ES2183532T3 - Reacciones de copulacion con catalizadores de paladio. - Google Patents
Reacciones de copulacion con catalizadores de paladio.Info
- Publication number
- ES2183532T3 ES2183532T3 ES99913239T ES99913239T ES2183532T3 ES 2183532 T3 ES2183532 T3 ES 2183532T3 ES 99913239 T ES99913239 T ES 99913239T ES 99913239 T ES99913239 T ES 99913239T ES 2183532 T3 ES2183532 T3 ES 2183532T3
- Authority
- ES
- Spain
- Prior art keywords
- formula
- meanings defined
- olefin
- derivative
- substituents
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 title abstract 5
- 239000003054 catalyst Substances 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 title 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 8
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 8
- -1 aromatic olefin Chemical class 0.000 abstract 7
- 125000001424 substituent group Chemical group 0.000 abstract 7
- 150000001336 alkenes Chemical class 0.000 abstract 4
- 235000010290 biphenyl Nutrition 0.000 abstract 4
- 239000004305 biphenyl Substances 0.000 abstract 4
- 238000005859 coupling reaction Methods 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 229910052740 iodine Inorganic materials 0.000 abstract 3
- 239000003446 ligand Substances 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 125000000129 anionic group Chemical group 0.000 abstract 2
- 150000001543 aryl boronic acids Chemical class 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000005690 diesters Chemical class 0.000 abstract 2
- 229910052763 palladium Inorganic materials 0.000 abstract 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 239000011630 iodine Chemical group 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
Classifications
-
- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/006—Palladium 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
- 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
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
- C07C225/14—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
- C07C225/16—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
-
- 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
- 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
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
Un procedimiento de obtención de un bifenilo de la fórmula en la que A y B son sustituyentes; m y n son números enteros de 0 a 5 que definen el número de sustituyentes existentes sobre los radicales fenilo D y E; o bien de una olefina aromática de la fórmula en la que C significa sustituyentes, ¿o¿ significa un número entero de 0 a 5 que define el número de sustituyentes exis tentes sobre el radical fenilo F y R6, R7 y R8 son hidrógeno o sustituyentes, dicho procedimiento consiste a) en someter un derivado fenilo de la fórmula ((sustituir ¿or¿ por ¿o¿)) en las que X es un grupo saliente, A y B tienen los significados definidos para la fórmula I y pueden ser además un grupo saliente X adicional y m y n tienen los significados definidos para la fórmula I, a una reacción de copulación con un derivado de ácido arilborónico de la fórmula ((sustituir ¿or¿ por ¿o¿)) en las que A, B, m y n tienen los significados definidos para la fórmula I e Y es un grupo -B(OH)2 o un derivado mono- o diéster del -B(OH)2 para obtener el bifenilo (I); y b) en someter un derivado fenilo de la fórmula en la que C y ¿o¿ tienen los significados definidos para la fórmula II y X es un grupo saliente, a una reacción de copulación con una olefina de la fórmula en la que R6, R7 y R8 tienen los significados definidos para la fórmula II con el fin de obtener la olefina aromática (II), en cada caso en presencia de una cantidad catalíticamente eficaz de un compuesto complejo de paladio y olefina de la fórmula en la que L es un ligando neutro que tiene características de dador de electrones, Z es un ligando aniónico y D es un sustituyente y p es un número entero de 0 a 5 que define el número de sustituyentes existentes sobre el grupo alilo; o bien a¿) en someter un derivado fenilo (IIIa) o (IIIb), en el que X es cloro, bromo o yodo, A y B tienen los significados definidos para la fórmula I y pueden ser además un grupo saliente X adicional y m yn tienen los significados defi nidos para la fórmula I, a una reacción de copulación con un derivado de ácido arilborónico (IVa) o (IVb), en el que A, B, m y n tienen los significados definidos para la fórmula I e Y es el grupo -B(OH)2 o un derivado mono- o diéster de -B(OH)2 para obtener el bifenilo (I); o bien b¿) en someter un derivado fenilo (V), en el que C y ¿o¿ tienen los significados definidos para la fórmula II y X es bromo o yodo a una reacción de copulación con una olefina (VI) en la que R6, R7 y R8 tienen los significados definidos para la fórmula II con el fin de obtener la olefina aromática (II), en presencia de una cantidad catalíticamente eficaz de un compuesto complejo de paladio iónico y olefina de la fórmula en la que Z1 y Z2 son ligandos aniónicos y K+ es un catión no coordinante y D y p tienen los significados definidos ante riormente y en aislar el bifenilo (I) o la olefina aromática condensada (II) después de finalizar las variantes de procesoa), b), a¿) o b¿).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH64498 | 1998-03-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2183532T3 true ES2183532T3 (es) | 2003-03-16 |
Family
ID=4191818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES99913239T Expired - Lifetime ES2183532T3 (es) | 1998-03-18 | 1999-03-08 | Reacciones de copulacion con catalizadores de paladio. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6417357B1 (es) |
| EP (1) | EP1064243B1 (es) |
| JP (1) | JP2002506836A (es) |
| AU (1) | AU3144299A (es) |
| CA (1) | CA2321791A1 (es) |
| DE (1) | DE69903615T2 (es) |
| ES (1) | ES2183532T3 (es) |
| PT (1) | PT1064243E (es) |
| TW (1) | TW483883B (es) |
| WO (1) | WO1999047474A1 (es) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030220646A1 (en) * | 2002-05-23 | 2003-11-27 | Thelen Sarah L. | Method and apparatus for reducing femoral fractures |
| CN1217930C (zh) | 2000-05-26 | 2005-09-07 | 西巴特殊化学品控股有限公司 | 吲哚衍生物的制备方法和该方法的中间体 |
| DE10107227A1 (de) * | 2001-02-16 | 2002-08-29 | Clariant Gmbh | Verfahren zur Herstellung von 4-substituierten 2-Alkyl- und 2-Alkoxylbiphenylen |
| US7041280B2 (en) | 2001-06-29 | 2006-05-09 | Genzyme Corporation | Aryl boronate functionalized polymers for treating obesity |
| US6858592B2 (en) | 2001-06-29 | 2005-02-22 | Genzyme Corporation | Aryl boronic acids for treating obesity |
| JP2005503393A (ja) * | 2001-08-22 | 2005-02-03 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | インドール誘導体の製造方法 |
| JP2004043433A (ja) * | 2002-04-26 | 2004-02-12 | Kitai Kagi Kofun Yugenkoshi | モルフォリノケトン誘導体及びその用途 |
| US9923148B2 (en) | 2002-10-30 | 2018-03-20 | Udc Ireland Limited | Electroluminescent device |
| US7214825B2 (en) | 2003-10-17 | 2007-05-08 | Honeywell International Inc. | O-(3-chloropropenyl) hydroxylamine free base |
| US9109081B2 (en) * | 2005-02-16 | 2015-08-18 | Sumitomo Chemical Company, Limited | Method for producing aromatic polymer |
| US7435701B2 (en) | 2005-05-27 | 2008-10-14 | Rohm And Haas Company | Catalytic composition and its preparation and use for preparing polymers from ethylenically unsaturated monomers |
| EP1885818B2 (en) | 2005-05-30 | 2018-10-03 | UDC Ireland Limited | Electroluminescent device |
| US7425556B2 (en) * | 2005-12-20 | 2008-09-16 | Astrazeneca Ab | Compounds and uses thereof |
| US7465795B2 (en) * | 2005-12-20 | 2008-12-16 | Astrazeneca Ab | Compounds and uses thereof |
| AR067028A1 (es) * | 2007-06-19 | 2009-09-30 | Astrazeneca Ab | Compuestos y usos de los mismos 849 |
| EP2008991A1 (de) | 2007-06-29 | 2008-12-31 | Bayer CropScience AG | Verfahren zur Herstellung von Biarylen |
| JP5719528B2 (ja) * | 2009-06-09 | 2015-05-20 | 富士フイルム株式会社 | 新規なトリアジン誘導体、紫外線吸収剤及び樹脂組成物 |
| EP2585216B1 (en) | 2010-06-23 | 2019-11-20 | Johnson Matthey PLC | Pi-allylpalladium and pi-allylnickel complexes for use as catalysts in carbon-carbon and carbon-nitrogen coupling reactions |
| US9079872B2 (en) | 2010-10-07 | 2015-07-14 | Basf Se | Phenanthro[9, 10-B]furans for electronic applications |
| JP6016247B2 (ja) | 2010-10-07 | 2016-10-26 | ユー・ディー・シー アイルランド リミテッド | 電子適用のためのフェナントロ［９，１０−ｂ］フラン |
| US8362246B2 (en) | 2010-12-13 | 2013-01-29 | Basf Se | Bispyrimidines for electronic applications |
| WO2012080052A1 (en) | 2010-12-13 | 2012-06-21 | Basf Se | Bispyrimidines for electronic applications |
| KR102266455B1 (ko) | 2011-03-25 | 2021-06-21 | 유디씨 아일랜드 리미티드 | 전자장치 응용을 위한 4h-이미다조[1,2-a]이미다졸 |
| US9806270B2 (en) | 2011-03-25 | 2017-10-31 | Udc Ireland Limited | 4H-imidazo[1,2-a]imidazoles for electronic applications |
| US9502664B2 (en) | 2011-11-10 | 2016-11-22 | Udc Ireland Limited | 4H-imidazo[1,2-a]imidazoles for electronic applications |
| EP3232485A1 (en) | 2012-07-10 | 2017-10-18 | UDC Ireland Limited | Benzimidazo[1,2-a]benzimidazole derivatives for electronic applications |
| WO2014044722A1 (en) | 2012-09-20 | 2014-03-27 | Basf Se | Azadibenzofurans for electronic applications |
| US9707551B2 (en) | 2013-01-23 | 2017-07-18 | Hokko Chemical Industry Co., Ltd. | Reaction catalyst for cross-coupling and method for manufacturing aromatic compound |
| EP3063153B1 (en) | 2013-10-31 | 2018-03-07 | Idemitsu Kosan Co., Ltd. | Azadibenzothiophenes for electronic applications |
| US9231217B2 (en) | 2013-11-28 | 2016-01-05 | Semiconductor Energy Laboratory Co., Ltd. | Synthesis method of organometallic complex, synthesis method of pyrazine derivative, 5,6-diaryl-2-pyrazyl triflate, light-emitting element, light-emitting device, electronic device, and lighting device |
| EP2982676B1 (en) | 2014-08-07 | 2018-04-11 | Idemitsu Kosan Co., Ltd. | Benzimidazo[2,1-B]benzoxazoles for electronic applications |
| EP2993215B1 (en) | 2014-09-04 | 2019-06-19 | Idemitsu Kosan Co., Ltd. | Azabenzimidazo[2,1-a]benzimidazoles for electronic applications |
| US9956550B2 (en) | 2016-09-06 | 2018-05-01 | King Fahd University Of Petroleum And Minerals | Solid-supported palladium(II) complex for catalyzing Mizoroki-Heck coupling reactions and a method thereof |
| JP7023080B2 (ja) | 2016-10-31 | 2022-02-21 | 東ソー株式会社 | 芳香族化合物の製造方法 |
| CN116003273B (zh) * | 2023-02-09 | 2023-11-07 | 湖南勤润新材料有限公司 | 一种α-胺基酮类化合物、其制备方法及其在光辐射固化领域的应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9017482D0 (en) | 1990-08-09 | 1990-09-26 | Ici Plc | Manufacturing process |
| US5130439A (en) | 1991-11-18 | 1992-07-14 | Lo Young S | Tetrazolylphenylboronic acid intermediates for the synthesis of AII receptor antagonists |
| US5831107A (en) | 1994-06-22 | 1998-11-03 | Aventis Research & Technology Deutschland | Palladacycles and a process for their preparation |
| DE4421730C1 (de) | 1994-06-22 | 1995-11-23 | Hoechst Ag | Verfahren zur Herstellung von aromatischen Olefinen unter Katalyse von Palladacyclen |
| DE4423061C1 (de) * | 1994-07-01 | 1996-01-18 | Hoechst Ag | Verfahren zur Herstellung von Biphenylen mit Palladacyclen als Katalysatoren |
| DE19503119A1 (de) | 1995-02-01 | 1996-08-08 | Hoechst Ag | Verfahren zur Herstellung von aromatischen Olefinen unter Katalyse von Palladacyclen |
-
1999
- 1999-03-08 CA CA002321791A patent/CA2321791A1/en not_active Abandoned
- 1999-03-08 ES ES99913239T patent/ES2183532T3/es not_active Expired - Lifetime
- 1999-03-08 JP JP2000536672A patent/JP2002506836A/ja active Pending
- 1999-03-08 PT PT99913239T patent/PT1064243E/pt unknown
- 1999-03-08 AU AU31442/99A patent/AU3144299A/en not_active Abandoned
- 1999-03-08 EP EP99913239A patent/EP1064243B1/en not_active Expired - Lifetime
- 1999-03-08 WO PCT/EP1999/001474 patent/WO1999047474A1/en not_active Ceased
- 1999-03-08 DE DE69903615T patent/DE69903615T2/de not_active Expired - Fee Related
- 1999-03-17 TW TW088104121A patent/TW483883B/zh not_active IP Right Cessation
-
2000
- 2000-09-14 US US09/646,206 patent/US6417357B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1064243A1 (en) | 2001-01-03 |
| DE69903615D1 (de) | 2002-11-28 |
| JP2002506836A (ja) | 2002-03-05 |
| EP1064243B1 (en) | 2002-10-23 |
| DE69903615T2 (de) | 2003-06-26 |
| PT1064243E (pt) | 2003-03-31 |
| TW483883B (en) | 2002-04-21 |
| CA2321791A1 (en) | 1999-09-23 |
| WO1999047474A1 (en) | 1999-09-23 |
| US6417357B1 (en) | 2002-07-09 |
| AU3144299A (en) | 1999-10-11 |
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