Processes Patents (Class 534/555)
  • Patent number: 9096519
    Abstract: The present invention is directed to methods for oxidizing internal olefins to ketones. In various embodiments, each method comprising contacting an organic substrate, having an initial internal olefin, with a mixture of (a) a biscationic palladium salt; and (b) an oxidizing agent; dissolved or dispersed in a solvent system to form a reaction mixture, said solvent system comprising at least one C2-6 carbon nitrile and optionally at least one secondary alkyl amide, said method conducted under conditions sufficient to convert at least 50 mol % of the initial internal olefin to a ketone, said ketone positioned on a carbon of the initial internal olefin. The transformation occurs at room temperature and shows wide substrate scope. Applications to the oxidation of seed oil derivatives and a bioactive natural product are described.
    Type: Grant
    Filed: January 8, 2014
    Date of Patent: August 4, 2015
    Assignee: California Institute of Technology
    Inventors: Bill Morandi, Robert H. Grubbs, Zachary K. Wickens, Michael M. Lerch
  • Publication number: 20140194604
    Abstract: The present invention is directed to methods for oxidizing internal olefins to ketones. In various embodiments, each method comprising contacting an organic substrate, having an initial internal olefin, with a mixture of (a) a biscationic palladium salt; and (b) an oxidizing agent; dissolved or dispersed in a solvent system to form a reaction mixture, said solvent system comprising at least one C2-6 carbon nitrile and optionally at least one secondary alkyl amide, said method conducted under conditions sufficient to convert at least 50 mol % of the initial internal olefin to a ketone, said ketone positioned on a carbon of the initial internal olefin. The transformation occurs at room temperature and shows wide substrate scope. Applications to the oxidation of seed oil derivatives and a bioactive natural product are described.
    Type: Application
    Filed: January 8, 2014
    Publication date: July 10, 2014
    Applicant: CALIFORNIA INSTITUTE OF TECHNOLOGY
    Inventors: Bill MORANDI, Robert H. GRUBBS, Zachary K. WICKENS
  • Publication number: 20140005149
    Abstract: Triazene-substituted diphenyl derivatives are suitable as chemotherapeutic agents for treating carcinomas in humans and animals.
    Type: Application
    Filed: July 15, 2011
    Publication date: January 2, 2014
    Inventor: Heinz Förster
  • Patent number: 8350014
    Abstract: A method for making diazo-compounds, diazonium salts thereof and other protected forms of these compounds. Diaz-compounds are prepared by reaction of a tertiary phosphine reagent carrying a reactive carbonyl group with an azide. The reaction can also generate an acyl triazene which can be converted thermally or by addition of base to form the diazo-compound or the acyl triazene can be isolated. The method is particularly useful for conversion of azides carrying one or more electron withdrawing groups to diazo-compounds. The method can be carried out in aqueous medium under mild conditions and is particularly useful for conversion of azido sugars to diazo-compound and diazonium salts thereof under physiological conditions. Tertiary phosphine reagents, particularly those that are water-soluble, and precursors for preparation of the reagents are provided.
    Type: Grant
    Filed: November 17, 2009
    Date of Patent: January 8, 2013
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Ronald Thaddeus Raines, Eddie Leonard Myers
  • Publication number: 20100234327
    Abstract: The present invention relates to novel triazene compounds, to a process for their preparation, to pharmaceutical compositions comprising them, and to the use thereof in the treatment of cancer diseases in humans. The novel triazene compounds are distinguished, as compared with the known triazene compounds, by improved activity while at the same time having reduced toxicity, that is to say by fewer side-effects.
    Type: Application
    Filed: July 3, 2008
    Publication date: September 16, 2010
    Applicant: TRIN PHARMA GMBH
    Inventors: Rudolf Reiter, Jochen Kalbe, Heinz Forster
  • Publication number: 20100093981
    Abstract: The present invention relates to carbamoylation of amines, mercaptanes, thiophenols and phenols employing organic azides. More specifically, the invention relates to a method for generating urea derivatives, thiocarbamate derivatives and carbamate derivatives, and is based on the intermediate formation of isocyanate, starting from an organic azide. The reaction as described is useful in applications for modified nucleoside synthesis, oligonucleotide synthesis, as well as modification, labeling and conjugation of polymers and biomolecules.
    Type: Application
    Filed: October 25, 2007
    Publication date: April 15, 2010
    Inventors: Andrey Yagodkin, Alex Azhayen
  • Publication number: 20080039613
    Abstract: The invention relates to a method for producing azidoalkyl amines. According to said method, in a first step a bifunctional alkane comprising two different nucleofugic groups is reacted with an azide to form a monofunctional azidoalkane, during which process one nucleofugic group is cleaved and in a second step, the monofunctional azidoalkane is reacted with a primary or secondary amine to form azidoalkyl amine, during which process the second nucleofugic group is cleaved.
    Type: Application
    Filed: April 7, 2005
    Publication date: February 14, 2008
    Inventor: Jan Haller
  • Patent number: 5618928
    Abstract: Compounds of formula I: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each independently hydrogen, alkyl or acyl, R.sup.5 is alkyl, X represents a hydrophobic substituent and n is an integer from 1 to 3, and R.sup.6 and R.sup.7 each represent alkyl, cycloalkyl, or aralkyl, or R.sup.6 and R.sup.7 together with the nitrogen to which they are attached form a heterocyclic ring, with the proviso that one or both of R.sup.6 and R.sup.7, or the heterocyclic ring including R.sup.6 and R.sup.7, carries and/or includes at least one oxygen or sulphur atom, or a salt or N-oxide thereof may be used in the treatment of P. carinii infections.
    Type: Grant
    Filed: January 13, 1995
    Date of Patent: April 8, 1997
    Assignee: British Technology Group Limited
    Inventors: Malcolm F. G. Stevens, Daniel L. Rathbone, Dennis M. O'Shea
  • Patent number: 5438122
    Abstract: The present invention provides triazene dyes according to formula (I) for use in thermal transfer printing:A--N.dbd.N--NR.sup.1 R.sup.2 (I)wherein A is the residue of a diazotisable heteroaromatic amine, R.sup.1 and R.sup.2 independently represent hydrogen, an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an aryl group, a substituted aryl group, a cycloalkyl group, a substituted cycloalkyl group, an aralkyl group, or R.sup.1 and R.sup.2 represent the atoms necessary to complete a ring system or a substituted ring system.
    Type: Grant
    Filed: August 23, 1994
    Date of Patent: August 1, 1995
    Assignee: Agfa-Gevaert, N.V.
    Inventor: Luc Vanmaele
  • Patent number: 5328993
    Abstract: The new cationic triazatrimethine dyestuffs of the formula ##STR1## wherein the substituents B, Z, R.sup.2 and An.sup..crclbar. have the meaning given in the description, are suitable for dyeing and printing naturally occurring and synthetic materials.
    Type: Grant
    Filed: April 15, 1993
    Date of Patent: July 12, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hauke Furstenwerth, Karl-Heinrich Lange, Roderich Raue, Alfred Brack
  • Patent number: 5270453
    Abstract: Aromatic bistriazene compounds of the formula ##STR1## wherein --R.sub.1, --R.sub.2, --R.sub.3, and --R.sub.4 are independently --H, --C.sub.6 H.sub.5, --C.sub.6 H.sub.4 Y, or C.sub.1 -C.sub.4 alkyl; --R.sub.5 -- is ##STR2## --R.sub.6 is --F, --Cl, --Br, --CH.sub.3, or --CF.sub.3 ; r is 0, 1, 2, 3, or 4; and --Y is halogen, --NO.sub.2, --C.sub.6 H.sub.5, or C.sub.1 -C.sub.4 alkyl. These bistriazene compounds are useful for cross-linking polymers such as poly(imides), poly(aryl ether ketones), poly(aryl ether sulfones), poly(quinolines), poly(quinoxalines), and nonaromatic fluoropolymers having aliphatic C--H groups.
    Type: Grant
    Filed: November 17, 1992
    Date of Patent: December 14, 1993
    Assignee: Raychem Corporation
    Inventors: Aldrich N. K. Lau, Lanchi P. Vo, Frank W. Mercer
  • Patent number: 5268252
    Abstract: The invention relates to a radiation-sensitive ester which is the condensation product of (a) a compound containing 2 to 6 aromatic hydroxyl groups, (b) a ring-substituted (o-naphthoquinone 2-diazide)-4-sulfonic acid (compound D.sub.1 and (c) an (o-naphthoquinone 2-diazide)-4- or -5-sulfonic acid which is not further substituted (compound D.sub.2) and/or a non-radiation-sensitive organic acid (compound D.sub.0), where the (b):(c) molar ratio is between 0.1:1 and 39:1.
    Type: Grant
    Filed: April 1, 1992
    Date of Patent: December 7, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Siegfried Scheler, Wolfgang Zahn, Axel Schmitt, Gerhard Buhr
  • Patent number: 4923970
    Abstract: A substituted 1-(2-chloroethyl)-3-acyl-3-alkyltriazene of the formula: ##STR1## in which R.sub.1 is 1-oxoalkyl containing from two to eight carbon atoms, fluorinated 1-oxoalkyls containing from two to eight carbon atoms and substituted with up to three fluorine atoms, benzoyl, phenylacetyl, carboalkoxy containing from two to eight carbon atoms, fluorinated carboalkyl containing from two to eight carbon atoms and up to three fluorine atoms, carbophenoxy, N-phenyl aminocarbonyl, N-alkyl aminocarbonyl containing from two to eight carbon atoms, thiocarbamoyl, N-alkylthiocarbamoyls with from two to eight carbon atoms, N-phenylthiocarbamoyl, dialkylphosphonates in which the alkyl groups can be the same or different and each contains from one to seven carbon atoms, phenylsulfonyl, and meta or para-substituted phenylsulfonyl in which the meta or para substituent is methyl, ethyl, methoxy, ethoxy, fluoro and chloro; and R.sub.
    Type: Grant
    Filed: March 28, 1988
    Date of Patent: May 8, 1990
    Assignee: Bionetics Research, Inc.
    Inventors: Christopher J. Michejda, Richard H. Smith, Jr.