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CN103443115A - 制备齐多夫定及其中间体的方法 - Google Patents

制备齐多夫定及其中间体的方法 Download PDF

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Publication number
CN103443115A
CN103443115A CN2011800025200A CN201180002520A CN103443115A CN 103443115 A CN103443115 A CN 103443115A CN 2011800025200 A CN2011800025200 A CN 2011800025200A CN 201180002520 A CN201180002520 A CN 201180002520A CN 103443115 A CN103443115 A CN 103443115A
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China
Prior art keywords
reaction
solvent
sodium
formula
reaction temperature
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CN2011800025200A
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English (en)
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CN103443115B (zh
Inventor
李金亮
赵楠
刘澍
程风华
熊玉友
周春峰
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Jiangsu Puxin Pharmaceutical Co ltd
Jiangxi Desino Pharmaceutical Co ltd
Shanghai Desano Pharmaceuticals Investment Co ltd
Shanghai Desano Chemical Pharmaceutical Co Ltd
Original Assignee
Jiangsu Puxin Pharmaceuticals Dev Co ltd
Shanghai Desano Pharmaceutical Investment Co ltd
Shanghai Desano Chemical Pharmaceutical Co Ltd
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Publication of CN103443115A publication Critical patent/CN103443115A/zh
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    • 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
    • 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
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Saccharide Compounds (AREA)

Abstract

本发明涉及一种制备齐多夫定(B)的方法，所述方法包括如下步骤：1）以2’-卤代胸苷(A)为原料，将其5’-位羟基进行保护，得到式（I）化合物；2）式（I）化合物脱卤得到式（II）化合物；3）式（II）化合物经3’-位羟基酰化保护得到式（III）化合物；4）式（III）化合物进行消除反应得到式（IV）化合物；5）式（IV）化合物经叠氮化反应得到式（V）化合物；6）式（V）化合物脱保护得到齐多夫定(B)；上述路线的反应式如(C)。式中，X为卤素；P1为羟基保护基；P2为C1-4烷基磺酰基、氟代的C1-4烷基磺酰基、芳基磺酰基或-CS-R，其中R为C1-4烷基。本发明还涉及通式(I)的中间体，其中X和P1的定义如上所述。

Description

PCT国内申请，说明书已公开。

Claims (12)

  1. PCT国内申请，权利要求书已公开。
CN201180002520.0A 2011-11-07 2011-11-07 制备齐多夫定及其中间体的方法 Active CN103443115B (zh)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CN2011/081853 WO2013067664A1 (zh) 2011-11-07 2011-11-07 制备齐多夫定及其中间体的方法

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CN103443115A true CN103443115A (zh) 2013-12-11
CN103443115B CN103443115B (zh) 2015-09-23

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WO (1) WO2013067664A1 (zh)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104844672A (zh) * 2015-04-09 2015-08-19 苏州华诺医药有限公司 制备齐多夫定及其中间体的方法
CN113461759A (zh) * 2021-07-02 2021-10-01 华东理工大学 基于连续流微反应技术合成齐多夫定叠氮化中间体的方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0292101A2 (en) * 1987-03-25 1988-11-23 The Wellcome Foundation Limited Process for the preparation of 3'-azido-3'-deoxythymidine and intermediates
EP0638586A2 (en) * 1993-08-04 1995-02-15 Ajinomoto Co., Inc. Nucleoside derivatives and methods for producing them
CN1216766A (zh) * 1998-10-06 1999-05-19 中国人民解放军第二军医大学 一种β-胸苷的制备方法
CN1453287A (zh) * 2002-04-25 2003-11-05 北京万全阳光医药科技有限公司 “一锅法”制备2，3`－脱水－5`－o－(特戊酰基)胸腺嘧啶脱氧核苷及其衍生物(氧桥物)的新方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0292101A2 (en) * 1987-03-25 1988-11-23 The Wellcome Foundation Limited Process for the preparation of 3'-azido-3'-deoxythymidine and intermediates
EP0638586A2 (en) * 1993-08-04 1995-02-15 Ajinomoto Co., Inc. Nucleoside derivatives and methods for producing them
CN1216766A (zh) * 1998-10-06 1999-05-19 中国人民解放军第二军医大学 一种β-胸苷的制备方法
CN1453287A (zh) * 2002-04-25 2003-11-05 北京万全阳光医药科技有限公司 “一锅法”制备2，3`－脱水－5`－o－(特戊酰基)胸腺嘧啶脱氧核苷及其衍生物(氧桥物)的新方法

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
GEORGY V SIDOROV，等: "The synthesis of some tritium-labeled terminators of DNA synthesis", 《JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS》 *
NAVEEN C. SRIVASTAV，等: "Antiviral Activity of Various 1-(2’-Deoxy-β-D-lyxofuranosyl)，1-(2’-Fluoro-β-D-xylofuranosyl)，1-(3’-Fluoro-β-D-arabinofuranosyl)，and 2’-Fluoro-2’，3’-didehydro-2’，3’-dideoxyribose Pyrimidine Nucleoside Analogues against Duck", 《J. MED. CHEM.》 *
刘世领，等: "齐多夫定的合成", 《中国医药工业杂志》 *

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Publication number Publication date
CN103443115B (zh) 2015-09-23
WO2013067664A1 (zh) 2013-05-16

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Address after: No. 1479, zhangheng Road, Pudong New Area, Shanghai, 201203

Patentee after: SHANGHAI DESANO PHARMACEUTICALS INVESTMENT Co.,Ltd.

Patentee after: SHANGHAI DESANO CHEMICAL PHARMACEUTICAL Co.,Ltd.

Patentee after: JIANGSU PUXIN PHARMACEUTICAL Co.,Ltd.

Address before: No. 1479, zhangheng Road, Pudong New Area, Shanghai, 201203

Patentee before: SHANGHAI DESANO PHARMACEUTICALS INVESTMENT Co.,Ltd.

Patentee before: SHANGHAI DESANO CHEMICAL PHARMACEUTICAL Co.,Ltd.

Patentee before: JIANGSU PUXIN PHARMACEUTICALS DEVELOPMENT Co.,Ltd.

CP01 Change in the name or title of a patent holder
TR01 Transfer of patent right

Effective date of registration: 20211223

Address after: 331299 Zhangshu salt chemical industrial base, Yichun City, Jiangxi Province

Patentee after: Jiangxi desino Pharmaceutical Co.,Ltd.

Patentee after: SHANGHAI DESANO PHARMACEUTICALS INVESTMENT Co.,Ltd.

Address before: No. 1479, zhangheng Road, Pudong New Area, Shanghai, 201203

Patentee before: SHANGHAI DESANO PHARMACEUTICALS INVESTMENT Co.,Ltd.

Patentee before: SHANGHAI DESANO CHEMICAL PHARMACEUTICAL Co.,Ltd.

Patentee before: JIANGSU PUXIN PHARMACEUTICAL Co.,Ltd.

TR01 Transfer of patent right