AR073003A1 - Proceso para preparar 5-azacitosina nucleosidos y sus derivados - Google Patents

Proceso para preparar 5-azacitosina nucleosidos y sus derivados

Info

Publication number
AR073003A1
AR073003A1 ARP090103079A ARP090103079A AR073003A1 AR 073003 A1 AR073003 A1 AR 073003A1 AR P090103079 A ARP090103079 A AR P090103079A AR P090103079 A ARP090103079 A AR P090103079A AR 073003 A1 AR073003 A1 AR 073003A1
Authority
AR
Argentina
Prior art keywords
azacytosine
formula
nucleoside
hydrogen
silylated
Prior art date
Application number
ARP090103079A
Other languages
English (en)
Inventor
Julian Paul Henschke
Xiaoheng Zhang
Lunghu Wang
Yung Fa Chen
Original Assignee
Scinopharm Taiwan Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Scinopharm Taiwan Ltd filed Critical Scinopharm Taiwan Ltd
Publication of AR073003A1 publication Critical patent/AR073003A1/es

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/12—Triazine radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • 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
    • C07H13/04—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 attached to acyclic carbon atoms
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
    • A61L2300/416—Anti-neoplastic or anti-proliferative or anti-restenosis or anti-angiogenic agents, e.g. paclitaxel, sirolimus

Abstract

Un proceso para sintetizar un nucleosido de 5-azacitosina, tal como azacitidina y decitabina, que comprende acoplar una 5-azacitosina sililada con una D-ribofuranosa en la presencia de un catalizador de ácido sulfonico. Reivindicacion 1: Un proceso para preparar un compuesto que es un nucleosido de 5-azacitosina de formula (1) donde R1 es hidrogeno, hidroxilo o halogeno; R2 es hidrogeno o halogeno; caracterizado porque comprende a) hacer reaccionar 5-azacitosina con un agente sililante para producir una mezcla de reaccion que contiene una 5-azacitosina sililada de formula (2) donde cada uno de R3 es independientemente un grupo alquilo C1-20 o un grupo arilo opcionalmente sustituido; b) unir la 5-azacitosina sililada de formula (2) con una D-ribofuranosa protegida de formula (3) donde R1' es hidrogeno, halogeno o OR4; R4 representa un grupo protector de hidroxilo; en un primer solvente orgánico y en presencia de un catalizador de ácido sulfonico, para obtener una solucion de un nucleosido de 5-azacitosina protegido de formula (4) donde cada uno de R5 y R6 es independientemente hidrogeno o Si(R3)3, R3 es un grupo alquilo C1-20 o un grupo arilo opcionalmente sustituido y R1' y R2 son como se los definio con anterioridad; y c) convertir el nucleosido de 5-azacitosina protegido de formula (4) en el nucleosido de 5-azacitosina de formula (1).
ARP090103079A 2008-08-08 2009-08-10 Proceso para preparar 5-azacitosina nucleosidos y sus derivados AR073003A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US18843108P 2008-08-08 2008-08-08

Publications (1)

Publication Number Publication Date
AR073003A1 true AR073003A1 (es) 2010-10-06

Family

ID=41653537

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP090103079A AR073003A1 (es) 2008-08-08 2009-08-10 Proceso para preparar 5-azacitosina nucleosidos y sus derivados

Country Status (11)

Country Link
US (1) US8212021B2 (es)
EP (1) EP2318423B1 (es)
JP (1) JP5650643B2 (es)
KR (1) KR101660549B1 (es)
CN (1) CN102216315B (es)
AR (1) AR073003A1 (es)
AU (1) AU2009279461B2 (es)
CA (1) CA2733591C (es)
ES (1) ES2487525T3 (es)
IL (1) IL211100A (es)
WO (1) WO2010017547A1 (es)

Families Citing this family (20)

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Publication number Priority date Publication date Assignee Title
US6887855B2 (en) * 2003-03-17 2005-05-03 Pharmion Corporation Forms of 5-azacytidine
US6943249B2 (en) * 2003-03-17 2005-09-13 Ash Stevens, Inc. Methods for isolating crystalline Form I of 5-azacytidine
EP3782611B1 (en) * 2008-05-15 2022-07-06 Celgene Corporation Oral formulations of cytidine analogs and methods of use thereof
IT1399195B1 (it) 2010-03-30 2013-04-11 Chemi Spa Processo per la sintesi di azacitidina e decitabina
KR101241321B1 (ko) * 2010-08-05 2013-03-11 케이피엑스 라이프사이언스 주식회사 수율 및 순도가 개선된 데시타빈의 제조방법
CN101974051B (zh) * 2010-10-08 2012-08-08 重庆泰濠制药有限公司 一种阿扎胞苷的合成方法
JP6289361B2 (ja) * 2011-03-31 2018-03-07 セルジーン インターナショナル サルル ５−アザシチジンの合成
CN102702292B (zh) * 2012-05-20 2015-04-29 湖州展望药业有限公司 一种阿扎胞苷的制备方法
CN103524584A (zh) * 2012-07-05 2014-01-22 天津九海医药科技有限公司 一种阿扎胞苷的合成方法
CN102911229B (zh) * 2012-10-30 2014-01-29 浙江先锋科技有限公司 一种1-β-D-呋喃核糖基胞嘧啶的制备方法
BR112015025716A2 (pt) 2013-04-12 2017-07-18 Achillion Pharmaceuticals Inc pró-fármacos de nucleosídeo submetidos a deutério úteis para o tratamento de hcv
CN103193842A (zh) * 2013-04-23 2013-07-10 济宁高新技术开发区永丰化工厂 卡培他滨的合成方法
CN103275158A (zh) * 2013-06-17 2013-09-04 江苏红豆杉药业有限公司 一种制备地西他滨的方法
CN104672289A (zh) * 2013-11-29 2015-06-03 南京圣和药业股份有限公司 一种阿扎胞苷杂质的制备方法
CN106117290A (zh) * 2016-06-27 2016-11-16 青岛云天生物技术有限公司 一种抗癌药物地西他滨的制备方法
CN108226309B (zh) 2016-12-13 2020-06-16 江苏奥赛康药业有限公司 一种右丙亚胺的分析方法
CN106831917B (zh) * 2016-12-21 2020-05-19 连云港恒运药业有限公司 地西他滨中间体的制备方法
CN108239128B (zh) * 2016-12-23 2019-03-29 江苏奥赛康药业股份有限公司 β-核苷类化合物的制备方法
CN112279881A (zh) * 2020-10-12 2021-01-29 福建南方制药股份有限公司 一种制备抗肿瘤药物阿扎胞苷的方法
CN113201039B (zh) * 2021-05-19 2022-04-29 南京德克瑞医药化工有限公司 一种医药中间体2’,3’,5’-三乙酰阿扎胞苷的制备方法

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1050899A (es) 1963-12-22
CH527207A (de) 1968-05-08 1972-08-31 Ceskoslovenska Akademie Ved Verfahren zur Herstellung von 1-Glycosyl-5-azacytosinen
DE2012888C3 (de) 1970-03-14 1981-04-02 Schering Ag, 1000 Berlin Und 4619 Bergkamen Verfahren zur Herstellung von 5-Azapyrimidinnucleosiden
DE2508312A1 (de) 1975-02-24 1976-09-02 Schering Ag Neues verfahren zur herstellung von nucleosiden
DE2757365A1 (de) 1977-12-20 1979-06-21 Schering Ag Neues verfahren zur herstellung von nucleosiden
US6943249B2 (en) 2003-03-17 2005-09-13 Ash Stevens, Inc. Methods for isolating crystalline Form I of 5-azacytidine
US7038038B2 (en) 2003-03-17 2006-05-02 Pharmion Corporation Synthesis of 5-azacytidine
US6887855B2 (en) 2003-03-17 2005-05-03 Pharmion Corporation Forms of 5-azacytidine
EP2048151A1 (en) 2007-10-10 2009-04-15 Cilag AG Method for producing nucleosides by direct glycosylation of the nucleoside base
CN101148465A (zh) * 2007-11-01 2008-03-26 上海交通大学 3-苄基-l-尿嘧啶核苷及其制备方法
WO2010014883A2 (en) 2008-08-01 2010-02-04 Dr. Reddy's Laboratories Ltd. Azacitidine process and polymorphs

Also Published As

Publication number Publication date
CA2733591C (en) 2016-06-28
CN102216315B (zh) 2016-06-29
US20100036112A1 (en) 2010-02-11
US8212021B2 (en) 2012-07-03
CN102216315A (zh) 2011-10-12
ES2487525T3 (es) 2014-08-21
EP2318423A4 (en) 2013-01-02
IL211100A0 (en) 2011-04-28
EP2318423A1 (en) 2011-05-11
EP2318423B1 (en) 2014-05-07
JP2011530538A (ja) 2011-12-22
JP5650643B2 (ja) 2015-01-07
IL211100A (en) 2013-06-27
AU2009279461B2 (en) 2014-01-23
WO2010017547A1 (en) 2010-02-11
WO2010017547A8 (en) 2011-07-28
CA2733591A1 (en) 2010-02-11
KR101660549B1 (ko) 2016-09-27
AU2009279461A1 (en) 2010-02-11
KR20110048551A (ko) 2011-05-11

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