FR2446290A1 - Nouveau procede de synthese de la vindesine - Google Patents
Nouveau procede de synthese de la vindesineInfo
- Publication number
- FR2446290A1 FR2446290A1 FR8000466A FR8000466A FR2446290A1 FR 2446290 A1 FR2446290 A1 FR 2446290A1 FR 8000466 A FR8000466 A FR 8000466A FR 8000466 A FR8000466 A FR 8000466A FR 2446290 A1 FR2446290 A1 FR 2446290A1
- Authority
- FR
- France
- Prior art keywords
- vindesin
- synthesis
- new process
- vindesine
- azide
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- NDMPLJNOPCLANR-UHFFFAOYSA-N 3,4-dihydroxy-15-(4-hydroxy-18-methoxycarbonyl-5,18-seco-ibogamin-18-yl)-16-methoxy-1-methyl-6,7-didehydro-aspidospermidine-3-carboxylic acid methyl ester Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 NDMPLJNOPCLANR-UHFFFAOYSA-N 0.000 abstract 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 2
- 150000001540 azides Chemical class 0.000 abstract 2
- UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 abstract 2
- 229960004355 vindesine Drugs 0.000 abstract 2
- JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 abstract 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 abstract 1
- -1 n-butyl nitrite Chemical compound 0.000 abstract 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 1
- 230000009466 transformation Effects 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
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Saccharide Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
On prépare la vindésine par transformation du carbohydrazide en E-3 de la 4-désacetylVLB en azide correspondant à l'aide d'un nitrite, comme le nitrite de n-butyle, dans le THF, puis en faisant réagir l'azide ainsi formé avec une tri(akyl ou aryl)phosphine pour former un acyliminophosphorane intermédiaire que l'on décompose par un acide pour obtenir une vindésine de pureté élevée avec un bon rendement.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/003,442 US4210584A (en) | 1979-01-15 | 1979-01-15 | Vindesine synthesis |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2446290A1 true FR2446290A1 (fr) | 1980-08-08 |
| FR2446290B1 FR2446290B1 (fr) | 1983-06-24 |
Family
ID=21705894
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8000466A Granted FR2446290A1 (fr) | 1979-01-15 | 1980-01-10 | Nouveau procede de synthese de la vindesine |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US4210584A (fr) |
| EP (1) | EP0014053B1 (fr) |
| JP (1) | JPS5598195A (fr) |
| KR (1) | KR830002840B1 (fr) |
| AR (1) | AR223694A1 (fr) |
| AT (1) | AT371127B (fr) |
| AU (1) | AU5452280A (fr) |
| BE (1) | BE881078A (fr) |
| BG (1) | BG33295A3 (fr) |
| CA (1) | CA1148945A (fr) |
| CH (1) | CH645383A5 (fr) |
| CS (1) | CS214691B2 (fr) |
| DD (1) | DD148779A5 (fr) |
| DE (1) | DE3065852D1 (fr) |
| DK (1) | DK148961C (fr) |
| ES (2) | ES487682A0 (fr) |
| FI (1) | FI800071A (fr) |
| FR (1) | FR2446290A1 (fr) |
| GB (1) | GB2040934B (fr) |
| GR (1) | GR72464B (fr) |
| HU (1) | HU182083B (fr) |
| IE (1) | IE49376B1 (fr) |
| IL (1) | IL59119A (fr) |
| IT (1) | IT1140506B (fr) |
| LU (1) | LU82079A1 (fr) |
| MY (1) | MY8500570A (fr) |
| NZ (1) | NZ192574A (fr) |
| PH (1) | PH15343A (fr) |
| PL (1) | PL124350B1 (fr) |
| PT (1) | PT70681A (fr) |
| RO (1) | RO77532A (fr) |
| SU (1) | SU906381A3 (fr) |
| YU (1) | YU5680A (fr) |
| ZA (1) | ZA80157B (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60112895A (ja) * | 1983-11-24 | 1985-06-19 | Nippon Oil & Fats Co Ltd | 金属圧延用潤滑油 |
| FR2651348B1 (fr) * | 1989-08-04 | 1993-01-22 | Adir | |
| TW258739B (fr) * | 1992-04-04 | 1995-10-01 | Hoechst Ag | |
| EP1235598A2 (fr) * | 1999-11-12 | 2002-09-04 | Angiotech Pharmaceuticals, Inc. | Compositions et methodes destinees au traitement de maladies utilisant une therapie radioactive et des inhibiteurs du cycle cellulaire combines |
| JP2006516548A (ja) | 2002-12-30 | 2006-07-06 | アンジオテック インターナショナル アクツィエン ゲゼルシャフト | 迅速ゲル化ポリマー組成物からの薬物送達法 |
| CN106831827B (zh) * | 2016-12-31 | 2019-03-29 | 广州白云山汉方现代药业有限公司 | 一种长春地辛的分离纯化方法 |
| CN106831826B (zh) * | 2016-12-31 | 2018-07-06 | 广州白云山汉方现代药业有限公司 | 一种从长春花中制备长春地辛的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2756235A (en) * | 1954-08-27 | 1956-07-24 | Lilly Co Eli | Method of producing lysergic acid amide |
-
1979
- 1979-01-15 US US06/003,442 patent/US4210584A/en not_active Expired - Lifetime
-
1980
- 1980-01-10 BE BE1/9677A patent/BE881078A/fr not_active IP Right Cessation
- 1980-01-10 ZA ZA00800157A patent/ZA80157B/xx unknown
- 1980-01-10 GB GB8000870A patent/GB2040934B/en not_active Expired
- 1980-01-10 GR GR60929A patent/GR72464B/el unknown
- 1980-01-10 YU YU00056/80A patent/YU5680A/xx unknown
- 1980-01-10 CS CS80235A patent/CS214691B2/cs unknown
- 1980-01-10 AU AU54522/80A patent/AU5452280A/en not_active Abandoned
- 1980-01-10 FR FR8000466A patent/FR2446290A1/fr active Granted
- 1980-01-10 DE DE8080300095T patent/DE3065852D1/de not_active Expired
- 1980-01-10 EP EP80300095A patent/EP0014053B1/fr not_active Expired
- 1980-01-10 CA CA000343455A patent/CA1148945A/fr not_active Expired
- 1980-01-10 NZ NZ192574A patent/NZ192574A/xx unknown
- 1980-01-10 FI FI800071A patent/FI800071A/fi not_active Application Discontinuation
- 1980-01-10 PT PT70681A patent/PT70681A/pt unknown
- 1980-01-11 AT AT0014080A patent/AT371127B/de not_active IP Right Cessation
- 1980-01-11 HU HU8052A patent/HU182083B/hu not_active IP Right Cessation
- 1980-01-11 JP JP250480A patent/JPS5598195A/ja active Granted
- 1980-01-13 IL IL59119A patent/IL59119A/xx unknown
- 1980-01-14 BG BG046233A patent/BG33295A3/xx unknown
- 1980-01-14 DK DK14780A patent/DK148961C/da not_active IP Right Cessation
- 1980-01-14 AR AR279615A patent/AR223694A1/es active
- 1980-01-14 PH PH23506A patent/PH15343A/en unknown
- 1980-01-14 LU LU82079A patent/LU82079A1/fr unknown
- 1980-01-14 ES ES487682A patent/ES487682A0/es active Granted
- 1980-01-14 IE IE60/80A patent/IE49376B1/en unknown
- 1980-01-14 PL PL1980221359A patent/PL124350B1/pl unknown
- 1980-01-14 CH CH28780A patent/CH645383A5/fr not_active IP Right Cessation
- 1980-01-14 SU SU802872553A patent/SU906381A3/ru active
- 1980-01-14 IT IT19210/80A patent/IT1140506B/it active
- 1980-01-15 DD DD80218466A patent/DD148779A5/de unknown
- 1980-01-15 KR KR1019800000134A patent/KR830002840B1/ko active
- 1980-01-15 ES ES487726A patent/ES8101612A1/es not_active Expired
- 1980-01-15 RO RO8099874A patent/RO77532A/fr unknown
-
1985
- 1985-12-30 MY MY570/85A patent/MY8500570A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| EXBK/78 * |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FR2442227A1 (fr) | Procede de production d'acides threo-3-amino-2-hydroxybutanoylaminoacetiques | |
| FR2446290A1 (fr) | Nouveau procede de synthese de la vindesine | |
| FR2400021A1 (fr) | Preparation d'acide (1r,cis);caronaldehydique | |
| FR2375244A1 (fr) | Procede de preparation de l'acide 2-carboxyethyl (phenyl) phosphinique | |
| FR2433538A1 (fr) | Procede de synthese de 16-pregnanes a partir de 17(20)-steroides | |
| FR2386510A1 (fr) | Procede de production de cyclobutanones | |
| FR2454996B1 (fr) | Procede de production d'acide phosphorique concentre par decantation des matieres solides en suspension a l'aide d'un agent floculant | |
| FR2381777A1 (fr) | Procede de preparation d'oxazolinoazetidinones a partir d'acide 6-aminopenicillanique et nouveaux produits ainsi obtenus | |
| FR2392956A1 (fr) | Procede de production d'esters d'acide phenylglyoxylique | |
| GB1351467A (en) | Alicyclic diketones and process for their manufacture | |
| GB1145583A (en) | Fungicidal agents | |
| FR2356637A1 (fr) | 2-phenyl-2-carboxyethyl 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indolylacetate, et procede de preparation de ce produit presentant une activite anti-inflammatoire | |
| LU78585A1 (fr) | Procede de preparation d'acide 6-aminopenicillanique par transformation enzymatique d'une penicilline | |
| FR2391221A1 (fr) | Procede de preparation de l'acide n,n-dimethylamino-methane-diphosphonique a partir de n,n-dimethylformamide, d'acide phosphoreux et d'oxychlorure de phosphore | |
| FR2450807A1 (fr) | Procede pour la preparation d'alkylamines aromatiques | |
| FR2452496A1 (fr) | Procede perfectionne pour la production de 3-0-demethylfortimicines | |
| PT80085A (en) | Process for the production of alloy steels using chemically prepared v203 as a vanadium additive | |
| FR2389604A1 (fr) | ||
| BE858102A (fr) | Procede de production du sel trisodique de l'acide carboxymethyloxy-succinique | |
| EG15987A (en) | Process and intermediates for preparation of 1,1-dioxopenicillan-oyloxymethyl 6-beta-aminopenicillanate | |
| FR2417471A1 (fr) | Procede de preparation de perborate de sodium tetrahydrate | |
| ES465723A1 (es) | Procedimiento para la preparacion y recuperacion de haloge- noacilamidas. | |
| ES8609297A1 (es) | Procedimiento de preparar aminolactonas | |
| SE7904739L (sv) | Forfarande for framstellning av n-tritylimidazolforeningar | |
| FR2365576A1 (fr) | Procede de production d'halogenures de diesters d'acide dithiophosphorique |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |