KR101235548B1 - 2'-데옥시-2'-플루오로-2'-C-메틸-β-D-리보퓨라노실 뉴클레오사이드의 제조 방법 - Google Patents
2'-데옥시-2'-플루오로-2'-C-메틸-β-D-리보퓨라노실 뉴클레오사이드의 제조 방법 Download PDFInfo
- Publication number
- KR101235548B1 KR101235548B1 KR1020117006244A KR20117006244A KR101235548B1 KR 101235548 B1 KR101235548 B1 KR 101235548B1 KR 1020117006244 A KR1020117006244 A KR 1020117006244A KR 20117006244 A KR20117006244 A KR 20117006244A KR 101235548 B1 KR101235548 B1 KR 101235548B1
- Authority
- KR
- South Korea
- Prior art keywords
- methyl
- fluoro
- alkyl
- deoxy
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
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
-
- 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
- C07H19/173—Purine radicals with 2-deoxyribosyl as the saccharide radical
-
- 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
-
- 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
- C07H19/073—Pyrimidine radicals with 2-deoxyribosyl as the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
- C07H5/06—Aminosugars
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Virology (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58986604P | 2004-07-21 | 2004-07-21 | |
| US60/589,866 | 2004-07-21 | ||
| US60823004P | 2004-09-09 | 2004-09-09 | |
| US60/608,320 | 2004-09-09 | ||
| PCT/US2005/025916 WO2006012440A2 (en) | 2004-07-21 | 2005-07-21 | Preparation of alkyl-substituted 2-deoxy-2-fluoro-d-ribofuranosyl pyrimidines and purines and their derivatives |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020077003980A Division KR101236669B1 (ko) | 2004-07-21 | 2005-07-21 | 알킬-치환된 2-데옥시-2-플루오로-d-리보퓨라노실피리미딘 및 퓨린 및 그 유도체의 제조 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20110034699A KR20110034699A (ko) | 2011-04-05 |
| KR101235548B1 true KR101235548B1 (ko) | 2013-02-21 |
Family
ID=35786706
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020077003980A Expired - Lifetime KR101236669B1 (ko) | 2004-07-21 | 2005-07-21 | 알킬-치환된 2-데옥시-2-플루오로-d-리보퓨라노실피리미딘 및 퓨린 및 그 유도체의 제조 |
| KR1020117006244A Expired - Lifetime KR101235548B1 (ko) | 2004-07-21 | 2005-07-21 | 2'-데옥시-2'-플루오로-2'-C-메틸-β-D-리보퓨라노실 뉴클레오사이드의 제조 방법 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020077003980A Expired - Lifetime KR101236669B1 (ko) | 2004-07-21 | 2005-07-21 | 알킬-치환된 2-데옥시-2-플루오로-d-리보퓨라노실피리미딘 및 퓨린 및 그 유도체의 제조 |
Country Status (16)
| Country | Link |
|---|---|
| EP (2) | EP1773856B1 (enExample) |
| JP (2) | JP5078612B2 (enExample) |
| KR (2) | KR101236669B1 (enExample) |
| CN (1) | CN102199181B (enExample) |
| AT (1) | ATE543789T1 (enExample) |
| AU (2) | AU2005267051B2 (enExample) |
| CA (2) | CA2735079C (enExample) |
| DK (1) | DK1773856T3 (enExample) |
| ES (1) | ES2386005T3 (enExample) |
| IL (2) | IL180832A (enExample) |
| MX (1) | MX2007000803A (enExample) |
| NZ (1) | NZ552927A (enExample) |
| PL (1) | PL1773856T3 (enExample) |
| PT (1) | PT1773856E (enExample) |
| RU (1) | RU2407747C2 (enExample) |
| WO (1) | WO2006012440A2 (enExample) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY164523A (en) | 2000-05-23 | 2017-12-29 | Univ Degli Studi Cagliari | Methods and compositions for treating hepatitis c virus |
| CZ301182B6 (cs) | 2000-05-26 | 2009-12-02 | Idenix (Cayman) Limited | Použití nukleosidových derivátu pro výrobu farmaceutických prostredku pro lécení infekcí vyvolaných flaviviry a pestiviry |
| NZ537662A (en) | 2002-06-28 | 2007-10-26 | Idenix Cayman Ltd | 2'-C-methyl-3'-O-L-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections |
| US7608600B2 (en) | 2002-06-28 | 2009-10-27 | Idenix Pharmaceuticals, Inc. | Modified 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections |
| MXPA04012802A (es) | 2002-06-28 | 2005-04-19 | Idenix Cayman Ltd | Ester 2'-c-metil-3'-o-l-valina de ribofuranosil-citidina para el tratamiento de infecciones por flaviviridae. |
| WO2004046331A2 (en) | 2002-11-15 | 2004-06-03 | Idenix (Cayman) Limited | 2’-branched nucleosides and flaviviridae mutation |
| US7598373B2 (en) | 2002-12-12 | 2009-10-06 | Idenix Pharmaceuticals, Inc. | Process for the production of 2-C-methyl-D-ribonolactone |
| EP2345659A1 (en) | 2003-05-30 | 2011-07-20 | Pharmasset, Inc. | Modified fluorinated nucleoside analogues |
| CN101023094B (zh) | 2004-07-21 | 2011-05-18 | 法莫赛特股份有限公司 | 烷基取代的2-脱氧-2-氟代-d-呋喃核糖基嘧啶和嘌呤及其衍生物的制备 |
| ES2769377T3 (es) * | 2004-09-14 | 2020-06-25 | Gilead Pharmasset Llc | Intermedios de D-ribonolactona con sustitución de 2-fluoro-2-alquilo |
| CN101600725B (zh) * | 2006-10-10 | 2014-11-26 | 吉利德制药有限责任公司 | 制备呋喃核糖基嘧啶核苷 |
| MX2009006156A (es) * | 2006-12-18 | 2009-06-19 | Hoffmann La Roche | Proceso para preparar 3,5-di-omicron-acil-2-fluoro-2-c-metil-d-rib ono-gamma-lactona. |
| US7951789B2 (en) | 2006-12-28 | 2011-05-31 | Idenix Pharmaceuticals, Inc. | Compounds and pharmaceutical compositions for the treatment of viral infections |
| WO2008090046A1 (en) * | 2007-01-23 | 2008-07-31 | F. Hoffmann-La Roche Ag | Alternate process for preparing 3,5-di-omicron-acyl-2-fluoro-2-c-methyl-d-ribono-gamma-lactone |
| US7964580B2 (en) | 2007-03-30 | 2011-06-21 | Pharmasset, Inc. | Nucleoside phosphoramidate prodrugs |
| AU2009329917B2 (en) | 2008-12-23 | 2016-03-31 | Gilead Pharmasset Llc | Nucleoside analogs |
| CN102695513A (zh) | 2008-12-23 | 2012-09-26 | 吉利德制药有限责任公司 | 核苷氨基磷酸酯 |
| BRPI0923815A2 (pt) * | 2008-12-23 | 2015-07-14 | Pharmasset Inc | Síntese de nucleosídeos de purina |
| 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 |
| US8618076B2 (en) | 2009-05-20 | 2013-12-31 | Gilead Pharmasset Llc | Nucleoside phosphoramidates |
| SMT201700412T1 (it) | 2010-03-31 | 2017-11-15 | Gilead Pharmasset Llc | Procedimento per la cristallizzazione di (s)-isopropil 2-(((s)-(perfluorofenossi)(fenossi)fosforil)ammino)propanoato |
| JP5716500B2 (ja) | 2010-06-03 | 2015-05-13 | セントラル硝子株式会社 | (2R)−2−フルオロ−2−C−メチル−D−リボノ−γ−ラクトン類前駆体の製造方法 |
| PT3042910T (pt) | 2010-11-30 | 2019-04-16 | Gilead Pharmasset Llc | 2'-espiro-nucleósidos para utilização na terapia da hepatite c |
| US9243025B2 (en) | 2011-03-31 | 2016-01-26 | Idenix Pharmaceuticals, Llc | Compounds and pharmaceutical compositions for the treatment of viral infections |
| US8877733B2 (en) | 2011-04-13 | 2014-11-04 | Gilead Sciences, Inc. | 1′-substituted pyrimidine N-nucleoside analogs for antiviral treatment |
| EP2709613B2 (en) | 2011-09-16 | 2020-08-12 | Gilead Pharmasset LLC | Methods for treating hcv |
| US8889159B2 (en) | 2011-11-29 | 2014-11-18 | Gilead Pharmasset Llc | Compositions and methods for treating hepatitis C virus |
| PL2950786T3 (pl) | 2013-01-31 | 2020-05-18 | Gilead Pharmasset Llc | Formulacja skojarzona dwóch związków przeciwwirusowych |
| WO2014132975A1 (ja) * | 2013-02-28 | 2014-09-04 | セントラル硝子株式会社 | (2R)-2-フルオロ-2-C-メチル-D-リボノ-γ-ラクトンの製造方法 |
| JP6476591B2 (ja) * | 2013-06-05 | 2019-03-06 | セントラル硝子株式会社 | (2R)−2−フルオロ−2−C−メチル−D−リボノ−γ−ラクトン類の製造方法 |
| PL3038601T3 (pl) | 2013-08-27 | 2020-08-24 | Gilead Pharmasset Llc | Formulacja złożona dwóch związków przeciwwirusowych |
| WO2015097605A1 (en) * | 2013-12-23 | 2015-07-02 | Mylan Laboratories Ltd. | Process for the preparation of sofosbuvir |
| WO2016035006A1 (en) * | 2014-09-01 | 2016-03-10 | Dr. Reddy’S Laboratories Limited | Novel nucleotide analogs, process for the preparation of sofosbuvir and its analogs, novel forms of sofosbuvir and solid dispersion of sofosbuvir |
| WO2016042576A1 (en) | 2014-09-16 | 2016-03-24 | Cadila Healthcare Limited | Co-crystal of sofosbuvir and amino acid and process for preparation thereof |
| CN104327138B (zh) * | 2014-10-21 | 2017-05-10 | 齐鲁制药有限公司 | Psi‑7977中间体化合物的制备方法 |
| USD791845S1 (en) | 2015-09-22 | 2017-07-11 | Samsung Electronics Co., Ltd. | Door guard for refrigerator |
| USD791200S1 (en) | 2015-09-24 | 2017-07-04 | Samsung Electronics Co., Ltd. | Door guard for refrigerator |
| US10239910B2 (en) | 2016-07-20 | 2019-03-26 | Optimus Drugs (P) Limited | Process for the preparation of sofosbuvir |
| CN109422710B (zh) * | 2017-08-28 | 2022-06-21 | 常州制药厂有限公司 | 一种索非布韦氟内酯中间体的制备方法 |
| CN111362989B (zh) * | 2020-03-19 | 2022-03-08 | 江苏工程职业技术学院 | 一种索非布韦关键中间体的制备方法 |
| WO2021202669A2 (en) | 2020-04-01 | 2021-10-07 | Reyoung Corporation | Nucleoside and nucleotide conjugate compounds and uses thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5A (en) * | 1836-08-10 | Thomas Blanchard | Machine for mortising solid wooden shells of ships' tackle-blocks | |
| US4526988A (en) * | 1983-03-10 | 1985-07-02 | Eli Lilly And Company | Difluoro antivirals and intermediate therefor |
| YU25500A (sh) * | 1999-05-11 | 2003-08-29 | Pfizer Products Inc. | Postupak za sintezu analoga nukleozida |
| US6462191B1 (en) * | 2000-07-13 | 2002-10-08 | Air Products And Chemicals, Inc. | Synthesis of 2-deoxy-2-fluoro-arabinose derivatives |
| SK286630B6 (sk) * | 2001-01-22 | 2009-02-05 | Merck & Co., Inc. | Nukleozidové deriváty, farmaceutický prostriedok s ich obsahom a ich použitie |
| JP2005533108A (ja) * | 2002-07-16 | 2005-11-04 | メルク エンド カムパニー インコーポレーテッド | Rna依存性rnaウイルスポリメラーゼの阻害剤としてのヌクレオシド誘導体 |
| EP2345659A1 (en) * | 2003-05-30 | 2011-07-20 | Pharmasset, Inc. | Modified fluorinated nucleoside analogues |
-
2005
- 2005-07-21 ES ES05775359T patent/ES2386005T3/es not_active Expired - Lifetime
- 2005-07-21 KR KR1020077003980A patent/KR101236669B1/ko not_active Expired - Lifetime
- 2005-07-21 AT AT05775359T patent/ATE543789T1/de active
- 2005-07-21 PL PL05775359T patent/PL1773856T3/pl unknown
- 2005-07-21 CA CA2735079A patent/CA2735079C/en not_active Expired - Lifetime
- 2005-07-21 MX MX2007000803A patent/MX2007000803A/es active IP Right Grant
- 2005-07-21 NZ NZ552927A patent/NZ552927A/en not_active IP Right Cessation
- 2005-07-21 EP EP05775359A patent/EP1773856B1/en not_active Expired - Lifetime
- 2005-07-21 KR KR1020117006244A patent/KR101235548B1/ko not_active Expired - Lifetime
- 2005-07-21 DK DK05775359.2T patent/DK1773856T3/da active
- 2005-07-21 JP JP2007522763A patent/JP5078612B2/ja not_active Expired - Lifetime
- 2005-07-21 PT PT05775359T patent/PT1773856E/pt unknown
- 2005-07-21 RU RU2007106574/04A patent/RU2407747C2/ru not_active IP Right Cessation
- 2005-07-21 AU AU2005267051A patent/AU2005267051B2/en not_active Expired
- 2005-07-21 EP EP11159814A patent/EP2348029A1/en not_active Withdrawn
- 2005-07-21 CN CN201110079046.3A patent/CN102199181B/zh not_active Expired - Lifetime
- 2005-07-21 CA CA2574651A patent/CA2574651C/en not_active Expired - Lifetime
- 2005-07-21 WO PCT/US2005/025916 patent/WO2006012440A2/en not_active Ceased
-
2007
- 2007-01-21 IL IL180832A patent/IL180832A/en not_active IP Right Cessation
-
2011
- 2011-03-03 AU AU2011200941A patent/AU2011200941C1/en not_active Expired
- 2011-03-07 IL IL211606A patent/IL211606A0/en not_active IP Right Cessation
- 2011-03-22 JP JP2011061926A patent/JP5351919B2/ja not_active Expired - Lifetime
Non-Patent Citations (2)
| Title |
|---|
| Carbohydrate Research, 1984, Vol. 129, pages 99-109 * |
| J. Org. Chem., 1988, Vol. 53, pages 2406-2409 * |
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