DD147543A5 - Verfahren zur herstellung von dimeren vincaalkaloiden - Google Patents
Verfahren zur herstellung von dimeren vincaalkaloiden Download PDFInfo
- Publication number
- DD147543A5 DD147543A5 DD79217285A DD21728579A DD147543A5 DD 147543 A5 DD147543 A5 DD 147543A5 DD 79217285 A DD79217285 A DD 79217285A DD 21728579 A DD21728579 A DD 21728579A DD 147543 A5 DD147543 A5 DD 147543A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- vlb
- ind2
- formula
- deacetyl
- diamine
- Prior art date
Links
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- 150000001298 alcohols Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 14
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- 238000002360 preparation method Methods 0.000 claims abstract description 11
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- 238000012986 modification Methods 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical class C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 230000001613 neoplastic effect Effects 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 210000002445 nipple Anatomy 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical class CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical class CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical class OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical class OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 1
- 150000003334 secondary amides Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- NGDIAZZSCVVCEW-UHFFFAOYSA-M sodium;butyl sulfate Chemical compound [Na+].CCCCOS([O-])(=O)=O NGDIAZZSCVVCEW-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical class OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- 229950003670 vinrosidine Drugs 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
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/905,667 US4199504A (en) | 1978-05-15 | 1978-05-15 | Bridged cathranthus alkaloid dimers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD147543A5 true DD147543A5 (de) | 1981-04-08 |
Family
ID=25421234
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79217285A DD147543A5 (de) | 1978-05-15 | 1979-05-15 | Verfahren zur herstellung von dimeren vincaalkaloiden |
| DD79217286A DD150467A5 (de) | 1978-05-15 | 1979-05-15 | Verfahren zur herstellung von dimeren vincaalkaloiden |
| DD79212894A DD143618A5 (de) | 1978-05-15 | 1979-05-15 | Verfahren zur herstellung von dimeren vincaalkaloiden |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79217286A DD150467A5 (de) | 1978-05-15 | 1979-05-15 | Verfahren zur herstellung von dimeren vincaalkaloiden |
| DD79212894A DD143618A5 (de) | 1978-05-15 | 1979-05-15 | Verfahren zur herstellung von dimeren vincaalkaloiden |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4199504A (cs) |
| EP (3) | EP0032756A3 (cs) |
| JP (1) | JPS54148798A (cs) |
| AU (1) | AU4691379A (cs) |
| BE (1) | BE876155A (cs) |
| CA (1) | CA1114816A (cs) |
| CS (1) | CS214792B2 (cs) |
| DD (3) | DD147543A5 (cs) |
| DK (1) | DK197579A (cs) |
| ES (3) | ES480560A1 (cs) |
| FI (1) | FI791519A7 (cs) |
| FR (2) | FR2435480A1 (cs) |
| GB (1) | GB2022080A (cs) |
| GR (1) | GR73047B (cs) |
| IL (1) | IL57434A0 (cs) |
| LU (1) | LU81254A1 (cs) |
| PH (3) | PH14999A (cs) |
| PL (2) | PL120896B1 (cs) |
| PT (1) | PT69589A (cs) |
| RO (1) | RO81682B (cs) |
| ZA (1) | ZA792271B (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4362664A (en) * | 1980-12-29 | 1982-12-07 | Eli Lilly And Company | Vinblastine oxazolidinedione disulfides and related compounds |
| DK167984A (da) * | 1983-03-30 | 1984-10-01 | Lilly Industries Ltd | Alkaloidderivater |
| AU5240999A (en) * | 1998-07-31 | 2000-02-21 | Goldsmith Seeds Inc. | Trimeric and polymeric alkaloids |
| EP1229934B1 (en) | 1999-10-01 | 2014-03-05 | Immunogen, Inc. | Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR204004A1 (es) * | 1973-04-02 | 1975-11-12 | Lilly Co Eli | Procedimientos para preparar derivados de vinblastina leurosidina y leurocristina |
| IL48685A (en) * | 1975-01-09 | 1980-03-31 | Lilly Co Eli | Amides of vincadioline and vinblastine |
| GR69783B (cs) * | 1976-09-08 | 1982-07-07 | Lilly Co Eli | |
| US4115388A (en) * | 1977-03-30 | 1978-09-19 | Eli Lilly And Company | 3'-Oxygenated derivatives of 4'-deoxy VLB "A" and "B" and related 1-formyl compounds |
| HU181874B (en) * | 1977-08-08 | 1983-11-28 | Lilly Co Eli | Process for preparing amides of deacetyl-leurosine and deacetyl-leuroformine |
-
1978
- 1978-05-15 US US05/905,667 patent/US4199504A/en not_active Expired - Lifetime
-
1979
- 1979-05-05 PH PH22464A patent/PH14999A/en unknown
- 1979-05-08 PT PT69589A patent/PT69589A/pt unknown
- 1979-05-09 AU AU46913/79A patent/AU4691379A/en not_active Abandoned
- 1979-05-10 FR FR7911882A patent/FR2435480A1/fr active Pending
- 1979-05-10 BE BE1/9386A patent/BE876155A/xx unknown
- 1979-05-10 ZA ZA792271A patent/ZA792271B/xx unknown
- 1979-05-10 CA CA327,351A patent/CA1114816A/en not_active Expired
- 1979-05-11 FI FI791519A patent/FI791519A7/fi not_active Application Discontinuation
- 1979-05-12 GR GR59071A patent/GR73047B/el unknown
- 1979-05-14 ES ES480560A patent/ES480560A1/es not_active Expired
- 1979-05-14 EP EP81101927A patent/EP0032756A3/en not_active Withdrawn
- 1979-05-14 RO RO97514A patent/RO81682B/ro unknown
- 1979-05-14 EP EP81101924A patent/EP0033981A3/en not_active Withdrawn
- 1979-05-14 ES ES480562A patent/ES480562A1/es not_active Expired
- 1979-05-14 ES ES480561A patent/ES480561A1/es not_active Expired
- 1979-05-14 DK DK197579A patent/DK197579A/da unknown
- 1979-05-14 JP JP5962979A patent/JPS54148798A/ja active Pending
- 1979-05-14 CS CS793284A patent/CS214792B2/cs unknown
- 1979-05-14 LU LU81254A patent/LU81254A1/xx unknown
- 1979-05-14 EP EP79300826A patent/EP0005620A1/en not_active Withdrawn
- 1979-05-14 GB GB7916702A patent/GB2022080A/en not_active Withdrawn
- 1979-05-15 PL PL1979222094A patent/PL120896B1/pl unknown
- 1979-05-15 DD DD79217285A patent/DD147543A5/de unknown
- 1979-05-15 DD DD79217286A patent/DD150467A5/de unknown
- 1979-05-15 PL PL21559379A patent/PL215593A1/xx unknown
- 1979-05-15 DD DD79212894A patent/DD143618A5/de unknown
- 1979-05-30 IL IL57434A patent/IL57434A0/xx unknown
- 1979-10-31 FR FR7926971A patent/FR2438052A1/fr active Pending
-
1980
- 1980-03-06 PH PH23730A patent/PH14907A/en unknown
- 1980-03-06 PH PH23731A patent/PH14904A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI791519A7 (fi) | 1981-01-01 |
| PT69589A (en) | 1979-06-01 |
| GR73047B (cs) | 1984-01-26 |
| EP0032756A3 (en) | 1981-09-09 |
| US4199504A (en) | 1980-04-22 |
| PL222094A1 (cs) | 1980-10-20 |
| AU4691379A (en) | 1979-11-22 |
| JPS54148798A (en) | 1979-11-21 |
| CA1114816A (en) | 1981-12-22 |
| RO81682B (ro) | 1983-04-30 |
| EP0032756A2 (en) | 1981-07-29 |
| CS214792B2 (en) | 1982-05-28 |
| IL57434A0 (en) | 1979-09-30 |
| DD150467A5 (de) | 1981-09-02 |
| FR2435480A1 (fr) | 1980-04-04 |
| EP0005620A1 (en) | 1979-11-28 |
| PH14907A (en) | 1982-01-29 |
| EP0033981A3 (en) | 1981-09-09 |
| PH14904A (en) | 1982-01-29 |
| PH14999A (en) | 1982-03-22 |
| RO81682A (ro) | 1983-04-29 |
| ES480562A1 (es) | 1980-04-01 |
| ES480560A1 (es) | 1980-04-01 |
| BE876155A (fr) | 1979-11-12 |
| DD143618A5 (de) | 1980-09-03 |
| GB2022080A (en) | 1979-12-12 |
| LU81254A1 (fr) | 1979-09-10 |
| FR2438052A1 (fr) | 1980-04-30 |
| PL120896B1 (en) | 1982-03-31 |
| EP0033981A2 (en) | 1981-08-19 |
| DK197579A (da) | 1979-11-16 |
| ZA792271B (en) | 1980-12-31 |
| PL215593A1 (cs) | 1980-06-16 |
| ES480561A1 (es) | 1980-04-01 |
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