Processes Patents (Class 534/555)
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Patent number: 9096519Abstract: 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: GrantFiled: January 8, 2014Date of Patent: August 4, 2015Assignee: California Institute of TechnologyInventors: Bill Morandi, Robert H. Grubbs, Zachary K. Wickens, Michael M. Lerch
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Publication number: 20140194604Abstract: 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: ApplicationFiled: January 8, 2014Publication date: July 10, 2014Applicant: CALIFORNIA INSTITUTE OF TECHNOLOGYInventors: Bill MORANDI, Robert H. GRUBBS, Zachary K. WICKENS
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Publication number: 20140005149Abstract: Triazene-substituted diphenyl derivatives are suitable as chemotherapeutic agents for treating carcinomas in humans and animals.Type: ApplicationFiled: July 15, 2011Publication date: January 2, 2014Inventor: Heinz Förster
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Patent number: 8350014Abstract: 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: GrantFiled: November 17, 2009Date of Patent: January 8, 2013Assignee: Wisconsin Alumni Research FoundationInventors: Ronald Thaddeus Raines, Eddie Leonard Myers
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Publication number: 20100234327Abstract: 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: ApplicationFiled: July 3, 2008Publication date: September 16, 2010Applicant: TRIN PHARMA GMBHInventors: Rudolf Reiter, Jochen Kalbe, Heinz Forster
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Publication number: 20100093981Abstract: 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: ApplicationFiled: October 25, 2007Publication date: April 15, 2010Inventors: Andrey Yagodkin, Alex Azhayen
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Publication number: 20080039613Abstract: 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: ApplicationFiled: April 7, 2005Publication date: February 14, 2008Inventor: Jan Haller
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Patent number: 5618928Abstract: 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: GrantFiled: January 13, 1995Date of Patent: April 8, 1997Assignee: British Technology Group LimitedInventors: Malcolm F. G. Stevens, Daniel L. Rathbone, Dennis M. O'Shea
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Patent number: 5438122Abstract: 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: GrantFiled: August 23, 1994Date of Patent: August 1, 1995Assignee: Agfa-Gevaert, N.V.Inventor: Luc Vanmaele
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Patent number: 5328993Abstract: 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: GrantFiled: April 15, 1993Date of Patent: July 12, 1994Assignee: Bayer AktiengesellschaftInventors: Hauke Furstenwerth, Karl-Heinrich Lange, Roderich Raue, Alfred Brack
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Patent number: 5270453Abstract: 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: GrantFiled: November 17, 1992Date of Patent: December 14, 1993Assignee: Raychem CorporationInventors: Aldrich N. K. Lau, Lanchi P. Vo, Frank W. Mercer
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Patent number: 5268252Abstract: 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: GrantFiled: April 1, 1992Date of Patent: December 7, 1993Assignee: Hoechst AktiengesellschaftInventors: Siegfried Scheler, Wolfgang Zahn, Axel Schmitt, Gerhard Buhr
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Patent number: 4923970Abstract: 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: GrantFiled: March 28, 1988Date of Patent: May 8, 1990Assignee: Bionetics Research, Inc.Inventors: Christopher J. Michejda, Richard H. Smith, Jr.