JPH0161118B2 - - Google Patents
Info
- Publication number
- JPH0161118B2 JPH0161118B2 JP56128642A JP12864281A JPH0161118B2 JP H0161118 B2 JPH0161118 B2 JP H0161118B2 JP 56128642 A JP56128642 A JP 56128642A JP 12864281 A JP12864281 A JP 12864281A JP H0161118 B2 JPH0161118 B2 JP H0161118B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- ethyl
- compound
- alkyl
- alcohol
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- -1 α-ethyl Chemical group 0.000 claims description 6
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 1
- 229940117975 chromium trioxide Drugs 0.000 claims 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 210000004027 cell Anatomy 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 6
- 230000011278 mitosis Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 230000016507 interphase Effects 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 230000001085 cytostatic effect Effects 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- 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 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 210000000349 chromosome Anatomy 0.000 description 3
- 208000032839 leukemia Diseases 0.000 description 3
- 230000031864 metaphase Effects 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 229960003048 vinblastine Drugs 0.000 description 3
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine 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)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 3
- 229960004528 vincristine Drugs 0.000 description 3
- 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 3
- 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 3
- 229960004355 vindesine Drugs 0.000 description 3
- 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 description 3
- 206010003445 Ascites Diseases 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 210000000805 cytoplasm Anatomy 0.000 description 2
- 231100001231 less toxic Toxicity 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- TYGUTURXHKSOBP-UHFFFAOYSA-N 10-bromo-5,12-dihydroindolo[2,3-g]carbazole-2,3-diol Chemical compound C1=C(Br)C=C2NC3=C(C4=C(C=C(C(=C4)O)O)N4)C4=CC=C3C2=C1 TYGUTURXHKSOBP-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010025323 Lymphomas Diseases 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000031016 anaphase Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 238000007431 microscopic evaluation Methods 0.000 description 1
- 231100001160 nonlethal Toxicity 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001769 paralizing effect Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU802562A HU181745B (en) | 1980-10-22 | 1980-10-22 | Process for producing new vinblastin and leurosidin derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5772992A JPS5772992A (en) | 1982-05-07 |
| JPH0161118B2 true JPH0161118B2 (fr) | 1989-12-27 |
Family
ID=10960005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56128642A Granted JPS5772992A (en) | 1980-10-22 | 1981-08-17 | Manufacture of cell propagation controlling compound and medicinal composition containing same |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS5772992A (fr) |
| AT (1) | AT376678B (fr) |
| BE (1) | BE889989A (fr) |
| CA (1) | CA1174672A (fr) |
| CH (1) | CH648320A5 (fr) |
| DE (1) | DE3132476A1 (fr) |
| ES (1) | ES8300777A1 (fr) |
| FR (1) | FR2492384B1 (fr) |
| GB (1) | GB2086378B (fr) |
| HU (1) | HU181745B (fr) |
| IL (1) | IL63593A0 (fr) |
| IT (1) | IT1138154B (fr) |
| NL (1) | NL8103844A (fr) |
| SE (1) | SE442116B (fr) |
| SU (1) | SU1053757A3 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0321210U (fr) * | 1989-07-11 | 1991-03-01 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU193318B (en) * | 1985-06-12 | 1987-09-28 | Richter Gedeon Vegyeszet | Process for producing new bis- indol derivatives |
| HU198074B (en) * | 1985-06-12 | 1989-07-28 | Richter Gedeon Vegyeszet | Process for producing new bis-indole derivatives and pharmaceutical compositions comprising these compounds |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56128643A (en) * | 1980-03-13 | 1981-10-08 | Sintokogio Ltd | Vertical flaskless type molding machine |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3899493A (en) * | 1972-12-29 | 1975-08-12 | Richter Gedeon Vegyeszet | Chromic acid oxidation of vinblastine sulfate to form vincristine |
| HU178706B (en) * | 1979-04-23 | 1982-06-28 | Richter Gedeon Vegyeszet | Process for preparing bis-indole alkaloids and acid addition salts thereof |
-
1980
- 1980-10-22 HU HU802562A patent/HU181745B/hu not_active IP Right Cessation
-
1981
- 1981-08-17 BE BE0/205691A patent/BE889989A/fr not_active IP Right Cessation
- 1981-08-17 DE DE3132476A patent/DE3132476A1/de active Granted
- 1981-08-17 CA CA000383978A patent/CA1174672A/fr not_active Expired
- 1981-08-17 FR FR8115835A patent/FR2492384B1/fr not_active Expired
- 1981-08-17 NL NL8103844A patent/NL8103844A/nl not_active Application Discontinuation
- 1981-08-17 IT IT23540/81A patent/IT1138154B/it active
- 1981-08-17 AT AT0358681A patent/AT376678B/de not_active IP Right Cessation
- 1981-08-17 SE SE8104877A patent/SE442116B/sv not_active IP Right Cessation
- 1981-08-17 GB GB8125029A patent/GB2086378B/en not_active Expired
- 1981-08-17 CH CH5313/81A patent/CH648320A5/de not_active IP Right Cessation
- 1981-08-17 JP JP56128642A patent/JPS5772992A/ja active Granted
- 1981-08-17 SU SU813320101A patent/SU1053757A3/ru active
- 1981-08-17 ES ES505310A patent/ES8300777A1/es not_active Expired
- 1981-08-17 IL IL63593A patent/IL63593A0/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56128643A (en) * | 1980-03-13 | 1981-10-08 | Sintokogio Ltd | Vertical flaskless type molding machine |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0321210U (fr) * | 1989-07-11 | 1991-03-01 |
Also Published As
| Publication number | Publication date |
|---|---|
| ATA358681A (de) | 1984-05-15 |
| SE442116B (sv) | 1985-12-02 |
| SU1053757A3 (ru) | 1983-11-07 |
| DE3132476A1 (de) | 1982-06-09 |
| IT8123540A0 (it) | 1981-08-17 |
| GB2086378B (en) | 1984-07-25 |
| CA1174672A (fr) | 1984-09-18 |
| CH648320A5 (de) | 1985-03-15 |
| FR2492384A1 (fr) | 1982-04-23 |
| NL8103844A (nl) | 1982-05-17 |
| GB2086378A (en) | 1982-05-12 |
| FR2492384B1 (fr) | 1986-04-04 |
| AT376678B (de) | 1984-12-27 |
| BE889989A (fr) | 1982-02-17 |
| DE3132476C2 (fr) | 1991-04-18 |
| ES505310A0 (es) | 1982-12-01 |
| SE8104877L (sv) | 1982-04-23 |
| JPS5772992A (en) | 1982-05-07 |
| HU181745B (en) | 1983-11-28 |
| IT1138154B (it) | 1986-09-17 |
| ES8300777A1 (es) | 1982-12-01 |
| IL63593A0 (en) | 1981-11-30 |
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