WO2004082618A3 - Synthesis of 5-azacytidine - Google Patents

Synthesis of 5-azacytidine Download PDF

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Publication number
WO2004082618A3
WO2004082618A3 PCT/US2004/007894 US2004007894W WO2004082618A3 WO 2004082618 A3 WO2004082618 A3 WO 2004082618A3 US 2004007894 W US2004007894 W US 2004007894W WO 2004082618 A3 WO2004082618 A3 WO 2004082618A3
Authority
WO
WIPO (PCT)
Prior art keywords
azacytidine
synthesis
azacytosine
coupling
silylation
Prior art date
Application number
PCT/US2004/007894
Other languages
French (fr)
Other versions
WO2004082618A2 (en
Inventor
Dumitru Ionescu
Peter Blumbergs
Original Assignee
Ash Stevens Inc
Dumitru Ionescu
Peter Blumbergs
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 Ash Stevens Inc, Dumitru Ionescu, Peter Blumbergs filed Critical Ash Stevens Inc
Publication of WO2004082618A2 publication Critical patent/WO2004082618A2/en
Publication of WO2004082618A3 publication Critical patent/WO2004082618A3/en

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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

Abstract

The present invention provides a method for the preparation of 5-azacytidine, wherein 5-azacytidine is represented by the structure: The method involves the silylation of 5-azacytosine, followed by the coupling of silylated 5-azacytosine to a protected β-D-ribofuranose derivative. The coupling reaction is catalyzed by trimethylsilyl trifluoromethanesulfonate (TMS-Triflate).
PCT/US2004/007894 2003-03-17 2004-03-16 Synthesis of 5-azacytidine WO2004082618A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US10/390,526 2003-03-17
US10/390,526 US7038038B2 (en) 2003-03-17 2003-03-17 Synthesis of 5-azacytidine

Publications (2)

Publication Number Publication Date
WO2004082618A2 WO2004082618A2 (en) 2004-09-30
WO2004082618A3 true WO2004082618A3 (en) 2004-12-29

Family

ID=32987548

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2004/007894 WO2004082618A2 (en) 2003-03-17 2004-03-16 Synthesis of 5-azacytidine

Country Status (2)

Country Link
US (5) US7038038B2 (en)
WO (1) WO2004082618A2 (en)

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US6887855B2 (en) * 2003-03-17 2005-05-03 Pharmion Corporation Forms of 5-azacytidine
US8883790B2 (en) 2006-10-12 2014-11-11 Astex Therapeutics Limited Pharmaceutical combinations
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CN101311184B (en) * 2007-05-25 2011-05-04 上海医药工业研究院 2-deoxy-D-ribose derivates, preparation method and use thereof
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CN101821278B (en) * 2008-01-03 2012-03-28 南京华狮化工有限公司 Synthesis method of decitabine
SI2299984T1 (en) 2008-05-15 2019-04-30 Celgene Corporation Oral formulations of cytidine analogs and methods of use thereof
EP2321302B1 (en) * 2008-08-01 2014-10-29 Dr. Reddy's Laboratories Ltd. Azacitidine process and polymorphs
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US8212021B2 (en) * 2008-08-08 2012-07-03 Scinopharm Taiwan, Ltd. Process for making 5-azacytosine nucleosides and their derivatives
US8586729B2 (en) * 2008-10-03 2013-11-19 Scinopharm Taiwan Ltd. Synthesis of decitabine
CA2755976C (en) 2009-03-23 2020-04-07 Ambit Biosciences Corporation Methods of treatment using combination therapy
US20100249394A1 (en) * 2009-03-26 2010-09-30 Albemarle Corporation Processes for producing decitabine
AR076418A1 (en) * 2009-04-27 2011-06-08 Reddys Lab Inc Dr DECITABIN PREPARATION
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AU2012236476A1 (en) 2011-03-31 2013-05-02 Celgene International Sarl Systhesis of 5-azacytidine
CN102850418B (en) * 2011-06-30 2016-01-06 杭州容立医药科技有限公司 A kind of crystallization and drying means preparing high purity azacitidine
WO2013022872A1 (en) 2011-08-10 2013-02-14 Celgene Corporation Gene methylation biomarkers and methods of use thereof
EP2758067A1 (en) 2011-09-23 2014-07-30 Celgene Corporation Romidepsin and 5 - azacitidine for use in treating lymphoma
US20130244950A1 (en) 2011-09-26 2013-09-19 Celgene Corporation Combination therapy for chemoresistant cancers
CA2853949A1 (en) 2011-11-01 2013-05-10 Celgene Corporation Methods for treating cancers using oral formulations of cytidine analogs
EA028462B1 (en) 2012-02-24 2017-11-30 СИГНАЛ ФАРМАСЬЮТИКАЛЗ, ЭлЭлСи Methods for treating advanced non-small cell lung cancer using tor kinase inhibitor combination therapy
JP6042527B2 (en) 2012-04-04 2016-12-14 ハロザイム インコーポレイテッド Combination treatment of anti-hyaluronan and tumor-targeted taxane
CN102702292B (en) * 2012-05-20 2015-04-29 湖州展望药业有限公司 Preparation method of azacitidine
CN103524584A (en) * 2012-07-05 2014-01-22 天津九海医药科技有限公司 Synthetic method of azacitidine
US9968627B2 (en) 2013-03-26 2018-05-15 Celgene Corporation Solid forms comprising 4-amino-1-β-D-ribofuranosyl-1,3,5-triazin-2(1H)-one and a coformer, compositions and methods of use thereof
EP3055009B1 (en) 2013-10-10 2018-12-19 Medical Components, Inc. Huber needle assembly with safety capture device
CN104672289A (en) * 2013-11-29 2015-06-03 南京圣和药业股份有限公司 Preparation method of azacitidine impurity
US20150359810A1 (en) 2014-06-17 2015-12-17 Celgene Corporation Methods for treating epstein-barr virus (ebv) associated cancers using oral formulations of 5-azacytidine
US10478566B2 (en) 2014-08-29 2019-11-19 Medical Components, Inc. Huber safety needle
USD804021S1 (en) 2015-02-27 2017-11-28 Medical Components, Inc. Huber safety needle
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AU2016338557B2 (en) 2015-10-15 2022-05-26 Celgene Corporation Combination therapy for treating malignancies
EP3362070B1 (en) 2015-10-15 2021-01-27 Celgene Corporation Combination of a mutant isocitrate dehydrogenase 2 inhibitor with azacitidine and its use for treating acute myelogenous leukemia
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CN109651451B (en) * 2017-10-10 2023-07-11 芜湖先声中人药业有限公司 Azacitidine derivative preparation method and application thereof
US20190351031A1 (en) 2018-05-16 2019-11-21 Halozyme, Inc. Methods of selecting subjects for combination cancer therapy with a polymer-conjugated soluble ph20
CN112300222B (en) * 2020-11-26 2023-03-21 北京益佰医药研究有限公司 Azacitidine refining method with high purity and low solvent residue

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US7038038B2 (en) * 2003-03-17 2006-05-02 Pharmion Corporation Synthesis of 5-azacytidine

Patent Citations (2)

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Publication number Priority date Publication date Assignee Title
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US6642206B2 (en) * 1996-10-16 2003-11-04 Icn Pharmaceuticals, Inc. Monocyclic L-nucleosides, analogs and uses thereof

Also Published As

Publication number Publication date
US20060247432A1 (en) 2006-11-02
US7038038B2 (en) 2006-05-02
US7858774B2 (en) 2010-12-28
US8058424B2 (en) 2011-11-15
US20120029181A1 (en) 2012-02-02
US20090005551A1 (en) 2009-01-01
US20040186283A1 (en) 2004-09-23
WO2004082618A2 (en) 2004-09-30
US20110092694A1 (en) 2011-04-21

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