CN100484935C - 作为因子Xa抑制剂的苯并咪唑衍生物 - Google Patents

作为因子Xa抑制剂的苯并咪唑衍生物 Download PDF

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Publication number
CN100484935C
CN100484935C CNB2004800139377A CN200480013937A CN100484935C CN 100484935 C CN100484935 C CN 100484935C CN B2004800139377 A CNB2004800139377 A CN B2004800139377A CN 200480013937 A CN200480013937 A CN 200480013937A CN 100484935 C CN100484935 C CN 100484935C
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CN
China
Prior art keywords
chloro
benzimidazole
ylcarbamoyl
piperidin
carboxylic acid
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.)
Expired - Fee Related
Application number
CNB2004800139377A
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English (en)
Chinese (zh)
Other versions
CN1791598A (zh
Inventor
M·纳扎雷
M·瓦格纳
V·魏纳
H·马特
M·乌尔曼
K·里特
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Sanofi Aventis Deutschland GmbH
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Sanofi Aventis Deutschland GmbH
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Application filed by Sanofi Aventis Deutschland GmbH filed Critical Sanofi Aventis Deutschland GmbH
Publication of CN1791598A publication Critical patent/CN1791598A/zh
Application granted granted Critical
Publication of CN100484935C publication Critical patent/CN100484935C/zh
Anticipated expiration legal-status Critical
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D235/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00Drugs for disorders of the blood or the extracellular fluid
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00Drugs for disorders of the blood or the extracellular fluid
    • A61P7/04Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/04Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/08Vasodilators for multiple indications
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/02Heterocyclic 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
    • C07D401/12Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/14Heterocyclic 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 three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D473/00Heterocyclic compounds containing purine ring systems
    • C07D473/02Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
    • C07D473/04Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
    • C07D473/06Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
    • C07D473/08Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D495/00Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04Ortho-condensed systems

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Cardiology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Rheumatology (AREA)
  • Virology (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Pain & Pain Management (AREA)
  • Hospice & Palliative Care (AREA)
  • Obesity (AREA)
  • Pulmonology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
CNB2004800139377A 2003-05-19 2004-05-05 作为因子Xa抑制剂的苯并咪唑衍生物 Expired - Fee Related CN100484935C (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP03011305A EP1479676A1 (en) 2003-05-19 2003-05-19 Benzimidazole-derivatives as factor xa inhibitors
EP03011305.4 2003-05-19

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CNA2007101491602A Division CN101139346A (zh) 2003-05-19 2004-05-05 作为因子Xa抑制剂的苯并咪唑衍生物

Publications (2)

Publication Number Publication Date
CN1791598A CN1791598A (zh) 2006-06-21
CN100484935C true CN100484935C (zh) 2009-05-06

Family

ID=33040952

Family Applications (2)

Application Number Title Priority Date Filing Date
CNB2004800139377A Expired - Fee Related CN100484935C (zh) 2003-05-19 2004-05-05 作为因子Xa抑制剂的苯并咪唑衍生物
CNA2007101491602A Pending CN101139346A (zh) 2003-05-19 2004-05-05 作为因子Xa抑制剂的苯并咪唑衍生物

Family Applications After (1)

Application Number Title Priority Date Filing Date
CNA2007101491602A Pending CN101139346A (zh) 2003-05-19 2004-05-05 作为因子Xa抑制剂的苯并咪唑衍生物

Country Status (29)

Country Link
EP (2) EP1479676A1 (https=)
JP (1) JP4658940B2 (https=)
KR (1) KR20060014056A (https=)
CN (2) CN100484935C (https=)
AR (1) AR045683A1 (https=)
AT (1) ATE474838T1 (https=)
AU (1) AU2004238497B2 (https=)
BR (1) BRPI0410446A (https=)
CA (1) CA2526065A1 (https=)
CL (1) CL2004001078A1 (https=)
CR (1) CR8087A (https=)
DE (1) DE602004028240D1 (https=)
EC (1) ECSP056178A (https=)
MA (1) MA27798A1 (https=)
MX (1) MXPA05012231A (https=)
NO (1) NO20055910L (https=)
NZ (1) NZ543670A (https=)
OA (1) OA13168A (https=)
PA (1) PA8603501A1 (https=)
PE (1) PE20050198A1 (https=)
RS (1) RS20050856A (https=)
RU (1) RU2346944C2 (https=)
SA (1) SA04250196B1 (https=)
TN (1) TNSN05297A1 (https=)
TW (1) TW200503696A (https=)
UA (1) UA82100C2 (https=)
UY (1) UY28324A1 (https=)
WO (1) WO2004101553A1 (https=)
ZA (1) ZA200508151B (https=)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10342570A1 (de) * 2003-09-15 2005-04-14 Bayer Healthcare Ag Verfahren zur Herstellung von 4-(4-Aminophenyl)-3-morpholinon
EP1742637A4 (en) 2004-04-23 2011-06-08 Paratek Pharm Innc TRANSCRIPTION FACTOR MODULATION COMPOUNDS AND METHODS OF USE
WO2008033739A2 (en) * 2006-09-12 2008-03-20 Neurogen Corporation Benzimidazole carboxamide derivatives
DE102010018299A1 (de) 2010-04-23 2011-10-27 Archimica Gmbh Verfahren zur Herstellung von 4-(4-Aminophenyl)-morpholin-3-on
US9840489B2 (en) * 2013-12-20 2017-12-12 Institute Of Pharmacology And Toxicology Academy Of Military Medical Sciences P.L.A. China Piperidine carboxamide compound, preparation method, and usage thereof
JOP20190024A1 (ar) 2016-08-26 2019-02-19 Gilead Sciences Inc مركبات بيروليزين بها استبدال واستخداماتها
PL3759109T3 (pl) 2018-02-26 2024-03-04 Gilead Sciences, Inc. Podstawione związki pirolizyny jako inhibitory replikacji hbv

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4269846A (en) * 1979-10-29 1981-05-26 Usv Pharmaceutical Corporation Heterocyclic compounds useful as anti-allergy agents
JPH08208640A (ja) * 1995-02-06 1996-08-13 Nisshin Flour Milling Co Ltd ベンズイミダゾール誘導体およびそれを含有する心不全治療薬
JPH08295667A (ja) * 1995-04-27 1996-11-12 Takeda Chem Ind Ltd 複素環化合物、その製造法および剤
JPH09124609A (ja) * 1995-11-07 1997-05-13 Nissan Chem Ind Ltd ベンズイミダゾール誘導体
JPH10182459A (ja) * 1996-12-26 1998-07-07 Otsuka Pharmaceut Co Ltd cGMP分解酵素阻害剤
US6562828B1 (en) * 1998-04-10 2003-05-13 Japan Tobacco Inc. Amidine compounds

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GB1377642A (en) * 1971-01-14 1974-12-18 Koninklijke Gist Spiritus Penicillanic and cephalosporanic acid derivatives
JPH0784462B2 (ja) * 1986-07-25 1995-09-13 日清製粉株式会社 ベンゾイミダゾ−ル誘導体
US4897401A (en) * 1987-06-19 1990-01-30 Janssen Pharmaceutical N.V. N-(4-piperidinyl) bicyclic condensed 2-imidazolamine derivatives useful in treating allergic diseases
DE3828537A1 (de) * 1988-08-23 1990-03-01 Basf Ag Neue n-substituierte benzimidazol-2-carbonsaeureanilide, deren verwendung als lichtschutzmittel, insbesondere polymere und diese anilide enthaltendes organisches material
JPH0324609A (ja) * 1989-06-21 1991-02-01 Mitsuba Electric Mfg Co Ltd I/o用バッファic
JPH03184043A (ja) * 1989-12-14 1991-08-12 Fuji Photo Film Co Ltd ハロゲン化銀カラー写真感光材料
KR100190299B1 (ko) * 1990-07-19 1999-06-01 디르크 반테 신규한 옥사졸릴 유도체
DE4304650A1 (de) * 1993-02-16 1994-08-18 Thomae Gmbh Dr K Kondensierte 5-gliedrige Heterocyclen, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
SI9520096A (sl) * 1994-09-30 1998-04-30 Pfizer Inc. Derivati 2,7-substituiranega oktahidro-1H-pirido /1,2-a/ pirazina
UA62972C2 (en) * 1997-07-03 2004-01-15 Application of imidazopyrimidins and imidazopyridins for the treatment of neural disorders
WO2004022060A2 (en) * 2002-09-06 2004-03-18 Janssen Pharmaceutica, N.V. (1h-benzoimidazol-2-yl)-(piperazinyl)-methanone derivatives and related compounds as histamine h4-receptor antagonists for the treatment of inflammatory and allergic disorders

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4269846A (en) * 1979-10-29 1981-05-26 Usv Pharmaceutical Corporation Heterocyclic compounds useful as anti-allergy agents
JPH08208640A (ja) * 1995-02-06 1996-08-13 Nisshin Flour Milling Co Ltd ベンズイミダゾール誘導体およびそれを含有する心不全治療薬
JPH08295667A (ja) * 1995-04-27 1996-11-12 Takeda Chem Ind Ltd 複素環化合物、その製造法および剤
JPH09124609A (ja) * 1995-11-07 1997-05-13 Nissan Chem Ind Ltd ベンズイミダゾール誘導体
JPH10182459A (ja) * 1996-12-26 1998-07-07 Otsuka Pharmaceut Co Ltd cGMP分解酵素阻害剤
US6562828B1 (en) * 1998-04-10 2003-05-13 Japan Tobacco Inc. Amidine compounds

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DESIGN AND QUANTITATIVE STRUCTURE-ACTIVITYRELATIONSHIP OF3-AMIDINOBENZYL-1H-INDOLE-2-CARBOXAMIDES ASPOTENT,NONCHIRAL,AND SELECTIVE INHIBITORS OFBLOOD COAGULATION FACTOR Xa. MATTER,HANS ET AL.JOURNAL OF MEDICINAL CHEMISTRY,Vol.45 No.13. 2002 *
SYNTHESISANDANTIVIRALASSAYSOFSOME2-SUBSTITUTEDBENZIMIDAZOLE-N-CARBAMATES.GARUTI L.ET AL.FARMACO *

Also Published As

Publication number Publication date
CR8087A (es) 2006-09-22
RS20050856A (sr) 2007-11-15
JP4658940B2 (ja) 2011-03-23
MXPA05012231A (es) 2006-08-18
TW200503696A (en) 2005-02-01
WO2004101553A1 (en) 2004-11-25
PA8603501A1 (es) 2004-11-26
MA27798A1 (fr) 2006-03-01
ZA200508151B (en) 2007-02-28
UA82100C2 (uk) 2008-03-11
JP2006528213A (ja) 2006-12-14
CN1791598A (zh) 2006-06-21
CL2004001078A1 (es) 2005-04-08
RU2346944C2 (ru) 2009-02-20
TNSN05297A1 (en) 2007-07-10
OA13168A (en) 2006-12-13
NZ543670A (en) 2008-09-26
EP1479676A1 (en) 2004-11-24
NO20055910L (no) 2006-02-10
EP1636216A1 (en) 2006-03-22
RU2005139555A (ru) 2006-06-10
KR20060014056A (ko) 2006-02-14
AU2004238497B2 (en) 2010-07-22
PE20050198A1 (es) 2005-04-25
AR045683A1 (es) 2005-11-09
ATE474838T1 (de) 2010-08-15
BRPI0410446A (pt) 2006-06-06
EP1636216B1 (en) 2010-07-21
HK1089174A1 (zh) 2006-11-24
CN101139346A (zh) 2008-03-12
CA2526065A1 (en) 2004-11-25
AU2004238497A1 (en) 2004-11-25
SA04250196B1 (ar) 2008-11-18
ECSP056178A (es) 2006-08-30
WO2004101553B1 (en) 2005-03-03
UY28324A1 (es) 2004-12-31
DE602004028240D1 (de) 2010-09-02

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