Processes Patents (Class 568/309)
  • Patent number: 6300376
    Abstract: Indane dimer compounds and their pharmaceutical use particularly to achieve smooth muscle relaxing activity and/or mast cell stabilizing activity and/or anti-inflammatory activity are described.
    Type: Grant
    Filed: June 8, 1998
    Date of Patent: October 9, 2001
    Assignee: Venantius Limited
    Inventors: John Walsh, Neil Frankish, Helen Sheridan, Ronan Farrell, William Byrne
  • Patent number: 6281249
    Abstract: This invention provides a novel class of vitamin D compounds, namely, 13-ethyl and 13-vinyl-18,19-dinor-vitamin D derivatives, as well as a general method for their chemical synthesis. The compounds have the formula: where Y1 and Y2, which may be the same or different, are each selected from the group consisting of hydrogen and a hydroxy-protecting group, R6 is selected from the group consisting of an ethyl or vinyl radical, and where the group R represents any of the typical side chains known for vitamin D type compounds. These 18-substituted compounds are characterized by minimal intestinal calcium transport activity and minimal bone calcium mobilization activity resulting in novel therapeutic agents for the treatment of secondary hyperparathyroidism.
    Type: Grant
    Filed: July 15, 1999
    Date of Patent: August 28, 2001
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Zu Y. Cai
  • Patent number: 6274770
    Abstract: There is disclosed a process for the preparation of a compound of general formula (I), wherein Y and Z each independently represent a fluorine atom or a hydroxy group, and a, b, c and d independently represent 0, 1, 2 or 3 provided that the sum of a, b, c, and d is 1, 2, 3 or 4; the process comprising treating a compound of general formula (II), wherein a, b, c, and d are as described above and L1 and L2 each independently represent an active group provided that either Y and L1 are different or Z and L2 are different, with a fluorinating system in the presence of oxygen. A preferred compound of general formula (I) is 4,4′-difluorobenzophenone which may be prepared from 4,4′-dinitrophenylmethane using tetramethylammonium fluoride.
    Type: Grant
    Filed: September 13, 1999
    Date of Patent: August 14, 2001
    Assignee: Victrex Manufacturing Limited
    Inventors: James Hanley Clark, David Adams
  • Patent number: 6271421
    Abstract: A process for selectively debrominating polybromoalkyl aryl ketones and polybromoalkyl heteroaryl ketones is disclosed. The process comprises contacting an alpha-polybrominated ketone with an alkali metal sulfite in the presence of a C2-C6 alkylcarboxylic acid to obtain a selectively mono-debrominated product.
    Type: Grant
    Filed: November 12, 1999
    Date of Patent: August 7, 2001
    Assignee: Merck & Co., Inc.
    Inventor: Anthony O. King
  • Publication number: 20010005767
    Abstract: Acetophenones which are di- or polysubstituted by fluoroalkyl groups on the aromatic ring are prepared in a particularly advantageous manner from the corresponding fluoroalkylanilines and acetaldoxime by preparing a corresponding diazonium salt mixture from the fluoroalkylaniline, reacting this mixture with acetaldoxime in the presence of at least one copper and/or palladium compound, without adding buffer salts or a reducing agent, carrying out the reaction with acetaldoxime at 5 to 50° C. and in the presence of halide ions and at least one strong acid that is not a hydrohalic acid, and finally heating the mixture to a temperature in the range 70 to 160° C.
    Type: Application
    Filed: December 8, 2000
    Publication date: June 28, 2001
    Inventors: Wulf Kuhnle, Thomas Hopfner
  • Patent number: 6251833
    Abstract: The present invention relates to novel 2-aryl-3-hydroxy-&Dgr;2-cyclopentene-1-one derivatives of the formula (I) in which A, B, D1, D2, G, W, X, Y and Z are each as defined in the description, to processes for their preparation and to their use as herbicides and pesticides.
    Type: Grant
    Filed: August 31, 1999
    Date of Patent: June 26, 2001
    Inventors: Christoph Erdelen, Ulrike Wachendorff-Neumann, Reiner Fischer, Alan Graff, Norbert Mencke, Andreas Turberg
  • Patent number: 6245945
    Abstract: A process for the selective hydrolysis of acetals in the presence of phthalides comprises reacting a mixture (M) comprising a) a phthalide of the formula (I) where: R1,R2,R3 and R4: are independently hydrogen, C1-C4-alkyl or halogen, and b) an acetal or ketal of the formula (II) where: R5 and R6: are independently C1-C6-alkyl, C6-C10-aryl or together ethylene, and R7 and R8: are independently C1-C6-alkyl, or one radical is a hydrogen and the other is a phenyl radical where from 1 to 3 hydrogen atoms of the phenyl radical may be replaced by C1-C6-alkyl radicals or C1-C4-alkoxy radicals, or R7 and R8 are together C3-C6-alkanediyl, and a hydrogen atom may be replaced by a hydroxyl group, at from 10 to 200° C. in the presence of from 1 to 10 mol of water, based on the amount of acetal or ketal of the formula (II), to hydrolyze the acetal or ketal of the formula (II) to the corresponding aldehyde or ketone.
    Type: Grant
    Filed: August 25, 2000
    Date of Patent: June 12, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Andreas Weiper-Idelmann, Heinz Hannebaum, Hermann Pütter
  • Patent number: 6245944
    Abstract: A process for preparing a compound of the formula I where R1 and R2 are hydrogen or C1-C4-alkyl and R3 is C1-C10-alkyl, phenyl or C1-C4-alkyl-substituted phenyl, comprises reacting a compound II with a compound of the formula III where X is chlorine, bromine or iodine, in the presence of a Friedel-Crafts catalyst in one step to give a compound I.
    Type: Grant
    Filed: December 9, 1998
    Date of Patent: June 12, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Carsten Süling, Heike Gregorius, Walter Dobler, Roland Hingmann, Bernhard Rieger, Ulf Dietrich, Jürgen Matthäus Wagner, Hans-Joachim Müller
  • Patent number: 6239135
    Abstract: A series of aryl piperazine compounds of the formula: or the pharmaceutically acceptable salts thereof, are effective pharmaceuticals for the treatment of conditions related to or affected by the serotonin 1A receptor; the compounds are particularly effective antagonists at that receptor, and are particularly useful for alleviating the symptoms of nicotine and tobacco withdrawal.
    Type: Grant
    Filed: December 9, 1998
    Date of Patent: May 29, 2001
    Assignee: Eli Lilly and Company
    Inventors: Daniel Timothy Kohlman, Yao-Chang Xu
  • Patent number: 6218579
    Abstract: A process for preparing a compound of Formula (I); where Q completes an optionally substituted 5-or 6-member saturated carbocyclic ring and R is optionally substituted phenyl or optionally substituted C3-C6 cycloalkyl which comprises the rearrangement of a compound of Formula (II); where Q and R are as defined in relation to Formula (I) in a polar aprotic, dipolar aprotic or aromatic hydrocarbon solvent in the presence of a moderate base and an azole.
    Type: Grant
    Filed: April 18, 2000
    Date of Patent: April 17, 2001
    Assignee: Zeneca Limited
    Inventors: Robert Oliver Jones, Thomas William Bentley, Stephen Martin Brown
  • Patent number: 6211413
    Abstract: There is provided a process for the preparation of compounds of formula I wherein: X is H or F, Y is CF3 or F and R1 is hydrogen or C1-C2alkyl; in which process (1) a compound of formula II, wherein X and Y are as defined for formula I, is reacted with an organic or inorganic nitrite or nitrous acid; (2) the resulting diazonium compound of formula III is reacted with an aldoxime of formula V R1—CH═NOH   (V) wherein R1 is as defined for formula I, in presence of CuSO4; and (3) the resulting oxime of formula IV is hydrolyzed with aqueous acid to the compound of formula I.
    Type: Grant
    Filed: January 12, 1999
    Date of Patent: April 3, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Arthur Wegmann, Terry Lee Moore, Linhua Wang
  • Patent number: 6211412
    Abstract: Commercially feasible methods for synthesizing various epothilones precursors needed for the preparation of final epothilones are provided, including techniques for the synthesis of epothilone segment C using a stereoselective Noyori-type reduction, and the coupling of epothilone segments B and C using an aldol condensation reaction. The synthesis methods may be used to prepare naturally occurring segments as well as a large number of related analogs and homologs thereof. Final epothilones in accordance with the invention may also be of the naturally occurring variety (16-membered macrolides), while the homologs and analogs thereof are preferably up to 20-membered macrolides.
    Type: Grant
    Filed: March 29, 1999
    Date of Patent: April 3, 2001
    Assignee: The University of Kansas
    Inventors: Gunda I. Georg, Sajiv K. Nair, Emily Reiff, Ashok Rao Tunoori, John T. Henri
  • Patent number: 6191182
    Abstract: A novel process for the preparation of compounds of formula I by aminolysis of a p-halophenyl alkyl ketone of formula II with a cyclic amine of formula III in water at a temperature of at least 130° C., in which formulae X is a halogen atom and R1, R2 and R3 are as claimed in claim 1, as well as the novel compounds of formula I and their use for the preparation of photoinitiators for the photopolymerisation of ethylenically unsaturated compounds.
    Type: Grant
    Filed: June 10, 1999
    Date of Patent: February 20, 2001
    Assignee: Ciba Specialty Chemcials Corporation
    Inventors: Rinaldo Hüsler, Rudolf Schwabe, Reto Luisoli
  • Patent number: 6184417
    Abstract: Acetophenones which are substituted on the aromatic ring by fluoroalkyl are prepared in a particularly advantageous, environmentally friendly and effective manner from fluoroalkylanilines and acetaldoxime by preparing from a fluoroalkylaniline a corresponding diazonium salt solution, and reacting this with acetaldoxime in the presence of at least one copper compound, without adding any buffer salts or reducing agents, carrying out the reaction at from 20 to 50° C. and in the presence of halide ions and subsequently heating to a temperature in the range from 70 to 110° C.
    Type: Grant
    Filed: November 1, 1999
    Date of Patent: February 6, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wulf Kühnle, Albrecht Marhold, Guido Steffan
  • Patent number: 6169213
    Abstract: Process for the preparation of heteroaryl aldehydes or heteroaryl ketones by reaction with heteroarylmethanols with the aid of a mediator and an oxidant, wherein the mediator is selected from the group of the aliphatic, cycloaliphatic, heterocyclic or aromatic NO, and NOH containing compounds.
    Type: Grant
    Filed: January 5, 2000
    Date of Patent: January 2, 2001
    Assignee: Consortium f{umlaut over (u)}r elektrochemische Industrie GmbH
    Inventors: Elke Fritz-Langhals, Johannes Freudenreich, Norbert Hampp, Anton Candussio
  • Patent number: 6166260
    Abstract: The present invention relates to a tandem process of reduction and host-guest complexation using metal-hydride complexes to reduce chemical entities bearing carbonyl groups or their equivalents, and host-guest complexation to achieve improved optical resolution of the reduction product. In the complexation step, the reduction product is optically resolved via inclusion into the crystalline complex where it resides as guest and another complex component acts as host. Additional crystallization stages are performed if further improvements in the enantiomeric excess is desired.
    Type: Grant
    Filed: August 6, 1999
    Date of Patent: December 26, 2000
    Assignee: Zeeland Chemicals, Inc.
    Inventor: Glenn L. Heise
  • Patent number: 6147049
    Abstract: The present invention provides compounds of formula I: ##STR1## wherein R.sup.1 is hydrogen or methyl and R.sup.2 is alkyl. These compounds are useful as fixatives in fragrance compositions. Processes of making such compounds are also provided.
    Type: Grant
    Filed: December 13, 1999
    Date of Patent: November 14, 2000
    Assignee: Givaudan Roure (International) SA
    Inventors: Peter Gygax, Hans-Ulrich Gonzenbach
  • Patent number: 6096930
    Abstract: The present invention relates to novel cyclohexane-1-3-dione derivatives of formula (1) useful as herbicides and plant-growth regulants, ##STR1## wherein X is selected from the group consisting of hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkyl, nitro, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkylsulfinyl, C.sub.1 -C.sub.6 alkylsulfonyl, C.sub.1 -C.sub.6 sulfamoyl, and N, N-di(C.sub.1 -C.sub.6 alkyl)sulfamoyl group; (X)n represents the number of X substituents which may be substituted on benzene ring, wherein n is 1, 2 or 3. Also, cyclohexyl moiety, one of the substituents on benzofuran ring, is substituted at C-4, C-5, C-6 or C-7 position on benzene ring; R.sup.1 is selected from the group consisting of hydrogen and C.sub.1 -C.sub.6 alkyl group; R.sup.2 is selected from the group consisting of C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl and C.sub.2 -C.sub.6 alkynyl group; R.sup.3 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.
    Type: Grant
    Filed: May 12, 1998
    Date of Patent: August 1, 2000
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Eung Kul Ryu, Kyoung Mahn Kim, Jae Nyoung Kim, Jin Seog Kim
  • Patent number: 6046365
    Abstract: Unsubstituted or substituted cyclohexanones are advantageously prepared by hydrogenation of the corresponding phenols in the presence of a palladium-on-carbon catalyst at from 100 to 250.degree. C. and from 1 to 20 bar of hydrogen pressure if the catalyst is mixed with a base component and from 20 to 200% by weight of water (based on the base component) and this mixture is used in the hydrogenation. For identical batches, this gives virtually identical hydrogenation times and virtually equally good yields of cyclohexanones.
    Type: Grant
    Filed: June 29, 1998
    Date of Patent: April 4, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventor: Wolfgang Kiel
  • Patent number: 6037501
    Abstract: By subjecting an aromatic compound of the formula (I), which is an inexpensive raw material, to a vapor-phase intramolecular cyclodehydrogenation reaction, fluorenes of the formula (II) can be obtained industrially advantageously in a high yield. Fluorenes (II) are expected to be used as raw materials for heat-resistant epoxy resins, polycarbonates or polyesters. wherein R.sub.1 and R.sub.2 each represent a hydrogen atom, a methyl group or an ethyl group, or R.sub.1 and R.sub.2 represent .dbd.O at the same time; and R and R' each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.
    Type: Grant
    Filed: June 6, 1998
    Date of Patent: March 14, 2000
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Noboru Saito, Toshiya Iida, Isamu Maeda
  • Patent number: 6018080
    Abstract: The invention relates to a process for the production of microfluidized particles of atovaquone having improved bioavailability.
    Type: Grant
    Filed: November 19, 1997
    Date of Patent: January 25, 2000
    Assignee: Glaxo Wellcome Inc.
    Inventor: Alan Roy Dearn
  • Patent number: 5981754
    Abstract: The present invention relates to the compounds of formula (I) ##STR1## wherein Y is --CH-- or --N--; R.sub.1 is hydrogen, a halogen or a CF.sub.3, (C.sub.3 -C.sub.4)alkyl or (C.sub.1 -C.sub.4)alkoxy group; R.sub.2 is hydrogen, a halogen, a hydroxyl or a CF.sub.3, (C.sub.3 -C.sub.4)alkyl or (C.sub.1 -C.sub.4)alkoxy group; R.sub.3 and R.sub.4 are each hydrogen or a (C.sub.1 -C.sub.3)alkyl; and X is (a) a (C.sub.3 -C.sub.6)alkyl, a (C.sub.3 -C.sub.6)alkoxy, a (C.sub.3 -C.sub.7)carboxyalkyl, a (C.sub.1 -C.sub.4)-alkoxycarbonyl(C.sub.3 -C.sub.6)alkyl, a (C.sub.3 -C.sub.7)carboxyalkoxy or a (C.sub.1 -C.sub.4)alkoxycarbonyl(C.sub.3 -C.sub.6)alkoxy; (b) a radical selected from a (C.sub.3 -C.sub.7)cycloalkyl, (C.sub.3 -C.sub.7)cycloalkoxy, (C.sub.3 -C.sub.7)cycloalkylmethyl, (C.sub.3 -C.sub.7)cycloalkylamino and cyclohexenyl, it being possible for said radical to be substituted by a halogen, hydroxyl, (C.sub.1 -C.sub.4)alkoxy, carboxyl, (C.sub.1 -C.sub.4)alkoxycarbonyl, amino or mono- or di-(C.sub.1 -C.sub.
    Type: Grant
    Filed: February 24, 1998
    Date of Patent: November 9, 1999
    Assignee: Sanofi
    Inventors: Domenico Badone, Marco Baroni, Rosanna Cardamone, Jacqueline Fournier, Umberto Guzzi, Alessandra Ielmini
  • Patent number: 5969188
    Abstract: The present invention provides high purity trifluoromethylacetophenones of the general formula:F.sub.3 C--(C.sub.6 H.sub.4)-(C.dbd.O)--CH.sub.3wherein the position of the CF.sub.3 -- group on the aromatic ring may be in the 2-, 3-, or 4- position relative to the acetyl, --(C.dbd.O)--CH.sub.3, group, said trifluoromethylacetophenone being substantially free of other organic or inorganic materials, wherein said trifluoromethylacetophenones are produced by a novel high yield process.
    Type: Grant
    Filed: January 5, 1999
    Date of Patent: October 19, 1999
    Assignee: NIPA Hardwicke, Inc.
    Inventor: J. E. Hardwicke, III
  • Patent number: 5908770
    Abstract: A process for the preparation of a saturated butanone having a terminal substituted aryl group (I) by the selective reduction of an aryl-substituted .alpha.,.beta.-unsaturated butanone (II) is presented. The aryl moiety can be mono- or polysubstituted by one or more C.sub.1 -C.sub.6 alkoxy, methylenedioxy or hydroxyl radicals and R is a C.sub.1 -C.sub.6 radical. The .alpha.,.beta.-unsaturated butanone (II) is subjected to the action of the enzymes of a yeast or of a filamentous fungus to give a mixture of (I) and an alcohol (III). (I) and (III) are isolated and purified. (III) can be enzymatically oxidized to provide (I).
    Type: Grant
    Filed: July 14, 1997
    Date of Patent: June 1, 1999
    Assignee: Robertet S.A.
    Inventors: Daniel Joulain, Claudio Fuganti
  • Patent number: 5852200
    Abstract: Cross-coupling or addition reactions of organic compounds, including acid halides, allylic halides, and .alpha.,.beta.-unsaturated carbonyl containing compounds, with organozinc compounds may be readily and safely carried out in the presence of cuprous iodide. The use of this catalyst in the coupling reaction provides for the preparation of commercially useful products in the pharmaceutical, agrochemical and other industries.
    Type: Grant
    Filed: August 22, 1996
    Date of Patent: December 22, 1998
    Assignee: Rieke Metals, Inc.
    Inventor: Reuben D. Rieke
  • Patent number: 5840661
    Abstract: The present invention relates to novel 2-aryl-3-hydroxy-cyclopent-2-en-1-one derivatives of the formula (I) ##STR1## in which X represents halogen, nitro, cyano, alkyl, alkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkyl or halogenoalkoxy,Y represents hydrogen, halogen, nitro, cyano, alkyl, alkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkyl or halogenoalkoxy,Z represents halogen, nitro, cyano, alkyl, alkoxy or halogenoalkoxy andA, B, D.sup.1, D.sup.2, G and n have the meaning given in the description,several processes for their preparation and their use as compositions for controlling pests and as herbicides.
    Type: Grant
    Filed: December 31, 1996
    Date of Patent: November 24, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reiner Fischer, Jacques Dumas, Thomas Bretschneider, Christoph Erdelen, Ulrike Wachendorff-Neumann, Hans-Joachim Santel, Markus Dollinger, Andreas Turberg, Norbert Mencke
  • Patent number: 5811586
    Abstract: A process for manufacturing 1-(3-trifluoromethyl)phenyl-propan-2-one intermediate in the synthesis of the anorexic drug fenfluramine consists of reacting the diazonium salt of 3-trifluoromethylaniline with isopropenyl acetate in a polar solvent in the presence of a catalytic amount of a cuprous salt and, optionally, of a base and purifying the crude product through the bisulfite complex or distillation under vacuum.
    Type: Grant
    Filed: April 17, 1997
    Date of Patent: September 22, 1998
    Assignee: Alfa Chemicals Italiana S.P.A.
    Inventors: Vincenzo Cannata, Barbara Galbiati, Angelo Spreafico
  • Patent number: 5773635
    Abstract: A process for preparing polyenecarbonyl compounds having a high all-E content and their acetals or ketals by aldol condensation or Horner-Emmons reaction comprises carrying out the reaction, for the purposes of the preferred formation of a double bond of E configuration and in order to maintain the E configuration of the double bonds in the stating compounds as completely as possible, in the presence of oxygen or an oxygen-inert gas mixture or nitric oxide or a nitric oxide-inert gas mixture and/or in the presence of specific stable radicals and/or in the presence of quinones or quinone derivatives.
    Type: Grant
    Filed: July 6, 1995
    Date of Patent: June 30, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter Dobler, Wolfgang Krause, Joachim Paust, Otto Worz, Udo Rheude, Wolfram Burst, Gunter Dauwel, Armin Bertram, Bernhard Schulz, Gunter Wegner, Peter Munster, Hansgeorg Ernst, Arno Kochner, Heinz Etzrodt
  • Patent number: 5744071
    Abstract: The present invention provides processes for making alkynyl ketones and precursors thereof, using less expensive reagents and/or hydrocarbon solvents and/or higher temperatures.
    Type: Grant
    Filed: November 19, 1996
    Date of Patent: April 28, 1998
    Assignee: FMC Corporation
    Inventors: Philip Franklin Sims, Anne Pautard-Cooper
  • Patent number: 5723676
    Abstract: A process for producing benzophenone compounds is provided. Specifically, a process is provided for producing benzophenone compounds in which a diphenylmethane compound is reacted with manganese dioxide and a strong acid. The process yields the product benzophenone in high purity and good yield.
    Type: Grant
    Filed: July 1, 1996
    Date of Patent: March 3, 1998
    Assignee: AlliedSignal Inc.
    Inventors: Lee Alan DeWitt, Heng Su, Chempolil Thomas Mathew
  • Patent number: 5707559
    Abstract: Novel light producing 1,2-dioxetanes are described of the formula ##STR1## wherein ArOX is an aryl ring substituted with an X oxy group and A are passive organic groups which allow the 1,2-dioxetane to produce light when triggered by removing X. X is a chemically labile group which is removed by an activating agent. The 1,2-dioxetane compounds can be triggered to produce light at room temperatures.
    Type: Grant
    Filed: March 9, 1987
    Date of Patent: January 13, 1998
    Assignee: Tropix, Inc.
    Inventors: Arthur Paul Schaap, Irena Y. Bronstein
  • Patent number: 5659069
    Abstract: This invention discloses an improved method for the [2+2+2] cyclotrimerization reaction in aqueous solutions using a water soluble transition metal catalyst.
    Type: Grant
    Filed: March 20, 1996
    Date of Patent: August 19, 1997
    Assignee: NeXstar Pharmaceuticals, Inc.
    Inventors: Bruce Eaton, Matthew S. Sigman
  • Patent number: 5545769
    Abstract: A process is disclosed for the manufacture of product compounds of the formula HC(R.sup.1).sub.2 C(R.sup.1).sub.2 C(R.sup.2).sub.2 H wherein each R.sup.1 is independently selected from the group consisting of H, F, Cl, CN, R, OR, CO.sub.2 R, C(O)R, OC(O)R, R.sup.f, OR.sup.f, CO.sub.2 R.sup.f, C(O)R.sup.f and OC(O)R.sup.f where R is a hydrocarbyl group and R.sup.f is a C.sub.1 to C.sub.10 polyfluoroalkyl group, provided that at least one R.sup.1 is F, and wherein each R.sup.2 is independently selected from the group consisting of H, F, Cl, CN, R, OR, CO.sub.2 R, C(O)R, OC(O)R, R.sup.f, OR.sup.f, CO.sub.2 R.sup.f, C(O)R.sup.f, OC(O)R.sup.f and difunctional linkages where an R.sup.2 group on each of two adjacent carbon atoms together form a link selected from the group consisting of --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH(CH.sub.3)--, --CH.sub.2 CH(CH.sub.3)CH.sub.2 --, --C(O)OC(O)--, and norborndiyl.
    Type: Grant
    Filed: September 29, 1994
    Date of Patent: August 13, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Ralph T. Baker, Richard P. Beatty, William B. Farnham, Robert L. Wallace, Jr.
  • Patent number: 5536870
    Abstract: A process for preparing olefin compounds of the formula ##STR1## where A is aryl, substituted aryl, heteroaryl, substituted heteroaryl, benzyl, substituted benzyl, vinyl or substituted vinyl and R.sub.2, R.sub.3 and R.sub.4 are hydrogen, alkyl, cycloalkyl, alkyl-substituted cycloalkyl, aryl, substituted aryl, alkoxy, alkythio, heteroaryl, substituted heteroaryl, alkanoyl, aroyl, substituted aroyl, heteroarylcarbonyl, substituted heteroarylcarbonyl, trifluoromethyl or halo, which comprises reacting an organic halide of the formula A-X where X is chloro, bromo or iodo with a vinyl or substituted vinyl compound of the formula ##STR2## where R.sub.2, R.sub.3 and R.sub.
    Type: Grant
    Filed: February 17, 1995
    Date of Patent: July 16, 1996
    Assignee: Albemarle Corporation
    Inventor: Tse-Chong Wu
  • Patent number: 5481043
    Abstract: Certain new phenone derivatives of the formula (I) ##STR1## in which R.sup.1 =CH.sub.3,R.sup.2 =H, Cl, Br, I, methyl, hydroxy, methoxy, propoxy, propoxy or ethoxy;R.sup.3 =H or .beta.-D-glykosyl;R.sup.4 =H, Cl, Br, I, methyl, hydroxy, methoxy, propoxy, iso-propoxy or ethoxy;R.sup.5 =H or hydroxy,and the pharmaceutically acceptable salts, ethers and esters thereof, with the exception of the compounds 4-hydroxyacetophenone, 4-hydroxy-3-methoxy-acetophenone, 4-glucopyranosyloxy-acetophenone, 4-glucopyranosyloxy-3-methoxyacetophenone, 4-galactopyranosyloxy-3-methoxy-acetophenone, 4-glucopyranosyloxy-3,5-dimethoxy-acetophenone and galactopyranosyloxy-3,5-dimethoxy-acetophenone and a method for manufacturing them and pharmaceutical preparations containing them. The invention also concerns pharmaceutical preparations containing at least one compound of the formula (II) ##STR2## in which R.sup.1 denotes H, OH, alkoxy or C.sub.1-8 alkyl;R.sup.2 denotes H or C.sub.1-4 alkoxy;R.sup.3 denotes OH or a .beta.
    Type: Grant
    Filed: February 18, 1992
    Date of Patent: January 2, 1996
    Assignee: Plantamed Arzneimittel GmbH
    Inventors: Hildebert Wagner, Walter Dorsch, Hermann Stuppner, Sandor Antus
  • Patent number: 5430172
    Abstract: A process for preparing 4-alkanoylaryl benzyl ethers of the general formula I ##STR1## where R is hydrogen, halogen, cyano; alkyl, alkoxy;X is CH.sub.2, CH--CH.sub.3, CH--CH.sub.2 --CH.sub.3, CH--OCH.sub.3 or N--OCH.sub.3 ;Y is oxygen, sulfur, direct linkage or nitrogen;m is 0, 1, 2 or 3;R.sup.1 is hydrogen; alkyl, alkenyl, alkynyl or alkoxy;R.sup.2 is cyano, halogen, alkyl, alkoxy or haloalkyl;R.sup.3 is alkyl; haloalkyl; cycloalkyl; or an unsubstituted or substituted mono- to trinuclear aromatic system,comprises reacting an aryl benzyl ether of the general formula II ##STR2## where X, Y, R, R.sup.1, R.sup.2 and m have the abovementioned meanings, with a carbonyl halide or with a carboxylic anhydride or with a carboxylic sulfonic anhydride in the presence of an acid and in the presence or absence of a diluent.
    Type: Grant
    Filed: April 15, 1994
    Date of Patent: July 4, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Wassilios Grammenos, Wolfgang Siegel, Klaus Oberdorf, Bernd Mueller, Hubert Sauter, Reinhard Doetzer
  • Patent number: 5426206
    Abstract: Methods are provided for preparing all four diastereomers of 2-alkyl-3-hydroxyalkanals, 2-alkyl-3-silyloxyalkanals, and the like, with high enantiocontrol, using non-aldol chemistry. The synthetic methods also provide novel, stereospecific routes to polypropinates and chiral 2-substituted-1,3 diols.
    Type: Grant
    Filed: November 24, 1993
    Date of Patent: June 20, 1995
    Assignee: The Regents of the University of California
    Inventors: Michael E. Jung, Derin C. D'Amico
  • Patent number: 5393917
    Abstract: A process for isolating and purifying oxadimethacrylics of the general formula ICH.sub.2 .dbd.C(A)CH.sub.2 --O--CH.sub.2 C(B).dbd.CH.sub.2 Iwhere A and B are selected from the group consisting of --COOR.sup.1, --COR.sup.1, --CONR.sup.2 R.sup.3 and --CN and R.sup.1, R.sup.2 and R.sup.3 are each defined as follows:R.sup.1 is hydrogen, alkyl, substituted or unsubstituted cycloalkyl or cycloalkylalkyl, hydroxyalkyl, aminoalkyl, N-alkylaminoalkyl, N,N-dialkylaminoalkyl, substituted or unsubstituted aryl or arylalkyl,R.sup.2 and R.sup.3 are each hydrogen, alkyl, substituted or substituted cycloalkyl or cycloalkylalkyl, substituted or unsubstituted aryl or arylalkyl,comprises precipitating or crystallizing them from their solutions that contain at least one liquid hydrocarbon compound.
    Type: Grant
    Filed: December 16, 1993
    Date of Patent: February 28, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Siegmund Besecke, Andreas Deckers, Harald Lauke
  • Patent number: 5360938
    Abstract: This invention relates to asymmetric syntheses in which a prochiral or chiral compound is contacted in the presence of an optically active metal-ligand complex catalyst to produce an optically active product.
    Type: Grant
    Filed: July 16, 1992
    Date of Patent: November 1, 1994
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: James E. Babin, Gregory T. Whiteker
  • Patent number: 5329023
    Abstract: The invention relates to a method of preparing optically active alcohols which consist substantially (at least 75% e.e.) or entirely of one enantiomer of formula 4 ##STR1## wherein R and A are as defined therein. The method comprises, which maintaining enantiomeric excess, converting an optically active cyanohydrin of formula 1 ##STR2## into optically active protected cyanohydrin of formula 2 ##STR3## converting the protected cyanohydrin of formula 2 into an optically active compound of formula 3 ##STR4## removing the protecting group B.
    Type: Grant
    Filed: June 15, 1992
    Date of Patent: July 12, 1994
    Assignee: Duphar International Research B.V.
    Inventors: Johannes Brussee, Arne Van Der Gen
  • Patent number: 5292947
    Abstract: This invention relates to a process for preparing an alkylsulfonic anhydride comprising contacting(A) a dehydrated phosphoric acid with(B) an alkylsulfonic acid having 1 to 6 carbon atoms, under conditions of temperature and pressure to result in the substituted absence of phosphoric/alkylsulfonic mixed anhydride and production of a mixture of alkylsulfonic acid and its corresponding anhydride at a conversion of at least 10% of alkylsulfonic acid to the corresponding alkylsulfonic anhydride.
    Type: Grant
    Filed: September 28, 1992
    Date of Patent: March 8, 1994
    Assignee: Eastman Kodak Company
    Inventor: Theodore R. Walker, Jr.
  • Patent number: 5232915
    Abstract: 9.alpha.-Hydroxy-19,11.beta.-bridged steroids of general formula I ##STR1## are described. The more detailed meaning of A, B, R.sup.1, R.sup.2, G, Z, R.sup.4 --Y and R.sup.4' --Y' follows from the description. The steroids of general formula I have antigestagen and/or antiglucocorticoidal action and can be used for the production of pharmaceutical agents.
    Type: Grant
    Filed: January 14, 1992
    Date of Patent: August 3, 1993
    Assignee: Schering Aktiengesellschaft
    Inventors: Eckhard Ottow, Gunter Neef, Rudolf Wiechert, Walter Elger, Sybille Beier, Karl-Heinrich Fritzemeier
  • Patent number: 5196606
    Abstract: A novel synthesis of aromatic tertiary amines involves reacting an aromatic anil and an aromatic ether in a molar ratio of 1:1; adjusting the ratio to 2:1 produces novel enamines and by employing a two step process for enamine production, various unsymmetrically substituted enamines can be obtained which are readily hydrolyzed to corresponding deoxybenzoins which in turn are readily oxidized to benzils, the aromatic tertiary amines may be used to produce charge transport layers in xerography, while the benzils may be used to produce a variety of desired polymers.
    Type: Grant
    Filed: November 26, 1991
    Date of Patent: March 23, 1993
    Inventors: Allan S. Hay, Martino Paventi
  • Patent number: 5185447
    Abstract: Ketones having formulas (1)-(3) are provided by improved methods which involve the treatment of compounds having formulas (9)-(11) with aqueous base. ##STR1## wherein R.sub.x is NO.sub.2.
    Type: Grant
    Filed: January 29, 1992
    Date of Patent: February 9, 1993
    Assignee: Du Pont Merck Pharmaceutical Company
    Inventor: Edward C. Crapps
  • Patent number: 5171891
    Abstract: The present invention is directed to a process of oxidizing organic compounds having allylic or benzylic carbon atoms. The process of this invention comprises reacting an organic compound having one or more allylic or benzylic carbon atoms with an effective amount of an effective oxidizing agent in water at a temperature equal to or greater than about 350.degree. C. and at a pressure equal to or greater than about 175 atmospheres, wherein said agent is selected from the group consisting of elemental sulfur, an oxidized form of elemental sulfur and, an organic or inorganic compound capable of forming elemental sulfur or said oxidized forms in situ under process conditions.
    Type: Grant
    Filed: September 1, 1987
    Date of Patent: December 15, 1992
    Assignee: Allied-Signal Inc.
    Inventors: Divakaran Masilamani, David M. Hindenlang
  • Patent number: 5171880
    Abstract: The present invention is directed to a process of oxidizing organic compounds having benzylic carbon atoms. The process of this invention comprises reacting an organic compound having one or more benzylic carbon atoms with an effective amount of an effective oxidizing agent in water at a temperature equal to or greater than about 350.degree. C. and at a pressure equal to or greater than about 175 atmospheres, wherein said agent is selected from the group consisting of a combination of one or more bases and one or more of elemental sulfur, an oxidized form of elemental sulfur and/or an organic or inorganic sulfur containing compounds capable of forming elemental sulfur, said oxidized forms or a combination thereof in situ under process conditions, and organic or inorganic compounds which form one or more bases and elemental sulfur, oxidized forms of sulfur or a combination thereof in situ under process conditions.
    Type: Grant
    Filed: March 15, 1991
    Date of Patent: December 15, 1992
    Assignee: Allied-Signal Inc.
    Inventors: Divakaran Masilamani, David M. Hindenlang
  • Patent number: 5159082
    Abstract: A process for producing an aromatic compound is disclosed, which comprises coupling an aromatic sulfinic acid or a salt thereof with an aromatic halogen compound having at least one halogen atom attached to the carbon atom of the aromatic nucleus thereof or a vinyl group-containing halogen compound having at least one halogen atom attached to the carbon atom of said vinyl group in the presence of a catalyst compound containing an element selected from platinum metals.
    Type: Grant
    Filed: June 25, 1990
    Date of Patent: October 27, 1992
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Keiichi Sato, Toru Okoshi
  • Patent number: 5117062
    Abstract: A novel synthesis of aromatic tertiary amines involves reacting an aromatic anil and an aromatic ether in a molar ratio of 1:1; adjusting the ratio to 2:1 produces novel enamines and by employing a two step process for enamine production, various unsymmetrically substituted enamines can be obtained which are readily hydrolyzed to corresponding deoxybenzoins which in turn are readily oxidized to benzils, the aromatic tertiary amines may be used to produce charge transport layers in xerography, while the benzils may be used to produce a variety of desired polymers.
    Type: Grant
    Filed: January 22, 1991
    Date of Patent: May 26, 1992
    Inventors: Allan S. Hay, Martino Paventi
  • Patent number: 5091587
    Abstract: A process for the preparation of ketones which comprises reacting a conjugated diolefin and water in the liquid phase in the presence of a catalyst system comprising:a) a group VIII metal compound, andb) a source of protons.
    Type: Grant
    Filed: November 19, 1990
    Date of Patent: February 25, 1992
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 5068447
    Abstract: Aromatic carbonyl compounds, in particular arylene ether ketones, are prepared by reacting an appropriate reagent system in the presence of free Lewis acid and a complex between a Lewis acid, for example, aluminum trichloride, and an inorganic salt controlling agent, for example, lithium chloride, and, optionally, a diluent, such as methylene chloride. The process is particularly advantageous for the preparation of substantially or all para-linked arylene ether ketones as the presence of the Lewis acid/Lewis base complex markedly reduces alkylation and ensures the substantial absence of ortho substitution.
    Type: Grant
    Filed: July 6, 1990
    Date of Patent: November 26, 1991
    Assignee: Raychem Corporation
    Inventors: Heinrich C. Gors, Patrick J. Horner, Viktors Jansons