SE461914B - Fosfonatanaloger av antiviruella nukleosidanaloger - Google Patents
Fosfonatanaloger av antiviruella nukleosidanalogerInfo
- Publication number
- SE461914B SE461914B SE8500307A SE8500307A SE461914B SE 461914 B SE461914 B SE 461914B SE 8500307 A SE8500307 A SE 8500307A SE 8500307 A SE8500307 A SE 8500307A SE 461914 B SE461914 B SE 461914B
- Authority
- SE
- Sweden
- Prior art keywords
- guanine
- compound
- virus
- hydrogen
- phosphonate
- Prior art date
Links
- 230000000840 anti-viral effect Effects 0.000 title description 13
- 239000002777 nucleoside Substances 0.000 title description 7
- 150000003833 nucleoside derivatives Chemical class 0.000 title description 5
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 39
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims description 34
- -1 5-trifluorothymine Chemical compound 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- RYYIULNRIVUMTQ-UHFFFAOYSA-N 6-chloroguanine Chemical compound NC1=NC(Cl)=C2N=CNC2=N1 RYYIULNRIVUMTQ-UHFFFAOYSA-N 0.000 claims description 5
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims description 5
- 229930024421 Adenine Natural products 0.000 claims description 5
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 5
- 229960000643 adenine Drugs 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- RHIULBJJKFDJPR-UHFFFAOYSA-N 5-ethyl-1h-pyrimidine-2,4-dione Chemical compound CCC1=CNC(=O)NC1=O RHIULBJJKFDJPR-UHFFFAOYSA-N 0.000 claims description 4
- KSNXJLQDQOIRIP-UHFFFAOYSA-N 5-iodouracil Chemical compound IC1=CNC(=O)NC1=O KSNXJLQDQOIRIP-UHFFFAOYSA-N 0.000 claims description 4
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- UFVWJVAMULFOMC-UHFFFAOYSA-N 6-amino-5-iodo-1h-pyrimidin-2-one Chemical compound NC=1NC(=O)N=CC=1I UFVWJVAMULFOMC-UHFFFAOYSA-N 0.000 claims description 4
- 208000036142 Viral infection Diseases 0.000 claims description 4
- 230000009385 viral infection Effects 0.000 claims description 4
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- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
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- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical group C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229940104230 thymidine Drugs 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
Classifications
-
- 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
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- 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
- 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)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Virology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Genetics & Genomics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49772083A | 1983-05-24 | 1983-05-24 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8500307D0 SE8500307D0 (sv) | 1985-01-23 |
| SE8500307L SE8500307L (sv) | 1985-01-23 |
| SE461914B true SE461914B (sv) | 1990-04-09 |
Family
ID=23978043
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8500307A SE461914B (sv) | 1983-05-24 | 1985-01-23 | Fosfonatanaloger av antiviruella nukleosidanaloger |
Country Status (8)
| Country | Link |
|---|---|
| EP (4) | EP0145739B1 (fr) |
| JP (1) | JPS60501407A (fr) |
| DE (1) | DE3490262T1 (fr) |
| GB (1) | GB2150570B (fr) |
| IT (1) | IT1209921B (fr) |
| NL (1) | NL8420134A (fr) |
| SE (1) | SE461914B (fr) |
| WO (1) | WO1984004748A1 (fr) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CS233665B1 (en) * | 1983-01-06 | 1985-03-14 | Antonin Holy | Processing of isomere o-phosphonylmethylderivative of anantiomere racemic vicinal diene |
| CA1288098C (fr) * | 1984-08-24 | 1991-08-27 | Richard L. Tolman | Les 4-(guanin-9-yl)butanals et leurs derives 3-oxa, 3-thia et 2-ene, a activite antivirale et antitumorale |
| CS263951B1 (en) * | 1985-04-25 | 1989-05-12 | Antonin Holy | 9-(phosponylmethoxyalkyl)adenines and method of their preparation |
| CS264222B1 (en) * | 1986-07-18 | 1989-06-13 | Holy Antonin | N-phosphonylmethoxyalkylderivatives of bases of pytimidine and purine and method of use them |
| US5650510A (en) * | 1986-11-18 | 1997-07-22 | Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic | Antiviral phosphonomethoxyalkylene purine and pyrimidine derivatives |
| JPH01501864A (ja) * | 1987-01-20 | 1989-06-29 | エス・アール・アイ・インターナシヨナル | 抗ウイルス剤 |
| CA1330794C (fr) * | 1987-03-27 | 1994-07-19 | Phillip Frost | Composes antiviraux, formes et methodes pharmaceutiques |
| EP0338168A1 (fr) * | 1988-04-19 | 1989-10-25 | Merrell Dow Pharmaceuticals Inc. | Dérivés de la phosphonoalkyl purine |
| EP0338887B1 (fr) * | 1988-04-19 | 1993-12-08 | Merrell Dow Pharmaceuticals Inc. | Dérivés de la phosphonoalkyl purine |
| JPH04505005A (ja) * | 1989-02-23 | 1992-09-03 | ユニバーシティ カレッジ ロンドン | ヌクレオシド類縁体 |
| CA2297294C (fr) * | 1989-05-15 | 2005-11-08 | Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic | Derives de phosphonomethoxymethylpurine/pyrimidine |
| 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 |
| GB8921469D0 (en) * | 1989-09-22 | 1989-11-08 | Erba Carlo Spa | 5'-alkylphosphonylnucleosides as antivirals |
| US5374626A (en) * | 1989-09-22 | 1994-12-20 | Farmitalia Carlo Erba | 5'-alkylphosphonylnucleosides as antivirals |
| US5302585A (en) * | 1990-04-20 | 1994-04-12 | Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic | Use of chiral 2-(phosphonomethoxy)propyl guanines as antiviral agents |
| EP0465297B1 (fr) * | 1990-07-04 | 1996-01-31 | Merrell Dow Pharmaceuticals Inc. | Dérivés d'acides 9-purinyl phosphoniques |
| EP0477454A1 (fr) * | 1990-09-28 | 1992-04-01 | Merrell Dow Pharmaceuticals Inc. | Dérivés phosphonates de certains nucléosides |
| US5208221A (en) * | 1990-11-29 | 1993-05-04 | Bristol-Myers Squibb Company | Antiviral (phosphonomethoxy) methoxy purine/pyrimidine derivatives |
| US5672697A (en) * | 1991-02-08 | 1997-09-30 | Gilead Sciences, Inc. | Nucleoside 5'-methylene phosphonates |
| US5494912A (en) * | 1991-06-26 | 1996-02-27 | Merrell Pharmaceuticals Inc. | 9-purinyl phosphonic acid derivitives for treating gout |
| DE69218968T2 (de) * | 1991-10-11 | 1997-10-09 | Inst Of Organic Chemistry And | Antivirale acyclische phosphonomethoxyalkyl substituierte, alkenyl und alkynyl purin und pyrimidin-derivate |
| US6057305A (en) * | 1992-08-05 | 2000-05-02 | Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic | Antiretroviral enantiomeric nucleotide analogs |
| RU2183213C2 (ru) * | 1996-11-05 | 2002-06-10 | ЗАО "Производственно-коммерческая ассоциация АЗТ" | Модифицированные нуклеозид-5'-трифосфаты как антивирусные агенты |
| CA2810928A1 (fr) | 2010-09-22 | 2012-03-29 | Alios Biopharma, Inc. | Analogues nucleotidiques substitues |
| AU2012358804B2 (en) | 2011-12-22 | 2018-04-19 | Alios Biopharma, Inc. | Substituted phosphorothioate nucleotide analogs |
| NZ631601A (en) | 2012-03-21 | 2016-06-24 | Alios Biopharma Inc | Solid forms of a thiophosphoramidate nucleotide prodrug |
| US9012427B2 (en) | 2012-03-22 | 2015-04-21 | Alios Biopharma, Inc. | Pharmaceutical combinations comprising a thionucleotide analog |
| JP6860585B2 (ja) * | 2016-03-09 | 2021-04-14 | ヤンセン バイオファーマ インク． | 非環状抗ウイルス 優先出願の参照による組み込み |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3238191A (en) * | 1962-09-13 | 1966-03-01 | Terrell C Myers | Phosphonic acid analogs of nucleoside phosphates and method |
| US3524846A (en) * | 1967-06-02 | 1970-08-18 | Syntex Corp | Process for the didealkylation of phosphonate esters |
| US3878194A (en) * | 1967-07-18 | 1975-04-15 | Syntex Inc | Novel phosphorylated phosphonium ylids |
| US3662031A (en) * | 1967-07-18 | 1972-05-09 | Syntex Corp | Phosphorylated phosphonium ylids |
| US3446793A (en) * | 1967-10-30 | 1969-05-27 | Syntex Corp | 3'-cyclic esters of 5'-deoxy-5'-(dihydroxyphosphinylmethyl)-nucleosides |
| US3560478A (en) * | 1968-06-14 | 1971-02-02 | Terrell C Myers | Analogues of nucleoside phosphates |
| CA931561A (en) * | 1969-03-10 | 1973-08-07 | Syntex Corporation | Nucleoside phosphonates, phosphonic acids, phosphonic acid salts, and process for producing same |
| AU521577B2 (en) * | 1977-02-24 | 1982-04-22 | Wellcome Foundation Limited, The | 9-hydroxyethoxymethyl guanine phosphates |
| US4287188A (en) * | 1977-02-24 | 1981-09-01 | Burroughs Wellcome Co. | Purine derivatives |
| US4291024A (en) * | 1978-04-10 | 1981-09-22 | Turcotte Joseph G | Cytotoxic liponucleotide analogs |
| EP0015584A3 (fr) * | 1979-03-12 | 1980-12-10 | Kailash Kumar Dr. Prof. Gauri | Nucléotides, procédés pour leur préparation et médicaments |
| US4347360A (en) * | 1980-09-16 | 1982-08-31 | Ens Bio Logicals Inc. | Ring open nucleoside analogues |
| DE3045375A1 (de) * | 1980-12-02 | 1982-07-01 | Robugen Gmbh Pharmazeutische Fabrik Esslingen A.N., 7300 Esslingen | Neue substituierte pyrimidin-nukleoside mit antiviraler wirkung, verfahren zu deren herstellung und daraus zubereitete arzneiformen |
| NZ201662A (en) * | 1981-08-26 | 1986-07-11 | Merck & Co Inc | 9-(1,3-(and 2,3)-dihydroxy-1-(and 2)-propoxy-methyl)guanine derivatives and methods for their preparation |
-
1984
- 1984-05-14 DE DE19843490262 patent/DE3490262T1/de not_active Ceased
- 1984-05-14 WO PCT/US1984/000737 patent/WO1984004748A1/fr active IP Right Grant
- 1984-05-14 EP EP84902178A patent/EP0145739B1/fr not_active Expired
- 1984-05-14 EP EP87116869A patent/EP0273169A3/fr not_active Withdrawn
- 1984-05-14 GB GB08500850A patent/GB2150570B/en not_active Expired
- 1984-05-14 NL NL8420134A patent/NL8420134A/nl not_active Application Discontinuation
- 1984-05-14 EP EP87116867A patent/EP0274025A3/fr not_active Withdrawn
- 1984-05-14 EP EP87116868A patent/EP0272446B1/fr not_active Expired - Lifetime
- 1984-05-14 JP JP59501983A patent/JPS60501407A/ja active Pending
- 1984-05-22 IT IT8448236A patent/IT1209921B/it active
-
1985
- 1985-01-23 SE SE8500307A patent/SE461914B/sv not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0273169A2 (fr) | 1988-07-06 |
| SE8500307D0 (sv) | 1985-01-23 |
| SE8500307L (sv) | 1985-01-23 |
| JPS60501407A (ja) | 1985-08-29 |
| EP0273169A3 (fr) | 1990-08-29 |
| EP0272446B1 (fr) | 1992-11-11 |
| EP0274025A3 (fr) | 1990-08-29 |
| IT1209921B (it) | 1989-08-30 |
| EP0272446A1 (fr) | 1988-06-29 |
| IT8448236A0 (it) | 1984-05-22 |
| EP0145739B1 (fr) | 1989-02-08 |
| EP0145739A1 (fr) | 1985-06-26 |
| EP0274025A2 (fr) | 1988-07-13 |
| GB8500850D0 (en) | 1985-02-20 |
| WO1984004748A1 (fr) | 1984-12-06 |
| GB2150570A (en) | 1985-07-03 |
| NL8420134A (nl) | 1985-04-01 |
| DE3490262T1 (de) | 1985-11-28 |
| GB2150570B (en) | 1987-04-08 |
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Legal Events
| Date | Code | Title | Description |
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| NUG | Patent has lapsed |
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