DK141511B - Analogifremgangsmåde til fremstilling af derivater af vindblastin, leurosidin eller leurocristin. - Google Patents
Analogifremgangsmåde til fremstilling af derivater af vindblastin, leurosidin eller leurocristin. Download PDFInfo
- Publication number
- DK141511B DK141511B DK178774AA DK178774A DK141511B DK 141511 B DK141511 B DK 141511B DK 178774A A DK178774A A DK 178774AA DK 178774 A DK178774 A DK 178774A DK 141511 B DK141511 B DK 141511B
- Authority
- DK
- Denmark
- Prior art keywords
- vinblastine
- desacetyl
- leurocristine
- carboxamide
- amide
- Prior art date
Links
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- 238000000034 method Methods 0.000 title description 39
- 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 title description 15
- 238000002360 preparation method Methods 0.000 title description 9
- JXLYSJRDGCGARV-KSNABSRWSA-N ac1l29ym 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-KSNABSRWSA-N 0.000 title description 8
- JXLYSJRDGCGARV-PJXZDTQASA-N Leurosidine 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-PJXZDTQASA-N 0.000 title description 7
- 230000008569 process Effects 0.000 title description 5
- RVCKCEDKBVEEHL-UHFFFAOYSA-N 2,3,4,5,6-pentachlorobenzyl alcohol Chemical compound OCC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl RVCKCEDKBVEEHL-UHFFFAOYSA-N 0.000 title 1
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- NDMPLJNOPCLANR-PETVRERISA-N deacetylvinblastine 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(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 NDMPLJNOPCLANR-PETVRERISA-N 0.000 description 41
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical class 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 40
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- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
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- 229940095102 methyl benzoate Drugs 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- ABMDIECEEGFXNC-UHFFFAOYSA-N n-ethylpropanamide Chemical compound CCNC(=O)CC ABMDIECEEGFXNC-UHFFFAOYSA-N 0.000 description 1
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 229950009215 phenylbutanoic acid Drugs 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 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
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229940066528 trichloroacetate Drugs 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- JXLYSJRDGCGARV-CFWMRBGOSA-N vinblastine 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-CFWMRBGOSA-N 0.000 description 1
- KDQAABAKXDWYSZ-PNYVAJAMSA-N vinblastine sulfate Chemical compound OS(O)(=O)=O.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 KDQAABAKXDWYSZ-PNYVAJAMSA-N 0.000 description 1
- 229960004982 vinblastine sulfate Drugs 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229940071104 xylenesulfonate Drugs 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)
- Health & Medical Sciences (AREA)
- Organic Chemistry (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 And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Fodder In General (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34727573A | 1973-04-02 | 1973-04-02 | |
| US34727573 | 1973-04-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK141511B true DK141511B (da) | 1980-04-08 |
| DK141511C DK141511C (en, 2012) | 1980-09-29 |
Family
ID=23363051
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK178774AA DK141511B (da) | 1973-04-02 | 1974-04-01 | Analogifremgangsmåde til fremstilling af derivater af vindblastin, leurosidin eller leurocristin. |
Country Status (28)
| Country | Link |
|---|---|
| JP (2) | JPS5919117B2 (en, 2012) |
| AR (2) | AR204004A1 (en, 2012) |
| AT (1) | AT340605B (en, 2012) |
| BE (1) | BE813168A (en, 2012) |
| BG (3) | BG22831A3 (en, 2012) |
| CA (1) | CA1042428A (en, 2012) |
| CH (1) | CH603669A5 (en, 2012) |
| CS (1) | CS185223B2 (en, 2012) |
| CY (1) | CY1044A (en, 2012) |
| DD (1) | DD113538A5 (en, 2012) |
| DE (1) | DE2415980A1 (en, 2012) |
| DK (1) | DK141511B (en, 2012) |
| ES (2) | ES424882A1 (en, 2012) |
| FR (1) | FR2223044B1 (en, 2012) |
| GB (1) | GB1463575A (en, 2012) |
| HK (1) | HK20180A (en, 2012) |
| HU (1) | HU171572B (en, 2012) |
| IE (1) | IE39071B1 (en, 2012) |
| IL (1) | IL44415A (en, 2012) |
| KE (1) | KE3028A (en, 2012) |
| MY (1) | MY8100025A (en, 2012) |
| NL (1) | NL181079C (en, 2012) |
| PH (1) | PH13623A (en, 2012) |
| RO (2) | RO73524B (en, 2012) |
| SE (1) | SE416206B (en, 2012) |
| SU (4) | SU731900A3 (en, 2012) |
| YU (3) | YU39719B (en, 2012) |
| ZA (1) | ZA741674B (en, 2012) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL48685A (en) * | 1975-01-09 | 1980-03-31 | Lilly Co Eli | Amides of vincadioline and vinblastine |
| GR69783B (en, 2012) * | 1976-09-08 | 1982-07-07 | Lilly Co Eli | |
| US4096148A (en) * | 1976-12-06 | 1978-06-20 | Eli Lilly And Company | Oxazolidinedione derivatives of Vinca alkaloids |
| USRE30561E (en) | 1976-12-06 | 1981-03-31 | Eli Lilly And Company | Vinca alkaloid intermediates |
| USRE30560E (en) * | 1976-12-06 | 1981-03-31 | Eli Lilly And Company | Oxazolidinedione derivatives of Vinca alkaloids |
| US4203898A (en) | 1977-08-29 | 1980-05-20 | Eli Lilly And Company | Amide derivatives of VLB, leurosidine, leurocristine and related dimeric alkaloids |
| US4199504A (en) * | 1978-05-15 | 1980-04-22 | Eli Lilly And Company | Bridged cathranthus alkaloid dimers |
| US4210584A (en) | 1979-01-15 | 1980-07-01 | Eli Lilly And Company | Vindesine synthesis |
| US4357334A (en) | 1980-03-20 | 1982-11-02 | Eli Lilly And Company | Use of VLB 3-(2-chloroethyl) carboxamide in treating neoplasms |
| OA06421A (fr) * | 1980-06-10 | 1981-09-30 | Omnium Chimique Sa | Procédé de préparation de dérivés N-(vinblastinoyl-23) d'acides aminés et de peptides. |
| LU83822A1 (fr) * | 1981-12-08 | 1983-09-01 | Omnichem Sa | Derives n-(vinblastinoyl-23)d'acides amines,leur preparation et leur application therapeutique |
| FR2623504B1 (fr) * | 1987-11-25 | 1990-03-09 | Adir | Nouveaux derives n-(vinblastinoyl-23) d'acide amino-1 methylphosphonique, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent |
| HUT76925A (hu) * | 1995-04-04 | 1998-01-28 | MTA Enzimológiai Intézet | Bisz-indol-származékok, eljárás előállításukra és az azokat tartalmazó gyógyszerkészítmények |
| US5948750A (en) * | 1996-10-30 | 1999-09-07 | Merck & Co., Inc. | Conjugates useful in the treatment of prostate cancer |
| US6326402B1 (en) | 1998-08-12 | 2001-12-04 | Octamer, Inc. | Methods for treating viral infections using a compound capable of inhibiting microtubules |
| AU2006207321B2 (en) | 2005-01-21 | 2012-09-06 | Astex Therapeutics Limited | Pharmaceutical compounds |
| RU2447889C2 (ru) | 2005-07-18 | 2012-04-20 | Бипар Сайенсиз, Инк. | Способ лечения рака (варианты) |
| US8143447B2 (en) | 2006-09-05 | 2012-03-27 | Bipar Sciences, Inc. | Treatment of cancer |
| CN101534836B (zh) | 2006-09-05 | 2011-09-28 | 彼帕科学公司 | Parp抑制剂在制备治疗肥胖症的药物中的用途 |
| EP2073807A1 (en) | 2006-10-12 | 2009-07-01 | Astex Therapeutics Limited | Pharmaceutical combinations |
| EP2073803B1 (en) | 2006-10-12 | 2018-09-19 | Astex Therapeutics Limited | Pharmaceutical combinations |
| EP2217227B1 (en) | 2007-11-12 | 2013-08-21 | BiPar Sciences, Inc. | Treatment of breast cancer with 4-iodo-3-nitrobenzamide in combination with anti-tumor agents |
| WO2014169697A1 (zh) * | 2013-04-19 | 2014-10-23 | 暨南大学 | 长春碱类衍生物及其制备方法和应用 |
| CN113456797B (zh) * | 2021-06-18 | 2024-03-08 | 暨南大学 | 长春碱类衍生物在制备治疗骨肉瘤和/或软组织肉瘤药物中的应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3097137A (en) * | 1960-05-19 | 1963-07-09 | Canadian Patents Dev | Vincaleukoblastine |
-
1974
- 1974-01-01 AR AR253105A patent/AR204004A1/es active
- 1974-03-13 ZA ZA00741674A patent/ZA741674B/xx unknown
- 1974-03-13 IL IL44415A patent/IL44415A/xx unknown
- 1974-03-13 IE IE532/74A patent/IE39071B1/xx unknown
- 1974-03-22 CA CA195,760A patent/CA1042428A/en not_active Expired
- 1974-03-25 YU YU817/74A patent/YU39719B/xx unknown
- 1974-03-25 GB GB1310174A patent/GB1463575A/en not_active Expired
- 1974-03-25 CY CY1044A patent/CY1044A/xx unknown
- 1974-03-29 CH CH446374A patent/CH603669A5/xx not_active IP Right Cessation
- 1974-03-29 PH PH15676A patent/PH13623A/en unknown
- 1974-03-29 FR FR7411519A patent/FR2223044B1/fr not_active Expired
- 1974-04-01 NL NLAANVRAGE7404423,A patent/NL181079C/xx not_active IP Right Cessation
- 1974-04-01 HU HU74EI00000538A patent/HU171572B/hu unknown
- 1974-04-01 DK DK178774AA patent/DK141511B/da not_active IP Right Cessation
- 1974-04-01 CS CS7400002335A patent/CS185223B2/cs unknown
- 1974-04-01 SE SE7404380A patent/SE416206B/xx not_active IP Right Cessation
- 1974-04-01 SU SU742013753A patent/SU731900A3/ru active
- 1974-04-01 AT AT267974A patent/AT340605B/de not_active IP Right Cessation
- 1974-04-02 ES ES424882A patent/ES424882A1/es not_active Expired
- 1974-04-02 DD DD177632A patent/DD113538A5/xx unknown
- 1974-04-02 RO RO78274A patent/RO73524B/ro unknown
- 1974-04-02 DE DE2415980A patent/DE2415980A1/de active Granted
- 1974-04-02 BG BG026279A patent/BG22831A3/xx unknown
- 1974-04-02 BG BG028513A patent/BG21612A3/xx unknown
- 1974-04-02 JP JP49037765A patent/JPS5919117B2/ja not_active Expired
- 1974-04-02 BG BG028514A patent/BG21235A3/xx unknown
- 1974-04-02 BE BE1005847A patent/BE813168A/xx not_active IP Right Cessation
- 1974-04-02 RO RO7498695A patent/RO77533A/ro unknown
-
1975
- 1975-01-08 AR AR257228A patent/AR203882A1/es active
- 1975-07-04 SU SU752151512A patent/SU784783A3/ru active
- 1975-07-09 SU SU752152020A patent/SU652896A3/ru active
-
1976
- 1976-03-31 ES ES446571A patent/ES446571A1/es not_active Expired
- 1976-12-20 SU SU762429453A patent/SU623522A3/ru active
-
1980
- 1980-02-27 KE KE3028A patent/KE3028A/xx unknown
- 1980-04-17 HK HK201/80A patent/HK20180A/xx unknown
- 1980-04-25 YU YU1138/80A patent/YU39875B/xx unknown
- 1980-04-25 YU YU1139/80A patent/YU39876B/xx unknown
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1981
- 1981-12-30 MY MY25/81A patent/MY8100025A/xx unknown
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1983
- 1983-12-16 JP JP58238722A patent/JPS6033837B2/ja not_active Expired
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| Date | Code | Title | Description |
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| PUP | Patent expired |