ES2019500A6 - New process for preparing anthracyclinones and their 5- imino derivatives - Google Patents
New process for preparing anthracyclinones and their 5- imino derivativesInfo
- Publication number
- ES2019500A6 ES2019500A6 ES8904002A ES8904002A ES2019500A6 ES 2019500 A6 ES2019500 A6 ES 2019500A6 ES 8904002 A ES8904002 A ES 8904002A ES 8904002 A ES8904002 A ES 8904002A ES 2019500 A6 ES2019500 A6 ES 2019500A6
- Authority
- ES
- Spain
- Prior art keywords
- give
- rbs3
- hydrolysis
- reaction
- anthracyclinones
- 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 - Lifetime
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
SE OBTIENEN ANTRACICLINONAS (I, X=0, RBS3=H) Y SUS 5-IMINODERIVADOS (I, X=NH, RBS3=H) DE FORMULA GENERAL SIGUIENTE FORMULA A PARTIR DE 1,4-DIHIDROXI-9,10-ANTRAQUINONAS (II) MEDIANTE REACCION CON AMONIACO PARA DAR LAS CORRESPONDIENTES ANTRAQUINONINAS (III), ACILACION CON UN HALOGENURO DE ACIDO (IV) PARA DAR EL DERIVADO N,0,0-TRIACILADO (V), ISOMERIZACION AL DERIVADO N,N,0-TRIACILADO (V), REACCION DE DIELS-ALDER CON UN DIENO (VII) PARA DAR EL ADUCTO (VIII), HIDROLISIS PARCIAL A (IX), ELIMINACION DE LOS GRUPOS ACILO PARA DAR (X), REACCION CON UN ORGANOMAGNESICO, AROMATIZACION E HIDROLISIS PARA DAR (XI), ADICION DE AGUA FORMANDO LA 5-IMINOANTRACICLINONA I (X=NH, RBS3=H) E HIDROLISIS CON UN ACIDO FUERTE A LA CORRESPONDIENTE ANTRACICLINONA (I, X=0, RBS3=H). LAS ANTRACICLINAS PRESENTAN ACTIVIDAD ANTITUMORAL.ANTHRACICLINONES (I, X = 0, RBS3 = H) AND THEIR 5-IMINODERIVES (I, X = NH, RBS3 = H) ARE OBTAINED FROM THE GENERAL FORMULA FOLLOWING FORMULA FROM 1,4-DIHIDROXI-9,10-ANTHRAQUINONES ( II) THROUGH REACTION WITH AMMONIA TO GIVE THE CORRESPONDING ANTRAQUINONINES (III), ACILATION WITH A HALOGENIDE OF ACID (IV) TO GIVE THE DERIVATIVE N, 0,0-TRIACILATE (V), ISOMERIZATION TO THE DERIVATIVE N, N, 0-TRIACILATED ( V), DIELS-ALDER REACTION WITH A DIENO (VII) TO GIVE THE ADDICT (VIII), PARTIAL HYDROLYSIS A (IX), ELIMINATION OF THE ACILUS GROUPS TO GIVE (X), REACTION WITH AN ORGANOMAGNESIC, AROMATIZATION AND HYDROLYSIS TO GIVE (XI), ADDITION OF WATER FORMING 5-IMINOANTRACICLINONE I (X = NH, RBS3 = H) AND HYDROLYSIS WITH A STRONG ACID TO THE CORRESPONDING ANTHRACICLINONE (I, X = 0, RBS3 = H). THE ANTHRACICLINES PRESENT ANTITUMORAL ACTIVITY.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES8904002A ES2019500A6 (en) | 1989-11-23 | 1989-11-23 | New process for preparing anthracyclinones and their 5- imino derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES8904002A ES2019500A6 (en) | 1989-11-23 | 1989-11-23 | New process for preparing anthracyclinones and their 5- imino derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2019500A6 true ES2019500A6 (en) | 1991-06-16 |
Family
ID=8265035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES8904002A Expired - Lifetime ES2019500A6 (en) | 1989-11-23 | 1989-11-23 | New process for preparing anthracyclinones and their 5- imino derivatives |
Country Status (1)
| Country | Link |
|---|---|
| ES (1) | ES2019500A6 (en) |
-
1989
- 1989-11-23 ES ES8904002A patent/ES2019500A6/en not_active Expired - Lifetime
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SA6 | Expiration date (snapshot 920101) |
Free format text: 2009-11-23 |
|
| FD1A | Patent lapsed |
Effective date: 20020617 |