DE3855575D1 - Wasserlösliche Camptothecin-Analoge - Google Patents
Wasserlösliche Camptothecin-AnalogeInfo
- Publication number
- DE3855575D1 DE3855575D1 DE3855575T DE3855575T DE3855575D1 DE 3855575 D1 DE3855575 D1 DE 3855575D1 DE 3855575 T DE3855575 T DE 3855575T DE 3855575 T DE3855575 T DE 3855575T DE 3855575 D1 DE3855575 D1 DE 3855575D1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- hydrogen
- water soluble
- ch2nh2
- formyl
- 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
Links
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical class C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 title 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title 1
- 239000001257 hydrogen Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 abstract 1
- -1 -CH2NH2 Chemical group 0.000 abstract 1
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical group N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- 230000004565 tumor cell growth Effects 0.000 abstract 1
Classifications
-
- 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
- C07D491/12—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 three hetero rings
- C07D491/14—Ortho-condensed systems
-
- 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
- C07D491/22—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 four or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Steroid Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Semiconductor Lasers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12714887A | 1987-12-01 | 1987-12-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3855575D1 true DE3855575D1 (de) | 1996-10-31 |
| DE3855575T2 DE3855575T2 (de) | 1997-03-20 |
Family
ID=22428545
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3855575T Expired - Lifetime DE3855575T2 (de) | 1987-12-01 | 1988-11-30 | Wasserlösliche Camptothecin-Analoge |
| DE1997175017 Active DE19775017I2 (de) | 1987-12-01 | 1988-11-30 | Wasserloesliche Camptothecin-Analoge |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1997175017 Active DE19775017I2 (de) | 1987-12-01 | 1988-11-30 | Wasserloesliche Camptothecin-Analoge |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US5004758A (de) |
| EP (1) | EP0321122B1 (de) |
| JP (1) | JPH0633268B2 (de) |
| KR (1) | KR930009357B1 (de) |
| CN (3) | CN1027265C (de) |
| AT (1) | ATE143368T1 (de) |
| AU (1) | AU612735B2 (de) |
| CA (1) | CA1308102C (de) |
| CY (1) | CY2017A (de) |
| DE (2) | DE3855575T2 (de) |
| DK (1) | DK173034B1 (de) |
| ES (1) | ES2094721T3 (de) |
| FI (1) | FI89923C (de) |
| GR (1) | GR3021990T3 (de) |
| HK (1) | HK81097A (de) |
| IE (1) | IE74873B1 (de) |
| IL (1) | IL88517A (de) |
| LU (2) | LU90026I2 (de) |
| MX (1) | MX9203744A (de) |
| NL (1) | NL970017I2 (de) |
| NO (2) | NO170487C (de) |
| NZ (1) | NZ227124A (de) |
| PT (1) | PT89111B (de) |
| SG (1) | SG66254A1 (de) |
| ZA (1) | ZA888938B (de) |
Families Citing this family (141)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5364858A (en) * | 1987-03-31 | 1994-11-15 | Research Triangle Institute | Camptothecin analogs as potent inhibitors of topoisomerase I |
| US5053512A (en) * | 1987-04-14 | 1991-10-01 | Research Triangle Institute | Total synthesis of 20(S) and 20(R)-camptothecin and compthothecin derivatives |
| US5106742A (en) * | 1987-03-31 | 1992-04-21 | Wall Monroe E | Camptothecin analogs as potent inhibitors of topoisomerase I |
| US5227380A (en) * | 1987-03-31 | 1993-07-13 | Research Triangle Institute | Pharmaceutical compositions and methods employing camptothecins |
| US5122526A (en) * | 1987-03-31 | 1992-06-16 | Research Triangle Institute | Camptothecin and analogs thereof and pharmaceutical compositions and method using them |
| US5340817A (en) * | 1987-04-14 | 1994-08-23 | Research Triangle Institute | Method of treating tumors with anti-tumor effective camptothecin compounds |
| US5122606A (en) * | 1987-04-14 | 1992-06-16 | Research Triangle Institute | 10,11-methylenedioxy camptothecins |
| US5049668A (en) * | 1989-09-15 | 1991-09-17 | Research Triangle Institute | 10,11-methylenedioxy-20(RS)-camptothecin analogs |
| US5180722A (en) * | 1987-04-14 | 1993-01-19 | Research Triangle Institute | 10,11-methylenedioxy-20(RS)-camptothecin and 10,11-methylenedioxy-20(S)-camptothecin analogs |
| US4939255A (en) * | 1987-06-24 | 1990-07-03 | Daiichi Pharmaceutical Co., Ltd. | Hexa-cyclic camptothecin derivatives |
| 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 |
| JP2684104B2 (ja) * | 1990-02-09 | 1997-12-03 | 株式会社ヤクルト本社 | 新規なカンプトテシン誘導体 |
| ATE186461T1 (de) * | 1990-09-28 | 1999-11-15 | Smithkline Beecham Corp | Verfahren zur herstellung wasserlöslicher camptothecinanaloge, sowie die verbindungen 10- hydroxy-11-c(1-6)-alkoxycamptothecin |
| US5883255A (en) * | 1990-10-31 | 1999-03-16 | Smithkline Beecham Corporation | Substituted indolizino 1,2-b!quinolinones |
| WO1992014469A1 (en) * | 1991-02-21 | 1992-09-03 | Smithkline Beecham Corporation | Treatment of ovarian cancer |
| KR930702984A (ko) * | 1991-02-21 | 1993-11-29 | 스튜어트 알. 슈터 | 비-소세포 폐암의 치료 |
| CA2104449A1 (en) * | 1991-02-21 | 1992-08-22 | Randall Keith Johnson | Treatment of esophageal cancer |
| ATE136898T1 (de) * | 1991-10-29 | 1996-05-15 | Glaxo Wellcome Inc | Wasserlösliche camptothecinderivate |
| US5559235A (en) * | 1991-10-29 | 1996-09-24 | Glaxo Wellcome Inc. | Water soluble camptothecin derivatives |
| ES2204894T3 (es) | 1991-11-15 | 2004-05-01 | Smithkline Beecham Corporation | Composicion que contiene cisplatino y topotecan como agente antitumoral. |
| AU2394392A (en) * | 1991-12-10 | 1993-07-19 | Smithkline Beecham Corporation | Treatment of colorectal cancer |
| 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 |
| 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 |
| US5614549A (en) * | 1992-08-21 | 1997-03-25 | Enzon, Inc. | High molecular weight polymer-based prodrugs |
| WO1994004160A1 (en) * | 1992-08-21 | 1994-03-03 | Dana Farber Cancer Institute | Treatment of human viral infections |
| US5342947A (en) * | 1992-10-09 | 1994-08-30 | Glaxo Inc. | Preparation of water soluble camptothecin derivatives |
| AP9300587A0 (en) * | 1992-11-12 | 1995-05-05 | Glaxo Inc | Water soluble camptothecin derivatives. |
| US5674872A (en) * | 1993-08-20 | 1997-10-07 | Smithkline Beecham Corporation | Treatment of ovarian cancer |
| US5622986A (en) * | 1993-10-20 | 1997-04-22 | Enzon, Inc. | 2'-and/or 7-substituted taxanes |
| US5880131A (en) * | 1993-10-20 | 1999-03-09 | Enzon, Inc. | High molecular weight polymer-based prodrugs |
| US5436243A (en) * | 1993-11-17 | 1995-07-25 | Research Triangle Institute Duke University | Aminoanthraquinone derivatives to combat multidrug resistance |
| US5447936A (en) * | 1993-12-22 | 1995-09-05 | Bionumerik Pharmaceuticals, Inc. | Lactone stable formulation of 10-hydroxy 7-ethyl camptothecin and methods for uses thereof |
| GB9402934D0 (en) * | 1994-02-16 | 1994-04-06 | Erba Carlo Spa | Camptothecin derivatives and process for their preparation |
| US5468754A (en) * | 1994-04-19 | 1995-11-21 | Bionumerik Pharmaceuticals, Inc. | 11,7 substituted camptothecin derivatives and formulations of 11,7 substituted camptothecin derivatives and methods for uses thereof |
| DE69531611T2 (de) * | 1994-04-28 | 2004-02-26 | Bionumerik Pharmaceuticals, Inc., San Antonio | Lactone-stabile camptothecin oder 7 - ethyl camptothecin - formulierung in dimethylisosorbid oder dimethylacetamid |
| US5597829A (en) * | 1994-05-09 | 1997-01-28 | Bionumerik Pharmaceuticals, Inc. | Lactone stable formulation of camptothecin and methods for uses thereof |
| US5604233A (en) * | 1994-04-28 | 1997-02-18 | Bionumerik Pharmaceuticals, Inc. | Lactone stable formulation of 7-ethyl camptothecin and methods for uses thereof |
| US5491237A (en) | 1994-05-03 | 1996-02-13 | Glaxo Wellcome Inc. | Intermediates in pharmaceutical camptothecin preparation |
| US5834442A (en) * | 1994-07-07 | 1998-11-10 | Barbara Ann Karmanos Cancer Institute | Method for inhibiting cancer metastasis by oral administration of soluble modified citrus pectin |
| US5646159A (en) * | 1994-07-20 | 1997-07-08 | Research Triangle Institute | Water-soluble esters of camptothecin compounds |
| US6504029B1 (en) * | 1995-04-10 | 2003-01-07 | Daiichi Pharmaceutical Co., Ltd. | Condensed-hexacyclic compounds and a process therefor |
| GB9510716D0 (en) * | 1995-05-26 | 1995-07-19 | Pharmacia Spa | Substituted camptothecin derivatives and process for their preparation |
| US5670500A (en) * | 1995-05-31 | 1997-09-23 | Smithkline Beecham Corporation | Water soluble camptothecin analogs |
| US5663177A (en) * | 1995-05-31 | 1997-09-02 | Smithkline Beecham Corporation | Water soluble camptothecin analogs |
| WO1996040886A1 (en) * | 1995-06-07 | 1996-12-19 | Thomas Jefferson University | Anti-fungal agents and methods of identifying and using the same |
| WO1997019085A1 (en) * | 1995-11-22 | 1997-05-29 | Research Triangle Institute | Camptothecin compounds with combined topoisomerase i inhibition and dna alkylation properties |
| US6395541B1 (en) | 1996-05-23 | 2002-05-28 | The Rockefeller University | Methods for the identification of compounds capable of inhibiting HIV-1 viral replication employing murine cell lines expressing human topoisomerase I |
| ES2214634T3 (es) * | 1996-08-19 | 2004-09-16 | Bionumerik Pharmaceuticals, Inc. | Derivados muy lipofilos de la camptotecina. |
| US6013505A (en) * | 1996-10-08 | 2000-01-11 | Smithkline Beecham Corporation | Topoisomerase I |
| US6025156A (en) * | 1996-10-15 | 2000-02-15 | Smithkline Beecham Corporation | Topoisomerase III |
| US5962303A (en) | 1996-10-15 | 1999-10-05 | Smithkline Beecham Corporation | Topoisomerase III |
| US6559309B2 (en) | 1996-11-01 | 2003-05-06 | Osi Pharmaceuticals, Inc. | Preparation of a camptothecin derivative by intramolecular cyclisation |
| CA2280905C (en) * | 1997-02-14 | 2006-08-29 | Bionumerik Pharmaceuticals, Inc. | Highly lipophilic camptothecin derivatives |
| US6207673B1 (en) | 1997-03-12 | 2001-03-27 | The University Of North Carolina At Chapel Hill | Covalent conjugates of topoisomerase I and topoisomerase II inhibitors |
| ID23424A (id) | 1997-05-14 | 2000-04-20 | Bayer Ag | Glikokonjugat dari 20(s)-kamptotesin |
| US6046209A (en) * | 1997-05-27 | 2000-04-04 | Smithkline Beecham Corporation | Water soluble camptothecin analogs |
| KR100289860B1 (ko) * | 1997-07-17 | 2001-05-15 | 나카무라 하사오 | 크로만의 제조 방법 |
| US6011042A (en) * | 1997-10-10 | 2000-01-04 | Enzon, Inc. | Acyl polymeric derivatives of aromatic hydroxyl-containing compounds |
| US6214821B1 (en) | 1998-03-05 | 2001-04-10 | Washington State University Research Foundation | Methods and composition for the inhibition of cancer cells |
| SK1732001A3 (en) * | 1998-08-05 | 2001-06-11 | Aventis Pharma Sa | Use of camptothecin derivatives, with reduced gastrointestinal toxicity |
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| FR2801309B1 (fr) * | 1999-11-18 | 2002-01-04 | Adir | Nouveaux composes analogues de la camptothecine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
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| US8129330B2 (en) * | 2002-09-30 | 2012-03-06 | Mountain View Pharmaceuticals, Inc. | Polymer conjugates with decreased antigenicity, methods of preparation and uses thereof |
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| US8034831B2 (en) * | 2002-11-06 | 2011-10-11 | Celgene Corporation | Methods for the treatment and management of myeloproliferative diseases using 4-(amino)-2-(2,6-Dioxo(3-piperidyl)-isoindoline-1,3-dione in combination with other therapies |
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| WO2004055020A1 (en) * | 2002-12-16 | 2004-07-01 | Council Of Scientific And Industrial Research | Process for the direct preparation of 5-alkoxy and 5-acyloxy analogues of campthothecins or mappicene ketones |
| FR2852606A1 (fr) * | 2003-03-18 | 2004-09-24 | Inst Nat Sante Rech Med | Moyens pour inhiber simultanement l'expression de plusieurs genes impliques dans une pathologie |
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| EP1732947B1 (de) * | 2004-03-05 | 2011-04-27 | Vegenics Pty Ltd | Materialien und verfahren für wachstumsfaktorbindende konstrukte |
| CA2562904C (en) * | 2004-04-27 | 2013-07-02 | Wellstat Biologics Corporation | Cancer treatment using viruses and camptothecins |
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| US7122700B2 (en) * | 2004-07-30 | 2006-10-17 | Xerox Corporation | Arylamine processes |
| WO2006069344A2 (en) | 2004-12-22 | 2006-06-29 | Rutgers, The State University Of New Jersey | Controlled release hydrogels |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US4399282A (en) * | 1979-07-10 | 1983-08-16 | Kabushiki Kaisha Yakult Honsha | Camptothecin derivatives |
| US4342776A (en) * | 1979-11-05 | 1982-08-03 | Merck & Co., Inc. | 4-Substituted-3-hydroxy-3-pyrroline-2,5-dione inhibitors of glycolic acid oxidase |
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| US4473692A (en) * | 1981-09-04 | 1984-09-25 | Kabushiki Kaisha Yakult Honsha | Camptothecin derivatives and process for preparing same |
| JPS58154582A (ja) * | 1982-03-10 | 1983-09-14 | Yakult Honsha Co Ltd | 新規なカンプトテシン誘導体およびその製造法 |
| JPS58154584A (ja) * | 1982-03-10 | 1983-09-14 | Yakult Honsha Co Ltd | 5位ヒドロキシ置換カンプトテシン誘導体の製造法 |
| JPS5951289A (ja) * | 1982-09-17 | 1984-03-24 | Yakult Honsha Co Ltd | 新規な9−置換−カンプトテシン誘導体 |
| JPS59227884A (ja) * | 1983-06-09 | 1984-12-21 | Yakult Honsha Co Ltd | 新規な7−ヒドロキシアルキルカンプトテシン誘導体 |
| JPS6019790A (ja) * | 1983-07-14 | 1985-01-31 | Yakult Honsha Co Ltd | 新規なカンプトテシン誘導体 |
| US4775759A (en) * | 1984-11-27 | 1988-10-04 | The United States Of America As Represented By The Department Of Health And Human Services | Synthesis and utilization of 17-methyl and 17-cyclopropylmethyl-3,14-dihydroxy-4,5α-epoxy 6β-fluoromorphinans (foxy and cyclofoxy) as (18F)-labeled opioid ligands for position emission transaxial tomography (PETT) |
| US4820816A (en) * | 1985-08-02 | 1989-04-11 | President And Fellows Of Harvard College | 3-trifuoromethylsulfonyloxy-substituted 1-carbacephalosporins as intermediates for antibiotics |
| JPH0615546B2 (ja) * | 1986-02-24 | 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 |
| US4894456A (en) * | 1987-03-31 | 1990-01-16 | Research Triangle Institute | Synthesis of camptothecin and analogs thereof |
| JP3431931B2 (ja) * | 1992-07-16 | 2003-07-28 | 旭電化工業株式会社 | 銅及び銅合金の表面処理方法 |
-
1988
- 1988-11-02 US US07/266,460 patent/US5004758A/en not_active Expired - Lifetime
- 1988-11-28 IL IL8851788A patent/IL88517A/en not_active IP Right Cessation
- 1988-11-28 DK DK198806636A patent/DK173034B1/da not_active IP Right Cessation
- 1988-11-29 PT PT89111A patent/PT89111B/pt not_active IP Right Cessation
- 1988-11-29 ZA ZA888938A patent/ZA888938B/xx unknown
- 1988-11-29 NZ NZ227124A patent/NZ227124A/en unknown
- 1988-11-30 AT AT88311366T patent/ATE143368T1/de active
- 1988-11-30 SG SG1996005126A patent/SG66254A1/en unknown
- 1988-11-30 LU LU90026C patent/LU90026I2/fr unknown
- 1988-11-30 NO NO885352A patent/NO170487C/no not_active IP Right Cessation
- 1988-11-30 IE IE357688A patent/IE74873B1/en not_active IP Right Cessation
- 1988-11-30 DE DE3855575T patent/DE3855575T2/de not_active Expired - Lifetime
- 1988-11-30 CA CA000584544A patent/CA1308102C/en not_active Expired - Lifetime
- 1988-11-30 ES ES88311366T patent/ES2094721T3/es not_active Expired - Lifetime
- 1988-11-30 AU AU26394/88A patent/AU612735B2/en not_active Expired
- 1988-11-30 EP EP88311366A patent/EP0321122B1/de not_active Expired - Lifetime
- 1988-11-30 FI FI885569A patent/FI89923C/fi not_active IP Right Cessation
- 1988-11-30 DE DE1997175017 patent/DE19775017I2/de active Active
- 1988-12-01 JP JP63306769A patent/JPH0633268B2/ja not_active Expired - Lifetime
- 1988-12-01 KR KR1019880015971A patent/KR930009357B1/ko not_active Expired - Lifetime
- 1988-12-01 CN CN88108256A patent/CN1027265C/zh not_active Expired - Lifetime
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1992
- 1992-06-29 MX MX9203744A patent/MX9203744A/es unknown
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1993
- 1993-02-27 CN CN93102886A patent/CN1035380C/zh not_active Expired - Lifetime
- 1993-06-28 CN CN93107879A patent/CN1037574C/zh not_active Expired - Lifetime
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1996
- 1996-12-11 GR GR960403426T patent/GR3021990T3/el unknown
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1997
- 1997-03-27 NL NL970017C patent/NL970017I2/nl unknown
- 1997-04-16 LU LU90053C patent/LU90053I2/fr unknown
- 1997-06-12 HK HK81097A patent/HK81097A/en not_active IP Right Cessation
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1998
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- 1998-02-20 CY CY201798A patent/CY2017A/xx unknown
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