AR078557A1 - Metodo para preparar entecavir e intermediario usado en el mismo - Google Patents
Metodo para preparar entecavir e intermediario usado en el mismoInfo
- Publication number
- AR078557A1 AR078557A1 ARP100103657A ARP100103657A AR078557A1 AR 078557 A1 AR078557 A1 AR 078557A1 AR P100103657 A ARP100103657 A AR P100103657A AR P100103657 A ARP100103657 A AR P100103657A AR 078557 A1 AR078557 A1 AR 078557A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compound
- preparing
- 2theta
- hydrolyzing
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 9
- 150000001875 compounds Chemical class 0.000 abstract 5
- 238000002441 X-ray diffraction Methods 0.000 abstract 2
- 229960000980 entecavir Drugs 0.000 abstract 2
- YXPVEXCTPGULBZ-WQYNNSOESA-N entecavir hydrate Chemical compound O.C1=NC=2C(=O)NC(N)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)C1=C YXPVEXCTPGULBZ-WQYNNSOESA-N 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 239000002777 nucleoside Substances 0.000 abstract 2
- -1 nucleoside compound Chemical class 0.000 abstract 2
- 230000005855 radiation Effects 0.000 abstract 2
- 238000001228 spectrum Methods 0.000 abstract 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 abstract 2
- 238000006751 Mitsunobu reaction Methods 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000003212 purines Chemical class 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
-
- 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
-
- 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
- A61P31/20—Antivirals for DNA viruses
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (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)
- Steroid Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
Reivindicacion 1: Un método para preparar entecavir de la formula (1), caracterizado porque comprende los pasos de: (a) hidrolizar un derivado de alfa-exometileno de la formula (2) para obtener un compuesto de la formula (3), (b) llevar a cabo una reaccion de Mitsunobu del compuesto de la formula (3) con un derivado de purina de la formula (4) para obtener un compuesto nucleosido de la formula (5); (c) someter el compuesto nucleosido de la formula (5) a una reaccion con fluoruro de tetrabutil amonio para obtener un compuesto de la formula (6); y (d) hidrolizar el compuesto de la formula (6) en donde, R1 y R2 son, cada uno, en forma independiente, un grupo protector de hidroxilo, o R1 y R2 se fusionan para formar un grupo protector de hidroxilo cíclico; R3 es benzoilo o arilbenzoilo; Tf es trifluorometansulfonilo; y X es halogeno o benciloxi. Reivindicacion 30: El compuesto cristalino de acuerdo con la reivindicacion 29, caracterizado porque su espectro de difraccion de rayos X obtenido usando radiacion exhibe picos que tienen una intensidad del 10% o más en los ángulos de difraccion (2theta+- 0,2) de 8,5; 8,9; 10,4; 11,8; 13,2; 13,6; 14,0; 15,7; 17,3; 17,9; 18,4; 18,9; 19,4; 20,2; 20,6; 20,9; 21,6; 22,0; y 25,2. Reivindicacion 31: Un solvato de dimetilformamida de entecavir cristalino de la formula (1) caracterizado porque su espectro de difraccion de rayos X obtenido usando radiacion exhibe picos que tienen una intensidad del 10% o más en los ángulos de difraccion (2theta+- 0,2) de 10,2; 14,4; 14,5; 16,6; 17,9; 18,8; 19,3; 19,8; 21,4; 21,9; 24,5; 25,5; 25,8; 26,7; 29,3; y 30,2, en donde, la formula (1) es dimetilformamida (DMF).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20090096875 | 2009-10-12 | ||
| KR20100020106 | 2010-03-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR078557A1 true AR078557A1 (es) | 2011-11-16 |
Family
ID=43876661
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP100103657A AR078557A1 (es) | 2009-10-12 | 2010-10-07 | Metodo para preparar entecavir e intermediario usado en el mismo |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US8569491B2 (es) |
| EP (1) | EP2488522B1 (es) |
| JP (1) | JP5788398B2 (es) |
| KR (1) | KR101301200B1 (es) |
| CN (1) | CN102596956B (es) |
| AR (1) | AR078557A1 (es) |
| AU (1) | AU2010307562B2 (es) |
| CA (1) | CA2777018C (es) |
| IL (1) | IL219099A (es) |
| PH (1) | PH12012500703A1 (es) |
| SA (1) | SA110310757B1 (es) |
| TW (1) | TWI429648B (es) |
| WO (1) | WO2011046303A2 (es) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| CN103664943B (zh) * | 2012-09-06 | 2015-12-02 | 天津长森药业有限公司 | 嘌呤衍生物的制备方法及其中间体和应用 |
| CN102863444B (zh) * | 2012-09-06 | 2016-08-03 | 上海长森药业有限公司 | 一类嘌呤衍生物的制备方法及其中间体 |
| 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 |
| CN103304566B (zh) * | 2013-07-09 | 2015-11-04 | 北京凯因科技股份有限公司 | 一种结晶型恩替卡韦 |
| 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 |
| CN105001223B (zh) * | 2015-06-30 | 2016-08-17 | 湖南三清药业有限公司 | 一种恩替卡韦晶体化合物及其胶囊制剂 |
| CN106565769B (zh) * | 2016-11-12 | 2018-12-04 | 北京汇康博源医药科技有限公司 | 恩替卡韦中间体的合成工艺 |
| 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 (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5206244A (en) * | 1990-10-18 | 1993-04-27 | E. R. Squibb & Sons, Inc. | Hydroxymethyl (methylenecyclopentyl) purines and pyrimidines |
| AU4090697A (en) * | 1996-09-03 | 1998-03-26 | Bristol-Myers Squibb Company | Improved process for preparing the antiviral agent {1s-(1alpha, 3alpha, 4beta)}-2-amino-1,9-dihydro-9-{4-hydroxy-3-(hydroxymethyl)-2 -methylenecyclopentyl}-6h-purin-6-one |
| CA2735485A1 (en) * | 2002-12-11 | 2004-06-24 | Bristol-Myers Squibb Company | Process for preparing the antiviral agent [1s-(1.alpha., 3.alpha., 4.beta)]-2-amino-1,9-dihydro-9-[4-hydroxy-3-(hydroxymethyl)-2-methylenecycloppentyl]-6h-purin-6-one |
| WO2005000790A1 (ja) * | 2003-06-26 | 2005-01-06 | Taisho Pharmaceutical Co., Ltd. | ２－アミノビシクロ[３．１．０]ヘキサン－２，６－ジカルボン酸誘導体 |
| 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 |
| 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 |
| KR101150254B1 (ko) * | 2008-12-26 | 2012-06-12 | 한미사이언스 주식회사 | 신규 중간체 및 이를 활용한 엔테카비르 제조방법 |
-
2010
- 2010-09-15 WO PCT/KR2010/006306 patent/WO2011046303A2/en not_active Ceased
- 2010-09-15 AU AU2010307562A patent/AU2010307562B2/en not_active Ceased
- 2010-09-15 CA CA2777018A patent/CA2777018C/en not_active Expired - Fee Related
- 2010-09-15 US US13/501,414 patent/US8569491B2/en not_active Expired - Fee Related
- 2010-09-15 PH PH1/2012/500703A patent/PH12012500703A1/en unknown
- 2010-09-15 KR KR1020100090327A patent/KR101301200B1/ko not_active Expired - Fee Related
- 2010-09-15 EP EP10823545.8A patent/EP2488522B1/en not_active Not-in-force
- 2010-09-15 JP JP2012534093A patent/JP5788398B2/ja not_active Expired - Fee Related
- 2010-09-15 CN CN201080045738.XA patent/CN102596956B/zh not_active Expired - Fee Related
- 2010-10-07 AR ARP100103657A patent/AR078557A1/es unknown
- 2010-10-09 SA SA110310757A patent/SA110310757B1/ar unknown
- 2010-10-11 TW TW099134574A patent/TWI429648B/zh not_active IP Right Cessation
-
2012
- 2012-04-05 IL IL219099A patent/IL219099A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| TWI429648B (zh) | 2014-03-11 |
| IL219099A (en) | 2016-02-29 |
| KR20110040671A (ko) | 2011-04-20 |
| AU2010307562A1 (en) | 2012-06-07 |
| CA2777018A1 (en) | 2011-04-21 |
| HK1172033A1 (en) | 2013-04-12 |
| JP5788398B2 (ja) | 2015-09-30 |
| US20120202998A1 (en) | 2012-08-09 |
| KR101301200B1 (ko) | 2013-09-06 |
| CN102596956B (zh) | 2014-09-24 |
| EP2488522B1 (en) | 2017-02-15 |
| PH12012500703A1 (en) | 2015-07-10 |
| WO2011046303A3 (en) | 2011-10-06 |
| US8569491B2 (en) | 2013-10-29 |
| WO2011046303A2 (en) | 2011-04-21 |
| AU2010307562B2 (en) | 2013-05-16 |
| EP2488522A2 (en) | 2012-08-22 |
| JP2013507436A (ja) | 2013-03-04 |
| SA110310757B1 (ar) | 2014-02-27 |
| TW201118097A (en) | 2011-06-01 |
| EP2488522A4 (en) | 2013-05-29 |
| CN102596956A (zh) | 2012-07-18 |
| IL219099A0 (en) | 2012-06-28 |
| CA2777018C (en) | 2014-04-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure |