Benzene Ring Containing Patents (Class 568/705)
  • Patent number: 9376323
    Abstract: An object of the invention is to provide a tetrafluoroborate producing method that allows high-yield, high-efficiency production of a tetrafluoroborate by a continuous process, a tetrafluoroborate-containing electrolyte, and an electrical storage device including such an electrolyte. The invention provides a method for producing a tetrafluoroborate, which includes: a first step including dissolving boron trifluoride gas in an organic solvent; a second step including adding, to the organic solvent, a fluoride (MFn, wherein M represents a metal or NH4, and 1?n?3) in an amount stoichiometrically equivalent to or less than the amount of the boron trifluoride so that a tetrafluoroborate solution is produced; and a third step including circulating the tetrafluoroborate solution through the first step so that the boron trifluoride gas is dissolved in the tetrafluoroborate solution instead of the organic solvent.
    Type: Grant
    Filed: June 19, 2009
    Date of Patent: June 28, 2016
    Assignee: STELLA CHEMIFA CORPORATION
    Inventors: Masahide Waki, Kazuhiro Miyamoto, Kazutaka Hirano
  • Publication number: 20140323727
    Abstract: Provided herein is a novel process for the preparation of phenylcyclopropylamine derivatives, which are useful intermediates in the preparation of triazolo[4,5-d]pyrimidine compounds. Provided particularly herein is a novel, commercially viable and industrially advantageous process for the preparation of a substantially pure ticagrelor intermediate, trans-(1R,2S)-2-(3,4-difluorophenyl)-cyclopropylamine. The intermediate is useful for preparing ticagrelor, or a pharmaceutically acceptable salt thereof, in high yield and purity.
    Type: Application
    Filed: July 1, 2014
    Publication date: October 30, 2014
    Inventors: Anil Shahaji Khile, Jayesh Patel, Nikhil Trivedi, Nitin Sharadchandra Pradhan
  • Patent number: 8802704
    Abstract: The invention relates to oxadiazole compounds of formula I. The compounds are useful e.g. in the treatment of autoimmune disorders, such as multiple sclerosis.
    Type: Grant
    Filed: March 29, 2010
    Date of Patent: August 12, 2014
    Assignee: Merck Serono SA
    Inventors: Anna Quattropani, Cyril Montagne, Wolfgang Sauer, Stefano Crosignani, Agnès Bombrun
  • Publication number: 20140051874
    Abstract: The present invention provides a method that allows production of stereospecific and asymmetrical five-membered ring-containing compounds serving as synthetic intermediates for formation of five-membered rings of prostaglandins and the like, with high yield and excellent stereoselectivity in terms of diastereoselectivity and enantioselectivity in a short process without requiring troublesome procedures such as optical resolution.
    Type: Application
    Filed: April 27, 2012
    Publication date: February 20, 2014
    Applicant: ONO PHARMACEUTICAL CO., LTD.
    Inventor: Yujiro Hayashi
  • Publication number: 20130150577
    Abstract: Provided herein is a novel process for the preparation of phenylcyclopropylamine derivatives, which are useful intermediates in the preparation of triazolo[4,5-d]pyrimidine compounds. Provided particularly herein is a novel, commercially viable and industrially advantageous process for the preparation of a substantially pure ticagrelor intermediate, trans-(1R,2S)-2-(3,4-difluorophenyl)-cyclopropylamine. The intermediate is useful for preparing ticagrelor, or a pharmaceutically acceptable salt thereof, in high yield and purity.
    Type: Application
    Filed: April 19, 2011
    Publication date: June 13, 2013
    Applicant: ACTAVIS GROUP PTC EHF
    Inventors: Anil Shahaji Khile, Jayesh Patel, Nikhil Trivedi, Nitin Sharadchandra Pradhan
  • Publication number: 20120151830
    Abstract: Disclosed are polyisobutenyl alcohols and substituted polyisobuentyl alcohols of the formula: wherein n is an integer from 5 to 90, R is selected from the group consisting of hydrogen, haloalkyl, alkoxycarbonyl and substituted aryl wherein at least one substituent group of the substituted aryl is selected from cyano, nitro and alkoxycarbonyl.
    Type: Application
    Filed: December 15, 2010
    Publication date: June 21, 2012
    Inventors: RICHARD E. CHERPECK, RUTH SMOCHA
  • Publication number: 20120142934
    Abstract: A method for synthesis of secondary alcohols is provided for pharmaceutical secondary alcohol by addition of organoboronic acids with aldehydes in presence of the cobalt ion and bidentate ligands as the catalyst. In addition, an enantioselective synthesis method for secondary alcohols is also herein provided in the present invention. The present invention has advantages in using less expensive cobalt ion and commercially available chiral ligands as the catalyst, wide scope of organoboronic acids and aldehydes compatible with this catalytic reaction and achieving excellent yields and/or enantiomeric excess.
    Type: Application
    Filed: March 10, 2011
    Publication date: June 7, 2012
    Inventors: Chien-Hong CHENG, Jaganathan Karthikeyan, Pang-Chi Huang
  • Publication number: 20120035226
    Abstract: The invention relates to oxadiazole compounds of formula I. The compounds are useful e.g. in the treatment of autoimmune disorders, such as multiple sclerosis.
    Type: Application
    Filed: March 29, 2010
    Publication date: February 9, 2012
    Applicant: MERCK SERONO SA
    Inventors: Anna Quattropani, Cyril Montagne, Wolfgang Sauer, Stefano Crosignani, Agnés Bombrun
  • Patent number: 8071824
    Abstract: The present invention relates to a process for preparing alkenylnitrobenzenes and alkylanilines, which are of significance as intermediates for fungicidally active alkylanilides.
    Type: Grant
    Filed: July 12, 2007
    Date of Patent: December 6, 2011
    Assignee: Bayer CropScience AG
    Inventors: Alexander Straub, Jörg Nico Greul, Norbert Lui
  • Publication number: 20110243865
    Abstract: Disclosed is a melanin production inhibitor which has an excellent inhibitory activity on the production of melanin and is highly safe. The melanin production inhibitor comprises a compound represented by general formula (1) (excluding clotrimazole), and/or a pharmacologically acceptable salt thereof.
    Type: Application
    Filed: December 22, 2009
    Publication date: October 6, 2011
    Applicant: POLA CHEMICAL INDUSTRIES INC.
    Inventors: Kouji Yokoyama, Makoto Kimura, Masashi Tamai, Yuko Saitoh, Tomomi Kato, Yu Ikeda
  • Patent number: 7906684
    Abstract: The present invention relates to the use of compounds of the formula (I) where R stands for [lacuna] with radicals defined in the description, as antioxidants, to corresponding novel compounds and compositions, and to corresponding processes for the preparation of compounds and compositions.
    Type: Grant
    Filed: April 5, 2007
    Date of Patent: March 15, 2011
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Thomas Rudolph, Herwig Buchholz
  • Publication number: 20100292458
    Abstract: The present invention discloses novel and improved nucleosidic and nucleotidic compounds that are useful in the light-directed synthesis of oligonucleotides, as well as, methods and reagents for their preparation. These compounds are characterized by novel photolabile protective groups that are attached to either the 5?- or the 3?-hydroxyl group of a nucleoside moiety. The photolabile protective group is comprised of a 2-(2-nitrophenyl)-ethyoxycarbonyl skeleton with at least one substituent on the aromatic ring that is either an aryl, an aroyl, a heteroaryl or an alkoxycarbonyl group. The present invention includes the use of the aforementioned compounds in light-directed oligonucleotide synthesis, the respective assembly of nucleic acid microarrays and their application.
    Type: Application
    Filed: June 2, 2010
    Publication date: November 18, 2010
    Applicant: NIGU Chemie GmbH
    Inventors: Sigrid BÜHLER, Markus Ott, Wolfgang Pfleiderer
  • Patent number: 7745664
    Abstract: A process for preparing venlafaxine in a high yield as well as processes for producing venlafaxine hydrochloride of form I having a very high polymorphic purity are described.
    Type: Grant
    Filed: December 10, 2004
    Date of Patent: June 29, 2010
    Assignee: KRKA Tovarno Zdravil, d.d. Novo Mesto
    Inventor: Silvo Zupancic
  • Publication number: 20100121020
    Abstract: The invention provides 3,3?-diamino-5,5?-diphenyl-4,4?-biphenyldiol which is useful as a monomer for a high-performance polymer, particularly a polymer satisfying performances highly required in the semiconductor field such as polybenzoxazole, polyimide or the like and 3,3?-dinitro-5,5?-diphenyl-4,4?-biphenyldiol as a raw material thereof. Also, the invention provides a polybenzoxazole having a repeating unit represented by the following formula (1): (wherein R is a bivalent dicarboxylic acid residue).
    Type: Application
    Filed: March 18, 2008
    Publication date: May 13, 2010
    Applicant: NIPPONKAYAKU KABUSHIKIKAISHA
    Inventors: Kenji Kunikata, Taihei Koumoto, Kenji Sekine
  • Publication number: 20100075999
    Abstract: The invention relates to a process for the preparation of anagrelide, and for the preparation of intermediates for use in preparing anagrelide. The invention also relates to the intermediates per se, in particular compounds of Formula (V): where R constitutes a suitable leaving group, which may not be hydrogen. The R group may be selected from: (i) —SiR13, (ii) —CH2Ar, (iii) —COOR2, and (iv) sulfonates such as —SO2R3.
    Type: Application
    Filed: February 6, 2008
    Publication date: March 25, 2010
    Applicant: CIPLA LIMITED
    Inventors: Srinivas Laxminarayan Pathi, Rajendra Narayanrao Kankan, Dharmaraj Ramachandra Rao
  • Patent number: 7678792
    Abstract: The invention provides compounds and pharmaceutical compositions thereof, which are useful as protein kinase inhibitors, as well as methods for using such compounds to treat, ameliorate or prevent a condition associated with abnormal or deregulated kinase activity. In some embodiments, the invention provides methods for using such compounds to treat, ameliorate or prevent diseases or disorders that involve abnormal activation of c-kit, PDGFR?, PDGFR?, CSF1R, Abl, BCR-Abl, CSK, JNK1, JNK2, p38, p70S6K, TGF?, SRC, EGFR, trkB, FGFR3, FLT3, Fes, Lck, Syk, RAF, MKK4, MKK6, SAPK2?, BRK, KDR, c-raf or b-raf kinase, or mutant forms thereof.
    Type: Grant
    Filed: October 16, 2007
    Date of Patent: March 16, 2010
    Assignee: IRM LLC
    Inventors: Donatella Chianelli, Christopher Cow, Yun He, Songchun Jiang, Xiaolin Li, Xiaodong Liu, Zuosheng Liu, Jon Loren, Valentina Molteni, Juliet Nabakka, Pingda Ren, Taebo Sim, Xiaodong Wang, Shuli You
  • Patent number: 7432399
    Abstract: A polyol monomer comprising the formula: R1 and R3 are —H, aliphatic, aromatic, or ether; R2 is aliphatic, aromatic, ester, ether, or acrylic, and R1 contains a hydroxyl group, R3 contains a hydroxyl group, R2 contains —O—CH2—CH(OH)—, or any combination thereof. The polyol monomer may be made by reacting an epoxy and an amine. Either the epoxy contains more than one epoxide groups, the amine contains a hydroxyl group, or both. A thermoset made by reacting the polyol monomer with a polyisocyanate.
    Type: Grant
    Filed: November 2, 2004
    Date of Patent: October 7, 2008
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Jozef Verborgt, Arthur Anthony Webb
  • Publication number: 20080177110
    Abstract: Provides are intermediates and processes for preparation of o-desmethylvenlafaxine.
    Type: Application
    Filed: July 26, 2007
    Publication date: July 24, 2008
    Inventors: Valerie Niddam-Hildesheim, Tamar Nidam
  • Patent number: 7183443
    Abstract: Process for the preparation of enantiomerically enriched amino aldehydes and amino alcohols, wherein a corresponding enantiomerically enriched amino nitrile is subjected to hydrogenation in the presence of hydrogen, a hydrogenation catalyst, preferably a Pd-catalyst and a mineral acid. For the preparation of an amino aldehyde hydrogen preferably is present at a hydrogen-pressure between 0.1 and 2 MPa, in particular between 0.5 and 1 MPa. The amino aldehyde preferably is isolated in the form of a chemically and configurationally stable derivative. For the preparation of an amino alcohol, preferably at least during part of the hydrogenation hydrogen is present at a hydrogen-pressure between 2 and 10 MPa, in particular between 4 and 6 MPa. In a preferred embodiment the hydrogen-pressure initially is between 0.5 and 2 MPa and subsequently, after most of the nitrile starting material is converted, the hydrogen pressure is increased to a value between 2 and 10 MPa.
    Type: Grant
    Filed: April 7, 2003
    Date of Patent: February 27, 2007
    Assignee: DSM IP Assets B.V.
    Inventors: Bernardus Henricus Nicolaas Dassen, Bernardus Kaptein, Quirinus Bernardus Broxterman
  • Patent number: 7166337
    Abstract: The present invention relates to liquid-crystal mixtures having specific resistance values, comprising acidic compounds. The present invention furthermore relates to liquid-crystal displays containing these liquid-crystal mixtures. The invention furthermore relates to compounds of the formula I, in which the parameters are as defined in the text, to their preparation, and to their use for achieving certain specific resistance values in liquid-crystal mixtures. The application also relates to a method of adjusting the specific resistance of liquid-crystal mixtures using acidic compounds.
    Type: Grant
    Filed: July 19, 2001
    Date of Patent: January 23, 2007
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Michael Darius, Volker Reiffenrath, Kazuaki Tarumi, Bernhard Rieger, Michael Heckmeier, Marcus Reuter, Peer Kirsch
  • Patent number: 7091292
    Abstract: Ligands, compositions, metal-ligand complexes and arrays with substituted bridged bis-biaromatic ligands, and methods of making and using the same, are disclosed that are useful in the catalysis of transformations such as the polymerization of monomers into polymers. The catalysts have high performance characteristics, including higher comonomer incorporation into ethylene/olefin copolymers, where such olefins are for example, 1-octene, propylene or styrene. The catalysts also polymerize propylene into isotactic polypropylene.
    Type: Grant
    Filed: April 28, 2005
    Date of Patent: August 15, 2006
    Assignee: Symyx Technologies, Inc.
    Inventors: Thomas Boussie, Oliver Bruemmer, Gary M. Diamond, Anne M. LaPointe, Margarete K. Leclerc, Cynthia Micklatcher, Pu Sun, Xiaohong Bei
  • Patent number: 6977315
    Abstract: The present invention relates to a process for producing optically active ?-nitroalcohols wherein nitroaldol reactions of aldehydes and nitroalkanes are carried out in the presence of a base and an optically active metal complex catalyst represented by the following formula (c): (where R4, R5, and R6 represent a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, an acyl group, an alkoxycarbonyl group, or an aryloxycarbonyl group, and R5 and R6 may be linked together to form a ring; X* represents a hydrocarbon group having an asymmetric carbon atom or axial asymmetry; M represents a cobalt ion or a chromium ion; and Y represents an anion capable of forming a salt when the valence of M is larger than that of a ligand).
    Type: Grant
    Filed: November 2, 2004
    Date of Patent: December 20, 2005
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Tohru Yamada, Taketo Ikeno
  • Patent number: 6943257
    Abstract: The present invention provides a process for preparing an aromatic bromide or aromatic iodide from an aromatic amine derivative using nitrite anion and halodimethylsulfonium halide generated in situ from hydrobromic acid/DMSO or hydriodic acid/DMSO. The process for producing compounds of the formula (1) is disclosed (1) wherein X is bromine or iodine: Y is carbon or nitrogen; R1, R2, R3, R4 and R5 which may be the same or different and are selected independently from the group consisting of a hydrogen, a hologen, a C1-C8 alkyl, a C1-C10 alkoxy, a nitro, a formyl, an aryl, a benzyl, a C2-C10 alkylcarbonyl and an arylcarbonyl, provided that adjacent groups as selected from R1, R2, R3, R4 and R5 may combine to form a ring.
    Type: Grant
    Filed: September 21, 2001
    Date of Patent: September 13, 2005
    Inventors: Woon Phil Baik, Jung Min Kim, Young Sam Kim, Cheol Hun Yoon, Shin Jong Kim, Seok Woo Lee
  • Patent number: 6924400
    Abstract: The invention relates, as novel and useful industrial products, to triaromatic compounds, which are vitamin D analogues, of general formula (I): and also to a method for preparing them and to their use in pharmaceutical compositions intended for use in human or veterinary medicine, or alternatively in cosmetic compositions.
    Type: Grant
    Filed: December 10, 2002
    Date of Patent: August 2, 2005
    Assignee: Galderma Research & Development, SNC
    Inventors: Jean-Michel Bernardon, Thibaud Biadatti
  • Patent number: 6849767
    Abstract: A method of hydroborating an alkene or alkyne, or reducing an organic functionality, oxidizing primary and secondary alcohols using a fluorous borane-sulfide is disclosed. The method includes regeneration and recycling the fluorous borane-sulfide.
    Type: Grant
    Filed: July 24, 2003
    Date of Patent: February 1, 2005
    Assignee: The Board of Trustees of the University of Illinois
    Inventors: David C. Crich, Santhosh Neelamkavil
  • Patent number: 6815443
    Abstract: The invention relates to 5-amino-1-pentene-3-ol substituted derivatives, a method for the production thereof, medicaments containing said compounds, the use of substituted 5-amino-1-pentene-3-ol derivatives for the production of medicaments, and methods of treatment using the medicaments.
    Type: Grant
    Filed: March 31, 2003
    Date of Patent: November 9, 2004
    Assignee: Gruenenthal GmbH
    Inventors: Helmut Buschmann, Corinna Maul, Bernd Sundermann, Utz-Peter Jagusch, Michael Haurand, Boris Chizh
  • Publication number: 20040214887
    Abstract: The present invention relates to novel dihydroxyl compounds, compositions comprising hydroxyl compounds, and methods useful for treating and preventing a variety of diseases and conditions such as, but not limited to aging, Alzheimer's Disease, cancer, cardiovascular disease, diabetic nephropathy, diabetic retinopathy, a disorder of glucose metabolism, dyslipidemia, dyslipoproteinemia, hypertension, impotence, inflammation, insulin resistance, lipid elimination in bile, obesity, oxysterol elimination in bile, pancreatitis, Parkinson's disease, a peroxisome proliferator activated receptor-associated disorder, phospholipid elimination in bile, renal disease, septicemia, metabolic syndrome disorders (e.g., Syndrome X), thrombotic disorder. Compounds and methods of the invention can also be used to modulate C reactive protein or enhance bile production in a patient.
    Type: Application
    Filed: December 23, 2003
    Publication date: October 28, 2004
    Inventors: Jean-Louis Henri Dasseux, Carmen Daniela Oniciu
  • Publication number: 20030225289
    Abstract: A process for the preparation of tricyclic amino alcohol derivatives including 2-[N-[2-(9H-carbazol-2-yloxy)ethyl]]amino-1-[(3-methylsulfonylamino)phenyl]ethanol useful in the treatment of diabetes, obesity, hyperlipidemia and so on; and intermediates as represented by formula (5) or (6) or the like useful in the preparation, wherein R11 is hydrogen or the like; and *1 represents an asymmetric carbon atom. 2-Halo-1-(3-nitrophenyl)ethanone derivatives and 1-(3-nitrophenyl)oxirane derivatives, which are intermediates for the preparation of tricyclic amino alcohol derivatives, are easy of purification, and particularly optically active 1-(3-nitrophenyl)oxirane derivatives are effective in enhancing the optical purities of the final products.
    Type: Application
    Filed: June 11, 2003
    Publication date: December 4, 2003
    Applicant: ASAHI KASEI KABUSHIKI KAISHA
    Inventors: Koki Matsubara, Naoyuki Ishii, Masami Ogawa
  • Patent number: 6610889
    Abstract: Methods and compositions are provided for the direct catalytic asymmetric aldol reaction of aldehydes with donor molecules selected from ketones and nitroalkyl compounds. The reactions employ as catalyst a Group 2A or Group 2B metal complex of a ligand of formula I, as defined further herein.
    Type: Grant
    Filed: October 31, 2001
    Date of Patent: August 26, 2003
    Assignee: The Board of Trustees of the Leland Stanford Junior University
    Inventors: Barry M. Trost, Hisanaka Ito
  • Publication number: 20020193447
    Abstract: Optically active 1-substituted phenyl-2-nitro alcohol derivatives having the formula (1) 1
    Type: Application
    Filed: July 5, 2002
    Publication date: December 19, 2002
    Inventors: Masakatsu Shibasaki, Hiroaki Sasai, Yasuo Urata, Mamoru Fujita
  • Patent number: 6476277
    Abstract: The present invention relates to a process for preparing hydroxyaromatics by oxidizing aromatics with dinitrogen monoxide in the gas phase in the presence of nanocrystalline zeolites.
    Type: Grant
    Filed: July 24, 2001
    Date of Patent: November 5, 2002
    Assignee: Bayer Aktiengesellschafter
    Inventors: Bernd Vogel, Elias Klemm, Mathias Seitz, Jochen Heller, Jörg Reiser
  • Patent number: 6462241
    Abstract: A process for preparing a compound having PGD2 antagonism represented by the formula (I), or a pharmaceutically acceptable salt or hydrate thereof, which process comprises reacting an amino alcohol of the formula (II) or its salt with a compound of the formula (III) or its reactive derivative, oxidizing the product with halo oxoacid in the presence of 2,2,6,6-tetramethylpiperidine-1-oxyls, reacting the product with an ylide under the conditions for Wittig reaction, and optionally deprotecting the product.
    Type: Grant
    Filed: April 29, 2002
    Date of Patent: October 8, 2002
    Assignee: Shionogi & Co., Ltd.
    Inventors: Tetsuo Okada, Makoto Kakinuma
  • Patent number: 6455741
    Abstract: A process for preparing a compound having PGD2 antagonism represented by the formula (I), or a pharmaceutically acceptable salt or hydrate thereof, which process comprises reacting an amino alcohol of the formula (II) or its salt with a compound of the formula (III) or its reactive derivative, oxidizing the product with halo oxoacid in the presence of 2,2,6,6-tetramethylpiperidine-1-oxyls, reacting the product with an ylide under the conditions for Wittig reaction, and optionally deprotecting the product.
    Type: Grant
    Filed: April 29, 2002
    Date of Patent: September 24, 2002
    Assignee: Shionogi & Co., Ltd.
    Inventors: Tetsuo Okada, Makoto Kakinuma
  • Patent number: 6310060
    Abstract: Phenylamino benzoic acid, benzamides, and benzyl alcohol derivatives of the formula where R1, R2, R3, R4, R5, and R6 are hydrogen or substituent groups such as alkyl, and where R7 is hydrogen or an organic radical, and Z is COOR7, tetrazolyl, CONR6R7, or CH2OR7, are potent inhibitors of MEK and, as such, are effective in treating cancer and other proliferative diseases such as inflammation, psoriasis and restenosis, as well as stroke, heart failure, and immunodeficiency disorders.
    Type: Grant
    Filed: January 5, 2000
    Date of Patent: October 30, 2001
    Assignee: Warner-Lambert Company
    Inventors: Stephen Douglas Barrett, Alexander James Bridges, Donna Reynolds Cody, Annette Marian Doherty, David Thomas Dudley, Alan Robert Saltiel, Mel Conrad Schroeder, Haile Tecle
  • Patent number: 6288242
    Abstract: The invention relates to processes for preparing a compound of the formula and the enantiomer of said compound, wherein the benzoic acid moiety is attached at position 6 or 7 of the chroman ring, and R1, R2, and R3 are as defined herein. The invention further relates to intermediates that are useful in the preparation of the compound of formula X above.
    Type: Grant
    Filed: February 23, 2000
    Date of Patent: September 11, 2001
    Assignee: Pfizer Inc.
    Inventors: Anthony Piscopio, Joel M. Hawkins, Stephanie Caron, Sarah E. Kelly, Jeffrey W. Raggon, Michael J. Castaldi, Robert W. Dugger, Sally G. Ruggeri
  • Patent number: 6255522
    Abstract: The present invention has its objects to provide a method for reducing &agr;-aminoketone derivatives under mild conditions with high stereoselectivity.
    Type: Grant
    Filed: September 29, 1999
    Date of Patent: July 3, 2001
    Assignee: Kaneka Corporation
    Inventors: Kazuhiko Matsuo, Shingo Matsumoto, Kenji Inoue
  • Patent number: 6207865
    Abstract: A carbonyl compound or a mixture of two or more carbonyl compounds is catalytically hydrogenated in the presence of a Raney copper catalyst in the form of nuggets.
    Type: Grant
    Filed: January 11, 2000
    Date of Patent: March 27, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Boris Breitscheidel, Marc Walter, Detlef Kratz, Gerhard Schulz, Manfred Sauerwald
  • Patent number: 6147224
    Abstract: Compounds of Formula 1, Formula 2 or Formula 3 where X is O, S, or (CR.sub.1 R.sub.1).sub.n where n is 0, 1 or 2; Y is a bivalent radical having Formula 4 or Formula 5 where o is an integer from 1 to 4 ##STR1## or Y is a bivalent aryl or 5 or 6 membered heteroaryl radical having 1 to 3 heteroatoms selected from N, S and O, said aryl or heteroaryl groups being unsubstituted, or substituted with 1 to 3 C.sub.1-6 alkyl or with 1 to 3 C.sub.1-6 fluoroalkyl groups; and the remaining symbols have the meaning described in the specification, have RXR selective retinoid agonist-like activity.
    Type: Grant
    Filed: October 1, 1998
    Date of Patent: November 14, 2000
    Assignee: Allergan Sales, Inc.
    Inventors: Vidyasagar Vuligonda, Kwok Yin Tsang, Jayasree Vasudevan, Roshantha A. Chandraratna
  • Patent number: 6057482
    Abstract: Benzyl alcohol of high purity is produced by supplying benzyl acetate, water and acetic acid to a hydrolysis reactor packed with a solid acid catalyst. The liquid reaction mixture produced, which contains benzyl acetate, water, benzyl alcohol and acetic acid, is supplied to an acetic acid-water recovery column, Benzyl alcohol and benzyl acetate are recovered while acetic acid is removed and returned to the hydrolysis reactor.
    Type: Grant
    Filed: November 9, 1998
    Date of Patent: May 2, 2000
    Assignee: Tosoh Corporation
    Inventors: Takashi Okada, Makoto Hanaya, Akitaka Hattori, Takanori Miyake, Nobuo Nagira, Shunya Ikumi, Takashi Hori, Norimasa Mizui
  • Patent number: 6037505
    Abstract: The anantoselective borane reduction of prochiral ketones to optically pure alcohols is effectively achieved by performing the reduction in the precence of catalytic amounts of the new and valuable oxazaborolidine compounds of formulas (I) and (II). The compounds of formulas (I) and (II) may be isolated and purified prior to use in the reduction reactions or the compounds of formulas (I) and (II) may be generated in situ.
    Type: Grant
    Filed: April 26, 1999
    Date of Patent: March 14, 2000
    Assignee: Pfizer Inc.
    Inventor: George Joseph Quallich
  • Patent number: 5994558
    Abstract: The invention provides methods for preparing a 2-isoxazoline compound represented by formula (1) and a 2,5-diamino-1,6-diphenyl-3-hydroxyhexane compound obtainable by reducing the 2-isoxazoline compound and represented by formula (6): ##STR1## wherein Ph is phenyl; and each of R.sup.1 and R.sup.2 independently represents hydrogen, acyl, alkyloxycarbonyl, arylalkyloxycarbonyl, aryloxycarbonyl, alkylaminocarbonyl, arylalkylaminocarbonyl, arylaminocarbonyl, alkyl, arylalkyl, aryl, alkylsulfonyl, acylalkylsulfonyl, or arylsulfonyl, or R.sup.1 and R.sup.2 are linked to each other to form divalent acyl. These compounds are useful as intermediates in the synthesis of medicines such as retrovirus protease inhibitors including human immunodeficiency virus (HIV) protease inhibitors.
    Type: Grant
    Filed: November 24, 1997
    Date of Patent: November 30, 1999
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yoshiyuki Murai, Masahiro Nishikawa, Yoichiro Ueda, Ichiro Takase
  • Patent number: 5895824
    Abstract: In a process for preparing polyether polyols containing aromatics by molecular addition of alkylene oxides to H-functional initiators at from 70.degree. C. to 135.degree. C. and pressures of from 0.1 MPa to 1.0 MPa, the alkoxylation is carried out using at least one initiator comprising at least 95% by weight of 2,3 and 3,4 isomers of tolylenediamine, from 0.5 to 4% by weight of 2,4 and 2,6 isomers of tolylenediamine and from 0.1 to 1.5% by weight of more volatile fractions from tolylenediamine production. The polyether polyols prepared by this process can be used as component of a polyol mixture for producing rigid polyurethane foams.
    Type: Grant
    Filed: June 7, 1996
    Date of Patent: April 20, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Stefan Dinsch, Regina Pretzsch, Juergen Winkler, Bernd Guettes, Karl-Heinz Steinchen
  • Patent number: 5874647
    Abstract: A zeolite catalyst for hydroxylating benzene to phenol is treated hydrothermally with a gas comprising approximately 1-100 mole percent water at a temperature between approximately 350.degree.-950.degree. C., and subsequently is treated with an acid. This treatment selectively removes aluminum species from the zeolite catalyst in a manner that increases catalyst stability in phenol production without reducing the activity of the catalyst.
    Type: Grant
    Filed: August 20, 1996
    Date of Patent: February 23, 1999
    Assignee: Solutia Inc.
    Inventors: William D. McGhee, Patrick P. B. Notte
  • Patent number: 5874654
    Abstract: Environmentally-polluting nitrocresol values are removed from admixtures of nitroaromatic compounds comprised thereof, notably the media of nitration of aromatic compounds by reacting same with aqueous HNO.sub.3 /H.sub.2 SO.sub.4, by first intimately contacting such nitroaromatic compound admixtures with an oxidizing agent comprising hydrogen peroxide, javelle water, or mixture thereof, and thereafter with a neutralizing agent; the nitroaromatic aromatic compounds thus purified are conveniently catalytically hydrogenated into aromatic amines.
    Type: Grant
    Filed: September 19, 1997
    Date of Patent: February 23, 1999
    Assignee: Rhone Poulenc Chimie
    Inventors: Antoinette Gacon-Camoz, Pascal Metivier
  • Patent number: 5856576
    Abstract: There are provided aryne intermediates of formula I, useful in the manufacture of herbicidal compounds. ##STR1## Also provided is a method to prepare the formula I intermediates via the palladium catalyzed coupling of an o-halonitrobenzene or o-haloaniline with 3-butyne-1-ol.
    Type: Grant
    Filed: January 29, 1998
    Date of Patent: January 5, 1999
    Assignee: American Cyanamid Company
    Inventors: Philip M. Harrington, Kenneth A. M. Kremer
  • Patent number: 5830920
    Abstract: Compounds of the formula ##STR1## wherein n.sup.1 -n.sup.9 are each independently 0 or 1;m.sup.1 -m.sup.9 are each independently 0 or 1, but with the proviso that at least one of m.sup.1, m.sup.2 and m.sup.3, at least one of m.sup.4, m.sup.5 and m.sup.6 and, when present, at least one of m.sup.7, m.sup.8 and m.sup.9 is 1; and whereinX.sup.1 -X.sup.18 each independently is --O--, --CONR.sup.1,--NR.sup.1 CO-- or --NR.sup.1 --;R.sup.1 is hydrogen or lower alkyl;W is a benzene or s-triazine;Y.sup.1 -Y.sup.9 each independently is an aromatic ring systems;A.sup.1 -A.sup.3 each independently is a residue of a sugar alcohol devoid of the 1-hydroxy group or a derivative thereof, a residue of a sugar acid devoid of the 1-carboxy group or a derivative thereof or tris-(hydroxymethyl)-methyl;D is the di-residue of a sugar alcohol devoid of 2 hydroxy groups or a derivative thereof or the di-residue of a sugar dicarboxylic acid devoid of 2 carboxy group or a derivative thereof;Q.sup.1 -Q.sup.3 and Z.sup.
    Type: Grant
    Filed: April 26, 1996
    Date of Patent: November 3, 1998
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Alexander Chucholowski, Jurgen Fingerle, Niggi Iberg, Hans Peter Marki, Rita Muller, Michael Pech, Marianne Rouge, Gerard Schmid, Thomas Tschopp, Hans Peter Wessel
  • Patent number: 5750802
    Abstract: A 1-phenyl-2-nitroalcohol of the formula I ##STR1## having a (1R*,2S*) stereoisomer and a (1R*2R*) stereoisomer is produced by reacting benzaldehyde with a nitroalkane in the presence of an amine catalyst. The resulting 1-phenyl-2-nitroalcohol includes at least 50% of the (1R*,2S*) stereoisomer.
    Type: Grant
    Filed: July 31, 1997
    Date of Patent: May 12, 1998
    Assignee: Amvac Chemical Corporation
    Inventor: C. Edward Baxter, Jr.
  • Patent number: 5600035
    Abstract: Photoreactive compounds are synthesized from 2,5- or 2,6-dintrobenzyl groups. Also disclosed are methods of synthesizing reactive monomers containing 2,5- or 2,6-dintrobenzyl groups.
    Type: Grant
    Filed: July 13, 1994
    Date of Patent: February 4, 1997
    Assignee: PPG Industries, Inc.
    Inventors: Charles F. Kahle, II, Neil D. McMurdie, Raphael O. Kollah, Daniel E. Rardon, Gregory J. McCollum
  • Patent number: 5523457
    Abstract: This invention relates to a retinoid mpound of formula I ##STR1## in which Y is --CO--NH--, --CR.sup.2 .dbd.CR.sup.3 --, --CO--O--, --O--CO--, --C(.dbd.S)--NH--, --C.tbd.C--, --O--CH.sub.2 --, --CH.sub.2 --O--, or --CH.sub.2 --CH.sub.2 --;A is --(CH.sub.2).sub.t -- or a bond;Q is phenyl optionally substituted with one to three same or different C.sub.1-6 alkyl, C.sub.1-6 alkoxy, halogen, or --CO.sub.2 R.sup.4 ;R.sup.1 is --CO.sub.2 Z, --CONHR.sup.5, C.sub.1-6 alkyl, --CH.sub.2 OH, or --CHO;R.sup.2, R.sup.3, R.sup.4, R.sup.5, and Z are independently hydrogen or C.sub.1-6 alkyl;t is one to six.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: June 4, 1996
    Assignee: Bristol-Myers Squibb Company
    Inventors: John E. Starrett, Jr., Muzammil M. Mansuri, David R. Tortolani
  • Patent number: 5492917
    Abstract: Novel compounds of the general structural formula I: ##STR1## have endothelin antagonist activity and are therefore useful in treating cardiovascular disorders, such as hypertension, pulmonary hypertension, postischemic renal failure, vasospasm, cerebral and cardiac ischemia, myocardial infarction, endotoxic shock, inflammatory diseases including Raynaud's disease and asthma.
    Type: Grant
    Filed: September 29, 1993
    Date of Patent: February 20, 1996
    Assignee: Merck & Co., Inc.
    Inventors: Ralph A. Rivero, Peter D. Williams, Daniel F. Veber