GB1508388A - Derivatives of 9-hydroxy-ellipticine and a process for their preparation - Google Patents
Derivatives of 9-hydroxy-ellipticine and a process for their preparationInfo
- Publication number
- GB1508388A GB1508388A GB1660176A GB1660176A GB1508388A GB 1508388 A GB1508388 A GB 1508388A GB 1660176 A GB1660176 A GB 1660176A GB 1660176 A GB1660176 A GB 1660176A GB 1508388 A GB1508388 A GB 1508388A
- Authority
- GB
- United Kingdom
- Prior art keywords
- absent
- aralkyl
- aryl
- alkyl
- hydroxy
- 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
- QZTWUDDGLIDXSE-UHFFFAOYSA-N 9-hydroxyellipticine Chemical class N1=CC=C2C(C)=C(NC=3C4=CC(O)=CC=3)C4=C(C)C2=C1 QZTWUDDGLIDXSE-UHFFFAOYSA-N 0.000 title abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 230000017858 demethylation Effects 0.000 abstract 1
- 238000010520 demethylation reaction Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 208000032839 leukemia Diseases 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 238000005956 quaternization reaction Methods 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
1508388 9-Hydroxy-5,11-dimethyl-(6H)- pyrido[4,3-b]carbazole derivatives AGENCE NATIONALE DE VALORISATION DE LA RECHERCHE 23 April 1976 [25 April 1975] 16601/76 Divided out of 1436080 Heading C2C Novel compounds of the formula I wherein R is alkyl, aryl, aralkyl or is absent, and in this last case the nitrogen atom in the 2- position is not quaternized, R 1 is H, alkyl, aryl or aralkyl, R 2 is H or acyl and X is halogen or acyloxy or is absent, with the proviso that R and X cannot be absent when R 2 is hydrogen, may be prepared by subjecting 9-hydroxy ellipticine (I R 2 =H, R 1 =H, R 8 X absent) to at least one of the following steps: (a) acylation of the 9-OH group (b) substitution of the 6- nitrogen with alkyl, aryl or aralkyl in the presence of a strong base, if necessary with temporary projection of the 9-OH group, and (c) quaternization of the 2-nitrogen, if necessary with temporary protection of the 9-OH group. 9 - Hydroxyellipticine is prepared by demethylation of the 9-methoxy compound. Pharmaceutical compositions of compounds I with the usual excipients may be administered orally or parenterally in the treatment of leukaemia.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7513145A FR2308365A2 (en) | 1975-04-25 | 1975-04-25 | DERIVATIVES OF HYDROXY-9 ELLIPTICIN AND THEIR THERAPEUTIC APPLICATION |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1508388A true GB1508388A (en) | 1978-04-26 |
Family
ID=9154526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1660176A Expired GB1508388A (en) | 1975-04-25 | 1976-04-23 | Derivatives of 9-hydroxy-ellipticine and a process for their preparation |
Country Status (4)
| Country | Link |
|---|---|
| CH (2) | CH611621A5 (en) |
| DE (1) | DE2618223A1 (en) |
| FR (1) | FR2308365A2 (en) |
| GB (1) | GB1508388A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5565569A (en) * | 1993-01-25 | 1996-10-15 | Tanabe Seiyaku Co., Ltd. | Ellipticine derivative and process for preparing the same |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4310667A (en) * | 1976-04-22 | 1982-01-12 | Agence Nationale De Valorisation De La Recherche (Anvar) | 2-N Quaternary ammonium salt derivatives of 9-hydroxy ellipticine |
| FR2485015A1 (en) * | 1980-06-18 | 1981-12-24 | Anvar | OLIVACIN DERIVATIVES AND THEIR THERAPEUTIC APPLICATION |
| FR2527209A1 (en) * | 1982-05-24 | 1983-11-25 | Sanofi Sa | PROCESS FOR THE PREPARATION OF ELLIPTICIN DERIVATIVES, NOVEL COMPOUNDS THUS OBTAINED, AND THEIR ANTI-TUMOR ACTIVITY |
| FR2582649A1 (en) * | 1985-05-29 | 1986-12-05 | Centre Nat Rech Scient | METHYL BIS 7H PYRIDOCARBAZOLES METHYL DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME |
-
1975
- 1975-04-25 FR FR7513145A patent/FR2308365A2/en active Granted
-
1976
- 1976-04-23 GB GB1660176A patent/GB1508388A/en not_active Expired
- 1976-04-23 CH CH516576A patent/CH611621A5/en not_active IP Right Cessation
- 1976-04-26 DE DE19762618223 patent/DE2618223A1/en active Granted
-
1978
- 1978-07-27 CH CH810078A patent/CH616937A5/en not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5565569A (en) * | 1993-01-25 | 1996-10-15 | Tanabe Seiyaku Co., Ltd. | Ellipticine derivative and process for preparing the same |
| US5605904A (en) * | 1993-01-29 | 1997-02-25 | Tanabe Seiyaku Co., Ltd. | Ellipticine derivative and process for preparing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2308365A2 (en) | 1976-11-19 |
| CH616937A5 (en) | 1980-04-30 |
| DE2618223A1 (en) | 1976-11-11 |
| CH611621A5 (en) | 1979-06-15 |
| DE2618223C2 (en) | 1989-08-17 |
| FR2308365B2 (en) | 1978-08-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19941028 |