CO5650251A2 - Sintesis regioselectiva de cci-779 - Google Patents
Sintesis regioselectiva de cci-779Info
- Publication number
- CO5650251A2 CO5650251A2 CO06019898A CO06019898A CO5650251A2 CO 5650251 A2 CO5650251 A2 CO 5650251A2 CO 06019898 A CO06019898 A CO 06019898A CO 06019898 A CO06019898 A CO 06019898A CO 5650251 A2 CO5650251 A2 CO 5650251A2
- Authority
- CO
- Colombia
- Prior art keywords
- carbon atoms
- rapamycin
- ester
- phenyl
- dioxaborinan
- Prior art date
Links
- CBPNZQVSJQDFBE-FUXHJELOSA-N Temsirolimus Chemical compound C1C[C@@H](OC(=O)C(C)(CO)CO)[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 CBPNZQVSJQDFBE-FUXHJELOSA-N 0.000 title abstract 2
- 229960000235 temsirolimus Drugs 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 10
- 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 abstract 9
- 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 9
- 229960002930 sirolimus Drugs 0.000 abstract 9
- 125000003342 alkenyl group Chemical group 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000000304 alkynyl group Chemical group 0.000 abstract 3
- 229910052796 boron Inorganic materials 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- -1 2-phenyl-1,3,2-dioxaborinan-5-yl Chemical group 0.000 abstract 2
- QOBHKTQNPVOMIX-UHFFFAOYSA-N 5-methyl-2-phenyl-1,3,2-dioxaborinane-5-carboxylic acid Chemical compound O1CC(C)(C(O)=O)COB1C1=CC=CC=C1 QOBHKTQNPVOMIX-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000004849 alkoxymethyl group Chemical group 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
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000002009 diols Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000000034 method 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)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Catalysts (AREA)
Abstract
1.- Un procedimiento para preparar un 42-éster de rapamicina, caracterizado porque comprende:(a) acilar un éter 31-silílico de rapamicina con un compuesto de la fórmula HOOC.CR7R8R9 o un anhídrido mixto del mismo, en donde:R7 es hidrógeno, alquilo de 1-6 átomos de carbono, alquenilo de 2-7 átomos de carbono, alquinilo de 2-7 átomos de carbono, -(CR12R13)fOR10 -CF3, -F o -CO2R10;R10 es hidrógeno, alquilo de 1-6 átomos de carbono, alquenilo de 2-7 átomos de carbono, alquinilo de 2-7 átomos de carbono, trifenilmetilo, bencilo, alcoximetilo de 2-7 átomos de carbono, cloroetilo o tetrahidropiranilo;R8 y R9 se toman juntos para formar X;X es un 2-fenil-1,3,2-dioxaborinan-5-ilo o 2-fenil- 1,3,2-dioxaborinan-4-ilo, en donde el fenilo puede ser sustituido opcionalmente;R12R13 son cada uno, independientemente, hidrógeno, alquilo de 1-6 átomos de carbono, alquenilo de 2-7 átomos carbono, alquinilo de 2-7 átomos de carbono, trifluorometilo o -F;yf = 0-6;para dar un 42-éster boronato éter 31-silílico de rapamicina.(b) hidrolizar selectivamente 42-éster boronato éter 31-silílico en condiciones levemente ácidas para formar un 42-éster boronato de rapamicina.y(c) tratar el 42-éster boronato de rapamicina un diol adecuado para proporcionar un 42-éster de rapamicina.2.- El procedimiento de conformidad con la reivindicación 1, caracterizado porque el 42-éster de rapamicina preparado es CCI-779, y en donde la etapa de acilación (a) comprende acilar el éter 31-silílico de rapamicina con ácido 5-metil-2-fenil-1,3,2-dioxaborinan-5-carboxílico o un anhídrido mixto de ácido 5-metil-2-fenil-1,3,2-dioxaborinan-5-carboxílico para dar éter 31-0-silílico de rapamicina, 42-éster boronato.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49324903P | 2003-08-07 | 2003-08-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CO5650251A2 true CO5650251A2 (es) | 2006-06-30 |
Family
ID=34193170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CO06019898A CO5650251A2 (es) | 2003-08-07 | 2006-02-28 | Sintesis regioselectiva de cci-779 |
Country Status (27)
| 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) |
| HK (1) | HK1085482A1 (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) |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE427948T1 (de) | 2001-04-24 | 2009-04-15 | Purdue Research Foundation | Folat-mimetika und deren folatrezeptorbindende konjugate |
| AU2003243226A1 (en) * | 2002-05-15 | 2003-12-02 | Endocyte, Inc. | Vitamin-mitomycin conjugates |
| KR101131794B1 (ko) * | 2002-07-30 | 2012-03-30 | 와이어쓰 엘엘씨 | Ｃｃｉ-779 공용매 농축액, 비경구 ｃｃｉ-779 제형 및 비경구 ｃｃｉ-779 제형의 제조방법 |
| DK1592457T3 (da) | 2003-01-27 | 2012-10-22 | Endocyte Inc | Folat-vinblastin-konjugat som lægemiddel |
| JP2007504226A (ja) * | 2003-09-03 | 2007-03-01 | ワイス | 非晶質状のラパマイシンの３−ヒドロキシ−２−（ヒドロキシメチル）−２−メチルプロピオン酸との４２−エステル、およびそれを含むその医薬組成物 |
| CN1921861A (zh) * | 2004-01-08 | 2007-02-28 | 惠氏公司 | 用于cci－779的口服给药的可直接压片的药物组合物 |
| RU2387657C2 (ru) | 2004-04-14 | 2010-04-27 | Вайет | Региоспецифический синтез производных 42-эфира рапамицина |
| WO2005100366A1 (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 |
| BRPI0509810A (pt) * | 2004-04-14 | 2007-09-18 | Wyeth Corp | método para a sìntese regioespecìfica de um 42-hemiéster de rapamicina ou um 32-hemiéster de fk-506 com um ácido dicarboxìlico, 42-hemiéster de rapamicina regioespecìfica, anticorpo de rapamicina, produto, e, 32-hemiéster de fk506 regioespecìfico |
| BRPI0510277A (pt) * | 2004-04-27 | 2007-10-30 | Wyeth Corp | método para marcar especificamente uma rapamicina, rapamicina especificamente marcada, composição, e, kit |
| WO2006012527A1 (en) | 2004-07-23 | 2006-02-02 | Endocyte, Inc. | Bivalent linkers and conjugates thereof |
| EP1776370A1 (en) * | 2004-08-10 | 2007-04-25 | Wyeth a Corporation of the State of Delaware | Cci-779 derivatives and methods of making same |
| CN101048152A (zh) | 2004-10-28 | 2007-10-03 | 惠氏公司 | mTOR抑制剂在治疗子宫平滑肌瘤中的应用 |
| BRPI0607932A2 (pt) | 2005-02-09 | 2016-11-08 | Wyeth Corp | polimorfo cci-779, processo para preparar polimorfo cci-779, composição farmacêutica, kit, e método para preparar uma composição farmacêutica |
| US7384953B2 (en) | 2005-03-02 | 2008-06-10 | Wyeth | Purification of rapamycin |
| CN101133066A (zh) * | 2005-03-02 | 2008-02-27 | 惠氏公司 | 从母液中回收cci-779 |
| EP1863816B1 (en) | 2005-03-16 | 2014-06-25 | Endocyte, Inc. | Synthesis and purification of pteroic acid and conjugates thereof |
| EP2382995A3 (en) * | 2005-08-19 | 2013-09-25 | Endocyte, Inc. | Ligand conjugates of Vinca alkaloids, analogs and derivatives |
| CN103893778A (zh) | 2005-08-19 | 2014-07-02 | 恩多塞特公司 | 多药物配体缀合物 |
| WO2007056175A2 (en) * | 2005-11-04 | 2007-05-18 | Wyeth | 41-methoxy isotope labeled rapamycin 42-ester |
| AR057854A1 (es) | 2005-11-04 | 2007-12-19 | Wyeth Corp | Combinaciones antineoplasicas con inhibidor de mtor, herceptina y/o hki-272 (e)-n-{4-[3-cloro-4-(2-piridinilmetoxi) anilino]-3-ciano-7-etoxi-6-quinolinil}-4-(dimetilamino)-2-butenamida |
| KR20080077618A (ko) * | 2005-12-07 | 2008-08-25 | 와이어쓰 | 정제된 결정체 ｃｃｉ-779 의 제조 방법 |
| KR20080077147A (ko) * | 2005-12-07 | 2008-08-21 | 와이어쓰 | 결정성 라파마이신의 제조 방법 및 시차 주사 열량계를사용하는 라파마이신 화합물의 결정화도의 측정 방법 |
| WO2007067560A2 (en) * | 2005-12-07 | 2007-06-14 | Wyeth | Scalable process for the preparation of a rapamycin 42-ester from a rapamycin 42-ester boronate |
| CN101340901A (zh) * | 2005-12-20 | 2009-01-07 | 惠氏公司 | 通过控制药物物质杂质控制cci-779剂型稳定性 |
| 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 |
| US9700704B2 (en) | 2006-11-20 | 2017-07-11 | Lutonix, Inc. | Drug releasing coatings for balloon catheters |
| US8414525B2 (en) | 2006-11-20 | 2013-04-09 | Lutonix, Inc. | Drug releasing coatings for medical devices |
| 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 |
| US8998846B2 (en) | 2006-11-20 | 2015-04-07 | 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 |
| US8414910B2 (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 |
| US9737640B2 (en) | 2006-11-20 | 2017-08-22 | Lutonix, Inc. | Drug releasing coatings for medical devices |
| 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 |
| US8430055B2 (en) | 2008-08-29 | 2013-04-30 | Lutonix, Inc. | Methods and apparatuses for coating balloon catheters |
| WO2008101231A2 (en) * | 2007-02-16 | 2008-08-21 | Endocyte, Inc. | Methods and compositions for treating and diagnosing kidney disease |
| NZ599239A (en) * | 2007-03-14 | 2013-10-25 | Endocyte Inc | Binding ligand linked drug delivery conjugates of tubulysins |
| 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 |
| AU2008268432B2 (en) * | 2007-06-25 | 2015-01-15 | Endocyte, Inc. | Conjugates containing hydrophilic spacer linkers |
| US9877965B2 (en) | 2007-06-25 | 2018-01-30 | Endocyte, Inc. | Vitamin receptor drug delivery conjugates for treating inflammation |
| JP2011500835A (ja) | 2007-10-25 | 2011-01-06 | エンドサイト，インコーポレイテッド | チューブリシン類および調製プロセス |
| EP2480557A2 (en) | 2009-09-25 | 2012-08-01 | Cadila Healthcare Limited | Process for the preparation of rapamycin derivatives |
| JP2013518093A (ja) * | 2010-01-28 | 2013-05-20 | フレゼニウス・カビ・オンコロジー・リミテッド | テムシロリムスの製造のための改善された方法およびその中間体 |
| 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 |
| KR20140013000A (ko) * | 2011-04-01 | 2014-02-04 | 산도즈 아게 | C-42 위치에서 라파마이신의 위치선택적 아실화 |
| 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 |
| CA2887727A1 (en) | 2012-10-16 | 2014-04-24 | Endocyte, Inc. | Drug delivery conjugates containing unnatural amino acids and methods for using |
| 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 AT AT04778398T patent/ATE365169T1/de not_active IP Right Cessation
- 2004-07-15 ES ES04778398T patent/ES2287772T3/es active Active
- 2004-07-15 UA UAA200602447A patent/UA83245C2/ru unknown
- 2004-07-15 AU AU2004265267A patent/AU2004265267A1/en not_active Abandoned
- 2004-07-15 CA CA002532988A patent/CA2532988A1/en not_active Abandoned
- 2004-07-15 PL PL04778398T patent/PL1658295T3/pl unknown
- 2004-07-15 WO PCT/US2004/022860 patent/WO2005016935A2/en active IP Right Grant
- 2004-07-15 CN CN2004800217944A patent/CN1829722B/zh not_active Expired - Fee Related
- 2004-07-15 EP EP04778398A patent/EP1658295B1/en active Active
- 2004-07-15 MX MXPA06000951A patent/MXPA06000951A/es active IP Right Grant
- 2004-07-15 PT PT04778398T patent/PT1658295E/pt unknown
- 2004-07-15 DK DK04778398T patent/DK1658295T3/da active
- 2004-07-15 DE DE602004007145T patent/DE602004007145T2/de not_active Expired - Fee Related
- 2004-07-15 RU RU2006106910/04A patent/RU2339639C2/ru not_active IP Right Cessation
- 2004-07-15 JP JP2006522574A patent/JP4227649B2/ja not_active Expired - Fee Related
- 2004-07-15 BR BRPI0412667-0A patent/BRPI0412667A/pt not_active IP Right Cessation
- 2004-07-15 KR KR1020067002610A patent/KR20060057605A/ko not_active Application Discontinuation
- 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
- 2006-07-11 HK HK06107729A patent/HK1085482A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE602004007145T2 (de) | 2008-02-28 |
| BRPI0412667A (pt) | 2006-09-26 |
| UA83245C2 (en) | 2008-06-25 |
| US7153957B2 (en) | 2006-12-26 |
| CN1829722A (zh) | 2006-09-06 |
| WO2005016935A3 (en) | 2005-04-07 |
| RU2339639C2 (ru) | 2008-11-27 |
| AU2004265267A1 (en) | 2005-02-24 |
| CR8189A (es) | 2006-10-04 |
| DK1658295T3 (da) | 2007-09-24 |
| IL173134A0 (en) | 2006-06-11 |
| ZA200601055B (en) | 2008-07-30 |
| US20050033046A1 (en) | 2005-02-10 |
| MXPA06000951A (es) | 2006-03-30 |
| AR045217A1 (es) | 2005-10-19 |
| PT1658295E (pt) | 2007-09-25 |
| WO2005016935A2 (en) | 2005-02-24 |
| ECSP066413A (es) | 2006-09-18 |
| RU2006106910A (ru) | 2007-09-20 |
| ATE365169T1 (de) | 2007-07-15 |
| JP4227649B2 (ja) | 2009-02-18 |
| NO20060494L (no) | 2006-03-06 |
| EP1658295B1 (en) | 2007-06-20 |
| EP1658295A2 (en) | 2006-05-24 |
| TW200508241A (en) | 2005-03-01 |
| CN1829722B (zh) | 2010-10-27 |
| DE602004007145D1 (de) | 2007-08-02 |
| CA2532988A1 (en) | 2005-02-24 |
| HK1085482A1 (en) | 2006-08-25 |
| ES2287772T3 (es) | 2007-12-16 |
| KR20060057605A (ko) | 2006-05-26 |
| JP2007501783A (ja) | 2007-02-01 |
| PL1658295T3 (pl) | 2007-11-30 |
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