JP2008523082A - 抗菌活性および抗癌活性を有するヌクレオチド - Google Patents
抗菌活性および抗癌活性を有するヌクレオチド Download PDFInfo
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- JP2008523082A JP2008523082A JP2007545627A JP2007545627A JP2008523082A JP 2008523082 A JP2008523082 A JP 2008523082A JP 2007545627 A JP2007545627 A JP 2007545627A JP 2007545627 A JP2007545627 A JP 2007545627A JP 2008523082 A JP2008523082 A JP 2008523082A
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- alkyl
- cycloalkyl
- hydrogen
- hydroxy
- aryl
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- 0 *C(*C(COP(*)(*)=O)C1(*)I*)C1(*)I* Chemical compound *C(*C(COP(*)(*)=O)C1(*)I*)C1(*)I* 0.000 description 4
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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
- C07H19/23—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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- 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
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- 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
- A61P31/14—Antivirals for RNA viruses
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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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
- 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
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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
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
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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
- C07H19/052—Imidazole 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
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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
- C07H19/16—Purine radicals
- C07H19/167—Purine radicals with ribosyl as the saccharide radical
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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
- C07H19/16—Purine radicals
- C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K2/00—Peptides of undefined number of amino acids; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K4/00—Peptides having up to 20 amino acids in an undefined or only partially defined sequence; Derivatives thereof
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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
- C07H19/16—Purine 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
- C07H19/16—Purine radicals
- C07H19/19—Purine radicals with arabinosyl as the saccharide radical
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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
- C07H19/16—Purine radicals
- C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
- C07H19/207—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids the phosphoric or polyphosphoric acids being esterified by a further hydroxylic compound, e.g. flavine adenine dinucleotide or nicotinamide-adenine dinucleotide
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- 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)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Virology (AREA)
- Biophysics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Gastroenterology & Hepatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63467704P | 2004-12-09 | 2004-12-09 | |
| PCT/US2005/044442 WO2006063149A1 (en) | 2004-12-09 | 2005-12-08 | Nucleosides with antiviral and anticancer activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008523082A true JP2008523082A (ja) | 2008-07-03 |
| JP2008523082A5 JP2008523082A5 (enExample) | 2009-01-22 |
Family
ID=36578243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007545627A Withdrawn JP2008523082A (ja) | 2004-12-09 | 2005-12-08 | 抗菌活性および抗癌活性を有するヌクレオチド |
Country Status (5)
| Country | Link |
|---|---|
| US (7) | US8399428B2 (enExample) |
| EP (1) | EP1827460A4 (enExample) |
| JP (1) | JP2008523082A (enExample) |
| CA (1) | CA2589935A1 (enExample) |
| WO (1) | WO2006063149A1 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012513479A (ja) * | 2008-12-23 | 2012-06-14 | ギリアド ファーマセット エルエルシー | プリンヌクレオシドの合成 |
| US8969357B2 (en) | 2011-10-21 | 2015-03-03 | Abbvie Inc. | Methods for treating HCV |
| US9452194B2 (en) | 2011-10-21 | 2016-09-27 | Abbvie Inc. | Methods for treating HCV |
| JP2017535587A (ja) * | 2014-11-28 | 2017-11-30 | ヌカナ バイオメド リミテッド | 抗がん性化合物としての新規な2’および/または5’アミノ酸エステルホスホロアミダート3’−デオキシアデノシン誘導体 |
Families Citing this family (67)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PY0111577A (es) | 2000-05-23 | 2017-01-02 | Idenix Cayman Ltd | Métodos y composiciones para el tratamiento del virus de la hepatitis c |
| CA2589935A1 (en) | 2004-12-09 | 2006-06-15 | Regents Of The University Of Minnesota | Nucleosides with antiviral and anticancer activity |
| US7879815B2 (en) | 2006-02-14 | 2011-02-01 | Merck Sharp & Dohme Corp. | Nucleoside aryl phosphoramidates for the treatment of RNA-dependent RNA viral infection |
| GB0623493D0 (en) | 2006-11-24 | 2007-01-03 | Univ Cardiff | Chemical compounds |
| US8148349B2 (en) | 2006-12-20 | 2012-04-03 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A. | Nucleoside cyclic phosphoramidates for the treatment of RNA-dependent RNA viral infection |
| US7951789B2 (en) | 2006-12-28 | 2011-05-31 | Idenix Pharmaceuticals, Inc. | Compounds and pharmaceutical compositions for the treatment of viral infections |
| US8071568B2 (en) | 2007-01-05 | 2011-12-06 | Merck Sharp & Dohme Corp. | Nucleoside aryl phosphoramidates for the treatment of RNA-dependent RNA viral infection |
| EP2144921A2 (en) * | 2007-02-27 | 2010-01-20 | K.U. Leuven Research and Development | Phosphate modified nucleosides useful as substrates for polymerases and as antiviral agents |
| US7964580B2 (en) | 2007-03-30 | 2011-06-21 | Pharmasset, Inc. | Nucleoside phosphoramidate prodrugs |
| US8173621B2 (en) | 2008-06-11 | 2012-05-08 | Gilead Pharmasset Llc | Nucleoside cyclicphosphates |
| JP6104504B2 (ja) | 2008-12-23 | 2017-03-29 | ギリアド ファーマセット エルエルシー | ヌクレオシド類似体 |
| TW201026715A (en) | 2008-12-23 | 2010-07-16 | Pharmasset Inc | Nucleoside phosphoramidates |
| US8618076B2 (en) | 2009-05-20 | 2013-12-31 | Gilead Pharmasset Llc | Nucleoside phosphoramidates |
| TWI583692B (zh) | 2009-05-20 | 2017-05-21 | 基利法瑪席特有限責任公司 | 核苷磷醯胺 |
| PL3290428T3 (pl) | 2010-03-31 | 2022-02-07 | Gilead Pharmasset Llc | Tabletka zawierająca krystaliczny (S)-2-(((S)-(((2R,3R,4R,5R)-5-(2,4-diokso-3,4-dihydropirymidyn-1(2H)-ylo)-4-fluoro-3-hydroksy-4-metylotetrahydrofuran-2-ylo)metoksy)(fenoksy)fosforylo)amino)propanian izopropylu |
| CL2011000716A1 (es) | 2010-03-31 | 2012-04-20 | Gilead Pharmasset Llc | Formas cristalinas 1 6 de (s)-isopropil-2-(((s)-(((2r.3r.4r.5r)-5-(2,4-dioxo-3,4-dihidropirimidin-1(2h)-il)-4-fluoro-3-hidroxi-4-metil tetrahidrofuran-2-il)metoxi)(fenoxi)fosforil)amino)propanoato; composicion y combinacion farmaceutica; y su uso para tratar una infeccion por el virus de la hepatitis c. |
| WO2012075140A1 (en) | 2010-11-30 | 2012-06-07 | Pharmasset, Inc. | Compounds |
| CN103403014B (zh) | 2011-01-03 | 2016-07-06 | 河南美泰宝生物制药有限公司 | O-(经取代的苯甲基)氨基磷酸酯化合物及其治疗用途 |
| US9156874B2 (en) | 2011-01-03 | 2015-10-13 | Nanjing Molecular Research, Inc. | Double-liver-targeting phosphoramidate and phosphonoamidate prodrugs |
| DK3447061T3 (da) | 2011-03-01 | 2022-01-03 | NuCana plc | Farmaceutisk formulering omfattende et phosphoramidatderivat af 5-fluor-2'-deoxyuridin til anvendelse i cancerbehandling |
| CN103842369A (zh) | 2011-03-31 | 2014-06-04 | 埃迪尼克斯医药公司 | 用于治疗病毒感染的化合物和药物组合物 |
| WO2013013009A2 (en) * | 2011-07-19 | 2013-01-24 | Nanjing Molecular Research, Inc. | 2',3'-DIDEOXY-2'-α-FLUORO-2'-β-C-METHYLNUCLEOSIDES AND PRODRUGS THEREOF |
| AR088441A1 (es) | 2011-09-12 | 2014-06-11 | Idenix Pharmaceuticals Inc | Compuestos de carboniloximetilfosforamidato sustituido y composiciones farmaceuticas para el tratamiento de infecciones virales |
| CN104023726A (zh) | 2011-10-21 | 2014-09-03 | 艾伯维公司 | 用于治疗hcv的一种或多种daa的联合治疗(例如,与abt-072或abt-333) |
| US8492386B2 (en) | 2011-10-21 | 2013-07-23 | Abbvie Inc. | Methods for treating HCV |
| US8889159B2 (en) | 2011-11-29 | 2014-11-18 | Gilead Pharmasset Llc | Compositions and methods for treating hepatitis C virus |
| SG10201610936RA (en) | 2011-12-22 | 2017-02-27 | Alios Biopharma Inc | Substituted nucleosides, nucleotides and analogs thereof |
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| WO2014052638A1 (en) | 2012-09-27 | 2014-04-03 | Idenix Pharmaceuticals, Inc. | Esters and malonates of sate prodrugs |
| SG11201502750UA (en) | 2012-10-08 | 2015-06-29 | Idenix Pharmaceuticals Inc | 2'-chloro nucleoside analogs for hcv infection |
| EP2909222B1 (en) | 2012-10-22 | 2021-05-26 | Idenix Pharmaceuticals LLC | 2',4'-bridged nucleosides for hcv infection |
| EP2935304A1 (en) | 2012-12-19 | 2015-10-28 | IDENIX Pharmaceuticals, Inc. | 4'-fluoro nucleosides for the treatment of hcv |
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| US9309275B2 (en) | 2013-03-04 | 2016-04-12 | Idenix Pharmaceuticals Llc | 3′-deoxy nucleosides for the treatment of HCV |
| WO2014137930A1 (en) | 2013-03-04 | 2014-09-12 | Idenix Pharmaceuticals, Inc. | Thiophosphate nucleosides for the treatment of hcv |
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| US11439656B2 (en) * | 2018-08-30 | 2022-09-13 | Regents Of The University Of Minnesota | Pharmaceutical compounds and uses thereof |
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| BR112023026356A2 (pt) | 2021-06-17 | 2024-03-05 | Atea Pharmaceuticals Inc | Método para tratar vírus da hepatite c ou uma condição resultante de uma infecção por hepatite c, combinação, uso da combinação, composição farmacêutica, e, kit para o tratamento de vírus da hepatite c |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GB8827337D0 (en) | 1988-11-23 | 1988-12-29 | Medical Res Council | Nucleoside analogues |
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- 2005-12-08 CA CA002589935A patent/CA2589935A1/en not_active Abandoned
- 2005-12-08 WO PCT/US2005/044442 patent/WO2006063149A1/en not_active Ceased
- 2005-12-08 JP JP2007545627A patent/JP2008523082A/ja not_active Withdrawn
- 2005-12-08 US US11/721,325 patent/US8399428B2/en not_active Expired - Fee Related
- 2005-12-08 EP EP05853381A patent/EP1827460A4/en not_active Withdrawn
-
2013
- 2013-01-29 US US13/753,252 patent/US8765935B2/en not_active Expired - Lifetime
-
2014
- 2014-03-28 US US14/229,292 patent/US8815830B2/en not_active Expired - Lifetime
- 2014-07-21 US US14/336,225 patent/US20150025220A1/en not_active Abandoned
-
2016
- 2016-02-16 US US15/044,853 patent/US20160159845A1/en not_active Abandoned
-
2017
- 2017-10-18 US US15/787,140 patent/US20180258131A1/en not_active Abandoned
-
2019
- 2019-02-27 US US16/287,387 patent/US20200095273A1/en not_active Abandoned
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012513479A (ja) * | 2008-12-23 | 2012-06-14 | ギリアド ファーマセット エルエルシー | プリンヌクレオシドの合成 |
| JP2013082728A (ja) * | 2008-12-23 | 2013-05-09 | Gilead Pharmasset Llc | プリンヌクレオシドの合成 |
| US8969357B2 (en) | 2011-10-21 | 2015-03-03 | Abbvie Inc. | Methods for treating HCV |
| US9452194B2 (en) | 2011-10-21 | 2016-09-27 | Abbvie Inc. | Methods for treating HCV |
| JP2017535587A (ja) * | 2014-11-28 | 2017-11-30 | ヌカナ バイオメド リミテッド | 抗がん性化合物としての新規な2’および/または5’アミノ酸エステルホスホロアミダート3’−デオキシアデノシン誘導体 |
| JP2020075928A (ja) * | 2014-11-28 | 2020-05-21 | ヌカナ ピーエルシー | 抗がん性化合物としての新規な2’および/または5’アミノ酸エステルホスホロアミダート3’−デオキシアデノシン誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006063149A1 (en) | 2006-06-15 |
| US20150025220A1 (en) | 2015-01-22 |
| US8399428B2 (en) | 2013-03-19 |
| US20090306007A1 (en) | 2009-12-10 |
| US20200095273A1 (en) | 2020-03-26 |
| US8815830B2 (en) | 2014-08-26 |
| US20130203978A1 (en) | 2013-08-08 |
| US20160159845A1 (en) | 2016-06-09 |
| EP1827460A1 (en) | 2007-09-05 |
| CA2589935A1 (en) | 2006-06-15 |
| US20140213543A1 (en) | 2014-07-31 |
| EP1827460A4 (en) | 2012-03-14 |
| US20180258131A1 (en) | 2018-09-13 |
| US8765935B2 (en) | 2014-07-01 |
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