Oxy, Not Bonded Directly To A Ring, In Same Side Chain As Ester Function Patents (Class 560/60)
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Patent number: 5360819Abstract: 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: GrantFiled: March 11, 1985Date of Patent: November 1, 1994Assignee: Northeastern UniversityInventor: Roger W. Giese
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Patent number: 5352701Abstract: 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: GrantFiled: May 5, 1993Date of Patent: October 4, 1994Assignee: Schering AktiengesellschaftInventors: Josef Heindl, Werner Skuballa, Bernd Buchmann, Wolfgang Frohlich, Roland Ekerdt, Claudia Giesen
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Patent number: 5350873Abstract: 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: GrantFiled: August 13, 1992Date of Patent: September 27, 1994Assignee: BASF AktiengesellschaftInventors: Volker Bach, Wolfgang Brox, Karl-Heinz Etzbach, Axel Paul, Karl Siemensmeyer
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Patent number: 5347039Abstract: 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: GrantFiled: August 11, 1993Date of Patent: September 13, 1994Assignee: Rhone-Poulenc Rorer S.A.Inventors: Patrick Leon, Xavier Radisson, Viviane Massonneau
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Patent number: 5334748Abstract: 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: GrantFiled: September 9, 1988Date of Patent: August 2, 1994Assignee: Imperial Chemical Industries PLCInventors: 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
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Patent number: 5334607Abstract: 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: GrantFiled: May 28, 1992Date of Patent: August 2, 1994Assignee: BASF AktiengesellschaftInventors: Hubert Sauter, Gisela Lorenz, Gerd Steiner, Bernd Janssen, Timm Anke, Wolfgang Steglich
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Patent number: 5332857Abstract: 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: GrantFiled: July 6, 1992Date of Patent: July 26, 1994Assignee: Pfizer Inc.Inventors: Peter A. McCarthy, Frederick J. Walker
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Patent number: 5330739Abstract: 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: GrantFiled: December 4, 1992Date of Patent: July 19, 1994Assignee: Sterling Winthrop Inc.Inventor: Carl R. Illig
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Patent number: 5318994Abstract: 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: GrantFiled: November 3, 1992Date of Patent: June 7, 1994Assignee: Adir et CompagnieInventors: Jean Andrieux, Raymond Houssin, Said Yous, Beatrice Guardiola, Daniel Lesieur
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Patent number: 5315025Abstract: 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: GrantFiled: March 29, 1991Date of Patent: May 24, 1994Assignee: Imperial Chemical Industries PLCInventors: Michael J. Bushell, Kevin Beautement, John M. Clough, Vivienne M. Anthony, Paul deFraine, Christopher R. Godfrey
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Patent number: 5312950Abstract: 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: GrantFiled: August 31, 1993Date of Patent: May 17, 1994Assignee: Eastman Kodak CompanyInventor: Neil W. Boaz
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Patent number: 5310746Abstract: 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: GrantFiled: November 24, 1992Date of Patent: May 10, 1994Assignee: Roussel UclafInventors: Jean-Louis Brayer, Jean-Pierre Demoute, Yannick Le Stanc, Nicole Reinier
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Patent number: 5294724Abstract: 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: GrantFiled: September 6, 1990Date of Patent: March 15, 1994Assignee: Hoechst AktiengesellschaftInventors: Heiner Jendralla, Gunther Wess, Kurt Kesseler, Gerhard Beck
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Patent number: 5294639Abstract: 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: GrantFiled: September 4, 1991Date of Patent: March 15, 1994Assignee: BASF AktiengesellschaftInventors: Reinhard Kirstgen, Albrecht Harreus, Uwe Kardorff, Thomas Kuekenhoehner, Harald Rang, Gisela Lorenz, Eberhard Ammermann, Christoph Kuenast
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Patent number: 5294731Abstract: 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: GrantFiled: March 23, 1993Date of Patent: March 15, 1994Assignee: BASF AktiengesellschaftInventors: Joachim Paust, Wolfgang Siegel
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Patent number: 5292946Abstract: 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: GrantFiled: March 23, 1992Date of Patent: March 8, 1994Assignee: Merck & Co., Inc.Inventors: Pamela M. Simpson, David M. Tschaen, Thomas R. Verhoeven
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Patent number: 5290950Abstract: 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: GrantFiled: November 27, 1991Date of Patent: March 1, 1994Assignee: Wayne State UniversityInventors: Morton Raban, David T. Durocher
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Patent number: 5286895Abstract: 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: GrantFiled: December 7, 1992Date of Patent: February 15, 1994Assignee: Merck & Co., Inc.Inventors: Guy H. Harris, Henry Joshua, Deborah L. Zink
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Patent number: 5278338Abstract: 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: GrantFiled: November 4, 1992Date of Patent: January 11, 1994Assignee: Ethyl CorporationInventor: Rhonda L. Trace
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Patent number: 5278337Abstract: 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: GrantFiled: October 14, 1992Date of Patent: January 11, 1994Assignee: Ethyl CorporationInventors: Thanikavelu Manimaran, G. Patrick Stahly, R. Carl Herndon, Jr.
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Patent number: 5274168Abstract: 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: GrantFiled: December 4, 1992Date of Patent: December 28, 1993Assignee: Sumitomo Chemical Company, LimitedInventors: Takayuki Higashii, Masayoshi Minai
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Patent number: 5274155Abstract: 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: GrantFiled: December 7, 1992Date of Patent: December 28, 1993Assignee: E. R. Squibb & Sons, Inc.Inventors: John K. Thottathil, David Kronenthal
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Patent number: 5266720Type: GrantFiled: July 8, 1991Date of Patent: November 30, 1993Assignee: Cancer Research Campaign Technology LimitedInventors: Gerard Gallacher, Geoffrey W. Mellor, Yee-Ping Ho
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Patent number: 5264609Abstract: 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: GrantFiled: May 14, 1992Date of Patent: November 23, 1993Assignee: Schering Agrochemicals LimitedInventors: Clive L. Cornell, Ian C. Richards
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Patent number: 5260482Abstract: 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: GrantFiled: October 14, 1992Date of Patent: November 9, 1993Assignee: Ethyl CorporationInventors: Patricia Pringle, William T. Murray, Douglas K. Thompson, Azfar A. Choudhury, Deepak R. Patil
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Patent number: 5256816Abstract: 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: GrantFiled: October 14, 1992Date of Patent: October 26, 1993Assignee: Ethyl CorporationInventors: William T. Murray, Robert E. Young, Azfar A. Choudhury, Deepak R. Patil
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Patent number: 5256826Abstract: 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: GrantFiled: August 31, 1992Date of Patent: October 26, 1993Assignee: BASF AktiengesellschaftInventors: Erwin Hahn, Heinrich J. Eilingsfeld, Helmut Reichelt, Alexander Aumueller, Bernd Hupfeld
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Patent number: 5254718Abstract: 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: GrantFiled: February 27, 1991Date of Patent: October 19, 1993Assignee: E. I. Du Pont de Nemours & CompanyInventors: David L. Anton, Charles E. Nakamura
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Patent number: 5254727Abstract: 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: GrantFiled: October 19, 1992Date of Patent: October 19, 1993Assignee: Merck & Co., Inc.Inventors: Claude Dufresne, E. Tracy T. Jones, Leslie A. Ferrell
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Patent number: 5248813Abstract: 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: GrantFiled: October 14, 1992Date of Patent: September 28, 1993Assignee: Ethyl CorporationInventors: Thanikavelu Manimaran, G. Patrick Stahly, R. Carl Herndon, Jr.
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Patent number: 5246966Abstract: 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: GrantFiled: December 30, 1991Date of Patent: September 21, 1993Assignee: Bayer AktiengesellschaftInventors: Heinrich Meier, John E. B. Ransohoff, Trevor S. Abram, Peter Norman, Tudhope Stephen R., Phillip J. Gardiner, Nigel J. Cuthbert, Hilary P. Francis
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Patent number: 5243066Abstract: Alkyl 2-aryl-2,2-dialkoxyacetates are prepared by electrochemical oxidation of alkyl 2-arylacetates and are used to prepare arylglyoxylic esters.Type: GrantFiled: July 2, 1992Date of Patent: September 7, 1993Assignee: BASF AktiengesellschaftInventor: Dieter Hermeling
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Patent number: 5243070Abstract: 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: GrantFiled: June 6, 1991Date of Patent: September 7, 1993Assignee: Lonza Ltd.Inventor: Thomas Meul
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Patent number: 5232633Abstract: Carbonated isethionate surfactants, compositions containing them and methods for their preparation are disclosed.Type: GrantFiled: June 19, 1992Date of Patent: August 3, 1993Assignee: Lever BrothersInventors: Leonora M. Ilardi, Stephen Madison, Deanne Oppermann
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Patent number: 5231113Abstract: 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: GrantFiled: June 4, 1992Date of Patent: July 27, 1993Assignee: Allergan, Inc.Inventors: Roshantha A. S. Chandraratna, Robert J. Weinkam
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Patent number: 5229375Abstract: 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: GrantFiled: August 1, 1990Date of Patent: July 20, 1993Assignee: Scripps Clinic and Research FoundationInventors: Peter E. Maligres, Kyriacos C. Nicolaou
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Patent number: 5221762Abstract: 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: GrantFiled: December 13, 1991Date of Patent: June 22, 1993Assignee: BASF AktiengesellschaftInventors: Horst Wingert, Bernd Wolf, Remy Benoit, Hubert Sauter, Michael Hepp, Wassilios Grammenos, Thomas Kuekenhoehner
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Patent number: 5218138Abstract: 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: GrantFiled: September 2, 1992Date of Patent: June 8, 1993Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.Inventors: Fang-Ting Chiu, William L. Studt
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Patent number: 5216024Abstract: 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: GrantFiled: July 15, 1988Date of Patent: June 1, 1993Assignee: Baylor College of MedicineInventors: Barry M. Markaverich, James H. Clark, Rebecca Gregory, Mary Alejandro, Brian S. Middleditch, Gregory A. Johnson, Rajender S. Varma
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Patent number: 5214161Abstract: 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: GrantFiled: June 15, 1992Date of Patent: May 25, 1993Assignee: Imperial Chemical Industries PLCInventor: David J. Milner
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Patent number: 5207946Abstract: 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: GrantFiled: July 25, 1990Date of Patent: May 4, 1993Assignee: Showa Shell Sekiyu K.K.Inventors: Koichi Numazawa, Noriko Yamakawa, Yoshiichi Suzuki, Ichiro Kawamura
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Patent number: 5206389Abstract: 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: GrantFiled: June 27, 1991Date of Patent: April 27, 1993Assignee: AtochemInventors: Marie-Christine Berthe, Paul Caubere, Yves Fort
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Patent number: 5204454Abstract: 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: GrantFiled: July 19, 1991Date of Patent: April 20, 1993Assignee: Miles Inc.Inventors: Randall A. Rodenhouse, Dittmar K. Nerger, Douglas A. Wicks
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Patent number: 5202457Abstract: 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: GrantFiled: July 28, 1992Date of Patent: April 13, 1993Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Naoyuki Yoshida
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Patent number: 5198569Abstract: 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: GrantFiled: September 11, 1991Date of Patent: March 30, 1993Assignee: Ciba-Geigy CorporationInventors: Hans-Ulrich Blaser, Ulrich Pittelkow, Felix Spindler
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Patent number: 5198568Abstract: 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: GrantFiled: September 9, 1991Date of Patent: March 30, 1993Assignee: Sepracor, Inc.Inventors: Charles M. Zepp, Stephen A. Wald, David R. Dodds
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Patent number: 5194668Abstract: 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: GrantFiled: June 8, 1990Date of Patent: March 16, 1993Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Hideo Ikarashi, Hirofumi Higuchi, Koichi Kida
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Patent number: 5189063Abstract: 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: GrantFiled: August 17, 1990Date of Patent: February 23, 1993Assignee: Bayer AktiengesellschaftInventors: Alexander Klausener, Herbert Gayer, Wolfgang Kramer, Dieter Berg, Wilhelm Brandes, Gerd Hanssler, Ulrike Wachendorff-Neumann
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Patent number: 5167863Abstract: 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: GrantFiled: July 16, 1990Date of Patent: December 1, 1992Assignees: Hitachi, Ltd., Takeda Chemical Industries, Ltd.Inventors: Teruo Kitamura, Katsumi Kondo, Akio Mukoh, Koichi Matsumura, Mitsuru Kawada, Yoshihiro Sugihara
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Patent number: 5166377Abstract: 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: GrantFiled: February 9, 1988Date of Patent: November 24, 1992Assignee: Imperial Chemical Industries PLCInventors: Andrew G. Brewster, Peter W. R. Caulkett