AR001041A1 - Procedimiento para preparar clorhidrato de 1-(2'-desoxi-2'2'-difluoro-d-ribofuranosil)-4-aminopirimidin-2-ona - Google Patents
Procedimiento para preparar clorhidrato de 1-(2'-desoxi-2'2'-difluoro-d-ribofuranosil)-4-aminopirimidin-2-onaInfo
- Publication number
- AR001041A1 AR001041A1 AR33407495A AR33407495A AR001041A1 AR 001041 A1 AR001041 A1 AR 001041A1 AR 33407495 A AR33407495 A AR 33407495A AR 33407495 A AR33407495 A AR 33407495A AR 001041 A1 AR001041 A1 AR 001041A1
- Authority
- AR
- Argentina
- Prior art keywords
- ribofuranosyl
- deoxy
- difluoro
- hydrochloride
- prepare
- Prior art date
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 abstract 2
- 229960005144 gemcitabine hydrochloride Drugs 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- -1 1- (2-deoxy-2,2-difluoro-D-ribofuranosyl) -4-aminopyridin-2-one hydrochloride Chemical compound 0.000 abstract 1
- 150000003973 alkyl amines Chemical class 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 230000000903 blocking effect Effects 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000007717 exclusion Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07H19/06—Pyrimidine radicals
-
- 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)
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Se proporciona un procedimiento para preparar clorhidrato de 1-(2-desoxi-2,2-difluoro-D-ribofuranosil)-4-aminopiridin-2-ona clorhidratode gemcitabina de fórmula (I), separando los grupos benzoilo de bloqueo de compuestos debeta-1-(2-desoxi-2,2-difluoro-3,5-di-O-benzoil-D-ribofuranosil)-4- aminopirimidina-2-ona en presencia de cantidades catalíticas de alquilaminas,enun medio solvente de metanol o etanol, bajo exclusión de agua. El clorhidrato gemcitabina se recuperatratando la solución formada con ácido clorhídrico y unantisolvente.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/355,372 US5637688A (en) | 1994-12-13 | 1994-12-13 | Process for preparing 1-(2'-deoxy-2'-difluoro-d-ribofuranosyl)-4-aminopyrimidin-2-one hydrochloride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR001041A1 true AR001041A1 (es) | 1997-09-24 |
Family
ID=23397211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AR33407495A AR001041A1 (es) | 1994-12-13 | 1995-11-01 | Procedimiento para preparar clorhidrato de 1-(2'-desoxi-2'2'-difluoro-d-ribofuranosil)-4-aminopirimidin-2-ona |
Country Status (31)
| Country | Link |
|---|---|
| US (2) | US5637688A (es) |
| EP (1) | EP0719788B1 (es) |
| JP (1) | JPH10510806A (es) |
| KR (1) | KR100424991B1 (es) |
| CN (1) | CN1047177C (es) |
| AR (1) | AR001041A1 (es) |
| AT (1) | ATE179986T1 (es) |
| AU (1) | AU689674B2 (es) |
| BG (1) | BG62738B1 (es) |
| BR (1) | BR9509979A (es) |
| CO (1) | CO4520286A1 (es) |
| CZ (1) | CZ290941B6 (es) |
| DE (1) | DE69509624T2 (es) |
| DK (1) | DK0719788T3 (es) |
| ES (1) | ES2130542T3 (es) |
| GR (1) | GR3030265T3 (es) |
| HU (1) | HU219021B (es) |
| IL (1) | IL115852A (es) |
| MY (1) | MY112488A (es) |
| NO (1) | NO306783B1 (es) |
| NZ (1) | NZ296476A (es) |
| PE (1) | PE49296A1 (es) |
| PL (1) | PL181732B1 (es) |
| RO (1) | RO117327B1 (es) |
| RU (1) | RU2154648C2 (es) |
| SI (1) | SI0719788T1 (es) |
| TW (1) | TW379226B (es) |
| UA (1) | UA48152C2 (es) |
| WO (1) | WO1996018637A1 (es) |
| YU (1) | YU49314B (es) |
| ZA (1) | ZA959320B (es) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5637688A (en) * | 1994-12-13 | 1997-06-10 | Eli Lilly And Company | Process for preparing 1-(2'-deoxy-2'-difluoro-d-ribofuranosyl)-4-aminopyrimidin-2-one hydrochloride |
| EP0870506A1 (en) * | 1997-04-11 | 1998-10-14 | Eli Lilly And Company | Compositions comprising a cryptophycin compound in combination with a synchronizing or activating agent for treating cancer |
| JP4502503B2 (ja) * | 1997-12-22 | 2010-07-14 | シェーリング コーポレイション | 増殖性の疾患を処置するためのベンゾシクロヘプタピリジン化合物および抗腫瘍剤の組合せ |
| US6376470B1 (en) | 1999-09-23 | 2002-04-23 | Enzon, Inc. | Polymer conjugates of ara-C and ara-C derivatives |
| WO2002028387A1 (en) * | 2000-10-03 | 2002-04-11 | Oncopharmaceutical, Inc. | Inhibitors of angiogenesis and tumor growth for local and systemic administration |
| WO2005014010A1 (en) * | 2003-07-24 | 2005-02-17 | Eli Lilly And Company | Pharmaceutical composition comprising gemcitabine and cyclodextrines |
| US7214791B2 (en) * | 2004-07-01 | 2007-05-08 | Shenzhen Hande Technology Co., Ltd. | Method for preparation of 2′-deoxy-2′, 2′-difluoro-β-cytidine or pharmaceutically acceptable salts thereof by using 1,6-anhydro-β-d-glucose as raw material |
| TW200606159A (en) * | 2004-07-30 | 2006-02-16 | Pharmaessentia Corp | Stereoselective synthesis of β-nucleosides |
| WO2006070985A1 (en) * | 2004-12-30 | 2006-07-06 | Hanmi Pharm. Co., Ltd. | METHOD FOR THE PREPARATION OF 2#-DEOXY-2#,2#-DIFLUOROCYTIDINE |
| MX2007010316A (es) * | 2005-03-04 | 2008-02-19 | Dabur Pharma Ltd | Intermediario de 21-desoxi, 21,21-difluoro-d-ribofuranosil nucleosidos enriquecidos en (-anomero y proceso para prepararlo. |
| WO2006095359A1 (en) * | 2005-03-10 | 2006-09-14 | Sms Pharmaceuticals Limited | Synthesis of 2-deoxy-2, 2-di fluoro-d-ribo furanose-3, 5 di(4-methy/4-nitro-chloro)benzoate and its conversion to gemcitabine hydrochloride thereof |
| US7485716B2 (en) * | 2005-05-02 | 2009-02-03 | Pharmaessentia Corp. | Stereoselective synthesis of β-nucleosides |
| CN100391966C (zh) * | 2005-06-17 | 2008-06-04 | 华东师范大学 | 一种2’-脱氧-2’,2’-二氟-胞苷合成的方法 |
| EP1940859A1 (en) | 2005-10-28 | 2008-07-09 | Arch Pharmalabs Limited | An improved process for preparation of gemcitabine hydrochloride |
| KR101259637B1 (ko) * | 2005-12-14 | 2013-04-30 | 주식회사종근당 | 1-(2´-데옥시-2´,2´-디플루오로-디-리보푸라노실)-4-아미노피리미딘-2-온또는 그의 염산염의 제조방법 |
| RU2345087C2 (ru) * | 2006-02-06 | 2009-01-27 | Др. Редди`С Лабораторис Лтд. | Способ получения и очистки гемцитабина гидрохлорида |
| CN101600725B (zh) * | 2006-10-10 | 2014-11-26 | 吉利德制药有限责任公司 | 制备呋喃核糖基嘧啶核苷 |
| US20090069354A1 (en) * | 2007-09-12 | 2009-03-12 | Protia, Llc | Deuterium-enriched gemcitabine |
| JO2778B1 (en) | 2007-10-16 | 2014-03-15 | ايساي انك | Certain Compounds, Compositions and Methods |
| JP2011503093A (ja) * | 2007-11-06 | 2011-01-27 | ファーマエッセンティア コーポレイション | β−ヌクレオシドの新規な合成 |
| IT1393062B1 (it) * | 2008-10-23 | 2012-04-11 | Prime Europ Therapeuticals | Procedimento per la preparazione di gemcitabina cloridrato |
| WO2010118013A1 (en) * | 2009-04-06 | 2010-10-14 | Eisai Inc. | Combination of cytidine-based antineoplastic drugs with cytidine deaminase inhibitor and use thereof in the treatment of cancer |
| CA2757743C (en) * | 2009-04-06 | 2017-10-10 | Eisai Inc. | (2'-deoxy-ribofuranosyl)-1,3,4,7-tetrahydro-(1,3) diazepin-2-0ne derivatives for treating cancer |
| US8609631B2 (en) | 2009-04-06 | 2013-12-17 | Eisai Inc. | Compositions and methods for treating cancer |
| AR076263A1 (es) * | 2009-04-06 | 2011-06-01 | Eisai Inc | Composiciones y metodos para tratar cancer. uso. |
| CN101525361B (zh) * | 2009-04-21 | 2010-11-17 | 济南圣鲁金药物技术开发有限公司 | 基于吉西他滨结构的前药及其合成方法及应用 |
| KR101414888B1 (ko) * | 2009-05-15 | 2014-07-03 | 데루타-후라이 화마 가부시키가이샤 | 1-(2'-시아노-2'-데옥시-β-D-아라비노푸라노실)시토신·1염산염의 신규 안정형 결정 |
| CN101628927B (zh) * | 2009-08-07 | 2012-10-10 | 卡硼瑞(北京)科技有限公司 | 以1,3,5-三-O-苯甲酰基-α-D-呋喃核糖为原料立体选择性制备β-二氟胞苷盐酸盐的方法 |
| CN102453064B (zh) * | 2011-06-30 | 2014-07-09 | 江苏豪森药业股份有限公司 | 制备吉西他滨盐酸盐的方法 |
| CN102659884B (zh) * | 2012-04-23 | 2014-07-02 | 南京臣功制药股份有限公司 | 盐酸吉西他滨的提纯方法 |
| CN103224541B (zh) * | 2013-04-27 | 2015-07-01 | 江苏豪森药业股份有限公司 | 吉西他滨α-异构体转化回收工艺 |
| CN104402945A (zh) * | 2014-11-27 | 2015-03-11 | 苏州乔纳森新材料科技有限公司 | 一种3-脱氧-1,2-o-异丙叉-d-呋喃木糖的合成方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3817978A (en) * | 1971-06-16 | 1974-06-18 | Syntex Inc | 4-fluoro nucleosides and sugar intermediates, and methods of preparing |
| JPS5924999B2 (ja) * | 1978-06-10 | 1984-06-13 | 富山化学工業株式会社 | 新規な5−フルオロ−2′−デオキシ−β−ウリジン誘導体の製造法 |
| US4526988A (en) * | 1983-03-10 | 1985-07-02 | Eli Lilly And Company | Difluoro antivirals and intermediate therefor |
| CA1264738A (en) * | 1984-12-04 | 1990-01-23 | Eli Lilly And Company | Treatment of tumors in mammals |
| US4965374A (en) * | 1987-08-28 | 1990-10-23 | Eli Lilly And Company | Process for and intermediates of 2',2'-difluoronucleosides |
| US5223608A (en) * | 1987-08-28 | 1993-06-29 | Eli Lilly And Company | Process for and intermediates of 2',2'-difluoronucleosides |
| UA41261C2 (uk) * | 1992-06-22 | 2001-09-17 | Елі Ліллі Енд Компані | Спосіб одержання збагачених бета-аномером нуклеозидів |
| AU4134793A (en) * | 1992-06-22 | 1993-12-23 | Eli Lilly And Company | 2'-deoxy-2',2'-difluoro(2,6,8-substituted) purine nucleosides having anti-viral and anti-cancer activity and intermediates |
| IL106078A0 (en) * | 1992-06-22 | 1993-10-20 | Lilly Co Eli | Stereoselective anion glycosylation process |
| TW356472B (en) * | 1992-09-01 | 1999-04-21 | Lilly Co Eli | A process for anomerizing nucleosides |
| US5637688A (en) * | 1994-12-13 | 1997-06-10 | Eli Lilly And Company | Process for preparing 1-(2'-deoxy-2'-difluoro-d-ribofuranosyl)-4-aminopyrimidin-2-one hydrochloride |
-
1994
- 1994-12-13 US US08/355,372 patent/US5637688A/en not_active Expired - Lifetime
-
1995
- 1995-11-01 AR AR33407495A patent/AR001041A1/es unknown
- 1995-11-02 IL IL11585295A patent/IL115852A/xx not_active IP Right Cessation
- 1995-11-02 PE PE1995283631A patent/PE49296A1/es not_active IP Right Cessation
- 1995-11-03 ZA ZA959320A patent/ZA959320B/xx unknown
- 1995-11-09 DK DK95308030T patent/DK0719788T3/da active
- 1995-11-09 AT AT95308030T patent/ATE179986T1/de active
- 1995-11-09 SI SI9530272T patent/SI0719788T1/xx unknown
- 1995-11-09 ES ES95308030T patent/ES2130542T3/es not_active Expired - Lifetime
- 1995-11-09 EP EP95308030A patent/EP0719788B1/en not_active Expired - Lifetime
- 1995-11-09 DE DE69509624T patent/DE69509624T2/de not_active Expired - Lifetime
- 1995-11-10 CO CO95053319A patent/CO4520286A1/es unknown
- 1995-11-13 YU YU70895A patent/YU49314B/sh unknown
- 1995-11-14 CZ CZ19971798A patent/CZ290941B6/cs not_active IP Right Cessation
- 1995-11-14 JP JP8518835A patent/JPH10510806A/ja active Pending
- 1995-11-14 TW TW084112041A patent/TW379226B/zh not_active IP Right Cessation
- 1995-11-14 WO PCT/US1995/014864 patent/WO1996018637A1/en not_active Ceased
- 1995-11-14 UA UA97062781A patent/UA48152C2/uk unknown
- 1995-11-14 AU AU41101/96A patent/AU689674B2/en not_active Ceased
- 1995-11-14 RU RU97111801/04A patent/RU2154648C2/ru not_active IP Right Cessation
- 1995-11-14 RO RO97-01060A patent/RO117327B1/ro unknown
- 1995-11-14 NZ NZ296476A patent/NZ296476A/xx not_active IP Right Cessation
- 1995-11-14 KR KR1019970703880A patent/KR100424991B1/ko not_active Expired - Fee Related
- 1995-11-14 CN CN95196792A patent/CN1047177C/zh not_active Expired - Fee Related
- 1995-11-14 BR BR9509979A patent/BR9509979A/pt not_active Application Discontinuation
- 1995-11-14 PL PL95321046A patent/PL181732B1/pl unknown
- 1995-11-14 HU HU9800673A patent/HU219021B/hu not_active IP Right Cessation
- 1995-11-16 MY MYPI95003490A patent/MY112488A/en unknown
-
1997
- 1997-04-11 US US08/837,071 patent/US5808048A/en not_active Expired - Lifetime
- 1997-06-10 BG BG101591A patent/BG62738B1/bg unknown
- 1997-06-11 NO NO972679A patent/NO306783B1/no not_active IP Right Cessation
-
1999
- 1999-05-19 GR GR990401358T patent/GR3030265T3/el unknown
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