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AR052860A1 - Intermediario y proceso para preparar anomeros beta-enriquecidos de 21-deoxi,21, 21-difluoro-d-ribofuranosil nucleosidos - Google Patents

Intermediario y proceso para preparar anomeros beta-enriquecidos de 21-deoxi,21, 21-difluoro-d-ribofuranosil nucleosidos

Info

Publication number
AR052860A1
AR052860A1 ARP050105638A ARP050105638A AR052860A1 AR 052860 A1 AR052860 A1 AR 052860A1 AR P050105638 A ARP050105638 A AR P050105638A AR P050105638 A ARP050105638 A AR P050105638A AR 052860 A1 AR052860 A1 AR 052860A1
Authority
AR
Argentina
Prior art keywords
formula
compound
beta
gemcitabine
anomer
Prior art date
Application number
ARP050105638A
Other languages
English (en)
Inventor
Deependra Bhatt
Bijan K Panda
Golak C Maikap
Original Assignee
Dabur Pharma 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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=35457749&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=AR052860(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Dabur Pharma Ltd filed Critical Dabur Pharma Ltd
Publication of AR052860A1 publication Critical patent/AR052860A1/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
    • C07H19/06—Pyrimidine radicals
    • C07H19/073—Pyrimidine radicals with 2-deoxyribosyl as the saccharide radical
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Reivindicacion 1: Un compuesto de la formula (1), caracterizado porque P es hidrogeno o un grupo protector hidroxi. Reivindicacion 3: Un proceso para la preparacion del compuesto de la formula (1) caracterizado porque comprende hacer reaccionar un compuesto de lactol de la formula (2), donde P es como se definio precedentemente con tricloroacetonitrilo en un solvente orgánico inerte y en presencia de una base. Reivindicacion 10: Un proceso de glicosilacion estereoselectiva para preparar más de 99% de anomero beta-enriquecido de clorhidrato de gemcitabina de la formula (3), caracterizado porque comprende los pasos de: a) glicosilar un compuesto de la formula (1), donde P es como se definio precedentemente con la citosina de la formula (4) o (5), donde R4 es un grupo protector nitrogeno y R5 es un grupo protector hidroxi en presencia de un solvente orgánico inerte y opcionalmente en presencia de un catalizador de ácido de Lewis a la base libre de gemcitabina protegida de la formula (6), donde P y R4 son como se definio precedentemente; b) eliminar dichos grupos protectores mediante el tratamiento del compuesto de la formula (6) con amoníaco acuoso en presencia de un alcohol C1-3 o con resinas de intercambio anionico con iones hidroxi intercambiados para dar el anomero beta-enriquecido de la base libre de gemcitabina de la formula (7); c) contactar la base libre de gemcitabina de la formula (7) obtenida de esta manera con cloruro de hidrogeno en un alcohol C1-3 para dar el anomero beta-enriquecido de clorhidrato de gemcitabina de la formula (3) con una pureza de mayor igual 95%, preferentemente mayor igual 95%; y d) opcionalmente enriquecer adicionalmente el contenido de anomero beta del clorhidrato de gemcitabina de la formula (3) hasta más del 99% mediante la cristalizacion de una mezcla de un ácido orgánico alifático C2-3 y agua.
ARP050105638A 2005-03-04 2005-12-29 Intermediario y proceso para preparar anomeros beta-enriquecidos de 21-deoxi,21, 21-difluoro-d-ribofuranosil nucleosidos AR052860A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IN472DE2005 2005-03-04

Publications (1)

Publication Number Publication Date
AR052860A1 true AR052860A1 (es) 2007-04-04

Family

ID=35457749

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP050105638A AR052860A1 (es) 2005-03-04 2005-12-29 Intermediario y proceso para preparar anomeros beta-enriquecidos de 21-deoxi,21, 21-difluoro-d-ribofuranosil nucleosidos

Country Status (24)

Country Link
US (2) US7235647B2 (es)
EP (1) EP1853616B1 (es)
JP (1) JP2008531680A (es)
KR (1) KR20070112774A (es)
CN (1) CN101203524B (es)
AP (1) AP2219A (es)
AR (1) AR052860A1 (es)
AT (1) ATE458743T1 (es)
AU (1) AU2005328519B2 (es)
BR (1) BRPI0520050A2 (es)
CA (1) CA2598895A1 (es)
CL (1) CL2005003456A1 (es)
DE (1) DE602005019626D1 (es)
EA (1) EA011558B1 (es)
ES (1) ES2341663T3 (es)
GE (1) GEP20094822B (es)
IL (1) IL184957A (es)
MX (1) MX2007010316A (es)
MY (1) MY141378A (es)
NZ (1) NZ560735A (es)
TW (1) TWI333493B (es)
UA (1) UA88940C2 (es)
WO (1) WO2006092808A1 (es)
ZA (1) ZA200706392B (es)

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EA011558B1 (ru) * 2005-03-04 2009-04-28 Дабур Фарма Лимитед ПРОМЕЖУТОЧНОЕ СОЕДИНЕНИЕ И СПОСОБ ПОЛУЧЕНИЯ ОБОГАЩЕННЫХ β-АНОМЕРОМ 2-ДЕЗОКСИ-2,2-ДИФТОР-D-РИБОФУРАНОЗИЛНУКЛЕОЗИДОВ
WO2008026222A2 (en) * 2006-08-28 2008-03-06 Shilpa Medicare Ltd Process and intermediates of 2,2' difluoronucleosides
KR100846143B1 (ko) 2007-02-28 2008-07-14 (주) 유일팜테크 2'-데옥시-2',2'-디플루오로시티딘의 전구체 및 그의제조방법
CN102093451A (zh) * 2009-12-12 2011-06-15 上海华理生物医药有限公司 一种制备吉西他滨中间体的方法
CN102153601A (zh) * 2011-02-26 2011-08-17 湖南欧亚生物有限公司 一种高选择性的制备盐酸吉西他滨以及其中间体的方法
CN102603838B (zh) * 2012-02-14 2015-02-18 江苏八巨药业有限公司 一种制备吉西他滨盐酸盐的方法
CN103232508A (zh) * 2012-05-22 2013-08-07 湖北一半天制药有限公司 工业化盐酸吉西他滨的合成方法
EP3564207B1 (en) * 2016-12-28 2021-09-15 Kaneka Corporation Method for producing alcohol compound
BR112019022470A2 (pt) 2017-04-26 2020-05-12 I. Kalman Thomas Composto, composição, e, método para tratamento de um indivíduo com câncer.
CN107200757B (zh) * 2017-06-29 2020-06-02 上海泓博智源医药股份有限公司 一种桥环氟代酯及其制备方法和应用
CN110511258A (zh) * 2018-05-21 2019-11-29 中国科学院上海药物研究所 一种胞嘧啶核苷的制备方法
CN109796506A (zh) * 2019-01-28 2019-05-24 江苏八巨药业有限公司 一种吉西他滨关键中间体的制备方法
CN111909229B (zh) * 2020-08-12 2023-05-05 福建瑞博奥科技有限公司 一种β-烟酰胺核糖氯化物的制备方法

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CA1264738A (en) * 1984-12-04 1990-01-23 Eli Lilly And Company Treatment of tumors in mammals
ZA859008B (en) * 1984-12-04 1987-07-29 Lilly Co Eli The treatment of tumors in mammals
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CN101010329B (zh) * 2004-12-30 2011-06-08 韩美控股株式会社 2’-脱氧-2’,2'-二氟胞苷的制备方法
EA011558B1 (ru) * 2005-03-04 2009-04-28 Дабур Фарма Лимитед ПРОМЕЖУТОЧНОЕ СОЕДИНЕНИЕ И СПОСОБ ПОЛУЧЕНИЯ ОБОГАЩЕННЫХ β-АНОМЕРОМ 2-ДЕЗОКСИ-2,2-ДИФТОР-D-РИБОФУРАНОЗИЛНУКЛЕОЗИДОВ

Also Published As

Publication number Publication date
EA200701889A1 (ru) 2008-02-28
JP2008531680A (ja) 2008-08-14
UA88940C2 (ru) 2009-12-10
DE602005019626D1 (de) 2010-04-08
CN101203524B (zh) 2011-06-15
AP2219A (en) 2011-03-22
EP1853616B1 (en) 2010-02-24
US20070208170A1 (en) 2007-09-06
CA2598895A1 (en) 2006-09-08
AU2005328519A1 (en) 2006-09-08
CL2005003456A1 (es) 2008-05-02
US20060217547A1 (en) 2006-09-28
AP2007004098A0 (en) 2007-08-31
MY141378A (en) 2010-04-30
GEP20094822B (en) 2009-11-10
US7235647B2 (en) 2007-06-26
KR20070112774A (ko) 2007-11-27
EP1853616A1 (en) 2007-11-14
AU2005328519B2 (en) 2012-03-01
BRPI0520050A2 (pt) 2009-11-17
MX2007010316A (es) 2008-02-19
NZ560735A (en) 2009-07-31
IL184957A0 (en) 2007-12-03
ZA200706392B (en) 2008-09-25
ATE458743T1 (de) 2010-03-15
TW200643027A (en) 2006-12-16
IL184957A (en) 2011-06-30
CN101203524A (zh) 2008-06-18
ES2341663T3 (es) 2010-06-24
EA011558B1 (ru) 2009-04-28
TWI333493B (en) 2010-11-21
WO2006092808A1 (en) 2006-09-08

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