AR050339A1 - PROCESS FOR THE PREPARATION OF ENTECAVIR AND NEW INTERMEDIARIES OF THE SAME VIA CARBON-SILICON OXIDATION. - Google Patents
PROCESS FOR THE PREPARATION OF ENTECAVIR AND NEW INTERMEDIARIES OF THE SAME VIA CARBON-SILICON OXIDATION.Info
- Publication number
- AR050339A1 AR050339A1 ARP050102291A ARP050102291A AR050339A1 AR 050339 A1 AR050339 A1 AR 050339A1 AR P050102291 A ARP050102291 A AR P050102291A AR P050102291 A ARP050102291 A AR P050102291A AR 050339 A1 AR050339 A1 AR 050339A1
- Authority
- AR
- Argentina
- Prior art keywords
- compound
- formula
- defined hereinbefore
- preparation
- give
- Prior art date
Links
Classifications
-
- 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
Abstract
Los procesos para la preparacion del entecavir y los nuevos intermediarios del mismo, utilizando la oxidacion de carbono-silicio. Composiciones químicas. Reivindicacion 3: Un proceso para la preparacion de un compuesto de la formula (1) en donde cada Rb es alquilo C1-4, e Y es OBn, Cl, Br o I; caracterizado por que comprende: a) la reaccion de un compuesto de la formula (2) en donde cada Rb es como se definio anteriormente en la presente, con haluro de RaSi(Rb)2, en donde Ra es alilo, fenilo o fenilo sustituido con uno dos o tres alquilos C1-4 o alcoxi C1-4; y cada Rb es como se define anteriormente en la presente; en presencia de una base para dar un compuesto de la formula (3) en donde Ra y cada Rb son como se definieron anteriormente en la presente; b) la desproteccion del grupo PMB en el compuesto de la formula (3) para dar un compuesto de la formula (4) en donde Ra y Rb son como se definieron anteriormente en la presente; c) la conversion del compuesto de la formula (4) a un compuesto de la formula (5) vía una epoxidacion diastereoselectiva en donde Ra y cada Rb son como se definieron anteriormente; d) la reaccion de un compuesto de la formula (5) con un compuesto de la formula (6) en donde Y es OBn, Cl, Br o I, en presencia de una base de metal alcalino, para dar un compuesto de la formula (7) en donde cada Ra, cada Rb e Y son como se definieron anteriormente en la presente; y e) la conversi'n del compuesto de la formula (7) para dar un compuesto de la formula (1) vía la desililacion, en donde cada Rb e Y son como se definieron anteriormente en la presente. Reivindicacion 17: Un compuesto intermediario caracterizado porquie es seleccionado del grupo que consiste de formulas 1b, 2, 1d, 1e, 3, 4, 5, 7, 8, 9 y 10; en donde Ra es alilo, femnilo o fenilo sustituido con uno, dos o tres grupos alquilo C1-4 o alcoxi C1-4; y cada Rb, en cada aparicion es independientemente alquilo C1-4; cada Rc, en cada aparicion es independientemente H o Bn, y cada Y, en cada aparicion es independientemente OBn, Cl, Br, o I.The processes for the preparation of entecavir and the new intermediaries thereof, using carbon-silicon oxidation. Chemical compositions Claim 3: A process for the preparation of a compound of the formula (1) wherein each Rb is C1-4 alkyl, and Y is OBn, Cl, Br or I; characterized in that it comprises: a) the reaction of a compound of the formula (2) wherein each Rb is as defined hereinbefore, with RaSi halide (Rb) 2, where Ra is allyl, phenyl or substituted phenyl with one two or three C1-4 alkyls or C1-4 alkoxy; and each Rb is as defined hereinbefore; in the presence of a base to give a compound of the formula (3) wherein Ra and each Rb are as defined hereinbefore; b) deprotection of the PMB group in the compound of the formula (3) to give a compound of the formula (4) wherein Ra and Rb are as defined hereinbefore; c) the conversion of the compound of the formula (4) to a compound of the formula (5) via a diastereoselective epoxidation wherein Ra and each Rb are as defined above; d) the reaction of a compound of the formula (5) with a compound of the formula (6) wherein Y is OBn, Cl, Br or I, in the presence of an alkali metal base, to give a compound of the formula (7) where each Ra, each Rb and Y are as defined hereinbefore; and e) the conversion of the compound of the formula (7) to give a compound of the formula (1) via the desililation, wherein each Rb and Y are as defined hereinbefore. Claim 17: An intermediate compound characterized in that it is selected from the group consisting of formulas 1b, 2, 1d, 1e, 3, 4, 5, 7, 8, 9 and 10; wherein Ra is allyl, phemnyl or phenyl substituted with one, two or three C1-4 alkyl or C1-4 alkoxy groups; and each Rb, in each occurrence is independently C1-4 alkyl; each Rc, in each occurrence is independently H or Bn, and each Y, in each occurrence is independently OBn, Cl, Br, or I.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US57689904P | 2004-06-04 | 2004-06-04 |
Publications (1)
Publication Number | Publication Date |
---|---|
AR050339A1 true AR050339A1 (en) | 2006-10-18 |
Family
ID=37311738
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ARP050102291A AR050339A1 (en) | 2004-06-04 | 2005-06-03 | PROCESS FOR THE PREPARATION OF ENTECAVIR AND NEW INTERMEDIARIES OF THE SAME VIA CARBON-SILICON OXIDATION. |
Country Status (5)
Country | Link |
---|---|
CN (2) | CN1964972B (en) |
AR (1) | AR050339A1 (en) |
PE (1) | PE20060278A1 (en) |
TW (1) | TW200540175A (en) |
ZA (1) | ZA200610141B (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8481728B2 (en) * | 2010-02-16 | 2013-07-09 | Scinopharm Taiwan, Ltd. | Process for preparing entecavir and its intermediates |
TWI668220B (en) * | 2010-08-30 | 2019-08-11 | 浙江奧翔藥業股份有限公司 | Synthetic method of entecavir and intermediate compounds thereof |
CN102952135B (en) * | 2011-08-31 | 2015-04-08 | 南京工业大学 | Method for synthesizing hepatitis B medicine entecavir |
CN103304375B (en) * | 2012-03-12 | 2017-04-12 | 浙江奥翔药业股份有限公司 | Synthesis intermediate of Entecavir and preparation method thereof |
CN109232637B (en) * | 2018-10-29 | 2020-11-24 | 常州博海威医药科技股份有限公司 | Preparation method of entecavir intermediate |
Family Cites Families (3)
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 |
IN2012DN00604A (en) * | 2002-12-11 | 2015-08-21 | Bristol Myers Squibb Co |
-
2005
- 2005-06-01 TW TW094118021A patent/TW200540175A/en unknown
- 2005-06-03 CN CN2005800181523A patent/CN1964972B/en active Active
- 2005-06-03 CN CN200910203515.0A patent/CN101565359B/en active Active
- 2005-06-03 AR ARP050102291A patent/AR050339A1/en unknown
- 2005-06-06 PE PE2005000634A patent/PE20060278A1/en not_active Application Discontinuation
-
2006
- 2006-12-04 ZA ZA200610141A patent/ZA200610141B/en unknown
Also Published As
Publication number | Publication date |
---|---|
TW200540175A (en) | 2005-12-16 |
CN1964972B (en) | 2011-04-20 |
CN1964972A (en) | 2007-05-16 |
ZA200610141B (en) | 2008-09-25 |
PE20060278A1 (en) | 2006-04-20 |
CN101565359A (en) | 2009-10-28 |
CN101565359B (en) | 2013-05-29 |
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