Monocyclic Acid Moiety Patents (Class 560/103)
  • Patent number: 6458757
    Abstract: The present invention relates to a process for the production of perfuming compositions, to perfumed products, and to products obtained therefrom. More specifically, the present invention concerns a process for the production of perfuming compositions, perfumed products and substances for perfumery characterized in that they comprise, as an active ingredient with an influence on the scent, an effective quantity of an alkylsalicylic acid ester.
    Type: Grant
    Filed: April 24, 1998
    Date of Patent: October 1, 2002
    Inventor: Isabelle Storet
  • Patent number: 6436991
    Abstract: Ferulate compounds derived from extracts from the plant Commiphora wightii are used in compositions and methods for prevention and treatment of abnormal cell growth and proliferation in inflammation, neoplasia and cardiovascular disease.
    Type: Grant
    Filed: May 21, 2001
    Date of Patent: August 20, 2002
    Assignees: Sabinsa Corporation, Sami Chemicals & Extracts (P) Ltd.
    Inventors: Muhammed Majeed, Vladimir Badmaev, Rajinder Kumar Bammi, Subbalakshmi Prakash, Sankaran Natarajan
  • Patent number: 6420596
    Abstract: This invention provides a process for the selective esterfication of a tertiary alcohol(I) by an acid anhydride(II) to produce corresponding tertiary ester(III) and carboxylic acid(V), using a reusable solid catalyst(IV) comprising one or more halides of indium, gallium, zinc and iron. The process comprises: (i) contacting a mixture of (I) and (II) in the absence or presence of a non aqueous solvent with the fine particles of (IV) in a stirred batch reactor provided with a reflux water condenser at atmospheric pressure at the reaction conditions, such that the mole ratio of (II) to (I) is in the range from about 0.1 to about 10.0; the weight ratio of (IV) to (I+II) is in the range from about 0.005 to about 0.5; the reaction temperature is below about 80° C., and the reaction period is in the range from about 0.1 h to about 50 h; (ii) removing the solid catalyst(IV) from the reaction mixture by filtration; and (iii) reusing the separated solid catalyst for subsequent batch of the process.
    Type: Grant
    Filed: November 29, 2000
    Date of Patent: July 16, 2002
    Assignee: Council of Scientific and Industrial Research
    Inventors: Vasant Ramchandra Choudhary, Kshudiram Mantri, Suman Kumar Jana
  • Patent number: 6399810
    Abstract: Methyl cyclohexyl-propionate is prepared by the hydrogenation of methyl cinnamate in the presence of a ruthenium and/or palladium catalyst.
    Type: Grant
    Filed: August 15, 2000
    Date of Patent: June 4, 2002
    Assignee: Haarmann & Reimer GmbH
    Inventors: Walter Kuhn, Hans-Ulrich Funk, Gerhard Senft, Wolfgang Kiel
  • Patent number: 6392089
    Abstract: Alcohol, phosphate, and diacid derivatives that may be deprotected by irradiation are disclosed. The protecting group is an arylacyl or heteroarylacyl group.
    Type: Grant
    Filed: March 31, 2000
    Date of Patent: May 21, 2002
    Assignee: University of Maryland
    Inventors: Daniel E. Falvey, Kwangjoo Lee, Anamitro Banerjee
  • Patent number: 6388123
    Abstract: The present invention relates to novel compounds of the formula (I) in which Het represents one of the groups  in which A, B, D, G, V, W, X, Y and Z are as defined in the description, processes and intermediates for their preparation, and to their use as pesticides and herbicides.
    Type: Grant
    Filed: June 1, 2001
    Date of Patent: May 14, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Volker Lieb, Hermann Hagemann, Arno Widdig, Michael Ruther, Reiner Fischer, Thomas Bretschneider, Christoph Erdelen, Ulrike Wachendorff-Neumann, Alan Graff, Udo Schneider
  • Patent number: 6384265
    Abstract: The present invention provides a method for producing an &agr;-acyloxy carbonyl compound from an enol ester epoxide stereoselectively using an acid catalyst which is capable of affecting rearrangement of the enol ester epoxide with inversion of stereochemistry. The present invention also provides a method for kinetic resolution of a stereoisomeric mixture of enol ester epoxides using a chiral catalyst. The kinetic resolution generally involves stereoselectively producing one particular enantiomer of &agr;-acyloxy carbonyl compounds from the stereoisomeric mixture of enol ester epoxides.
    Type: Grant
    Filed: March 23, 2000
    Date of Patent: May 7, 2002
    Assignee: Colorado State University Research Foundation
    Inventor: Yian Shi
  • Patent number: 6316616
    Abstract: The present invention provides methods and compositions, i.e. synthetic libraries of candidate compounds, useful in the discovery and optimization of compounds which catalyze at least one chemical transformation. In certain instances, the subject compounds catalyze a chemoselective, regioselective, stereoselective or enantioselective transformation.
    Type: Grant
    Filed: April 22, 1998
    Date of Patent: November 13, 2001
    Assignee: President and Fellows of Harvard College
    Inventors: Eric N. Jacobsen, Matthew S. Sigman
  • Patent number: 6310235
    Abstract: The invention relates to an improved method for producing ester plasticizers by reacting di- or polycarboxylic acids or their anhydrides with alcohols in the presence of metal catalysts.
    Type: Grant
    Filed: November 17, 1999
    Date of Patent: October 30, 2001
    Assignee: Celanese GmbH
    Inventor: Wilhelm Gick
  • Patent number: 6307091
    Abstract: The present invention is to provided a trifluoro-substituted benzoic acid, an ester thereof, particularly 2,3,4-trifluoro-5-iodobenzonic acid, 2,3,4-trifluoro-5-trifluoromethylbenzonic acid, esters thereof, which are useful as a starting material for synthesizeing a quinolonecarboxylic acid compound useful as a medicine, an anti-bacterial agent or an antiviral agent, and processes for preparing these compounds and 2,4,5-trifluoro-3-iodobenzonic acid, 2,4,5-trifluoro-3-trifluoromethylbenzoic acid and esters thereof.
    Type: Grant
    Filed: October 3, 2000
    Date of Patent: October 23, 2001
    Assignee: Ube Industries, Ltd.
    Inventors: Yasuhito Yamamoto, Yasuhiro Yoneda, Kikuo Ataka, Naoyuki Yokota
  • Patent number: 6303812
    Abstract: Disclosed is a method of isolating the aromatic product formed when a substrate having the general formula is dehalogenated, forming a product mixture of copper salts and aromatic product, where X is the halogen removed from the substrate to form the aromatic product, R′ is COOH, COOR, COR, CN, COH(R)2, or SO3H, each R″ is independently selected from halogen, R, or OR or two vicinal R″ groups form one or more fused aromatic rings, R is alkyl from C1 to C18 or aryl from C6 to C18, and n is 1 to 4. Water in an amount about 1 to about 5 times the amount of the substrate is added to the product mixture, forming an organic phase that contains the aromatic product and an aqueous phase that contains the copper salts. If the density of the organic phase differs from the density of said aqueous phase by less than 0.1 g/cc, a suitable solvent is added to the product mixture in an amount sufficient to increase the differences between the organic and aqueous phases to at least 0.
    Type: Grant
    Filed: February 15, 2000
    Date of Patent: October 16, 2001
    Assignee: Occidental Chemical Corporation
    Inventors: Michael J. Fifolt, Michael C. Savidakis, Ronald Spohn, Daniel R. Thielen, William S. Derwin, David C. Johnson
  • Patent number: 6303052
    Abstract: An antioxidant composition comprising at least one compound having the formula: wherein R1 and R2 are each hydrocarbon groups having from 1 to 8 carbon atoms, a is from 1 to 3, R3 is a linear alkyl group having from 4 to 22 carbon atoms, and R4 is a linear alkyl group having from 6 to 24 carbon atoms.
    Type: Grant
    Filed: March 2, 1999
    Date of Patent: October 16, 2001
    Assignee: Condea Vista Company
    Inventors: Shirley A. Moy, Kurt W. McWilliams
  • Patent number: 6274700
    Abstract: In a process for preparing polytetrahydrofuran, polytetrahydrofuran copolymers or diesters or monoesters thereof by polymerization of tetrahydrofuran in the presence of at least one telogen and/or comonomer over acid-activated montmorillonite catalysts, the montmorillonite catalyst after acid activation has a ratio of montmorillonite structure to the sum of muscovite and kaolin structures, determined from the intensities of the reflections at 2&thgr;=5.5° for montmorillonite, 2&thgr;=9.0° for muscovite and 2&thgr;=12.5° for kaolin measured in the X-ray powder pattern, of at least 5:1.
    Type: Grant
    Filed: June 8, 2000
    Date of Patent: August 14, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Karsten Eller, Heinz Rütter, Michael Hesse, Rainer Becker
  • Patent number: 6268526
    Abstract: A mixture formed from an aromatic substituted alcohol and/or an aromatic substituted alkyl halide, and a copper-free palladium catalyst is carbonylated with carbon monoxide. Extremely high yields of the desired alpha-substituted carboxylic acid can be obtained in very short reaction periods by use of a palladium catalyst that is formed from a palladium compound with a valence of zero to two and a cycloalkyldiarylphosphine ligand, such as neomenthyldiphenylphosphine.
    Type: Grant
    Filed: December 16, 1998
    Date of Patent: July 31, 2001
    Assignee: Albemarle Corporation
    Inventor: Tse-Chong Wu
  • Patent number: 6268527
    Abstract: The invention relates to a method for producing a benzoic acid derivative represented by the general formula (1). The method includes the step of reacting an aromatic compound represented by the general formula (2), with carbon monoxide and a hydroxy compound (i.e., water or an alcohol), in the presence of (a) a metal compound containing a metal of 8, 9 and 10 groups of periodic table, (b) a first phosphine derivative represented by the general formula (R1)2P—Q—P(R1)2, and (c) a base, It is possible to easily and efficiently produce the benzoic acid derivative by the method.
    Type: Grant
    Filed: December 2, 1999
    Date of Patent: July 31, 2001
    Assignee: Central Glass Company, Limited
    Inventors: Makoto Koide, Michio Ishida, Yuzuru Morino, Seiji Hasegawa, Satoru Narizuka, Takashi Kume
  • Patent number: 6235924
    Abstract: The present invention provides a continuous series of at least 3 esterification reactions, each of which yields highly pure esters derived from benzoic and at least one alcohol selected from monohydric alcohols containing from 6 to 12 carbon atoms and dihydric alcohols containing from 2 to 8 carbon atoms. At least a portion of the esterification catalyst and high boiling impurities remaining following distillation of the desired ester are used in the reaction mixture for the next reaction of the series.
    Type: Grant
    Filed: August 7, 2000
    Date of Patent: May 22, 2001
    Assignee: Velsicol Chemical Corporation
    Inventors: Wesley Wayne McConnell, Bruce Edward Stanhope, Franz Josef Luxem
  • Patent number: 6211401
    Abstract: Polytetrahydrofuran, tetrahydrofuran copolymers, diesters or monoesters of these polymers are prepared by polymerizing tetrahydrofuran in the presence of at least one telogen and/or comonomer on a heterogeneous carrier catalyst which contains on an oxidic carrier material as active mass a catalytically active amount of at least one oxygenous molybdenum and/or tungsten compound and, when the precursor compounds of the active mass have been applied to the carrier material precursor, has been calcined at temperatures of between 500° C. and 1000° C. The catalyst used contains a promotor which comprises at least one element or a compound of an element of the 2nd, 3rd including the lanthanides, 5th, 6th, 7th, 8th or 14th group of the periodic system of elements.
    Type: Grant
    Filed: May 19, 1999
    Date of Patent: April 3, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Karsten Eller, Christoph Sigwart, Rainer Becker, Klaus-Dieter Plitzko, Rolf Fischer, Frank Stein, Ulrich Müller, Michael Hesse
  • Patent number: 6211399
    Abstract: Disclosed is a method of adding 1 to 4 chlorine or bromine atoms to an aromatic ring of compound that has at least one electron-withdrawing groups on that ring. The aromatic compound is reacted with a chlorinating agent or a brominating agent in the presence of about 0.1 to about 10 mole % of a Lewis acid catalyst at a temperature of ambient to about 100° C. and a pressure of about 10 to about 100 psig.
    Type: Grant
    Filed: October 5, 1999
    Date of Patent: April 3, 2001
    Assignee: Occidental Chemical Corporation
    Inventors: Michael C. Savidakis, David C. Johnson
  • Patent number: 6201147
    Abstract: The invention relates to a process for the resolution of esters of arylalkylcarboxylic acids of the general formula which comprises reacting compounds of the general formula I with an alcohol of the general formula R6—OH in the presence of a lipase or esterase to give compounds of the general formulae Ia and II at least one of the compounds of the formulae Ia and II being present in an enantiomeric excess and the substituents and variables in the formulae I, Ia and II are as defined in the specification.
    Type: Grant
    Filed: September 21, 1999
    Date of Patent: March 13, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Uwe Bornscheuer, Erik Henke, Yang Hong
  • Patent number: 6201020
    Abstract: This invention relates to compounds, pharmaceutical compositions, and methods of using compounds of the formula: A is O or S; R is C1-C10 straight or branched chain alkyl, C2-C10 straight or branched chain alkenyl, C2-C10 straight or branched chain alkynyl, aryl, heteroaryl, carbocycle, or heterocycle; D is a bond, or a C1-C3 straight or branched chain alkyl, C2-C3 straight or branched chain alkenyl, C2-C3 straight or branched chain alkynyl, wherein any of the carbon atoms of said alkyl, alkenyl, or alkynyl of D are optionally replaced with oxygen, nitrogen, or sulfur; and X is aryl, heteroaryl, carbocycle, or heterocycle.
    Type: Grant
    Filed: December 31, 1998
    Date of Patent: March 13, 2001
    Assignee: Guilford Pharmaceuticals, Inc.
    Inventors: Jie Zhang, Larisa E. Serdyuk, Jia-He Li
  • Patent number: 6166273
    Abstract: A process is provided for increasing the fluorine content of benzene or pyridine rings which are optionally substituted with from 1 to 3 inert substituents. The process involves (a) contacting the ring with a metal fluoride composition comprising cupric fluoride (CuF.sub.2) at a temperature above 250.degree. C. sufficient to transfer F from cupric fluoride to the optionally substituted ring, thereby chemically reducing the metal fluoride composition; (b) oxidizing the reduced metal fluoride composition from (a) in the presence of HF to regenerate a metal fluoride composition comprising cupric fluoride; and (c) employing regenerated metal fluoride composition of (b) in (a).
    Type: Grant
    Filed: July 27, 1999
    Date of Patent: December 26, 2000
    Assignee: E.I. du Pont de Nemours and Company
    Inventor: Munirpallam A. Subramanian
  • Patent number: 6162943
    Abstract: Process for the preparation of .alpha.-alkoxy-.alpha.-trifluoromethyl-arylacetic esters of the formula (I) ##STR1## wherein R is a component selected from the group consisting of C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.3 -C.sub.7 -cycloalkyl, C.sub.6 -C.sub.10 -aryl and C.sub.1 -C.sub.6 -halogenoalkyl, R' is selected from the group consisting of C.sub.1 -C.sub.4 -alkyl, X is selected from the group consisting of halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.6 -C.sub.10 -aryl or C.sub.1 -C.sub.4 -alkoxy and nitro, and n is zero or an integer from 1 to 3.
    Type: Grant
    Filed: April 16, 1999
    Date of Patent: December 19, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventors: Norbert Lui, Albrecht Marhold
  • Patent number: 6160171
    Abstract: The present invention is to provide a trifluoro-substituted benzoic acid, an ester thereof, particularly 2,3,4-trifluoro-5-iodobenzoic acid, 2,3,4-trifluoro-5-trifluoromethylbenzoic acid, esters thereof, which are useful as a starting material for synthesizing a quinolonecarboxylic acid compound useful as a medicine, an anti-bacterial agent or an antiviral agent, and processes for preparing these compounds and 2,4,5-trifluoro-3-iodobenzoic acid, 2,4,5-trifluoro-3-trifluoromethylbenzoic acid and esters thereof.
    Type: Grant
    Filed: February 17, 1999
    Date of Patent: December 12, 2000
    Assignee: Ube Industries, Ltd.
    Inventors: Yasuhito Yamamoto, Yasuhiro Yoneda, Kikuo Ataka, Naoyuki Yokota
  • Patent number: 6130349
    Abstract: Complexes of a selected class of chiral ligands with molybdenum, tungsten or chromium, preferably molybdenum, are effective as catalysts in highly enantioselective and regioselective alkylation of allylic substrates. Such compositions provide a versatile and low-cost alternative to existing catalysts.
    Type: Grant
    Filed: December 15, 1998
    Date of Patent: October 10, 2000
    Assignee: The Board of Trustees of the Leland Stanford Junior University
    Inventors: Barry M. Trost, Iwao Hachiya
  • Patent number: 6124474
    Abstract: A process for preparing chiral isomers of N-protected 2-azetidinemethanol compounds, particularly N-(phenylmethyl)-2-azetidinemethanol and N-BOC-2-azetidinemethanol, and especially the (R)-isomers thereof, as well as O-substituted derivatives thereof.
    Type: Grant
    Filed: December 21, 1999
    Date of Patent: September 26, 2000
    Assignee: Abbott Laboratories
    Inventors: Anthony R. Haight, John E. Lallaman, Gregory S. Wayne
  • Patent number: 6118018
    Abstract: Disclosed is a method of adding 1 to 4 chlorine or bromine atoms to an aromatic ring of compound that has at least one electron-withdrawing groups on that ring. The aromatic compound is reacted with a chlorinating agent or a brominating agent in the presence of about 0.1 to about 10 mole % of a Lewis acid catalyst and about 0.001 to about 0.1 equivalents of an iodine-containing cocatalyst at a temperature of ambient to about 100.degree. C.
    Type: Grant
    Filed: December 6, 1999
    Date of Patent: September 12, 2000
    Assignee: Occidental Chemical Corporation
    Inventors: Michael C. Savidakis, Michael J. Fifolt, Daniel R. Thielen, Ronald Spohn, David C. Johnson, William S. Derwin
  • Patent number: 6111147
    Abstract: Polytetrahydrofuran, copolymers of tetrahydrofuran and 2-butyne-1,4-diol, diesters of these polymers with C.sub.2 -C.sub.20 -monocarboxylic acids or monoesters of these polymers with C.sub.1 -C.sub.10 -monocarboxylic acids are prepared by polymerization of tetrahydrofuran in the presence of one of the telogens water, 1,4-butanediol, 2-butyne-1,4-diol, polytetrahydrofuran having a molecular weight of from 200 to 700 Dalton, a C.sub.1 -C.sub.10 -monocarboxylic acid or an anhydride of a C.sub.2 -C.sub.20 -monocarboxylic acid or a mixture of these telogens over a heterogeneous supported catalyst which comprises a catalytically active amount of an oxygen-containing molybdenum and/or tungsten compound on an oxidic support material and which has been calcined at from 5OO.degree. C. to 1OOO.degree. C.
    Type: Grant
    Filed: April 1, 1999
    Date of Patent: August 29, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Christoph Sigwart, Karsten Eller, Rainer Becker, Klaus-Dieter Plitzko, Rolf Fischer, Frank Stein, Ulrich Mueller, Michael Hesse
  • Patent number: 6103926
    Abstract: Direct preparation of benzylically halogenated alkylbenzoic acid ester from an alkylbenzoic acid ester in which the alkyl group is a primary or secondary alkyl group is carried out. The ester group of the starting ester (i) is devoid of non-aromatic unsaturation and (ii) if an aromatic group, is devoid of ring substitution that would undergo benzylic halogenation. The process comprises slowly feeding halogen continuously and/or intermittently to an agitated solution of the alkylbenzoic acid ester in a liquid halogen-containing solvent maintained at a thermal halogenation temperature such that when the alkyl group of the alkylbenzoic acid ester is a primary alkyl group and monohalogenation is desired, the total amount of halogen fed does not exceed about 0.8 mole of halogen per mole of alkylbenzoic acid ester. If the alkylbenzoic acid ester is a toluic acid ester and dihalogenation is desired, the amount of halogen fed is over 1 mole but no more than about 1.8 moles per mole of the toluic acid ester.
    Type: Grant
    Filed: March 12, 1999
    Date of Patent: August 15, 2000
    Assignee: Albemarle Corporation
    Inventor: Hassan Y. Elnagar
  • Patent number: 6090168
    Abstract: The present application relates to a series of novel sulfonic acid metal cation salts of the formula ##STR1## which are useful intermediates to prepare antifolate 5-substituted pyrrolo[2,3-d]pyrimidines. The present invention also relates to a novel process for preparing the sulfonic acid metal cation salts and to a novel process for preparing aldehydes of the formula ##STR2## from the corresponding sulfonic acid metal cation salts.
    Type: Grant
    Filed: October 6, 1999
    Date of Patent: July 18, 2000
    Assignee: Eli Lilly and Company
    Inventors: Douglas Patton Kjell, Brian James Slattery, Charles Jackson Barnett
  • Patent number: 6054605
    Abstract: The present invention is to provide 2,3-dihalogeno-6-trifluoromethylbenzene derivatives represented by a general formula [I]; ##STR1## wherein X.sub.1 and X.sub.2 are the same or different and each independently represents fluoro or chloro; Y represents COOH, CONH.sub.2, CN, CHO, CH.dbd.NOH or COOR', wherein R' is C.sub.1 -C.sub.4 alkyl, except the case that X.sub.1 and X.sub.2 are each chloro and Y is COOH, which are useful as the starting materials for producing pesticides, drugs and the like, and a process for producing such derivatives.
    Type: Grant
    Filed: February 12, 1999
    Date of Patent: April 25, 2000
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Isamu Kasahara, Tadashi Sugiura, Tsutomu Inoue
  • Patent number: 6017541
    Abstract: Methods are described for the rapid synthesis in satisfactory yield of methyl ecgonine phenylphosphonates as analogues of transition states for the hydrolysis of the benzoyl ester of an ecgonine derivative, namely cocaine, and their linking to carrier proteins, for the purpose of using them as immunogens. The resulting immunogens elicit the formation in experimental animals of antibodies able to promote the hydrolysis of cocaine. Both these catalytic anti-cocaine antibodies and the immunogens themselves are potentially useful for the treatment of individuals seeking to avoid the pharmacological effects of cocaine and in diagnostic applications.
    Type: Grant
    Filed: August 5, 1997
    Date of Patent: January 25, 2000
    Inventors: Brian H. Barber, Neal den Hollander, Jiri J. Krepinsky, M. Younus Meah
  • Patent number: 6005135
    Abstract: Water-borne polymeric vehicles are described where the polymeric vehicle includes the amine or ammonium salt of a phenolic ester alcohol.
    Type: Grant
    Filed: March 21, 1996
    Date of Patent: December 21, 1999
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Frank N. Jones, Ramachandran P. Subrayan
  • Patent number: 5981595
    Abstract: A pharmaceutically useful compound which lowers blood cholesterol levels having the formula ##STR1## wherein X is oxygen or --NH--; Ar is phenyl, substituted phenyl, naphthyl or substituted naphthyl; R.sub.1 is hydrogen, lower alkyl or benzyl; and R.sub.2 is a straight or branched alkyl group having from 5 to 17 carbon atoms which may be substituted on the 1-carbon position with methyl, ethyl, phenyl, or substituted phenyl, or a cycloalkyl group having from 3 to 8 carbon atoms.
    Type: Grant
    Filed: July 1, 1993
    Date of Patent: November 9, 1999
    Assignee: Warner-Lambert Company
    Inventors: Joseph Armand Picard, William Howard Roark, Bruce David Roth
  • Patent number: 5948922
    Abstract: Compounds containing two cyclic hydrocarbon moieties which are substituted to provide crosslinking functionality and which are linked to each other by secondary or tertiary oxycarbonyl containing moiety are basis for compositions which are cured to provide cured thermosets for encapsulation and underfill for electronic components that are thermally decomposable to allow repair, replacement, recovery or recycling of operative electronic components from assemblies that are inoperative.
    Type: Grant
    Filed: February 20, 1997
    Date of Patent: September 7, 1999
    Assignee: Cornell Research Foundation, Inc.
    Inventors: Christopher K. Ober, Hilmar Koerner
  • Patent number: 5886210
    Abstract: A method for synthesizing aromatic compounds by selectively dehalogenating aromatic starting materials is provided. Compounds may be prepared which are substituted with fluoro, chloro or bromo. The method may be used to remove halogen atoms from sites at which halogenation is not desired, and to form substantially pure halogenated compounds from mixtures of starting materials. The method uses a copper containing dehalogenation agent and an acid with the dehalogenation being controlled by a substituent such as a carboxylic acid, amide, ester, aldehyde, ketone or cyano on the aromatic ring.
    Type: Grant
    Filed: June 16, 1997
    Date of Patent: March 23, 1999
    Assignee: Rohm and Haas Company
    Inventors: Heather Lynnette Rayle, Randall Wayne Stephens
  • Patent number: 5874608
    Abstract: The present invention relates to a process for the preparation of compounds of the formula (1)R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 ArCOOR (1)in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are hydrogen, a halogen, an alkyl or alkoxy group having 1 to 6 carbon atoms or OR, NHR, NR.sub.2, SR or COOR, in which R is an alkyl radical having 1 to 4 carbon atoms, Ar is an aryl radical having 6 to 12 carbon atoms and the radical R shown in formula (1) has the above meaning, by reacting a compound of the formula (2)R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 ArCOOH (2)in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are hydrogen, a halogen, an alkyl or alkoxy group having 1 to 6 carbon atoms, OH, NH.sub.2, NHR, SH or COOH and Ar has the same meaning as in formula (1), with a sulfate of the formula (RO).sub.2 SO.sub.2, in which R has the above meaning, in the presence of a water-insoluble tertiary amine and water at a temperature of 10.degree.
    Type: Grant
    Filed: May 19, 1997
    Date of Patent: February 23, 1999
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ralf Pfirmann, Theodor Papenfuhs
  • Patent number: 5830244
    Abstract: A fuel additive having the formula: ##STR1## wherein R.sub.1 and R.sub.2 are independently hydrogen or lower alkyl; R.sub.3 and R.sub.4 are independently hydrogen or lower alkyl and each R.sub.3 and R.sub.4 is independently selected in each --O--CHR.sub.3 --CHR.sub.4 -- unit; R.sub.5 is hydrogen, alkyl having 1 to 100 carbon atoms, phenyl, aralkyl having 7 to 100 carbon atoms or alkaryl having 7 to 100 carbon atoms, or an acyl group of the formula: ##STR2## where R.sub.6 is alkyl having 1 to 30 carbon atoms, phenyl, aralkyl having 7 to 36 carbon atoms or alkaryl having 7 to 36 carbon atoms; n is an integer from 5 to 100; and x is an integer from 0 to 10.
    Type: Grant
    Filed: December 30, 1996
    Date of Patent: November 3, 1998
    Assignee: Chevron Chemical Company
    Inventor: Richard E. Cherpeck
  • Patent number: 5811576
    Abstract: Novel 4-oxoquinoline-3-carboxylic acid compounds of the formula: ##STR1## wherein R.sup.1 is cyclopropyl which may have 1 to 3 substituents of alkyl and halogen; phenyl which may be substituted by 1 to 3 substituents of alkoxy, halogen and OH; alkyl which may be substituted by halogen, alkanoyloxy or OH; alkenyl; or thienyl, R.sup.2 is 5- to 9-membered saturated or unsaturated heterocyclic ring which may be substituted, R.sup.3 is alkyl, R is H or alkyl, and X is halogen, and pharmaceutically acceptable salts thereof, said compounds having excellent antimicrobial activity and hence being useful as an antimicrobial agent, and a pharmaceutical composition containing said compound as an active ingredient.
    Type: Grant
    Filed: September 3, 1997
    Date of Patent: September 22, 1998
    Assignee: Otsuka Pharmaceutical Company, Limited
    Inventors: Hiraki Ueda, Hisashi Miyamoto, Hiroshi Yamashita, Hitoshi Tone
  • Patent number: 5783173
    Abstract: A sunscreen composition containing a UV-B dibenzoylmethane derivative, such as 4-(1,1-dimethylethyl)-4'-methoxydibenzoylmethane (PARSOL 1789), and a stabilizer/solubilizer for the dibenzoylmethane derivative selected from formula (I) and formula (II), and mixtures thereof: ##STR1## wherein m=5, 7, 9 or mixtures and n=4, 6, 8 or mixtures; ##STR2## wherein m=5, 7 or mixtures and n=4, 6 or mixtures.These long branched chain alkyl hydroxybenzoates and long branched chain benzoates having a C.sub.4.sup.+ branch at the 2 position are quite effective in stabilizing the dibenzoylmethane derivative UV-B filter compounds making them more effective; effective for longer periods of time.
    Type: Grant
    Filed: November 21, 1996
    Date of Patent: July 21, 1998
    Assignee: The C. P. Hall Company
    Inventors: Craig A. Bonda, Steven P. Hopper
  • Patent number: 5773648
    Abstract: A process for the preparation of polytetrahydrofuran or polytetrahydrofuran monoesters of C.sub.1 -C.sub.10 monocarboxylic acids by the polymerization of tetrahydrofuran over a heterogeneous catalyst in the presence of one of the telogens water, 1,4-butanediol or polytetrahydrofuran having a molecular weight of from 200 to 700 dalton or a C.sub.1 -C.sub.10 monocarboxylic acid or mixtures of these telogens, wherein a supported catalyst is used as catalyst, which contains a catalytically active amount of an oxygen-containing tungsten or molybdenum compound or mixtures of these compounds on an oxidic support material and which was calcined at temperatures ranging from 500.degree. to 1000.degree. C. following the application of the precursor compounds of said oxygen-containing molybdenum and/or tungsten compounds to the support material precursor.
    Type: Grant
    Filed: March 7, 1997
    Date of Patent: June 30, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Rainer Becker, Christoph Sigwart, Michael Hesse, Rolf Fischer, Karsten Eller, Gerd Heilen, Klaus-Dieter Plitzko
  • Patent number: 5756834
    Abstract: It is known to prepare fluorinated aromatic compounds of the formula I ##STR1## in which X, Y and Z can have the meaning specified in the description, by reacting aromatic compounds of the formula II ##STR2## in which X, Y and Z have the meaning specified for formula I, with fluorine in a reaction medium.According to the invention, the direct fluorination is carried out in a reaction medium containing polyfluoroalkanesulfonic acids of the formula IIICF.sub.n H.sub.3-n (CFY).sub.m --SO.sub.3 H (III)in whichm, n and Y have the meaning specified in the description.By this means, it is possible, particularly advantageously to provide a process, which improves the known processes not only with regard to the selectivity and the yield, but also with respect to the quality of the resulting products of the process in a manner not readily predictable.Fluorinated aromatic compounds of the formula I as intermediates for active compound synthesis.
    Type: Grant
    Filed: November 7, 1996
    Date of Patent: May 26, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Sergej Pasenok, Wolfgang Appel
  • Patent number: 5744628
    Abstract: The present invention relates to a process for the preparation of compounds of the formula (1)R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 ArCOOR (1)in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are hydrogen, a halogen, an alkyl or alkoxy group having 1 to 6 carbon atoms, OR, NHR, NR.sub.2, SR or COOR, R being an alkyl radical having 1 to 4 carbon atoms, Ar is an aryl radical having 6 to 12 carbon atoms and the radical R identified in formula (1) has the above meaning, by reacting a compound of the formula (2)R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 ArCOOH (2)in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are hydrogen, a halogen, an alkyl or alkoxy group having 1 to 6 carbon atoms, OH, NH.sub.2, NHR, SH or COOH and Ar has the same meaning as in formula (1), with a sulfate of the formula (RO).sub.2 SO.sub.
    Type: Grant
    Filed: July 29, 1996
    Date of Patent: April 28, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ralf Pfirmann, Theodor Papenfuhs
  • Patent number: 5744021
    Abstract: The invention relates to 2-alkylmercapto-4-(trifluoromethyl)benzoic esters of the formula (II), in which R.sup.1 and R.sup.2 are, independently of each other, (C.sub.1 -C.sub.6) alkyl, and a process for their preparation, which comprises reacting 3,4-dichlorobenzotrifluoride electrochemically at an anode with CO.sub.2 to give 2-chloro-4-(trifluoromethyl)-benzoate, converting it into the corresponding benzoic ester of the formula (I), and then reacting it with an alkylmercaptide R.sup.2 S.sup.e.
    Type: Grant
    Filed: December 20, 1996
    Date of Patent: April 28, 1998
    Assignee: Hoechst AG
    Inventors: Peter Brungs, Thomas Karcher, Klaus Kuhlein, Hans Millauer, Manfred Wildt
  • Patent number: 5739373
    Abstract: The present invention relates to catalytic asymmetric hydrogenation of phosphorus analogs of itaconic acid to synthesize novel optically active phosphono succinates.
    Type: Grant
    Filed: October 10, 1995
    Date of Patent: April 14, 1998
    Assignee: Monsanto Company
    Inventor: John J. Talley
  • Patent number: 5730985
    Abstract: Methods are described for the rapid synthesis in satisfactory yield of methyl ecgonine phenylphosphonates as analogues of transition states for the hydrolysis of the benzoyl ester of an ecgonine derivative, namely cocaine, and their linking to carrier proteins, for the purpose of using them as immunogens. The resulting immunogens elicit the formation in experimental animals of antibodies able to promote the hydrolysis of cocaine. Both these catalytic anti-cocaine antibodies and the immunogens themselves are potentially useful for the treatment of individuals seeking to avoid the pharmacological effects of cocaine and in diagnostic applications.
    Type: Grant
    Filed: June 13, 1994
    Date of Patent: March 24, 1998
    Assignee: Governing Council of the University of Toronto
    Inventors: Brian H. Barber, Neal den Hollander, Jiri J. Krepinsky, M. Younus Meah
  • Patent number: 5728867
    Abstract: Carbonyloxy-substituted azulenesquaric acid dyes of the formula ##STR1## where L is C.sub.1 -C.sub.12 -alkylene which may be substituted by phenyl,R.sup.1 is C.sub.1 -C.sub.12 -alkyl, monounsaturated or polyunsaturated C.sub.3 -C.sub.12 -alkenyl, which may be phenyl-substituted, C.sub.3 -C.sub.7 -cycloalkyl, C.sub.3 -C.sub.7 -cycloalkenyl, substituted or unsubstituted phenyl, pyrrolyl, furanyl, thienyl or pyridyl andR.sup.2, R.sup.3, R.sup.4 and R.sup.5 are each independently of the others hydrogen or substituted or unsubstituted C.sub.1 -C.sub.12 -alkyl,with the proviso that when R.sup.3 is hydrogen the positions of the substituents CH.sub.2 --L--O--CO--R.sup.1 and R.sup.4 on either or both azulene rings may also be interchanged with each other within an azulene ring, are useful in an optical recording medium.
    Type: Grant
    Filed: October 25, 1990
    Date of Patent: March 17, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Schmitt, Wolfgang Schrott, Peter Neumann, Sibylle Brosius, Klaus Dieter Schomann, Harald Kuppelmaier
  • Patent number: 5698735
    Abstract: Description here is a novel process for preparing phenyl acetic acid derivatives of the formula (I)Ar--CH.sub.2 --R.sup.1 (I)in which Ar and R.sup.1 are as defined in the description by reaction of sulfonyloxy-activated hydroxyacetic acid derivatives of the formula (II)R.sup.3 --SO.sub.2 --O--CH.sub.r --R.sup.1 (II)in which R.sup.3 is as defined in the description. with aromatics of the formula (III)Ar--H (III)has been found. The intermediates of the formula (II), some of which are novel, are obtained from hydroxyacetic acid derivatives by reaction with sulfonyl halides or sulfonic anhydrides. The phenylacetic acid derivatives are important starting materials for preparing pesticides.
    Type: Grant
    Filed: January 20, 1995
    Date of Patent: December 16, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventor: Uwe Stelzer
  • Patent number: 5686621
    Abstract: Substituted hydrindanes and their use in controlling angiogenesis-dependent diseases in warm blooded animals are disclosed.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: November 11, 1997
    Assignee: Alcon Laboratories, Inc.
    Inventors: Abbot F. Clark, Raymond E. Conrow
  • Patent number: 5675040
    Abstract: The invention relates to a process for the preparation of compounds of the formula ##STR1## characterized in that the radical X in sulphones of the formulaX--(CH.sub.2 --CH.sub.2 --O).sub.m --(CH.sub.2).sub.n --SO.sub.2 --CH.sub.2 --CH.sub.2 OH (2)is replaced by ##STR2## or a compound of the formula ##STR3## is added to the sulphone of the formulaCH.sub.2 .dbd.CH--SO.sub.2 --CH.sub.2 --CH.sub.2 --OH (3),the substituents having the meanings given in the description.
    Type: Grant
    Filed: September 19, 1996
    Date of Patent: October 7, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfgang Harms, Udo-Winfried Hendricks, Karl-Josef Herd, Klaus Kunde
  • Patent number: 5663448
    Abstract: Compounds of general formula (I), stereosiomers and pharmaceutically acceptable salts thereof, wherein each of Z and Z' are independently H or F; Q is (a), CH(OH), (b); X is H, Br, Cl, F or CF.sub.3 ; Y is H, Br, Cl, F, OH, OR.sub.5, OC(O)R.sub.4, N.sub.3, CN, NO.sub.2, SO.sub.3 H, CO.sub.2 R.sub.4, NH.sub.2, NHR.sub.9, NR.sub.9 R'.sub.9, C(R.sub.6)(R.sub.7)(V'R.sub.8) or C(O)R.sub.7, provided that when both Z and Z' are F, then Y is H or F; V and V' are each independently CH.sub.2 or O; R.sub.1 is H or CH.sub.3 ; R.sub.2, R.sub.9 and R'.sub.9 are each independently (C.sub.1-6)alkyl, or R.sub.2 and V--R.sub.3 taken together with the carbon atom to which they are attached form a 3-6 membered ring; R.sub.3, R.sub.6, R.sub.7 and R.sub.8 are each independently H, (C.sub.1-6)alkyl, or (C.sub.3-6)cycloalkyl; R.sub.4 is H, (C.sub.1-10)alkyl, (C.sub.0-4)alkylene aryl or (C.sub.3-8)cycloalkyl; and R.sub.5 is (C.sub.1-10)alkyl, benzyl, phenethyl or (C.sub.
    Type: Grant
    Filed: November 21, 1995
    Date of Patent: September 2, 1997
    Assignee: Merrell Pharmaceuticals Inc.
    Inventors: Jean-Noel Collard, Jean-Marie Hornsperger, Daniel Schirlin