JP2006509800A5 - - Google Patents
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- JP2006509800A5 JP2006509800A5 JP2004558730A JP2004558730A JP2006509800A5 JP 2006509800 A5 JP2006509800 A5 JP 2006509800A5 JP 2004558730 A JP2004558730 A JP 2004558730A JP 2004558730 A JP2004558730 A JP 2004558730A JP 2006509800 A5 JP2006509800 A5 JP 2006509800A5
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- JP
- Japan
- Prior art keywords
- formula
- compound
- represented
- alkyl
- compound represented
- 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.)
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- 0 CC(CO)([C@](CC1(C2)C2[n]2c(N=C(*)NC3=O)c3nc2)*#C)C1=C Chemical compound CC(CO)([C@](CC1(C2)C2[n]2c(N=C(*)NC3=O)c3nc2)*#C)C1=C 0.000 description 9
- DOCCMIOGWPGCIS-MMWGEVLESA-N CC(OC[C@@H]([C@H](C1)[C@@H](C2)OC1=O)[C@H]2OC(C)=O)=O Chemical compound CC(OC[C@@H]([C@H](C1)[C@@H](C2)OC1=O)[C@H]2OC(C)=O)=O DOCCMIOGWPGCIS-MMWGEVLESA-N 0.000 description 1
- YKPXZQCYQAXHSN-WHXOCPIISA-N CC([C@H](C/C1=C\[n]2c(N=C(N)NC3=O)c3nc2)O)C1=C Chemical compound CC([C@H](C/C1=C\[n]2c(N=C(N)NC3=O)c3nc2)O)C1=C YKPXZQCYQAXHSN-WHXOCPIISA-N 0.000 description 1
- JEGBGWBIGYGEJL-SECBINFHSA-N C[C@](CO)(CCC12CC1)C2=C Chemical compound C[C@](CO)(CCC12CC1)C2=C JEGBGWBIGYGEJL-SECBINFHSA-N 0.000 description 1
- IEUKEEXRKUEKHK-HNNXBMFYSA-N C[C@]1(COCc2ccccc2)C(CO)=CCC1 Chemical compound C[C@]1(COCc2ccccc2)C(CO)=CCC1 IEUKEEXRKUEKHK-HNNXBMFYSA-N 0.000 description 1
- UYTPUPDQBNUYGX-UHFFFAOYSA-N NC(NC1=O)=Nc2c1nc[nH]2 Chemical compound NC(NC1=O)=Nc2c1nc[nH]2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 1
- FUEMPGVQRPETCM-UHFFFAOYSA-N NC(NC1OCc2ccccc2)=Nc2c1nc[nH]2 Chemical compound NC(NC1OCc2ccccc2)=Nc2c1nc[nH]2 FUEMPGVQRPETCM-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43254902P | 2002-12-11 | 2002-12-11 | |
| US60/432,549 | 2002-12-11 | ||
| PCT/US2003/039554 WO2004052310A2 (en) | 2002-12-11 | 2003-12-10 | Process and intermediates for synthesis entecavir |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010120589A Division JP2010222365A (ja) | 2002-12-11 | 2010-05-26 | 抗ウイルス剤[1S−(1α,3α,4β)]−2−アミノ−1,9−ジヒドロ−9−[4−ヒドロキシ−3−(ヒドロキシメチル)−2−メチレンシクロペンチル]−6H−プリン−6−オンの製造法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006509800A JP2006509800A (ja) | 2006-03-23 |
| JP2006509800A5 true JP2006509800A5 (https=) | 2007-02-01 |
| JP4726491B2 JP4726491B2 (ja) | 2011-07-20 |
Family
ID=32507962
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004558730A Expired - Lifetime JP4726491B2 (ja) | 2002-12-11 | 2003-12-10 | 抗ウイルス剤[1S−(1α,3α,4β)]−2−アミノ−1,9−ジヒドロ−9−[4−ヒドロキシ−3−(ヒドロキシメチル)−2−メチレンシクロペンチル]−6H−プリン−6−オンの製造法 |
| JP2010120589A Pending JP2010222365A (ja) | 2002-12-11 | 2010-05-26 | 抗ウイルス剤[1S−(1α,3α,4β)]−2−アミノ−1,9−ジヒドロ−9−[4−ヒドロキシ−3−(ヒドロキシメチル)−2−メチレンシクロペンチル]−6H−プリン−6−オンの製造法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010120589A Pending JP2010222365A (ja) | 2002-12-11 | 2010-05-26 | 抗ウイルス剤[1S−(1α,3α,4β)]−2−アミノ−1,9−ジヒドロ−9−[4−ヒドロキシ−3−(ヒドロキシメチル)−2−メチレンシクロペンチル]−6H−プリン−6−オンの製造法 |
Country Status (18)
| Country | Link |
|---|---|
| US (3) | US7034152B2 (https=) |
| EP (2) | EP2433941A1 (https=) |
| JP (2) | JP4726491B2 (https=) |
| KR (2) | KR101096830B1 (https=) |
| CN (6) | CN101130543B (https=) |
| AU (1) | AU2003300884B2 (https=) |
| BR (2) | BR122019020833B8 (https=) |
| CA (2) | CA2508811C (https=) |
| DK (1) | DK1644384T3 (https=) |
| ES (1) | ES2397104T3 (https=) |
| IL (1) | IL168691A (https=) |
| IN (3) | IN2012DN00606A (https=) |
| MX (1) | MXPA05005971A (https=) |
| PL (2) | PL212790B1 (https=) |
| PT (1) | PT1644384E (https=) |
| SI (1) | SI1644384T1 (https=) |
| TW (1) | TWI327568B (https=) |
| WO (1) | WO2004052310A2 (https=) |
Families Citing this family (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60313173T2 (de) * | 2002-06-27 | 2008-01-03 | F. Hoffmann-La Roche Ag | Synthese von purin-derivaten |
| SI1644384T1 (sl) * | 2002-12-11 | 2013-02-28 | Bristol-Myers Squibb Company | Postopek in intermediati za sintezo entekavirja |
| US7511139B2 (en) | 2004-06-04 | 2009-03-31 | Bristol-Myers Squibb Company | Process for the preparation of entecavir and novel intermediates thereof via carbon-silicon oxidation |
| TW200540175A (en) * | 2004-06-04 | 2005-12-16 | Bristol Myers Squibb Co | Process for the preparation of entecavir and novel intermediates thereof via carbon-silicon oxidation |
| CN100379736C (zh) * | 2005-05-13 | 2008-04-09 | 上海仲夏化学有限公司 | 恩替卡韦的制备方法 |
| CN1699366A (zh) * | 2005-06-03 | 2005-11-23 | 北京市典范科技有限责任公司 | 嘌呤衍生物 |
| US20070060599A1 (en) * | 2005-09-09 | 2007-03-15 | Dimarco John D | Crystalline forms of [1S-(1alpha, 3alpha, 4beta)]-2-amino-1,9-dihydro-9-[4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one |
| CN101130542B (zh) * | 2006-08-24 | 2010-08-04 | 江苏正大天晴药业股份有限公司 | 抗病毒核苷类似物的合成方法 |
| CN101838270B (zh) * | 2006-08-24 | 2012-04-18 | 江苏正大天晴药业股份有限公司 | 恩替卡韦的中间体及制备 |
| CN101838207B (zh) * | 2006-08-24 | 2012-04-25 | 江苏正大天晴药业股份有限公司 | 恩替卡韦的中间体及合成方法 |
| CN101863842B (zh) * | 2006-08-24 | 2012-02-01 | 江苏正大天晴药业股份有限公司 | 恩替卡韦中间体及合成方法 |
| US8299152B2 (en) * | 2006-10-30 | 2012-10-30 | Pirelli Tyre S.P.A. | Tire for vehicle wheels comprising crosslinked elastomeric composition |
| CN101371841A (zh) * | 2007-08-23 | 2009-02-25 | 浙江医药股份有限公司新昌制药厂 | 结晶型恩替卡韦制剂及其制备方法和应用 |
| CN101245068A (zh) | 2007-02-14 | 2008-08-20 | 浙江医药股份有限公司新昌制药厂 | 结晶型态的恩替卡韦及其制备方法和其药物组合物及用途 |
| CN101284799B (zh) | 2007-03-23 | 2013-04-03 | 浙江医药股份有限公司新昌制药厂 | 咖啡酰奎宁酸含氮衍生物及其制备方法和其药物组合物及用途 |
| CN101074217B (zh) * | 2007-04-04 | 2010-11-24 | 北京精华耀邦医药科技有限公司 | 通过制备色谱分离得到高纯度恩替卡韦关键中间体的方法 |
| CN101397333A (zh) | 2007-09-27 | 2009-04-01 | 浙江医药股份有限公司新昌制药厂 | 去羟基万古霉素及其制备方法、和其药物组合物及其用途 |
| CN101723945B (zh) * | 2008-10-17 | 2011-11-02 | 上海清松制药有限公司 | 一种制备抗病毒药物恩替卡韦中间体的方法 |
| KR101150254B1 (ko) * | 2008-12-26 | 2012-06-12 | 한미사이언스 주식회사 | 신규 중간체 및 이를 활용한 엔테카비르 제조방법 |
| CN101828693B (zh) | 2009-03-09 | 2013-01-02 | 浙江医药股份有限公司新昌制药厂 | 制备低粘度高流动性类胡萝卜素油悬浮液的方法及其应用 |
| CN101531660B (zh) * | 2009-04-14 | 2012-07-04 | 安徽贝克联合制药有限公司 | 一种恩替卡韦一水合物的工业化生产工艺 |
| PH12012500703A1 (en) * | 2009-10-12 | 2015-07-10 | Hanmi Science Co Ltd | Novel method for preparing entecavir and intermediate used therein |
| CN101693713B (zh) * | 2009-10-28 | 2011-11-09 | 福建广生堂药业有限公司 | 一种恩替卡韦的晶型及其制备方法和药物应用 |
| CN101781301B (zh) * | 2010-01-15 | 2013-04-10 | 复旦大学 | 一种制备恩替卡韦的方法 |
| US8481728B2 (en) | 2010-02-16 | 2013-07-09 | Scinopharm Taiwan, Ltd. | Process for preparing entecavir and its intermediates |
| CN101805339B (zh) * | 2010-04-12 | 2012-01-11 | 王明 | 一种制备恩替卡韦化合物的方法 |
| CA2705953C (en) * | 2010-05-31 | 2018-05-01 | Alphora Research Inc. | Carbanucleoside synthesis and intermediate compounds useful therein |
| CN101891741B (zh) * | 2010-07-06 | 2013-01-23 | 苏州汉德森医药科技有限公司 | 抗病毒药恩替卡韦的新合成工艺 |
| CN102336754B (zh) | 2010-07-15 | 2017-04-12 | 浙江奥翔药业股份有限公司 | 恩替卡韦的合成方法及其中间体化合物 |
| TWI668220B (zh) * | 2010-08-30 | 2019-08-11 | 浙江奧翔藥業股份有限公司 | 恩替卡韋的合成方法及其中間體化合物 |
| EP2474548A1 (en) | 2010-12-23 | 2012-07-11 | Esteve Química, S.A. | Preparation process of an antiviral drug and intermediates thereof |
| KR101269491B1 (ko) * | 2010-12-23 | 2013-05-31 | 주식회사 한서켐 | 엔테카비어 제조방법 |
| CN102225938A (zh) * | 2011-04-25 | 2011-10-26 | 海南卫康制药(潜山)有限公司 | 恩替卡韦一水合物新合成工艺 |
| CN102267875B (zh) * | 2011-06-17 | 2013-04-24 | 常州寅盛药业有限公司 | 一种恩替卡韦中间体的制备方法 |
| CN102952156A (zh) * | 2011-08-29 | 2013-03-06 | 南京工业大学 | 一种抗乙肝药物恩替卡韦中间体及其合成 |
| CN102952135B (zh) * | 2011-08-31 | 2015-04-08 | 南京工业大学 | 一种乙肝药物恩替卡韦的合成方法 |
| EP2597096A1 (en) | 2011-11-24 | 2013-05-29 | Esteve Química, S.A. | Process for preparing entecavir and intermediates thereof |
| CN103304375B (zh) * | 2012-03-12 | 2017-04-12 | 浙江奥翔药业股份有限公司 | 恩替卡韦的合成中间体及其制备方法 |
| CN107253967B (zh) | 2012-10-02 | 2021-03-30 | 加州理工学院 | 芳族化合物的无过渡金属的甲硅烷基化 |
| RU2650112C2 (ru) | 2012-10-02 | 2018-04-09 | Кэлифорниа Инститьют Оф Текнолоджи | Восстановительное расщепление ароматических связей c-o, c-n и c-s активированными силанами без переходных металлов |
| CN104017015B (zh) * | 2013-02-28 | 2017-04-05 | 浙江星月药物科技股份有限公司 | 一类恩替卡韦的中间体的制备方法,以及中间体 |
| CN104016984A (zh) * | 2013-02-28 | 2014-09-03 | 浙江星月药物科技股份有限公司 | 一种恩替卡韦及其中间体的制备方法,以及中间体 |
| CN104017016B (zh) * | 2013-02-28 | 2017-04-05 | 浙江星月药物科技股份有限公司 | 一类恩替卡韦的中间体的制备方法,以及中间体 |
| CN104017014A (zh) * | 2013-02-28 | 2014-09-03 | 浙江星月药物科技股份有限公司 | 一类恩替卡韦的中间体的制备方法,以及中间体 |
| CN104017012A (zh) * | 2013-02-28 | 2014-09-03 | 浙江星月药物科技股份有限公司 | 一类恩替卡韦的中间体的制备方法,以及中间体 |
| CN104177397B (zh) * | 2013-05-23 | 2017-10-13 | 浙江星月药物科技股份有限公司 | 恩替卡韦中间体及其制备方法 |
| CN104177394B (zh) * | 2013-05-23 | 2017-12-05 | 浙江星月药物科技股份有限公司 | 恩替卡韦中间体及其制备方法 |
| CN104177396A (zh) * | 2013-05-23 | 2014-12-03 | 浙江星月药物科技股份有限公司 | 恩替卡韦中间体及其制备方法 |
| GB201313238D0 (en) | 2013-07-24 | 2013-09-04 | Avexxin As | Process for the preparation of a polyunsaturated ketone compound |
| EP3705482B1 (en) * | 2014-08-06 | 2023-02-22 | California Institute of Technology | Silylation of aromatic heterocycles by earth abundant transition-metal-free catalysts |
| KR101640503B1 (ko) | 2015-04-15 | 2016-07-18 | 동방에프티엘(주) | 엔테카비르 일수화물의 개선된 제조방법 |
| KR101640504B1 (ko) | 2015-04-15 | 2016-07-18 | 동방에프티엘(주) | 엔테카비르 일수화물의 제조방법 |
| CN105037363B (zh) * | 2015-07-13 | 2016-08-24 | 山东罗欣药业集团股份有限公司 | 一种恩替卡韦化合物的新合成方法 |
| EP3789374A3 (en) * | 2016-04-07 | 2021-07-21 | University of Georgia Research Foundation, Inc. | Synthesis of 2'-fluoro-6'-methylene-carbocyclic adenosine (fmca) and 2'-fluoro-6'-methylene-carbocyclic guanosine (fmcg) |
| CN107325122B (zh) * | 2017-01-06 | 2020-05-01 | 常州博海威医药科技股份有限公司 | 制备贝前列腺素的新中间体及其制备方法 |
| CN107163049B (zh) * | 2017-05-31 | 2019-06-18 | 湖北远大生命科学与技术有限责任公司 | 一种恩替卡韦的制备方法 |
| CN109705063B (zh) | 2017-10-26 | 2021-01-01 | 广州市朗启医药科技有限责任公司 | 恩替卡韦中间体及其合成方法以及恩替卡韦的合成方法 |
| WO2019080686A1 (zh) * | 2017-10-26 | 2019-05-02 | 广州市朗启医药科技有限责任公司 | 恩替卡韦中间体及其合成方法以及恩替卡韦的合成方法 |
| CN109232637B (zh) * | 2018-10-29 | 2020-11-24 | 常州博海威医药科技股份有限公司 | 一种恩替卡韦中间体的制备方法 |
| CN109593090A (zh) * | 2019-01-25 | 2019-04-09 | 连云港贵科药业有限公司 | 一种恩替卡韦的合成方法 |
| CN113831341B (zh) * | 2020-06-08 | 2025-06-10 | 连云港润众制药有限公司 | 一种恩替卡韦的制备方法 |
| CN112625041A (zh) * | 2020-12-25 | 2021-04-09 | 常州博海威医药科技股份有限公司 | 恩替卡韦的新制备方法以及中间体 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4594439A (en) | 1980-08-06 | 1986-06-10 | The Board Of Trustees Of The Leland Stanford Jr. University | Method for asymmetric epoxidation |
| US4471130A (en) | 1980-08-06 | 1984-09-11 | The Board Of Trustees Of The Leland Stanford Junior University | Method for asymmetric epoxidation |
| US4900847A (en) | 1985-04-04 | 1990-02-13 | Massachusetts Institute Of Technology | Catalytic asymmetric epoxidation |
| JPH01207257A (ja) * | 1988-02-15 | 1989-08-21 | Nippon Oil & Fats Co Ltd | α−リノレン酸の分離法 |
| US5206244A (en) * | 1990-10-18 | 1993-04-27 | E. R. Squibb & Sons, Inc. | Hydroxymethyl (methylenecyclopentyl) purines and pyrimidines |
| EP0630897A3 (en) * | 1993-06-25 | 1995-03-01 | Bristol Myers Squibb Co | 3-hydroxy-4-hydroxymethyl-2-methylene-cyclopentyl purines and pyrimidines. |
| US5665890A (en) * | 1995-03-14 | 1997-09-09 | President And Fellows Of Harvard College | Stereoselective ring opening reactions |
| WO1998009964A1 (en) * | 1996-09-03 | 1998-03-12 | Bristol-Myers Squibb Company | IMPROVED PROCESS FOR PREPARING THE ANTIVIRAL AGENT [1S-(1α, 3α, 4β)]-2-AMINO-1,9-DIHYDRO-9-[4-HYDROXY-3-(HYDROXYMETHYL)-2-METHYLENECYCLOPENTYL]-6H-PURIN-6-ONE |
| US6127159A (en) * | 1997-06-06 | 2000-10-03 | The Board Of Trustees Of The Leland Stanford Junior University | Mitofusin genes and their uses |
| GEP20053504B (en) * | 2000-02-29 | 2005-05-10 | Bristol Myers Squibb Co | Low Dose Entecavir Pharmaceutical Composition and Use Thereof for Treatment of Hepatitis B |
| CA2311734C (en) * | 2000-04-12 | 2011-03-08 | Bristol-Myers Squibb Company | Flash-melt oral dosage formulation |
| EP1964569A3 (en) * | 2000-04-13 | 2009-07-22 | Pharmasset, Inc. | 3'-or 2'-hydroxymethyl substituted nucleoside derivatives for treatment of viral infections |
| SI1644384T1 (sl) * | 2002-12-11 | 2013-02-28 | Bristol-Myers Squibb Company | Postopek in intermediati za sintezo entekavirja |
| US7511139B2 (en) * | 2004-06-04 | 2009-03-31 | Bristol-Myers Squibb Company | Process for the preparation of entecavir and novel intermediates thereof via carbon-silicon oxidation |
| US20070060599A1 (en) * | 2005-09-09 | 2007-03-15 | Dimarco John D | Crystalline forms of [1S-(1alpha, 3alpha, 4beta)]-2-amino-1,9-dihydro-9-[4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one |
-
2003
- 2003-12-10 SI SI200332236T patent/SI1644384T1/sl unknown
- 2003-12-10 WO PCT/US2003/039554 patent/WO2004052310A2/en not_active Ceased
- 2003-12-10 PT PT38129748T patent/PT1644384E/pt unknown
- 2003-12-10 AU AU2003300884A patent/AU2003300884B2/en not_active Expired
- 2003-12-10 CN CN2007101499445A patent/CN101130543B/zh not_active Expired - Lifetime
- 2003-12-10 IN IN606DEN2012 patent/IN2012DN00606A/en unknown
- 2003-12-10 BR BR122019020833A patent/BR122019020833B8/pt active IP Right Grant
- 2003-12-10 IN IN605DEN2012 patent/IN2012DN00605A/en unknown
- 2003-12-10 CN CN201210089818.6A patent/CN102675355B/zh not_active Expired - Lifetime
- 2003-12-10 CA CA2508811A patent/CA2508811C/en not_active Expired - Fee Related
- 2003-12-10 EP EP11189882A patent/EP2433941A1/en not_active Withdrawn
- 2003-12-10 EP EP03812974A patent/EP1644384B1/en not_active Expired - Lifetime
- 2003-12-10 PL PL377263A patent/PL212790B1/pl unknown
- 2003-12-10 KR KR1020097015624A patent/KR101096830B1/ko not_active Expired - Lifetime
- 2003-12-10 CN CN2007101499407A patent/CN101130552B/zh not_active Expired - Lifetime
- 2003-12-10 DK DK03812974.8T patent/DK1644384T3/da active
- 2003-12-10 KR KR1020057010722A patent/KR100944063B1/ko not_active Expired - Lifetime
- 2003-12-10 ES ES03812974T patent/ES2397104T3/es not_active Expired - Lifetime
- 2003-12-10 JP JP2004558730A patent/JP4726491B2/ja not_active Expired - Lifetime
- 2003-12-10 CN CN201510061020.4A patent/CN104788485B/zh not_active Expired - Lifetime
- 2003-12-10 CN CN2010102360003A patent/CN101899063B/zh not_active Expired - Lifetime
- 2003-12-10 PL PL397715A patent/PL397715A1/pl unknown
- 2003-12-10 BR BRPI0317255A patent/BRPI0317255B8/pt not_active IP Right Cessation
- 2003-12-10 CA CA2735485A patent/CA2735485A1/en not_active Abandoned
- 2003-12-10 CN CNB2003801056146A patent/CN100379746C/zh not_active Expired - Lifetime
- 2003-12-10 MX MXPA05005971A patent/MXPA05005971A/es active IP Right Grant
- 2003-12-10 IN IN604DEN2012 patent/IN2012DN00604A/en unknown
- 2003-12-11 TW TW092135079A patent/TWI327568B/zh not_active IP Right Cessation
- 2003-12-11 US US10/734,012 patent/US7034152B2/en not_active Expired - Lifetime
-
2005
- 2005-05-19 IL IL168691A patent/IL168691A/en active IP Right Grant
- 2005-12-19 US US11/311,194 patent/US7541460B2/en not_active Expired - Lifetime
- 2005-12-19 US US11/311,598 patent/US7550619B2/en not_active Expired - Lifetime
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2010
- 2010-05-26 JP JP2010120589A patent/JP2010222365A/ja active Pending
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