, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventor: Christopher G. Knudsen
  • Patent number: 5147892
    Abstract: Benzyl ketones of the formula ##STR1## where X is CH or N,Y is O or NR.sup.4,R.sup.1, R.sup.2 are H or alkyl,R.sup.3 is halogen, cyano, nitro, alkyl, cycloalkyl, alkoxy, haloalkyl, arylalkyl, arylalkoxy, aryloxy or aryl, and the aryl groups in turn may be substituted,R.sup.4 is OH, alkoxy or arylalkoxy andR.sup.5 is H, methyl, halogen or methoxy,and fungicides containing these compounds.
    Type: Grant
    Filed: June 27, 1991
    Date of Patent: September 15, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Horst Wingert, Hubert Sauter, Franz Roehl, Reinhard Doetzer, Gisela Lorenz, Eberhard Ammermann
  • Patent number: 5132423
    Abstract: Reactions between a solid polar and a non-polar compound, especially nucleophilic aromatic substitution reactions between an alkali metal salt of a hydroxyaromatic compound or thio analog thereof and an activated halo- or nitro-substituted aromatic compound, are conducted in a non-polar organic solvent such as toluene or xylene, in the presence of a hexaalkylguanidinium or .alpha.,.omega.-bis(pentaalkylguanidinium)alkane salt, or a corresponding heterocyclic salt, as a phase transfer catalyst. The method is particularly useful for the preparation of bisimides from bisphenol A or 4,4'-biphenol salts and 4-nitro- or 4-halophthalimides.
    Type: Grant
    Filed: March 13, 1991
    Date of Patent: July 21, 1992
    Assignee: General Electric Company
    Inventors: Daniel J. Brunelle, Deborah A. Haitko, James P. Barren, Sunita Singh
  • Patent number: 5126371
    Abstract: Novel diarylacetylenes of the formula I ##STR1## where A, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 have the meanings stated in the description, are useful for the treatment of disorders.
    Type: Grant
    Filed: August 20, 1990
    Date of Patent: June 30, 1992
    Assignee: BASF Akteingesellschaft
    Inventors: Hans-Heiner Wuest, Fritz-Frieder Frickel, Axel Nuerrenbach
  • Patent number: 5116982
    Abstract: Chloro and bromophenols and N-acylanilines are fluorinated in an ortho or para position with an N-fluoropyridinium salt to obtain fluorohalophenols and N-acylfluorohaloanilines, which can be further converted to fluorophenols and N-acylfluoroanilines by reduction. Thus, o-fluorophenol is obtained by fluorination of p-bromophenol with 2-chloro-6-(trichloromethyl)-pyridinium fluoroborate and reduction of the product obtained with sodium formate and a palladium catalyst. N-fluoropyridinium salts having trichloromethyl substituents are disclosed.
    Type: Grant
    Filed: August 6, 1990
    Date of Patent: May 26, 1992
    Assignee: DowElanco
    Inventors: Alexander P. Fung, M. Moklesur Rahman, Thomas J. Dietsche
  • Patent number: 5112382
    Abstract: Compounds of the formula ##STR1## wherein A is selected from the group consisting of (1) phenyl, (2) naphthyl, (3) phenyl substituted with one or more halo, cyano, (C.sub.1 -C.sub.4) alkyl, nitro, (C.sub.1 -C.sub.4)haloalkyl, and (C.sub.1 -C.sub.4)thioalkyl, (4) naphthyl substituted with one or more halo, cyano, (C.sub.1 -C.sub.4)alkyl,nitro,(C.sub.1 -C.sub.4), and (C.sub.1 -C.sub.4) thioalkyl, (5) thiophene, (6) furan, (7) thiophene substituted with one or more substituents selected from halo and nitro, and (8) furan substituted with one or more substituents selected from halo and nitro;R disclose as microbicidally and fungicidally active.
    Type: Grant
    Filed: May 24, 1990
    Date of Patent: May 12, 1992
    Assignee: Rohm and Haas Company
    Inventor: Adam C. Hsu