Plural Ring Oxygens In The Hetero Ring Patents (Class 549/221)
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Patent number: 11787844Abstract: The present invention relates to functional binding fragments comprising the minimal binding fragments of VAR2CSA, to antibodies against such binding fragments of VAR2CSA, nucleic acids encoding such fragments of VAR2CSA as well as methods for their production. The invention further relates to conjugates and fusion proteins of VAR2CSA polypeptides including the minimal binding fragments and their use, in particular in the treatment of conditions associated with expression of chondroitin sulfate A (CSA), such as an inappropriate expression of chondroitin sulfate A (CSA).Type: GrantFiled: February 8, 2013Date of Patent: October 17, 2023Assignee: VAR2 Pharmaceuticals APSInventors: Ali Salanti, Thor Grundtvig Theander, Mads Daugaard, Morten Nielsen, Madeleine Dahlback, Thomas Mandel Clausen
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Patent number: 10588887Abstract: The present invention relates to ophthalmic compositions and methods for the treatment of dry eye and other inflammatory ocular conditions. In particular, the present invention relates to a composition comprising an esterified anti-inflammatory lipid mediator, which is an ester of an anti-inflammatory lipid mediator that is a reaction product of the anti-inflammatory lipid mediator and a polyol wherein the majority of the anti-inflammatory lipid mediator is present in an ester form. In this way, the compositions are substantially free of an acid form of the anti-inflammatory lipid mediators. This composition can be topically delivered to the ocular surface via a preparation, solution, gel, ointment, and/or strip and/or a contact lens.Type: GrantFiled: August 22, 2014Date of Patent: March 17, 2020Assignee: Johnson & Johnson Vision Care, Inc.Inventor: Annabelle Gallois-Bernos
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Patent number: 9562114Abstract: Cyclic carbonate azide having a structure according to the following formula (A) wherein R1-R5 are independently selected from the group consisting of hydrogen, C6-20 aryl, C7-36 aralkyl, and C1-30 alkyl groups; said aryl, aralkyl, and alkyl groups my optionally be substituted with heteroatoms, X is a hydrocarbon moiety having at least one carbon atom, T has the structure —N(R6)— or —O—, R6 is selected from the group consisting of hydrogen and C1-20 alkyl groups, optionally substituted with heteroatoms, k is 0, 1, or 2, m is 0 or 1, n is 0 or 1, p is 1 or 2, Z is an aliphatic or aromatic hydrocarbon moiety having at least one carbon atom, optionally substituted with heteroatoms, and Y is either (B) or C) or (D).Type: GrantFiled: October 31, 2014Date of Patent: February 7, 2017Assignee: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.Inventors: Waldo Joseph Elisabeth Beek, Auke Gerardus Talma
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Patent number: 9381508Abstract: The disclosure is directed to: (a) phosphacycle ligands; (b) catalyst compositions comprising phosphacycle ligands; and (c) methods of using such phosphacycle ligands and catalyst compositions in bond forming reactions.Type: GrantFiled: August 24, 2015Date of Patent: July 5, 2016Assignee: ABBVIE INC.Inventors: Shashank Shekhar, Thaddeus S. Franczyk, David M. Barnes, Travis B. Dunn, Anthony R. Haight, Vincent S. Chan
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Patent number: 9045575Abstract: The present invention provides hypophosphite (co)telomers of methacrylic anhydride having a weight average molecular weight of from 1,000 to 20,000, and having, on average, at least one phosphorus atom bound to two carbon atoms, and at least one carboxylic acid or salt group.Type: GrantFiled: November 6, 2012Date of Patent: June 2, 2015Assignee: Rohm and Haas CompanyInventors: Charles J. Rand, Barry Weinstein, C. Damien Rodowski
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Patent number: 8975443Abstract: The disclosure is directed to: (a) phosphacycle ligands; (b) catalyst compositions comprising phosphacycle ligands; and (c) methods of using such phosphacycle ligands and catalyst compositions in bond forming reactions.Type: GrantFiled: August 21, 2012Date of Patent: March 10, 2015Assignee: AbbVie Inc.Inventors: Shashank Shekhar, Thaddeus S. Franczyk, David M. Barnes, Travis B. Dunn, Anthony R. Haight, Vincent S. Chan
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Publication number: 20140323743Abstract: The present invention provides hypophosphite (co)telomers of methacrylic anhydride having a weight average molecular weight of from 1,000 to 20,000, and having, on average, at least one phosphorus atom bound to two carbon atoms, and at least one carboxylic acid or salt group.Type: ApplicationFiled: November 6, 2012Publication date: October 30, 2014Inventors: Charles J. Rand, Barry Weinstein, C. Damien Rodowski
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Patent number: 8841487Abstract: The disclosure is directed to: (a) phosphacycle ligands; (b) methods of using such phosphacycle ligands in bond forming reactions; and (c) methods of preparing phosphacycle ligands.Type: GrantFiled: July 15, 2011Date of Patent: September 23, 2014Assignee: AbbVie Inc.Inventors: Shashank Shekhar, Thaddeus S. Franczyk, David M. Barnes, Travis B. Dunn, Anthony R. Haight, Vincent S. Chan
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Publication number: 20140228323Abstract: The present invention provides a compound of formula I; or a pharmaceutically acceptable salt thereof, wherein R1, R2 and R3 are defined herein. The invention also relates to a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides pharmaceutical composition of the compounds of the invention and a combination of pharmacologically active agents and a compound of the invention.Type: ApplicationFiled: February 12, 2014Publication date: August 14, 2014Applicant: NOVARTIS AGInventors: David Weninger BARNES, Scott Louis COHEN, Dean Franklin Rigel
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Publication number: 20140154675Abstract: Compounds having chemiluminescent flash and glow properties. Also disclosed are methods using the compounds to generate light, detect and/or quantify enzymes, antigens, and/or nucleic acids. Also disclosed are kits relating to these compounds.Type: ApplicationFiled: April 30, 2012Publication date: June 5, 2014
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Publication number: 20140135506Abstract: Disclosed are methods for making chiral phosphorus ligands including chiral phosphines, chiral phosphine oxides, phosphonamides, and aminophosphines. The chiral phosphorus ligands prepared by the methods of the invention are useful as components of chiral catalysts, e.g., transition metal complexes.Type: ApplicationFiled: November 14, 2013Publication date: May 15, 2014Applicant: BOEHRINGER INGELHEIM INTERNATIONAL GMBHInventors: Zhengxu HAN, Chris Hugh SENANAYAKE
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Publication number: 20130158219Abstract: The invention relates to compounds, in particular phosphinic ligands of metal complexes, as well as to metal complexes including said ligands and to supported catalysts including said metal complexes or said compounds. The invention also relates to methods for synthesizing said compounds, to complexes, and to supported catalysts, as well as to intermediate products used in said synthesis methods. The invention further relates to the uses of said compounds. The compounds of the invention are ferrocene compounds which have been functionalized so as to be capable of being heterogenized. The invention can be used in particular in the field of heterogeneous catalysis.Type: ApplicationFiled: June 24, 2011Publication date: June 20, 2013Applicants: Universite de Bourgogne, Centre National De La Recherche ScientifiqueInventors: Jean-Cyrille Hierso, Matthieu Beauperin, Philippe Meunier
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Publication number: 20120022252Abstract: The disclosure is directed to: (a) phosphacycle ligands; (b) methods of using such phosphacycle ligands in bond forming reactions; and (c) methods of preparing phosphacycle ligands.Type: ApplicationFiled: July 15, 2011Publication date: January 26, 2012Applicant: ABBOTT LABORATORIESInventors: Shashank Shekhar, Thaddeus S. Franczyk, David M. Barnes, Travis B. Dunn, Anthony R. Haight, Vincent S. Chan
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Publication number: 20120006358Abstract: The invention relates to machine dishwashing agents containing specific polycarbonate-, polyurethane-, and/or polyurea-polyorganosiloxane compounds or precursor compounds thereof of the reactive cyclic carbonate and urea type which help to avoid the formation of water spots and filming after the use of the agents and accelerate the drying of dishes.Type: ApplicationFiled: September 20, 2011Publication date: January 12, 2012Applicant: Henkel AG & Co. KGaAInventors: Nadine Warkotsch, Marc-Steffen Schiedel, Johannes Zipfel, Arnd Kessler
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Publication number: 20110318292Abstract: Compounds derived from acetone are provided. Particularly, the compounds are derivatives of hydroxyacetone, including dimers of both 1-hydroxyacetone and 1,3-dihydroxyacetone. The hydroxy moieties on the core hydroxyacetone molecule serves as an attachment point for a variety of moieties (e.g., ethers, esters, phosphorous containing, or nitrogen containing) that are selected to provide the compound with a particular property. Applications of the compounds include plasticizers, supersurfactants, and additives for health care products, such as shampoo and perfume.Type: ApplicationFiled: June 27, 2011Publication date: December 29, 2011Applicant: BOSTON POLYMER LLCInventors: Gregory David Phelan, William Brenden Carlson
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Patent number: 7968735Abstract: The invention concerns novel 1,2-dioxetane derivatives of general formula (I) as defined in the description, capable of emitting a detectable luminescent signal, their use in a method for detecting and/or quantizing a physical, chemical or biological, in particular enzymatic, phenomenon, as well as a kit for implementing said method.Type: GrantFiled: May 24, 2006Date of Patent: June 28, 2011Assignees: Quidd, Universite de RouenInventors: Pierre-Yves Renard, Anthony Romieu, Marc Massonneau
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Publication number: 20110087013Abstract: The present invention concerns a synthesis process comprising the following steps (i) reacting 3-ethyl-4-nitrobenzoic acid with thionyl chloride to produce a 3-ethyl-4-nitrobenzoic acid chloride or a 3-ethyl-4-nitrobenzoic acid anhydride from 3-ethyl-4-nitrobenzoic acid by means of water cleavage and (ii) Friedel-Crafts acylation by reacting the 3-ethyl-4-nitrobenzoic acid chloride or the 3-ethyl-4-nitrobenzoic acid anhydride with an optionally substituted aryl-H to form an optionally substituted (3-ethyl-4-nitrophenyl)-aryl-methanone. In addition the present invention concerns compounds containing (3-ethyl-4-nitrophenyl)-aryl-methanone, characterized in that the optionally substituted aryl is an optionally substituted condensed aromate.Type: ApplicationFiled: October 5, 2010Publication date: April 14, 2011Inventor: Bernhard Knipp
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Publication number: 20100317031Abstract: New chemiluminescent compounds, stable in aqueous buffers, for use in biological assaying include acridane-based compounds and 1,2-dioxetanes. Among the new acridane-based compounds are water-soluble acridanes, enhancer coupled acridanes, bis and tris-acridanes as well as acridane-1,2-dioxetanes. Among the new 1,2-dioxetanes are electron deficient group-containing dioxetanes and tethered bis-1,2-dioxetanes. The 1,2-dioxetanes are useful as substrates for various enzymes. The acridanes can be admixed with an oxidizing agent an aqueous buffer and, optionally, a stabilizer to form a substrate or reagent formulation useful for assaying, inter alia, HRP.Type: ApplicationFiled: August 23, 2010Publication date: December 16, 2010Inventors: Brij Pal Giri, Dinesh Dagli, Pritam Singh
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Patent number: 7531682Abstract: The present invention concerns a process for hydrocyanating ethylenically unsaturated organic compounds to compounds containing at least one nitrile function. It relates more particularly to the hydrocyanation of diolefins such as butadiene or of substituted olefins such as alkenenitriles, for instance pentenenitriles. According to the process of the invention the reaction is implemented in the presence of a metal complex catalyst comprising a transition metal such as nickel and an organic ligand.Type: GrantFiled: July 11, 2003Date of Patent: May 12, 2009Assignee: Rhodia Polyamide IntermediatesInventors: Jean-Christophe Galland, Blaise Didillon, Philippe Marion, Damien Bourgeois
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Patent number: 7422908Abstract: A method of generating light through chemiluminescence involves providing a stable 1,2-dioxetane of the formula: Wherein (a) R1 and R2 are each, individually, a chemical reactive site or when fused together form a chemical reactive site, and R3 and R4 are each, individually, a chemical reactive site or when fused together form a chemical reactive or (b) R1 has at least two hetero atoms with chemical reactive site and R3 and R4 are inactive site and R2 is a chemical reactive site.Type: GrantFiled: October 4, 2002Date of Patent: September 9, 2008Inventor: Brij P. Giri
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Preparation of oseltamivir phosphate (Tamiflu) and intermediates starting from D-glucose or D-xylose
Publication number: 20080009639Abstract: Novel processes for the preparation of the anti-viral agent, Oseltamivir Phosphate and novel intermediates prepared in such processes. The novel processes use as starting materials D-glucose or D-xylose in the preparation of Oseltamivir Phosphate.Type: ApplicationFiled: February 23, 2007Publication date: January 10, 2008Inventors: Bruno Konrad Radatus, K.S. Keshava Murthy, Gamini Weeratunga, Stephen E. Horne, Kiran Kumar Kothakonda, Eckardt C.G. Wolf, Zhongyi Wang -
Patent number: 7300766Abstract: A compound for enhancing the light output of a chemiluminescent system and, in particular, a stabilized, triggerable 1,2-dioxetane, is obtained by reacting a polyvinylbenzyl halide and a bilinker with either a trisubstituted amine or trisubstituted phosphine. A fluorescent molecule may be attached to polymer along with the trisubstituted amine or trisubstituted phosphine. Also, the benzyl halide may be reacted with a ?-electron donor, such as a vinyl naphthalene or vinylanthracene to form a co-polymer which is polymerizable with the trisubstituted amine and/or trisubstituted phosphine. By controlling the reaction parameters it is possible to obtain either a water-soluble or partial water soluble or insoluble compound crosslink polymer.Type: GrantFiled: May 23, 2003Date of Patent: November 27, 2007Inventor: Brij P. Giri
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Patent number: 7253298Abstract: The present invention concerns a process for hydrocyanating ethylenically unsaturated organic compounds to compounds containing at least one nitrile function. It relates more particularly to the hydrocyanation of diolefins such as butadiene or of substituted olefins such as alkenenitriles, for instance pentenenitriles. According to the process of the invention the reaction is implemented in the presence of a metal complex catalyst comprising a transition metal such as nickel and an organic ligand.Type: GrantFiled: June 24, 2005Date of Patent: August 7, 2007Assignee: Rhodia Polyamide IntermediatesInventors: Jean-Christophe Galland, Blaise Didillon, Philippe Marion, Damien Bourgeois
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Patent number: 7019024Abstract: The invention provides a pharmaceutical for treatment of neurological and neuropsychiatric disorders comprising a compound of the formula: or a pharmaceutically acceptable salt thereof.Type: GrantFiled: January 9, 2001Date of Patent: March 28, 2006Assignee: Allelix Neuroscience Inc.Inventors: Vassil Iliya Ognyanov, Laurence A. Borden, Stanley Charles Bell, Jing Zhang
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Patent number: 6878665Abstract: The invention relates to novel diphosphines, in optically pure or racemic form, of formula (I): in which: R1 and R2 are a (C5-C7)cycloalkyl group, an optionally substituted phenyl group or a 5-membered heteroaryl group; and A is (CH2—CH2) or CF2. The invention further relates to the use of a compound of formula (I) as a ligand for the preparation of a metal complex useful as a chiral catalyst in asymmetric catalysis, and to the chiral metal catalysts comprising at least one ligand of formula (I).Type: GrantFiled: September 16, 2002Date of Patent: April 12, 2005Assignee: SynkemInventors: Sébastien Duprat de Paule, Nicolas Champion, Virginie Vidal, Jean-Pierre Genet, Philippe Dellis
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Patent number: 6806375Abstract: Intermediates such as methyl 2,2-dimethyl-5-ethenyl-1,3-dioxane-5-carbonate useful to prepare antiviral compounds such as penciclovir and famciclovir are disclosed.Type: GrantFiled: February 19, 2003Date of Patent: October 19, 2004Assignee: Novartis International Pharmaceutical Ltd.Inventors: Richard Freer, Graham Richard Geen, Thomas Weir Ramsay, Andrew Colin Share, Neil Michael Smith
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Patent number: 6767716Abstract: A chemiluminescent 1,2-dioxetane includes an alkaline phosphatase triggerable stable 1,2-dioxetane; a polymeric enhancer which is either an ammonium or phosphonium salt of a polyvinylbenzyl chloride and an aqueous enzyme diluent or stabilizer which corresponds to blood component including blood protein. The system is efficacious for single molecule detection of alkaline phosphatase and other enzymes.Type: GrantFiled: June 18, 2001Date of Patent: July 27, 2004Inventor: Brij P. Giri
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Patent number: 6706740Abstract: Heterocyclic aromatic amides (HAA) according to Formula I: wherein X1-X4, M, Z, and A are herein defined. The invention also encompasses hydrates, salts and complexes thereof. These compounds are useful as antifungal agents.Type: GrantFiled: December 13, 2001Date of Patent: March 16, 2004Assignee: Dow AgroSciences LLCInventors: Michael J. Ricks, William H. Dent, III, Richard B. Rogers, Chenglin Yao, Bassam S. Nader, John L. Miesel, Gina M. Fitzpatrick, Kevin G. Meyer, Noormohamed M. Niyaz, Irene M. Morrison, Matthew J. Henry, Jenifer L. Adamski Butz, Robert P. Gajewski
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Ortho substituted chiral phosphines and phosphinites and their use in asymmetric catalytic reactions
Patent number: 6653485Abstract: 3,3′-Substituted chiral biaryl phosphine and phosphinite ligands and metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. The metal complexes are useful as catalysts in asymmetric reactions, such as, hydrogenation, hydride transfer, allylic alkylation, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, olefin metathesis, hydrocarboxylation, isomerization, cyclopropanation, Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition, epoxidation, kinetic resolution and [m+n] cycloaddition. The metal complexes are particularly effective in Ru-catalyzed asymmetric hydrogenation of beta-ketoesters to beta-hydroxyesters and Ru-catalyzed asymmetric hydrogenation of enamides to beta amino acids.Type: GrantFiled: November 16, 2001Date of Patent: November 25, 2003Assignee: The Penn State Research FoundationInventor: Xumu Zhang -
Patent number: 6630114Abstract: The invention relates to new calixarenes according to the formula: wherein R1 and R2, which may be identical or different, are alkyl, alkoxy or aryl groups, and n is an integer equal to 2, 3 or 4. Said calixarenes may be used to extract actinides and lanthanides from aqueous solutions.Type: GrantFiled: July 10, 2001Date of Patent: October 7, 2003Assignee: Commissariat a l'Energie AtomiqueInventors: Jean-François Dozol, Hélène Rouquette, Alejandro Garcia Carrera, Laetitia Delmau, Volker Böhmer, Alexander Shivanyuk, Christian Muzigmann
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Patent number: 6576772Abstract: Chiral ligands and transition metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. The chiral ligands include (R,S,S,R)-DIOP*. The ruthenium complex reduces enamide to the corresponding amine with up to 99% enantioselectivity. The transition metal complexes of the chiral ligands are useful in asymmetric reactions such as asymmetric hydrogenation, hydride transfer, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, hydrocarboxylation, isomerization, allylic alkylation, cyclopropanation, Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition and epoxidation reactions.Type: GrantFiled: November 10, 2000Date of Patent: June 10, 2003Assignee: The Penn State Research FoundationInventor: Xumu Zhang
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Patent number: 6528627Abstract: The present invention provides for substituted metal chelating compounds in which at least two of the chelating atoms are nitrogen which are directly attached to aromatic rings and one or more of those nitrogen atoms has attached thereto a substituent other than hydrogen, and methods for making and using these compounds.Type: GrantFiled: November 28, 2000Date of Patent: March 4, 2003Assignee: NeoRx CorporationInventor: Sudhakar Kasina
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Patent number: 6461876Abstract: The present invention provides novel 1,2-dioxetanes derived from spiro-fused ketones with or without &pgr;-electrons in the ring or with carbon-carbon double bond(s) in the spiro-fused ring. Additionally, these new dioxetanes have electron donating or withdrawing groups at the four-membered peroxide ring to render these dioxetanes active at all sites.Type: GrantFiled: August 21, 2000Date of Patent: October 8, 2002Inventor: Brij P. Giri
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Publication number: 20020028791Abstract: This invention relates generally to phosphate esters of bis-amino acid sulfonamides containing substituted benzyl amines of formula I: 1Type: ApplicationFiled: July 18, 2001Publication date: March 7, 2002Inventors: Robert F. Kaltenbach, George L. Trainor
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Patent number: 6337406Abstract: Chiral phosphine ligands derived from chiral natural products including D-mannitol and tartaric acid. The ligands contain one or more 5-membered phospholane rings with multiple chiral centers, and provide high stereoselectivity in asymmetric reactions.Type: GrantFiled: August 19, 1999Date of Patent: January 8, 2002Assignee: The Penn State Research FoundationInventor: Xumu Zhang
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Patent number: 6313317Abstract: Disclosed is a ruthenium-phosphine complex usable as the catalyst giving a high enantiomer excess in an asymmetric reaction and a method for producing the complex. The ruthenium-phosphine complex is represented by formula (1): [{(RuX(L)}2(&mgr;-X)3]−[R22NH2]+ (1) wherein R2 represents hydrogen, alkyl, cycloalkyl or benzyl and L represents a diphosphine ligand represented by formula (2): wherein R1 represents an optionally substituted phenyl group and X represents a halogen atom. The method for preparing a ruthenium-phosphine complex represented by formula (1) is characterized in that a ruthenium complex represented by the formula [RuX(arene)(L)]X and an ammonium salt represented by the formula R22NH.HX are reacted with each other.Type: GrantFiled: March 22, 1999Date of Patent: November 6, 2001Assignee: Takasago International CorporationInventors: Noboru Sayo, Takao Saito, Tohru Yokozawa
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Patent number: 6287767Abstract: A chemiluminescent assays for the determination of the presence or amount of a biopolymer in bound assays using 1,2-dioxetanes in connection with AttoPhos™ as chemiluminescent substrates for enzyme-labeled targets or probes is provided. Further disclosed is a kit for conducting a bioassay for the presence or concentration of a biopolymer comprising a) an enzyme complex; b) a 1,2-dioxetane; and c) AttoPhos™.Type: GrantFiled: November 12, 1998Date of Patent: September 11, 2001
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Patent number: 6184390Abstract: A catalyst for the bisalkoxycarbonylation of olefins comprising a noble metal compound and a phosphine chalcogenide of the following formula (1): wherein each of R1, R2 and R3 is, independently, an alkyl group or an aryl group each of which may have a substituent, and A is a Group 16 element of the Periodic Table; and R1, R2 or R3 may be combined, directly or through a bridging group, with one another where the groups to be combined may be attached either to an identical phosphorus atom or to different phosphorus atoms. Element A includes oxygen, sulfur and selenium atoms. The noble metal compound includes palladium(II) halides and other palladium compounds. The catalyst may further include a copper(I) halide or other copper compound as a co-catalyst. The use of this catalyst can provide the bisalkoxycarbonylation of olefins with efficiency.Type: GrantFiled: September 27, 1999Date of Patent: February 6, 2001Assignee: Daicel Chemical Industries, Ltd.Inventors: Kazuhiko Saigo, Yukihiko Hashimoto, Minoru Hayashi
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Patent number: 6162929Abstract: A process for the manufacture of bisphosphine oxide compounds and bisphosphonates as intermediates for the production of bisphosphine ligands, in which in a single step processa) a phosphine oxide compound is reacted in an organic solvent at -70.degree. C. to 20.degree. C. with 0.5-3 eq. of a lithium or magnesium amide compound,b) 0.5-3 eq. of oxidatively-acting metal salt or metal salt complex are added to the suspension obtained in stage a) in a temperature range of -70.degree. C. to 20.degree. C., with a racemate of a bisphosphine oxide compound being obtained;c) a racemate cleavage is carried out if desired; andd) the bisphosphonates obtained in stage b) or c) are converted into bisphosphine oxides.Type: GrantFiled: December 15, 1998Date of Patent: December 19, 2000Assignee: Hoffmann-La Roche Inc.Inventors: Joseph Foricher, Rudolf Schmid
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Patent number: 6153769Abstract: A process for the manufacture of polyene aldehydes comprises reacting a polyene O,O-ethylene acetal with a 1-alkoxy-1,3-diene in the presence of a Lewis acid or Bronsted acid, hydrolyzing the resulting condensation product and cleaving off alcohol under basic or acidic conditions from the polyene derivative produced at this stage. The novel polyene O,O-ethylene acetals as well as the likewise novel condensation products in this process form further aspects of the invention. The final products are primarily carotenoids which find corresponding use, e.g. as colorants and pigments for foodstuffs, animal products etc.Type: GrantFiled: November 17, 1998Date of Patent: November 28, 2000Assignee: Roche Vitamins Inc.Inventor: August Ruttimann
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Patent number: 6132956Abstract: Dioxetanes that can be triggered by bases are provided which can be used to detect bases in organic solvents, aqueous preparations and detect gaseous bases in the atmosphere. The dioxetanes can be used to detect the release of bases from various labels, as a means to detect the presence of a base released by physical or natural processes, to calibrate light measuring apparatus and to determine the amount of reducing or oxidizing agent present in the base.Type: GrantFiled: November 5, 1997Date of Patent: October 17, 2000
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Patent number: 6107036Abstract: Compounds of the general formula Ia and Ib are described ##STR1## in which R.sup.1 and R.sup.2 are the same or different and represent hydrogen, straight-chain or branched C.sub.1 to C.sub.6 lower alkyl or an aryl group optionally substituted by electron-withdrawing groups, R.sup.3 denotes a cleavable group, W is hydrogen, halogen or a pseudohalogen and at least one of the groups R.sup.4 or R.sup.5 is a group stabilizing the dioxetane structure and at most one of the groups R.sup.4 or R.sup.5 represents hydrogen and X or Y represents oxygen, N-R or C(R).sub.2 in which R has the meanings stated for R.sup.1 and R.sup.2 or represents a mesomeric double bond or a carbonyl group and n denotes the number 0 or 1 and m denotes the number 1 or 2, as well as a process for their production. These compounds are new and can be used as substrates in immunological assays and in DNA diagnostics using activating agents for colour formation.Type: GrantFiled: April 20, 1998Date of Patent: August 22, 2000Assignee: Roche Diagnostics GmbHInventors: Dieter Heindl, Hans-Peter Josel, Herbert Von Der Eltz, Rupert Herrmann, Hans-Joachim Holtke, Rainer Beckert, Dieter Weiss, Waldemar Adam
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Patent number: 6001659Abstract: Chemiluminescent electron-rich aryl-substituted 1,2-dioxetane compounds are disclosed in which the aryl group is poly-substituted with suitable electron-donating groups such that the light-emitting pattern of the molecule results in a very high luminescent count, thus providing for a sensitive and precise assay for haptens, analytes, polynucleotides and the like. These substituted aryl-containing 1,2-dioxetane compounds can be used as direct labels in an immunoassay or when derivatized with an appropriate leaving group, can be used as a substrate for a enzyme immunoassay. The unusual chemiluminescence of the compounds allows the timing of the luminescent reaction to be exactly controlled.Type: GrantFiled: May 9, 1995Date of Patent: December 14, 1999Assignee: Abbott LaboratoriesInventors: Nai-Yi Wang, Roger C. Hu
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Patent number: 6001561Abstract: Chemiluminescent electron-rich aryl-substituted 1,2-dioxetane compounds are disclosed in which the aryl group is poly-substituted with suitable electron-donating groups such that the light-emitting pattern of the molecule results in a very high luminescent count, thus providing for a sensitive and precise assay for haptens, analytes, polynucleotides and the like. These substituted aryl-containing 1,2-dioxetane compounds can be used as direct labels in an immunoassay or when derivatized with an appropriate leaving group, can be used as a substrate for a enzyme immunoassay. The unusual chemiluminescence of the compounds allows the timing of the luminescent reaction to be exactly controlled.Type: GrantFiled: May 9, 1995Date of Patent: December 14, 1999Assignee: Abbott LaboratoriesInventors: Nai-Yi Wang, Roger C. Hu
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Patent number: 5981768Abstract: A new class of stable dioxetanes bears a polycyclic stabilizing group and aryloxy moiety, the oxygen atom of which is provided with a protective group which can be removed by an enzymatic or chemical trigger admixed with the dioxetane. The polycyclic stabilizing group is preferably spiroadamantane. The group further bears an alkoxy, aryloxy, aralkyloxy or cycloalkyloxy moiety which is partially or completely substituted with halogens, particularly fluorine and chlorine. Proper selection of electron active groups on the stabilizing moiety, the aryl group and the OR group yields enhanced enzyme kinetics, superior light intensity and excellent detection sensitivity in various assays.Type: GrantFiled: September 21, 1998Date of Patent: November 9, 1999
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Patent number: 5872273Abstract: A novel diphosphine compound of the formula (I): ##STR1## where R.sup.1 and R.sup.2 represent independently cycloalkyl, unsubstituted or substituted phenyl, or a five-membered heteroaromatic ring. The compound is useful as a ligand for an asymmetric reaction, in particular, as an asymmetric hydrogenation catalyst.Type: GrantFiled: December 22, 1997Date of Patent: February 16, 1999Assignee: Takasago International CorporationInventors: Takao Saito, Tohru Yokozawa, Xiaoyaong Zhang, Noburo Sayo
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Patent number: 5773628Abstract: A chemiluminescent assay method and compositions are described which use a haloalkoxy group-substituted dioxetane which is deprotected by a hydrolytic enzyme to undergo a chemiluminescent reaction. Chemiluminescent 1,2-dioxetane compounds substituted on the dioxetane ring with a haloalkoxy group which can be triggered by a reagent to generate light are disclosed. Haloalkoxy group-substituted dioxetanes are useful for the detection of triggering agents including enzymes. The enzyme may be present alone or linked to a member of a specific binding pair in an immunoassay, DNA probe assay or other assay where the enzyme is bound to a reporter molecule.Type: GrantFiled: November 14, 1994Date of Patent: June 30, 1998Assignee: Tropix, Inc.Inventors: Hashem Akhavan-Tafti, Zahra Arghavani, Robert A. Eickholt, Khaledur S. Rashid
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Patent number: 5756770Abstract: A novel synthesis of 1,2-dioxetane phosphate alkali metal salts and novel intermediates employed in this synthesis are disclosed. A hydroxyaryl enol ether alkali metal salt having the formula: ##STR1## wherein T can be an unsubstituted or substituted adamant-2'-ylidene group, R.sup.3 can be a methyl group, Y can be a phenyl group and M.sup.+ can be a sodium cation, is reacted with a phosphorohalidate to give the corresponding enol ether ethylene phosphate, which is then reacted with an alkali metal cyanide to give the corresponding enol ether cyanoethyl phosphate diester alkali metal salt intermediate. Singlet oxygen addition to this enol ether cyanoethyl phosphate diester alkali metal salt intermediate to give the corresponding 1,2-dioxetane cyanoethyl phosphate diester alkali metal salt, followed by .beta.-elimination of the cyanoethyl group using an alkali metal hydroxide or the like, gives the corresponding 1,2-dioxetane phosphate alkali metal salt.Type: GrantFiled: December 20, 1990Date of Patent: May 26, 1998
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Modified phosphorous intermediates for providing functional groups on the 5' end of oligonucleotides
Patent number: 5726329Abstract: Phosphoramidites of the formula ##STR1## where R is a base-labile protecting group, R.sup.1 and R.sup.Type: GrantFiled: May 8, 1995Date of Patent: March 10, 1998Assignee: La Jolla Pharmaceutical CompanyInventors: David S. Jones, John P. Hachmann, Michael J. Conrad, Stephen Coutts, Douglas Alan Livingston -
Patent number: 5679700Abstract: Novel phosphinic acid-containing peptidyl compounds of formula I are found to be useful inhibitors of matrix metalloendoproteinase-mediated diseases including osteoarthritis, rheumatoid arthritis, septic arthritis, tumor invasion in certain cancers, periodontal disease, corneal ulceration, proteinuria, dystrophobic epidermolysis bullosa, and coronary thrombosis associated with atherosclerotic plaque rupture. These inhibitors may also be useful in preventing the pathological sequelae following a traumatic injury that could lead to permanent disability. These compounds may also have utility as a means for birth control by preventing ovulation or implantation.Type: GrantFiled: November 9, 1995Date of Patent: October 21, 1997Assignee: Merck & Co., Inc.Inventors: Charles G. Caldwell, Philippe L. Durette, Joung L. Goulet, William K. Hagmann, Soumya P. Sahoo