FR2434172A1 - Antitumour vinblastine and vincristine derivs. - e.g. 5'-nor-anhydro-vinblastine or vincristine, 5'-nor-leurosine and 12-chloro derivs. (J5 5.3.80) - Google Patents
Antitumour vinblastine and vincristine derivs. - e.g. 5'-nor-anhydro-vinblastine or vincristine, 5'-nor-leurosine and 12-chloro derivs. (J5 5.3.80)Info
- Publication number
- FR2434172A1 FR2434172A1 FR7824569A FR7824569A FR2434172A1 FR 2434172 A1 FR2434172 A1 FR 2434172A1 FR 7824569 A FR7824569 A FR 7824569A FR 7824569 A FR7824569 A FR 7824569A FR 2434172 A1 FR2434172 A1 FR 2434172A1
- Authority
- FR
- France
- Prior art keywords
- derivs
- vinblastine
- vincristine
- hydroxy
- alkanoyloxy
- 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.)
- Granted
Links
- 229960004528 vincristine Drugs 0.000 title abstract 3
- 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 abstract 3
- 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 title abstract 3
- 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 title abstract 2
- 230000000259 anti-tumor effect Effects 0.000 title abstract 2
- 229960003048 vinblastine Drugs 0.000 title abstract 2
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine 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-XQKSVPLYSA-N 0.000 title abstract 2
- GBABOYUKABKIAF-IELIFDKJSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(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 GBABOYUKABKIAF-IELIFDKJSA-N 0.000 title 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 5
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 abstract 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000005042 acyloxymethyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000003863 ammonium salts Chemical class 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 abstract 1
- -1 acetamido, hydroxymethyl Chemical group 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000005252 haloacyl group Chemical group 0.000 abstract 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 1
- 238000010253 intravenous injection Methods 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
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (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)
Abstract
(a) Vinblastine or vincristine derivs. of formula (I) and their acid addition and quat. ammonium salts and their acid addition and quat. ammonium salts and their 12-chloro derivs. are new. In (I), Qis a gp. (II) R'1 = H, alkoxy, acyl, formyl or haloacyl; R'2=H or alkyl; R'3,R"3 independently = H, hydroxy, alkanoyloxy or together = O or R'3 and R'5=-O- or form a second bond; R'4=H, alkoxycarbonyl, hydroxymethyl, alkanoyloxymethyl or acetamido; R'5, R"5 independently = H, hydroxy, alkanoyloxy, ethyl or 2-hydroxyethyl; R'6 = H, ethyl, 2-hydroxy-ethyl or acetyl. R1=H, alkyl, formyl or acyl; R2=H or alkoxy; R3=H hydroxy, or alkanoyloxy or R3 and R4 together = -O- or form a second bond; R4 = H, hydroxy, alkanoyloxy or R4 and R5 together = -O- R6 - alkoxycarbonyl, hydrazido, acetamido, hydroxymethyl or alkanoyloxymethyl; R5, R7=H, hydroxy or alkanoyloxy; R8 is H. (I) are antitumour agents which are prepd. administered parenterally esp. by i.v. injection in daily doses of 10-20 mg. for adults.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7824569A FR2434172A1 (en) | 1978-08-24 | 1978-08-24 | Antitumour vinblastine and vincristine derivs. - e.g. 5'-nor-anhydro-vinblastine or vincristine, 5'-nor-leurosine and 12-chloro derivs. (J5 5.3.80) |
| US06/067,439 US4307100A (en) | 1978-08-24 | 1979-08-20 | Nor bis-indole compounds usable as medicaments |
| CA000334286A CA1136129A (en) | 1978-08-24 | 1979-08-22 | Intermediates used for the synthesis of bis-indolic derivatives and process for their preparation |
| HU79RE655A HU182988B (en) | 1978-08-24 | 1979-08-22 | Process for preparing bis-indole compounds |
| JP10704579A JPS5531096A (en) | 1978-08-24 | 1979-08-22 | Novel compound bissindoline derivative active as drug and its manufacture |
| DE7979400585T DE2966049D1 (en) | 1978-08-24 | 1979-08-23 | Bis-indole compounds, pharmaceutical compositions containing them, process for their preparation |
| EP79400585A EP0010458B1 (en) | 1978-08-24 | 1979-08-23 | Bis-indole compounds, pharmaceutical compositions containing them, process for their preparation |
| NL990027C NL990027I2 (en) | 1978-08-24 | 1999-08-20 | Bisindole compounds, pharmaceutical preparations containing them and process for their preparation. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7824569A FR2434172A1 (en) | 1978-08-24 | 1978-08-24 | Antitumour vinblastine and vincristine derivs. - e.g. 5'-nor-anhydro-vinblastine or vincristine, 5'-nor-leurosine and 12-chloro derivs. (J5 5.3.80) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2434172A1 true FR2434172A1 (en) | 1980-03-21 |
| FR2434172B1 FR2434172B1 (en) | 1981-01-30 |
Family
ID=9212050
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7824569A Granted FR2434172A1 (en) | 1978-08-24 | 1978-08-24 | Antitumour vinblastine and vincristine derivs. - e.g. 5'-nor-anhydro-vinblastine or vincristine, 5'-nor-leurosine and 12-chloro derivs. (J5 5.3.80) |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS5531096A (en) |
| FR (1) | FR2434172A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0022730A1 (en) * | 1979-07-17 | 1981-01-21 | ANVAR Agence Nationale de Valorisation de la Recherche | Class of bis-indole compounds useful as medicines, and process for their preparation |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000036046A1 (en) | 1998-12-12 | 2000-06-22 | Solvay (Societe Anonyme) | Compositions comprising 1,1,1,3,3-pentafluorobutane and use of said compositions |
| EP1989212B1 (en) * | 2006-02-17 | 2013-06-19 | Cascade Prodrug Inc. | Treatment of hyperproliferative diseases with vinca alkaloid n-oxide and analogs |
| CN101235046B (en) * | 2007-01-29 | 2010-09-08 | 中国科学院上海药物研究所 | Vinblastine derivative, its preparation method and use, and pharmaceutical composition containing the derivative |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1435519A (en) * | 1964-06-18 | 1966-04-15 | Lilly Co Eli | Indolylvindoline and method of preparation |
-
1978
- 1978-08-24 FR FR7824569A patent/FR2434172A1/en active Granted
-
1979
- 1979-08-22 JP JP10704579A patent/JPS5531096A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1435519A (en) * | 1964-06-18 | 1966-04-15 | Lilly Co Eli | Indolylvindoline and method of preparation |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0022730A1 (en) * | 1979-07-17 | 1981-01-21 | ANVAR Agence Nationale de Valorisation de la Recherche | Class of bis-indole compounds useful as medicines, and process for their preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2434172B1 (en) | 1981-01-30 |
| JPS5531096A (en) | 1980-03-05 |
| JPS6332795B2 (en) | 1988-07-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CC | Supplementary protection certificate (spc) laid open to the public (law of 25 june 1990) |
Free format text: 92C0390, 920604 |
|
| CB | Supplementary protection certificate (spc) granted (law of 25 june 1990) |
Free format text: 92C0390, 780824 |
|
| CL | Concession to grant licences | ||
| TP | Transmission of property |