PT94041A - Processo para a preparacao de analogos de nucleosidos, em particulares derivadosde fosfonometoximetiloxi-purina/pirimidina e derivados de 4'-fosfonometoxitetra-hidrofuranil-1'purina/pirimidina, com accao anti-viral e anti-tumoral e de composicoes farmaceuticas que os contem - Google Patents
Processo para a preparacao de analogos de nucleosidos, em particulares derivadosde fosfonometoximetiloxi-purina/pirimidina e derivados de 4'-fosfonometoxitetra-hidrofuranil-1'purina/pirimidina, com accao anti-viral e anti-tumoral e de composicoes farmaceuticas que os contemInfo
- Publication number
- PT94041A PT94041A PT94041A PT9404190A PT94041A PT 94041 A PT94041 A PT 94041A PT 94041 A PT94041 A PT 94041A PT 9404190 A PT9404190 A PT 9404190A PT 94041 A PT94041 A PT 94041A
- Authority
- PT
- Portugal
- Prior art keywords
- purine
- pyrimidine
- derivatives
- alkyl
- viral
- Prior art date
Links
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 title abstract 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title abstract 4
- 230000000259 anti-tumor effect Effects 0.000 title abstract 2
- 230000000840 anti-viral effect Effects 0.000 title abstract 2
- JMFXQCYBSLMRQQ-UHFFFAOYSA-N P(=O)(O)(O)COOC1=NC=C2NC=NC2=N1 Chemical class P(=O)(O)(O)COOC1=NC=C2NC=NC2=N1 JMFXQCYBSLMRQQ-UHFFFAOYSA-N 0.000 title 1
- 230000001154 acute effect Effects 0.000 title 1
- 239000002777 nucleoside Substances 0.000 title 1
- 150000003833 nucleoside derivatives Chemical class 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 208000036142 Viral infection Diseases 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 1
- 150000002118 epoxides Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000009385 viral infection Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic 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
- C07D405/02—Heterocyclic 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
- C07D405/04—Heterocyclic 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/40—Heterocyclic compounds containing purine ring systems with halogen atoms or perhalogeno-alkyl radicals directly attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65616—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657181—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
- C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
- C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Genetics & Genomics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Biotechnology (AREA)
- Veterinary Medicine (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35230389A | 1989-05-15 | 1989-05-15 | |
| US48156990A | 1990-02-22 | 1990-02-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PT94041A true PT94041A (pt) | 1991-01-08 |
| PT94041B PT94041B (pt) | 1998-08-31 |
Family
ID=26997477
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT94041A PT94041B (pt) | 1989-05-15 | 1990-05-15 | Processo para a preparacao de analogos de nucleosidos, em particulares derivadosde fosfonometoximetiloxi-purina/pirimidina e derivados de 4'-fosfonometoxitetra-hidrofuranil-1'purina/pirimidina, com accao anti-viral e anti-tumoral e de composicoes farmaceuticas que os contem |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0398231B1 (pt) |
| JP (1) | JP2900064B2 (pt) |
| KR (3) | KR0167080B1 (pt) |
| AT (1) | ATE155480T1 (pt) |
| CA (2) | CA2297294C (pt) |
| DE (1) | DE69031057T2 (pt) |
| ES (1) | ES2104570T3 (pt) |
| FI (1) | FI902386A0 (pt) |
| IE (1) | IE81086B1 (pt) |
| PT (1) | PT94041B (pt) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5688778A (en) * | 1989-05-15 | 1997-11-18 | Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic | Nucleoside analogs |
| EP0477454A1 (en) * | 1990-09-28 | 1992-04-01 | Merrell Dow Pharmaceuticals Inc. | Novel phosphonate derivatives of certain nucleosides |
| US5221611A (en) * | 1991-06-19 | 1993-06-22 | Sigma Chemical Company | Ddi immunoassays, derivatives, conjugates and antibodies |
| US6235886B1 (en) * | 1993-09-03 | 2001-05-22 | Isis Pharmaceuticals, Inc. | Methods of synthesis and use |
| AU4848793A (en) | 1992-09-11 | 1994-04-12 | Isis Pharmaceuticals, Inc. | Oligonucleotide and nucleotide amine analogs, methods of synthesis and use |
| WO1994019327A1 (de) * | 1993-02-26 | 1994-09-01 | Max-Delbrück-Centrum für Molekulare Medizin | Nukleoside, ihre herstellung und ihre verwendung als therapeutikum und als baustein für synthetische oligonukleotide |
| EP0719274A1 (en) * | 1993-09-17 | 1996-07-03 | Gilead Sciences, Inc. | Method for dosing therapeutic compounds |
| JP4086314B2 (ja) * | 1993-09-17 | 2008-05-14 | ギリアード サイエンシーズ， インコーポレイテッド | ヌクレオチドアナログ |
| US5798340A (en) | 1993-09-17 | 1998-08-25 | Gilead Sciences, Inc. | Nucleotide analogs |
| US5656745A (en) * | 1993-09-17 | 1997-08-12 | Gilead Sciences, Inc. | Nucleotide analogs |
| US5659023A (en) * | 1995-02-01 | 1997-08-19 | Gilead Sciences, Inc. | Nucleotide analogues |
| US5977061A (en) * | 1995-04-21 | 1999-11-02 | Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic | N6 - substituted nucleotide analagues and their use |
| US5717095A (en) * | 1995-12-29 | 1998-02-10 | Gilead Sciences, Inc. | Nucleotide analogs |
| US6093816A (en) | 1996-06-27 | 2000-07-25 | Isis Pharmaceuticals, Inc. | Cationic lipids |
| RU2183213C2 (ru) * | 1996-11-05 | 2002-06-10 | ЗАО "Производственно-коммерческая ассоциация АЗТ" | Модифицированные нуклеозид-5'-трифосфаты как антивирусные агенты |
| CA2394654A1 (en) | 1999-12-17 | 2001-06-21 | Manfred Weigele | Proton pump inhibitors |
| EP1259520B1 (en) * | 1999-12-17 | 2006-05-24 | Ariad Pharmaceuticals, Inc. | Novel purines |
| PL207187B1 (pl) * | 2001-06-29 | 2010-11-30 | Acad Of Science Czech Republic | Pochodne 6-[2-(fosfonometoksy) alkoksy] pirymidyny, sposób ich wytwarzania, kompozycja farmaceutyczna zawierająca te pochodne oraz ich zastosowanie |
| AU2004247305B2 (en) | 2003-06-16 | 2010-02-18 | Institute Of Organic Chemistry And Biochemistry, Academy Of Sciences Of The Czech Republic | Pyrimidine compounds having phosphonate groups as antiviral nucleotide analogs |
| SG136123A1 (en) | 2004-03-04 | 2007-10-29 | Leuven K U Res & Dev | Phosponate nucleosides useful as active ingredients in pharmaceutical compositions for the treatment of viral infections, and intermediates for their production |
| PT1778251E (pt) * | 2004-07-27 | 2011-06-29 | Gilead Sciences Inc | Análogos de fosfonato de compostos inibidores de vih |
| US8895531B2 (en) | 2006-03-23 | 2014-11-25 | Rfs Pharma Llc | 2′-fluoronucleoside phosphonates as antiviral agents |
| US7842672B2 (en) | 2006-07-07 | 2010-11-30 | Gilead Sciences, Inc. | Phosphonate inhibitors of HCV |
| TWI444384B (zh) | 2008-02-20 | 2014-07-11 | Gilead Sciences Inc | 核苷酸類似物及其在治療惡性腫瘤上的用途 |
| WO2010068708A2 (en) | 2008-12-09 | 2010-06-17 | Rfs Pharma, Llc | 3'-azido purine nucleotide prodrugs for treatment of viral infections |
| CA2751458C (en) * | 2009-02-06 | 2018-06-05 | Rfs Pharma, Llc | Purine nucleoside monophosphate prodrugs for treatment of cancer and viral infections |
| IL295418B2 (en) | 2015-03-06 | 2023-10-01 | Atea Pharmaceuticals Inc | Cell-D-2'-deoxy-2'-alpha-fluoro-2'-cell-C-modified-2-different-N6-purine modified nucleotides for the treatment of hepatitis C virus |
| JP6978099B2 (ja) * | 2016-09-02 | 2021-12-08 | ディセルナ ファーマシューティカルズ インコーポレイテッド | ４’−リン酸アナログ及びそれを含むオリゴヌクレオチド |
| PT3512863T (pt) | 2016-09-07 | 2022-03-09 | Atea Pharmaceuticals Inc | Nucleótidos de purina 2'-substituídos-n6-substituídos para tratamento de vírus de rna |
| KR102335193B1 (ko) | 2017-02-01 | 2021-12-03 | 아테아 파마슈티컬즈, 인크. | C형 간염 바이러스를 치료하기 위한 뉴클레오티드 헤미-술페이트 염 |
| CN112351799A (zh) | 2018-04-10 | 2021-02-09 | 阿堤亚制药公司 | 具有硬化的hcv感染患者的治疗 |
| US10874687B1 (en) | 2020-02-27 | 2020-12-29 | Atea Pharmaceuticals, Inc. | Highly active compounds against COVID-19 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3457255A (en) * | 1967-05-17 | 1969-07-22 | Syntex Corp | Novel ribo and lyxo nucleoside derivatives and a process for their preparation |
| DE3027279A1 (de) * | 1980-07-18 | 1982-05-06 | Byk Gulden Lomberg Chemische Fabrik Gmbh, 7750 Konstanz | Substituierte adenosin-3',5'-phosphorsaeurebenzyltriester, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| CS233665B1 (en) * | 1983-01-06 | 1985-03-14 | Antonin Holy | Processing of isomere o-phosphonylmethylderivative of anantiomere racemic vicinal diene |
| SE8802173D0 (sv) * | 1988-06-10 | 1988-06-10 | Astra Ab | Pyrimidine derivatives |
-
1990
- 1990-04-27 CA CA002297294A patent/CA2297294C/en not_active Expired - Lifetime
- 1990-04-27 CA CA002479846A patent/CA2479846C/en not_active Expired - Lifetime
- 1990-05-14 DE DE69031057T patent/DE69031057T2/de not_active Expired - Lifetime
- 1990-05-14 ES ES90109066T patent/ES2104570T3/es not_active Expired - Lifetime
- 1990-05-14 FI FI902386A patent/FI902386A0/fi not_active Application Discontinuation
- 1990-05-14 EP EP90109066A patent/EP0398231B1/en not_active Expired - Lifetime
- 1990-05-14 AT AT90109066T patent/ATE155480T1/de not_active IP Right Cessation
- 1990-05-14 KR KR1019900006858A patent/KR0167080B1/ko not_active IP Right Cessation
- 1990-05-14 IE IE173390A patent/IE81086B1/en not_active IP Right Cessation
- 1990-05-15 JP JP2123262A patent/JP2900064B2/ja not_active Expired - Lifetime
- 1990-05-15 PT PT94041A patent/PT94041B/pt not_active IP Right Cessation
-
1998
- 1998-06-02 KR KR1019980002040A patent/KR0167090B1/ko not_active IP Right Cessation
- 1998-06-02 KR KR1019980020407A patent/KR0167089B1/ko not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0398231A3 (en) | 1993-06-02 |
| JPH035493A (ja) | 1991-01-11 |
| EP0398231B1 (en) | 1997-07-16 |
| CA2479846C (en) | 2007-07-24 |
| KR900018125A (ko) | 1990-12-20 |
| CA2297294C (en) | 2005-11-08 |
| KR0167080B1 (ko) | 1999-04-15 |
| KR0167090B1 (en) | 1999-03-30 |
| IE901733L (en) | 1990-11-15 |
| IE81086B1 (en) | 2000-03-08 |
| FI902386A0 (fi) | 1990-05-14 |
| CA2297294A1 (en) | 1990-11-15 |
| ATE155480T1 (de) | 1997-08-15 |
| JP2900064B2 (ja) | 1999-06-02 |
| ES2104570T3 (es) | 1997-10-16 |
| CA2479846A1 (en) | 1990-11-15 |
| PT94041B (pt) | 1998-08-31 |
| DE69031057T2 (de) | 1998-02-19 |
| KR0167089B1 (en) | 1999-03-30 |
| DE69031057D1 (de) | 1997-08-21 |
| EP0398231A2 (en) | 1990-11-22 |
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