AU781323B2 - Anti-viral pyrimidine nucleoside analogues - Google Patents
Anti-viral pyrimidine nucleoside analogues Download PDFInfo
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- AU781323B2 AU781323B2 AU95191/01A AU9519101A AU781323B2 AU 781323 B2 AU781323 B2 AU 781323B2 AU 95191/01 A AU95191/01 A AU 95191/01A AU 9519101 A AU9519101 A AU 9519101A AU 781323 B2 AU781323 B2 AU 781323B2
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- alkyl
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- 230000000840 anti-viral effect Effects 0.000 title abstract description 8
- 229940127073 nucleoside analogue Drugs 0.000 title description 4
- 239000002718 pyrimidine nucleoside Substances 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 73
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 125000003118 aryl group Chemical group 0.000 claims abstract description 65
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 22
- 150000002367 halogens Chemical class 0.000 claims abstract description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 18
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 9
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 9
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 9
- 150000001356 alkyl thiols Chemical class 0.000 claims abstract description 8
- -1 arythiol Chemical group 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
- 229910052770 Uranium Inorganic materials 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims abstract description 3
- 150000003573 thiols Chemical class 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract 3
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 21
- 238000011282 treatment Methods 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 208000036142 Viral infection Diseases 0.000 claims description 9
- 238000011321 prophylaxis Methods 0.000 claims description 9
- 230000009385 viral infection Effects 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
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- 239000000460 chlorine Substances 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 229940002612 prodrug Drugs 0.000 claims description 6
- 239000000651 prodrug Substances 0.000 claims description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims description 5
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
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Classifications
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/498—Pyrazines or piperazines ortho- and peri-condensed with carbocyclic ring systems, e.g. quinoxaline, phenazine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- 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
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- 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
- C07D491/02—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 two hetero rings
- C07D491/04—Ortho-condensed systems
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- 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
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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
-
- 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
- C07H19/14—Pyrrolo-pyrimidine radicals
-
- 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
- C07H19/23—Heterocyclic radicals containing two or more heterocyclic rings condensed among themselves or condensed with a common carbocyclic ring system, not provided for in groups C07H19/14 - C07H19/22
-
- 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
- C07H19/24—Heterocyclic radicals containing oxygen or sulfur as ring hetero atom
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)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| GB0009486 | 2000-04-17 | ||
| PCT/GB2001/001694 WO2001083501A1 (en) | 2000-04-17 | 2001-04-12 | Anti-viral pyrimidine nucleoside analogues |
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| US7462605B2 (en) | 1998-01-23 | 2008-12-09 | Celmed Oncology (Usa), Inc. | Phosphoramidate compounds and methods of use |
| US6683061B1 (en) | 1999-07-22 | 2004-01-27 | Newbiotics, Inc. | Enzyme catalyzed therapeutic activation |
| KR20020059341A (ko) | 1999-07-22 | 2002-07-12 | 뉴바이오틱스 인코퍼레이티드 | 치료법-내성 종양의 치료 방법 |
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| MY164523A (en) | 2000-05-23 | 2017-12-29 | Univ Degli Studi Cagliari | Methods and compositions for treating hepatitis c virus |
| ES2624353T3 (es) | 2002-11-15 | 2017-07-13 | Idenix Pharmaceuticals Llc | 2'-Metil nucleósidos en combinación con interferón y mutación de Flaviviridae |
| GB0609178D0 (en) | 2006-05-09 | 2006-06-21 | Univ Cardiff | Novel compounds |
| JP5539735B2 (ja) * | 2007-02-28 | 2014-07-02 | ザ ガバナーズ オブ ザ ユニバーシティ オブ アルバータ | ウイルス感染の予防又は治療のための化合物とその使用方法 |
| GB2452556A (en) * | 2007-09-07 | 2009-03-11 | Univ Leuven Kath | Nucleoside analogues esterified at 3 and/or 5 positions by neutral non-polar amino acid, or oligopeptide thereof, for combating Varicella Zoster virus |
| GB201016855D0 (en) * | 2010-10-06 | 2010-11-17 | Nucana Biomed Ltd | Chemical compounds |
| CA2813993A1 (en) | 2010-10-09 | 2012-04-12 | Synergy Pharmaceuticals, Inc. | Method of preparation of antiviral compounds and useful intermediates thereof |
| CN105037468A (zh) * | 2010-10-09 | 2015-11-11 | 英希比泰克斯公司 | 制备抗病毒组合物的方法及其中间体的应用 |
| US9243025B2 (en) | 2011-03-31 | 2016-01-26 | Idenix Pharmaceuticals, Llc | Compounds and pharmaceutical compositions for the treatment of viral infections |
| GB201111779D0 (en) | 2011-07-08 | 2011-08-24 | Univ Cardiff | Chemical compounds |
| WO2013039920A1 (en) | 2011-09-12 | 2013-03-21 | Idenix Pharmaceuticals, Inc. | Substituted carbonyloxymethylphosphoramidate compounds and pharmaceutical compositions for the treatment of viral infections |
| WO2013056046A1 (en) | 2011-10-14 | 2013-04-18 | Idenix Pharmaceuticals, Inc. | Substituted 3',5'-cyclic phosphates of purine nucleotide compounds and pharmaceutical compositions for the treatment of viral infections |
| EP2852604B1 (en) | 2012-05-22 | 2017-04-12 | Idenix Pharmaceuticals LLC | 3',5'-cyclic phosphoramidate prodrugs for hcv infection |
| EP2852605B1 (en) | 2012-05-22 | 2018-01-31 | Idenix Pharmaceuticals LLC | 3',5'-cyclic phosphate prodrugs for hcv infection |
| BR112014029115A8 (pt) | 2012-05-22 | 2018-04-03 | Idenix Pharmaceuticals Inc | Composto, composição farmacêutica, e, uso de um composto ou composição |
| MX2014014323A (es) | 2012-05-25 | 2015-02-12 | Janssen R & D Ireland | Nucleosidos de espirooxetano de uracilo. |
| WO2014052638A1 (en) | 2012-09-27 | 2014-04-03 | Idenix Pharmaceuticals, Inc. | Esters and malonates of sate prodrugs |
| CN104936970A (zh) | 2012-10-08 | 2015-09-23 | 埃迪尼克斯医药公司 | 用于hcv感染的2′-氯核苷类似物 |
| US10723754B2 (en) | 2012-10-22 | 2020-07-28 | Idenix Pharmaceuticals Llc | 2′,4′-bridged nucleosides for HCV infection |
| WO2014099941A1 (en) | 2012-12-19 | 2014-06-26 | Idenix Pharmaceuticals, Inc. | 4'-fluoro nucleosides for the treatment of hcv |
| WO2014137926A1 (en) | 2013-03-04 | 2014-09-12 | Idenix Pharmaceuticals, Inc. | 3'-deoxy nucleosides for the treatment of hcv |
| US9339541B2 (en) | 2013-03-04 | 2016-05-17 | Merck Sharp & Dohme Corp. | Thiophosphate nucleosides for the treatment of HCV |
| WO2014160484A1 (en) | 2013-03-13 | 2014-10-02 | Idenix Pharmaceuticals, Inc. | Amino acid phosphoramidate pronucleotides of 2'-cyano, azido and amino nucleosides for the treatment of hcv |
| WO2014165542A1 (en) | 2013-04-01 | 2014-10-09 | Idenix Pharmaceuticals, Inc. | 2',4'-fluoro nucleosides for the treatment of hcv |
| EP3004130B1 (en) | 2013-06-05 | 2019-08-07 | Idenix Pharmaceuticals LLC. | 1',4'-thio nucleosides for the treatment of hcv |
| EP3027636B1 (en) | 2013-08-01 | 2022-01-05 | Idenix Pharmaceuticals LLC | D-amino acid phosphoramidate pronucleotides of halogeno pyrimidine compounds for liver disease |
| EP3131914B1 (en) | 2014-04-16 | 2023-05-10 | Idenix Pharmaceuticals LLC | 3'-substituted methyl or alkynyl nucleosides for the treatment of hcv |
| WO2018035429A1 (en) | 2016-08-18 | 2018-02-22 | Wisconsin Alumni Research Foundation | Peptides that inhibit syndecan-1 activation of vla-4 and igf-1r |
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| EP0346108A3 (en) | 1988-06-09 | 1991-04-24 | The Wellcome Foundation Limited | Anti-infective nucleosides |
| YU43193A (sh) * | 1992-06-22 | 1997-01-08 | Eli Lilly And Company | 2'-deoksi-2',2'-difluoro(4-supstituisani)pirimidinski nukleozidi antivirusnog i antikancerogenog dejstva i međuproizvodi |
| GB9505025D0 (en) | 1995-03-13 | 1995-05-03 | Medical Res Council | Chemical compounds |
| US6022876A (en) * | 1996-11-15 | 2000-02-08 | Yale University | L-β-dioxolane uridine analogs and methods for treating and preventing Epstein-Barr virus infections |
| GB9708611D0 (en) | 1997-04-28 | 1997-06-18 | Univ Cardiff | Chemical compounds |
| GB9716231D0 (en) * | 1997-07-31 | 1997-10-08 | Amersham Int Ltd | Base analogues |
| CN1390227A (zh) | 1999-07-22 | 2003-01-08 | 新生物生物公司 | 酶催化的治疗活化 |
| KR20020059341A (ko) * | 1999-07-22 | 2002-07-12 | 뉴바이오틱스 인코퍼레이티드 | 치료법-내성 종양의 치료 방법 |
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| GB0009486D0 (en) * | 2000-04-17 | 2000-06-07 | Univ Cardiff | Chemical compounds |
| GB0011203D0 (en) * | 2000-05-09 | 2000-06-28 | Univ Cardiff | Chemical compounds |
| US20080070852A1 (en) * | 2004-06-07 | 2008-03-20 | Averett Devron R | 3-Beta-D-Ribofuranosylthiazolo[ 4,5-D] Pyridimine Nucleosides and Uses Thereof |
| GB0609178D0 (en) * | 2006-05-09 | 2006-06-21 | Univ Cardiff | Novel compounds |
| GB2452556A (en) * | 2007-09-07 | 2009-03-11 | Univ Leuven Kath | Nucleoside analogues esterified at 3 and/or 5 positions by neutral non-polar amino acid, or oligopeptide thereof, for combating Varicella Zoster virus |
| GB201111779D0 (en) * | 2011-07-08 | 2011-08-24 | Univ Cardiff | Chemical compounds |
-
2000
- 2000-04-17 GB GBGB0009486.2A patent/GB0009486D0/en not_active Ceased
-
2001
- 2001-04-12 ES ES01973778T patent/ES2215931T3/es not_active Expired - Lifetime
- 2001-04-12 CA CA002403835A patent/CA2403835C/en not_active Expired - Fee Related
- 2001-04-12 EP EP01973778A patent/EP1274713B1/en not_active Expired - Lifetime
- 2001-04-12 DK DK01973778T patent/DK1274713T3/da active
- 2001-04-12 WO PCT/GB2001/001694 patent/WO2001083501A1/en not_active Ceased
- 2001-04-12 PT PT01973778T patent/PT1274713E/pt unknown
- 2001-04-12 DE DE60102293T patent/DE60102293T2/de not_active Expired - Lifetime
- 2001-04-12 AT AT01973778T patent/ATE261451T1/de active
- 2001-04-12 NZ NZ521828A patent/NZ521828A/en not_active IP Right Cessation
- 2001-04-12 AU AU95191/01A patent/AU781323B2/en not_active Ceased
- 2001-04-12 US US10/257,855 patent/US7820631B2/en not_active Expired - Fee Related
- 2001-04-12 TR TR2004/00785T patent/TR200400785T4/xx unknown
- 2001-04-12 JP JP2001580925A patent/JP4959900B2/ja not_active Expired - Fee Related
-
2010
- 2010-09-24 US US12/889,980 patent/US8551965B2/en not_active Expired - Fee Related
-
2013
- 2013-09-09 US US14/021,587 patent/US9351970B2/en not_active Expired - Fee Related
-
2016
- 2016-04-29 US US15/141,992 patent/US20160244476A1/en not_active Abandoned
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| CHEM. ABS., ABSTRACT NO. 118:124938 * |
| CHEM. ABS., ABSTRACT NO. 124:87652 * |
| J. ORG. CHEM. (1993), 58, 6614-6619 * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE60102293T2 (de) | 2005-02-17 |
| US9351970B2 (en) | 2016-05-31 |
| ES2215931T3 (es) | 2004-10-16 |
| TR200400785T4 (tr) | 2004-07-21 |
| US20160244476A1 (en) | 2016-08-25 |
| DE60102293D1 (de) | 2004-04-15 |
| JP4959900B2 (ja) | 2012-06-27 |
| EP1274713B1 (en) | 2004-03-10 |
| EP1274713A1 (en) | 2003-01-15 |
| AU9519101A (en) | 2001-11-12 |
| WO2001083501A1 (en) | 2001-11-08 |
| PT1274713E (pt) | 2004-08-31 |
| CA2403835A1 (en) | 2001-11-08 |
| NZ521828A (en) | 2005-06-24 |
| JP2004506606A (ja) | 2004-03-04 |
| US20140011764A1 (en) | 2014-01-09 |
| US20110015147A1 (en) | 2011-01-20 |
| US8551965B2 (en) | 2013-10-08 |
| US20030148967A1 (en) | 2003-08-07 |
| DK1274713T3 (da) | 2004-08-02 |
| US7820631B2 (en) | 2010-10-26 |
| ATE261451T1 (de) | 2004-03-15 |
| GB0009486D0 (en) | 2000-06-07 |
| CA2403835C (en) | 2010-01-12 |
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