ES479753A1 - Un procedimiento para la preparacion de una carboxihidrazidac-3 de 4-desacetil-vincaleucoblastina. - Google Patents
Un procedimiento para la preparacion de una carboxihidrazidac-3 de 4-desacetil-vincaleucoblastina.Info
- Publication number
- ES479753A1 ES479753A1 ES479753A ES479753A ES479753A1 ES 479753 A1 ES479753 A1 ES 479753A1 ES 479753 A ES479753 A ES 479753A ES 479753 A ES479753 A ES 479753A ES 479753 A1 ES479753 A1 ES 479753A1
- Authority
- ES
- Spain
- Prior art keywords
- alkaloids
- vlb
- carboxhydrazides
- treatment
- preparation
- 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
- 238000009472 formulation Methods 0.000 title 1
- 239000000203 mixture Substances 0.000 title 1
- 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 abstract 5
- 229930013930 alkaloid Natural products 0.000 abstract 3
- 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 abstract 3
- LPGWZGMPDKDHEP-HLTPFJCJSA-N Leurosine Chemical compound C([C@]1([C@@H]2O1)CC)N(CCC=1C3=CC=CC=C3NC=11)C[C@H]2C[C@]1(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC LPGWZGMPDKDHEP-HLTPFJCJSA-N 0.000 abstract 2
- 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 abstract 2
- 201000010099 disease Diseases 0.000 abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 2
- 229960003048 vinblastine Drugs 0.000 abstract 2
- 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 abstract 2
- 240000001829 Catharanthus roseus Species 0.000 abstract 1
- 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 abstract 1
- LPGWZGMPDKDHEP-GKWAKPNHSA-N Leurosine 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@]6(CC)O[C@@H]6[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C LPGWZGMPDKDHEP-GKWAKPNHSA-N 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 abstract 1
- 201000011510 cancer Diseases 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 230000003211 malignant effect Effects 0.000 abstract 1
- 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 abstract 1
- 229960004528 vincristine Drugs 0.000 abstract 1
- 229950003670 vinrosidine Drugs 0.000 abstract 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Saccharide Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Alcaloides naturales que se obtienen de la Vinca rosea son activos en el tratamiento de los tumores malignos experimentales de los animales. Entre estos se encuentran la leurosina, la vincaleucoblastina (vinblastina) a la que nos referiremos en adelante com oVLB, leuroformina, leurosidina (vinrosidina) y leurocristina; desoxi VLB "A" y "B", Tetrahedron Letters; 4-desacetoxivinblastina; 4-desacetoxi-3''-hidroxivinblastina; leurocolombina y vincadiolina. Dos de estos alcaloides, VLB y vincristina, son ahora comercializados como fármacos para el tratamiento de las enfermedades malignas, especialmente las leucemis y enfermedades similares en el hombre. Los dos alcaloides comercializados son habitualmente administrados por vía intravenosa.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/899,032 US4166810A (en) | 1978-04-20 | 1978-04-20 | Derivatives of 4-desacetyl VLB C-3 carboxyhydrazide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES479753A1 true ES479753A1 (es) | 1980-08-16 |
Family
ID=25410402
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES479754A Expired ES479754A1 (es) | 1978-04-20 | 1979-04-19 | Un procedimiento para la preparacion de una carboxihidrazidac-3 de 4-desacetil-vincaleucoblastina. |
| ES479753A Expired ES479753A1 (es) | 1978-04-20 | 1979-04-19 | Un procedimiento para la preparacion de una carboxihidrazidac-3 de 4-desacetil-vincaleucoblastina. |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES479754A Expired ES479754A1 (es) | 1978-04-20 | 1979-04-19 | Un procedimiento para la preparacion de una carboxihidrazidac-3 de 4-desacetil-vincaleucoblastina. |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US4166810A (es) |
| EP (1) | EP0005051B1 (es) |
| JP (1) | JPS54141798A (es) |
| AR (1) | AR228940A1 (es) |
| AT (1) | AT369010B (es) |
| AU (1) | AU527109B2 (es) |
| BE (1) | BE875652A (es) |
| BG (3) | BG33297A3 (es) |
| CA (1) | CA1097629A (es) |
| CH (1) | CH643269A5 (es) |
| CS (3) | CS218584B2 (es) |
| DD (1) | DD143075A5 (es) |
| DE (1) | DE2964130D1 (es) |
| DK (1) | DK147484C (es) |
| EG (1) | EG14867A (es) |
| ES (2) | ES479754A1 (es) |
| FI (1) | FI791286A7 (es) |
| FR (1) | FR2423495A1 (es) |
| GB (1) | GB2019396B (es) |
| GR (1) | GR69987B (es) |
| HU (1) | HU181431B (es) |
| IE (1) | IE48213B1 (es) |
| IL (1) | IL57168A (es) |
| LU (1) | LU81166A1 (es) |
| NZ (1) | NZ190213A (es) |
| PH (1) | PH14163A (es) |
| PL (3) | PL125470B1 (es) |
| PT (1) | PT69496A (es) |
| RO (3) | RO81037A (es) |
| SU (3) | SU893135A3 (es) |
| YU (1) | YU93179A (es) |
| ZA (1) | ZA791856B (es) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4322351A (en) * | 1980-08-25 | 1982-03-30 | Eli Lilly And Company | Antineoplastic 4'-formylamino and 4'-acetylamino VLB, and derivatives thereof |
| ATE57187T1 (de) * | 1983-03-30 | 1990-10-15 | Lilly Industries Ltd | Vincaleukoblastin-derivate. |
| US4675400A (en) * | 1985-06-17 | 1987-06-23 | Eli Lilly And Company | Bifunctional derivatives of 4-desacetyl indole-dihydroindole alkaloids |
| US4667030A (en) * | 1985-06-17 | 1987-05-19 | Eli Lilly And Company | Hydrazide succinimide derivatives of antineoplastic indole-dihydroindole alkaloids |
| US4801688A (en) * | 1986-05-27 | 1989-01-31 | Eli Lilly And Company | Hydrazone immunoglobulin conjugates |
| US5043336A (en) * | 1990-04-03 | 1991-08-27 | Eli Lilly And Company | Cyclic imide derivatives of 4-desacetyl VLB c-3 carboxhydrazide |
| US5043340A (en) * | 1990-04-03 | 1991-08-27 | Eli Lilly And Company | Derivatives of 4-desacetyl VLB C-3 carboxhydrazide |
| EP1389209B1 (en) * | 2001-04-24 | 2009-04-08 | Purdue Research Foundation | Folate mimetics and folate-receptor binding conjugates thereof |
| ES2324708T3 (es) * | 2002-05-15 | 2009-08-13 | Endocyte, Inc. | Conjugados de vitamina-mitomicina. |
| EP1592457B1 (en) | 2003-01-27 | 2012-07-25 | Endocyte, Inc. | Folate-vinblastine conjugate as medicament |
| US8288557B2 (en) * | 2004-07-23 | 2012-10-16 | Endocyte, Inc. | Bivalent linkers and conjugates thereof |
| CN101175757B (zh) * | 2005-03-16 | 2012-11-14 | 恩多塞特公司 | 蝶酸及其缀合物的合成和纯化 |
| CN103893779A (zh) | 2005-08-19 | 2014-07-02 | 恩多塞特公司 | 多药物配体缀合物 |
| EP1948240A2 (en) * | 2005-08-19 | 2008-07-30 | Endocyte, Inc. | Ligand conjugates of vinca alkaloids, analogs and derivatives |
| US20100087370A1 (en) * | 2007-02-14 | 2010-04-08 | The General Hospital Corporation | Modulation of nitric oxide signaling to normalize tumor vasculature |
| US20100104626A1 (en) * | 2007-02-16 | 2010-04-29 | Endocyte, Inc. | Methods and compositions for treating and diagnosing kidney disease |
| CN101678124A (zh) * | 2007-03-14 | 2010-03-24 | 恩多塞特公司 | 结合配体连接的微管溶素递药缀合物 |
| US9877965B2 (en) | 2007-06-25 | 2018-01-30 | Endocyte, Inc. | Vitamin receptor drug delivery conjugates for treating inflammation |
| CN104383553A (zh) | 2007-06-25 | 2015-03-04 | 恩多塞特公司 | 含有亲水性间隔区接头的共轭物 |
| AU2008316835B2 (en) * | 2007-10-25 | 2015-07-16 | Endocyte, Inc. | Tubulysins and processes for preparing |
| JP5780961B2 (ja) * | 2009-09-07 | 2015-09-16 | ニプロパッチ株式会社 | 経皮吸収型製剤 |
| US10080805B2 (en) | 2012-02-24 | 2018-09-25 | Purdue Research Foundation | Cholecystokinin B receptor targeting for imaging and therapy |
| US20140080175A1 (en) | 2012-03-29 | 2014-03-20 | Endocyte, Inc. | Processes for preparing tubulysin derivatives and conjugates thereof |
| US9662402B2 (en) | 2012-10-16 | 2017-05-30 | Endocyte, Inc. | Drug delivery conjugates containing unnatural amino acids and methods for using |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3097137A (en) * | 1960-05-19 | 1963-07-09 | Canadian Patents Dev | Vincaleukoblastine |
| US3205220A (en) * | 1961-10-26 | 1965-09-07 | Lilly Co Eli | Leurosidine and leurocristine and their production |
| US3392173A (en) * | 1964-03-09 | 1968-07-09 | Lilly Co Eli | Novel acyl derivatives of desacetyl-vincaleukoblastine and processes for their preparation |
| US3370057A (en) * | 1964-04-27 | 1968-02-20 | Lilly Co Eli | Leurosine |
| US3387001A (en) * | 1964-10-19 | 1968-06-04 | Lilly Co Eli | Novel aminoacyl esters of desacetyl vincaleukoblastine |
| US3887565A (en) * | 1974-05-06 | 1975-06-03 | Lilly Co Eli | Vincadioline |
| US3890325A (en) * | 1974-05-15 | 1975-06-17 | Lilly Co Eli | Leurocolombine |
| US3954773A (en) * | 1974-11-21 | 1976-05-04 | Eli Lilly And Company | 4-Desacetoxyvinblastine |
| US3944554A (en) * | 1975-01-09 | 1976-03-16 | Eli Lilly And Company | 4-Desacetoxy-3-hydroxyvinblastine |
| IL48685A (en) | 1975-01-09 | 1980-03-31 | Lilly Co Eli | Amides of vincadioline and vinblastine |
| US4029663A (en) * | 1975-07-10 | 1977-06-14 | Eli Lilly And Company | Dimeric anhydro-vinca derivatives |
| 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 |
-
1978
- 1978-04-20 US US05/899,032 patent/US4166810A/en not_active Expired - Lifetime
-
1979
- 1979-04-17 JP JP4715279A patent/JPS54141798A/ja active Granted
- 1979-04-17 PH PH23391A patent/PH14163A/en unknown
- 1979-04-17 PT PT69496A patent/PT69496A/pt unknown
- 1979-04-18 BE BE1/9358A patent/BE875652A/xx unknown
- 1979-04-18 YU YU00931/79A patent/YU93179A/xx unknown
- 1979-04-18 AT AT0291279A patent/AT369010B/de not_active IP Right Cessation
- 1979-04-18 NZ NZ190213A patent/NZ190213A/xx unknown
- 1979-04-18 EP EP79300638A patent/EP0005051B1/en not_active Expired
- 1979-04-18 RO RO79102377A patent/RO81037A/ro unknown
- 1979-04-18 GR GR58950A patent/GR69987B/el unknown
- 1979-04-18 GB GB7913460A patent/GB2019396B/en not_active Expired
- 1979-04-18 RO RO7997290A patent/RO80084A/ro unknown
- 1979-04-18 EG EG238/79A patent/EG14867A/xx active
- 1979-04-18 RO RO79102376A patent/RO81114A/ro unknown
- 1979-04-18 LU LU81166A patent/LU81166A1/xx unknown
- 1979-04-18 AU AU46097/79A patent/AU527109B2/en not_active Ceased
- 1979-04-18 DE DE7979300638T patent/DE2964130D1/de not_active Expired
- 1979-04-19 ES ES479754A patent/ES479754A1/es not_active Expired
- 1979-04-19 CH CH370779A patent/CH643269A5/fr not_active IP Right Cessation
- 1979-04-19 PL PL1979230538A patent/PL125470B1/pl unknown
- 1979-04-19 FI FI791286A patent/FI791286A7/fi not_active Application Discontinuation
- 1979-04-19 CS CS807545A patent/CS218584B2/cs unknown
- 1979-04-19 CS CS807546A patent/CS218585B2/cs unknown
- 1979-04-19 PL PL21591179A patent/PL215911A1/xx unknown
- 1979-04-19 ZA ZA791856A patent/ZA791856B/xx unknown
- 1979-04-19 ES ES479753A patent/ES479753A1/es not_active Expired
- 1979-04-19 CS CS792678A patent/CS218583B2/cs unknown
- 1979-04-19 CA CA325,844A patent/CA1097629A/en not_active Expired
- 1979-04-19 HU HU79EI850A patent/HU181431B/hu not_active IP Right Cessation
- 1979-04-19 FR FR7909874A patent/FR2423495A1/fr active Granted
- 1979-04-19 DK DK160679A patent/DK147484C/da not_active IP Right Cessation
- 1979-04-19 PL PL1979215011A patent/PL119416B1/pl unknown
- 1979-04-20 DD DD79212369A patent/DD143075A5/de unknown
- 1979-04-20 AR AR276248A patent/AR228940A1/es active
- 1979-04-20 BG BG056470A patent/BG33297A3/xx unknown
- 1979-04-20 BG BG056469A patent/BG33296A3/xx unknown
- 1979-04-20 SU SU792759650A patent/SU893135A3/ru active
- 1979-04-20 SU SU792925606A patent/SU1225490A3/ru active
- 1979-04-20 BG BG043323A patent/BG33294A3/xx unknown
- 1979-04-29 IL IL57168A patent/IL57168A/xx unknown
- 1979-08-08 IE IE795/79A patent/IE48213B1/en unknown
-
1980
- 1980-05-26 SU SU802925605A patent/SU1061698A3/ru active
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD1A | Patent lapsed |
Effective date: 20001204 |