DE10326097A1 - Verfahren zur Herstellung von Dimethyl-(3-aryl-butyl)-aminverbindungen - Google Patents

Verfahren zur Herstellung von Dimethyl-(3-aryl-butyl)-aminverbindungen Download PDF

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Publication number
DE10326097A1
DE10326097A1 DE10326097A DE10326097A DE10326097A1 DE 10326097 A1 DE10326097 A1 DE 10326097A1 DE 10326097 A DE10326097 A DE 10326097A DE 10326097 A DE10326097 A DE 10326097A DE 10326097 A1 DE10326097 A1 DE 10326097A1
Authority
DE
Germany
Prior art keywords
methyl
phenyl
dimethylamine
dimethylamino
methoxy
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.)
Withdrawn
Application number
DE10326097A
Other languages
German (de)
English (en)
Inventor
Wolfgang Dr. Hell
Markus Dr. Kegel
Bernhard Dr. Akteries
Helmut Dr. Buschmann
Jörg Dr. Holenz
Hartmut Dr. Löbermann
Detlef Dr. Heller
Hans-Joachim Dr. Drexler
Stefan Dr. Gladow
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Grünenthal GmbH
Original Assignee
Grünenthal GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=33494923&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=DE10326097(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Grünenthal GmbH filed Critical Grünenthal GmbH
Priority to DE10326097A priority Critical patent/DE10326097A1/de
Priority to CA2528087A priority patent/CA2528087C/en
Priority to SI200431114T priority patent/SI1633697T1/sl
Priority to MXPA05013193A priority patent/MXPA05013193A/es
Priority to JP2006508271A priority patent/JP4848268B2/ja
Priority to DK04739583T priority patent/DK1633697T3/da
Priority to DE502004009142T priority patent/DE502004009142D1/de
Priority to CN2004800218627A priority patent/CN1829681B/zh
Priority to AT04739583T priority patent/ATE425136T1/de
Priority to PL04739583T priority patent/PL1633697T3/pl
Priority to ES04739583T priority patent/ES2323870T3/es
Priority to HR20090333T priority patent/HRP20090333T1/xx
Priority to PCT/EP2004/006027 priority patent/WO2004108658A1/de
Priority to AU2004245223A priority patent/AU2004245223C1/en
Priority to NZ544231A priority patent/NZ544231A/en
Priority to BRPI0411268A priority patent/BRPI0411268C8/pt
Priority to RU2005141518/04A priority patent/RU2380355C2/ru
Priority to EP04739583A priority patent/EP1633697B1/de
Priority to PT04739583T priority patent/PT1633697E/pt
Priority to HK06110185.8A priority patent/HK1088597B/xx
Priority to KR1020057023464A priority patent/KR101146205B1/ko
Publication of DE10326097A1 publication Critical patent/DE10326097A1/de
Priority to IL172357A priority patent/IL172357A/en
Priority to US11/294,449 priority patent/US7417170B2/en
Priority to EC2005006218A priority patent/ECSP056218A/es
Priority to NO20060044A priority patent/NO335587B1/no
Priority to ZA200600109A priority patent/ZA200600109B/en
Priority to CY20091100536T priority patent/CY1109088T1/el
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/64—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms
    • C07C217/66—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain
    • C07C217/72—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
    • C07C209/70—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by reduction of unsaturated amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
    • C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
    • C07C211/28—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by unsaturated carbon chains
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C215/56—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups
    • C07C215/58—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
    • C07C215/62—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain the chain having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
DE10326097A 2003-06-06 2003-06-06 Verfahren zur Herstellung von Dimethyl-(3-aryl-butyl)-aminverbindungen Withdrawn DE10326097A1 (de)

Priority Applications (27)

Application Number Priority Date Filing Date Title
DE10326097A DE10326097A1 (de) 2003-06-06 2003-06-06 Verfahren zur Herstellung von Dimethyl-(3-aryl-butyl)-aminverbindungen
KR1020057023464A KR101146205B1 (ko) 2003-06-06 2004-06-04 치환된 3-아릴-부틸-아민 화합물의 제조방법
PCT/EP2004/006027 WO2004108658A1 (de) 2003-06-06 2004-06-04 Verfahren zur herstellung substituierter 3-aryl-butyl-aminverbindungen
NZ544231A NZ544231A (en) 2003-06-06 2004-06-04 Process for the preparation of substituted 3-aryl-butyl-amine compounds
MXPA05013193A MXPA05013193A (es) 2003-06-06 2004-06-04 Metodo para la produccion de compuestos sustituidos de 3-aril-butil-amina.
JP2006508271A JP4848268B2 (ja) 2003-06-06 2004-06-04 置換された３−アリールブチル−アミン−化合物の製造方法
DK04739583T DK1633697T3 (da) 2003-06-06 2004-06-04 Fremgangsmåde til fremstilling af substituerede 3-aryl-butyl-aminforbindelser
DE502004009142T DE502004009142D1 (de) 2003-06-06 2004-06-04 Verfahren zur herstellung substituierter 3-aryl-butyl-aminverbindungen
CN2004800218627A CN1829681B (zh) 2003-06-06 2004-06-04 取代的3-芳基-丁基-胺化合物的制备方法
AT04739583T ATE425136T1 (de) 2003-06-06 2004-06-04 Verfahren zur herstellung substituierter 3-aryl- butyl-aminverbindungen
PL04739583T PL1633697T3 (pl) 2003-06-06 2004-06-04 Sposób wytwarzania podstawionych związków 3-arylo-butylo-aminowych
ES04739583T ES2323870T3 (es) 2003-06-06 2004-06-04 Procedimiento para la produccion de compuestos de 3-aril-butil-amina sustituidos.
HR20090333T HRP20090333T1 (hr) 2003-06-06 2004-06-04 Postupak za proizvodnju supstituiranih spojeva 3-aril-butil-amina
CA2528087A CA2528087C (en) 2003-06-06 2004-06-04 Process for the preparation of substituted 3-aryl-butyl-amine compounds
AU2004245223A AU2004245223C1 (en) 2003-06-06 2004-06-04 Method for the production of substituted 3-aryl-butyl amine compounds
SI200431114T SI1633697T1 (sl) 2003-06-06 2004-06-04 Postopek za pripravo substituiranih 3-aril-butilaminskih spojin
BRPI0411268A BRPI0411268C8 (pt) 2003-06-06 2004-06-04 Processo para a preparação de compostos 3-aril butil-amina substituído
RU2005141518/04A RU2380355C2 (ru) 2003-06-06 2004-06-04 Способ получения замещенных 3-арилбутиламиновых соединений
EP04739583A EP1633697B1 (de) 2003-06-06 2004-06-04 Verfahren zur herstellung substituierter 3-aryl-butyl-aminverbindungen
PT04739583T PT1633697E (pt) 2003-06-06 2004-06-04 Processo para a produção de compostos substituídos de 3-arilbutilamina
HK06110185.8A HK1088597B (en) 2003-06-06 2004-06-04 Method for the production of substituted 3-aryl-butyl amine compounds
IL172357A IL172357A (en) 2003-06-06 2005-12-05 METHOD FOR PRODUCING AMINO-BUTYL CONCENTRATED AMINO COMPOUNDS
US11/294,449 US7417170B2 (en) 2003-06-06 2005-12-06 Process for the preparation of substituted 3-aryl-butylamine compounds
EC2005006218A ECSP056218A (es) 2003-06-06 2005-12-13 Metodo para la produccion de compuestos de 3-aryl-butil-amina substituidos.
NO20060044A NO335587B1 (no) 2003-06-06 2006-01-04 Fremgangsmåte for fremstilling av substituerte 3-aryl-butyl-aminforbindelser
ZA200600109A ZA200600109B (en) 2003-06-06 2006-01-05 Method for the producting of substituted 3-aryl-butyl amine compounds
CY20091100536T CY1109088T1 (el) 2003-06-06 2009-05-21 Μεθοδος για την παρασκευη υποκατεστημενων ενωσεων 3-αρυλο-βουτυλ-αμινης

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE10326097A DE10326097A1 (de) 2003-06-06 2003-06-06 Verfahren zur Herstellung von Dimethyl-(3-aryl-butyl)-aminverbindungen

Publications (1)

Publication Number Publication Date
DE10326097A1 true DE10326097A1 (de) 2005-01-05

Family

ID=33494923

Family Applications (2)

Application Number Title Priority Date Filing Date
DE10326097A Withdrawn DE10326097A1 (de) 2003-06-06 2003-06-06 Verfahren zur Herstellung von Dimethyl-(3-aryl-butyl)-aminverbindungen
DE502004009142T Expired - Lifetime DE502004009142D1 (de) 2003-06-06 2004-06-04 Verfahren zur herstellung substituierter 3-aryl-butyl-aminverbindungen

Family Applications After (1)

Application Number Title Priority Date Filing Date
DE502004009142T Expired - Lifetime DE502004009142D1 (de) 2003-06-06 2004-06-04 Verfahren zur herstellung substituierter 3-aryl-butyl-aminverbindungen

Country Status (25)

Country Link
US (1) US7417170B2 (cg-RX-API-DMAC7.html)
EP (1) EP1633697B1 (cg-RX-API-DMAC7.html)
JP (1) JP4848268B2 (cg-RX-API-DMAC7.html)
KR (1) KR101146205B1 (cg-RX-API-DMAC7.html)
CN (1) CN1829681B (cg-RX-API-DMAC7.html)
AT (1) ATE425136T1 (cg-RX-API-DMAC7.html)
AU (1) AU2004245223C1 (cg-RX-API-DMAC7.html)
BR (1) BRPI0411268C8 (cg-RX-API-DMAC7.html)
CA (1) CA2528087C (cg-RX-API-DMAC7.html)
CY (1) CY1109088T1 (cg-RX-API-DMAC7.html)
DE (2) DE10326097A1 (cg-RX-API-DMAC7.html)
DK (1) DK1633697T3 (cg-RX-API-DMAC7.html)
EC (1) ECSP056218A (cg-RX-API-DMAC7.html)
ES (1) ES2323870T3 (cg-RX-API-DMAC7.html)
HR (1) HRP20090333T1 (cg-RX-API-DMAC7.html)
IL (1) IL172357A (cg-RX-API-DMAC7.html)
MX (1) MXPA05013193A (cg-RX-API-DMAC7.html)
NO (1) NO335587B1 (cg-RX-API-DMAC7.html)
NZ (1) NZ544231A (cg-RX-API-DMAC7.html)
PL (1) PL1633697T3 (cg-RX-API-DMAC7.html)
PT (1) PT1633697E (cg-RX-API-DMAC7.html)
RU (1) RU2380355C2 (cg-RX-API-DMAC7.html)
SI (1) SI1633697T1 (cg-RX-API-DMAC7.html)
WO (1) WO2004108658A1 (cg-RX-API-DMAC7.html)
ZA (1) ZA200600109B (cg-RX-API-DMAC7.html)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102005052588A1 (de) * 2005-11-02 2007-05-10 Grünenthal GmbH Verfahren zur Herstellung substituierter Dimethyl-(3-aryl-butyl)-amin-Verbindungen mittels homogener Katalyse

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DE10328316A1 (de) 2003-06-23 2005-01-20 Grünenthal GmbH Verfahren zur Herstellung von Dimethyl-(3-aryl-buthyl)-aminverbindungen als pharmazeutische Wirkstoffe
TWI401237B (zh) 2006-07-24 2013-07-11 ３-〔（１ｒ，２ｒ）-３-（二甲基氨基）-１-乙基-２-甲基丙基〕酚之製備
SI2046726T1 (sl) 2006-07-24 2010-05-31 Janssen Pharmaceutica Nv Priprava R R metoksifenil N N trimetilpentanamina
TWI496762B (zh) * 2006-07-24 2015-08-21 歌林達股份有限公司 製備（１ｒ，２ｒ）-３-（３-二甲胺基-１-乙基-２-甲基-丙基）-酚之方法
HRP20170481T1 (hr) * 2007-12-07 2017-05-19 Grünenthal GmbH Kristalne modifikacije (1r, 2r)-3-(3-dimentil amino-1-etil-2-metil-propil) fenola
WO2010100477A2 (en) * 2009-03-03 2010-09-10 Shire Llc Amino acid and peptide carbamate prodrugs of tapentadol and uses thereof
CN102002065B (zh) * 2009-09-02 2014-09-10 上海特化医药科技有限公司 他喷他多的制备方法及其中间体
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IT1397189B1 (it) * 2009-12-01 2013-01-04 Archimica Srl Nuovo processo per la preparazione di tapentadol e suoi intermedi.
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US20130096346A1 (en) 2010-03-05 2013-04-18 Actavis Group Ptc Ehf Resolution methods for isolating desired enantiomers of tapentadol intermediates and use thereof for the preparation of tapentadol
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ITMI20100924A1 (it) * 2010-05-21 2011-11-22 Fidia Farmaceutici Nuovo metodo di sintesi delle due forme enantiomeriche del tapentadol
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CN102477016B (zh) * 2010-11-26 2014-12-17 中国医学科学院药物研究所 他喷他多的中间体的合成与应用
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WO2012146978A2 (en) 2011-04-28 2012-11-01 Actavis Group Ptc Ehf A novel process for the preparation of tapentadol or a pharmaceutically acceptable salt thereof
EP2530072A1 (en) 2011-06-03 2012-12-05 Lacer, S.A. New compounds, synthesis and use thereof in the treatment of pain
US8853393B2 (en) 2011-07-29 2014-10-07 Anhui New Star Pharmaceutical Development Co., Ltd. Intermediate for preparing tapentadol or analogues thereof
WO2013105109A1 (en) 2011-11-09 2013-07-18 Indoco Remedies Limited Process for the preparation of tapentadol
WO2013090161A1 (en) 2011-12-12 2013-06-20 Boehringer Ingelheim International Gmbh Stereoselective synthesis of tapentadol and its salts
WO2013120466A1 (en) 2012-02-17 2013-08-22 Zentiva, K.S. A new solid form of tapentadol and a method of its preparation
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CN103159633B (zh) * 2012-07-06 2015-08-12 江苏恩华药业股份有限公司 他喷他多的制备方法及用于制备他喷他多的化合物
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SI3083551T1 (en) 2013-12-16 2018-04-30 Farma Grs, D.O.O. CRYSTAL FORM INTERMEDIATE TAPENTADOL
CZ307492B6 (cs) 2014-02-04 2018-10-17 Zentiva, K.S. Pevná forma maleátu tapentadolu a způsob její přípravy
PT3319941T (pt) 2015-07-10 2022-03-18 SpecGx LLC Processo em dois passos para preparação de fenilalquilaminas 3-substituídas
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Publication number Priority date Publication date Assignee Title
DE102005052588A1 (de) * 2005-11-02 2007-05-10 Grünenthal GmbH Verfahren zur Herstellung substituierter Dimethyl-(3-aryl-butyl)-amin-Verbindungen mittels homogener Katalyse
US8791300B2 (en) 2005-11-02 2014-07-29 Gruenenthal Gmbh Process for preparing a substituted dimethyl-(3-arylbutyl)amine compound by homogeneous catalysis

Also Published As

Publication number Publication date
PT1633697E (pt) 2009-06-04
BRPI0411268A (pt) 2006-08-01
AU2004245223A1 (en) 2004-12-16
EP1633697A1 (de) 2006-03-15
CY1109088T1 (el) 2014-07-02
AU2004245223B2 (en) 2010-01-28
BRPI0411268B1 (pt) 2020-11-03
AU2004245223C1 (en) 2010-06-10
WO2004108658A1 (de) 2004-12-16
NO20060044L (no) 2006-01-04
NZ544231A (en) 2009-06-26
KR20060036923A (ko) 2006-05-02
US20060194988A1 (en) 2006-08-31
EP1633697B1 (de) 2009-03-11
KR101146205B1 (ko) 2012-05-25
CA2528087C (en) 2012-05-01
SI1633697T1 (sl) 2009-08-31
NO335587B1 (no) 2015-01-05
DK1633697T3 (da) 2009-06-02
HK1088597A1 (zh) 2006-11-10
RU2380355C2 (ru) 2010-01-27
JP4848268B2 (ja) 2011-12-28
JP2006527178A (ja) 2006-11-30
CN1829681A (zh) 2006-09-06
ES2323870T3 (es) 2009-07-27
ZA200600109B (en) 2007-01-31
ECSP056218A (es) 2006-04-19
BRPI0411268B8 (pt) 2021-01-19
BRPI0411268C8 (pt) 2021-11-16
PL1633697T3 (pl) 2009-08-31
DE502004009142D1 (de) 2009-04-23
RU2005141518A (ru) 2007-07-20
BRPI0411268C1 (pt) 2021-05-25
IL172357A0 (en) 2009-02-11
US7417170B2 (en) 2008-08-26
MXPA05013193A (es) 2006-03-09
IL172357A (en) 2014-09-30
ATE425136T1 (de) 2009-03-15
HRP20090333T1 (hr) 2009-07-31
CN1829681B (zh) 2013-02-06
CA2528087A1 (en) 2004-12-16

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