AU2001280028A1 - Catalytic hydrogenation processes - Google Patents
Catalytic hydrogenation processesInfo
- Publication number
- AU2001280028A1 AU2001280028A1 AU2001280028A AU8002801A AU2001280028A1 AU 2001280028 A1 AU2001280028 A1 AU 2001280028A1 AU 2001280028 A AU2001280028 A AU 2001280028A AU 8002801 A AU8002801 A AU 8002801A AU 2001280028 A1 AU2001280028 A1 AU 2001280028A1
- Authority
- AU
- Australia
- Prior art keywords
- line
- formulae
- catalytic hydrogenation
- phosphino
- hydrogenation processes
- 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.)
- Abandoned
Links
- 238000009903 catalytic hydrogenation reaction Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- XQJHRCVXRAJIDY-UHFFFAOYSA-N aminophosphine Chemical compound PN XQJHRCVXRAJIDY-UHFFFAOYSA-N 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000003446 ligand Substances 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/189—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms containing both nitrogen and phosphorus as complexing atoms, including e.g. phosphino moieties, in one at least bidentate or bridging ligand
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B41/00—Formation or introduction of functional groups containing oxygen
- C07B41/02—Formation or introduction of functional groups containing oxygen of hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B43/00—Formation or introduction of functional groups containing nitrogen
- C07B43/04—Formation or introduction of functional groups containing nitrogen of amino groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/52—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of imines or imino-ethers
-
- 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
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
-
- 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
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
- C07C29/145—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones with hydrogen or hydrogen-containing gases
-
- 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
- C07F15/0046—Ruthenium compounds
-
- 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
- C07F15/0046—Ruthenium compounds
- C07F15/0053—Ruthenium compounds without a metal-carbon linkage
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/60—Reduction reactions, e.g. hydrogenation
- B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
- B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
- B01J2231/643—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of R2C=O or R2C=NR (R= C, H)
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/821—Ruthenium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US23214400P | 2000-09-13 | 2000-09-13 | |
US60/232,144 | 2000-09-13 | ||
IB0001303 | 2000-09-13 | ||
IBPCT/IB00/01303 | 2000-09-13 | ||
PCT/IB2001/001657 WO2002022526A2 (fr) | 2000-09-13 | 2001-09-11 | Procedes d'hydrogenation catalytique |
Publications (1)
Publication Number | Publication Date |
---|---|
AU2001280028A1 true AU2001280028A1 (en) | 2002-03-26 |
Family
ID=26318616
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU2001280028A Abandoned AU2001280028A1 (en) | 2000-09-13 | 2001-09-11 | Catalytic hydrogenation processes |
Country Status (10)
Country | Link |
---|---|
US (2) | US7317131B2 (fr) |
EP (1) | EP1366004B1 (fr) |
JP (2) | JP5345270B2 (fr) |
AT (1) | ATE395314T1 (fr) |
AU (1) | AU2001280028A1 (fr) |
CA (1) | CA2422029C (fr) |
DE (1) | DE60134052D1 (fr) |
ES (1) | ES2305095T3 (fr) |
IL (2) | IL154822A0 (fr) |
WO (1) | WO2002022526A2 (fr) |
Families Citing this family (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7256311B2 (en) * | 2002-05-15 | 2007-08-14 | Kamaluddin Abdur-Rashid | Process for hydrogenating unactivated imines using ruthenium complexes as catalysts |
CN100384791C (zh) * | 2002-12-02 | 2008-04-30 | 索尔维亚斯股份公司 | 碳-杂原子双键的催化氢化 |
JP4704812B2 (ja) * | 2004-06-09 | 2011-06-22 | エム. カレイラ エリック | モノホスフィン化合物、その遷移金属錯体および該錯体を不斉触媒として用いる光学活性化合物の製造方法 |
RU2007140871A (ru) | 2005-04-05 | 2009-05-20 | Фирмениш Са (Ch) | Гидрирование сложных эфиров с комплексами ru с бидентатными лигандами |
US7989665B2 (en) | 2005-04-05 | 2011-08-02 | Firmenich Sa | Hydrogenation of esters with Ru/tetradentate ligands complexes |
BRPI0608687A2 (pt) | 2005-04-05 | 2016-11-08 | Firmenich & Cie | processo para a redução de um substrato, ligando, e, complexo |
WO2007082928A2 (fr) * | 2006-01-23 | 2007-07-26 | Basf Se | Procédé de fabrication d'un catalyseur au ruthénium |
JP2007314433A (ja) * | 2006-05-23 | 2007-12-06 | Univ Of Tokyo | 光学活性三級ホスフィン化合物、これを配位子とする金属錯体およびその用途 |
CN100465144C (zh) * | 2006-12-01 | 2009-03-04 | 华南理工大学 | 一种负载型非晶态含钌硼催化剂催化加氢还原羰基化合物制备醇的方法 |
CA2591126A1 (fr) | 2007-06-08 | 2008-12-08 | Kanata Chemical Technologies Inc. | Procede de preparation de ligands d'aminophosphine et leur utilisation dans des catalyseurs metalliques |
CA2690437C (fr) * | 2007-07-06 | 2015-09-08 | Kanata Chemical Technologies Inc. | Procede de preparation du cis-4-tert.-butylcyclohexanol |
US7772445B2 (en) | 2007-07-06 | 2010-08-10 | Kanata Chemical Technologies Inc. | Ruthenium catalysts for catalytic hydrogenation |
WO2009053883A1 (fr) | 2007-10-23 | 2009-04-30 | Firmenich Sa | Procédé pour la préparation de dérivés de tétranorlabdane |
US20100311975A1 (en) * | 2007-10-30 | 2010-12-09 | Kamaluddin Abdur-Rashid | Cationic transition metal catalysts |
US7615671B2 (en) | 2007-11-30 | 2009-11-10 | Eastman Chemical Company | Hydrogenation process for the preparation of 1,2-diols |
JP5451209B2 (ja) | 2008-07-08 | 2014-03-26 | 国立大学法人東京工業大学 | エステル類およびラクトン類の実用的な還元方法 |
CA2740500C (fr) | 2008-10-17 | 2018-06-12 | Kanata Chemical Technologies Inc. | Procede pour preparer un catalyseur metallique |
CN102227261A (zh) | 2008-11-28 | 2011-10-26 | 弗门尼舍有限公司 | 用具有二胺和磷-氮二齿配体的钌络合物进行的酯、酮或醛基的氢化 |
EP2236487B1 (fr) | 2009-04-02 | 2015-09-02 | International Flavors & Fragrances Inc. | Procédé de production de levosandal |
US8038855B2 (en) * | 2009-04-29 | 2011-10-18 | Freeport-Mcmoran Corporation | Anode structure for copper electrowinning |
WO2012084810A1 (fr) | 2010-12-21 | 2012-06-28 | Firmenich Sa | Hydrogénation de groupes esters ou carbonyles avec des complexes du ruthénium à base d'amino/imino-thioéther tétradentate |
ES2710448T3 (es) | 2011-10-06 | 2019-04-25 | Firmenich & Cie | Hidrogenacion selectiva de aldehido con complejos de Ru/ligandos bidentados |
CN105073696B (zh) * | 2013-03-15 | 2018-06-05 | 弗门尼舍有限公司 | 用钌/双齿配体络合物进行的醛的选择性氢化 |
GB201509664D0 (en) * | 2015-06-03 | 2015-07-15 | Johnson Matthey Plc And Universit Di Udine | Process |
WO2019193483A1 (fr) | 2018-04-06 | 2019-10-10 | Kamal Pharmachem Inc. | Conversion catalytique du dioxyde de carbone en méthanol |
CN109553509A (zh) * | 2018-12-17 | 2019-04-02 | 西安近代化学研究所 | 一种2,2,3,3,3-五氟丙醇的制备方法 |
Family Cites Families (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2739254B2 (ja) * | 1990-10-01 | 1998-04-15 | 高砂香料工業株式会社 | イリジウム―光学活性ホスフィン錯体及びこれを用いた光学活性アルコールの製造方法 |
FR2693190B1 (fr) * | 1992-07-02 | 1994-09-23 | Elf Aquitaine | Procédé d'hydrogénation énantiosélectif de la double liaison C=O OXO. |
JP2731377B2 (ja) * | 1994-12-07 | 1998-03-25 | 科学技術振興事業団 | 光学活性アルコール類の製造方法 |
EP0718265B1 (fr) * | 1994-12-07 | 2000-08-23 | Nkk Corporation | Procédé pour la préparation d'un alcool |
JP2935453B2 (ja) * | 1994-12-07 | 1999-08-16 | 科学技術振興事業団 | アルコール類の製造方法 |
JP2912572B2 (ja) * | 1995-12-06 | 1999-06-28 | 科学技術振興事業団 | 光学活性アミン類の製造方法 |
JP2962668B2 (ja) * | 1995-12-06 | 1999-10-12 | 科学技術振興事業団 | 光学活性アルコール類の製造方法 |
EP1300381B1 (fr) * | 1995-12-06 | 2006-03-08 | Japan Science and Technology Agency | Procédé pour la préparation d'alcools optiquement actifs |
DE19548399A1 (de) * | 1995-12-22 | 1997-06-26 | Basf Ag | Rutheniumkomplexe mit einem chiralen, zweizähnigen Phosphinoxazolin-Liganden zur enantioselektiven Transferhydrierung von prochiralen Ketonen |
JP3771615B2 (ja) * | 1995-12-28 | 2006-04-26 | 高砂香料工業株式会社 | 光学活性ベンズヒドロール化合物の製造方法 |
JPH09241194A (ja) * | 1996-03-07 | 1997-09-16 | Takasago Internatl Corp | シス−4−t−ブチルシクロヘキサノールの製造法 |
JPH10273456A (ja) * | 1997-03-31 | 1998-10-13 | Kagaku Gijutsu Shinko Jigyodan | 光学活性アルコール類の製造方法 |
CN1047597C (zh) * | 1997-06-02 | 1999-12-22 | 厦门大学 | 手性胺膦金属配合物及其制备方法和在不对称催化氢化的应用 |
JP4144814B2 (ja) * | 1997-09-05 | 2008-09-03 | 長谷川香料株式会社 | 光学活性アルコール化合物の製造方法 |
JPH11124350A (ja) * | 1997-10-21 | 1999-05-11 | Mitsubishi Chemical Corp | 光学活性アルコールの製造方法 |
JP4004123B2 (ja) * | 1997-12-26 | 2007-11-07 | 独立行政法人科学技術振興機構 | ルテニウム錯体を触媒とするアルコール化合物の製造方法 |
JP2000026344A (ja) * | 1998-07-01 | 2000-01-25 | Ryoji Noyori | 光学活性な1−(4−イソブチルフェニル)ブタン−1−オールの製造方法 |
JP3771070B2 (ja) * | 1998-12-24 | 2006-04-26 | 高砂香料工業株式会社 | 軸不斉化合物の製造方法、その製造中間体、新規な軸不斉化合物を配位子とする遷移金属錯体、不斉水素化触媒及び不斉炭素−炭素結合形成触媒 |
JP2001294594A (ja) * | 2000-02-10 | 2001-10-23 | Toray Ind Inc | ホスフィン含有アミノ化合物、その製造方法、ルテニウム錯体およびアルコールの製造方法 |
US6878852B2 (en) * | 2000-11-17 | 2005-04-12 | Firmenich Sa | Process for hydrogenation of carbonyl and iminocarbonyl compounds using ruthenium catalysts comprising tetradentate diimino-diphosphine ligands |
-
2001
- 2001-09-11 WO PCT/IB2001/001657 patent/WO2002022526A2/fr active IP Right Grant
- 2001-09-11 EP EP01958310A patent/EP1366004B1/fr not_active Expired - Lifetime
- 2001-09-11 AU AU2001280028A patent/AU2001280028A1/en not_active Abandoned
- 2001-09-11 CA CA002422029A patent/CA2422029C/fr not_active Expired - Fee Related
- 2001-09-11 AT AT01958310T patent/ATE395314T1/de not_active IP Right Cessation
- 2001-09-11 DE DE60134052T patent/DE60134052D1/de not_active Expired - Lifetime
- 2001-09-11 US US10/380,483 patent/US7317131B2/en not_active Expired - Lifetime
- 2001-09-11 IL IL15482201A patent/IL154822A0/xx unknown
- 2001-09-11 JP JP2002526727A patent/JP5345270B2/ja not_active Expired - Fee Related
- 2001-09-11 ES ES01958310T patent/ES2305095T3/es not_active Expired - Lifetime
-
2003
- 2003-03-09 IL IL154822A patent/IL154822A/en not_active IP Right Cessation
-
2007
- 2007-08-08 US US11/835,868 patent/US7579295B2/en not_active Expired - Fee Related
-
2011
- 2011-12-05 JP JP2011266106A patent/JP2012087138A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
US20040063966A1 (en) | 2004-04-01 |
ATE395314T1 (de) | 2008-05-15 |
IL154822A (en) | 2009-11-18 |
JP2012087138A (ja) | 2012-05-10 |
EP1366004B1 (fr) | 2008-05-14 |
WO2002022526A3 (fr) | 2003-09-12 |
IL154822A0 (en) | 2003-10-31 |
EP1366004A2 (fr) | 2003-12-03 |
US20050245748A9 (en) | 2005-11-03 |
JP2004509087A (ja) | 2004-03-25 |
DE60134052D1 (de) | 2008-06-26 |
CA2422029A1 (fr) | 2002-03-21 |
CA2422029C (fr) | 2008-11-18 |
US7579295B2 (en) | 2009-08-25 |
WO2002022526A2 (fr) | 2002-03-21 |
US7317131B2 (en) | 2008-01-08 |
US20080015376A1 (en) | 2008-01-17 |
JP5345270B2 (ja) | 2013-11-20 |
ES2305095T3 (es) | 2008-11-01 |
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