AR024852A1 - Procedimiento para la produccion de ditartrato de 5'-nor-anhidrovinblastina a partir de especies vegetales del genero catharanthus y procedimiento a escala industrial. - Google Patents
Procedimiento para la produccion de ditartrato de 5'-nor-anhidrovinblastina a partir de especies vegetales del genero catharanthus y procedimiento a escala industrial.Info
- Publication number
- AR024852A1 AR024852A1 ARP000100126A ARP000100126A AR024852A1 AR 024852 A1 AR024852 A1 AR 024852A1 AR P000100126 A ARP000100126 A AR P000100126A AR P000100126 A ARP000100126 A AR P000100126A AR 024852 A1 AR024852 A1 AR 024852A1
- Authority
- AR
- Argentina
- Prior art keywords
- anhydrovinblastine
- procedure
- ditartrate
- catharanthus
- purification
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 8
- 241000208328 Catharanthus Species 0.000 title abstract 3
- 235000013311 vegetables Nutrition 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 241000894007 species Species 0.000 title 1
- GBABOYUKABKIAF-IELIFDKJSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-IELIFDKJSA-N 0.000 title 1
- 229950001104 anhydrovinblastine Drugs 0.000 abstract 10
- 238000000746 purification Methods 0.000 abstract 4
- FFRFGVHNKJYNOV-DOVUUNBWSA-N 3',4'-Anhydrovinblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C=C(C2)CC)N2CCC2=C1NC1=CC=CC=C21 FFRFGVHNKJYNOV-DOVUUNBWSA-N 0.000 abstract 3
- 229930013930 alkaloid Natural products 0.000 abstract 3
- 230000015572 biosynthetic process Effects 0.000 abstract 3
- 238000003786 synthesis reaction Methods 0.000 abstract 3
- WVTGEXAIVZDLCR-UHFFFAOYSA-N Vindoline Natural products CC1C2CN3CCCC14CCC5Nc6ccccc6C25C34 WVTGEXAIVZDLCR-UHFFFAOYSA-N 0.000 abstract 2
- GKWYINOZGDHWRA-UHFFFAOYSA-N catharanthine Natural products C1C(CC)(O)CC(CC2C(=O)OC)CN1CCC1=C2NC2=CC=CC=C12 GKWYINOZGDHWRA-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- CXBGOBGJHGGWIE-IYJDUVQVSA-N vindoline Chemical compound CN([C@H]1[C@](O)([C@@H]2OC(C)=O)C(=O)OC)C3=CC(OC)=CC=C3[C@]11CCN3CC=C[C@]2(CC)[C@@H]13 CXBGOBGJHGGWIE-IYJDUVQVSA-N 0.000 abstract 2
- 241000196324 Embryophyta Species 0.000 abstract 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 229910001447 ferric ion Inorganic materials 0.000 abstract 1
- 238000000227 grinding Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000004064 recycling Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/04—Dimeric indole alkaloids, e.g. vincaleucoblastine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Se sintetiza el ditartrato de 5-nor-anhidrovinblastina a partir de alcaloides extraidos de la especie vegetal Catharantus roseus mediante un procedimientodonde se procesa el vegetal fresco de manera tal que los alcaloides de interés sufran la menord egradacion posible; se utiliza una mezcla impura de vindolina ycatarantina para la síntesis de anhidrovinblastina por la vía del catalizador ion férrico; se desarrolla un método de conservar la anhidrovinblastina; serealiza la purificacion yreciclad o de solventes; se sintetiza la 5-nor-anhidrovinblastina base en tandem, sin aislar el intermediario bromado; se purifica la5-nor-anhidrovinblastina base por cromatografía y cristalizacion; por ultimo se desarrolla un método de obtenciondel ditartra to de 5-nor-anhidrovinblastinaque no genera pérdidas de materia activa para obtener la pureza deseada. Lo que resulta en un mayor rendimiento global, una disminucion en los tiempos deprocesos, una disminucion en los volumenes desolventes utilizados y una disminucion de la cantidad de purificaciones al resumir varias reacciones en pasosunicos de proceso. De tal manera el nuevo proceso de produccion es más economico y eficiente. El procedimiento puede dividirse en sieteetapas principales, quese enumeran a continuacion: 1)molienda de materiales vegetal de Catharanthus no degradado. 2)obtencion de los alcaloides totales del vegetal de Catharanthus.3)obtencion de la fraccion cromatográfica de vindolina y catarantina.4)síntesis y purificacion de anhidrovinblastina. 5)síntesis de 5-nor-anhidrovinblastina,6)purificacion de 5-nor-anhidrovinblastina base, 7)preparacion del ditartrato de 5-nor-anhidrovinblastina.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ARP000100126A AR024852A1 (es) | 2000-01-12 | 2000-01-12 | Procedimiento para la produccion de ditartrato de 5'-nor-anhidrovinblastina a partir de especies vegetales del genero catharanthus y procedimiento a escala industrial. |
| PT01100018T PT1118616E (pt) | 2000-01-12 | 2001-01-04 | Processo para a producao de ditartarato de 5'-nor-anidrovinblastina a partir de plantas do genero catharanthus |
| DK01100018T DK1118616T3 (da) | 2000-01-12 | 2001-01-04 | Fremgangsmåde til fremstilling af 5'-nor-anhydrovinblastin-ditartrat ud fra planter af slægten Catharanthus |
| ES01100018T ES2215795T3 (es) | 2000-01-12 | 2001-01-04 | Procedimiento para producir ditartrato de 5-nor-anhidrovinblastina a partir de plantas de tipo catharantus. |
| EP01100018A EP1118616B1 (en) | 2000-01-12 | 2001-01-04 | Process for the production of 5'-nor-anhydrovinblastine ditartrate from plants of genus catharanthus |
| AT01100018T ATE262534T1 (de) | 2000-01-12 | 2001-01-04 | Verfahren zur herstellung von 5'-nor- anhydrovinblastinditartrat aus pflanzen der gattung catharanthus |
| DE60102399T DE60102399T2 (de) | 2000-01-12 | 2001-01-04 | Verfahren zur Herstellung von 5'-Nor-anhydrovinblastinditartrat aus Pflanzen der Gattung Catharanthus |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ARP000100126A AR024852A1 (es) | 2000-01-12 | 2000-01-12 | Procedimiento para la produccion de ditartrato de 5'-nor-anhidrovinblastina a partir de especies vegetales del genero catharanthus y procedimiento a escala industrial. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR024852A1 true AR024852A1 (es) | 2002-10-30 |
Family
ID=3460784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP000100126A AR024852A1 (es) | 2000-01-12 | 2000-01-12 | Procedimiento para la produccion de ditartrato de 5'-nor-anhidrovinblastina a partir de especies vegetales del genero catharanthus y procedimiento a escala industrial. |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP1118616B1 (es) |
| AR (1) | AR024852A1 (es) |
| AT (1) | ATE262534T1 (es) |
| DE (1) | DE60102399T2 (es) |
| DK (1) | DK1118616T3 (es) |
| ES (1) | ES2215795T3 (es) |
| PT (1) | PT1118616E (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100376577C (zh) * | 2004-02-24 | 2008-03-26 | 上海安体康生植物化学有限公司 | 一种文朵灵和长春质碱的制备方法 |
| FR2894966B1 (fr) * | 2005-12-20 | 2008-03-14 | Pierre Fabre Medicament Sa | Nouvelle forme cristalline de la vinflunine |
| FR2912406B1 (fr) * | 2007-02-13 | 2009-05-08 | Pierre Fabre Medicament Sa | Sels cristalins anhydres de vinflunine, procede de preparation et utilisation en tant que medicament et moyen de purification de la vinflunine. |
| CN102766149B (zh) * | 2012-07-05 | 2014-09-24 | 深圳万乐药业有限公司 | 一种酒石酸长春瑞滨的制备方法 |
| CN103936769B (zh) * | 2014-04-30 | 2016-10-05 | 淮海工学院 | 一种制备高光学纯脱水长春碱的方法 |
| CN112552319A (zh) * | 2020-12-22 | 2021-03-26 | 海南长春花药业有限公司 | 一种酒石酸长春瑞滨的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4307100A (en) * | 1978-08-24 | 1981-12-22 | Agence Nationale De Valorisation De La Recherche (Anvar) | Nor bis-indole compounds usable as medicaments |
| FR2544318B1 (fr) * | 1983-04-14 | 1985-08-16 | Fabre Sa Pierre | Procede de preparation de vindoline et de catharanthine |
| US4778885A (en) * | 1986-09-18 | 1988-10-18 | Allelix Inc. | Production of alkaloid dimers using ferric ion |
-
2000
- 2000-01-12 AR ARP000100126A patent/AR024852A1/es not_active Application Discontinuation
-
2001
- 2001-01-04 PT PT01100018T patent/PT1118616E/pt unknown
- 2001-01-04 DK DK01100018T patent/DK1118616T3/da active
- 2001-01-04 EP EP01100018A patent/EP1118616B1/en not_active Expired - Lifetime
- 2001-01-04 AT AT01100018T patent/ATE262534T1/de active
- 2001-01-04 DE DE60102399T patent/DE60102399T2/de not_active Expired - Lifetime
- 2001-01-04 ES ES01100018T patent/ES2215795T3/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES2215795T3 (es) | 2004-10-16 |
| EP1118616A1 (en) | 2001-07-25 |
| DK1118616T3 (da) | 2004-07-26 |
| DE60102399D1 (de) | 2004-04-29 |
| EP1118616B1 (en) | 2004-03-24 |
| DE60102399T2 (de) | 2005-02-17 |
| ATE262534T1 (de) | 2004-04-15 |
| PT1118616E (pt) | 2004-06-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Dennis et al. | Isolation and characterisation of the two major isomers of [84] fullerene (C 84) | |
| AU1888792A (en) | Methods and compositions for isolating taxanes | |
| CN101560197B (zh) | 从人工栽培的红豆杉枝叶中提取紫杉醇的方法 | |
| AR024852A1 (es) | Procedimiento para la produccion de ditartrato de 5'-nor-anhidrovinblastina a partir de especies vegetales del genero catharanthus y procedimiento a escala industrial. | |
| AU760242B2 (en) | Method for high yield extraction of paclitaxel from paclitaxel-containing material | |
| CN1917893A (zh) | 从雷公藤多苷中分离雷公藤内酯醇化合物的方法 | |
| US6469186B1 (en) | Process for mass production of GMP paclitaxel and related taxanes | |
| de Carvalho et al. | Diastereoselective synthesis of nitroso acetals from (S, E)-γ-aminated nitroalkenes via multicomponent [4+ 2]/[3+ 2] cycloadditions promoted by LiCl or LiClO4 | |
| NZ538766A (en) | A process to purify taxanes from plant biomass | |
| Ohmiya et al. | Alkaloids of Thermopsis lupinoides | |
| CN112321664B (zh) | 提取分离纯化桦褐孔菌醇的方法 | |
| CA2255062C (en) | Process of purification of cyclosporin | |
| KR100629772B1 (ko) | 1,3-프로판디올, 1,2-프로판디올, 글리세롤 및 포도당을포함하는 혼합물로부터 1,3-프로판디올, 또는1,3-프로판디올 및 1,2-프로판디올을 분리하는 방법 | |
| Imai et al. | Improved synthesis of firefly D-luciferyl-D-adenylate—A key intermediate of firefly bioluminescence | |
| Chen et al. | Synthesis of new carbon nanomolecule: C141 | |
| Datta et al. | Chemodifferentiation of diosgenin in Dioscorea composita | |
| Tenza et al. | Stereoselective α-fluoroamide and α-fluoro-γ-lactone synthesis by an asymmetric zwitterionic aza-Claisen rearrangement | |
| Asghari Mirakk et al. | Investigating the effectiveness of environmental and ecological factors on the amount of alkaloid compounds of the medicinal plant henbane (Hyoscyamus spp.) | |
| US7579491B2 (en) | Process for preparing brevifoliol | |
| CN113717131A (zh) | 一种紫杉醇的分离纯化方法 | |
| US2833771A (en) | Process for the preparation of | |
| EP1572618B1 (en) | Process for isolating brevifoliol | |
| Buñuel et al. | A conformationally restricted aspartic acid analogue with a norbornane skeleton. II | |
| CA2108265A1 (en) | Methods and compositions for isolating taxanes | |
| JP2008505108A (ja) | パクリタキセル及びセファロマンニンの分離方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant, registration | ||
| FD | Application declared void or lapsed, e.g., due to non-payment of fee |