KR940000475A - 알파-아노머가 풍부한 1-할로-2-데옥시-2, 2-디플루오로-d-리보푸라노실 유도체의 제조방법 - Google Patents
알파-아노머가 풍부한 1-할로-2-데옥시-2, 2-디플루오로-d-리보푸라노실 유도체의 제조방법 Download PDFInfo
- Publication number
- KR940000475A KR940000475A KR1019930011310A KR930011310A KR940000475A KR 940000475 A KR940000475 A KR 940000475A KR 1019930011310 A KR1019930011310 A KR 1019930011310A KR 930011310 A KR930011310 A KR 930011310A KR 940000475 A KR940000475 A KR 940000475A
- Authority
- KR
- South Korea
- Prior art keywords
- halides
- deoxy
- ribofuranosyl
- halo
- halide source
- 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.)
- Abandoned
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 150000004820 halides Chemical class 0.000 claims abstract 6
- 239000012442 inert solvent Substances 0.000 claims abstract 2
- 230000000707 stereoselective effect Effects 0.000 claims abstract 2
- -1 tetraalkylammonium halides Chemical class 0.000 claims 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims 2
- 229910052792 caesium Inorganic materials 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000000701 coagulant Substances 0.000 claims 1
- 150000003983 crown ethers Chemical class 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims 1
Classifications
-
- 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
- C07H5/02—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 halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US90230692A | 1992-06-22 | 1992-06-22 | |
| US902,306 | 1992-06-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR940000475A true KR940000475A (ko) | 1994-01-03 |
Family
ID=25415658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019930011310A Abandoned KR940000475A (ko) | 1992-06-22 | 1993-06-21 | 알파-아노머가 풍부한 1-할로-2-데옥시-2, 2-디플루오로-d-리보푸라노실 유도체의 제조방법 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5453499A (cg-RX-API-DMAC10.html) |
| EP (1) | EP0576231B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JP3291071B2 (cg-RX-API-DMAC10.html) |
| KR (1) | KR940000475A (cg-RX-API-DMAC10.html) |
| AT (1) | ATE153669T1 (cg-RX-API-DMAC10.html) |
| BR (1) | BR9302427A (cg-RX-API-DMAC10.html) |
| CA (1) | CA2098887C (cg-RX-API-DMAC10.html) |
| DE (1) | DE69311000T2 (cg-RX-API-DMAC10.html) |
| DK (1) | DK0576231T3 (cg-RX-API-DMAC10.html) |
| ES (1) | ES2103433T3 (cg-RX-API-DMAC10.html) |
| GR (1) | GR3023911T3 (cg-RX-API-DMAC10.html) |
| HU (1) | HU214030B (cg-RX-API-DMAC10.html) |
| IL (1) | IL106075A (cg-RX-API-DMAC10.html) |
| MX (1) | MX9303713A (cg-RX-API-DMAC10.html) |
| TW (1) | TW224102B (cg-RX-API-DMAC10.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100449618B1 (ko) * | 1998-03-27 | 2004-11-16 | 부광약품 주식회사 | 2'-플루오로-5-메틸-β-L-아라비노푸라노실유리딘의 제조방법 |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7214791B2 (en) * | 2004-07-01 | 2007-05-08 | Shenzhen Hande Technology Co., Ltd. | Method for preparation of 2′-deoxy-2′, 2′-difluoro-β-cytidine or pharmaceutically acceptable salts thereof by using 1,6-anhydro-β-d-glucose as raw material |
| 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 |
| KR100578616B1 (ko) * | 2004-07-23 | 2006-05-10 | 한미약품 주식회사 | Ｄ-에리트로-2,2-다이플루오로-2-데옥시-1-옥소라이보스화합물의 제조방법 |
| EP1781678A4 (en) | 2004-07-29 | 2012-04-25 | Hanmi Holdings Co Ltd | 1-alpha-halo-2,2-difluoro-2-deoxy-d-ribofuranose derivatives and process for the preparation thereof |
| KR100699099B1 (ko) * | 2004-07-29 | 2007-03-22 | 한미약품 주식회사 | 1-α-할로-2,2-다이플루오로-2-데옥시-Ｄ-라이보퓨라노스유도체 및 이의 제조방법 |
| BRPI0515279A (pt) * | 2004-09-14 | 2008-07-15 | Pharmasset Inc | preparação de ribofuranosil pirimidinas e purinas 2'fluoro-2'-alquil- substituìdas ou outras opcionalmente substituìdas e seus derivados |
| CN101437524B (zh) * | 2004-09-14 | 2012-01-11 | 法莫赛特股份有限公司 | 2＇-氟-2＇-烷基-取代的或其它任选取代的呋喃核糖基嘧啶和嘌呤及其衍生物的制备 |
| AT502221A1 (de) * | 2005-07-20 | 2007-02-15 | Pharmacon Forschung & Beratung Gmbh | Homogemcitabine, verfahren zu ihrer herstellung sowie deren verwendung |
| JP5349342B2 (ja) * | 2007-03-23 | 2013-11-20 | ドンウ シンテック カンパニー リミテッド | ２’−デオキシ−２’，２’−ジフルオロシチジンの製造方法 |
| KR100858842B1 (ko) | 2007-03-23 | 2008-09-22 | 동우신테크 주식회사 | 키랄아민을 이용한 광학활성 옥소라이보스유도체의제조방법 |
| 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 |
| WO2010075554A1 (en) | 2008-12-23 | 2010-07-01 | Pharmasset, Inc. | Synthesis of purine nucleosides |
| 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 |
| RS54368B1 (sr) | 2010-03-31 | 2016-04-28 | Gilead Pharmasset Llc | Kristalni (s)-izopropil 2-(((s)-(((2r,3r,4r,5r)-5-(2,4-diokso-3,4-dihidropirimidin-1-(2h)-il)-4-fluoro-3-hidroksi-4-metiltetrahidrofuran-2-il)metoksi)(fenoksi)fosforil)amino)propanoat |
| 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 |
| CA2818853A1 (en) | 2010-11-30 | 2012-06-07 | Gilead Pharmasset Llc | 2'-spirocyclo-nucleosides for use in therapy of hcv or dengue virus |
| US8889159B2 (en) | 2011-11-29 | 2014-11-18 | Gilead Pharmasset Llc | Compositions and methods for treating hepatitis C virus |
| SG11201600919UA (en) | 2013-08-27 | 2016-03-30 | Gilead Pharmasset Llc | Combination formulation of two antiviral compounds |
| CN106317147B (zh) * | 2015-07-06 | 2018-11-27 | 扬州硒瑞恩生物医药科技有限公司 | 核苷类化合物及其制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3277077A (en) * | 1964-06-03 | 1966-10-04 | Merck & Co Inc | 3-deoxy ribofuranosyl halides |
| US4526988A (en) * | 1983-03-10 | 1985-07-02 | Eli Lilly And Company | Difluoro antivirals and intermediate therefor |
| US4965374A (en) * | 1987-08-28 | 1990-10-23 | Eli Lilly And Company | Process for and intermediates of 2',2'-difluoronucleosides |
| US5256797A (en) * | 1992-06-22 | 1993-10-26 | Eli Lilly And Company | Process for separating 2-deoxy-2,2-difluoro-D-ribofuranosyl alkylsulfonate anomers |
| US5256798A (en) * | 1992-06-22 | 1993-10-26 | Eli Lilly And Company | Process for preparing alpha-anomer enriched 2-deoxy-2,2-difluoro-D-ribofuranosyl sulfonates |
| US5252756A (en) * | 1992-06-22 | 1993-10-12 | Eli Lilly And Company | Process for preparing beta-anomer enriched 2-deoxy-2,2-difluoro-D-ribofuranosyl-arylsulfonates |
-
1993
- 1993-06-21 IL IL10607593A patent/IL106075A/xx not_active IP Right Cessation
- 1993-06-21 ES ES93304820T patent/ES2103433T3/es not_active Expired - Lifetime
- 1993-06-21 AT AT93304820T patent/ATE153669T1/de active
- 1993-06-21 EP EP93304820A patent/EP0576231B1/en not_active Expired - Lifetime
- 1993-06-21 KR KR1019930011310A patent/KR940000475A/ko not_active Abandoned
- 1993-06-21 DK DK93304820.9T patent/DK0576231T3/da active
- 1993-06-21 DE DE69311000T patent/DE69311000T2/de not_active Expired - Lifetime
- 1993-06-21 BR BR9302427A patent/BR9302427A/pt not_active Application Discontinuation
- 1993-06-21 MX MX9303713A patent/MX9303713A/es not_active IP Right Cessation
- 1993-06-21 JP JP14914993A patent/JP3291071B2/ja not_active Expired - Fee Related
- 1993-06-21 HU HU9301828A patent/HU214030B/hu not_active IP Right Cessation
- 1993-06-21 CA CA002098887A patent/CA2098887C/en not_active Expired - Lifetime
- 1993-06-22 TW TW082104990A patent/TW224102B/zh active
- 1993-07-29 US US08/099,014 patent/US5453499A/en not_active Expired - Lifetime
-
1997
- 1997-06-26 GR GR970401559T patent/GR3023911T3/el unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100449618B1 (ko) * | 1998-03-27 | 2004-11-16 | 부광약품 주식회사 | 2'-플루오로-5-메틸-β-L-아라비노푸라노실유리딘의 제조방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2098887A1 (en) | 1993-12-23 |
| DE69311000D1 (de) | 1997-07-03 |
| HU214030B (en) | 1997-12-29 |
| IL106075A (en) | 2000-12-06 |
| US5453499A (en) | 1995-09-26 |
| IL106075A0 (en) | 1993-10-20 |
| HUT64550A (en) | 1994-01-28 |
| EP0576231A1 (en) | 1993-12-29 |
| BR9302427A (pt) | 1994-01-11 |
| TW224102B (cg-RX-API-DMAC10.html) | 1994-05-21 |
| DE69311000T2 (de) | 1997-11-27 |
| JPH0656863A (ja) | 1994-03-01 |
| HU9301828D0 (en) | 1993-09-28 |
| JP3291071B2 (ja) | 2002-06-10 |
| CA2098887C (en) | 2003-10-28 |
| ES2103433T3 (es) | 1997-09-16 |
| ATE153669T1 (de) | 1997-06-15 |
| DK0576231T3 (da) | 1997-08-25 |
| GR3023911T3 (en) | 1997-09-30 |
| MX9303713A (es) | 1994-05-31 |
| EP0576231B1 (en) | 1997-05-28 |
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Legal Events
| Date | Code | Title | Description |
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| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19930621 |
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| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 19980618 Comment text: Request for Examination of Application Patent event code: PA02011R01I Patent event date: 19930621 Comment text: Patent Application |
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| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20000831 Patent event code: PE09021S01D |
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| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 20011010 |
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| NORF | Unpaid initial registration fee | ||
| PC1904 | Unpaid initial registration fee |