IL88204A - Acyl derivatives of 2'-deoxyadenosine, 2'-deoxyguanosine, 2'-deoxycytidine and 2'-deoxythymidine and pharmaceutical compositions containing them - Google Patents
Acyl derivatives of 2'-deoxyadenosine, 2'-deoxyguanosine, 2'-deoxycytidine and 2'-deoxythymidine and pharmaceutical compositions containing themInfo
- Publication number
- IL88204A IL88204A IL8820488A IL8820488A IL88204A IL 88204 A IL88204 A IL 88204A IL 8820488 A IL8820488 A IL 8820488A IL 8820488 A IL8820488 A IL 8820488A IL 88204 A IL88204 A IL 88204A
- Authority
- IL
- Israel
- Prior art keywords
- acid
- carbon atoms
- acyl
- acyl group
- group derived
- Prior art date
Links
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- YKBGVTZYEHREMT-KVQBGUIXSA-N 2'-deoxyguanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 YKBGVTZYEHREMT-KVQBGUIXSA-N 0.000 title claims description 26
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Classifications
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- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
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- 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
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- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
- A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
- A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
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- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
- A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
- A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
- A61K31/7072—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid having two oxo groups directly attached to the pyrimidine ring, e.g. uridine, uridylic acid, thymidine, zidovudine
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- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
- A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
- A61K31/7076—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines containing purines, e.g. adenosine, adenylic acid
- A61K31/708—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines containing purines, e.g. adenosine, adenylic acid having oxo groups directly attached to the purine ring system, e.g. guanosine, guanylic acid
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- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
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- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US11592387A | 1987-10-28 | 1987-10-28 |
Publications (2)
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IL88204A0 IL88204A0 (en) | 1989-06-30 |
IL88204A true IL88204A (en) | 1996-06-18 |
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IL8820488A IL88204A (en) | 1987-10-28 | 1988-10-28 | Acyl derivatives of 2'-deoxyadenosine, 2'-deoxyguanosine, 2'-deoxycytidine and 2'-deoxythymidine and pharmaceutical compositions containing them |
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US (1) | US6020320A (sv) |
EP (2) | EP0355131B1 (sv) |
JP (2) | JP2637534B2 (sv) |
KR (1) | KR890701609A (sv) |
AT (2) | ATE142221T1 (sv) |
CA (1) | CA1329932C (sv) |
DE (2) | DE3856557T2 (sv) |
DK (1) | DK174400B1 (sv) |
FI (2) | FI91764C (sv) |
HK (1) | HK1004854A1 (sv) |
IL (1) | IL88204A (sv) |
IN (1) | IN167609B (sv) |
NO (1) | NO174392C (sv) |
WO (1) | WO1989003838A1 (sv) |
ZA (1) | ZA888083B (sv) |
Families Citing this family (32)
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---|---|---|---|---|
US5470838A (en) | 1987-10-28 | 1995-11-28 | Pro-Neuron, Inc. | Method of delivering exogenous uridine or cytidine using acylated uridine or cytidine |
US6743782B1 (en) * | 1987-10-28 | 2004-06-01 | Wellstat Therapeutics Corporation | Acyl deoxyribonucleoside derivatives and uses thereof |
US5736531A (en) | 1987-10-28 | 1998-04-07 | Pro-Neuron, Inc. | Compositions of chemotherapeutic agent or antiviral agent with acylated pyrimidine nucleosides |
US5968914A (en) * | 1987-10-28 | 1999-10-19 | Pro-Neuron, Inc. | Treatment of chemotherapeutic agent and antiviral agent toxicity with acylated pyrimidine nucleosides |
US7776838B1 (en) | 1987-10-28 | 2010-08-17 | Wellstat Therapeutics Corporation | Treatment of chemotherapeutic agent and antiviral agent toxicity with acylated pyrimidine nucleosides |
US5691320A (en) * | 1987-10-28 | 1997-11-25 | Pro-Neuron, Inc. | Acylated pyrimidine nucleosides for treatment of systemic inflammation and inflammatory hepatitis |
US6060459A (en) | 1987-10-28 | 2000-05-09 | Pro-Neuron, Inc. | Enhancing blood cell count with oxypurine nucleosides |
US6329350B1 (en) * | 1987-10-28 | 2001-12-11 | Pro-Neuron, Inc. | Pyrimidine nucleotide precursors for treatment of systemic inflammation and inflammatory hepatitis |
IE980216A1 (en) * | 1989-04-17 | 2000-02-23 | Scotia Holdings Plc | Anti-virals |
CA2444071C (en) * | 1991-02-08 | 2008-10-07 | Wellstat Therapeutics Corporation | Oxypurine nucleosides and their congeners, and acyl derivatives thereof, for improvement of hematopoiesis |
CA2111571C (en) * | 1991-07-05 | 2005-08-23 | Reid W. Von Borstel | Treatment of chemotherapeutic agent and antiviral agent toxicity with acylated pyrimidine nucleosides |
GB2260319B (en) * | 1991-10-07 | 1995-12-06 | Norsk Hydro As | Acyl derivatives of nucleosides and nucleoside analogues having anti-viral activity |
ATE282627T1 (de) * | 1992-12-08 | 2004-12-15 | Wellstat Therapeutics Corp | Pyrimidinnukleotid-vorläufer zur behandlung entzündlicher hepatitis |
US5641758A (en) * | 1993-11-10 | 1997-06-24 | Kluge; Michael | Cytarabine derivatives, the preparation and use thereof |
JP4408450B2 (ja) | 1994-07-01 | 2010-02-03 | ウェルスタット セラピューティクス コーポレイション | 全身性炎症および炎症性肝炎の処置のためのピリミジンヌクレオチド前駆体 |
EP0882734B1 (en) * | 1997-06-02 | 2009-08-26 | F. Hoffmann-La Roche Ag | 5'-Deoxy-cytidine derivatives |
US20020006913A1 (en) | 1997-11-04 | 2002-01-17 | Von Borstel Reid W. | Antimutagenic compositions for treatment and prevention of photodamage to skin |
AU2090099A (en) * | 1997-12-16 | 1999-07-05 | William Darwin Garner | Reduction of uv induced skin cancer by topical amines |
US6444652B1 (en) | 1998-08-10 | 2002-09-03 | Novirio Pharmaceuticals Limited | β-L-2'-deoxy-nucleosides for the treatment of hepatitis B |
PT1431304E (pt) | 1998-08-10 | 2015-03-09 | Novartis Ag | Beta-l-2'-desoxi-nucleosidos para o tratamento da hepatite b |
PT1171137E (pt) | 1999-02-23 | 2008-03-17 | Univ California | Utilização de triacetiluridina para o tratamento de perturbações mitocondriais |
US6576619B2 (en) * | 1999-05-24 | 2003-06-10 | Cv Therapeutics, Inc. | Orally active A1 adenosine receptor agonists |
US6787526B1 (en) | 2000-05-26 | 2004-09-07 | Idenix Pharmaceuticals, Inc. | Methods of treating hepatitis delta virus infection with β-L-2′-deoxy-nucleosides |
US6875751B2 (en) | 2000-06-15 | 2005-04-05 | Idenix Pharmaceuticals, Inc. | 3′-prodrugs of 2′-deoxy-β-L-nucleosides |
DE10117615A1 (de) * | 2001-04-07 | 2002-10-10 | Max Delbrueck Centrum | Verwendung von Nucleosiden, Nucleobasen und deren Derivaten zur verbesserten Gewinnung von adulten Stammzellen |
TWI244393B (en) | 2002-08-06 | 2005-12-01 | Idenix Pharmaceuticals Inc | Crystalline and amorphous forms of beta-L-2'-deoxythymidine |
CA2498731C (en) | 2002-09-13 | 2012-10-30 | Idenix (Cayman) Limited | .beta.-l-2'-deoxynucleosides for the treatment of resistant hbv strains and combination therapies |
WO2009045655A2 (en) | 2007-08-16 | 2009-04-09 | The Henry M. Jackson Foundation For The Advancement Of Military Medicine, Inc. | Compositions containing purine nucleosides and manganese and their uses |
WO2010090723A2 (en) * | 2009-02-04 | 2010-08-12 | University Of Georgia Research Foundation, Inc. | Methods of inhibiting fibrogenesis and treating fibrotic disease |
CA2797716C (en) | 2010-04-29 | 2018-09-11 | The Henry M. Jackson Foundation For The Advancement Of Military Medicine, Inc. | Compositions containing purine and pyrimidine nucleosides, peptides, and manganese and their uses |
US9446064B2 (en) | 2013-03-14 | 2016-09-20 | Epizyme, Inc. | Combination therapy for treating cancer |
AU2021202658A1 (en) | 2021-04-28 | 2022-11-17 | Fondazione Telethon | Gene therapy |
Family Cites Families (37)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3847898A (en) * | 1969-05-27 | 1974-11-12 | Upjohn Co | N4-trihaloethoxy carbonyl arabino-furanosyl cytosine 5'-esters |
US3585188A (en) * | 1969-06-16 | 1971-06-15 | Takeda Chemical Industries Ltd | Process for producing 2'-deoxyuridine |
DE1941942A1 (de) * | 1969-08-18 | 1971-03-04 | Sylven Bengt Prof Dr | Neues pharmazeutisches Mittel |
FR2096712A1 (en) * | 1970-06-29 | 1972-02-25 | Giraux Georges | Steroid/b group vitamin compsns - for prevention and treatment of skin-photosensitivity disorders |
US3894000A (en) * | 1971-01-27 | 1975-07-08 | Upjohn Co | Ara-cytidine derivatives and process of preparation |
US3975367A (en) * | 1971-06-08 | 1976-08-17 | The Upjohn Company | Arabinofuranosyl N4 -aminoacyl cytosine containing compounds |
DE2147094A1 (de) * | 1971-09-21 | 1973-04-05 | Robugen Gmbh | Virostatisch wirksames arzneimittel |
US3991045A (en) * | 1973-05-30 | 1976-11-09 | Asahi Kasei Kogyo Kabushiki Kaisha | N4 -acylarabinonucleosides |
US4048432A (en) * | 1976-05-17 | 1977-09-13 | Parke, Davis & Company | 9-(3,5-Di-O-acyl-β-D-arabinofuranosyl)adenine compounds and method for their production |
FR2358155A1 (fr) * | 1976-07-15 | 1978-02-10 | Lapinet Eugene | Composition pour le traitement et la prevention de l'irritation et de l'inflammation de la peau, de l'oeil et des muqueuses |
US4675189A (en) * | 1980-11-18 | 1987-06-23 | Syntex (U.S.A.) Inc. | Microencapsulation of water soluble active polypeptides |
JPS5791994A (en) * | 1980-11-26 | 1982-06-08 | Fuji Kagaku Kogyo Kk | 5'-o-(n-alkylcarbamoylalanyl)-5-fluorouridine and its preparation |
DE3100478A1 (de) | 1981-01-09 | 1982-08-12 | Dr. Thilo & Co GmbH, 8021 Sauerlach | 5'ester von pyrimidinnucleosiden mit antiviraler wirksamkeit, verfahren zur herstellung und daraus hergestellte arzneimittel |
JPS57156418A (en) * | 1981-03-19 | 1982-09-27 | Sumitomo Chem Co Ltd | Carcinostatic |
JPS5849315A (ja) * | 1981-09-18 | 1983-03-23 | Mitsui Pharmaceut Inc | 抗腫瘍剤 |
JPS58167589A (ja) * | 1982-03-26 | 1983-10-03 | Nissan Chem Ind Ltd | ピラゾ−ル誘導体、その製法および該誘導体を含有する除草剤 |
JPS58167598A (ja) * | 1982-03-29 | 1983-10-03 | Tanabe Seiyaku Co Ltd | アデノシン誘導体及びその製法 |
FR2536278A1 (fr) * | 1982-11-18 | 1984-05-25 | Dupont Michele | Nouvelle composition therapeutique utile notamment pour la cicatrisation des plaies |
DE3319282A1 (de) * | 1983-05-27 | 1984-11-29 | Gödecke AG, 1000 Berlin | Verwendung von adenosin bei der behandlung von herpes |
JPS59219235A (ja) * | 1983-05-30 | 1984-12-10 | Mitsui Toatsu Chem Inc | 消化性潰瘍用剤 |
DE3481191D1 (de) * | 1983-07-20 | 1990-03-08 | Teijin Ltd | Antineoplastisches mittel. |
JPS6028929A (ja) * | 1983-07-28 | 1985-02-14 | Hokuriku Seiyaku Co Ltd | 2’−デオキシグアノシンを有効成分とする消化性潰瘍治療剤 |
JPS6064907A (ja) * | 1983-09-17 | 1985-04-13 | Risuburan Prod:Kk | 水性ゲル状化粧料 |
JPS60126220A (ja) * | 1983-12-09 | 1985-07-05 | Otsuka Pharmaceut Factory Inc | 核酸成分組成物 |
FR2556727B1 (fr) * | 1983-12-19 | 1990-01-19 | Biostabilex Labo Pharma | Nouvelles compositions therapeutiques a base d'adn a haut poids moleculaire et leur procede de preparation |
JPS60174797A (ja) | 1984-02-21 | 1985-09-09 | Funai Corp | Ν−アロイルチミジン誘導体ならびに抗腫瘍活性物質の毒性低下剤 |
EP0227844B1 (en) * | 1985-07-22 | 1992-05-13 | Teijin Limited | Antiviral drug |
US4762823A (en) * | 1985-10-16 | 1988-08-09 | Sloan-Kettering Institute For Cancer Research | Nucleosides of 5-monofluoromethyluracil and 5-difluoromethyluracil |
ATE146077T1 (de) * | 1986-09-22 | 1996-12-15 | Janssen Pharmaceutica Nv | Serotonin-antagonisten zur behandlung von wunden |
US4758533A (en) * | 1987-09-22 | 1988-07-19 | Xmr Inc. | Laser planarization of nonrefractory metal during integrated circuit fabrication |
US5246708A (en) * | 1987-10-28 | 1993-09-21 | Pro-Neuron, Inc. | Methods for promoting wound healing with deoxyribonucleosides |
JP2638949B2 (ja) * | 1988-07-06 | 1997-08-06 | トヨタ自動車株式会社 | 誘導電導機の制御方法 |
JPH0628929A (ja) * | 1992-07-09 | 1994-02-04 | Fujikura Ltd | 絶縁電線 |
JPH0634913A (ja) * | 1992-07-15 | 1994-02-10 | Oki Electric Ind Co Ltd | 密着イメージセンサの光学構成方法 |
JP3251060B2 (ja) * | 1992-08-18 | 2002-01-28 | 電気化学工業株式会社 | 窒化珪素粉末 |
JPH06123917A (ja) * | 1992-08-24 | 1994-05-06 | Fuji Photo Film Co Ltd | 写真作製装置 |
JP3454951B2 (ja) * | 1994-12-12 | 2003-10-06 | 株式会社半導体エネルギー研究所 | 半導体装置の作製方法 |
-
1988
- 1988-10-27 EP EP88910239A patent/EP0355131B1/en not_active Expired - Lifetime
- 1988-10-27 ZA ZA888083A patent/ZA888083B/xx unknown
- 1988-10-27 DE DE3856557T patent/DE3856557T2/de not_active Expired - Fee Related
- 1988-10-27 WO PCT/US1988/003824 patent/WO1989003838A1/en active IP Right Grant
- 1988-10-27 DE DE3855513T patent/DE3855513T2/de not_active Expired - Fee Related
- 1988-10-27 KR KR1019890701195A patent/KR890701609A/ko not_active IP Right Cessation
- 1988-10-27 EP EP95203050A patent/EP0712629B1/en not_active Expired - Lifetime
- 1988-10-27 AT AT88910239T patent/ATE142221T1/de not_active IP Right Cessation
- 1988-10-27 JP JP63509388A patent/JP2637534B2/ja not_active Expired - Fee Related
- 1988-10-27 AT AT95203050T patent/ATE243039T1/de not_active IP Right Cessation
- 1988-10-27 CA CA000581430A patent/CA1329932C/en not_active Expired - Fee Related
- 1988-10-28 IL IL8820488A patent/IL88204A/en not_active IP Right Cessation
- 1988-10-28 IN IN754/MAS/88A patent/IN167609B/en unknown
-
1989
- 1989-06-26 FI FI893100A patent/FI91764C/sv not_active IP Right Cessation
- 1989-06-26 NO NO892642A patent/NO174392C/no not_active IP Right Cessation
- 1989-06-27 DK DK198903180A patent/DK174400B1/da not_active IP Right Cessation
-
1993
- 1993-11-17 US US08/153,163 patent/US6020320A/en not_active Expired - Fee Related
-
1994
- 1994-03-16 FI FI941245A patent/FI97891C/sv not_active IP Right Cessation
- 1994-10-26 JP JP6299158A patent/JP2764014B2/ja not_active Expired - Lifetime
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1998
- 1998-04-29 HK HK98103631A patent/HK1004854A1/xx not_active IP Right Cessation
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