DE69132292D1 - Verfahren zur herstellung von camptothecin und analogen camptothecinen - Google Patents
Verfahren zur herstellung von camptothecin und analogen camptothecinenInfo
- Publication number
- DE69132292D1 DE69132292D1 DE69132292T DE69132292T DE69132292D1 DE 69132292 D1 DE69132292 D1 DE 69132292D1 DE 69132292 T DE69132292 T DE 69132292T DE 69132292 T DE69132292 T DE 69132292T DE 69132292 D1 DE69132292 D1 DE 69132292D1
- Authority
- DE
- Germany
- Prior art keywords
- loweralkyl
- amino
- camptothecines
- analog
- loweralkoxy
- 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
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
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 |
PCT/US1991/009598 WO1992011263A1 (en) | 1990-12-20 | 1991-12-18 | Method of making camptothecin and camptothecin analogs |
Publications (2)
Publication Number | Publication Date |
---|---|
DE69132292D1 true DE69132292D1 (de) | 2000-08-10 |
DE69132292T2 DE69132292T2 (de) | 2001-02-22 |
Family
ID=24537745
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE69133455T Expired - Fee Related DE69133455T2 (de) | 1990-12-20 | 1991-12-18 | Verfahren zur Herstellung von Camptothecin und Camptothecin-Analoga |
DE69132292T Expired - Fee Related DE69132292T2 (de) | 1990-12-20 | 1991-12-18 | Verfahren zur herstellung von camptothecin und analogen camptothecinen |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE69133455T Expired - Fee Related DE69133455T2 (de) | 1990-12-20 | 1991-12-18 | Verfahren zur Herstellung von Camptothecin und Camptothecin-Analoga |
Country Status (11)
Country | Link |
---|---|
US (2) | US5162532A (de) |
EP (2) | EP0565621B1 (de) |
JP (3) | JP3141069B2 (de) |
AT (2) | ATE294182T1 (de) |
CA (3) | CA2112351C (de) |
DE (2) | DE69133455T2 (de) |
DK (2) | DK0565621T3 (de) |
ES (2) | ES2147728T3 (de) |
GR (1) | GR3034146T3 (de) |
HK (1) | HK1025565A1 (de) |
WO (1) | WO1992011263A1 (de) |
Families Citing this family (46)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
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 |
US5459269A (en) * | 1992-06-18 | 1995-10-17 | North Carolina State University | 14-halo-camptothecins |
US5446047A (en) * | 1992-07-23 | 1995-08-29 | Sloan-Kettering Institute For Cancer Research | Camptothecin analogues |
US5391745A (en) * | 1992-07-23 | 1995-02-21 | Sloan-Kettering Institute For Cancer Research | Methods of preparation of camptothecin analogs |
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 |
WO1996040886A1 (en) * | 1995-06-07 | 1996-12-19 | 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 |
PL185354B1 (pl) * | 1995-06-21 | 2003-04-30 | Sod Conseils Rech Applic | Nowe analogi kamptotecyny, sposoby ich wytwarzania, ich zastosowanie jako leków oraz zawierające je kompozycje farmaceutyczne |
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 |
US6218540B1 (en) * | 1996-07-30 | 2001-04-17 | Bionumerik Pharmaceuticals, Inc. | 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 |
PL363618A1 (en) * | 2000-11-09 | 2004-11-29 | Neopharm, Inc. | Sn-38 lipid complexes and methods of use |
WO2003030864A1 (en) | 2001-05-29 | 2003-04-17 | Neopharm, Inc. | Liposomal formulation of irinotecan |
US7071202B2 (en) * | 2002-02-21 | 2006-07-04 | 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 |
ATE531719T1 (de) * | 2005-02-22 | 2011-11-15 | Hoffmann La Roche | Neue synthese einer camptothecin-untereinheit |
NZ587586A (en) * | 2005-07-18 | 2012-04-27 | Bipar Sciences Inc | Treatment of cancer |
AR060635A1 (es) | 2006-04-27 | 2008-07-02 | Banyu Pharma Co Ltd | Derivados de 1,2-dihidro-3h-pirazolo[3,4-d]pirimidin-3-ona, composiciones farmaceuticas que los comprenden y su uso en el tratamiento del cancer |
US20100279327A1 (en) * | 2006-06-12 | 2010-11-04 | Bipar Sciences, Inc. | Method of treating diseases with parp inhibitors |
CA2655257A1 (en) * | 2006-06-12 | 2008-12-04 | Bipar Sciences, Inc. | 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 |
CN101534836B (zh) | 2006-09-05 | 2011-09-28 | 彼帕科学公司 | Parp抑制剂在制备治疗肥胖症的药物中的用途 |
US8143447B2 (en) | 2006-09-05 | 2012-03-27 | Bipar Sciences, Inc. | Treatment of cancer |
US7977336B2 (en) | 2006-12-28 | 2011-07-12 | Banyu Pharmaceutical Co. Ltd | Aminopyrimidine derivatives as PLK1 inhibitors |
JP2011500684A (ja) * | 2007-10-19 | 2011-01-06 | バイパー サイエンシズ,インコーポレイティド | ベンゾピロン系parp阻害剤を用いる癌の処置方法および組成物 |
AU2008315048A1 (en) | 2007-10-23 | 2009-04-30 | Msd K.K. | Pyridone-substituted-dihydropyrazolopyrimidinone derivative |
NZ586125A (en) | 2007-11-12 | 2012-12-21 | Bipar Sciences Inc | Treatment of breast cancer with a parp inhibitor alone or in combination with anti-tumor agents |
WO2009064444A2 (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 |
CN101888777A (zh) * | 2007-12-07 | 2010-11-17 | 彼帕科学公司 | 用拓扑异构酶抑制剂和parp抑制剂的组合治疗癌症 |
EP2401281A4 (de) | 2009-02-25 | 2012-08-15 | Msd Kk | Pyrimidinpyrimidoindazolderivat |
US8481503B2 (en) | 2009-03-06 | 2013-07-09 | 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 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4578381A (en) * | 1982-07-05 | 1986-03-25 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivatives |
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 |
-
1990
- 1990-12-20 US US07/632,970 patent/US5162532A/en not_active Expired - Lifetime
-
1991
- 1991-12-18 EP EP92903792A patent/EP0565621B1/de not_active Expired - Lifetime
- 1991-12-18 CA CA002112351A patent/CA2112351C/en not_active Expired - Fee Related
- 1991-12-18 ES ES92903792T patent/ES2147728T3/es not_active Expired - Lifetime
- 1991-12-18 DK DK92903792T patent/DK0565621T3/da active
- 1991-12-18 ES ES99112300T patent/ES2241211T3/es not_active Expired - Lifetime
- 1991-12-18 AT AT99112300T patent/ATE294182T1/de not_active IP Right Cessation
- 1991-12-18 AT AT92903792T patent/ATE194348T1/de not_active IP Right Cessation
- 1991-12-18 DK DK99112300T patent/DK0963988T3/da active
- 1991-12-18 EP EP99112300A patent/EP0963988B1/de not_active Expired - Lifetime
- 1991-12-18 DE DE69133455T patent/DE69133455T2/de not_active Expired - Fee Related
- 1991-12-18 WO PCT/US1991/009598 patent/WO1992011263A1/en active IP Right Grant
- 1991-12-18 JP JP04503829A patent/JP3141069B2/ja not_active Expired - Fee Related
- 1991-12-18 CA CA002214037A patent/CA2214037C/en not_active Expired - Fee Related
- 1991-12-18 DE DE69132292T patent/DE69132292T2/de not_active Expired - Fee Related
- 1991-12-18 CA CA002324848A patent/CA2324848C/en not_active Expired - Fee Related
-
1993
- 1993-02-12 US US08/017,648 patent/US5321140A/en not_active Expired - Lifetime
-
2000
- 2000-06-02 HK HK00103380A patent/HK1025565A1/xx not_active IP Right Cessation
- 2000-07-25 JP JP2000224114A patent/JP3262781B2/ja not_active Expired - Fee Related
- 2000-07-25 JP JP2000224113A patent/JP3234828B2/ja not_active Expired - Fee Related
- 2000-08-08 GR GR20000401841T patent/GR3034146T3/el not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
HK1025565A1 (en) | 2000-11-17 |
JP2001064257A (ja) | 2001-03-13 |
JP2001055377A (ja) | 2001-02-27 |
US5162532A (en) | 1992-11-10 |
EP0963988A3 (de) | 2001-07-11 |
EP0565621A1 (de) | 1993-10-20 |
DK0963988T3 (da) | 2005-07-25 |
CA2324848C (en) | 2005-07-26 |
JP3234828B2 (ja) | 2001-12-04 |
CA2214037C (en) | 2001-11-27 |
EP0963988A2 (de) | 1999-12-15 |
US5321140A (en) | 1994-06-14 |
CA2324848A1 (en) | 1992-07-09 |
CA2112351A1 (en) | 1992-07-09 |
ATE294182T1 (de) | 2005-05-15 |
DE69133455D1 (de) | 2005-06-02 |
ES2147728T3 (es) | 2000-10-01 |
DK0565621T3 (da) | 2000-10-09 |
JP3262781B2 (ja) | 2002-03-04 |
EP0565621A4 (de) | 1995-08-09 |
DE69132292T2 (de) | 2001-02-22 |
EP0565621B1 (de) | 2000-07-05 |
JPH06504062A (ja) | 1994-05-12 |
CA2214037A1 (en) | 1992-07-09 |
CA2112351C (en) | 1998-02-10 |
WO1992011263A1 (en) | 1992-07-09 |
JP3141069B2 (ja) | 2001-03-05 |
EP0963988B1 (de) | 2005-04-27 |
DE69133455T2 (de) | 2006-04-27 |
ES2241211T3 (es) | 2005-10-16 |
ATE194348T1 (de) | 2000-07-15 |
GR3034146T3 (en) | 2000-11-30 |
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