SU865127A3 - Способ получени спирооксазолидиндионов - Google Patents
Способ получени спирооксазолидиндионов Download PDFInfo
- Publication number
- SU865127A3 SU865127A3 SU772549000A SU2549000A SU865127A3 SU 865127 A3 SU865127 A3 SU 865127A3 SU 772549000 A SU772549000 A SU 772549000A SU 2549000 A SU2549000 A SU 2549000A SU 865127 A3 SU865127 A3 SU 865127A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- spirooxazolidinediones
- preparing
- formula
- spiro
- general formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 4
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- 239000012312 sodium hydride Substances 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 abstract description 2
- 229940122803 Vinca alkaloid Drugs 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229930013930 alkaloid Natural products 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000001475 oxazolidinediones Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- IEWSUUSSJFUSBS-UHFFFAOYSA-N 3a,4-dihydro-1H-indole-2,3-dione 1H-indole Chemical compound N1C(C(C2CC=CC=C12)=O)=O.N1C=CC2=CC=CC=C12 IEWSUUSSJFUSBS-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 240000001829 Catharanthus roseus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010039740 Screaming Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000863480 Vinca Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000000266 alpha-aminoacyl group Chemical group 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/747,575 US4096148A (en) | 1976-12-06 | 1976-12-06 | Oxazolidinedione derivatives of Vinca alkaloids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU865127A3 true SU865127A3 (ru) | 1981-09-15 |
Family
ID=25005690
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772549000A SU865127A3 (ru) | 1976-12-06 | 1977-12-05 | Способ получени спирооксазолидиндионов |
| SU772549952A SU843753A3 (ru) | 1976-12-06 | 1977-12-05 | Способ получени димерных индолдигидроиндолдионовых соединений |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772549952A SU843753A3 (ru) | 1976-12-06 | 1977-12-05 | Способ получени димерных индолдигидроиндолдионовых соединений |
Country Status (31)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU181874B (en) * | 1977-08-08 | 1983-11-28 | Lilly Co Eli | Process for preparing amides of deacetyl-leurosine and deacetyl-leuroformine |
| US4357334A (en) * | 1980-03-20 | 1982-11-02 | Eli Lilly And Company | Use of VLB 3-(2-chloroethyl) carboxamide in treating neoplasms |
| US4362664A (en) * | 1980-12-29 | 1982-12-07 | Eli Lilly And Company | Vinblastine oxazolidinedione disulfides and related compounds |
| GR81790B (cg-RX-API-DMAC7.html) * | 1983-04-29 | 1984-12-12 | Omnichem Sa | |
| HUT76925A (hu) * | 1995-04-04 | 1998-01-28 | MTA Enzimológiai Intézet | Bisz-indol-származékok, eljárás előállításukra és az azokat tartalmazó gyógyszerkészítmények |
| JP4776843B2 (ja) | 1999-10-01 | 2011-09-21 | イムノゲン インコーポレーティッド | 免疫複合体及び化学療法剤を用いる癌治療用組成物及び方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT649883A (cg-RX-API-DMAC7.html) * | 1960-05-24 | |||
| HU165986B (cg-RX-API-DMAC7.html) * | 1973-02-16 | 1974-12-28 | ||
| AR204004A1 (es) * | 1973-04-02 | 1975-11-12 | Lilly Co Eli | Procedimientos para preparar derivados de vinblastina leurosidina y leurocristina |
| US4012390A (en) * | 1974-10-16 | 1977-03-15 | Eli Lilly And Company | Vinblastinoic acid |
-
1976
- 1976-12-06 US US05/747,575 patent/US4096148A/en not_active Expired - Lifetime
-
1977
- 1977-11-30 CS CS777939A patent/CS195343B2/cs unknown
- 1977-11-30 CA CA292,101A patent/CA1082180A/en not_active Expired
- 1977-11-30 NZ NZ185818A patent/NZ185818A/xx unknown
- 1977-11-30 SE SE7713587A patent/SE435930B/sv not_active IP Right Cessation
- 1977-11-30 GB GB49906/77A patent/GB1590649A/en not_active Expired
- 1977-11-30 GR GR54897A patent/GR67243B/el unknown
- 1977-11-30 RO RO7792262A patent/RO74137A/ro unknown
- 1977-11-30 SE SE7713586A patent/SE436036B/sv not_active IP Right Cessation
- 1977-11-30 RO RO7792261A patent/RO75391A/ro unknown
- 1977-11-30 PT PT67343A patent/PT67343B/pt unknown
- 1977-11-30 PT PT67342A patent/PT67342B/pt unknown
- 1977-11-30 GR GR54898A patent/GR67244B/el unknown
- 1977-11-30 CA CA292,072A patent/CA1103664A/en not_active Expired
- 1977-11-30 CS CS777940A patent/CS195344B2/cs unknown
- 1977-12-01 IL IL53506A patent/IL53506A/xx unknown
- 1977-12-01 NL NL7713336A patent/NL7713336A/xx not_active Application Discontinuation
- 1977-12-02 BG BG037937A patent/BG33437A3/bg unknown
- 1977-12-02 JP JP14561377A patent/JPS5371100A/ja active Granted
- 1977-12-02 DE DE19772753791 patent/DE2753791A1/de active Granted
- 1977-12-02 BG BG037936A patent/BG33436A3/xx unknown
- 1977-12-02 BE BE1008557A patent/BE861417A/xx not_active IP Right Cessation
- 1977-12-02 FR FR7736437A patent/FR2372839A1/fr active Granted
- 1977-12-05 HU HU77EI7723A patent/HU180725B/hu not_active IP Right Cessation
- 1977-12-05 HU HU77EI771A patent/HU180724B/hu not_active IP Right Cessation
- 1977-12-05 MX MX776608U patent/MX4326E/es unknown
- 1977-12-05 ES ES464764A patent/ES464764A1/es not_active Expired
- 1977-12-05 CH CH1486277A patent/CH632516A5/de not_active IP Right Cessation
- 1977-12-05 SU SU772549000A patent/SU865127A3/ru active
- 1977-12-05 PL PL1977202660A patent/PL106522B1/pl unknown
- 1977-12-05 AT AT868777A patent/AT361638B/de not_active IP Right Cessation
- 1977-12-05 IE IE2469/77A patent/IE46105B1/en unknown
- 1977-12-05 DK DK541177A patent/DK144916C/da not_active IP Right Cessation
- 1977-12-05 AU AU31230/77A patent/AU513936B2/en not_active Expired
- 1977-12-05 CH CH1486177A patent/CH634076A5/de not_active IP Right Cessation
- 1977-12-05 AT AT868877A patent/AT353987B/de not_active IP Right Cessation
- 1977-12-05 SU SU772549952A patent/SU843753A3/ru active
- 1977-12-05 ZA ZA00777237A patent/ZA777237B/xx unknown
- 1977-12-05 DK DK541077A patent/DK145001C/da not_active IP Right Cessation
- 1977-12-05 PL PL1977202659A patent/PL110671B1/pl unknown
- 1977-12-05 ES ES464765A patent/ES464765A1/es not_active Expired
- 1977-12-06 DD DD77202424A patent/DD134228A5/xx unknown
- 1977-12-06 DD DD77202423A patent/DD134227A5/xx unknown
- 1977-12-06 AR AR270267A patent/AR218467A1/es active
-
1981
- 1981-11-19 HK HK572/81A patent/HK57281A/xx unknown
-
1982
- 1982-12-30 MY MY176/82A patent/MY8200176A/xx unknown
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