AR074821A1 - Proceso para preparar entecavir e intermediario para dicho proceso - Google Patents
Proceso para preparar entecavir e intermediario para dicho procesoInfo
- Publication number
- AR074821A1 AR074821A1 ARP090105004A ARP090105004A AR074821A1 AR 074821 A1 AR074821 A1 AR 074821A1 AR P090105004 A ARP090105004 A AR P090105004A AR P090105004 A ARP090105004 A AR P090105004A AR 074821 A1 AR074821 A1 AR 074821A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compound
- protecting group
- hydroxy protecting
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- 229960000980 entecavir Drugs 0.000 title 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 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 4
- -1 nucleoside compound Chemical class 0.000 abstract 3
- 125000006239 protecting group Chemical group 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 239000002777 nucleoside Substances 0.000 abstract 2
- 238000006751 Mitsunobu reaction Methods 0.000 abstract 1
- 125000005103 alkyl silyl group Chemical group 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
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 238000006772 olefination reaction Methods 0.000 abstract 1
- 150000003212 purines Chemical class 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
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Abstract
Reivindicación 1: Un método para preparar entecavir de la fórmula (1), caracterizado porque comprende los pasos de: (a) realizar olefinación de un compuesto alfa-hidroxi cetona de la fórmula (2) para obtener un compuesto exometileno de la fórmula (3); (b) llevar a cabo una reacción de Mitsunobu del compuesto exometileno de la fórmula (3) con un derivado de purina para obtener un compuesto nucleósido de la fórmula (4); (c) extraer los grupos protectores del compuesto nucleósido de la fórmula (4) para obtener un compuesto de la fórmula (5); y (d) hidrolizar el compuesto de la fórmula (5), en donde, R1 y R2 son cada uno, independientemente, H o un grupo protector hidroxi, o R1 y R2 se fusionan de manera conjunta para formar un grupo protector hidroxi cíclico, R3 se selecciona del grupo que consiste de H, alquilsililo, y alilsililo; y X se selecciona del grupo que consiste de cloro, yodo, y benciloxi. Reivindicación 12: Un compuesto cetona caracterizado porque es de fórmula (6) en donde R1 y R2 son cada uno, independientemente, H o un grupo protector hidroxi, o R1 y R2 se fusionan de manera conjunta para formar un grupo protector hidroxi cíclico.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020080134756A KR101150254B1 (ko) | 2008-12-26 | 2008-12-26 | 신규 중간체 및 이를 활용한 엔테카비르 제조방법 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR074821A1 true AR074821A1 (es) | 2011-02-16 |
Family
ID=42288324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP090105004A AR074821A1 (es) | 2008-12-26 | 2009-12-21 | Proceso para preparar entecavir e intermediario para dicho proceso |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8569490B2 (es) |
| EP (1) | EP2382217B1 (es) |
| JP (1) | JP5425933B2 (es) |
| KR (1) | KR101150254B1 (es) |
| CN (1) | CN102264739B (es) |
| AR (1) | AR074821A1 (es) |
| CA (1) | CA2747777C (es) |
| MY (1) | MY158838A (es) |
| SA (1) | SA109310017B1 (es) |
| SG (1) | SG171963A1 (es) |
| TW (1) | TWI383983B (es) |
| WO (1) | WO2010074534A2 (es) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011046303A2 (en) * | 2009-10-12 | 2011-04-21 | Hanmi Holdings Co., Ltd. | Novel method for preparing entecavir and intermediate used therein |
| US8481728B2 (en) * | 2010-02-16 | 2013-07-09 | Scinopharm Taiwan, Ltd. | Process for preparing entecavir and its intermediates |
| CA2705953C (en) * | 2010-05-31 | 2018-05-01 | Alphora Research Inc. | Carbanucleoside synthesis and intermediate compounds useful therein |
| 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 |
| EP2474548A1 (en) | 2010-12-23 | 2012-07-11 | Esteve Química, S.A. | Preparation process of an antiviral drug and intermediates thereof |
| EP2597096A1 (en) | 2011-11-24 | 2013-05-29 | Esteve Química, S.A. | Process for preparing entecavir and intermediates thereof |
| US9169256B2 (en) | 2013-03-13 | 2015-10-27 | Elitechgroup B.V. | Artificial nucleic acids |
| ES2828642T3 (es) * | 2013-06-25 | 2021-05-27 | Walter & Eliza Hall Inst Medical Res | Miméticos Smac para el tratamiento de una infección intracelular persistente de VHB |
| WO2015051903A1 (en) * | 2013-10-08 | 2015-04-16 | Pharmathen S.A. | A novel process for the preparation of chiral cyclopentanone intermediates |
| WO2015051900A1 (en) | 2013-10-08 | 2015-04-16 | Pharmathen S.A. | Process for the preparation of entecavir through novel intermediates |
| CN103675185B (zh) * | 2013-12-10 | 2015-10-07 | 上海景峰制药股份有限公司 | 一种用高效液相色谱法测定恩替卡韦片中全反式异构体的方法 |
| KR101647061B1 (ko) | 2014-04-02 | 2016-08-10 | 서강대학교산학협력단 | 무인자율주행 차량의 주행경로 생성방법 및 장치 |
| 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 |
| CN106554365B (zh) * | 2016-11-12 | 2019-01-08 | 嘉兴敏实机械有限公司 | 一种恩替卡韦中间体的制备工艺及其应用 |
| 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 |
| MX2021006993A (es) * | 2018-12-12 | 2021-10-22 | Janssen Biopharma Inc | Analogos de nucleosidos de ciclopentilo como antivirales. |
| CN118852236B (zh) * | 2024-07-24 | 2025-11-25 | 南京工业大学 | 一种恩替卡韦的合成中间体、恩替卡韦的制备方法 |
Family Cites Families (11)
| 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 |
| US5340816A (en) | 1990-10-18 | 1994-08-23 | 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 |
| PL1628685T3 (pl) | 2003-04-25 | 2011-05-31 | Gilead Sciences Inc | Przeciwwirusowe analogi fosfonianowe |
| 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 |
| CN101210015B (zh) | 2006-12-26 | 2010-09-22 | 上海国创医药有限公司 | 一种乙肝治疗药物恩替卡韦的制备方法 |
| CN101245067B (zh) | 2007-02-14 | 2011-09-28 | 浙江金立源药业有限公司 | 一种恩替卡韦的制备方法及其中间体 |
| 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 |
| CN101235034A (zh) | 2008-02-28 | 2008-08-06 | 陆锦康 | 恩替卡韦的合成方法 |
-
2008
- 2008-12-26 KR KR1020080134756A patent/KR101150254B1/ko not_active Expired - Fee Related
-
2009
- 2009-12-21 AR ARP090105004A patent/AR074821A1/es not_active Application Discontinuation
- 2009-12-23 SA SA109310017A patent/SA109310017B1/ar unknown
- 2009-12-24 JP JP2011543432A patent/JP5425933B2/ja not_active Expired - Fee Related
- 2009-12-24 WO PCT/KR2009/007786 patent/WO2010074534A2/en not_active Ceased
- 2009-12-24 CA CA2747777A patent/CA2747777C/en not_active Expired - Fee Related
- 2009-12-24 SG SG2011040870A patent/SG171963A1/en unknown
- 2009-12-24 EP EP09835300.6A patent/EP2382217B1/en not_active Not-in-force
- 2009-12-24 US US13/140,640 patent/US8569490B2/en not_active Expired - Fee Related
- 2009-12-24 MY MYPI2011002833A patent/MY158838A/en unknown
- 2009-12-24 CN CN200980152328.2A patent/CN102264739B/zh not_active Expired - Fee Related
- 2009-12-25 TW TW098145014A patent/TWI383983B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CN102264739A (zh) | 2011-11-30 |
| US8569490B2 (en) | 2013-10-29 |
| JP5425933B2 (ja) | 2014-02-26 |
| HK1163083A1 (en) | 2012-09-07 |
| WO2010074534A3 (en) | 2010-11-11 |
| TW201028417A (en) | 2010-08-01 |
| US20110251387A1 (en) | 2011-10-13 |
| SA109310017B1 (ar) | 2013-12-15 |
| CA2747777C (en) | 2013-11-12 |
| KR20100076640A (ko) | 2010-07-06 |
| CN102264739B (zh) | 2014-12-10 |
| JP2012513988A (ja) | 2012-06-21 |
| EP2382217B1 (en) | 2013-10-23 |
| TWI383983B (zh) | 2013-02-01 |
| SG171963A1 (en) | 2011-07-28 |
| WO2010074534A2 (en) | 2010-07-01 |
| KR101150254B1 (ko) | 2012-06-12 |
| MY158838A (en) | 2016-11-15 |
| EP2382217A2 (en) | 2011-11-02 |
| CA2747777A1 (en) | 2010-07-01 |
| EP2382217A4 (en) | 2012-08-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FC | Refusal |