AR073003A1 - Proceso para preparar 5-azacitosina nucleosidos y sus derivados - Google Patents
Proceso para preparar 5-azacitosina nucleosidos y sus derivadosInfo
- 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
Links
- 238000000034 method Methods 0.000 title abstract 2
- -1 5-azacytosine nucleoside Chemical class 0.000 abstract 5
- 239000002777 nucleoside Substances 0.000 abstract 5
- MFEFTTYGMZOIKO-UHFFFAOYSA-N 5-azacytosine Chemical compound NC1=NC=NC(=O)N1 MFEFTTYGMZOIKO-UHFFFAOYSA-N 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 abstract 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract 2
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 abstract 2
- 239000003377 acid catalyst Substances 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- XAUDJQYHKZQPEU-KVQBGUIXSA-N 5-aza-2'-deoxycytidine Chemical compound O=C1N=C(N)N=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 XAUDJQYHKZQPEU-KVQBGUIXSA-N 0.000 abstract 1
- NMUSYJAQQFHJEW-KVTDHHQDSA-N 5-azacytidine Chemical compound O=C1N=C(N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NMUSYJAQQFHJEW-KVTDHHQDSA-N 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 229960002756 azacitidine Drugs 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 229960003603 decitabine Drugs 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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).
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)
| 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 |
| HUE042825T2 (hu) | 2008-05-15 | 2019-07-29 | Celgene Corp | Citidin-analógokat tartalmazó orális készítmények, és eljárás azok alkalmazására |
| 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 |
| EP2691408B1 (en) * | 2011-03-31 | 2017-06-28 | Celgene International SÁRL | Synthesis of 5-azacytidine |
| 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 |
| KR20160002896A (ko) | 2013-04-12 | 2016-01-08 | 아칠리온 파르마세우티칼스 인코포레이티드 | Ｈｃｖ를 치료하는데 유용한 중수소화 뉴클레오시드 전구약물 |
| 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)
| 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 |
| 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 |
| US6943249B2 (en) | 2003-03-17 | 2005-09-13 | Ash Stevens, Inc. | Methods for isolating crystalline Form I 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 |
| EP2321302B1 (en) | 2008-08-01 | 2014-10-29 | Dr. Reddy's Laboratories Ltd. | Azacitidine process and polymorphs |
-
2009
- 2009-08-10 AR ARP090103079A patent/AR073003A1/es unknown
- 2009-08-10 JP JP2011522304A patent/JP5650643B2/ja active Active
- 2009-08-10 US US12/538,271 patent/US8212021B2/en active Active
- 2009-08-10 KR KR1020117005503A patent/KR101660549B1/ko not_active Expired - Fee Related
- 2009-08-10 AU AU2009279461A patent/AU2009279461B2/en not_active Ceased
- 2009-08-10 CA CA2733591A patent/CA2733591C/en active Active
- 2009-08-10 WO PCT/US2009/053276 patent/WO2010017547A1/en not_active Ceased
- 2009-08-10 EP EP09805656.7A patent/EP2318423B1/en active Active
- 2009-08-10 ES ES09805656.7T patent/ES2487525T3/es active Active
- 2009-08-10 CN CN200980136786.7A patent/CN102216315B/zh active Active
-
2011
- 2011-02-06 IL IL211100A patent/IL211100A/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| EP2318423A4 (en) | 2013-01-02 |
| WO2010017547A8 (en) | 2011-07-28 |
| CA2733591C (en) | 2016-06-28 |
| AU2009279461A1 (en) | 2010-02-11 |
| CA2733591A1 (en) | 2010-02-11 |
| EP2318423B1 (en) | 2014-05-07 |
| JP2011530538A (ja) | 2011-12-22 |
| WO2010017547A1 (en) | 2010-02-11 |
| KR101660549B1 (ko) | 2016-09-27 |
| AU2009279461B2 (en) | 2014-01-23 |
| CN102216315A (zh) | 2011-10-12 |
| CN102216315B (zh) | 2016-06-29 |
| JP5650643B2 (ja) | 2015-01-07 |
| EP2318423A1 (en) | 2011-05-11 |
| IL211100A0 (en) | 2011-04-28 |
| US8212021B2 (en) | 2012-07-03 |
| US20100036112A1 (en) | 2010-02-11 |
| IL211100A (en) | 2013-06-27 |
| ES2487525T3 (es) | 2014-08-21 |
| KR20110048551A (ko) | 2011-05-11 |
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Legal Events
| Date | Code | Title | Description |
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| FB | Suspension of granting procedure |