CS195344B2 - Method of producing spirooxazolidindiones - Google Patents
Method of producing spirooxazolidindiones Download PDFInfo
- Publication number
- CS195344B2 CS195344B2 CS777940A CS794077A CS195344B2 CS 195344 B2 CS195344 B2 CS 195344B2 CS 777940 A CS777940 A CS 777940A CS 794077 A CS794077 A CS 794077A CS 195344 B2 CS195344 B2 CS 195344B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- vlb
- group
- derivatives
- compounds
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 6
- 239000012312 sodium hydride Substances 0.000 claims description 6
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 6
- 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 description 5
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 5
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- 239000002246 antineoplastic agent Substances 0.000 abstract description 3
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- 238000002156 mixing Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- OBEIXXHHUOSBLA-UQUCNHJPSA-N n-deformylvincristine 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)N3)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 OBEIXXHHUOSBLA-UQUCNHJPSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 231100000189 neurotoxic Toxicity 0.000 description 1
- 230000002887 neurotoxic effect Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical class CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 201000008968 osteosarcoma Diseases 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 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
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical class CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical class CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical class OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical class OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical class OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 229950003670 vinrosidine Drugs 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- GDJZZWYLFXAGFH-UHFFFAOYSA-M xylenesulfonate group Chemical group C1(C(C=CC=C1)C)(C)S(=O)(=O)[O-] GDJZZWYLFXAGFH-UHFFFAOYSA-M 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)
- Indole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (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 |
|---|---|
| CS195344B2 true CS195344B2 (en) | 1980-01-31 |
Family
ID=25005690
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS777940A CS195344B2 (en) | 1976-12-06 | 1977-11-30 | Method of producing spirooxazolidindiones |
| CS777939A CS195343B2 (en) | 1976-12-06 | 1977-11-30 | Method of producing derivatives of dimere indol-dihydro-indoldiones |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS777939A CS195343B2 (en) | 1976-12-06 | 1977-11-30 | Method of producing derivatives of dimere indol-dihydro-indoldiones |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US4096148A (en]) |
| JP (1) | JPS5371100A (en]) |
| AR (1) | AR218467A1 (en]) |
| AT (2) | AT353987B (en]) |
| AU (1) | AU513936B2 (en]) |
| BE (1) | BE861417A (en]) |
| BG (2) | BG33437A3 (en]) |
| CA (2) | CA1082180A (en]) |
| CH (2) | CH632516A5 (en]) |
| CS (2) | CS195344B2 (en]) |
| DD (2) | DD134227A5 (en]) |
| DE (1) | DE2753791A1 (en]) |
| DK (2) | DK145001C (en]) |
| ES (2) | ES464765A1 (en]) |
| FR (1) | FR2372839A1 (en]) |
| GB (1) | GB1590649A (en]) |
| GR (2) | GR67244B (en]) |
| HK (1) | HK57281A (en]) |
| HU (2) | HU180725B (en]) |
| IE (1) | IE46105B1 (en]) |
| IL (1) | IL53506A (en]) |
| MX (1) | MX4326E (en]) |
| MY (1) | MY8200176A (en]) |
| NL (1) | NL7713336A (en]) |
| NZ (1) | NZ185818A (en]) |
| PL (2) | PL110671B1 (en]) |
| PT (2) | PT67343B (en]) |
| RO (2) | RO75391A (en]) |
| SE (2) | SE435930B (en]) |
| SU (2) | SU865127A3 (en]) |
| ZA (1) | ZA777237B (en]) |
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 |
| HUT34212A (en) * | 1983-04-29 | 1985-02-28 | Omnichem Sa | Process for the production of new vindblastin conjugates |
| 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 (en]) * | 1960-05-24 | |||
| HU165986B (en]) * | 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 GR GR54898A patent/GR67244B/el unknown
- 1977-11-30 SE SE7713587A patent/SE435930B/sv not_active IP Right Cessation
- 1977-11-30 PT PT67343A patent/PT67343B/pt unknown
- 1977-11-30 RO RO7792261A patent/RO75391A/ro unknown
- 1977-11-30 CA CA292,101A patent/CA1082180A/en not_active Expired
- 1977-11-30 RO RO7792262A patent/RO74137A/ro unknown
- 1977-11-30 CS CS777940A patent/CS195344B2/cs unknown
- 1977-11-30 PT PT67342A patent/PT67342B/pt unknown
- 1977-11-30 CS CS777939A patent/CS195343B2/cs unknown
- 1977-11-30 CA CA292,072A patent/CA1103664A/en not_active Expired
- 1977-11-30 GB GB49906/77A patent/GB1590649A/en not_active Expired
- 1977-11-30 NZ NZ185818A patent/NZ185818A/xx unknown
- 1977-11-30 GR GR54897A patent/GR67243B/el unknown
- 1977-11-30 SE SE7713586A patent/SE436036B/sv not_active IP Right Cessation
- 1977-12-01 IL IL53506A patent/IL53506A/xx unknown
- 1977-12-01 NL NL7713336A patent/NL7713336A/xx not_active Application Discontinuation
- 1977-12-02 DE DE19772753791 patent/DE2753791A1/de active Granted
- 1977-12-02 FR FR7736437A patent/FR2372839A1/fr active Granted
- 1977-12-02 JP JP14561377A patent/JPS5371100A/ja active Granted
- 1977-12-02 BG BG037937A patent/BG33437A3/bg unknown
- 1977-12-02 BE BE1008557A patent/BE861417A/xx not_active IP Right Cessation
- 1977-12-02 BG BG037936A patent/BG33436A3/xx unknown
- 1977-12-05 IE IE2469/77A patent/IE46105B1/en unknown
- 1977-12-05 HU HU77EI7723A patent/HU180725B/hu not_active IP Right Cessation
- 1977-12-05 ES ES464765A patent/ES464765A1/es not_active Expired
- 1977-12-05 SU SU772549000A patent/SU865127A3/ru active
- 1977-12-05 MX MX776608U patent/MX4326E/es unknown
- 1977-12-05 AT AT868877A patent/AT353987B/de not_active IP Right Cessation
- 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 DK DK541077A patent/DK145001C/da not_active IP Right Cessation
- 1977-12-05 AU AU31230/77A patent/AU513936B2/en not_active Expired
- 1977-12-05 PL PL1977202659A patent/PL110671B1/pl unknown
- 1977-12-05 CH CH1486177A patent/CH634076A5/de not_active IP Right Cessation
- 1977-12-05 ZA ZA00777237A patent/ZA777237B/xx unknown
- 1977-12-05 HU HU77EI771A patent/HU180724B/hu not_active IP Right Cessation
- 1977-12-05 DK DK541177A patent/DK144916C/da not_active IP Right Cessation
- 1977-12-05 SU SU772549952A patent/SU843753A3/ru active
- 1977-12-05 PL PL1977202660A patent/PL106522B1/pl unknown
- 1977-12-05 AT AT868777A patent/AT361638B/de not_active IP Right Cessation
- 1977-12-06 DD DD77202423A patent/DD134227A5/xx unknown
- 1977-12-06 AR AR270267A patent/AR218467A1/es active
- 1977-12-06 DD DD77202424A patent/DD134228A5/xx unknown
-
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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