Acridone derivatives and method of preparation of 8-hydroxy...

Details Acridone derivatives and method of preparation of 8-hydroxy... Acridone derivatives and method of preparation of 8-hydroxy...

C - Chemistry, Metallurgy

07

D

C07D 471/06 (2006.01) C07D 219/08 (2006.01)

Patent

CA 2268157

A process of preparing a compound of formula (I), wherein R1 and R2 are alkyl groups of 1 to 4 carbon atoms and n is from 2 to 5, comprises reacting a 1-chloro-7-(protected hydroxy)-4-nitroacridin-9(10H)-one of formula (IV-P), wherein A is a hydroxy-protecting group removable by reduction, with an .omega.-(dialkyl-amino)alkylamine of formula: NH2-(CH2)n NR1R2, in which n, R1 and R2 are as defined above, to produce a 7-(protected hydroxy)-4-nitro-1-[[.omega.-(dialkylamino)alkyl]amino]acridin-9(10H)-one(III- P), reducing the compound (III-P) at a temperature of from 15 to 50°C with a hydrogen gas or with formate ions, in the presence of a palladium catalyst and formic acid, removing substantially all the residual palladium and heating the remaining reaction mixture to effect cyclisation to the corresponding compound of formula (I). If desired, after removal of the palladium the intermediate 7-hydroxy-4-N-formyl- 1-[[.omega.-(dialkylamino)alkyl]amino]acridin-9(10H)-one can be isolated and subsequently cyclised by heating. Such compounds have anti- neoplastic activity.

Procédé de préparation d'un composé de formule (I) dans lequel R<1> et R<2> représentent des groupes alkyle contenant de 1 à 4 atomes de carbone et n est compris entre 2 et 5. Dans ce procédé on fait réagir un 1-chloro-7-(hydroxy protégé)-4-nitroacridine-9(10H)-one de formule (IV-P), dans laquelle A représente un groupe protecteur-hydroxy éliminable par réduction, avec un omega -(dialkylamino)alkylamine de formule: NH2-(CH2)nNR<1>R<2> dans laquelle n, R<1> et R<2> sont tels que définis plus haut pour produire un 7-(hydroxy protégé)-4-nitro-1-[[ omega -(dialkylamino)alkyl]amino]acridine-9(10H)-one(III-P); on réduit le composé (III-P) à une température comprise entre 15 et 50 DEG C avec un gaz hydrogène ou avec des ions formate, en présence d'un catalyseur au palladium et d'acide formique; on élimine sensiblement tout le palladium résiduel et on chauffe le mélange réactionnel restant pour effectuer la cyclisation du composé correspondant de formule (I). En fonction des besoins, on peut, après l'élimination du palladium isoler puis cycliser par chauffage l'intermédiaire 7-hydroxy-4-N-formyle-1-[[ omega -(dialkylamino)alkyl]amino]acridine]-9(10H)-one. Ces composés possèdent une activité anti-néoplasique.

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