CA2509522C - Ligands for metals and improved metal-catalyzed processes based thereon - Google Patents

Ligands for metals and improved metal-catalyzed processes based thereon Download PDF

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Publication number
CA2509522C
CA2509522C CA2509522A CA2509522A CA2509522C CA 2509522 C CA2509522 C CA 2509522C CA 2509522 A CA2509522 A CA 2509522A CA 2509522 A CA2509522 A CA 2509522A CA 2509522 C CA2509522 C CA 2509522C
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base
occurrence
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CA2509522A
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English (en)
French (fr)
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CA2509522A1 (en
Inventor
Stephen L. Buchwald
Xiaohua Huang
Danilo Zim
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Massachusetts Institute of Technology
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Massachusetts Institute of Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/023—Preparation; Separation; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
    • C07B37/04—Substitution
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
    • C07C1/321—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a non-metal atom
    • C07C1/322—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a non-metal atom the hetero-atom being a sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/06—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
    • C07C209/10—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/04—Formation of amino groups in compounds containing carboxyl groups
    • C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
    • C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/32—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C07C37/18—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by condensation involving halogen atoms of halogenated compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/5018—Cycloaliphatic phosphines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/5022—Aromatic phosphines (P-C aromatic linkage)

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pyridine Compounds (AREA)
  • Indole Compounds (AREA)
  • Catalysts (AREA)
CA2509522A 2002-12-09 2003-12-09 Ligands for metals and improved metal-catalyzed processes based thereon Expired - Lifetime CA2509522C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US43187002P 2002-12-09 2002-12-09
US60/431,870 2002-12-09
US45156203P 2003-03-03 2003-03-03
US60/451,562 2003-03-03
PCT/US2003/038945 WO2004052939A2 (en) 2002-12-09 2003-12-09 Ligands for metals and improved metal-catalyzed processes based thereon

Publications (2)

Publication Number Publication Date
CA2509522A1 CA2509522A1 (en) 2004-06-24
CA2509522C true CA2509522C (en) 2013-05-07

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CA2509522A Expired - Lifetime CA2509522C (en) 2002-12-09 2003-12-09 Ligands for metals and improved metal-catalyzed processes based thereon

Country Status (7)

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EP (2) EP2583958B1 (enExample)
JP (1) JP5138890B2 (enExample)
KR (1) KR20050085473A (enExample)
AU (1) AU2003296326A1 (enExample)
CA (1) CA2509522C (enExample)
DK (2) DK1581467T3 (enExample)
WO (1) WO2004052939A2 (enExample)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4857546B2 (ja) * 2004-11-02 2012-01-18 三菱化学株式会社 トリアリールアミン化合物の製造方法
US7560596B2 (en) 2005-01-10 2009-07-14 Massachusetts Institute Of Technology Transition-metal-catalyzed carbon-nitrogen and carbon-carbon bond-forming reactions
DE102005016344A1 (de) * 2005-04-09 2006-10-12 Lanxess Deutschland Gmbh Verfahren zur Herstellung von Diarylbenzidinen
DE102005046344A1 (de) 2005-09-28 2007-03-29 Saltigo Gmbh Verfahren zur Kupplung von Benzylaminen mit Halogenaromaten
US8288604B2 (en) 2006-08-25 2012-10-16 Gifu University Method of rapid methylation, kit for preparing PET tracer and method of producing PET tracer
JP5124210B2 (ja) * 2007-08-24 2013-01-23 日本化学工業株式会社 ビアリールホスフィン化合物の製造方法
CN101952298B (zh) 2007-12-12 2015-06-17 麻省理工学院 用于过渡金属催化的交联偶合反应的配体及其使用方法
FR2926297B1 (fr) * 2008-01-10 2013-03-08 Centre Nat Rech Scient Molecules chimiques inhibitrices du mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage.
EP2311788A1 (en) 2009-10-14 2011-04-20 Intitut Català d'Investigació Química (ICIQ) Process for the carboxylation of aryl halides with palladium catalysts
JP5688808B2 (ja) 2009-12-04 2015-03-25 独立行政法人理化学研究所 高速フルオロメチル化法及びそれを利用したｐｅｔトレーサーの製造方法
JP5568976B2 (ja) * 2009-12-16 2014-08-13 東ソー株式会社 多置換ホスフィン化合物及び該ホスフィン化合物を含む触媒
US9096626B2 (en) 2010-04-05 2015-08-04 Boehringer Ingelheim International Gmbh Monophosphorus ligands and their use in cross-coupling reactions
UA113498C2 (xx) 2010-07-16 2017-02-10 Фосфінові ліганди для каталітичних реакцій
US9255074B2 (en) 2010-07-16 2016-02-09 Abbvie Inc. Process for preparing antiviral compounds
US8975443B2 (en) 2010-07-16 2015-03-10 Abbvie Inc. Phosphine ligands for catalytic reactions
SG10201505540SA (en) 2010-07-16 2015-08-28 Abbott Lab Process for preparing antiviral compounds
CN104684959A (zh) * 2012-07-06 2015-06-03 住友化学株式会社 芳香族化合物的制备方法
JP6001433B2 (ja) * 2012-12-05 2016-10-05 キヤノンファインテック株式会社 アリールアミン化合物の製造方法
JP2014196274A (ja) * 2013-03-29 2014-10-16 三井化学株式会社 多環芳香族炭化水素の誘導体の製造方法
BR112016000968B1 (pt) * 2013-07-23 2021-05-18 Bayer Cropscience Aktiengesellschaft processo para a preparação de bifenilanilidas halogenadas
JP7041092B2 (ja) 2019-04-05 2022-03-23 日本化学工業株式会社 ビアリールホスフィンの製造方法
CN114945552A (zh) 2019-07-19 2022-08-26 阿达玛马克西姆有限公司 制备联苯胺的方法
CN111440213B (zh) * 2020-04-07 2022-10-25 西安近代化学研究所 一种过渡金属催化芳香硝基c-no2转化为c-p键方法
CN112939716B (zh) * 2021-02-01 2023-01-06 三峡大学 一种联苯类化合物的制备方法
CN113231060B (zh) * 2021-05-10 2023-03-10 中国科学技术大学 一种金属间化合物复合材料及其制备方法和应用
CN116375787B (zh) * 2023-04-06 2025-02-28 宁波大学 一种甾体衍生的手性单硼路易酸催化剂及其合成方法和应用

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4631211A (en) 1985-03-25 1986-12-23 Scripps Clinic & Research Foundation Means for sequential solid phase organic synthesis and methods using the same
US5143854A (en) 1989-06-07 1992-09-01 Affymax Technologies N.V. Large scale photolithographic solid phase synthesis of polypeptides and receptor binding screening thereof
EP0502060A4 (en) 1989-11-13 1993-05-05 Affymax Technologies N.V. Spatially-addressable immobilization of anti-ligands on surfaces
EP0562025B1 (en) 1990-12-06 2001-02-07 Affymetrix, Inc. (a Delaware Corporation) Compounds and their use in a binary synthesis strategy
WO1993009668A1 (en) 1991-11-22 1993-05-27 Affymax Technology N.V. Combinatorial strategies for polymer synthesis
EP0553778B1 (de) * 1992-01-31 2001-12-12 F. Hoffmann-La Roche Ag Asymmetrische Hydrierung
US5359115A (en) 1992-03-26 1994-10-25 Affymax Technologies, N.V. Methods for the synthesis of phosphonate esters
US5573905A (en) 1992-03-30 1996-11-12 The Scripps Research Institute Encoded combinatorial chemical libraries
US5288514A (en) 1992-09-14 1994-02-22 The Regents Of The University Of California Solid phase and combinatorial synthesis of benzodiazepine compounds on a solid support
PT665897E (pt) 1992-10-01 2003-11-28 Trustees Of Columbia U In The Bibliotecas quimicas combinatorias complexas codificadas com etiquetas
US5480971A (en) 1993-06-17 1996-01-02 Houghten Pharmaceuticals, Inc. Peralkylated oligopeptide mixtures
US5440016A (en) 1993-06-18 1995-08-08 Torrey Pines Institute For Molecular Studies Peptides of the formula (KFmoc) ZZZ and their uses
US5362899A (en) 1993-09-09 1994-11-08 Affymax Technologies, N.V. Chiral synthesis of alpha-aminophosponic acids
ATE177427T1 (de) * 1993-10-08 1999-03-15 Hoffmann La Roche Optisch aktive phosphorverbindungen
DE4435189A1 (de) * 1994-09-30 1996-04-04 Hoechst Ag Neue sulfonierte Phosphine, Verfahren zu ihrer Herstellung und ihre Verwendung als Bestandteil von Katalysatorsystemen
DE69935933T2 (de) * 1998-07-10 2008-01-10 Massachusetts Institute Of Technology, Cambridge Liganden für Metalle und verbesserte Metall-katalysierte Verfahren, die darauf basieren
US6395916B1 (en) * 1998-07-10 2002-05-28 Massachusetts Institute Of Technology Ligands for metals and improved metal-catalyzed processes based thereon
JP3793035B2 (ja) * 2000-04-14 2006-07-05 キヤノン株式会社 電子写真感光体、該電子写真感光体を有するプロセスカートリッジおよび電子写真装置、該電子写真感光体の製造方法
DE10051316A1 (de) * 2000-10-17 2002-04-25 Omg Ag & Co Kg Verfahren zur Herstellung von mono-, bi- oder polyfunktionellen Biarylen
WO2003006420A1 (en) * 2001-07-12 2003-01-23 Yale University Catalytic method to convert aryl compounds to aryl amines
JP4270365B2 (ja) * 2002-02-07 2009-05-27 富士フイルム株式会社 芳香族縮環化合物の製造方法

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Publication number Publication date
EP2583958B1 (en) 2016-08-10
DK1581467T3 (en) 2016-11-28
EP1581467A4 (en) 2008-08-13
CA2509522A1 (en) 2004-06-24
EP1581467A2 (en) 2005-10-05
JP5138890B2 (ja) 2013-02-06
JP2006509046A (ja) 2006-03-16
WO2004052939A2 (en) 2004-06-24
AU2003296326A1 (en) 2004-06-30
AU2003296326A8 (en) 2004-06-30
DK2583958T3 (en) 2016-11-28
EP1581467B1 (en) 2016-10-12
KR20050085473A (ko) 2005-08-29
EP2583958A1 (en) 2013-04-24
WO2004052939A3 (en) 2004-12-16

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