Oxy, Not Bonded Directly To A Ring, In Same Side Chain As Ester Function Patents (Class 560/60)
  • Patent number: 5360819
    Abstract: A release tag reagent suitable for use in the chemical analysis of a substance to be detected, which substance contains reactive groups, such as for, but not limited to gas phase detection groups, which reagent comprises three covalently bonded groups: a signal group which on release provides a ketone signal compound to be detected, a release group which may be cleaved to release the ketone signal group, which release group contains, for example, a vic glycol or an olefin group and a reactivity group which is reactive with a reactive group of the substance to be detected.
    Type: Grant
    Filed: March 11, 1985
    Date of Patent: November 1, 1994
    Assignee: Northeastern University
    Inventor: Roger W. Giese
  • Patent number: 5352701
    Abstract: 1. Leukotriene-B.sub.4 antagonists of formula I ##STR1## are described, in which X is a CH.sub.2 group or an oxygen atom,Y is C.sub.1 -C.sub.4 -alkoxy or --S(O).sub.p --C.sub.1 -C.sub.4 -alkyl,p is 0, 1 or 2Z is a hydrogen atom or the radical A-B-COOH with A being a hydroxymethylene group or a carbonyl group and B being an alkylene group with 1-6 atoms in the chain or a radical ##STR2## with the exception that B cannot mean the radical ##STR3## if X is a CH.sub.2 group, R.sub.1 is the radical OH, --O--(C.sub.1 --C.sub.4) -alkyl, --O--(C.sub.3-C.sub.6) -cycloalkyl, --O--(C.sub.7-C.sub.12) -aralkyl or the radical NHR.sub.4 with R.sub.4 being hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.3 -C.sub.6)-cycloalkyl, C.sub.6 -C.sub.10 -aryl or (C.sub.7 -C.sub.12)-aralkyl as well as their salts with physiologically compatible bases and their cyclodextrin clathrates, process for their production and their use as pharmaceutical agents.
    Type: Grant
    Filed: May 5, 1993
    Date of Patent: October 4, 1994
    Assignee: Schering Aktiengesellschaft
    Inventors: Josef Heindl, Werner Skuballa, Bernd Buchmann, Wolfgang Frohlich, Roland Ekerdt, Claudia Giesen
  • Patent number: 5350873
    Abstract: Optically active compounds of the formula I ##STR1## where R is C.sub.1 -C.sub.12 -alkyl or -perfluoroalkyl in which one or two non-adjacent CH.sub.2 or CF.sub.2 groups can also be replaced by --O-- and/or --CO-- and/or --CO--O-- and/or --CH.dbd.CH-- and/or --CH-halogen-- and/or --CHCN-- and/or --0--CO--CH-halogen-- and/or --O--CO--CHCN--, or is C.sub.1 -C.sub.12 -alkyl which can have a terminal chemically reactive group and in which a CH.sub.2 group can be replaced by --O--,A.sup.1 and A.sup.2 are each, independently of one another, 1,4-phenylene which is unsubstituted or substituted by one or two F and/or Cl and/or Br atoms and/or CH.sub.3 groups and/or CN groups and in which one or two CH groups can also be replaced by N, 1,4-cyclohexylene in which one or two non-adjacent CH.sub.2 groups can also be replaced by --O-- and/or --S--, 1,4-piperidinediyl, 1,4-bicyclo[2.2.2]octylene, 2,6-naphthalenediyl, decahydro-2,6-naphthalenediyl or 1,2,3,4-tetrahydro-2,6-naphthalenediyl,A.sup.
    Type: Grant
    Filed: August 13, 1992
    Date of Patent: September 27, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Volker Bach, Wolfgang Brox, Karl-Heinz Etzbach, Axel Paul, Karl Siemensmeyer
  • Patent number: 5347039
    Abstract: This invention is directed to a method for stereoselectively preparing a syn-dihydroxylated compound comprising reacting a 3-hydroxyket-1-one with a borohydride in the presence of titanium derivative.
    Type: Grant
    Filed: August 11, 1993
    Date of Patent: September 13, 1994
    Assignee: Rhone-Poulenc Rorer S.A.
    Inventors: Patrick Leon, Xavier Radisson, Viviane Massonneau
  • Patent number: 5334748
    Abstract: Fungicidal compounds of the formula (I): ##STR1## and stereoisomers thereof, wherein K is oxygen or sulphur; Z is optionally substituted aryl or optionally substituted heteroaryl; X is O, S(O).sub.n, NR.sup.4, CR.sup.1 R.sup.2 CHR.sup.5, CO, CR.sup.1 (OR.sup.2), C.dbd.CR.sup.1 R.sup.2, CHR.sup.1 CHR.sup.2, CR.sup.1 .dbd.CR.sup.2, CHR.sup.1 CR.sup.2 .dbd.CH, C.tbd.C, OCHR.sup.1, CHR.sup.1 O, OCHR.sup.1 O, S(O).sub.n CHR.sup.1 S(O).sub.n CHR.sup.1 O, CHR.sup.1 S(O).sub.n, CHR.sup.1 OSO.sub.2, NR.sup.4 CHR.sup.1, CHR.sup.1 NR.sup.4, CO.sub.2, O.sub.2 C, SO.sub.2 O, OSO.sub.2, CO.CO, COCHR.sup.1, COCHR.sup.1 O, CHR.sup.1 CO, CHOH.CHR.sup.1, CHR.sup.1.CHOH ##STR2## CONR.sup.4, OCONR.sup.4, NR.sup.4 CO, CSNR.sup.4, OCS.NR.sup.4, SCO.NR.sup.4, NR.sup.4 CO.sub.2, NR.sup.4 CS, NR.sup.4 CSO, NR.sup.4 COS, NR.sup.4 CONR.sup.4, S(O).sub.n NR.sup.4, NR.sup.4 S(O).sub.n, CS.sub.2, S.sub.2 C, CO.S, SCO, N.dbd.N, N.dbd.CR.sup.1, CR.sup.1 .dbd.N, CHR.sup.1 CHR.sup.2 CH(OH), CHR.sup.1 OCO, CHR.sup.1 SCO, CHR.sup.1 NR.sup.
    Type: Grant
    Filed: September 9, 1988
    Date of Patent: August 2, 1994
    Assignee: Imperial Chemical Industries PLC
    Inventors: Alan J. Buckley, Michael G. Huchings, Ian Ferguson, Kevin Beautement, John M. Clough, Patrick J. Crowley, Christopher R. A. Godfrey, Paul J. deFraine, Vivienne M. Anthony, Stephen P. Heaney
  • Patent number: 5334607
    Abstract: Antimycotics containing a compound of the formula ##STR1## where .dbd.Y is .dbd.CH--OCH.sub.3, .dbd.CH--CH.sub.3, .dbd.CH--CH.sub.2 --CH.sub.3, .dbd.CH--SCH.sub.3 or .dbd.N--OCH.sub.3, and X is oxygen, or X may also be NH if Y is .dbd.N--OCH.sub.3,Z is halogen, nitro, cyano, unsubstituted or substituted organic radicals, OR.sup.12, SR.sup.13, SOR.sup.14, SO.sub.2 R.sup.15, --COOR.sup.16, --CONR.sup.17 R.sup.18, --COR.sup.19, --CR.sup.20 .dbd.NR.sup.21, --N.dbd.CR.sup.22 R.sup.23, --CR.sup.24 .dbd.N--OR.sup.25, --CR.sup.25 R.sup.26 --O--N.dbd.CR.sup.27 R.sup.28 andU, V, W can be hydrogen or one of the meanings given for Z, or where two of Z, U, V and W in adjacent positions on the phenyl ring can form an unsubstituted or substituted five- or six-membered, aromatic or aliphatic ring which may contain one to three hetero atoms (N, S, O), and R.sup.12 to R.sup.26 are identical or different and are hydrogen, unsubstituted or substituted organic radicals,are used for controlling mycoses.
    Type: Grant
    Filed: May 28, 1992
    Date of Patent: August 2, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Hubert Sauter, Gisela Lorenz, Gerd Steiner, Bernd Janssen, Timm Anke, Wolfgang Steglich
  • Patent number: 5332857
    Abstract: Variously substituted 3,5-dihydroxy-6,8-nonadienoic acids and esters, are blood cholesterol lowering agents and so are useful in the prevention and treatment of cardiovascular diseases such as atherosclerosis.
    Type: Grant
    Filed: July 6, 1992
    Date of Patent: July 26, 1994
    Assignee: Pfizer Inc.
    Inventors: Peter A. McCarthy, Frederick J. Walker
  • Patent number: 5330739
    Abstract: Compounds having the structure ##STR1## wherein (Z--COO is the residue of an iodinated aromatic acid; R is alkyl, cycloalkyl, aryl, aralkyl, ##STR2## or alkenyl; R.sup.1 is H, alkyl, cycloalkyl, aryl, aralkyl, or --CH.sub.2 --.sub.m CO.sub.2 R.sup.3 ;R.sup.2 is H, alkyl, cycloalkyl, aryl, aralkyl, --CH.sub.2 --.sub.n CO.sub.2 R.sup.4, or a ##STR3## group, wherein Z, R and R.sup.1 are as defined above;or R.sup.1 and R.sup.2, taken together with the carbon atom to which they are attached represent cycloalkyl;R.sup.3 is H, alkyl, cycloalkyl, aryl or aralkyl;R.sup.4 is H, alkyl, cycloalkyl, aryl or aralkyl; andm, n and p are independently an integer of from 0 to 17;provided that R.sup.1 and R.sup.2 can not both be H;are useful in the preparation of x-ray contrast compositions for medical imaging.
    Type: Grant
    Filed: December 4, 1992
    Date of Patent: July 19, 1994
    Assignee: Sterling Winthrop Inc.
    Inventor: Carl R. Illig
  • Patent number: 5318994
    Abstract: Compounds of the formula: ##STR1## in which: A represents ##STR2## R represents linear or branched lower alkyl, R.sub.1 represents hydrogen or linear or branched lower alkyl, andR.sub.2 represents aryl or lower arylalkyl or aryl or lower arylalkyl substituted by lower alkyl, lower alkoxy, trifluoromethyl, or halogen, aryl means phenyl or naphthyl, as well as optical isomers, epimers and diastereoisomers and addition salts thereof with a pharmaceutically-acceptable acid, lower alkyl and lower alkoxy having 1 to 6 carbon atoms inclusive, andmedicaments containing the same which are useful for the treatment of disorders of the melatoninergic system.
    Type: Grant
    Filed: November 3, 1992
    Date of Patent: June 7, 1994
    Assignee: Adir et Compagnie
    Inventors: Jean Andrieux, Raymond Houssin, Said Yous, Beatrice Guardiola, Daniel Lesieur
  • Patent number: 5315025
    Abstract: This invention relates to derivatives of acrylic acid useful as fungicides, to processes for preparing them, to fungicidal compositions containing them, and to methods of combating fungi, especially fungal infections in plants, using them.
    Type: Grant
    Filed: March 29, 1991
    Date of Patent: May 24, 1994
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael J. Bushell, Kevin Beautement, John M. Clough, Vivienne M. Anthony, Paul deFraine, Christopher R. Godfrey
  • Patent number: 5312950
    Abstract: A method for the purification of alcohols from organic soluble impurities has been discovered comprising treating the crude alcohol with a cyclic anhydride followed by an aqueous base and extracting the corresponding half-ester into aqueous solution leaving the impurities in organic solution. This method is particularly useful for the separation of chiral, nonracemic alcohols from the corresponding antipodal ester (the mixture resulting from an enzymatic kinetic resolution) because the separation is non-chromatographic and the enantiomeric integrity of the products is maintained.
    Type: Grant
    Filed: August 31, 1993
    Date of Patent: May 17, 1994
    Assignee: Eastman Kodak Company
    Inventor: Neil W. Boaz
  • Patent number: 5310746
    Abstract: All possible stereoisomer forms and mixtures of a compound of the formula ##STR1## wherein X is a halogen, R.sub.2 and R.sub.3 are individually selected from the group consisting of alkyl and cycloalkyl of up to 8 carbon atoms optionally substituted with at least one halogen, R.sub.1 is selected from the group consisting of alkyl, alkenyl, alkynyl and cycloalkyl of up to 12 carbon atoms optionally substituted with at least one halogen, aryl and heteroaryl of 5 to 6 ring members optionally substituted with at least one member of the group consisting of halogen, alkyl, alkenyl, alkynyl and cycloalkyl of up to 8 carbon atoms optionally substituted with at least one member of the group consisting of --NO.sub.2, --NH.sub.2, --CN, --OR', --SR", --SOR", --SO.sub.2 R", --NR"'.sub.2, --Ar, OAr.sub.1 and SAr.sub.2, R', R" and R"' are individually selected from the group consisting of alkyl, alkenyl, alkynyl and cycloalkyl of up to 12 carbon atoms optionally substituted by at least one halogen, Ar, Ar.sub.1 and Ar.sub.
    Type: Grant
    Filed: November 24, 1992
    Date of Patent: May 10, 1994
    Assignee: Roussel Uclaf
    Inventors: Jean-Louis Brayer, Jean-Pierre Demoute, Yannick Le Stanc, Nicole Reinier
  • Patent number: 5294724
    Abstract: 4-Hydroxytetrahydropyran-2-ones and the corresponding dihydroxycarboxylic acid derivatives, salts and esters, process for their preparation, their use as pharmaceuticals, and pharmaceutical preparations and precursors.Compounds of the formula I ##STR1## and the corresponding open-chain dihydroxycarboxylic acids of the formula II ##STR2## in which X, Y, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 have the meanings indicated, and also their pharmacologically tolerable salts with bases and their pharmacologically tolerable esters, processes for the preparation of these compounds, their use as pharmaceuticals and pharmaceutical preparations are described. In addition, compounds of the formula III ##STR3## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, X and Y have the meanings indicated are described.
    Type: Grant
    Filed: September 6, 1990
    Date of Patent: March 15, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Heiner Jendralla, Gunther Wess, Kurt Kesseler, Gerhard Beck
  • Patent number: 5294639
    Abstract: Abstract of the Disclosure: .alpha.-Arylacrylic acid derivatives of the general formula I ##STR1## where X is ethylene or ethenylene;Y is a direct bond or oxygen;R.sup.1 is an unsubstituted or substituted mononuclear or dinuclear aromatic or heteroaromatic system;R.sup.2 is cyano, nitro, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio or haloalkylthio;n is 1 or 2, and the radicals may be different if n is 2, and(c m is 0, 1 or 2, and the radicals may be different if m is 2,with the proviso that R.sup.1 is not phenyl when n is 1 and m is 0, their preparation, insecticides and fungicides containing them and methods for their use.
    Type: Grant
    Filed: September 4, 1991
    Date of Patent: March 15, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Reinhard Kirstgen, Albrecht Harreus, Uwe Kardorff, Thomas Kuekenhoehner, Harald Rang, Gisela Lorenz, Eberhard Ammermann, Christoph Kuenast
  • Patent number: 5294731
    Abstract: A process for the preparation of .beta.-hydroxycarboxylates of the general formula I ##STR1## in which R.sup.1 and R.sup.2 individually denoteC.sub.1 -C.sub.20 alkyl optionally substituted by C.sub.1 -C.sub.8 alkoxy and/or halogen, C.sub.3 -C.sub.20 alkoxycarbonylalkyl, C.sub.2 -C.sub.20 alkenyl, C.sub.5 -C.sub.30 acetalalkenyl, aryl optionally mono- to penta-substituted by C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy, and/or halogen, C.sub.7 -C.sub.20 aralkyl, C.sub.7 -C.sub.20 aralkenyl, hetaryl, C.sub.3 -C.sub.20 cycloalkyl, or C.sub.4 -C.sub.20 cycloalkylalkyl,or together denote a C.sub.2 -C.sub.8 alkylene chainand one or other of R.sup.1 and R.sup.2 denotes hydrogen, andR.sup.3 denotes hydrogen, C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.sub.20 alkenyl, aryl optionally mono- to penta-substituted by C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy, and/or halogen, C.sub.7 -C.sub.20 aralkyl, C.sub.3 -C.sub.20 cycloalkyl, or C.sub.4 -C.sub.20 cycloalkylalkyl, andR.sup.4 denotes C.sub.1 -C.sub.20 alkyl, C.sub.
    Type: Grant
    Filed: March 23, 1993
    Date of Patent: March 15, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Joachim Paust, Wolfgang Siegel
  • Patent number: 5292946
    Abstract: The present invention is directed to in-situ preparation of diisopinocamphenylchloroborane, and the use of same in the reduction of prochiral ketones to optically active alcohols such as those of formula B. ##STR1## The compound of Formula B is useful in the production 2,5-diaryltetrahydrofurans useful as PAF antagonists.
    Type: Grant
    Filed: March 23, 1992
    Date of Patent: March 8, 1994
    Assignee: Merck & Co., Inc.
    Inventors: Pamela M. Simpson, David M. Tschaen, Thomas R. Verhoeven
  • Patent number: 5290950
    Abstract: Disclosed is a tetra substituted cyclohexane having an ionophore in the one and two positions wherein the ionophore may be the same or different and is selected from the group consisting of a crown, a podand and a cryptand wherein the ionophore is capable of complexing with a metal or ammonium cation. Positions four and five are substituted by an electron donor group and an electron acceptor group. Also disclosed is a method for detecting the concentration of cations in a fluid by subjecting the fluid to the tetra substituted cyclohexane composition which will thereby complex the cation in the fluid. The cations are preferably alkali metal and alkaline earth metal cations. The fluid may be an aqueous or non-aqueous fluid or body fluids.
    Type: Grant
    Filed: November 27, 1991
    Date of Patent: March 1, 1994
    Assignee: Wayne State University
    Inventors: Morton Raban, David T. Durocher
  • Patent number: 5286895
    Abstract: An acyclic tricarboxylic compound has been isolated from a culture of MF5453. The compound and its derivatives are active as squalene synthetase inhibitors and are useful in the treatment of hypercholesterolemia.
    Type: Grant
    Filed: December 7, 1992
    Date of Patent: February 15, 1994
    Assignee: Merck & Co., Inc.
    Inventors: Guy H. Harris, Henry Joshua, Deborah L. Zink
  • Patent number: 5278338
    Abstract: A method for racemizing an optically active carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen, hydroxy, halo, cyano, C.sub.1 to C.sub.6 linear or branched alkoxy, amino or substituted amino or the group ##STR2## is nitrile; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched haloalkyl, aralkyl, cycloalkyl, alkyl substituted cycloalkyl, C.sub.6 to C.sub.10 aryl, C.sub.1 to C.sub.6 linear or branched alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.1 to C.sub.6 alkylthio, C.sub.3 to C.sub.8 cycloalkylthio, C.sub.6 to C.sub.10 arylthio, C.sub.6 to C.sub.10 arylcarbonyl, C.sub.4 to C.sub.8 cycloalkenyl, trifluoromethyl, halo, C.sub.4 to C.sub.5 heteroaryl, C.sub.10 to C.sub.14 aryl, or biphenyl unsubstituted or substituted with methyl or halo, comprising heating said optically active carboxylic acid or ester thereof in the presence of water at a temperature of from about 40.degree. C.
    Type: Grant
    Filed: November 4, 1992
    Date of Patent: January 11, 1994
    Assignee: Ethyl Corporation
    Inventor: Rhonda L. Trace
  • Patent number: 5278337
    Abstract: A process for obtaining a substantially pure enantiomer of an aryl-substituted aliphatic carboxylic acid is described. The process utilizes first an enantiomerically enriched mixture the of aryl-substituted aliphatic carboxylic acid obtained from kinetic resolution, diastereomeric crystallization or asymmetric synthesis processes. This enriched mixture is reacted with a base producing a salt that has the following properties:1) has at least one eutectic point;2) a composition that is not at the eutectic point; and3) a eutectic composition that is closer to the racemic composition than is the eutectic composition of said aryl-substituted carboxylic acid.Substantially pure, enantiomeric salt is separated, leaving a mother liquor comprising the solvent and aryl-substituted aliphatic carboxylic acid enriched in the other enantiomer.
    Type: Grant
    Filed: October 14, 1992
    Date of Patent: January 11, 1994
    Assignee: Ethyl Corporation
    Inventors: Thanikavelu Manimaran, G. Patrick Stahly, R. Carl Herndon, Jr.
  • Patent number: 5274168
    Abstract: Disclosed are novel active benzene derivatives represented by the general formula (I): ##STR1## (wherein X represents --COO--, --OCO--, --CH.sub.2 O-- 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: Grant
    Filed: December 4, 1992
    Date of Patent: December 28, 1993
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takayuki Higashii, Masayoshi Minai
  • Patent number: 5274155
    Abstract: A process for the preparation of compounds of formula ##STR1## and pharmaceutically acceptable salts thereof; wherein X is --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --C.tbd.C-- or --CH.sub.2 O-- (where O is linked to Z); Z is a hydrophobic anchor R.sub.1 is hydrogen, alkyl, cycloalkyl or aryl; comprising the steps of:(A) reacting a compound of formula ##STR2## with a compound of formula ##STR3## or a compound of formula ##STR4## in the presence of an amine base or an alkali metal hydride in an organic solvent to form a compound having the formula ##STR5## (B) heating the compound of formula IX at a temperature of from about 100.degree. C. to about 200.degree. C., to form a compound of formula ##STR6## and (C) quenching the compounds of formula VIII with an acid provides the compounds of formula I.
    Type: Grant
    Filed: December 7, 1992
    Date of Patent: December 28, 1993
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: John K. Thottathil, David Kronenthal
  • Patent number: 5266720
    Type: Grant
    Filed: July 8, 1991
    Date of Patent: November 30, 1993
    Assignee: Cancer Research Campaign Technology Limited
    Inventors: Gerard Gallacher, Geoffrey W. Mellor, Yee-Ping Ho
  • Patent number: 5264609
    Abstract: Compounds of formula I ##STR1## in which Ar is aryl and R.sup.1 and R.sup.2 are alkyl, are obtained by a process in which a compound of formula II ##STR2## where Z is a disubstituted amino group, a) is reacted with an alcohol, R.sup.2 OH, preferably under acidic conditions, to give a compound of formula III ##STR3## which is then dealkanolated, or b) is hydrolysed under acid conditions, to give a compound of formula IV ##STR4## which then alkylated. The compounds of formula I have fungicidal activity, as do many of the compounds of formula II, III and IV.
    Type: Grant
    Filed: May 14, 1992
    Date of Patent: November 23, 1993
    Assignee: Schering Agrochemicals Limited
    Inventors: Clive L. Cornell, Ian C. Richards
  • Patent number: 5260482
    Abstract: A process for obtaining a substantially pure enantiomer of an aryl-substituted aliphatic carboxylic acid is described. The process combines an aryl substituted aliphatic carboxylic acid, a base and water in an inert solvent to make a hydrated salt of the said acid. The process leads to enhanced yield of an enantiomerically enriched hydrated salt of the carboxylic acid.
    Type: Grant
    Filed: October 14, 1992
    Date of Patent: November 9, 1993
    Assignee: Ethyl Corporation
    Inventors: Patricia Pringle, William T. Murray, Douglas K. Thompson, Azfar A. Choudhury, Deepak R. Patil
  • Patent number: 5256816
    Abstract: A process for obtaining a substantially pure enantiomer of an aryl-substituted aliphatic carboxylic acid is described. In this process, the aryl-substituted aliphatic carboxylic acid is reacted with an inorganic base in the presence of an organic base to substantially enrich the precipitate in one of the enantiomers and an improved yield. Substantially pure, enantiomeric salt is separated, leaving a mother liquor comprising the solvent and aryl-substituted aliphatic carboxylic acid enriched in the other enantiomer.
    Type: Grant
    Filed: October 14, 1992
    Date of Patent: October 26, 1993
    Assignee: Ethyl Corporation
    Inventors: William T. Murray, Robert E. Young, Azfar A. Choudhury, Deepak R. Patil
  • Patent number: 5256826
    Abstract: A process for the preparation of aromatic carbonyl or sulfonyl compounds with a diaryl ether structure by reacting phenols with halogenated carbonyl- or sulfonylaromatic compounds in a dipolar aprotic solvent is carried out in the presence of catalytic amounts of alkali metal nitrite or an aromatic nitro, nitroso, azo, azoxy or hydrazo compound.
    Type: Grant
    Filed: August 31, 1992
    Date of Patent: October 26, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Erwin Hahn, Heinrich J. Eilingsfeld, Helmut Reichelt, Alexander Aumueller, Bernd Hupfeld
  • Patent number: 5254718
    Abstract: This invention concerns esters of unsymmetrically 2-substituted glycolic acid dimers, a process for their preparation and their use in the preparation of unsymmetrically 3,6-substituted 1,4-dioxane-2,5-diones.
    Type: Grant
    Filed: February 27, 1991
    Date of Patent: October 19, 1993
    Assignee: E. I. Du Pont de Nemours & Company
    Inventors: David L. Anton, Charles E. Nakamura
  • Patent number: 5254727
    Abstract: Two acyclic tricarboxylic acid compounds have been isolated from the fermentation of Sporormiella intermedia. The compounds and their derivatives may be used as antifungal agents, cholesterol lowering agents and as anticancer agents.
    Type: Grant
    Filed: October 19, 1992
    Date of Patent: October 19, 1993
    Assignee: Merck & Co., Inc.
    Inventors: Claude Dufresne, E. Tracy T. Jones, Leslie A. Ferrell
  • Patent number: 5248813
    Abstract: A process for obtaining a substantially pure enantiomer of an aryl-substituted aliphatic carboxylic acid is described. The process utilizes first an enantiomerically enriched mixture the of aryl-substituted aliphatic carboxylic acid obtained from kinetic resolution, diastereomeric crystallization or asymmetric synthesis processes. This enriched mixture is reacted with a base producing a salt that has the following properties:(1) has at least one eutectic point;(2) a composition that is not at the eutectic point; and(3) a eutectic composition that is closer to the racemic composition than is the eutectic composition of said aryl-substituted carboxylic acid.Substantially pure, enantiomeric salt is separated, leaving a mother liquor comprising the solvent and aryl-substituted aliphatic carboxylic acid enriched in the other enantiomer.
    Type: Grant
    Filed: October 14, 1992
    Date of Patent: September 28, 1993
    Assignee: Ethyl Corporation
    Inventors: Thanikavelu Manimaran, G. Patrick Stahly, R. Carl Herndon, Jr.
  • Patent number: 5246966
    Abstract: The new substituted alkenoic acid derivatives can be prepared by reacting the appropriate aldehyde with a phosphonium compound. The compounds have leukotriene antagonistic properties and can be incorporated into pharmaceutical compositions.
    Type: Grant
    Filed: December 30, 1991
    Date of Patent: September 21, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinrich Meier, John E. B. Ransohoff, Trevor S. Abram, Peter Norman, Tudhope Stephen R., Phillip J. Gardiner, Nigel J. Cuthbert, Hilary P. Francis
  • Patent number: 5243066
    Abstract: Alkyl 2-aryl-2,2-dialkoxyacetates are prepared by electrochemical oxidation of alkyl 2-arylacetates and are used to prepare arylglyoxylic esters.
    Type: Grant
    Filed: July 2, 1992
    Date of Patent: September 7, 1993
    Assignee: BASF Aktiengesellschaft
    Inventor: Dieter Hermeling
  • Patent number: 5243070
    Abstract: The enantiomers of 2,2-dimethylcyclopropanecarboxylic acid are separated by esterification with the hydroxy group of optically active mandelic acid methyl ester, crystallization of the diastereomeric esters and subsequent hydrolysis of the diastereomeric esters.
    Type: Grant
    Filed: June 6, 1991
    Date of Patent: September 7, 1993
    Assignee: Lonza Ltd.
    Inventor: Thomas Meul
  • Patent number: 5232633
    Abstract: Carbonated isethionate surfactants, compositions containing them and methods for their preparation are disclosed.
    Type: Grant
    Filed: June 19, 1992
    Date of Patent: August 3, 1993
    Assignee: Lever Brothers
    Inventors: Leonora M. Ilardi, Stephen Madison, Deanne Oppermann
  • Patent number: 5231113
    Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## where the R groups are independently hydrogen, or lower alkyl; A is --C(O)O--, --OC(O)--, --C(O)S--, or --SC(O)--; n is 0-5; and Z is H, --COB where B is --OH or a pharmaceutically acceptable salt, or B is --OR.sub.1 where R.sub.1 is an ester-forming group, or B is --N(R).sub.2 where R is hydrogen or lower alkyl, or Z is --OE where E is hydrogen or an ether-forming group or --COR.sub.2 where R.sub.2 is hydrogen, lower alkyl, phenyl or lower alkyl phenyl, or Z is --CHO or an acetal derivative thereof, or Z is --COR.sub.3 where R.sub.3 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4 and the sum of n and m does not exceed 4.
    Type: Grant
    Filed: June 4, 1992
    Date of Patent: July 27, 1993
    Assignee: Allergan, Inc.
    Inventors: Roshantha A. S. Chandraratna, Robert J. Weinkam
  • Patent number: 5229375
    Abstract: Phosphine oxide-terminated allene-ene-yne compounds are disclosed that possess DNA-cleaving, antimicobial and tumor growth-inhibiting properties. Methods of making and using those compounds are also disclosed.
    Type: Grant
    Filed: August 1, 1990
    Date of Patent: July 20, 1993
    Assignee: Scripps Clinic and Research Foundation
    Inventors: Peter E. Maligres, Kyriacos C. Nicolaou
  • Patent number: 5221762
    Abstract: E-oxime ethers of phenylglyoxylic esters of the formula I ##STR1## where X and Y are each halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or trifluoromethyl;m is an integer from 0 to 4;n is an integer from 0 to 3;are prepared.
    Type: Grant
    Filed: December 13, 1991
    Date of Patent: June 22, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Horst Wingert, Bernd Wolf, Remy Benoit, Hubert Sauter, Michael Hepp, Wassilios Grammenos, Thomas Kuekenhoehner
  • Patent number: 5218138
    Abstract: This invention is directed to a method for stereoselectively preparing a syn-dihydroxylated compound comprising reacting a 3-hydroxyket-1-one and a sterically hindered dialkylated borane to form a complex at about -50.degree. C. to about 0.degree. C., and reducing the complex with hydride at about -25.degree. C. to about 50.degree. C.
    Type: Grant
    Filed: September 2, 1992
    Date of Patent: June 8, 1993
    Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.
    Inventors: Fang-Ting Chiu, William L. Studt
  • Patent number: 5216024
    Abstract: The present invention discloses new and useful compounds including methyl p-hydroxyphenyllactate, its analogues, chemical derivatives and chemically related compounds and their use as antitumor agents, as inhibitors of proliferative cell growth and as prophylactic agents to inhibit and prevent cancer and non-malignant cell growth.
    Type: Grant
    Filed: July 15, 1988
    Date of Patent: June 1, 1993
    Assignee: Baylor College of Medicine
    Inventors: Barry M. Markaverich, James H. Clark, Rebecca Gregory, Mary Alejandro, Brian S. Middleditch, Gregory A. Johnson, Rajender S. Varma
  • Patent number: 5214161
    Abstract: A process for the preparation of a polycyclic dye of the Formula (1): ##STR1## by reacting a ketal ester of the Formula (2): ##STR2## with a benzofuranone of the Formula (3): ##STR3## wherein: Ring A is unsubstituted or is substituted by from one to three groups:Ring B is unsubstituted, apart from the nitro group, or is substituted by one or two additional groups;each R is independently alkyl.The polycyclic dyes described are useful for the coloration of synthetic textile materials especially polyesters.
    Type: Grant
    Filed: June 15, 1992
    Date of Patent: May 25, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventor: David J. Milner
  • Patent number: 5207946
    Abstract: 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## (A) and (B) each represents a group selected from the group consisting of ##STR3## and * indicates an optically active center.
    Type: Grant
    Filed: July 25, 1990
    Date of Patent: May 4, 1993
    Assignee: Showa Shell Sekiyu K.K.
    Inventors: Koichi Numazawa, Noriko Yamakawa, Yoshiichi Suzuki, Ichiro Kawamura
  • Patent number: 5206389
    Abstract: These acrylates are those of formulae: ##STR1## where R=C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.12 cycloalkyl, aryl, arylalkyl or alkylaryl; Y=C.sub.1 -C.sub.12 alkyl, C.sub.6 -C.sub.12 aryl, heterocyclic radical whose ring contains from 5 to 10 members and whose heteroatom is chosen from N, O and S, an alkylaryl in which the alkyl part contains from 1 to 4 carbon atoms, Y not being able to denote 1,4-phenylene when R denotes methyl; and Z=hydrocarbon radical containing at least 2 C forming with O and the 2 adjacent Cs a ring containing from 4 to 8 members.To prepare them, an acrylate of formula CH.sub.2 .dbd.CH--COOR is reacted with a dialdehyde OHC--Y--CHO in the presence of an effective quantity of at least one functionalisation catalyst.The invention also relates to the preparation of new polymers and copolymers from the said acrylates.
    Type: Grant
    Filed: June 27, 1991
    Date of Patent: April 27, 1993
    Assignee: Atochem
    Inventors: Marie-Christine Berthe, Paul Caubere, Yves Fort
  • Patent number: 5204454
    Abstract: Prepolymer polyols containing mesogenic moieties useful as reactants for the preparation of resinous materials are disclosed. Synthesized by condensing a polyether polyol with bifunctional mesogenic diacids, or diesters, the compounds of the invention are characterized by their reasonably low melt temperature which renders them suitable as additive materials in polymeric molding compositions and as precursors for the preparation of resinous materials.The liquid crystalline properties of the prepolymers of the invention were found to depend on the type and molecular weight of the glycols and on the molar ratio between the glycols and the mesogenic reactant.
    Type: Grant
    Filed: July 19, 1991
    Date of Patent: April 20, 1993
    Assignee: Miles Inc.
    Inventors: Randall A. Rodenhouse, Dittmar K. Nerger, Douglas A. Wicks
  • Patent number: 5202457
    Abstract: The invention relates to optically active alkyl 3-aryl-3-hydroxypropionates represented by the general formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are hydrogen, hydroxyl, alkoxy of 1-4 carbon atoms, benzyloxy, flurorine, chlorine or bromine and R.sup.6 is alkyl, and a method for producing the above compounds.
    Type: Grant
    Filed: July 28, 1992
    Date of Patent: April 13, 1993
    Assignee: Chisso Corporation
    Inventors: Kazutoshi Miyazawa, Naoyuki Yoshida
  • Patent number: 5198569
    Abstract: The asymmetric hydrogenation of aliphatic .alpha.-keto esters in the presence of rhodium catalysts which contain as chiral ligand a diphosphine of formula IV(R.sub.3).sub.2 P--Q--P(R.sub.3)hd 2 (IV)wherein R.sub.3 is phenyl, C.sub.1 -C.sub.6 alkylphenyl or C.sub.1 -C.sub.6 alkoxyphenyl, and Q is [2,2,1]-bicyloheptan-1,2-ylene or [2,2,1]-bicyclohept-4,5-en-1,2-ylene, gives the corresponding (R)- or(S)-.alpha.-hydroxycarboxylic acid esters in high rates of chemical conversion and in high enantiomer excesses.
    Type: Grant
    Filed: September 11, 1991
    Date of Patent: March 30, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans-Ulrich Blaser, Ulrich Pittelkow, Felix Spindler
  • Patent number: 5198568
    Abstract: This invention relates to novel compositions of matter which are esters with enhanced water solubility, for use in aqueous enzymatic resolution reactions of racemic mixtures of these esters for producing the separate chiral isomers of the racemic mixture. The invention also relates to novel methods for preparing these esters. The importance of the production of the separate chiral isomers of the racemic mixtures resides in the isolation of the isomers which frequently have different biological activities. Of particular significance regarding the water soluble esters of this invention is that they are derivatized with groups which enhance their aqueous solubility and their reactivity with enzymatic resolving methods which are mediated in an aqueous environment.
    Type: Grant
    Filed: September 9, 1991
    Date of Patent: March 30, 1993
    Assignee: Sepracor, Inc.
    Inventors: Charles M. Zepp, Stephen A. Wald, David R. Dodds
  • Patent number: 5194668
    Abstract: Carboxylic acid esters and formamide are efficiently obtained by reacting carboxylic acid amides and formic acid esters, or by reacting carboxylic acid amides, alcohols and carbon monoxide in the presence of a dehydrated condensate of carboxylic acid amide with an alkali metal hydroxide or an alkaline earth metal hydroxide catalyst.
    Type: Grant
    Filed: June 8, 1990
    Date of Patent: March 16, 1993
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Hideo Ikarashi, Hirofumi Higuchi, Koichi Kida
  • Patent number: 5189063
    Abstract: Pesticidal substituted acrylic esters of the formula ##STR1## in which R.sup.1 represents alkyl, or represents unsubstituted or substituted aralkyl,R.sup.2 represents dialkylamino, or represents a radical --Z--R.sup.3,R.sup.3 represents alkyl, or represents unsubstituted or substituted aralkyl,Z represents oxygen or sulphur,A represents ##STR2## where n represents a number from 0 to 6,R.sup.4 and R.sup.5 in each case independently of one another represent alkyl, or together represent an alkylene chain having 2 to 7 carbon atoms, andR.sup.6 represents alkyl, or represents a radical ##STR3## where R.sup.7 represents alkyl, alkoxy or dialkylamino,B represents the group CH--R.sup.8 or, whereR.sup.9 represents unsubstituted or substituted alkyl, alkenyl, alkynyl, aralkyl, aryl or hetaryl, andR and Q independently of one another represent hydrogen, alkyl, halogenoalkyl or alkoxy.
    Type: Grant
    Filed: August 17, 1990
    Date of Patent: February 23, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Alexander Klausener, Herbert Gayer, Wolfgang Kramer, Dieter Berg, Wilhelm Brandes, Gerd Hanssler, Ulrike Wachendorff-Neumann
  • Patent number: 5167863
    Abstract: There are disclosed an optically active compound represented by the general formula: ##STR1## wherein n, R.sub.1, R.sub.2, R.sub.3, R.sub.4, Q.sub.1, Q.sub.2, Q.sub.3, and M are defined as in the detailed explanation, and *-marked carbon atoms are each an asymmetric carbon atom; a liquid crystal composition comprising at least one optically active compound of said general formula and a liquid crystal optical modulator using the composition thereof.
    Type: Grant
    Filed: July 16, 1990
    Date of Patent: December 1, 1992
    Assignees: Hitachi, Ltd., Takeda Chemical Industries, Ltd.
    Inventors: Teruo Kitamura, Katsumi Kondo, Akio Mukoh, Koichi Matsumura, Mitsuru Kawada, Yoshihiro Sugihara
  • Patent number: 5166377
    Abstract: The invention concerns novel 4-phenyl-1,3-dioxan-5-ylalkenoic acid derivatives of the formula I having cis relative stereochemistry at positions 4 and 5 of the dioxane ring and wherein Ra and Rb are variously hydrogen, alkyl, halogenoalkyl, alkenyl, and optionally substituted aryl or arylalkyl, Rc is hydroxy, alkoxy or alkanesulphonamido, n is 1 or 2, A is ethylene or vinylene, Y is (2-5C)polymethylene optionally substituted by alkyl, and benzene ring B is optionally substituted phenyl, or, when Rc is hydroxy, a salt thereof. The acid derivatives antagonize one or more of the actions of thromboxane A.sub.2 (TXA.sub.2) and are expected to be of value in those disease conditions in which TXA.sub.2 is involved. The invention also provides pharmaceutical compositions containing an acid derivative of formula I, and processes for their chemical production.
    Type: Grant
    Filed: February 9, 1988
    Date of Patent: November 24, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Andrew G. Brewster, Peter W. R. Caulkett