The Chain Nitrogen Bonded Directly To The Benzene Ring Patents (Class 558/394)
  • Patent number: 10905120
    Abstract: The present invention provides agonist compounds that activate ABA receptors, agricultural formulations comprising the agonist compounds, and methods of use for the compounds and formulations. The agricultural formulations are useful for inducing ABA responses in plant vegetative tissues, reducing abiotic stress in plants, and inhibiting germination of plant seeds. The compounds are also useful for inducing expression of ABA-responsive genes in cells that express endogenous or heterologous ABA receptors.
    Type: Grant
    Filed: November 28, 2017
    Date of Patent: February 2, 2021
    Assignee: The Regents of the University of California
    Inventors: Sean R. Cutler, Aditya Vaidya
  • Patent number: 9926291
    Abstract: A novel synthesis of the anti-androgen, A52, which has been found to be useful in the treatment of prostate cancer, is provided. A52 as well as structurally related analogs may be prepared via the inventive route. This new synthetic scheme may be used to prepare kilogram scale quantities of pure A52.
    Type: Grant
    Filed: December 6, 2016
    Date of Patent: March 27, 2018
    Assignee: Sloan-Kettering Institute for Cancer Research
    Inventors: Ouathek Ouerfelli, Anna Dilhas, Guangbin Yang, Hong Zhao
  • Patent number: 9512103
    Abstract: A novel synthesis of the anti-androgen, A52, which has been found to be useful in the treatment of prostate cancer, is provided. A52 as well as structurally related analogs may be prepared via the inventive route. This new synthetic scheme may be used to prepare kilogram scale quantities of pure A52.
    Type: Grant
    Filed: March 24, 2015
    Date of Patent: December 6, 2016
    Assignee: Sloan-Kettering Institute for Cancer Research
    Inventors: Ouathek Ouerfelli, Anna Dilhas, Guangbin Yang, Hong Zhao
  • Patent number: 9161535
    Abstract: The present invention generally relates to color stable formulations containing the potassium salt of (S)-(+)-abscisic acid, the color stabilizers sodium citrate and sodium acetate, the antimicrobial agent potassium sorbate, and do not contain an acrylic copolymer surfactant. The present invention is also directed to methods for using the present formulations in organic farming.
    Type: Grant
    Filed: July 21, 2014
    Date of Patent: October 20, 2015
    Assignee: Valent BioSciences Corporation
    Inventors: Bala N. Devisetty, John Lopez, Daniel F. Heiman, Peter D. Petracek, Xiaozhong Liu, Derek D. Woolard, Gregory D. Venburg, Yueh Wang, Prem Warrior
  • Publication number: 20120028249
    Abstract: Disclosed are near IR emitting fluorescent compounds; methods of making and kits containing the described compounds; and their use in fluorescence-based detection of biological materials.
    Type: Application
    Filed: October 20, 2009
    Publication date: February 2, 2012
    Applicant: LIFE TECHNOLOGIES CORPORATION
    Inventors: Stephen Yue, Shih-Jung Huang, Jolene Bradford
  • Patent number: 7964754
    Abstract: Disclosed are a diimmonium salt and a near infrared ray absorption film including the same which is used for blocking the near infrared ray. The diimmonium salt for a near infrared ray absorption film is represented by Formula 1 of the specification, wherein, n is an integer of 1 or 2, R1 to R8 are independently a substituted or unsubstituted linear or branched C1-C10 alkyl group, the substituent for the alkyl group is selected from the group consisting of a cyano group, a nitro group, a carboxyl group, a sulfone group, a halogen atom, a hydroxyl group, a C1 -C8 alkoxy, alkoxyalkoxy, acyloxy, or alkylamino group, and C6-C18 aryl or aryloxy group, and X is a substituted fluoro alkyl phosphate anion represented by Formula 2 of the specification, wherein, x is an integer of 0 or 1, y is an integer of 1, 2 or 3, z is an integer of 6-y, and R9 to R13 are independently a hydrogen atom (H) or a fluorine atom (F).
    Type: Grant
    Filed: September 5, 2007
    Date of Patent: June 21, 2011
    Assignee: SK Chemicals Co., Ltd.
    Inventors: Min-Hyuk Lee, Ju-Sik Kang, Jeong-Ho Park, Sung-Yung Lee
  • Publication number: 20100279340
    Abstract: Charged and neutral small fluorescent molecules based upon the styryl scaffold are useful as imaging agents for misfolded proteins such as amyloid plaque. Charged molecules are prepared using pyrrolidine catalyzed reactions by solution-phase synthesis. Neutral styryl molecules are prepared using acetic anhydride catalyzed reactions, Horner-Emmons reactions or Wittig reactions.
    Type: Application
    Filed: February 11, 2008
    Publication date: November 4, 2010
    Applicant: NYU
    Inventors: Thomas Wisniewski, Jaeki Min, Qian Li, Young-Tae CHANG
  • Publication number: 20100113449
    Abstract: The present invention relates to compounds that are sodium channel inhibitors and to their use in the treatment of various disease states, including cardiovascular diseases and diabetes. In particular embodiments, the structure of the compounds is given by Formula (IA) or (IB): as further described herein. The invention also relates to methods for the preparation of the compounds, and to pharmaceutical compositions containing such compounds.
    Type: Application
    Filed: October 28, 2009
    Publication date: May 6, 2010
    Applicant: Gilead Palo Alto, Inc.
    Inventors: Matthew Abelman, Elfatih Elzein, Robert Jiang, Rao Kalla, Tetsuya Kobayashi, Xiaofen Li, Thao Perry, Jeff Zablocki
  • Publication number: 20090143454
    Abstract: The present invention relates to novel pyrazoline derivatives of the formula (I) in which R1, R2, R3 and R4 are as defined in the disclosure, to a plurality of processes for preparing these substances, and to their use for controlling pests, and further relates to novel intermediates and processes for their preparation.
    Type: Application
    Filed: July 8, 2002
    Publication date: June 4, 2009
    Applicant: BAYER CROPSCIENCE AG
    Inventors: Fritz Maurer, Rainer Fuchs, Christoph Erdelen, Angelika Lubos-Erdelen, Udo Reckmann, Andreas Turberg
  • Publication number: 20090023942
    Abstract: The invention relates to a method for producing bifunctional ammonium nitriles by reacting a dihalogenalkyl compound or a dihalogenaryl compound with a dialkylaminoacetonitrile in a polar, aprotic solvent. Bifunctional ammonium nitriles may be used as bleach activators in detergents and cleaners.
    Type: Application
    Filed: February 24, 2006
    Publication date: January 22, 2009
    Applicant: CLARIANT PRODUKTE (DEUTSCHALND) GMBH
    Inventors: Gerd Reinhardt, Lars Cuypers
  • Publication number: 20080275114
    Abstract: Compounds of formula (I), in which R1 and R2 are independently a substituted phenyl group, where the substituents are as defined in the claims and with the proviso that at least one of the substituents is a cyano, carboxy or (C1-4)alkoxycarbonyl group, are inhibitors of CCR9 activity useful for therapeutic treatment, particularly of irritable bowel disease.
    Type: Application
    Filed: December 22, 2006
    Publication date: November 6, 2008
    Inventors: Jose M. Carballido Herrera, Herbert Jaksche, Philipp Lehr, Gudrun Werner, Anthony Winiski
  • Patent number: 7323574
    Abstract: A process for the preparation of compound (III) which comprises the reaction between a compound of general formula (V) and dicyano acetylene (IV), said reaction carried out in the presence of water wherein R is selected from CF3, or C1 to C6 alkyl M is an alkaline or alkaline-earth metal or silver.
    Type: Grant
    Filed: September 28, 2006
    Date of Patent: January 29, 2008
    Assignee: BASF Agro B.V. Arnhem
    Inventors: Jean-Erick Ancel, Joelle Vidal
  • Patent number: 7049337
    Abstract: Aminotetralin derivatives and pharmacological analogs thereof which contain an N-propynyl group exhibit differential dopaminergenic receptor activity. The subject compounds are useful in affecting dopamine receptor activity, particularly in exhibiting differing activity among the various dopamine receptor subtypes. The compounds are useful in treating CNS disorders in mammals in general, and humans in particular.
    Type: Grant
    Filed: May 17, 2001
    Date of Patent: May 23, 2006
    Assignee: Wayne State University
    Inventor: Aloke K. Dutta
  • Patent number: 6759503
    Abstract: The invention provides N-cyanoethylated toluenediamines (CNTDAs), processes for synthesizing them, and compositions containing them. In preferred embodiments, the CNTDAs are represented by the following formula: where the nitrogen atoms are ortho or meta to each other on the aromatic ring. The CNTDAs are particularly suitable for use as latent curing agents for epoxy resins.
    Type: Grant
    Filed: January 31, 2003
    Date of Patent: July 6, 2004
    Assignee: Air Products and Chemicals, Inc.
    Inventors: William Edward Starner, Tammy Lynn Cush
  • Publication number: 20040072371
    Abstract: Compositions useful for labeling &bgr;-amyloid plaques and neurofibrillary tangles are provided.
    Type: Application
    Filed: October 7, 2003
    Publication date: April 15, 2004
    Inventors: Jorge R. Barrio, Andrej Petric, Nagichettiar Satyamurthy, Gary W. Small, Gregory M. Cole, Sung-Cheng Huang
  • Patent number: 6673956
    Abstract: The present invention relates to processes for the preparation of a compound of the formula wherein W is nitrogen or —CR3; R1 is halogen, haloalkyl, haloalkoxy, R4S(O)n— or —SF5; R2 is hydrogen; R3 is halogen; R4 is alkyl or haloalkyl; and n is 0, 1 or 2.
    Type: Grant
    Filed: April 12, 2002
    Date of Patent: January 6, 2004
    Assignee: Aventis Agriculture Ltd.
    Inventor: Jean-Erick Ancel
  • Patent number: 6620933
    Abstract: A azomethine yellow dye compound of general formula (I): General formula (I) wherein R1 and R2 each independently represent a hydrogen atom or a substituent; R3 represents a substituent; m indicates an integer from 0 to 3; when m is 2 or greater, R3's may be the same or different and may be mutually bonded to form a condensed ring; R3 may be bonded to R1 or R2 to form a condensed ring; R4 represents an aryl group or a heterocyclic group; R5 and R6 each independently represent a hydrogen atom or a substituent; R7 represents a substituent; n indicates an integer from 0 to 4; when n is 2 or greater, R7's may be the same or different and the may be mutually bonded to form a condensed ring; R7 may be bonded to R5 or R6 to form a condensed ring; and R5 and R6 may be bonded to each other to form a ring.
    Type: Grant
    Filed: September 26, 2002
    Date of Patent: September 16, 2003
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kiyoshi Takeuchi, Shigeki Uehira
  • Patent number: 6593487
    Abstract: The invention provides N-cyanoethylated toluenediamines (CNTDAs), processes for synthesizing them, and compositions containing them. In preferred embodiments, the CNTDAs are represented by the following formula: where the nitrogen atoms are ortho or meta to each other on the aromatic ring. The CNTDAs are particularly suitable for use as latent curing agents for epoxy resins.
    Type: Grant
    Filed: December 19, 2001
    Date of Patent: July 15, 2003
    Assignee: Air Products and Chemicals, Inc.
    Inventors: William Edward Starner, Tammy Lynn Cush
  • Patent number: 6586617
    Abstract: The present invention relates to microbicides for agricultural or horticultural use containing a sulfonamide derivative.
    Type: Grant
    Filed: December 18, 2001
    Date of Patent: July 1, 2003
    Assignee: Sumitomo Chemical Takeda Agro Company, Limited
    Inventors: Takanori Tabuchi, Tetsuhiro Yamamoto, Masaharu Nakayama
  • Patent number: 6548694
    Abstract: N-(4-carbamimidoyl-phenyl)-glycine derivatives have the formula: wherein X and R1 to R5 are as defined herein, and includes hydrates or solvates and/or physiologically acceptable salts thereof and/or physiologically acceptable esters thereof.
    Type: Grant
    Filed: May 16, 2001
    Date of Patent: April 15, 2003
    Assignee: Hoffman-La Roche Inc.
    Inventors: Leo Alig, Katrin Groebke Zbinden, Kurt Hilpert, Holger Kuehne, Ulrike Obst, Hans Peter Wessel
  • Patent number: 6498004
    Abstract: This invention provides a photographic element comprising at least one silver halide emulsion layer in which the silver halide is sensitized with a compound of the formula (a): &Dgr;−(t)m−XY′  (a) XY′−(t)m−&Dgr;  (b) &Dgr;−(t)m−XY′−(t)m−&Dgr;  (c) wherein &Dgr; is protective group that is eliminated during development of the photographic element, t is a timing group, m is an integer from 0 to 3, and XY′ is a fragmentable electron donor moiety in which X is an electron donor group and Y′ is a leaving proton H or a leaving group Y, with the proviso that if Y′ is a proton, a base, &bgr;−, is present in the emulsion or is covalently linked directly or indirectly to X, and wherein: 1) X—Y′ has an oxidation potential between 0 and about 1.
    Type: Grant
    Filed: December 28, 2000
    Date of Patent: December 24, 2002
    Assignee: Eastman Kodak Company
    Inventors: Jerome R. Lenhard, Annabel A. Muenter, Stephen A. Godleski, Paul A. Zielinski, Deepak Shukla, Donald R. Diehl
  • Patent number: 6258973
    Abstract: The invention relates to a process for the preparation of compounds having the formula (I) wherein W, R2, R3, R5 and R6 are as defined in the description, which are useful as intermediates in the synthesis of pesticidally active compounds.
    Type: Grant
    Filed: May 17, 2000
    Date of Patent: July 10, 2001
    Assignee: Rhone-Poulenc Agro
    Inventors: Themistocles D. J. D'Silva, Jean-Erick Ancel
  • Patent number: 5965717
    Abstract: Nonmutagenic, highly twisted derivatives of benzidine of the following formula ##STR1## useful as intermediates for the preparation of various organic pigments were obtained. The benzidine derivatives are significantly rotated about the biphenyl linkage due to bulky substituents at the R.sub.2 and/or R.sub.4 positions. Bisazomethine, disaoacetoacetanilide, disazopyrazolone, disazobenzimidazolone and disazonaphthol pigments prepared from these highly twisted benzidines exhibit hypsochromic spectral shifts relative to pigments prepared from other benzidine compounds with less twist about the biphenyl linkage, for instance, other benzidine compounds in which all four R.sub.2 and R.sub.4 represent H. Greenish-yellow, yellow, orange, red and brown pigments obtained from the twisted benzidines are nonmutagenic in the standard Ames test and Prival modification.
    Type: Grant
    Filed: November 4, 1997
    Date of Patent: October 12, 1999
    Assignee: North Carolina State University
    Inventors: Harold S. Freeman, David Hinks, Jolanta Sokolowska-Gajda
  • Patent number: 5620831
    Abstract: Disclosed are novel cyanoguanidine derivatives which are usable as an epoxy resin curing agent and are represented by the following general formula (1). A thermosetting resin composition and a photocurable and thermosetting resin composition containing the following cyanoguanidine derivatives and other derivatives as the epoxy resin curing agent are also disclosed. ##STR1## wherein R.sup.1 represents a substituent selected from the group consisting of the following substituents (a) through (k).
    Type: Grant
    Filed: March 28, 1995
    Date of Patent: April 15, 1997
    Assignee: Taiyo Ink Manufacturing Co., Ltd.
    Inventor: Osamu Kawana
  • Patent number: 5559150
    Abstract: The present invention is directed to novel compounds that are non-peptidic thrombin inhibitors. The compounds have the structure: ##STR1## and pharmaceutically acceptable salts thereof; wherein R.sup.1 is one of alkyl, substituted alkyl, cycloalkyl, aryl, substituted aryl, heteroaryl or substituted heteroaryl; and n is from zero to five. The compounds of the invention are useful for the treatment of arterial and venous thrombotic occlusive disorders, inflammation, cancer, and neurodegenerative diseases.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: September 24, 1996
    Assignee: 3-Dimensional Pharmaceuticals, Inc.
    Inventor: Richard M. Soll
  • Patent number: 5496855
    Abstract: This invention relates to the novel compounds and pharmaceutical compositions of Formulas (I) and (II).This invention also relates to a method of treating or reducing inflammation in a mammal in need thereof, which comprises administering to said mammal an effective amount of a compound or composition of Formula (I) or (II).
    Type: Grant
    Filed: January 27, 1995
    Date of Patent: March 5, 1996
    Assignee: SmithKline Beecham Corp.
    Inventors: Jerry L. Adams, Ravi S. Garigipati, Margaret E. Sorenson, James D. Winkler
  • Patent number: 5493053
    Abstract: A new and versatile route to N'-[5-[[4-[[5-(acetylhydroxyamino)pentyl]amino]-1,4-dioxobutyl]hydroxyamin o]pentyl]-N-(5-aminopentyl)-N-hydroxybutanediamide, desferrioxamine B (DFO) is described. N-Benzyloxy-1,5-diaminopentane is selectively protected at the primary amino site. The product is reacted at the benzyloxyamine with an anhydride to produce a carboxylic acid which is, in turn, acylated regio-specifically with a diamine at the primary amine to give a benzyloxyamine. The previous two steps are repeated to afford a DFO reagent. Acetylation of the DFO reagent, followed by hydrogenolysis and tert-butoxycarbonyl group removal, furnishes DFO.
    Type: Grant
    Filed: December 21, 1994
    Date of Patent: February 20, 1996
    Assignee: University of Florida Research Foundation, Inc.
    Inventor: Raymond J. Bergeron, Jr.
  • Patent number: 5443820
    Abstract: Esters and amides of aminomethylenecyanoacetic acid I ##STR1## where R.sup.1 and R.sup.2 are each, independently of one another, phenyl, naphthyl, biphenylyl or five- or six-membered hetaryl with one, two or three nitrogens or one oxygen or one sulfur or one nitrogen and one oxygen or one nitrogen and one sulfur, which can be benzo-fused, it being possible for these radicals to be substituted by one to three C.sub.1 -C.sub.12 -alkyl groups, C.sub.1 -C.sub.12 -alkoxy groups, halogen atoms, cyano groups, hydroxyl groups or groups of the formulae COOR.sup.3, COR.sup.3, CONHR.sup.3, OCOR.sup.3 or NHCOR.sup.3, and whereR.sup.3 is C.sub.1 -C.sub.12 -alkyl, C.sub.5 -C.sub.8 -cycloalkyl or phenyl,X is C.sub.2 -C.sub.30 -alkylene which can be interrupted by non-adjacent oxygens, or is C.sub.4 -C.sub.12 -alkenylene or C.sub.4 -C.sub.12 -alkynylene where the unsaturated bonds are not adjacent to the ester oxygens, or is C.sub.5 -C.sub.8 -cycloalkylene or phenylene, andY is O or NH.
    Type: Grant
    Filed: January 5, 1994
    Date of Patent: August 22, 1995
    Assignee: Basf Aktiengesellschaft
    Inventors: Martin Holderbaum, Alexander Aumueller, Hubert Trauth
  • Patent number: 5420159
    Abstract: All possible stereoisomeric forms and mixtures thereof of a compound of the formula ##STR1## wherein X is selected from the group consisting of hydrogen, alkyl, alkenyl and alkynyl of up to 4 carbon atoms, --CN and aralkynyl of up to 10 carbon atoms, Y is selected from the group consisting of halogen, --CH.sub.2 F, --CHF.sub.2, and --CF.sub.3, A is selected from the group consisting of ##STR2## having pesticidal properties.
    Type: Grant
    Filed: September 26, 1994
    Date of Patent: May 30, 1995
    Assignee: Roussel-Uclaf
    Inventors: Didier Babin, Marc Benoit, Jean-Pierre Demoute
  • Patent number: 5405987
    Abstract: The present invention pertains to a method of preparing substituted and unsubstituted N-hydroxy-2-aminobutane diacid derivatives which can be dehydrated to 2-aminobut-2-ene dioic acid derivatives, which can be subsequently converted to pyridine and quinoline derivatives.
    Type: Grant
    Filed: March 28, 1991
    Date of Patent: April 11, 1995
    Assignee: Hoechst Celanese Corporation
    Inventors: Varadaraj Elango, Donald R. Larkin, John R. Fritch, Michael P. Bodman, Werner H. Mueller, Bernard F. Gupton, John C. Saukaitis
  • Patent number: 5399690
    Abstract: Solid particle dispersions of dyes according to the formula: ##STR1## wherein D is selected from the group consisting of ##STR2## and ketomethylene nuclei are disclosed as filter dyes for photographic elements.In this formula, E.sup.1 and E.sup.2 are each independently electron withdrawing groups. R.sup.1 and R.sup.6 are each independently R or NHR, where R is aryl. R.sup.2 and R.sup.3 are each independently alkyl or aryl, or represent the carbon atoms necessary to form a fused ring with the phenyl ring to which the N atom is attached. R.sup.4 and R.sup.7 are each independently hydrogen, alkyl or aryl. R.sup.5 is alkyl. Z represents the atoms necessary to complete a 5 or 6 memebered heterocyclic nucleus. M.sup.+ is a cation. L.sup.1 through L.sup.7 are each independently methine groups. m is 0, 1, 2, or 3. n is 0 or 1. p is 0, 1, 2, 3, or 4. q is 0, 1, 2, or 3. At least one of R.sup.1 or D includes an aryl ring substituted with a carboxy or sulfonamido substituent.
    Type: Grant
    Filed: February 10, 1993
    Date of Patent: March 21, 1995
    Assignee: Eastman Kodak Company
    Inventors: Donald R. Diehl, Glenn M. Brown, Margaret J. Helber
  • Patent number: 5393913
    Abstract: The present invention relates to N-carbonyl anilines which are intermediates for the preparation of pesticidal 1-aryl imidazoles and to processes for making them.
    Type: Grant
    Filed: March 3, 1993
    Date of Patent: February 28, 1995
    Assignee: Rhone-Poulenc Inc.
    Inventor: Thierry Aubert
  • Patent number: 5391804
    Abstract: A new process for the preparation of mono-N-.beta.-cyanoethylanilines, characterized in that a substituted or unsubstituted aniline compound is reacted with acrylonitrile in the presence of active bleaching earth as catalyst at a temperature of between 80.degree. and 200.degree. C. in a nonaqueous reaction medium.
    Type: Grant
    Filed: January 28, 1994
    Date of Patent: February 21, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred Blazejak, Wilfried Kohler, Karl-Johann Wemmje
  • Patent number: 5389619
    Abstract: Compounds of the formula I ##STR1## where n, W, X, Y, Z, R.sup.1, R.sup.2, and R.sup.3 are as defined herein exhibit fungicidal, insecticidal, and acaracidal activity.
    Type: Grant
    Filed: March 29, 1993
    Date of Patent: February 14, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Reinhard Doetzer, Hubert Sauter, Horst Wingert, Reinhard Kirstgen, Albrecht Harreus, Gisela Lorenz, Eberhard Ammermann
  • Patent number: 5382595
    Abstract: A butenoic or propenoic acid derivative having the following formula in which G is an aryl or a heterocyclic ring, R11 and R12 are hydroben or an alkyl, X is sulfur or oxygen, R2 and R3 are hydrogen, an substituent such as an alkyl and J is pyridyl or phenyl having substituents and a heterocyclic ring may be formed between R2, R3 and J is provided here and is useful in the pharmacological field.
    Type: Grant
    Filed: October 13, 1992
    Date of Patent: January 17, 1995
    Assignee: Eisai Co., Ltd.
    Inventors: Norio Minami, Fumihiro Ozaki, Keiji Ishibashi, Yasuhiro Kabasawa, Megumi Ikemori, Toshiaki Ogawa, Takanori Kawamura
  • Patent number: 5367095
    Abstract: Polyoxyalkylene polyamine or aromatic diamines or xylylenediamines are modified by them to the Michael reaction with an ethylenically unsaturated monomer having an electron-withdrawing group to convert the primary amino groups at least in part to a secondary amino group of the formula:--NH--CH.sub.2 --CH(R)--Ywherein R is a hydrogen atom or methyl, and Y is an electron-withdrawing group. The modified amines find use in the manufacture of plastics such as polyurea elastomers or polyurea RIM.
    Type: Grant
    Filed: September 4, 1992
    Date of Patent: November 22, 1994
    Assignee: Nippon Paint Company, Ltd.
    Inventors: Toshiyuki Ohshima, Hideo Ishibashi, Rie Tamura, Satoshi Yamamoto, Takaharu Izumo
  • Patent number: 5367113
    Abstract: Synthesis of desferrioxamine B and analogs and homologs thereof beginning with O-protected, N-protected hydroxylamine, which is N-alkylated to produce a protected N-4-cyanoalkylhydroxylamine which is acylated with a suitable anhydride. The resulting half-acid amide is subjected to a series of high yield condensations and reductions which vide desferrioxamine B in high overall yield. Alternatively, polyether analogs of desferrioxamine B can be prepared by reacting an activated polyether with the O-protected, N-protected hydroxylamine and subjecting the resulting product to a series of similar steps.
    Type: Grant
    Filed: June 23, 1993
    Date of Patent: November 22, 1994
    Assignee: University of Florida Research Foundation, Inc.
    Inventor: Raymond J. Bergeron, Jr.
  • Patent number: 5334745
    Abstract: 3-Aminopropionitriles of the general formula I ##STR1## where R.sup.1,R.sup.2,R.sup.3,R.sup.4 and R.sup.5 independently of one another are each hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.1 -C.sub.8 -aminoalkyl, C.sub.1 -C.sub.8 -cyanoalkyl, C.sub.3 -C.sub.20 -cycloalkyl, C.sub.7 -C.sub.20 -aralkyl or aryl,are prepared by a process in which an amine of the general formula II ##STR2## is reacted with an acrylonitrile of the general formula III ##STR3## where the substituents have the abovementioned meanings, in a molar ratio of from 0.9:1 to 100:1 over a heterogeneous catalyst at from 40.degree. to 200.degree. C. and from 1 to 350 bar.
    Type: Grant
    Filed: May 28, 1993
    Date of Patent: August 2, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Martin Brudermueller, Tom Witzel, Franz Merger
  • Patent number: 5254724
    Abstract: Synthesis of desferrioxamine B and analogs and homologs thereof beginning with O-protected, N-protected hydroxylamine, which is N-alkylated to produce a protected N-4-cyanoalkylhydroxylamine which is acylated with a suitable anhydride. The resulting half-acid amide is subjected to a series of high yield condensations and reductions which provide desferrioxamine B in high overall yield. Alternatively, polyether analogs of desferrioxamine B can be prepared by reacting an activated polyether with the O-protected, N-protected hydroxylamine and subjecting the resulting product to a series of similar steps.
    Type: Grant
    Filed: October 30, 1991
    Date of Patent: October 19, 1993
    Assignee: University of Florida Research Foundation, Inc.
    Inventor: Raymond J. Bergeron, Jr.
  • Patent number: 5120872
    Abstract: A compound of the formula ##STR1## in which R.sub.1 and R.sub.2 independently of one another are each C.sub.1 -C.sub.10 alkyl which is unsubstituted or substituted by hydroxyl, C.sub.1 -C.sub.4 alkoxy, phenyl, sulfo, sulfato, thiosulfato, cyano or halogen, C.sub.5 -C.sub.7 cycloalkyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, or C.sub.1 -C.sub.4 alkoxy, or phenyl or naphthyl which both are unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkanoylamino, benzoylamino, halogen or sulfo, R.sub.3 is hydrogen, halogen, C.sub.1 -C.sub.10 alkyl which is unsubstituted or substituted by hydroxyl, C.sub.1 -C.sub.4 alkoxy, phenyl, sulfo, sulfato, thiosulfato, cyano or halogen, C.sub.1 -C.sub.10 alkoxy which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkoxy, or phenoxy which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.
    Type: Grant
    Filed: December 3, 1990
    Date of Patent: June 9, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Harald Walter, Rudolf Hurter
  • Patent number: 5120869
    Abstract: A herbicidal compound of formula (I): ##STR1## wherein X is O, S(O).sub.n or NR.sup.a where R.sup.a is H or alkyl and n is 0, 1 or 2;R.sup.1 is H or halo;R.sup.2 is N or CR.sup.3 where R.sup.3 is halo or NO.sub.2 ;R.sup.4 is H, halo, NO.sub.2, alkyl, haloalkyl, CN, CO.sub.2 alkyl, cycloalkyl, phenyl, COalkyl, COphenyl, CHO,OH, NH.sub.2, NHCOalkyl or alkoxyR.sup.5 is H, halo or optionally substituted alkyl;R.sup.6 is H, halo or optionally substituted alkyl; provided that at least one of R.sup.5 and R.sup.6 is halo;R.sup.7 is CN, CHO, COOR.sup.8, CONR.sup.8 R.sup.9, where R.sup.8 is H, optionally substituted alkyl, alkenyl, alkynyl or aryl and R.sup.9 is a group R.sup.8, SO.sub.2 alkyl, NR.sup.10 R.sup.11 or N.sup.+ R.sup.10 R.sup.11 R.sup.12 Z.sup.- where Z is an agriculturally acceptable anion e.g. chloride and R.sup.10, R.sup.11 and R.sup.12 are independently selected from hydrogen and alkyl. Processes for the preparation of these compounds and compositions containing them are also described.
    Type: Grant
    Filed: November 7, 1989
    Date of Patent: June 9, 1992
    Assignee: Imperial Chemical Industries plc
    Inventor: David Cartwright
  • Patent number: 5053524
    Abstract: 3-Aminophenylpentane-1,5-diones of the formula I ##STR1## where R.sup.1 and R.sup.2 are, independently of one another, hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.4 -C.sub.8 -cycloalkyl, cyano-C.sub.2 -C.sub.4 -alkyl, hydroxy-C.sub.2 -C.sub.4 -alkyl, chloro-C.sub.2 -C.sub.4 -alkyl, phenyl-C.sub.1 -C.sub.2 -alkyl which can be substituted by chlorine, or phenyl which can be substituted by clorine or methyl, or R.sup.1 and R.sup.2 form, together with the nitrogen to which they are bonded, a heterocyclic radical which can contain further hetero atoms,R.sup.3 is hydrogen, fluorine, chlorine, C.sub.1 -C.sub.2 -alkyl or C.sub.2 -C.sub.5 -alkoxy or, if R.sup.3 is ortho to --NR.sup. R.sup.2, R.sup.3 and R.sup.2 together form C.sub.2 -C.sub.4 -alkylene, which can be substituted, or 1,2-phenylene andA is naphthyl or a radical of the formula II ##STR2## where X is hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.5 -alkyl, hydroxyl, C.sub.1 -C.sub.5 -alkoxy, phenoxy, phenyl-C.sub.1 -C.sub.
    Type: Grant
    Filed: April 27, 1990
    Date of Patent: October 1, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Friedrich-Wilhelm Raulfs, Udo Mayer, Andreas Oberlinner
  • Patent number: 4994495
    Abstract: Fungicidal compounds having the formula: ##STR1## and stereoisomers thereof, wherein R.sup.1 is optionally substituted C.sub.2-10 alkenyl, optionally substituted C.sub.5-6 cycloalkenyl, optionally substituted C.sub.2-10 alkynyl, or C.sub.1-10 alkyl substituted with --CN, --NC, --COR.sup.2, --CO.sub.2 R.sup.2, --NO.sub.2 or --SCN; X is O, S(O)n or NR.sup.2 and is attached to the 3- or the 4-position of the phenyl ring; Y and Z, which may be the same or different, are H, halogen, --CH.sub.3, --C.sub.2 H.sub.5, or --OCH.sub.3 ; R.sup.2 is H, C.sub.1-4 alkyl, C.sub.1-4 alkenyl, or, when R.sup.2 is C.sub.1-4 alkyl in the group --COR.sup.2, it joins with the alkyl group to which --COR.sup.2 is attached to form a 5- or 6-membered aliphatic ring; and n is 0, 1 or 2.
    Type: Grant
    Filed: May 11, 1989
    Date of Patent: February 19, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Christopher R. A. Godfrey, Paul J. de Fraine, Michael G. Hutchings, Ian Ferguson
  • Patent number: 4987253
    Abstract: Disclosed is a synthesis of desferrioxamine B and analogs and homologs thereof beginning with the generation of the O-protected N-(4-cyanobutyl)hydroxylamine which is acylated at the O-benzylhydroxylamine nitrogen with either succinic or acetic anhydride. The resulting half-acid amide or amide respectively, is subjected to a series of high yield condensations and reductions which provide desferrioxamine B in 45% overall yield. Finally, a desamino analog of desferrioxamine is prepared in order to demonstrate the synthetic utility of the scheme as applied to desferrioxamine derivatives.
    Type: Grant
    Filed: May 17, 1989
    Date of Patent: January 22, 1991
    Assignee: University of Florida
    Inventor: Raymond J. Bergeron
  • Patent number: 4889947
    Abstract: Sunscreen compositions are described which contain certain substituted naphthalenylidenes which act as UV filters when incorporated in a carrier in amounts ranging from 0.1-50% by weight.
    Type: Grant
    Filed: July 28, 1988
    Date of Patent: December 26, 1989
    Assignee: ICI Americas Inc.
    Inventors: Charalambos J. Phalangas, Thomas P. Cleary
  • Patent number: 4835180
    Abstract: N-(.omega.-cyanoalkyl)aminophenols of formula ##STR1## useful as lipoxygenase inhibitors and anti-asthmatic agents, are prepared by acylation of an aminophenol with an .omega.-haloalkanoyl chloride followed by reduction of the resulting amide then displacement of the halide by cyanide.
    Type: Grant
    Filed: October 2, 1986
    Date of Patent: May 30, 1989
    Assignee: Sterling Drug Inc.
    Inventors: Donald C. Schlegel, Robert E. Johnson
  • Patent number: 4803270
    Abstract: A process is disclosed for producing a fluoroaniline derivative of the formula: ##STR1## wherein X is an oxygen atom or an imino group. The process includes reacting 1,5-dichloro-2,4-dinitrobenzene with a glycol derivative of the formula:Y--CH.sub.2 --XH (II)wherein X is defined above and Y is a cyano group, a carboxy group or a lower alkoxycarbonyl group to produce a chlorodinitrobenzene derivative of the formula: ##STR2## wherein X and Y are as defined above. The chlorodinitrobenzene derivative (III) is reacted with a metal fluoride to produce a fluorodinitrobenzene derivative of the formula: ##STR3## wherein X and Y are as defined above. The fluorodintrobenzene derivative (IV) is subjected to reductive cyclization to obtain the fluoroaniline derivative (I).
    Type: Grant
    Filed: March 9, 1987
    Date of Patent: February 7, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Ichiki Takemoto
  • Patent number: 4803223
    Abstract: A substituted aminophenylurea derivative represented by the general formula ##STR1## wherein X.sup.1 and X.sup.2 are identical or different and each represents a halogen atom, andR represents a substituted or unsubstituted saturated or unsaturated aliphatic hydrocarbon group,and an acid addition salt thereof, and a process for preparation thereof, the compound of formula (I) being useful as antitumor agent.
    Type: Grant
    Filed: February 20, 1986
    Date of Patent: February 7, 1989
    Assignee: Tokuyama Soda Kabushiki Kaisha
    Inventor: Shozo Kato
  • Patent number: 4778887
    Abstract: The present invention is related with .alpha.-aryl-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)benzeneaceton itriles which are effective in destructing or preventing the growth of Protozoa in subjects suffering from such Protozoa.
    Type: Grant
    Filed: October 17, 1986
    Date of Patent: October 18, 1988
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Gustaaf M. Boeckx, Alfons H. M. Raeymaekers, Victor Sipido
  • Patent number: 4767760
    Abstract: Novel 5,6-dihydro-2-(substituted phenyl)-1,2,4-triazine-3,5(2H,4H)-diones which are effective in destroying or preventing the growth of Protozoa in subjects suffering from such Protozoa.
    Type: Grant
    Filed: January 21, 1987
    Date of Patent: August 30, 1988
    Assignee: Janssen Pharmacuetica N.V.
    Inventors: Gustaaf M. Boeckx, Alfons H. M. Raeymaekers, Victor Sipido