AR045217A1 - Sintesis regioselectiva de un ester de rapamicina (cci - 779) y compuestos intermediarios relacionados. - Google Patents
Sintesis regioselectiva de un ester de rapamicina (cci - 779) y compuestos intermediarios relacionados.Info
- Publication number
- AR045217A1 AR045217A1 ARP040102778A ARP040102778A AR045217A1 AR 045217 A1 AR045217 A1 AR 045217A1 AR P040102778 A ARP040102778 A AR P040102778A AR P040102778 A ARP040102778 A AR P040102778A AR 045217 A1 AR045217 A1 AR 045217A1
- Authority
- AR
- Argentina
- Prior art keywords
- rapamycin
- ester
- silyl
- alkynyl
- alkenyl
- Prior art date
Links
- 229960002930 sirolimus Drugs 0.000 title abstract 8
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 title abstract 7
- -1 RAPAMYCIN ESTER Chemical class 0.000 title abstract 5
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 abstract 5
- 125000003342 alkenyl group Chemical group 0.000 abstract 3
- 125000000304 alkynyl group Chemical group 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000004849 alkoxymethyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 229910052796 boron Inorganic materials 0.000 abstract 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 abstract 1
- 150000002009 diols Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 abstract 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/08—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/18—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains four or more hetero 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
La presente se refiere a síntesis regio selectiva de un éster de rapamicina. Se proveen también productos intermediarios. Reivindicación 1: Un proceso para preparar un 42-éster de rapamicina, que comprende: (a) acilar un 31-silil éter de rapamicina con un compuesto de fórmula HOOC:CR7R8R9 o uno de sus anhídridos mixtos, en los cuales: R7 es H, alquilo C1-6, alquenilo C2-7, alquinilo C2-7, -(CR12R13)fOR10, -CF3, -F, o -CO2R10; R10 es H, alquilo C1-6, alquenilo C2-7, alquinilo C2-7, trifenilmetilo, bencilo, alcoximetilo C2-7, cloroetilo o tetrahidropiranilo; R8 y R9 se toman juntos para formar X; X es un 2-fenil-1,3,2-dioxaborinan-5-ilo o un 2-fenil-1,3,2-dioxaborinan-4-ilo, en los cuales el fenilo puede estar sustituido en forma opcional; R12 y R13 son, cada uno en forma independiente, H, alquilo C1-6, alquenilo C2-7, alquinilo C2-7, trifluorometilo o -F; y f = 0-6; para dar un 42-éster boronato 31-silil éter de rapamicina; (b) hidrolizar en forma selectiva el 42-éster boronato 31-silil éter en condiciones levemente ácidas para dar un 42-éster boronato de rapamicina; y (c) tratar el 42-éster boronato de rapamicina con un diol apropiado para dar un 42-éster de rapamicina.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49324903P | 2003-08-07 | 2003-08-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR045217A1 true AR045217A1 (es) | 2005-10-19 |
Family
ID=34193170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP040102778A AR045217A1 (es) | 2003-08-07 | 2004-08-04 | Sintesis regioselectiva de un ester de rapamicina (cci - 779) y compuestos intermediarios relacionados. |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US7153957B2 (es) |
| EP (1) | EP1658295B1 (es) |
| JP (1) | JP4227649B2 (es) |
| KR (1) | KR20060057605A (es) |
| CN (1) | CN1829722B (es) |
| AR (1) | AR045217A1 (es) |
| AT (1) | ATE365169T1 (es) |
| AU (1) | AU2004265267A1 (es) |
| BR (1) | BRPI0412667A (es) |
| CA (1) | CA2532988A1 (es) |
| CO (1) | CO5650251A2 (es) |
| CR (1) | CR8189A (es) |
| DE (1) | DE602004007145T2 (es) |
| DK (1) | DK1658295T3 (es) |
| EC (1) | ECSP066413A (es) |
| ES (1) | ES2287772T3 (es) |
| IL (1) | IL173134A0 (es) |
| MX (1) | MXPA06000951A (es) |
| NO (1) | NO20060494L (es) |
| PL (1) | PL1658295T3 (es) |
| PT (1) | PT1658295E (es) |
| RU (1) | RU2339639C2 (es) |
| TW (1) | TW200508241A (es) |
| UA (1) | UA83245C2 (es) |
| WO (1) | WO2005016935A2 (es) |
| ZA (1) | ZA200601055B (es) |
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| WO2002085908A1 (en) | 2001-04-24 | 2002-10-31 | Purdue Research Foundation | Folate mimetics and folate-receptor binding conjugates thereof |
| CA2484640C (en) * | 2002-05-15 | 2012-01-17 | Endocyte, Inc. | Vitamin-mitomycin conjugates |
| AU2003254168A1 (en) | 2002-07-30 | 2004-02-16 | Wyeth | Parenteral formulations containing a rapamycin hydroxyester |
| JP5576007B2 (ja) | 2003-01-27 | 2014-08-20 | エンドサイト・インコーポレイテッド | ビタミン受容体結合性薬剤送達結合体 |
| AU2004270154A1 (en) * | 2003-09-03 | 2005-03-17 | Wyeth | Amorphous rapamycin 42-ester with 3-hydroxy-2-(hydroxymethyl)-2-methylpropionic acid and its pharmaceutical compositions containing the same |
| DK1701698T3 (da) * | 2004-01-08 | 2008-05-05 | Wyeth Corp | Direkte komprimerbart farmaceutisk præparat til oral indgivelse af CCI-779 |
| EP1737869A1 (en) | 2004-04-14 | 2007-01-03 | Wyeth a Corporation of the State of Delaware | Regiospecific synthesis of rapamycin 42-ester derivatives |
| CA2564811A1 (en) | 2004-04-14 | 2005-10-27 | Wyeth | Proline cci-779 (proline-rapamycin 42-ester with 2,2-bis (hydroxymethyl) propionic acid) and two-step enzymatic synthesis of proline cci-779 and cci-779 using microbial lipase |
| ES2313328T3 (es) | 2004-04-14 | 2009-03-01 | Wyeth | Procedimiento para la preparacion de 42-esteres de rapamicina y 32-esteres de fk-506 con acido dicarboxilico, precursores para conjugados de rapamicina y anticuerpos. |
| JP2007534337A (ja) * | 2004-04-27 | 2007-11-29 | ワイス | ラパマイシン特異的メチラーゼを用いるラパマイシンの標識 |
| JP5149620B2 (ja) * | 2004-07-23 | 2013-02-20 | エンドサイト，インコーポレイテッド | ２価リンカーおよびその結合体 |
| SV2006002188A (es) | 2004-08-10 | 2006-03-15 | Wyeth Corp | Derivados de cci - 779 y metodos para su preparacion ref. am-101759salvo |
| WO2006050461A1 (en) | 2004-10-28 | 2006-05-11 | Wyeth | Use of an mtor inhibitor in treatment of uterine leiomyoma |
| EP1856130A1 (en) | 2005-02-09 | 2007-11-21 | Wyeth a Corporation of the State of Delaware | Cci-779 polymorph and use thereof |
| EP1853612A1 (en) | 2005-03-02 | 2007-11-14 | Wyeth | Purification of rapamycin |
| WO2006093743A1 (en) * | 2005-03-02 | 2006-09-08 | Wyeth | Recovery of cci-779 from mother liquors |
| WO2006101845A2 (en) | 2005-03-16 | 2006-09-28 | Endocyte, Inc. | Synthesis and purification of pteroic acid and conjugates thereof |
| JP2009504783A (ja) * | 2005-08-19 | 2009-02-05 | エンドサイト，インコーポレイテッド | ビンカアルカロイド、類似体および誘導体のリガンド結合体 |
| EP2374480A3 (en) | 2005-08-19 | 2013-05-01 | Endocyte, Inc. | Mutli-drug ligand conjugates |
| WO2007056175A2 (en) * | 2005-11-04 | 2007-05-18 | Wyeth | 41-methoxy isotope labeled rapamycin 42-ester |
| BRPI0618042A2 (pt) | 2005-11-04 | 2011-08-16 | Wyeth Corp | usos de uma rapamicina e de uma herceptina, produto, pacote farmacêutico, e, composição farmacêutica |
| RU2008120712A (ru) * | 2005-12-07 | 2010-01-20 | Вайет (Us) | Способы получения кристаллического рапамицина и определения кристалличности соединений рапамицина при помощи дифференциальной сканирующей калориметрии |
| RU2008120670A (ru) | 2005-12-07 | 2010-01-20 | Вайет (Us) | Масштабируемый способ получения 42-сложного эфира рапамицина из 42-сложного эфира рапамицина бороната |
| KR20080077618A (ko) * | 2005-12-07 | 2008-08-25 | 와이어쓰 | 정제된 결정체 ｃｃｉ-779 의 제조 방법 |
| EP1962819A1 (en) * | 2005-12-20 | 2008-09-03 | Wyeth | Control of cci-779 dosage form stability through control of drug substance impurities |
| US20070203169A1 (en) * | 2006-02-28 | 2007-08-30 | Zhao Jonathon Z | Isomers and 42-epimers of rapamycin ester analogs, methods of making and using the same |
| TW200824713A (en) * | 2006-10-18 | 2008-06-16 | Wyeth Corp | Processes for the synthesis of individual isomers of mono-PEG CCI-779 |
| US20080276935A1 (en) | 2006-11-20 | 2008-11-13 | Lixiao Wang | Treatment of asthma and chronic obstructive pulmonary disease with anti-proliferate and anti-inflammatory drugs |
| US8414525B2 (en) | 2006-11-20 | 2013-04-09 | Lutonix, Inc. | Drug releasing coatings for medical devices |
| US8414526B2 (en) | 2006-11-20 | 2013-04-09 | Lutonix, Inc. | Medical device rapid drug releasing coatings comprising oils, fatty acids, and/or lipids |
| US9700704B2 (en) | 2006-11-20 | 2017-07-11 | Lutonix, Inc. | Drug releasing coatings for balloon catheters |
| US8425459B2 (en) | 2006-11-20 | 2013-04-23 | Lutonix, Inc. | Medical device rapid drug releasing coatings comprising a therapeutic agent and a contrast agent |
| US20080175887A1 (en) | 2006-11-20 | 2008-07-24 | Lixiao Wang | Treatment of Asthma and Chronic Obstructive Pulmonary Disease With Anti-proliferate and Anti-inflammatory Drugs |
| US8414910B2 (en) | 2006-11-20 | 2013-04-09 | Lutonix, Inc. | Drug releasing coatings for medical devices |
| US9737640B2 (en) | 2006-11-20 | 2017-08-22 | Lutonix, Inc. | Drug releasing coatings for medical devices |
| US8998846B2 (en) | 2006-11-20 | 2015-04-07 | Lutonix, Inc. | Drug releasing coatings for balloon catheters |
| US20100104626A1 (en) * | 2007-02-16 | 2010-04-29 | Endocyte, Inc. | Methods and compositions for treating and diagnosing kidney disease |
| NZ580132A (en) * | 2007-03-14 | 2012-11-30 | Endocyte Inc | Binding ligand linked drug delivery conjugates of tubulysins to vitamins |
| TW200845960A (en) * | 2007-04-05 | 2008-12-01 | Wyeth Corp | Wortmannin-rapalog conjugate and uses thereof |
| TW200901989A (en) * | 2007-04-10 | 2009-01-16 | Wyeth Corp | Anti-tumor activity of CCI-779 in papillary renal cell cancer |
| CN104383553A (zh) | 2007-06-25 | 2015-03-04 | 恩多塞特公司 | 含有亲水性间隔区接头的共轭物 |
| US9877965B2 (en) | 2007-06-25 | 2018-01-30 | Endocyte, Inc. | Vitamin receptor drug delivery conjugates for treating inflammation |
| WO2009055562A1 (en) | 2007-10-25 | 2009-04-30 | Endocyte, Inc. | Tubulysins and processes for preparing |
| WO2010024898A2 (en) | 2008-08-29 | 2010-03-04 | Lutonix, Inc. | Methods and apparatuses for coating balloon catheters |
| WO2011051960A2 (en) | 2009-09-25 | 2011-05-05 | Cadila Healthcare Limited | Process for the preparation of rapamycin derivatives |
| AU2011210227A1 (en) * | 2010-01-28 | 2012-08-30 | Fresenius Kabi Oncology Ltd. | Process for the preparation of Temsirolimus and its intermediates |
| CN102020661B (zh) * | 2011-01-07 | 2013-02-13 | 天津市炜杰科技有限公司 | 一种驮瑞塞尔合成方法 |
| CN102020662B (zh) | 2011-01-07 | 2013-02-13 | 天津市炜杰科技有限公司 | 一种驮瑞塞尔制备方法 |
| EP2694520A1 (en) * | 2011-04-01 | 2014-02-12 | Sandoz AG | Regioselective acylation of rapamycin at the c-42 position |
| US10080805B2 (en) | 2012-02-24 | 2018-09-25 | Purdue Research Foundation | Cholecystokinin B receptor targeting for imaging and therapy |
| US20140080175A1 (en) | 2012-03-29 | 2014-03-20 | Endocyte, Inc. | Processes for preparing tubulysin derivatives and conjugates thereof |
| JP2015536323A (ja) | 2012-10-16 | 2015-12-21 | エンドサイト・インコーポレイテッドＥｎｄｏｃｙｔｅ， Ｉｎｃ． | 非天然アミノ酸を含む薬物送達結合体および使用方法 |
| CN104086564B (zh) * | 2014-07-30 | 2019-02-05 | 江苏奥赛康药业股份有限公司 | 一种高纯度坦罗莫司的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5362718A (en) * | 1994-04-18 | 1994-11-08 | American Home Products Corporation | Rapamycin hydroxyesters |
| DE19857765A1 (de) * | 1998-12-15 | 2000-06-21 | Clariant Gmbh | Verfahren zur Herstellung von para-Oxadiazolyl-phenyl-boronsäuren |
| US6277983B1 (en) * | 2000-09-27 | 2001-08-21 | American Home Products Corporation | Regioselective synthesis of rapamycin derivatives |
-
2004
- 2004-07-15 PT PT04778398T patent/PT1658295E/pt unknown
- 2004-07-15 KR KR1020067002610A patent/KR20060057605A/ko not_active Ceased
- 2004-07-15 MX MXPA06000951A patent/MXPA06000951A/es active IP Right Grant
- 2004-07-15 EP EP04778398A patent/EP1658295B1/en not_active Expired - Lifetime
- 2004-07-15 AU AU2004265267A patent/AU2004265267A1/en not_active Abandoned
- 2004-07-15 DE DE602004007145T patent/DE602004007145T2/de not_active Expired - Fee Related
- 2004-07-15 UA UAA200602447A patent/UA83245C2/ru unknown
- 2004-07-15 RU RU2006106910/04A patent/RU2339639C2/ru not_active IP Right Cessation
- 2004-07-15 BR BRPI0412667-0A patent/BRPI0412667A/pt not_active IP Right Cessation
- 2004-07-15 CN CN2004800217944A patent/CN1829722B/zh not_active Expired - Fee Related
- 2004-07-15 PL PL04778398T patent/PL1658295T3/pl unknown
- 2004-07-15 ES ES04778398T patent/ES2287772T3/es not_active Expired - Lifetime
- 2004-07-15 JP JP2006522574A patent/JP4227649B2/ja not_active Expired - Fee Related
- 2004-07-15 DK DK04778398T patent/DK1658295T3/da active
- 2004-07-15 WO PCT/US2004/022860 patent/WO2005016935A2/en not_active Ceased
- 2004-07-15 AT AT04778398T patent/ATE365169T1/de not_active IP Right Cessation
- 2004-07-15 CA CA002532988A patent/CA2532988A1/en not_active Abandoned
- 2004-07-30 US US10/903,062 patent/US7153957B2/en not_active Expired - Fee Related
- 2004-08-04 AR ARP040102778A patent/AR045217A1/es unknown
- 2004-08-05 TW TW093123422A patent/TW200508241A/zh unknown
-
2006
- 2006-01-12 IL IL173134A patent/IL173134A0/en unknown
- 2006-01-13 CR CR8189A patent/CR8189A/es not_active Application Discontinuation
- 2006-01-31 NO NO20060494A patent/NO20060494L/no not_active Application Discontinuation
- 2006-02-06 ZA ZA200601055A patent/ZA200601055B/en unknown
- 2006-02-28 CO CO06019898A patent/CO5650251A2/es unknown
- 2006-03-07 EC EC2006006413A patent/ECSP066413A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO20060494L (no) | 2006-03-06 |
| RU2006106910A (ru) | 2007-09-20 |
| ES2287772T3 (es) | 2007-12-16 |
| JP2007501783A (ja) | 2007-02-01 |
| JP4227649B2 (ja) | 2009-02-18 |
| ECSP066413A (es) | 2006-09-18 |
| RU2339639C2 (ru) | 2008-11-27 |
| CR8189A (es) | 2006-10-04 |
| UA83245C2 (en) | 2008-06-25 |
| PT1658295E (pt) | 2007-09-25 |
| AU2004265267A1 (en) | 2005-02-24 |
| ZA200601055B (en) | 2008-07-30 |
| EP1658295A2 (en) | 2006-05-24 |
| CO5650251A2 (es) | 2006-06-30 |
| PL1658295T3 (pl) | 2007-11-30 |
| KR20060057605A (ko) | 2006-05-26 |
| WO2005016935A3 (en) | 2005-04-07 |
| CA2532988A1 (en) | 2005-02-24 |
| US7153957B2 (en) | 2006-12-26 |
| DK1658295T3 (da) | 2007-09-24 |
| EP1658295B1 (en) | 2007-06-20 |
| TW200508241A (en) | 2005-03-01 |
| MXPA06000951A (es) | 2006-03-30 |
| WO2005016935A2 (en) | 2005-02-24 |
| ATE365169T1 (de) | 2007-07-15 |
| US20050033046A1 (en) | 2005-02-10 |
| BRPI0412667A (pt) | 2006-09-26 |
| IL173134A0 (en) | 2006-06-11 |
| DE602004007145T2 (de) | 2008-02-28 |
| CN1829722A (zh) | 2006-09-06 |
| CN1829722B (zh) | 2010-10-27 |
| DE602004007145D1 (de) | 2007-08-02 |
| HK1085482A1 (en) | 2006-08-25 |
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