GB1037379A - Desacetyl polynuclear indoles - Google Patents
Desacetyl polynuclear indolesInfo
- Publication number
- GB1037379A GB1037379A GB121365A GB121365A GB1037379A GB 1037379 A GB1037379 A GB 1037379A GB 121365 A GB121365 A GB 121365A GB 121365 A GB121365 A GB 121365A GB 1037379 A GB1037379 A GB 1037379A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- vincaleukoblastine
- desacetyl
- piperazino
- cycloalkyl
- 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
- 150000002475 indoles Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 150000001875 compounds Chemical class 0.000 abstract 4
- -1 naphthalene aldehyde Chemical class 0.000 abstract 4
- 229960003048 vinblastine Drugs 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 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 abstract 2
- PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 abstract 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 229940089960 chloroacetate Drugs 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 208000032839 leukemia Diseases 0.000 abstract 1
- 230000036210 malignancy Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The title compounds are prepared by heating a mixture of 2-methylbenz- or -naphthoxazole, benzene or naphthalene aldehyde, a sulphonic acid, an N,N-di(C1- 6 alkyl) alkanoyl amide and an inert solvent, removing water of condensation and recovering the product. References has been directed by the Comptroller to Specification 967,483.ALSO:The invention comprises compounds of the formula <FORM:1037379/C2/1> and non-toxic salts thereof, wherein R is hydrogen, C1- 5 alkyl, C3- 8 cycloalkyl or a carbocyclic or heterocyclic aromatic radical containing one ring or two condensed rings, optionally bearing substituents, R1 is hydrogen, C1- 5 alkyl or C3- 8 cycloalkyl and R11 is C1- 5 alkyl, or R1 and R11 together with the nitrogen atom form a pyrrolidino, piperidino, piperazino, morpholino, 4-(C1- 5 alkyl) - piperazino, 4 - (hydroxy - substituted C1- 5 alkyl)-piperazino or 4-(monocyclicaryl) -piperazino group and R111 is HCO-, C- 5 alkyl or C1- 5 alkyl-CO-, e.g. N,N-dimethyl-, N - methyl - N - cyclopropyl and N - methyl -, desacetyl vincaleukoblastine glycinate; and their preparation by reacting a corresponding 4-a -chloroacyl compound with an amine HNR1R11. Desacetyl - vincaleukoblastine 4 - chloroacetate used as a starting material is made by reacting vincaleukoblastine with methanolic HCl and treating the resulting desacetyl-vincaleukoblastine with chloracetic anhydride. Pharmaceutical preparations for alleviating the effect of malignancies, e.g. leukemia, comprise the above compounds of the invention and an inert carrier.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB121365A GB1037379A (en) | 1965-01-11 | 1965-01-11 | Desacetyl polynuclear indoles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB121365A GB1037379A (en) | 1965-01-11 | 1965-01-11 | Desacetyl polynuclear indoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1037379A true GB1037379A (en) | 1966-07-27 |
Family
ID=9718105
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB121365A Expired GB1037379A (en) | 1965-01-11 | 1965-01-11 | Desacetyl polynuclear indoles |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1037379A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0124502A3 (en) * | 1983-04-29 | 1986-05-07 | Omnichem Societe Anonyme | Conjugates of vinblastine and its derivatives, process for their preparation and pharmaceutical compositions containing these conjugates |
-
1965
- 1965-01-11 GB GB121365A patent/GB1037379A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0124502A3 (en) * | 1983-04-29 | 1986-05-07 | Omnichem Societe Anonyme | Conjugates of vinblastine and its derivatives, process for their preparation and pharmaceutical compositions containing these conjugates |
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