Benzene Ring Containing Patents (Class 570/182)
  • Patent number: 5334789
    Abstract: Disclosed are an oxychlorination catalyst comprising a carrier material, and a palladium compound, a copper compound and a vanadium compound which are supported on the carrier material; an oxychlorination catalyst comprising a carrier material, and a palladium compound, a copper compound, a vanadium compound and an alkaline earth metal compound which are supported on the carrier material; processes for preparing these catalysts; and a method for oxychlorination of an olefin or an aromatic hydrocarbon using one of these catalysts.
    Type: Grant
    Filed: June 30, 1993
    Date of Patent: August 2, 1994
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masashi Komatsu, Michio Yamamoto, Masaru Ishino, Gohfu Suzukamo
  • Patent number: 5334370
    Abstract: Disclosed are x-ray contrast compositions for oral or retrograde examination of the gastrointestinal tract comprising a polymeric material capable of forming a coating on the gastrointestinal tract and an x-ray producing agent of the formula ##STR1## and methods for their use in diagnostic radiology of the gastrointestinal tract whereinR=C.sub.1 -C.sub.25 alkyl, cycloalkyl, unsaturated allyl or halo-lower-alkyl, optionally substituted with halo, fluoro-lower-alkyl, aryl, lower-alkoxy, hydroxy, carboxy, lower-alkoxy carbonyl or lower-alkoxy-carbonyloxy, (CR.sub.1 R.sub.2).sub.p --(CR.sub.3 .dbd.CR.sub.4).sub.m Q, or (CR.sub.1 R.sub.2).sub.p --C.tbd.C--Q;R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently H, lower-alkyl, optionally substituted with halo;n is 1-5;m is 1-5;p is 1-10; andQ is H, lower-alkyl, lower-alkenyl, lower-alkynyl, lower-alkylene, aryl, or aryl-lower alkyl.
    Type: Grant
    Filed: February 4, 1993
    Date of Patent: August 2, 1994
    Assignee: Sterling Winthrop Inc.
    Inventors: Kurt A. Josef, Edward R. Bacon, Kimberly G. Estep, Carl R. Illig, Brent D. Douty
  • Patent number: 5328644
    Abstract: Disclosed is a nematic liquid crystal mixture having a positive dielectric anisotropy .DELTA..epsilon. of at least +4 and a birefringence .DELTA.n of at least 0.18, said mixture comprising at least one fluorinated chloroterphenyl compound of formula IR--E--Cl IwhereinR is an alkyl or alkenyl radical having up to 15 C atoms, said radical being unsubstituted or substituted by halogen, one or more CH.sub.2 groups in the radical optionally being replaced, in each case independently of one another, by --O--, ##STR1## in such a manner that oxygen atoms are not linked directly to one another, andis ##STR2## or the mirror image thereof, and wherein the benzene rings can be optionally further substituted by fluorine.
    Type: Grant
    Filed: November 12, 1992
    Date of Patent: July 12, 1994
    Assignee: Merck Patent Gesellschaft
    Inventors: Mark Goulding, Simon Greenfield, David Coates, Robert Clemitson
  • Patent number: 5308607
    Abstract: Disclosed are contrast agents of the formula ##STR1## contained in aqueous compositions and methods for their use in diagnostic radiology of the gastrointestinal tract whereinR=C.sub.1 -C.sub.25 alkyl, cycloalkyl, unsaturated allyl or halo-lower-alkyl, optionally substituted with halo, fluoro-lower-alkyl, aryl, lower-alkoxy, hydroxy, carboxy, lower-alkoxy carbonyl or lower-alkoxy-carbonyloxy, (CR.sub.1 R.sub.2).sub.p --(CR.sub.3 .dbd.CR.sub.4).sub.m Q, or (CR.sub.1 R.sub.2).sub.p --C.tbd.C--Q;R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently H, lower-alkyl, optionally substituted with halo;n is 1-5;m is 1-5;p is 1-10; andQ is H, lower-alkyl, lower-alkenyl, lower-alkynyl, lower-alkylene, aryl, or aryl-lower alkyl.
    Type: Grant
    Filed: February 4, 1993
    Date of Patent: May 3, 1994
    Assignee: Sterling Winthrop Inc.
    Inventors: Kurt A. Josef, Edward R. Bacon, Kimberly G. Estep, Carl R. Illig, Brent D. Douty
  • Patent number: 5292452
    Abstract: Compounds of the formula ##STR1## wherein Z.sup.1 denotes a single covalent bond or --CH.sub.2 Ch.sub.2 --; ring A.sup.1 represents 1,4-phenylene, pyrimidine-2,5-diyl, pyridine-2,5-diyl or, when Z.sup.1 stands for --CH.sub.2 CH.sub.2 --, also trans-1,4-cyclohexylene; X.sup.1 stands for fluorine or chlorine; X.sup.2 signifies fluorine, chlorine or hydrogen, with the proviso that X.sup.2 only signifies hydrogen when X.sup.1 is chlorine or when ring A.sup.1 signifies pyridine-2,5-diyl and Z.sup.1 signifies --CH.sub.2 CH.sub.2 --; and R.sup.1 signifies 1E-alkenyl with 2 to 12 carbon atoms,their manufacture, liquid crystalline mixtures which contain these compounds and their use for electro-optical purposes.
    Type: Grant
    Filed: August 19, 1991
    Date of Patent: March 8, 1994
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Richard Buchecker, Alfred Germann, Martin Schadt, Alois Villiger
  • Patent number: 5264511
    Abstract: Monomers, B-stage polymers, C-stage polymers, cured polymers and electricy conducting polymers of acetylene-terminated aromatic monomers containing three benzene rings separated by ethylene groups are disclosed. These new polymers can withstand aggressive environments and are particularly adapted for use in high temperature composites in addition to the utilization of their electrical conducting properties. Preparation of these materials is accomplished by melt polymerization and heat treatment at high temperatures.
    Type: Grant
    Filed: June 30, 1992
    Date of Patent: November 23, 1993
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: Theordore R. Walton
  • Patent number: 5254776
    Abstract: Bromobiphenyls (such as 2-fluoro-4-bromobiphenyl) are synthesized by reacting together a phenylboronic acid (such as phenylboronic acid) and a bromoiodobenzene (such as 2-fluoro-4-bromoiodobenzene). The reaction generally takes place with the aid of a catalyst (such as palladium in a zero valance state) and an inert solvent (such as fluorobenzene). Control of temperature is very important to obtain both an acceptable reaction rate and an acceptable level of terphenyl byproduct.
    Type: Grant
    Filed: July 17, 1992
    Date of Patent: October 19, 1993
    Assignee: Mallinckrodt Specialty Chemicals Company
    Inventors: John F. Lang, Narayanasamy Gurusamy
  • Patent number: 5247124
    Abstract: A process for preparing a substituted styrene by reacting a bisarylalkyl ether in the presence of an acid catalyst is disclosed. The process is preferably used for the preparation of 4-acetoxystyrene from 4,4'-(oxydiethylidene)bisphenol diacetate and 4-methoxystyrene from 4,4'-(oxydiethylidene)bisphenol dimethyl ether. A process for preparing a bisarylalkyl ether by reacting a corresponding arylalkanol in the presence of an acid catalyst is also disclosed.
    Type: Grant
    Filed: August 25, 1992
    Date of Patent: September 21, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: Mohammad Aslam, Brad L. Smith, George Kvakovszky
  • Patent number: 5200169
    Abstract: Vinyl radiohalogenated small molecules as shown in formulas I and II: ##STR1## wherein *X is radiohalogen, C.dbd.C is a double bonded set of sp.sup.2 hybridized carbon atoms, and substituents R.sub.1, and R.sub.2 are as defined in the specification. Y is a substituent containing any of the groups described for R.sub.1 and R.sub.2, except that Y cannot be hydrogen, and bearing a functional group suitable for binding to protein under conditions that preserve the biological activity of the protein. The compounds of formulas I and II can be coupled to proteins such as monoclonal antibodies to provide reagents for diagnostic and therapeutic applications. Also metalated precursors of compounds I and II, as well as radiopharmaceutical reagent kits containing any of the subject small molecules.
    Type: Grant
    Filed: July 5, 1989
    Date of Patent: April 6, 1993
    Assignee: NeoRx Corporation
    Inventors: Daniel S. Wilbur, Stephen W. Hadley
  • Patent number: 5194178
    Abstract: Chloro tolanes of the formula I ##STR1## wherein R.sup.1 denotes alkyl with up to 12 carbon atoms wherein one or two non-adjacent CH.sub.2 groups may also be replaced by --O--, --O--CO--, --CO--O-- and/or --CH.dbd.CH--,A is trans-1,4-cyclohexylene or 1,4-phenylene,r is 0 or 1,s is 0 or 1,L.sup.1 and L.sup.2 are H or F,whereby one of the substituents L.sup.1 and L.sup.2 is F and the other is H or F and if s is 0 and R.sup.1 is alkyl having 2 to 12 carbon atoms both L.sup.1 and L.sup.2 may be Hare suitable as components of liquid crystalline media.
    Type: Grant
    Filed: January 28, 1991
    Date of Patent: March 16, 1993
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: David Coates, Simon Greenfield, Mark Goulding
  • Patent number: 5194672
    Abstract: A process for preparing a substituted styrene by reacting a bisarylalkyl ether in the presence of an acid catalyst is disclosed. The process is preferably used for the preparation of 4-acetoxystyrene from 4,4'-(oxydiethylidene)bisphenol diacetate and 4-methoxystyrene from 4,4'-(oxydiethylidene)bisphenol dimethyl ether. A process for preparing a bisarylalkyl ether by reacting a corresponding arylalkanol in the presence of an acid catalyst is also disclosed.
    Type: Grant
    Filed: May 14, 1991
    Date of Patent: March 16, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: Mohammad Aslam, Brad L. Smith, George Kvakovszky
  • Patent number: 5171915
    Abstract: It is disclosed that aromatic compounds can be alkylated with mono-olefinic HVI-PAO dimer in contact with an acidic catalyst to produce novel alkylated aromatic compositions. It has been found that the novel HVI-PAO dimer alkylated aromatic compositions exhibit an extraordinary combination of properties relating to low viscosity with high viscosity index and low pour point which renders them very useful as lubricant basestock. Further, it has been found that the novel alkylaromatic compositions of the present invention show improved oxidative stability. Depending upon the substituent groups on the aromatic nucleus, useful lubricant additives can be prepared for improved antiwear, antioxidant and other properties. HVI-PAO dimer is prepared as a product or by-product from 1-alkene oligomerization using reduced chromium oxide on solid support.
    Type: Grant
    Filed: February 21, 1989
    Date of Patent: December 15, 1992
    Assignee: Mobil Oil Corporation
    Inventors: Thomas R. Forbus, Bruce P. Pelrine
  • Patent number: 5126461
    Abstract: Process for ring opening compounds of the formula ##STR1## in which R.sup.1 is heteroaryl or aryl, R.sup.2 is a leaving group, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently selected from hydrogen, alkyl, aralkyl, aryl, heteroaryl and alkenyl, provided that at least one of the groups R.sup.3 to R.sup.6 is other than hydrogen, by breaking the bond joining the carbon atom attached to R.sup.3 and the carbon atom attached to R.sup.6 in organic solution using silica, giving useful diene or allyl derivatives, certain of which are novel.
    Type: Grant
    Filed: November 14, 1990
    Date of Patent: June 30, 1992
    Assignee: Shell Research Limited
    Inventors: Mark S. Baird, Ian Bruce
  • Patent number: 5118874
    Abstract: Compounds of the formula ##STR1## in which, independently of one another, each R is OH or lower alkyl having 1-4 carbon atoms and each R' is hydrogen or lower alkyl having 1-4 carbon atoms, are prepared by the condensation of partially fluorinated aromatic hydrocarbons in the presence of hydrogen fluoride or by the reductive coupling of partially fluorinated aromatic compounds. The compounds are used as a starting material for the preparation of partially fluorinated polycondensates.
    Type: Grant
    Filed: June 20, 1991
    Date of Patent: June 2, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Appel, Gunter Siegemund
  • Patent number: 5107044
    Abstract: A process for the bromination of biphenyl, particularly for the preparation of 4-bromobiphenyl or of 4,4'-dibromobiphenyl. The process comprises reacting biphenyl with BrCl. The BrCl may be formed in situ in the reaction medium or may be formed before reaction with biphenyl.
    Type: Grant
    Filed: September 20, 1990
    Date of Patent: April 21, 1992
    Assignee: Rhone-Poulenc Chimie
    Inventor: Alain Nonn
  • Patent number: 5087769
    Abstract: A method of forming 6-substituted-2-vinyl naphthalene from a 2-substituted naphthalene compound wherein the substituent in the 2-position is an ortho-para directing electron-donating group not reactive with hydrogen fluoride, comprises contacting the naphthalene compound and an acylating agent with substantially anhydrous hydrogen fluoride to acylate the naphthalene compound to a 6-substituted-2-acylnaphthalene compound, hydrogenating the 6-substituted-2-acylnaphthalene compound to convert the 2-acyl substituent to an alcohol substituent, dehydrating the product of hydrogenation in the presence of a free radical inhibitor to convert the alcohol substituent to an olefinic substituent, and isolating the formed 6-substituted-2-vinylnaphthalene subsequent to the dehydration.
    Type: Grant
    Filed: September 26, 1990
    Date of Patent: February 11, 1992
    Assignee: Hoechst Celanese Corporation
    Inventors: Mohammad Aslam, Henry C. Linstid, III., Kenneth G. Davenport
  • Patent number: 5072037
    Abstract: A process for the preparation of 2-(4-chlorophenyl)-3-methylbutyric acid from 4-chlorobenzaldehyde by conversion of the benzaldehyde to 3-(4-chlorophenyl)-2-methylpropenal, 3-(4-chlorophenyl)-2-methylpropanol, 1-(4-chlorophenyl)-2-methylpropene-1, and 2-(4-chlorophenyl)-2-methylbutyraldehyde, and finally to the desired corresponding butyric acid.
    Type: Grant
    Filed: December 21, 1990
    Date of Patent: December 10, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jurgen Weber, Peter Lappe, Helmut Springer
  • Patent number: 5017583
    Abstract: Compounds of the Formula I: ##STR1## and pharmaceutically acceptable salts thereof are leukotriene antagonists. These compounds inhibit SRS-A and leukotriene synthesis and are antagonists of SRS-A and are thus useful in the treatment of asthma, allergic disorders, inflammation, skin diseases and certain cardiovascular disorders.
    Type: Grant
    Filed: February 23, 1988
    Date of Patent: May 21, 1991
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Robert N. Young, Joshua Rokach, Haydn R. Williams, Masatoshi Kakushima, Yvan Guindon
  • Patent number: 4965361
    Abstract: Process is disclosed for the preparation of 4-substituted aryl olefins from 4-substituted aryl iodides. 4-Substituted aryl iodides are contacted with an olefin in an ester solvent in the presence of a catalyst system comprising a palladium compound and a Bronsted base.
    Type: Grant
    Filed: February 27, 1989
    Date of Patent: October 23, 1990
    Assignee: Eastman Kodak Company
    Inventor: Kevin J. Edgar
  • Patent number: 4954648
    Abstract: A method for the bromination of aromatic compounds, including substituted deactivated aromatic compounds, at mild temperature conditions is disclosed. The method comprises reacting an aromatic compound with a bromination agent consisting of bromine-trifluoride and bromine at a temperature ranging between -10.degree. C. and 30.degree. C. The bromination reaction takes place instantaneously and the brominated aromatic compound is separated from the original reactant by known organic chemistry techniques.
    Type: Grant
    Filed: May 11, 1989
    Date of Patent: September 4, 1990
    Assignees: Ramot University Authority of Applied Research and Industrial Development Ltd., ICL Industries Ltd.
    Inventors: Ori Lerman, Shlomo Rozen
  • Patent number: 4908152
    Abstract: A novel liquid crystal compound useful as a component of liquid crystal compositions, and particularly suitable to improvement in low temperature characteristics, and a liquid crystal composition containing the compound are provided, which compound is a 2-alkyl-5-[trans-4-(trans-4-alkylcyclohexyl)cyclohexyl]fluorobenzene expressed by the formula ##STR1## wherein R.sup.1 and R.sup.2 each represent an alkyl group of 2 to 10 carbon atoms.
    Type: Grant
    Filed: March 31, 1989
    Date of Patent: March 13, 1990
    Assignee: Chisso Corporation
    Inventor: Yasuyuki Goto
  • Patent number: 4886891
    Abstract: The present invention provides a process for preparing a 1,1-disubstituted ethylene derivative of the formula ##STR1## which comprises reacting lead with a carbinol derivative of the formula ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, X, Y, m and n are defined in the specification. The reaction is conducted more advantageously in the presence of a metal having higher ionization tendency than lead.
    Type: Grant
    Filed: December 18, 1987
    Date of Patent: December 12, 1989
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Shigeru Torii, Masatoshi Taniguchi, Michio Sasaoka, Yoshihisa Tomotaki, Mitsuo Akada, Hideo Tanaka, Akira Suzuki, Shiro Yamashita
  • Patent number: 4879061
    Abstract: A method of making liquid crystalline compounds of the formula ##STR1## where A represents a cyclohexane ring, n has values of 1, 2 or 3, R1 is an alkyl radical, R2 is an alkyl, alkoxy, or alkylcyclohexyl or cyanide radical, and X1 is lower alkyl and X2, X3 and X4 is alkyl and preferably methyl, ethyl or propyl, hydrogen, halogen and preferably fluorine or cyanide and to the compound.
    Type: Grant
    Filed: September 29, 1986
    Date of Patent: November 7, 1989
    Assignee: Crystaloid Electronics Co.
    Inventors: Joseph P. Ferrato, Julie C. Ferrato
  • Patent number: 4871470
    Abstract: Cyclohexane derivatives of formula I ##STR1## wherein R is an alkyl group which has 1-12 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by O, --CO--O-- or --OCO--,A.sup.1 and A.sup.2 each independently of one another are trans-1,4-cyclohexylene or unsubstituted or fluorine-substituted 1,4-phenylene, and one of the groups A.sup.1 and A.sup.2 can also be a single bond,X is --CN, halogen, OH, --COOR.sup.1, --OOCR.sup.1, --COR.sup.1, --OR.sup.1 or R.sup.1 andR.sup.1 is an alkyl group which has 1-12 C atoms and in which one or two CH.sub.2 groups can also be replaced by O, but excluding direct links between two O atoms,with the proviso that, in the case of X=CN, A.sup.2 is trans-1,4-cyclohexylene or fluorine-substituted, 1,4-phenylene, are suitable as components of liquid-crystalline phases.
    Type: Grant
    Filed: October 30, 1987
    Date of Patent: October 3, 1989
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Andreas Wachtler, Joachim Krause, Rudolf Eidenschink, Georg Weber
  • Patent number: 4855292
    Abstract: Novel 4-oxoquinoline-3-carboxylic acid compounds of the formula: ##STR1## wherein R.sup.2 is 1-pyrrolidinyl which may have 1 to 2 substituents selected from the group consisting of (i) C.sub.1 -C.sub.6 alkyl, (ii) amino-(C.sub.1 -C.sub.6)alkyl, said amino being optionally substituted by 1 or 2 substituents selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkanoyl, and C.sub.1 -C.sub.6 alkoxycarbonyl, (iii) amino which may be substituted by 1 or 2 substituents selected from C.sub.1 -C.sub.6 alkyl, phenyl(C.sub.1 -C.sub.6)alkyl, C.sub.1 -C.sub.6 alkoxycarbonyl, and C.sub.1 -C.sub.6 alkanoyl, and (iv) 2-oxo-1,3-dioxolenemethylamino which is substituted by C.sub.1 -C.sub.6 alkyl; or 1-piperidinyl which may have 1 to 3 substituents selected from oxo, hydroxy, halogen and C.sub.1 -C.sub.6 alkyl, and R.sup.3 is C.sub.1 -C.sub.
    Type: Grant
    Filed: July 23, 1987
    Date of Patent: August 8, 1989
    Assignee: Otsuka Pharmaceutical Company, Limited
    Inventors: Hiraki Ueda, Hisashi Miyamoto, Shinji Aki, Tatsuya Otsuka
  • Patent number: 4853151
    Abstract: Dispirotetradecanes of the formula I ##STR1## wherein R.sup.1 and R.sup.2 are each independently of each other alkyl containing 1 to 12 carbon atoms wherein one or more non-adjacent CH.sub.2 groups may also be replaced by --O--, --CO--, --CO--O--, --O--CO--, --O--COO-- and/or --CH.dbd.CH-- (trans), one of the radicals R.sup.1 and R.sup.2 also being H, F, Cl, Br, I, CN, NO.sub.2, NCS,A.sup.1 and A.sup.2 are each independently of each other trans-1,4-cyclohexylene wherein one or two non-adjacent CH.sub.2 groups may be replaced by --O-- and/or --S--, or 1,4-phenylene wherein one or more CH groups may also be replaced by N, with it also being possible optionally for A.sup.1 and A.sup.2 to be substituted laterally or axially by F, Cl, CN, CH.sub.3,Z.sup.1 and Z.sup.2 are each independently of each other --C--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 -- or a single bond,m and n are each 0, 1 or 2,(m+n) 0, 1 or 2,X.sup.1, X.sup.2, X.sup.3 and X.sup.
    Type: Grant
    Filed: August 11, 1987
    Date of Patent: August 1, 1989
    Assignee: Merck Patent Gesellschaft Mit Beschrankfter Haftung
    Inventors: Fritz Vogtle, Wolfgang Calaminus
  • Patent number: 4846998
    Abstract: Cyclohexane derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 Iin whichR.sup.1 and R.sup.2 are each an alkyl group having 1-10 C atoms, in which one or two non-adjacent CH.sub.2 groups can also be replaced by O atoms and/or --CO-- groups and/or --CO--O-- groups and/or --CH.dbd.CH-- groups, one of the radicals R.sup.1 and R.sup.2 also being H, F, Cl, Br, CN or R.sup.3 --A.sup.3 --Z.sup.2 --,A.sup.1 is --A--, A.sup.4 --A-- or --A--A.sup.4 --,A is a trans-1,4-cyclohexylene group which can be substituted in the 2-, 3-, 5- and/or 6-position one or more times by F and/or Cl and/or Br and/or CN and/or an alkyl group or a fluorinated alkyl group which each have 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-- groups and/or --CO--O-- groups, and which may also be substituted in the 1- and/or 4-position,A.sup.2, A.sup.3 and A.sup.
    Type: Grant
    Filed: November 21, 1986
    Date of Patent: July 11, 1989
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Ludwig Pohl, Bernhard Scheuble, Reinhard Hittich, Rudolf Eidenschink, Hans A. Kurmeier, Andreas Wachtler
  • Patent number: 4840953
    Abstract: 9-(Substituted thio)-4H-pyrido[1,2-a]pyrimidin-4-one derivatives of the formula: ##STR1## wherein n is 0 or 1, R is --COR.sup.1, --CONR.sup.4 R.sup.5 or --CH.sub.2 R.sup.6, R.sup.1 is C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.7 cycloalkyl, allythio, styryl, phenoxymethyl, thienylmethyl, C.sub.6 -C.sub.10 aryl optionally substituted, benzyl optionally substituted or 5- or 6-membered heterocyclic group optionally substituted, R.sup.2 and R.sup.3 each is hydrogen, C.sub.1 -C.sub.5 alkyl, carboxy, C.sub.2 -C.sub.5 alkoxycarbonyl or benzyloxycarbonyl optionally substituted, R.sup.4 and R.sup.5 each is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.7 cycloalkyl or phenyl optionally substituted, and R.sup.8 is pyridyl or phenyl optionally substituted) being useful as antiulcer agents are provided through several routes.
    Type: Grant
    Filed: June 15, 1988
    Date of Patent: June 20, 1989
    Assignee: Shionogi & Co., Ltd.
    Inventors: Shigeru Matsutani, Yukio Mizushima, Masami Doteuchi, Yasunobu Ishihara
  • Patent number: 4833250
    Abstract: Carboxylic acid or carboxylic acid halide groups on aryl or heterocyclic aryl rings are directly converted to trihalomethyl groups by using a phenylhalophosphorane, optionally generated in situ by reaction of a phenylphosphonous halide and chlorine.
    Type: Grant
    Filed: March 24, 1988
    Date of Patent: May 23, 1989
    Assignee: ICI Americas Inc.
    Inventor: Elliott Bay
  • Patent number: 4826672
    Abstract: Methods and kits for incorporating a radioactive astatine isotope (particularly .sup.211 At) into an organic compound by electrophilic astatodestannylation of organostannanes.
    Type: Grant
    Filed: June 7, 1985
    Date of Patent: May 2, 1989
    Assignee: President and Fellows of Harvard College
    Inventors: Richard A. Milius, Richard M. Lambrecht, William D. Bloomer
  • Patent number: 4820443
    Abstract: A cyclohexane derivative having a low viscosity, a broad nematic phase temperature range, a good compatibility with other liquid crystal components even at low temperatures and a large positive dielectric anisotropy value, and a liquid crystal composition containing the cyclohexane derivative are provided, which cyclohexane derivative is expressed by the formula ##STR1## wherein R represents an alkyl group of 1-10 C and A represents a hydrogen atom, a halogen atom of F, Cl or Br or a cyano group.
    Type: Grant
    Filed: February 1, 1988
    Date of Patent: April 11, 1989
    Assignee: Chisso Corporation
    Inventors: Yasuyuki Goto, Tetsuya Ogawa
  • Patent number: 4808762
    Abstract: Compounds of the formula ##STR1## in which Ar is substituted or unsubstituted phenyl, naphthyl, or thienyl; Z is oxygen, sulfur, or methylene; and Ar' is 2-methyl[1,1'-biphenyl]-3-yl, 3-phenoxyphenyl, 4-fluoro-3-phenoxyphenyl, or 6-phenoxy-2-pyridyl exhibit pyrethroid-like insecticidal and acaricidal activity and are relatively harmless to aquatic fauna.
    Type: Grant
    Filed: September 9, 1987
    Date of Patent: February 28, 1989
    Assignee: FMC Corporation
    Inventors: Gary A. Meier, Scott M. Sieburth, Thomas G. Cullen, John F. Engel
  • Patent number: 4780468
    Abstract: A novel series of quinolone carboxylic acids for use as antibacterial agents are described. Methods for making the compounds, methods of using the compounds and compositions containing them are also described. Certain novel intermediates are also described.
    Type: Grant
    Filed: August 7, 1987
    Date of Patent: October 25, 1988
    Assignee: Warner-Lambert Company
    Inventors: Alexander J. Bridges, John M. Domagala
  • Patent number: 4739057
    Abstract: A process for converting organic hydroxyl-containing compounds to halides which comprises reacting the hydroxyl-containing compound with a phosphorushalide reagent of formula: R.sub.n PX.sub.5-n wherein n is selected from 1, 2 and 3; R is selected from the group consisting of C-6 to C-10 aryl and substituted aryl wherein the substituents are selected from the group consisting of straight and branched chain alkyl, alkoxy, and haloalkyl, halogen, sulfonate and mixtures thereof; and X is a halogen. It is preferred to carry out the reaction in the presence of an arylphosphorusoxydihalide solvent. The use of an arylphosphorustetrahalide and particularly phenylphosphorustetrachloride is preferred. The arylphoshorustetrahalide can be prepared in situ by contacting a solution of the corresponding arylphosphorusdihalide in an arylphosphorusoxydihalide solvent with a halogen. The process can further comprise the step of heating the reaction mixture. Maintaining a reaction temperature of from about 0.degree. C.
    Type: Grant
    Filed: June 30, 1986
    Date of Patent: April 19, 1988
    Assignee: Stauffer Chemical Co.
    Inventors: Andrea Leone-Bay, Elliott Bay, Peter E. Timony
  • Patent number: 4724097
    Abstract: New bicyclohexylethanes of formula IR1--Cy--Cy--CH2CH2--A--(Cy)n--R2 (I)wherein R1 is alkyl; R2 is alkyl, in which one or two non-adjacent CH.sub.2 groups can be replaced by 0 atoms, or is F, Cl, Br, CN, --COOalkyl or --O--CO--alkyl; or one of the radicals R.sup.1 and R.sup.2 can also be H; A is Cy, or 1,4-phenylene which is unsubstituted or substituted by one or two F and/or Cl atoms and/or CH.sub.3 groups or by a CN group; Cy is 1,4-cyclohexylene and n is 0 or 1; the alkyl groups in each case containing 1-10 C atoms, with the proviso that n is 1 if A is Cy and R2 is CN, can be used as constituents of dielectrics for electrooptical display elements.
    Type: Grant
    Filed: May 21, 1986
    Date of Patent: February 9, 1988
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Michael Romer, Rudolf Fidenschink, Joachim Krause, Bernhard Scheuble, Georg Weber
  • Patent number: 4723005
    Abstract: New anisotropic compounds of the formula (1) are useful in liquid crystal mixtures for electrooptical displays; at least one of the end groups of the compounds (1) is an alkyl group which carries cyano or halogen in a terminal or non-terminal position. This offers advantages for longitudinal polarization and/or cross-polarization of the anisotropic compounds with the aid of the comparatively highly polarizing cyano or halogen substituents, in particular high clear points, low .DELTA..epsilon./.epsilon..perp. values and/or negative .DELTA..epsilon. values.
    Type: Grant
    Filed: September 10, 1984
    Date of Patent: February 2, 1988
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Tuong Huynh-Ba, Maged A. Osman
  • Patent number: 4710315
    Abstract: Anisotropic compounds of the formula (1) specified in claim 1 are suitable, owing to their low .DELTA..epsilon./.epsilon..perp. values for liquid crystal displays which have high information densities of for examples up to 10.sup.6 image dots and accordingly need to be highly multiplexible; compared with known compounds they offer improved application properties and are relatively simple to synthesize.
    Type: Grant
    Filed: December 16, 1985
    Date of Patent: December 1, 1987
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Hans P. Schad, Stephen M. Kelly
  • Patent number: 4695398
    Abstract: A compound which, when used as a component of a liquid crystal composition, has an effectiveness of notably reducing the viscosity and the operating voltage of the resulting liquid crystal composition, and a liquid crystal composition containing the same are provided, which compound is a cyclohexane derivative expressed by the formula ##STR1## wherein R represents hydrogen atom or an alkyl group of 1 to 10 carbon atoms.
    Type: Grant
    Filed: March 12, 1986
    Date of Patent: September 22, 1987
    Assignee: Chisso Corporation
    Inventors: Yasuyuki Goto, Tetsuya Ogawa, Shigeru Sugimori
  • Patent number: 4694104
    Abstract: The invention relates to polyoxyalkylene quaternized salts as phase transfer catalysts for liquid/liquid phase cyclopropanation, substitution or addition reactions involving a normally liquid or solvent soluble olefinically unsaturated hydrocarbon and the process in which said quaternary compound is utilized. The involved quaternized salts are defined by the formula: ##STR1## wherein R is alkyl having 8 to 30 carbon atoms, blends thereof or alkyl-substituted phenyl of 10 to 24 carbon atoms;n has a value of from 2 to 14 and includes mixtures within said range;R.sub.1 and R.sub.2 are hydrogen atoms or one of R.sub.1 and R.sub.2 is methyl;R.sub.3, R.sub.4 and R.sub.5 are independently hydrogen, an alkyl radical of 1 to 6 carbon atoms or phenyl or one of R.sub.3, R.sub.4 and R.sub.5 is an .beta.-ethyl-alkali metal sulfonate;A is a phosphorous or a nitrogen atom; and halo is a chlorine or bromine ion.
    Type: Grant
    Filed: August 9, 1982
    Date of Patent: September 15, 1987
    Assignee: GAF Corporation
    Inventors: Paritosh M. Chakrabarti, Sureshchandra G. Desai, Lindley S. Wood, Jr.
  • Patent number: 4690948
    Abstract: Ring opened halogenated Resorcyclic Acid Lactone (RAL) derivatives having the structure: ##STR1## are used to increase rumen fermentation efficiency.
    Type: Grant
    Filed: December 1, 1986
    Date of Patent: September 1, 1987
    Assignee: International Minerals & Chemical Corp.
    Inventor: Jing-Jong Lu
  • Patent number: 4686289
    Abstract: New anisotropic compounds with a cross-polarizing substituent have the formula (1) ##STR1## The increase in .epsilon..perp. is achieved by the polarizing group X, preferably the cyano group or a halogen atom, which is not laterally on the ring, as with the known compounds, but is on the bridge, that is to say is part of the main bridge bonding rings A and B to one another. Ring A has the formula (1a) or (1b) given herein and is always cycloaliphatic, while ring B can be identical to ring A or is an aromatic ring of the formula (1c) or (1d) herein. R.sup.1 and R.sup.2 are identical or different end groups of the formula (1e) herein.The radical X on the bridge causes less widening of the molecule than a radical X on a ring, which provides comparatively higher clear points and moreover enables aromatic rings to be omitted from the anisotropic compounds.
    Type: Grant
    Filed: February 25, 1986
    Date of Patent: August 11, 1987
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Tuong Huynh-Ba, Maged A. Osman
  • Patent number: 4665246
    Abstract: The process of producing ethynyl aromatic compounds which are useful as intermediates in the preparation of 3-dimensional carbon-carbon structures for aerospace and military applications and as starting materials in the preparation of organic semi-conductors. The ethynyl aromatic compounds may be any of the classes illustrated in FIGS. 1, 2 and 3 of the drawing. Starting compounds for the process may by any compound from the classes illustrated in FIGS. 4, 5 and 6. The starting compound is reacted in the presence of a Friedel-Crafts catalyst in a suitable solvent with an acyl compound from the class illustrated in FIG. 7 to yield a compound within the classes illustrated in FIGS. 8, 9 and 10. The carbonyl groups in this compound are reduced to yield a corresponding alcohol. Each hydroxy group in the alcohol is converted to an easily eliminatable group, e.g., by reacting it with methane sulfonyl chloride, when subjected to basic conditions.
    Type: Grant
    Filed: March 9, 1984
    Date of Patent: May 12, 1987
    Assignee: Chem Biochem Research, Inc.
    Inventor: Chris Anderson
  • Patent number: 4637897
    Abstract: Nematic compounds with a negative DC antisotropy, characterized by the formula I ##STR1## in which m=1 or 2, r is zero or 1 and m+r=1 or 2, and R.sup.1 and R.sup.2 are identical or different and are selected from alkyl and alkoxy groups each having 1-12 carbon atoms in a straight or branched chain, which may be chiral, Z is a bridge member selected from a single bond and the groups of the formulae --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --O--CO-- or --CO--O--, one of the groups X and Y is selected from fluorine, chlorine, bromine and cyano and the other of the groups X and Y is selected from hydrogen, fluorine, chlorine, bromine and cyano, with the proviso that m=r=1 if X and Y are both cyano, are suitable as components for liquid crystal mixtures having an overall negative DC anisotropy, such as are required in particular for electro-optical displays of the type of guest/host displays or homotropic-nematic displays.
    Type: Grant
    Filed: August 6, 1984
    Date of Patent: January 20, 1987
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventor: Stephen M. Kelly
  • Patent number: 4627933
    Abstract: Compounds of the formulaR.sup.1 --Q.sup.1 --(CH.sub.2).sub.m --(COO).sub.n --(CH.sub.2).sub.p --Q.sup.2 --R.sup.2whereinR.sup.1 and R.sup.2 are each independently alkyl or alkoxy each of 1-12 C atoms, F, Cl, Br, CN or --Q.sup.3 --R.sup.3, or one of R.sup.1 and R.sup.2 can also be H;Q.sup.1, Q.sup.2 and Q.sup.3 are each independently 1,4-phenylene, 1,4-cyclohexylene, 1,4-bicyclo(2,2,2)-octylene or 1,3-dioxane-2,5-diyl, each of which is unsubstituted or substituted by 1-4 fluorine, chlorine or bromine atoms;R.sup.3 is alkyl or alkoxy each of 1-8 C atoms, H, F, Cl, Br or CN;m is 1, 2, 3, 4, 5 or 6; n is 0 or 1; and p is 0, 1, 2, 3, 4 or 5; the sum of (m+p) being 2, 4 or 6 and the sum of (m+n+p) being at least 3;but with the proviso that Q.sup.3 is unsubstituted 1,4-phenylene or 1,4-phenylene substituted by a fluorine, chlorine or bromine atom, only when n=1 or (m+p)=6 or at least one of R.sup.1 or R.sup.3 is F, Cl or Br or none of R.sup.1 to R.sup.3 is CN or two of the radicals R.sup.1 to R.sup.
    Type: Grant
    Filed: July 7, 1983
    Date of Patent: December 9, 1986
    Assignees: Merck Patent Gesellschaft mit beschrankter Haftung, The Secretary of State for Defense in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Rudolf Eidenschink, Joachim Krause, Beatrice M. Andrews, George W. Gray, Neil Carr
  • Patent number: 4620938
    Abstract: New hydroterphenyls of formula IR.sup.1 --Cy--Cy--Ph--R.sup.2 Iwherein R.sup.1 is alkyl; R.sup.2 is H, F, Cl, Br, I, OH, CN, alkyl, --O-alkyl, --COOR.sup.3 or --O--CO--R.sup.3 ; R.sup.3 is H, alkyl, --Cy-alkyl, --Ph-alkyl, --Ph--O-alkyl, --Ph--CN or --Ph--F; Cy is 1,4-cyclohexylene; and Ph is 1,4-phenylene; can be used as dielectrics for electrooptical display elements.
    Type: Grant
    Filed: April 5, 1985
    Date of Patent: November 4, 1986
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Michael Romer, Joachim Krause, Rudolf Eidenschink, Georg Weber
  • Patent number: 4606845
    Abstract: New bicyclohexylethanes of formula IR.sup.1 --Cy--Cy--CH.sub.2 CH.sub.2 --A--(Cy).sub.n --R.sup.2 (I)wherein R.sup.1 is alkyl; R.sup.2 is alkyl, in which one or two non-adjacent CH.sub.2 groups can be replaced by O atoms, or is F, Cl, Br, CN, --COOalkyl or --O--CO-alkyl; or one of the radicals R.sup.1 and R.sup.2 can also be H; A is Cy, or 1,4-phenylene which is unsubstituted or substituted by one or two F and/or Cl atoms and/or CH.sub.3 groups or by a CN group; Cy is 1,4-cyclohexylene and n is 0 or 1; the alkyl groups in each case containing 1-10 C atoms, with the proviso that n is 1 if A is Cy and R.sup.2 is CN,can be used as constituents of dielectrics for electrooptical display elements.
    Type: Grant
    Filed: May 14, 1984
    Date of Patent: August 19, 1986
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Michael Romer, Rudolf Eidenschink, Joachim Krause, Bernhard Scheuble, Georg Weber
  • Patent number: 4590281
    Abstract: Provided is a process for preparing an aldehyde or aldehydes represented by the following formula (III), characterized in that a diaryliodonium salt represented by the following formula (I) is reacted with an unsaturated alcohol represented by the following formula (II) in a solvent containing a base in the presence of a transition metal catalyst at a temperature in the range of room temperature to 100.degree. C.:[Ar.sub.1 --I.sup..sym. --Ar.sub.2 ] X.sup..crclbar. (I)CHR.sub.1 .dbd.CR.sub.2 --CH.sub.2 OH (II)Ar.sub.3 --CHR.sub.1 --CHR.sub.2 --CHO (III)wherein Ar.sub.1 and Ar.sub.2, which may be alike or different, are each an aryl group which may have a substituent group or groups, X.sup..crclbar. is a counter ion which is inert to the above reaction, Ar.sub.3 is the same aryl group as Ar.sub.1 or Ar.sub.2, and R.sub.1 and R.sub.2 are each hydrogen atom or an alkyl group of C.sub.1 to C.sub.12.
    Type: Grant
    Filed: March 7, 1984
    Date of Patent: May 20, 1986
    Assignee: Nippon Petrochemicals Company
    Inventors: Yasuo Yamazaki, Takehiko Suzuki
  • Patent number: 4571438
    Abstract: A process for the preparation of olefinic aldehydes and intermediates is disclosed. The condensation of an .alpha.,.omega.-dihalide with a metal acetylide gives an acetylenic halide which can be reduced to give an olefinic halide, then oxidized to give the desired olefinic aldehyde or the acetylenic halide can be oxidized first to give an acetylenic aldehyde and then reduced to give the desired olefinic aldehyde.
    Type: Grant
    Filed: March 21, 1985
    Date of Patent: February 18, 1986
    Assignee: Phillips Petroleum Company
    Inventors: Jim D. Byers, Dennis S. Banasiak
  • Patent number: 4567280
    Abstract: In a process for producing an iodo-aromatic compound which comprises iodinating an aromatic compound having an electron-donating substituent bonded to the benzene ring with iodine in the presence of a solvent, the improvement wherein about 1/2 to about 10 moles, per mole of iodine added to the reaction system, of nitrogen dioxide (NO.sub.2) is added in the form of NO.sub.2 to the reaction system, and the reaction is carried out in the presence of nitrogen dioxide.
    Type: Grant
    Filed: September 4, 1984
    Date of Patent: January 28, 1986
    Assignee: UBE Industries, Ltd.
    Inventors: Hiroshi Itatani, Mikito Kashima, Yasutaka Tasaki
  • Patent number: 4562286
    Abstract: A multi-step process is described for preparing a methoxytrifluoromethylnaphthoic acid compound of formula ##STR1## from 1,5-dimethylnaphthalene and for preparing novel intermediate compounds of formula ##STR2## where X is chlorine or fluorine. Methoxytrifluoromethylnaphthoic acid is useful for preparing biologically active compounds such as naphthyl thioamide derivatives which inhibit aldose reductase activity.
    Type: Grant
    Filed: November 1, 1984
    Date of Patent: December 31, 1985
    Assignee: Occidental Chemical Corporation
    Inventor: Arthur M. Foster