ES2147728T3 - Metodo para producir camptotecina y analogos de camptotecina. - Google Patents

Metodo para producir camptotecina y analogos de camptotecina.

Info

Publication number
ES2147728T3
ES2147728T3 ES92903792T ES92903792T ES2147728T3 ES 2147728 T3 ES2147728 T3 ES 2147728T3 ES 92903792 T ES92903792 T ES 92903792T ES 92903792 T ES92903792 T ES 92903792T ES 2147728 T3 ES2147728 T3 ES 2147728T3
Authority
ES
Spain
Prior art keywords
camptotecine
subalkyl
analogs
produce
halo
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 - Lifetime
Application number
ES92903792T
Other languages
English (en)
Inventor
Daniel L Comins
Matthew F Baevsky
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.)
North Carolina State University
Original Assignee
North Carolina State University
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
Application filed by North Carolina State University filed Critical North Carolina State University
Application granted granted Critical
Publication of ES2147728T3 publication Critical patent/ES2147728T3/es
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • 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
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 to ring carbon atoms
    • C07D215/18—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/24—Oxygen atoms attached in position 8
    • C07D215/26—Alcohols; Ethers thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 to ring carbon atoms
    • C07D215/36—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C07D215/40—Nitrogen atoms attached in position 8
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Hematology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Oncology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Quinoline Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

COMPUESTO DE FORMULA (1) SE HACEN DA ACUERDO CON EL SIGUIENTE ESQUEMA: (II) + (III) -> (IV) -> (I) , EN DONDE R PUEDE SER UN SUBAQUIL, SUBALCOXIL; R1 PUEDE SER H, SUBALQUIL, SUBALCOXIL, O HALO; R2, R3, R4, Y R5 PUEDEN SER INDEPENDIENTEMENTE CADA UNO H, ANIDA, HIDROXILO, SUBALQUIL, SUBACOXIL SUBTIOALQUIL, DE (SUBALQUIL) AMINA, CIANO, DIOXILMETIDENO, FORMILO, NITRO, HALO, TRIFLUOROMETIL, ANIMAMETIL, AZIDA, AMIDA, HIDRAACIDO O ALGUNOS DE LOS VEINTE AMINOACIDOS ESTANDAR ENLAZADOS A UNA CADENA A POR EL ATOMO AMINO-NITROGENO,; Y ES H Y W Y X SON HALOGENOS. TAMBIEN SE REVELA UN PROCESO NUEVO PARA FABRICAR MATERIALES A PARTIR DEL ESQUEMA CITADO, Y NUEVOS ENLACES EMPLEADOS EN ESTOS PROCESOS.
ES92903792T 1990-12-20 1991-12-18 Metodo para producir camptotecina y analogos de camptotecina. Expired - Lifetime ES2147728T3 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US07/632,970 US5162532A (en) 1990-12-20 1990-12-20 Intermediates and method of making camptothecin and camptothecin analogs

Publications (1)

Publication Number Publication Date
ES2147728T3 true ES2147728T3 (es) 2000-10-01

Family

ID=24537745

Family Applications (2)

Application Number Title Priority Date Filing Date
ES99112300T Expired - Lifetime ES2241211T3 (es) 1990-12-20 1991-12-18 Productos intermedios para preparar camptotecina y analogos de camptotecina.
ES92903792T Expired - Lifetime ES2147728T3 (es) 1990-12-20 1991-12-18 Metodo para producir camptotecina y analogos de camptotecina.

Family Applications Before (1)

Application Number Title Priority Date Filing Date
ES99112300T Expired - Lifetime ES2241211T3 (es) 1990-12-20 1991-12-18 Productos intermedios para preparar camptotecina y analogos de camptotecina.

Country Status (10)

Country Link
US (2) US5162532A (es)
EP (2) EP0565621B1 (es)
JP (3) JP3141069B2 (es)
AT (2) ATE194348T1 (es)
CA (3) CA2112351C (es)
DE (2) DE69132292T2 (es)
DK (2) DK0565621T3 (es)
ES (2) ES2241211T3 (es)
GR (1) GR3034146T3 (es)
WO (1) WO1992011263A1 (es)

Families Citing this family (48)

* Cited by examiner, † Cited by third party
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US5552154A (en) 1989-11-06 1996-09-03 The Stehlin Foundation For Cancer Research Method for treating cancer with water-insoluble s-camptothecin of the closed lactone ring form and derivatives thereof
US5212317A (en) * 1990-12-20 1993-05-18 North Carolina State University Methods and intermediates for the assymmetric synthesis of camptothecin and camptothecin analogs
US5191082A (en) * 1990-12-20 1993-03-02 North Carolina State University Camptothecin intermediate and method of making camptothecin intermediates
US5247089A (en) * 1990-12-20 1993-09-21 North Carolina State University Method of making intermediates useful for the manufacture of camptothecin and camptothecin analogs
US6080751A (en) * 1992-01-14 2000-06-27 The Stehlin Foundation For Cancer Research Method for treating pancreatic cancer in humans with water-insoluble S-camptothecin of the closed lactone ring form and derivatives thereof
US5459269A (en) * 1992-06-18 1995-10-17 North Carolina State University 14-halo-camptothecins
US5428166A (en) * 1992-06-18 1995-06-27 North Carolina State University Method of making asymmetric de ring intermediates for the synthesis of camptothecin and camptothecin analogs
US5391745A (en) * 1992-07-23 1995-02-21 Sloan-Kettering Institute For Cancer Research Methods of preparation of camptothecin analogs
US5446047A (en) * 1992-07-23 1995-08-29 Sloan-Kettering Institute For Cancer Research Camptothecin analogues
US5405963A (en) * 1993-06-10 1995-04-11 Smithkline Beecham Corporation Process for asymmetric total synthesis of camptothecin analogues
US5475108A (en) * 1993-08-31 1995-12-12 North Carolina State University Camptothecin intermediates and method of making camptothecin and comptothecin analogs
US5395939A (en) * 1993-11-30 1995-03-07 North Carolina State University Method of making asymmetric de ring intermediates for the synthesis of camptothecin and camptothecin analogs
GB9402934D0 (en) * 1994-02-16 1994-04-06 Erba Carlo Spa Camptothecin derivatives and process for their preparation
US5491237A (en) * 1994-05-03 1996-02-13 Glaxo Wellcome Inc. Intermediates in pharmaceutical camptothecin preparation
JPH0873461A (ja) * 1994-09-06 1996-03-19 Yakult Honsha Co Ltd 新規なカンプトテシン誘導体、その製造法および抗腫瘍剤
WO1996011005A2 (en) * 1994-10-06 1996-04-18 Atlas Leon T Use of camptothecin or derivatives thereof for the manufacture of a medicament for the treatment of viral diseases
US5496952A (en) * 1995-02-07 1996-03-05 North Carolina State University Method of making asymmetric DE ring intermediates for the synthesis of camptothecin and camptothecin analogs
US5942386A (en) * 1995-06-07 1999-08-24 Thomas Jefferson University Anti-fungal agents and methods of identifying and using the same
US6815546B2 (en) 1995-06-21 2004-11-09 Societe De Recherches Et D'applications Scientifiques (S.C.R.A.S.) Analogues of camptothecin, their use as medicaments and the pharmaceutical compositions containing them
US6797715B1 (en) * 1995-06-21 2004-09-28 Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.) Analogues of camptothecin, their use as medicaments and the pharmaceutical compositions containing them
MX9710228A (es) * 1995-06-21 1998-03-31 Sod Conseils Rech Applic Nuevos analogos de camptotecina, procedimientos de preparacion, su aplicacion como medicinas y las composiciones farmaceuticas que los comprenden.
WO1998004557A1 (en) * 1996-07-30 1998-02-05 Bionumerik Pharmaceuticals, Inc. Novel process for preparing camptothecin
US6559309B2 (en) 1996-11-01 2003-05-06 Osi Pharmaceuticals, Inc. Preparation of a camptothecin derivative by intramolecular cyclisation
JP4094710B2 (ja) 1997-11-06 2008-06-04 株式会社ヤクルト本社 新規なカンプトテシン誘導体
CA2385528C (en) 1999-10-01 2013-12-10 Immunogen, Inc. Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents
DE60136490D1 (de) * 2000-11-09 2008-12-18 Neopharm Inc Sn-38-lipidkomplexe und verfahren zu ihrer verwendung
WO2003030864A1 (en) 2001-05-29 2003-04-17 Neopharm, Inc. Liposomal formulation of irinotecan
US7049322B2 (en) * 2002-02-21 2006-05-23 Supergen, Inc. Compositions and formulations of 9-nitrocamptothecin polymorphs and methods of use therefor
KR100651728B1 (ko) * 2004-11-10 2006-12-06 한국전자통신연구원 정착기를 갖는 전자 소자용 화합물 및 이를 포함하는 전자소자와 이들의 제조 방법
JP4861340B2 (ja) * 2005-02-22 2012-01-25 エフ．ホフマン−ラ ロシュ アーゲー カンプトセシンサブユニットの新規の合成法
RU2447889C2 (ru) * 2005-07-18 2012-04-20 Бипар Сайенсиз, Инк. Способ лечения рака (варианты)
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US20100279327A1 (en) * 2006-06-12 2010-11-04 Bipar Sciences, Inc. Method of treating diseases with parp inhibitors
US20070292883A1 (en) * 2006-06-12 2007-12-20 Ossovskaya Valeria S Method of treating diseases with PARP inhibitors
JP2008081492A (ja) 2006-08-31 2008-04-10 Banyu Pharmaceut Co Ltd オーロラａ選択的阻害作用を有する新規アミノピリジン誘導体
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CN101522609A (zh) 2006-09-05 2009-09-02 彼帕科学公司 癌症的治疗
US7977336B2 (en) 2006-12-28 2011-07-12 Banyu Pharmaceutical Co. Ltd Aminopyrimidine derivatives as PLK1 inhibitors
EP2211854A4 (en) * 2007-10-19 2011-01-12 Bipar Sciences Inc METHODS AND COMPOSITIONS FOR THE TREATMENT OF CANCER USING BENZOPYRONE-TYPE PARP INHIBITORS
US8329711B2 (en) 2007-10-23 2012-12-11 Msd K.K. Pyridone-substituted-dihydropyrazolopyrimidinone derivative
JP2011503111A (ja) * 2007-11-12 2011-01-27 バイパー サイエンシズ，インコーポレイティド Ｐａｒｐ阻害剤単独又は抗腫瘍剤との組み合わせによる乳がんの治療
CA2705417A1 (en) * 2007-11-12 2009-05-22 Bipar Sciences, Inc. Treatment of uterine cancer and ovarian cancer with a parp inhibitor alone or in combination with anti-tumor agents
KR20100102637A (ko) * 2007-12-07 2010-09-24 바이파 사이언스 인코포레이티드 토포이소머라제 억제제 및 ｐａｒｐ 억제제의 병용물에 의한 암의 치료
US8288396B2 (en) 2009-02-25 2012-10-16 Msdkk Pyrimidopyrimidoindazole derivative
EP2403339B1 (en) 2009-03-06 2017-01-18 Merck Sharp & Dohme Corp. Combination cancer therapy with an akt inhibitor and other anticancer agents
CN104163797A (zh) * 2014-05-14 2014-11-26 遵义医学院 一种4-羟基-1，2，3，4-四氢喹啉的合成方法
BR112022017064A2 (pt) 2020-02-25 2022-11-16 Mediboston Inc Derivados da camptotecina e seus conjugados
US12521444B2 (en) 2021-02-25 2026-01-13 Fortvita Biologics Limited Anti-HER2 antibody-drug conjugates and uses thereof

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FI80022C (fi) * 1982-07-05 1990-04-10 Otsuka Pharma Co Ltd Foerfarande foer framstaellning av ett nytt, terapeutiskt anvaendbart karbostyrilderivat.
US4894456A (en) * 1987-03-31 1990-01-16 Research Triangle Institute Synthesis of camptothecin and analogs thereof
GB8800502D0 (en) * 1988-01-11 1988-02-10 Cerestar Holding Bv Method of adding borax/boric acid to mixing/reaction-zone
JPH0615547B2 (ja) * 1988-01-20 1994-03-02 株式会社ヤクルト本社 新規なカンプトテシン誘導体

Also Published As

Publication number Publication date
CA2112351C (en) 1998-02-10
DK0565621T3 (da) 2000-10-09
JP2001064257A (ja) 2001-03-13
WO1992011263A1 (en) 1992-07-09
EP0963988A3 (en) 2001-07-11
DE69133455D1 (de) 2005-06-02
DK0963988T3 (da) 2005-07-25
JP3262781B2 (ja) 2002-03-04
EP0565621B1 (en) 2000-07-05
DE69133455T2 (de) 2006-04-27
JP2001055377A (ja) 2001-02-27
ATE194348T1 (de) 2000-07-15
JP3234828B2 (ja) 2001-12-04
DE69132292D1 (de) 2000-08-10
HK1025565A1 (en) 2000-11-17
EP0963988B1 (en) 2005-04-27
EP0963988A2 (en) 1999-12-15
GR3034146T3 (en) 2000-11-30
CA2214037A1 (en) 1992-07-09
US5321140A (en) 1994-06-14
JPH06504062A (ja) 1994-05-12
EP0565621A1 (en) 1993-10-20
ATE294182T1 (de) 2005-05-15
CA2214037C (en) 2001-11-27
CA2324848C (en) 2005-07-26
CA2324848A1 (en) 1992-07-09
ES2241211T3 (es) 2005-10-16
CA2112351A1 (en) 1992-07-09
DE69132292T2 (de) 2001-02-22
EP0565621A4 (en) 1995-08-09
JP3141069B2 (ja) 2001-03-05
US5162532A (en) 1992-11-10

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