ES2377337T3 - Derivados pirimidina y su uso como antogonistas del receptor P2Y12 - Google Patents

Derivados pirimidina y su uso como antogonistas del receptor P2Y12 Download PDF

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ES2377337T3
ES2377337T3 ES06728064T ES06728064T ES2377337T3 ES 2377337 T3 ES2377337 T3 ES 2377337T3 ES 06728064 T ES06728064 T ES 06728064T ES 06728064 T ES06728064 T ES 06728064T ES 2377337 T3 ES2377337 T3 ES 2377337T3
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alkyl
hydrogen
aryl
heterocyclic ring
cycloalkyl
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Eva Caroff
Heinz Fretz
Kurt Hilpert
Olivier Houille
Francis Hubler
Emmanuel Meyer
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Actelion Pharmaceuticals Ltd
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Actelion Pharmaceuticals Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/08—Vasodilators for multiple indications
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/38—One sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (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)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)

Abstract

Un compuesto seleccionado del grupo que consiste en los compuestos de fórmula I en la cual R1 representa fenilo opcionalmente sustituido de 1 a 3 veces por sustituyentes cada uno independientemente seleccionado del grupo que consiste en halógeno, metilo, metoxi, trifluorometilo y trifluorometoxi; W representa un enlace, y R2 representa alquilo, haloalquilo, ciano, hidroxialquilo, hidroxialquilo sustituido en su cadena alquílica con un grupo fenilo no sustituido, alcoxialquilo, heterociclilo, heterociclilalquilo, cicloalquilo, cicloalquilalquilo, arilo, heteroarilo, o uno de los radicales en los cuales m es 0 y n es 2 ó 3, o m es 1 y n es 2, p es 0 y q es 2 ó 3, o p es 1 y q es 2, o también p es 2 ó 3 y q es 0, Q es -CO- o -CH(ORa)-, siendo Ra hidrógeno o alquilo, y Q' es -CO-; o W representa -CH2- y R2 representa -NR7R8, -SR9 o -SO2R10; W representa -O- o -S- y R2 representa alquilo, carboxialquilo, alcoxicarbonilalquilo, hidroxialquilo, alcoxialquilo, heterociclilalquilo, cicloalquilo, cicloalquilalquilo, arilo, aralquilo, heteroarilo o heteroarilalquilo; W representa -NR3- y R2 representa hidrógeno, alquilo, dialquilaminoalquilo, alcoxicarbonilalquilo, carboxialquilo, carboxialquilo sustituido en su sección alquilo con un grupo fenilo no sustituido, hidroxialquilo, alcoxialquilo, heterociclilo, heterociclilalquilo, cicloalquilo, cicloalquilalquilo, arilo, 2-fenilciclopropilo, aralquilo, difenilalquilo, heteroarilalquilo en donde el heteroarilo es un heteroarilo monocíclico, -COR11 ó -SO2R12; W representa -CH=CH- y R2 representa alquilo, hidroxialquilo, alcoxialquilo, alcoxicarbonilo, fenilo o -CO-NR13R14; o W representa -CºC- y R2 representa hidrógeno, alquilo, hidroxialquilo o alcoxialquilo; o W representa -CO- y R2 representa alquilo; R3 representa hidrógeno o alquilo; R7 representa alquilo o arilalquilo; R8 representa alquilo; o R7 y R8 forman, en conjunto con el nitrógeno que los porta, un anillo heterocíclico de 4 a 7 elementos en el cual los elementos que se necesitan para completar dicho anillo heterocíclico se seleccionan de manera 5 independiente de entre -CH2-, -CH(CH3)-, -CHRy-, -O-, -S-, -CO- y -NRz-, entendiéndose sin embargo que dicho anillo heterocíclico no contiene más que un elemento seleccionado del grupo que consiste en -CHRy-, -O-, -S-, -CO- y -NRz-, representando Ry hidroxi, hidroximetilo, alcoximetilo, alcoxicarbonilo o alcoxi y representando Rz hidrógeno, alquilo o alcoxicarbonilo; R9 representa cicloalquilo o arilo; R10 representa alquilo, cicloalquilo o arilo; R11 representa alquilo, alcoxialquilo, cicloalquilo, cicloalquilalquilo, arilo, heteroarilo monocíclico o aralquilo; R12 representa alquilo o arilo; R13 representa alquilo; R14 representa alquilo; o W representa -NR3- y R2 y R3 forman, en conjunto con el nitrógeno que los porta, un anillo heterocíclico de 4 a 7 elementos en el cual los elementos que se necesitan para completar dicho anillo heterocíclico se seleccionan de manera independiente de entre -CH2-, -CHRx-, -O-, -S-, -CO- y -NR4-, y entendiéndose que dicho anillo heterocíclico no contiene más que un elemento seleccionado del grupo que consiste en -CHRx-, -O-, -S-, -CO- y -NR4-, representando Rx hidroxi, hidroximetilo, alcoximetilo o alcoxi y R4 20 representando hidrógeno o alquilo; o también W representa -NR3- y R2 y R3 forman, en conjunto con el nitrógeno que los porta, bien un anillo imidazolilo, pirazolilo, 1,2,3-triazolilo o 1,2,4-triazolilo, anillo que puede estar sustituido con un grupo alquilo, o un anillo 4-oxo-4H-piridin-1-ilo, 4,5-dihidro-pirazol-1-ilo, 2-metil-4,5-dihidro-imidazol-1-ilo o 3-metil-5-oxo-2,5- dihidro-pirazol-1-ilo; cada uno de R5a y R5b representa, de manera independiente, hidrógeno o metilo; X representa -CO- y R6 representa alquilo, cicloalquilo, alcoxi, alquiniloxi, ariloxi, aralcoxi, arilo, heteroarilo monocíclico, aralquilo o NR15R16, o X representa -SO2- y R6 representa alquilo; R15 representa alquilo; R16 representa hidrógeno o alquilo; o R15 y R16 forman, en conjunto con el nitrógeno que los porta, un anillo heterocíclico de 4 a 7 elementos, en el cual los elementos que se necesitan para completar dicho anillo heterocíclico se seleccionan de manera independiente de entre -CH2-, -O-, -S- y -NRw-, representando Rw hidrógeno o alquilo, entendiéndose que dicho anillo heterocíclico no contiene más que un elemento del grupo que consiste en -O-, -S- y -NRw-; e Y representa un enlace y Z representa hidrógeno o arilo sustituido por carboxialcoxi; o Y representa alquileno, alcoxialquileno, fenilalquileno, alcoxifenileno o alcoxifenilalquileno y Z representa hidrógeno, -OH, -NH2, -COOH, tetrazolilo, -CO-NH2, -COOR17, -NH-CO-R17, -NH-COOR17 o -NH-SO2-R17, representando R17 alquilo; y un enantiómero ópticamente puro, una mezcla de enantiómeros, un racemato, un diastereoisómero ópticamente puro, una mezcla de diastereoisómeros, un racemato diastereoisomérico, una mezcla de racematos diastereoisoméricos, una meso forma, una sal, un complejo disuelto, o una forma morfológica del mismo.
ES06728064T 2005-04-28 2006-04-27 Derivados pirimidina y su uso como antogonistas del receptor P2Y12 Active ES2377337T3 (es)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
EP2005004578 2005-04-28
WOPCT/EP2005/004578 2005-04-28
IB2005053711 2005-11-10
WOPCT/IB2005/053711 2005-11-10
PCT/IB2006/051318 WO2006114774A2 (en) 2005-04-28 2006-04-27 Pyrimidine derivatives and their use as p2y12 receptor antagonists

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ES2377337T3 true ES2377337T3 (es) 2012-03-26

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US (1) US8048881B2 (es)
EP (1) EP1893634B1 (es)
JP (1) JP4955658B2 (es)
KR (1) KR101310016B1 (es)
CN (1) CN101166756A (es)
AR (1) AR056992A1 (es)
AT (1) ATE538130T1 (es)
AU (1) AU2006241260A1 (es)
BR (1) BRPI0608089A2 (es)
CA (1) CA2604967C (es)
ES (1) ES2377337T3 (es)
IL (1) IL186939A0 (es)
MX (1) MX2007013436A (es)
NO (1) NO20076094L (es)
NZ (1) NZ563584A (es)
RU (1) RU2410393C2 (es)
TW (1) TW200640877A (es)
WO (1) WO2006114774A2 (es)

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US20100210635A1 (en) * 2006-03-29 2010-08-19 Takeda Pharmaceutical Company Limited Renin inhibitors
CL2007002920A1 (es) 2006-10-13 2008-06-06 Actelion Pharmaceuticals Ltd Compuestos derivados de 2-aminocarbonilpiridina; composicion farmaceutica; y uso para el tratamiento de trastornos vasculares oclusivos.
CL2007003038A1 (es) * 2006-10-25 2008-06-06 Actelion Pharmaceuticals Ltd Compuestos derivados de 2-fenil-6-aminocarbonil-pirimidina; composicion farmaceutica; y uso en el tratamiento de trastornos vasculares oclusivos.
EP2148871A1 (en) * 2007-04-23 2010-02-03 Sanofi-Aventis Quinoline-carboxamide derivatives as p2y12 antagonists
BRPI0819696B1 (pt) * 2007-11-29 2018-10-23 Actelion Pharmaceuticals Ltd compostos de derivados de 2-fenil-pirimidina, composição farmacêutica e uso de um composto
EP2238127B1 (en) * 2007-12-26 2012-08-15 Sanofi Pyrazole-carboxamide derivatives as p2y12 antagonists
JP5504171B2 (ja) * 2007-12-26 2014-05-28 サノフイ Ｐ２ｙ１２アンタゴニストとしてのヘテロサイクリックピラゾール−カルボキサミド
MX2010009561A (es) 2008-02-29 2010-09-24 Renovis Inc Compuestos amida, composiciones y usos de los mismos.
AR071652A1 (es) 2008-04-11 2010-07-07 Actelion Pharmaceuticals Ltd Derivados 2- fenil-piridina substituidos
AR071653A1 (es) * 2008-04-11 2010-07-07 Actelion Pharmaceuticals Ltd Derivados 2-fenil-4-ciclopropil-pirimidina
WO2009131127A1 (ja) * 2008-04-22 2009-10-29 第一三共株式会社 ５－ヒドロキシピリミジン－４－カルボキサミド化合物
US20110237578A1 (en) * 2008-09-18 2011-09-29 Zhi-Liang Wei Amide compounds, compositions and uses thereof
KR101114503B1 (ko) * 2008-12-04 2012-02-15 지에스건설 주식회사 부유물 수거장치
MA33260B1 (fr) * 2009-04-08 2012-05-02 Actelion Pharmaceuticals Ltd 6-(3-azabicyclo[3.1.0.]hex-3-yl)-2-phenylpyrimidines
KR101728180B1 (ko) * 2009-04-22 2017-04-18 액테리온 파마슈티칼 리미티드 티아졸 유도체들 및 ｐ2ｙ12 수용체 길항제로서 이들의 용도
JP5597202B2 (ja) 2009-08-28 2014-10-01 第一三共株式会社 ３−（ビアリールオキシ）プロピオン酸誘導体
US9539246B2 (en) 2011-08-30 2017-01-10 University Of Utah Research Foundation Methods and compositions for treating nephrogenic diabetes insipidus
ES2643235T3 (es) * 2011-09-02 2017-11-21 Purdue Pharma Lp Pirimidinas como bloqueantes del canal de sodio
RS62946B1 (sr) 2016-09-22 2022-03-31 Idorsia Pharmaceuticals Ltd Kristalni oblici
AU2018234056B2 (en) 2017-03-15 2023-05-25 Idorsia Pharmaceuticals Ltd Subcutaneous administration of a P2Y12 receptor antagonist
CN112500354A (zh) * 2020-12-08 2021-03-16 烟台凯博医药科技有限公司 一种4-氯-6-环丙基嘧啶-5-胺的合成方法

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JPS5373586A (en) * 1976-12-09 1978-06-30 Mitsubishi Chem Ind Ltd New penicillin derivatives
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DE60333866D1 (de) * 2002-12-11 2010-09-30 Bayer Schering Pharma Ag 2-aminocarbonlyl-chinolin-verbindungen als adenosin diphosphat plättchenrezeptor antagonisten
CL2007002920A1 (es) 2006-10-13 2008-06-06 Actelion Pharmaceuticals Ltd Compuestos derivados de 2-aminocarbonilpiridina; composicion farmaceutica; y uso para el tratamiento de trastornos vasculares oclusivos.
CL2007003038A1 (es) 2006-10-25 2008-06-06 Actelion Pharmaceuticals Ltd Compuestos derivados de 2-fenil-6-aminocarbonil-pirimidina; composicion farmaceutica; y uso en el tratamiento de trastornos vasculares oclusivos.
BRPI0819696B1 (pt) 2007-11-29 2018-10-23 Actelion Pharmaceuticals Ltd compostos de derivados de 2-fenil-pirimidina, composição farmacêutica e uso de um composto
AR071652A1 (es) 2008-04-11 2010-07-07 Actelion Pharmaceuticals Ltd Derivados 2- fenil-piridina substituidos
AR071653A1 (es) 2008-04-11 2010-07-07 Actelion Pharmaceuticals Ltd Derivados 2-fenil-4-ciclopropil-pirimidina
MA33260B1 (fr) 2009-04-08 2012-05-02 Actelion Pharmaceuticals Ltd 6-(3-azabicyclo[3.1.0.]hex-3-yl)-2-phenylpyrimidines
KR101728180B1 (ko) 2009-04-22 2017-04-18 액테리온 파마슈티칼 리미티드 티아졸 유도체들 및 ｐ2ｙ12 수용체 길항제로서 이들의 용도

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TW200640877A (en) 2006-12-01
RU2007143880A (ru) 2009-06-10
BRPI0608089A2 (pt) 2009-11-10
MX2007013436A (es) 2008-01-16
KR101310016B1 (ko) 2013-09-30
NZ563584A (en) 2011-03-31
JP2008539224A (ja) 2008-11-13
AR056992A1 (es) 2007-11-07
US20080194576A1 (en) 2008-08-14
JP4955658B2 (ja) 2012-06-20
ATE538130T1 (de) 2012-01-15
RU2410393C2 (ru) 2011-01-27
CN101166756A (zh) 2008-04-23
AU2006241260A1 (en) 2006-11-02
WO2006114774A2 (en) 2006-11-02
EP1893634A2 (en) 2008-03-05
CA2604967A1 (en) 2006-11-02
IL186939A0 (en) 2008-02-09
EP1893634B1 (en) 2011-12-21
WO2006114774A3 (en) 2007-02-08
KR20080004608A (ko) 2008-01-09
CA2604967C (en) 2014-04-01
US8048881B2 (en) 2011-11-01
NO20076094L (no) 2008-01-25

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