AR069319A1 - Metodo para preparar capecitabina y compuesto intermediario de trialquil carbonato. - Google Patents
Metodo para preparar capecitabina y compuesto intermediario de trialquil carbonato.Info
- Publication number
- AR069319A1 AR069319A1 ARP080104968A ARP080104968A AR069319A1 AR 069319 A1 AR069319 A1 AR 069319A1 AR P080104968 A ARP080104968 A AR P080104968A AR P080104968 A ARP080104968 A AR P080104968A AR 069319 A1 AR069319 A1 AR 069319A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compound
- carbonate
- preparing
- trialquil
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 8
- 238000000034 method Methods 0.000 title abstract 3
- GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 title abstract 2
- GAGWJHPBXLXJQN-UHFFFAOYSA-N Capecitabine Natural products C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1C1C(O)C(O)C(C)O1 GAGWJHPBXLXJQN-UHFFFAOYSA-N 0.000 title abstract 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 title abstract 2
- 229960004117 capecitabine Drugs 0.000 title abstract 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 6
- -1 methylacetonide compound Chemical class 0.000 abstract 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- 125000001188 haloalkyl group Chemical group 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 230000021235 carbamoylation Effects 0.000 abstract 1
- MMCOUVMKNAHQOY-UHFFFAOYSA-N carbonoperoxoic acid Chemical group OOC(O)=O MMCOUVMKNAHQOY-UHFFFAOYSA-N 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical compound NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 abstract 1
- 229960004413 flucytosine Drugs 0.000 abstract 1
- 230000013595 glycosylation Effects 0.000 abstract 1
- 238000006206 glycosylation reaction Methods 0.000 abstract 1
- 229910052740 iodine Chemical group 0.000 abstract 1
- 239000011630 iodine Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- XHRRYUDVWPPWIP-UHFFFAOYSA-N pentyl carbonochloridate Chemical compound CCCCCOC(Cl)=O XHRRYUDVWPPWIP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- 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
- 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)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Saccharide Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Reivindicacion 1: Un método para preparar capecitabina de formula 1, caracterizado por los pasos de: (1) hidrolizar un compuesto metilacetonida de formula 2 para obtener un compuesto triol de formula 3; (2) hacer reaccionar el compuesto de formula 3 con un haloalquil formato de formula 4 en presencia de una mezcla de piridina y trietilamina para obtener un compuesto trialquil carbonato rico en beta-anomero de formula 5; (3) realizar una glicosilacion del compuesto de formula 5 usando 5-fluorocitosina en presencia de un ácido para obtener un compuesto dialcoxicarbonil citidina de formula 6; (4) realizar carbamoilacion del compuesto de formula 6 usando n-pentil cloroformato para obtener un compuesto carbamoilcitidina de formula 7; y (5) desproteger los grupos protectores hidroxi carbonato del compuesto de formula 7: en donde, X es cloro, bromo o iodo; y R es metilo o etilo. Reivindicacion 7: Un método para preparar un compuesto trialquil carbonato de formula caracterizado porque comprende los pasos de: (1) hidrolizar un compuesto metilacetonida de formula 2 para obtener un compuesto triol de formula 3; y (2) permitir que el compuesto de formula 3 reaccione con un haloalquil formato de formula 4 en presencia de una mezcla de piridina y trietilamina para obtener un trialquil carbonato rico en beta-anomero de formula 5: en donde X y R tienen el mismo significado que el definido en la reivindicacion 1.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020070118062A KR101013312B1 (ko) | 2007-11-19 | 2007-11-19 | 카페시타빈의 제조방법 및 이에 사용되는 β-아노머가강화된 트리알킬카보네이트 화합물의 제조방법 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR069319A1 true AR069319A1 (es) | 2010-01-13 |
Family
ID=40667680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP080104968A AR069319A1 (es) | 2007-11-19 | 2008-11-14 | Metodo para preparar capecitabina y compuesto intermediario de trialquil carbonato. |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US8097706B2 (es) |
| EP (1) | EP2220090A4 (es) |
| JP (1) | JP2011503228A (es) |
| KR (1) | KR101013312B1 (es) |
| CN (1) | CN101861320A (es) |
| AR (1) | AR069319A1 (es) |
| AU (1) | AU2008327061B2 (es) |
| BR (1) | BRPI0820494A8 (es) |
| CA (1) | CA2704815C (es) |
| CL (1) | CL2008003386A1 (es) |
| IL (1) | IL205832A0 (es) |
| MX (1) | MX2010005015A (es) |
| NZ (1) | NZ585129A (es) |
| PE (1) | PE20091358A1 (es) |
| RU (1) | RU2439064C1 (es) |
| TW (1) | TWI356061B (es) |
| WO (1) | WO2009066892A1 (es) |
| ZA (1) | ZA201003216B (es) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2456778A4 (en) * | 2009-07-23 | 2013-05-29 | Scinopharm Taiwan Ltd | PROCESS FOR PRODUCING FLUOROCYTIDINE DERIVATIVES |
| CN102516338B (zh) * | 2011-12-09 | 2014-04-02 | 海南锦瑞制药股份有限公司 | 一种卡培他滨化合物、其药物组合物及其制备方法 |
| CN103374052B (zh) * | 2012-04-19 | 2016-04-20 | 齐鲁制药有限公司 | 卡培他滨晶型及其制备方法 |
| US10435429B2 (en) | 2017-10-03 | 2019-10-08 | Nucorion Pharmaceuticals, Inc. | 5-fluorouridine monophosphate cyclic triester compounds |
| AU2019207626B2 (en) | 2018-01-10 | 2023-10-05 | Nucorion Pharmaceuticals, Inc. | Phosphor(n)amidatacetal and phosph(on)atalcetal compounds |
| US11427550B2 (en) | 2018-01-19 | 2022-08-30 | Nucorion Pharmaceuticals, Inc. | 5-fluorouracil compounds |
| WO2019143860A1 (en) * | 2018-01-19 | 2019-07-25 | Nucorion Pharmaceuticals, Inc. | 5-fluorouracil compounds |
| MX2022000573A (es) | 2019-07-17 | 2022-02-10 | Nucorion Pharmaceuticals Inc | Compuestos ciclicos de desoxirribonucleotido. |
| CN115605492B (zh) | 2020-04-21 | 2025-09-16 | 配体制药股份有限公司 | 核苷酸前药化合物 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1135258A (en) | 1979-06-15 | 1982-11-09 | Richard D'souza | Process for the preparation of 5'deoxy-5-fluorouridine |
| US5272949A (en) | 1992-09-23 | 1993-12-28 | Buckeye Bluegrass Farms, Inc. | Device for cutting sod grown over plastic sheeting |
| TW254946B (es) | 1992-12-18 | 1995-08-21 | Hoffmann La Roche | |
| AU671491B2 (en) | 1992-12-18 | 1996-08-29 | F. Hoffmann-La Roche Ag | N-oxycarbonyl substituted 5'-deoxy-5-fluorcytidines |
| US5476932A (en) | 1994-08-26 | 1995-12-19 | Hoffmann-La Roche Inc. | Process for producing N4-acyl-5'-deoxy-5-fluorocytidine derivatives |
| NZ330360A (en) * | 1997-06-02 | 1999-03-29 | Hoffmann La Roche | 5'-deoxy-cytidine derivatives, their manufacture and use as antitumoral agents |
| KR100908363B1 (ko) * | 2007-02-28 | 2009-07-20 | 한미약품 주식회사 | 트라이-Ｏ-아세틸-5-데옥시-β-Ｄ-라이보퓨라노즈의입체선택적 제조방법 및 이의 분리방법 |
-
2007
- 2007-11-19 KR KR1020070118062A patent/KR101013312B1/ko not_active Expired - Fee Related
-
2008
- 2008-11-07 AU AU2008327061A patent/AU2008327061B2/en not_active Ceased
- 2008-11-07 JP JP2010534876A patent/JP2011503228A/ja not_active Withdrawn
- 2008-11-07 US US12/742,367 patent/US8097706B2/en not_active Expired - Fee Related
- 2008-11-07 CN CN200880116613A patent/CN101861320A/zh active Pending
- 2008-11-07 RU RU2010125257/04A patent/RU2439064C1/ru not_active IP Right Cessation
- 2008-11-07 CA CA2704815A patent/CA2704815C/en not_active Expired - Fee Related
- 2008-11-07 EP EP08852094A patent/EP2220090A4/en not_active Withdrawn
- 2008-11-07 NZ NZ585129A patent/NZ585129A/en not_active IP Right Cessation
- 2008-11-07 WO PCT/KR2008/006565 patent/WO2009066892A1/en not_active Ceased
- 2008-11-07 BR BRPI0820494A patent/BRPI0820494A8/pt not_active IP Right Cessation
- 2008-11-07 MX MX2010005015A patent/MX2010005015A/es not_active Application Discontinuation
- 2008-11-14 CL CL2008003386A patent/CL2008003386A1/es unknown
- 2008-11-14 AR ARP080104968A patent/AR069319A1/es not_active Application Discontinuation
- 2008-11-18 TW TW097144494A patent/TWI356061B/zh not_active IP Right Cessation
- 2008-11-19 PE PE2008001949A patent/PE20091358A1/es not_active Application Discontinuation
-
2010
- 2010-05-06 ZA ZA2010/03216A patent/ZA201003216B/en unknown
- 2010-05-17 IL IL205832A patent/IL205832A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0820494A2 (pt) | 2015-06-16 |
| NZ585129A (en) | 2011-11-25 |
| MX2010005015A (es) | 2010-05-27 |
| WO2009066892A1 (en) | 2009-05-28 |
| ZA201003216B (en) | 2011-07-27 |
| TW200927754A (en) | 2009-07-01 |
| CA2704815A1 (en) | 2009-05-28 |
| KR20090051595A (ko) | 2009-05-22 |
| PE20091358A1 (es) | 2009-09-23 |
| JP2011503228A (ja) | 2011-01-27 |
| US20100249395A1 (en) | 2010-09-30 |
| KR101013312B1 (ko) | 2011-02-09 |
| EP2220090A4 (en) | 2011-03-16 |
| EP2220090A1 (en) | 2010-08-25 |
| IL205832A0 (en) | 2010-11-30 |
| RU2439064C1 (ru) | 2012-01-10 |
| CN101861320A (zh) | 2010-10-13 |
| AU2008327061B2 (en) | 2011-03-24 |
| TWI356061B (en) | 2012-01-11 |
| AU2008327061A1 (en) | 2009-05-28 |
| BRPI0820494A8 (pt) | 2015-11-03 |
| CA2704815C (en) | 2012-03-13 |
| CL2008003386A1 (es) | 2009-04-13 |
| US8097706B2 (en) | 2012-01-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |