CS235503B2 - Method of vindesinmonosulphate preparation - Google Patents
Method of vindesinmonosulphate preparation Download PDFInfo
- Publication number
- CS235503B2 CS235503B2 CS796720A CS672079A CS235503B2 CS 235503 B2 CS235503 B2 CS 235503B2 CS 796720 A CS796720 A CS 796720A CS 672079 A CS672079 A CS 672079A CS 235503 B2 CS235503 B2 CS 235503B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- sulfuric acid
- vindesine
- rate
- added
- addition
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 68
- 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 claims abstract description 26
- 229960004355 vindesine Drugs 0.000 claims abstract description 26
- 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 claims abstract description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000003756 stirring Methods 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims description 3
- VFNGKCDDZUSWLR-UHFFFAOYSA-L disulfate(2-) Chemical compound [O-]S(=O)(=O)OS([O-])(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-L 0.000 abstract description 9
- VCSZKSHWUBFOOE-UHFFFAOYSA-N dioxidanium;sulfate Chemical compound O.O.OS(O)(=O)=O VCSZKSHWUBFOOE-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229960004528 vincristine Drugs 0.000 description 2
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 2
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 2
- KABRXLINDSPGDF-UHFFFAOYSA-N 7-bromoisoquinoline Chemical compound C1=CN=CC2=CC(Br)=CC=C21 KABRXLINDSPGDF-UHFFFAOYSA-N 0.000 description 1
- 206010025323 Lymphomas Diseases 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229940122803 Vinca alkaloid Drugs 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 208000037841 lung tumor Diseases 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 230000000174 oncolytic effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000000954 titration curve Methods 0.000 description 1
- 229960005212 vindesine sulfate Drugs 0.000 description 1
- KLUZWGITOFOKBO-UHFFFAOYSA-N virosine Natural products C1CC2=CC(=O)OC22C3CCCN3C1C2 KLUZWGITOFOKBO-UHFFFAOYSA-N 0.000 description 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94959578A | 1978-10-10 | 1978-10-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS235503B2 true CS235503B2 (en) | 1985-05-15 |
Family
ID=25489302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS796720A CS235503B2 (en) | 1978-10-10 | 1979-10-03 | Method of vindesinmonosulphate preparation |
Country Status (32)
| Country | Link |
|---|---|
| EP (1) | EP0009996B1 (el) |
| JP (1) | JPS5553295A (el) |
| KR (1) | KR850000150B1 (el) |
| AR (1) | AR225153A1 (el) |
| AT (1) | AT370422B (el) |
| AU (1) | AU525702B2 (el) |
| BE (1) | BE879213A (el) |
| BG (1) | BG34763A3 (el) |
| CA (1) | CA1114817A (el) |
| CH (2) | CH649301A5 (el) |
| CS (1) | CS235503B2 (el) |
| DD (1) | DD146461A5 (el) |
| DE (1) | DE2964913D1 (el) |
| DK (1) | DK146823C (el) |
| EG (1) | EG14140A (el) |
| ES (1) | ES484827A1 (el) |
| FI (1) | FI70223C (el) |
| FR (1) | FR2438659A1 (el) |
| GB (1) | GB2031893B (el) |
| GR (1) | GR72394B (el) |
| HU (1) | HU180744B (el) |
| IE (1) | IE48958B1 (el) |
| IL (1) | IL58390A (el) |
| LU (1) | LU81763A1 (el) |
| MY (1) | MY8500569A (el) |
| NZ (1) | NZ191744A (el) |
| PH (1) | PH16092A (el) |
| PL (1) | PL117678B1 (el) |
| PT (1) | PT70269A (el) |
| RO (1) | RO77380A (el) |
| YU (1) | YU241179A (el) |
| ZA (1) | ZA795268B (el) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4558053A (en) * | 1983-12-21 | 1985-12-10 | Eli Lilly And Company | Naphthalene-1,5-disulfonate salts of dimeric indole-dihydroindole alkaloids |
| CN112592357B (zh) * | 2020-12-22 | 2022-03-22 | 海南长春花药业有限公司 | 一种硫酸长春地辛的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL48685A (en) * | 1975-01-09 | 1980-03-31 | Lilly Co Eli | Amides of vincadioline and vinblastine |
| US4029663A (en) * | 1975-07-10 | 1977-06-14 | Eli Lilly And Company | Dimeric anhydro-vinca derivatives |
| GR69783B (el) * | 1976-09-08 | 1982-07-07 | Lilly Co Eli |
-
1979
- 1979-10-02 AR AR278306A patent/AR225153A1/es active
- 1979-10-03 FI FI793065A patent/FI70223C/fi not_active IP Right Cessation
- 1979-10-03 CS CS796720A patent/CS235503B2/cs unknown
- 1979-10-03 NZ NZ191744A patent/NZ191744A/xx unknown
- 1979-10-03 YU YU02411/79A patent/YU241179A/xx unknown
- 1979-10-03 PT PT70269A patent/PT70269A/pt unknown
- 1979-10-03 AU AU51427/79A patent/AU525702B2/en not_active Expired
- 1979-10-03 ZA ZA00795268A patent/ZA795268B/xx unknown
- 1979-10-04 CA CA336,959A patent/CA1114817A/en not_active Expired
- 1979-10-04 IL IL58390A patent/IL58390A/xx unknown
- 1979-10-04 JP JP12879579A patent/JPS5553295A/ja active Granted
- 1979-10-05 BE BE1/9554A patent/BE879213A/fr not_active IP Right Cessation
- 1979-10-05 FR FR7924841A patent/FR2438659A1/fr active Granted
- 1979-10-05 PL PL1979218756A patent/PL117678B1/pl unknown
- 1979-10-06 RO RO7998873A patent/RO77380A/ro unknown
- 1979-10-08 LU LU81763A patent/LU81763A1/fr unknown
- 1979-10-08 GR GR60215A patent/GR72394B/el unknown
- 1979-10-08 ES ES484827A patent/ES484827A1/es not_active Expired
- 1979-10-08 CH CH691/84A patent/CH649301A5/fr not_active IP Right Cessation
- 1979-10-08 BG BG045074A patent/BG34763A3/xx unknown
- 1979-10-08 CH CH904479A patent/CH645120A5/fr not_active IP Right Cessation
- 1979-10-09 EP EP79302152A patent/EP0009996B1/en not_active Expired
- 1979-10-09 EG EG590/79A patent/EG14140A/xx active
- 1979-10-09 DK DK422979A patent/DK146823C/da not_active IP Right Cessation
- 1979-10-09 HU HU79EI881A patent/HU180744B/hu unknown
- 1979-10-09 DE DE7979302152T patent/DE2964913D1/de not_active Expired
- 1979-10-09 IE IE1914/79A patent/IE48958B1/en not_active IP Right Cessation
- 1979-10-09 GB GB7935062A patent/GB2031893B/en not_active Expired
- 1979-10-09 AT AT0658279A patent/AT370422B/de not_active IP Right Cessation
- 1979-10-10 KR KR7903467A patent/KR850000150B1/ko not_active Expired
- 1979-10-10 DD DD79216158A patent/DD146461A5/de unknown
-
1981
- 1981-02-03 PH PH25176A patent/PH16092A/en unknown
-
1985
- 1985-12-30 MY MY569/85A patent/MY8500569A/xx unknown
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