AR023792A1 - Derivados 6-alquenilo- y 6-alquinilo-epotilona, los procedimientos para prepararlos y su empleo en productos farmaceuticos - Google Patents

Derivados 6-alquenilo- y 6-alquinilo-epotilona, los procedimientos para prepararlos y su empleo en productos farmaceuticos

Info

Publication number
AR023792A1
AR023792A1 ARP000102024A ARP000102024A AR023792A1 AR 023792 A1 AR023792 A1 AR 023792A1 AR P000102024 A ARP000102024 A AR P000102024A AR P000102024 A ARP000102024 A AR P000102024A AR 023792 A1 AR023792 A1 AR 023792A1
Authority
AR
Argentina
Prior art keywords
compounds
treatment
derivatives
tumors
therapy
Prior art date
Application number
ARP000102024A
Other languages
English (en)
Original Assignee
Bayer Schering Pharma Ag
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
Priority claimed from DE19921086A external-priority patent/DE19921086A1/de
Priority claimed from DE19954228A external-priority patent/DE19954228A1/de
Priority claimed from DE10015836A external-priority patent/DE10015836A1/de
Application filed by Bayer Schering Pharma Ag filed Critical Bayer Schering Pharma Ag
Publication of AR023792A1 publication Critical patent/AR023792A1/es

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic 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
    • C07D405/02Heterocyclic 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 two hetero rings
    • C07D405/06Heterocyclic 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 two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • A61P35/02Antineoplastic agents specific for leukemia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic 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
    • C07D405/02Heterocyclic 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 two hetero rings
    • C07D405/04Heterocyclic 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 two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic 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
    • C07D405/14Heterocyclic 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
    • 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
    • C07D413/04Heterocyclic 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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D413/06Heterocyclic 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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D417/02Heterocyclic 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 two hetero rings
    • C07D417/04Heterocyclic 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 two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D417/02Heterocyclic 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 two hetero rings
    • C07D417/06Heterocyclic 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 two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D493/00Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04Ortho-condensed systems

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Hematology (AREA)
  • Oncology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Nuevos derivados de 6-alquenil- y 6-alquinil-epotilona de la formula general (1) en la que R1a, R1b, R2a, R2b, R3a, R3b, R4, R5, R6, R7, A Y, D, E, G, yZ tienen los significados indicados en la memoria descriptiva. Los nuevos compuestos interactuanc on la tubulina, estabilizando la microtubulina formada. Soncapaces de influir específicamente sobre la fase de division celular, y son apropiados para el tratamiento de tumores malignos tales como por ejemplo, loscarcinomas de ovario, estomago,colon , adenocarcinomas, carcinoma de mama, pulmon, cabeza y cuello, melanoma maligno, la leucemia agua linfocítica ymielocítica. También son apropiados para la terapia contra la angiogénesis, así como el tratamiento de enfermedades inflamatoriascronicas (psoriasis,artritis). Para evitar las excrecencias celulares descontroladas sobre implantes medicinales y para mejorar la tolerancia a estos ultimos, estos compuestospueden ser incorporados sobre o dentro de los materiales poliméricosempleados para estos casos. Los compuestos pueden ser empleados solos o en combinacion conotros principios activos y sustancias de este tipo que se emplean en la terapia de los tumores, con el fin de lograr efectos sinérgicos o magnificados.
ARP000102024A 1999-04-30 2000-04-28 Derivados 6-alquenilo- y 6-alquinilo-epotilona, los procedimientos para prepararlos y su empleo en productos farmaceuticos AR023792A1 (es)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19921086A DE19921086A1 (de) 1999-04-30 1999-04-30 6-Alkenyl- und 6-Alkinyl-Epothilon Derivate, Verfahren zu deren Herstellung sowie ihre Verwendung in pharmazeutischen Präparaten
DE19954228A DE19954228A1 (de) 1999-11-04 1999-11-04 6-Alkenyl-und 6-Alkinyl-Epothilon-Derivate, Verfahren zu deren Herstellung sowie ihre Verwendung in pharmazeutischen Präparaten
DE10015836A DE10015836A1 (de) 2000-03-27 2000-03-27 6-Alkenyl- und 6-Alkinyl-Epothilon-Derivate, Verfahren zu deren Herstellung sowie ihre Verwendung in pharmazeutischen Präparaten

Publications (1)

Publication Number Publication Date
AR023792A1 true AR023792A1 (es) 2002-09-04

Family

ID=27213767

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP000102024A AR023792A1 (es) 1999-04-30 2000-04-28 Derivados 6-alquenilo- y 6-alquinilo-epotilona, los procedimientos para prepararlos y su empleo en productos farmaceuticos

Country Status (33)

Country Link
EP (1) EP1173441B1 (es)
JP (2) JP4024003B2 (es)
KR (1) KR100721488B1 (es)
CN (1) CN100368415C (es)
AR (1) AR023792A1 (es)
AT (1) ATE440847T1 (es)
BG (1) BG65601B1 (es)
BR (1) BR0010190A (es)
CA (2) CA2651653C (es)
CY (1) CY1109768T1 (es)
CZ (1) CZ299653B6 (es)
DE (1) DE60042821D1 (es)
DK (1) DK1173441T3 (es)
EA (1) EA011502B1 (es)
EE (1) EE05292B1 (es)
ES (1) ES2331506T3 (es)
HK (1) HK1046681B (es)
HR (1) HRP20010892A2 (es)
HU (1) HUP0201010A3 (es)
IL (1) IL145938A0 (es)
ME (1) MEP13908A (es)
MX (1) MXPA01011039A (es)
NO (1) NO328149B1 (es)
NZ (1) NZ514989A (es)
PE (1) PE20010116A1 (es)
PL (1) PL210762B1 (es)
PT (1) PT1173441E (es)
RS (1) RS51023B (es)
SI (1) SI1173441T1 (es)
SK (1) SK286858B6 (es)
TW (2) TWI280962B (es)
WO (1) WO2000066589A1 (es)
ZA (1) ZA200109859B (es)

Families Citing this family (44)

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EP1440973A3 (de) 1995-11-17 2004-10-20 Gesellschaft für biotechnologische Forschung mbH (GBF) Epothilonderivate, Herstellung und Mittel
HU229833B1 (en) 1996-11-18 2014-09-29 Biotechnolog Forschung Gmbh Epothilone d production process, and its use as cytostatic as well as phytosanitary agents
DE69734362T2 (de) 1996-12-03 2006-07-20 Sloan-Kettering Institute For Cancer Research Synthese von epothilonen, zwischenprodukte dazu, analoga und verwendungen davon
US6605599B1 (en) 1997-07-08 2003-08-12 Bristol-Myers Squibb Company Epothilone derivatives
US6365749B1 (en) 1997-12-04 2002-04-02 Bristol-Myers Squibb Company Process for the preparation of ring-opened epothilone intermediates which are useful for the preparation of epothilone analogs
US6399638B1 (en) 1998-04-21 2002-06-04 Bristol-Myers Squibb Company 12,13-modified epothilone derivatives
US6498257B1 (en) 1998-04-21 2002-12-24 Bristol-Myers Squibb Company 2,3-olefinic epothilone derivatives
US6518421B1 (en) * 2000-03-20 2003-02-11 Bristol-Myers Squibb Company Process for the preparation of epothilone analogs
US6593115B2 (en) 2000-03-24 2003-07-15 Bristol-Myers Squibb Co. Preparation of epothilone intermediates
DE10020899A1 (de) * 2000-04-20 2001-10-25 Schering Ag 9-Oxa-Epothilon-Derivate, Verfahren zu deren Herstellung sowie ihre Verwendung in pharmazeutischen Präparaten
UA75365C2 (en) * 2000-08-16 2006-04-17 Bristol Myers Squibb Co Epothilone analog polymorph modifications, a method for obtaining thereof (variants), a pharmaceutical composition based thereon
SK8552003A3 (en) 2001-01-25 2004-06-08 Bristol Myers Squibb Co Parenteral formulation containing epothilone analogs
WO2002058699A1 (en) 2001-01-25 2002-08-01 Bristol-Myers Squibb Company Pharmaceutical forms of epothilones for oral administration
NZ526870A (en) 2001-01-25 2005-11-25 Bristol Myers Squibb Co Methods of administering epothilone analogs for the treatment of cancer
HUP0400041A2 (hu) 2001-02-20 2004-04-28 Bristol-Myers Squibb Co. Epotilonszármazékok alkalmazása makacs tumorok kezelésére szolgáló gyógyszerkészítmények előállítására
HUP0303175A2 (hu) 2001-02-20 2003-12-29 Bristol-Myers Squibb Co. Epotilonszármazékok alkalmazása makacs tumorok kezelésére alkalmas gyógyszerkészítmény előállítására
CA2440555A1 (en) 2001-03-14 2002-09-19 Bristol-Myers Squibb Company Combination of epothilone analogs and chemotherapeutic agents for the treatment of proliferative diseases
JP2004532888A (ja) 2001-06-01 2004-10-28 ブリストル−マイヤーズ スクイブ カンパニー エポチロン誘導体
EP1340498A1 (en) * 2002-03-01 2003-09-03 Schering Aktiengesellschaft Use of epothilones in the treatment of brain diseases associated with proliferative processes
WO2003077903A1 (en) 2002-03-12 2003-09-25 Bristol-Myers Squibb Company C12-cyano epothilone derivatives
DK1483251T3 (da) 2002-03-12 2010-04-12 Bristol Myers Squibb Co C3-cyano-epothilon-derivater
TW200403994A (en) 2002-04-04 2004-03-16 Bristol Myers Squibb Co Oral administration of EPOTHILONES
TW200400191A (en) 2002-05-15 2004-01-01 Bristol Myers Squibb Co Pharmaceutical compositions and methods of using C-21 modified epothilone derivatives
WO2003105828A1 (en) 2002-06-14 2003-12-24 Bristol-Myers Squibb Company Combination of epothilone analogs and chemotherapeutic agents for the treatment of proliferative diseases
TWI291464B (en) 2002-09-23 2007-12-21 Bristol Myers Squibb Co Methods for the preparation, isolation and purification of epothilone B, and X-ray crystal structures of epothilone B
DE10361794B3 (de) * 2003-12-31 2005-10-06 Schering Ag Optisch aktive heteroaromatische ß-Hydroxy-Ester und Verfahren zu deren Herstellung sowie deren Verwendung als Zwischenprodukte bei der Epothilon-Totalsynthese
EP1559447A1 (en) 2004-01-30 2005-08-03 Institut National De La Sante Et De La Recherche Medicale (Inserm) Use of epothilones in the treatment of neuronal connectivity defects such as schizophrenia and autism
EP1640004A1 (en) * 2004-09-24 2006-03-29 Schering Aktiengesellschaft Use of epothilones in the treatment of bone metastases and bone tumors or cancers
US20060121511A1 (en) 2004-11-30 2006-06-08 Hyerim Lee Biomarkers and methods for determining sensitivity to microtubule-stabilizing agents
EP1674098A1 (en) * 2004-12-23 2006-06-28 Schering Aktiengesellschaft Stable and tolerable parental formulations of highly reactive organic drug substances with low or no solubility in water
CN100384419C (zh) * 2005-12-02 2008-04-30 菏泽睿鹰制药集团有限公司 一种埃坡霉素缓释植入组合物及应用
DE102007016046A1 (de) 2007-03-30 2008-10-23 Bayer Schering Pharma Aktiengesellschaft Verfahren zur Herstellung von Epothilonderivaten durch selektive katalytische Epoxidierung
EP2065054A1 (en) 2007-11-29 2009-06-03 Bayer Schering Pharma Aktiengesellschaft Combinations comprising a prostaglandin and uses thereof
DE102007059752A1 (de) 2007-12-10 2009-06-18 Bayer Schering Pharma Aktiengesellschaft Funktionalisierte, feste Polymernanopartikel enthaltend Epothilone
EP2070521A1 (en) 2007-12-10 2009-06-17 Bayer Schering Pharma Aktiengesellschaft Surface-modified nanoparticles
EP2210584A1 (en) 2009-01-27 2010-07-28 Bayer Schering Pharma Aktiengesellschaft Stable polymeric composition comprising an epothilone and an amphiphilic block copolymer
EP3566719A1 (en) 2010-05-18 2019-11-13 Cerulean Pharma Inc. Compositions and methods for treatment of autoimmune and other diseases
EP2793949B1 (en) 2011-12-23 2018-08-22 Innate Pharma Enzymatic conjugation of antibodies
EP2872894B1 (en) 2012-07-13 2019-04-17 Innate Pharma Screening of conjugated antibodies
EP2916872B1 (en) 2012-11-09 2019-02-27 Innate Pharma Recognition tags for tgase-mediated conjugation
EP2968582B1 (en) 2013-03-15 2020-07-01 Innate Pharma Solid phase tgase-mediated conjugation of antibodies
EP3010547B1 (en) 2013-06-20 2021-04-21 Innate Pharma Enzymatic conjugation of polypeptides
CN105517577A (zh) 2013-06-21 2016-04-20 先天制药公司 多肽的酶促偶联
WO2019092148A1 (en) 2017-11-10 2019-05-16 Innate Pharma Antibodies with functionalized glutamine residues

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JPS54115320A (en) * 1978-02-28 1979-09-07 Soda Aromatic Novel unsaturated keto acid and its manufacture
JP2653663B2 (ja) * 1988-02-15 1997-09-17 財団法人微生物化学研究会 1.3―ジヒドロキシ―8―デセン―5―オンを含む免疫賦活剤及び制癌剤
EP0469480A3 (en) * 1990-08-01 1993-03-10 Hoechst Aktiengesellschaft Process for stereoselective preparation of 5-substituted delta-lactones and their use
CA2281105A1 (en) * 1997-02-25 1998-09-03 Gesellschaft Fur Biotechnologische Forschung Mbh (Gbf) Epothilones with a modified side chain
DE59814067D1 (de) * 1997-08-09 2007-09-06 Bayer Schering Pharma Ag Neue epothilon-derivate, verfahren zu deren herstellung und ihre pharmazeutische verwendung

Also Published As

Publication number Publication date
ATE440847T1 (de) 2009-09-15
KR20020005737A (ko) 2002-01-17
EE05292B1 (et) 2010-04-15
CA2651653A1 (en) 2000-11-09
JP2002543203A (ja) 2002-12-17
TWI294292B (en) 2008-03-11
NO20015278D0 (no) 2001-10-29
PL351491A1 (en) 2003-04-22
CN100368415C (zh) 2008-02-13
EE200100568A (et) 2003-02-17
NO20015278L (no) 2001-12-21
HUP0201010A3 (en) 2005-02-28
HK1046681B (zh) 2008-08-29
BG65601B1 (bg) 2009-02-27
CZ20013885A3 (cs) 2002-04-17
ZA200109859B (en) 2003-02-28
NO328149B1 (no) 2009-12-21
EP1173441A1 (en) 2002-01-23
HRP20010892A2 (en) 2008-06-30
JP2007224038A (ja) 2007-09-06
PE20010116A1 (es) 2001-02-15
SI1173441T1 (sl) 2010-01-29
EA200101025A1 (ru) 2002-06-27
DK1173441T3 (da) 2009-12-07
PT1173441E (pt) 2009-11-06
TW200711679A (en) 2007-04-01
CA2651653C (en) 2012-02-14
ES2331506T3 (es) 2010-01-07
EA011502B1 (ru) 2009-04-28
WO2000066589A1 (en) 2000-11-09
CZ299653B6 (cs) 2008-10-08
RS51023B (sr) 2010-10-31
CY1109768T1 (el) 2014-09-10
KR100721488B1 (ko) 2007-05-23
EP1173441B1 (en) 2009-08-26
CN1349534A (zh) 2002-05-15
TWI280962B (en) 2007-05-11
SK286858B6 (sk) 2009-06-05
BR0010190A (pt) 2002-01-08
PL210762B1 (pl) 2012-02-29
SK15512001A3 (sk) 2002-05-09
YU77601A (sh) 2005-07-19
HK1046681A1 (en) 2003-01-24
HUP0201010A2 (en) 2002-08-28
BG106053A (en) 2002-05-31
DE60042821D1 (de) 2009-10-08
IL145938A0 (en) 2002-07-25
MXPA01011039A (es) 2003-06-30
CA2371226C (en) 2011-11-29
NZ514989A (en) 2004-02-27
CA2371226A1 (en) 2000-11-09
MEP13908A (en) 2010-06-10
JP4886578B2 (ja) 2012-02-29
JP4024003B2 (ja) 2007-12-19

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