DK170049B1 - Phosphonomethoxyalkylenpurin- og pyrimidinderivater samt farmaceutiske præparater indeholdende sådanne derivater - Google Patents
Phosphonomethoxyalkylenpurin- og pyrimidinderivater samt farmaceutiske præparater indeholdende sådanne derivater Download PDFInfo
- Publication number
- DK170049B1 DK170049B1 DK604087A DK604087A DK170049B1 DK 170049 B1 DK170049 B1 DK 170049B1 DK 604087 A DK604087 A DK 604087A DK 604087 A DK604087 A DK 604087A DK 170049 B1 DK170049 B1 DK 170049B1
- Authority
- DK
- Denmark
- Prior art keywords
- guanine
- ethyl
- phosphonomethoxy
- hydrogen
- compounds
- Prior art date
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- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 title claims description 17
- 150000003230 pyrimidines Chemical class 0.000 title claims description 5
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 title description 4
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 4
- 239000000825 pharmaceutical preparation Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 86
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical group O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims description 78
- -1 guanine-9- yl Chemical group 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 230000000840 anti-viral effect Effects 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- GPTFURBXHJWNHR-UHFFFAOYSA-N protopine Chemical group C1=C2C(=O)CC3=CC=C4OCOC4=C3CN(C)CCC2=CC2=C1OCO2 GPTFURBXHJWNHR-UHFFFAOYSA-N 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 5
- MSSXOMSJDRHRMC-UHFFFAOYSA-N 9H-purine-2,6-diamine Chemical compound NC1=NC(N)=C2NC=NC2=N1 MSSXOMSJDRHRMC-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- MWBWWFOAEOYUST-UHFFFAOYSA-N 2-aminopurine Chemical compound NC1=NC=C2N=CNC2=N1 MWBWWFOAEOYUST-UHFFFAOYSA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- MXSMRDDXWJSGMC-UHFFFAOYSA-N n-(6-oxo-3,7-dihydropurin-2-yl)acetamide Chemical compound N1C(NC(=O)C)=NC(=O)C2=C1N=CN2 MXSMRDDXWJSGMC-UHFFFAOYSA-N 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- WYDKPTZGVLTYPG-UHFFFAOYSA-N 2,8-diamino-3,7-dihydropurin-6-one Chemical group N1C(N)=NC(=O)C2=C1N=C(N)N2 WYDKPTZGVLTYPG-UHFFFAOYSA-N 0.000 claims description 2
- CRYCZDRIXVHNQB-UHFFFAOYSA-N 2-amino-8-bromo-3,7-dihydropurin-6-one Chemical group N1C(N)=NC(=O)C2=C1N=C(Br)N2 CRYCZDRIXVHNQB-UHFFFAOYSA-N 0.000 claims description 2
- YCFWZXAEOXKNHL-UHFFFAOYSA-N 2-amino-8-chloro-3,7-dihydropurin-6-one Chemical group N1C(N)=NC(=O)C2=C1N=C(Cl)N2 YCFWZXAEOXKNHL-UHFFFAOYSA-N 0.000 claims description 2
- TXGWTBFCLADKKR-UHFFFAOYSA-N 2-amino-8-hydrazinyl-3,7-dihydropurin-6-one Chemical group N1=C(N)NC(=O)C2=C1N=C(NN)N2 TXGWTBFCLADKKR-UHFFFAOYSA-N 0.000 claims description 2
- DJGMEMUXTWZGIC-UHFFFAOYSA-N 2-amino-8-methyl-3,7-dihydropurin-6-one Chemical group N1C(N)=NC(=O)C2=C1N=C(C)N2 DJGMEMUXTWZGIC-UHFFFAOYSA-N 0.000 claims description 2
- LRSASMSXMSNRBT-UHFFFAOYSA-N 5-methylcytosine Chemical compound CC1=CNC(=O)N=C1N LRSASMSXMSNRBT-UHFFFAOYSA-N 0.000 claims description 2
- CZJGCEGNCSGRBI-UHFFFAOYSA-N 6-amino-5-ethyl-1h-pyrimidin-2-one Chemical compound CCC1=CNC(=O)N=C1N CZJGCEGNCSGRBI-UHFFFAOYSA-N 0.000 claims description 2
- CLGFIVUFZRGQRP-UHFFFAOYSA-N 7,8-dihydro-8-oxoguanine Chemical group O=C1NC(N)=NC2=C1NC(=O)N2 CLGFIVUFZRGQRP-UHFFFAOYSA-N 0.000 claims description 2
- 229960003087 tioguanine Drugs 0.000 claims description 2
- WYMKPVYTVNNZNW-UHFFFAOYSA-N 3-(2-amino-6-oxo-3h-purin-9-yl)propoxymethylphosphonic acid Chemical group N1C(N)=NC(=O)C2=C1N(CCCOCP(O)(O)=O)C=N2 WYMKPVYTVNNZNW-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 48
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- 239000000203 mixture Substances 0.000 description 32
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 31
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- 239000000543 intermediate Substances 0.000 description 17
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- 125000006239 protecting group Chemical group 0.000 description 11
- 229910000104 sodium hydride Inorganic materials 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
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- 239000002904 solvent Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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- 238000000034 method Methods 0.000 description 9
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- 238000010790 dilution Methods 0.000 description 8
- 239000012895 dilution Substances 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
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- 238000012360 testing method Methods 0.000 description 8
- 230000003612 virological effect Effects 0.000 description 8
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 7
- 241000700605 Viruses Species 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
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- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 6
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- NZVORGQIEFTOQZ-UHFFFAOYSA-N 9-[2-(phosphonomethoxy)ethyl]guanine Chemical compound N1C(N)=NC(=O)C2=C1N(CCOCP(O)(O)=O)C=N2 NZVORGQIEFTOQZ-UHFFFAOYSA-N 0.000 description 5
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- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
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- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 4
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- SPSDEXPWUORORO-UHFFFAOYSA-N 2-amino-9-[2-(diethoxyphosphorylmethoxy)ethyl]-3h-purin-6-one Chemical compound N1C(N)=NC(=O)C2=C1N(CCOCP(=O)(OCC)OCC)C=N2 SPSDEXPWUORORO-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- 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
-
- 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US93211286A | 1986-11-18 | 1986-11-18 | |
| US93211286 | 1986-11-18 | ||
| US11434087A | 1987-11-04 | 1987-11-04 | |
| US11434087 | 1987-11-04 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK604087D0 DK604087D0 (da) | 1987-11-17 |
| DK604087A DK604087A (da) | 1988-05-19 |
| DK170049B1 true DK170049B1 (da) | 1995-05-08 |
Family
ID=26812069
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK604087A DK170049B1 (da) | 1986-11-18 | 1987-11-17 | Phosphonomethoxyalkylenpurin- og pyrimidinderivater samt farmaceutiske præparater indeholdende sådanne derivater |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0269947B2 (es) |
| JP (1) | JP2593895B2 (es) |
| KR (1) | KR950009195B1 (es) |
| AU (1) | AU613592B2 (es) |
| CA (1) | CA1339780C (es) |
| DE (1) | DE3780581T3 (es) |
| DK (1) | DK170049B1 (es) |
| EG (1) | EG19346A (es) |
| ES (1) | ES2033774T5 (es) |
| GR (2) | GR3005256T3 (es) |
| IL (1) | IL84477A (es) |
| NZ (1) | NZ222553A (es) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CS264222B1 (en) * | 1986-07-18 | 1989-06-13 | Holy Antonin | N-phosphonylmethoxyalkylderivatives of bases of pytimidine and purine and method of use them |
| IL84477A (en) * | 1986-11-18 | 1995-12-08 | Bristol Myers Squibb Co | History of Phosphonomethoxyalkylene Purinopyrimidine and Pharmaceutical Preparations Containing Them |
| EP0338168A1 (en) * | 1988-04-19 | 1989-10-25 | Merrell Dow Pharmaceuticals Inc. | Phosphonoalkylpurine derivatives |
| US5266722A (en) * | 1988-11-09 | 1993-11-30 | W. R. Grace & Co.-Conn. | Polyether bis-phosphonic acid compounds |
| 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 |
| 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 |
| ATE124050T1 (de) * | 1990-04-20 | 1995-07-15 | Acad Of Science Czech Republic | Chirale 2-(phosphonomethoxy)propyl-guanine als antivirale agentien. |
| SK280313B6 (sk) * | 1990-04-24 | 1999-11-08 | �Stav Organick� Chemie A Biochemie Av �R | N-(3-fluór-2-fosfonylmetoxypropyl)deriváty purínov |
| ES2118069T3 (es) * | 1990-09-14 | 1998-09-16 | Acad Of Science Czech Republic | Profarmacos de fosfonatos. |
| US5208221A (en) * | 1990-11-29 | 1993-05-04 | Bristol-Myers Squibb Company | Antiviral (phosphonomethoxy) methoxy purine/pyrimidine derivatives |
| KR0184530B1 (ko) * | 1991-10-11 | 1999-05-15 | 카렐 마르티넥 | 항비루스 비고리 포스포노메톡시알킬치환, 알켄일 및 알킨일 퓨린 및 피리미딘 유도체 |
| 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 |
| US5656745A (en) * | 1993-09-17 | 1997-08-12 | Gilead Sciences, Inc. | Nucleotide analogs |
| US5798340A (en) * | 1993-09-17 | 1998-08-25 | Gilead Sciences, Inc. | Nucleotide analogs |
| KR100386685B1 (ko) * | 1993-09-17 | 2003-12-31 | 길리애드 사이언시즈, 인코포레이티드 | 뉴클레오타이드동족체류 |
| IT1270008B (it) * | 1994-09-23 | 1997-04-16 | Ist Superiore Sanita | Derivati purinici ed 8-azapurinici atti al trattamento terapeutico dell'aids |
| 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 |
| JP4033494B2 (ja) * | 1996-07-26 | 2008-01-16 | ギリヤド 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 |
| US5922695A (en) | 1996-07-26 | 1999-07-13 | Gilead Sciences, Inc. | Antiviral phosphonomethyoxy nucleotide analogs having increased oral bioavarilability |
| AU740264C (en) * | 1997-09-11 | 2002-06-06 | Commonwealth Scientific And Industrial Research Organisation | Antiviral agents |
| KR100891366B1 (ko) | 2001-06-29 | 2009-04-02 | 인스티튜트 오브 오르가닉 케미스트리 앤드 바이오케미스트리, 어케더미 오브 사이언시스 오브 더 체크 리퍼블릭 | 항 바이러스 활성을 갖는 6-'2-(포스포노메톡시)알콕시 피리미딘 유도체 |
| IL161901A0 (en) * | 2001-11-14 | 2005-11-20 | Biocryst Pharmaceuticals Inc A | Nucleosides, preparation thereof and use as inhibiDevice for the reading and the signalling of environmental parameters tors of rna viral polymerases |
| US7388002B2 (en) | 2001-11-14 | 2008-06-17 | Biocryst Pharmaceuticals, Inc. | Nucleosides, preparation thereof and use as inhibitors of RNA viral polymerases |
| CN105596356A (zh) | 2003-01-14 | 2016-05-25 | 吉里德科学公司 | 用于联合抗病毒治疗的组合物和方法 |
| US7371852B2 (en) | 2003-01-22 | 2008-05-13 | Serenex, Inc. | Alkyl-linked nucleotide compositions |
| DK1644389T3 (da) | 2003-06-16 | 2011-05-09 | Acad Of Science Czech Republic | Pyrinidinforbindelser med phosphonatgrupper som antivirale nukleotidanaloger |
| US7579332B2 (en) | 2003-07-30 | 2009-08-25 | Gilead Sciences, Inc. | Nucleobase phosphonate analogs for antiviral treatment |
| WO2005090370A1 (en) | 2004-02-05 | 2005-09-29 | The Regents Of The University Of California | Pharmacologically active agents containing esterified phosphonates and methods for use thereof |
| TWI471145B (zh) | 2005-06-13 | 2015-02-01 | Bristol Myers Squibb & Gilead Sciences Llc | 單一式藥學劑量型 |
| TWI375560B (en) | 2005-06-13 | 2012-11-01 | Gilead Sciences Inc | Composition comprising dry granulated emtricitabine and tenofovir df and method for making the same |
| 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 |
| FI2648701T3 (fi) | 2010-12-10 | 2023-06-12 | Sigmapharm Laboratories Llc | Hyvin stabiileja adefovirdipivoksiilin koostumuksia |
| DK2794624T3 (da) | 2011-12-22 | 2019-07-22 | Geron Corp | Guanin-analoger som telomerase-substrater og påvirkere af telomer-længde |
| CN103665043B (zh) | 2012-08-30 | 2017-11-10 | 江苏豪森药业集团有限公司 | 一种替诺福韦前药及其在医药上的应用 |
| EA036391B1 (ru) * | 2014-09-15 | 2020-11-05 | Дзе Риджентс Оф Дзе Юниверсити Оф Калифорния | Нуклеотидные аналоги |
Family Cites Families (5)
| 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 |
| CS263952B1 (en) * | 1985-04-25 | 1989-05-12 | Holy Antonin | Remedy with antiviral effect |
| 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 |
| IL84477A (en) * | 1986-11-18 | 1995-12-08 | Bristol Myers Squibb Co | History of Phosphonomethoxyalkylene Purinopyrimidine and Pharmaceutical Preparations Containing Them |
-
1987
- 1987-11-16 IL IL8447787A patent/IL84477A/en not_active IP Right Cessation
- 1987-11-16 NZ NZ222553A patent/NZ222553A/en unknown
- 1987-11-16 AU AU81250/87A patent/AU613592B2/en not_active Expired
- 1987-11-17 DE DE3780581T patent/DE3780581T3/de not_active Expired - Lifetime
- 1987-11-17 JP JP62290469A patent/JP2593895B2/ja not_active Expired - Lifetime
- 1987-11-17 EG EG65887A patent/EG19346A/xx active
- 1987-11-17 CA CA000551979A patent/CA1339780C/en not_active Expired - Lifetime
- 1987-11-17 EP EP87116996A patent/EP0269947B2/en not_active Expired - Lifetime
- 1987-11-17 DK DK604087A patent/DK170049B1/da not_active IP Right Cessation
- 1987-11-17 ES ES87116996T patent/ES2033774T5/es not_active Expired - Lifetime
- 1987-11-18 KR KR1019870012967A patent/KR950009195B1/ko not_active IP Right Cessation
-
1992
- 1992-07-23 GR GR920401473T patent/GR3005256T3/el unknown
-
1996
- 1996-10-17 GR GR960400474T patent/GR3021389T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2593895B2 (ja) | 1997-03-26 |
| ES2033774T3 (es) | 1993-04-01 |
| JPS63170388A (ja) | 1988-07-14 |
| GR3021389T3 (en) | 1997-01-31 |
| DK604087D0 (da) | 1987-11-17 |
| KR880006256A (ko) | 1988-07-22 |
| KR950009195B1 (ko) | 1995-08-16 |
| EP0269947B1 (en) | 1992-07-22 |
| CA1339780C (en) | 1998-03-24 |
| ES2033774T5 (es) | 1997-03-16 |
| DE3780581D1 (de) | 1992-08-27 |
| IL84477A (en) | 1995-12-08 |
| GR3005256T3 (en) | 1993-05-24 |
| AU613592B2 (en) | 1991-08-08 |
| AU8125087A (en) | 1988-05-19 |
| DE3780581T3 (de) | 1997-06-05 |
| EG19346A (en) | 1995-01-31 |
| EP0269947B2 (en) | 1996-10-16 |
| DE3780581T2 (de) | 1992-12-17 |
| EP0269947A1 (en) | 1988-06-08 |
| DK604087A (da) | 1988-05-19 |
| NZ222553A (en) | 1991-07-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Patent granted (law 1993) | ||
| PUP | Patent expired |