Bis-indole derivatives having antimetastatic activity, a...

C - Chemistry – Metallurgy – 07 – D

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C07D 401/14 (2006.01) A61K 31/40 (2006.01) A61K 31/404 (2006.01) A61K 31/4439 (2006.01) C07D 209/10 (2006.01) C07D 209/14 (2006.01) C07D 403/14 (2006.01) C07D 405/14 (2006.01) C07D 409/14 (2006.01) C07F 9/38 (2006.01) C07F 9/572 (2006.01)

Patent

CA 2294250

The present invention relates to compounds of general formula (I) wherein: R and R' are independently selected from hydrogen, hydroxy, chlorine, bromine, iodine, fluorine, (C1-C6)alkyl, (C1-C4)alkoxy, (C1-C4)acyloxy, amino, mono-(C1- C4)alkylamino, di-(C1-C4)alkylamino, -SH, (C1-C4)alkylthio, carboxy, (C1- C4)alkoxycarbonyl groups; R1 and R1' are independently selected from hydrogen, hydroxy, hydroxymethyl, amino, carboxy, (C1-C4)alkyl groups; A is a phenyl or naphthyl group substituted by at least one group selected from hydroxy, carboxy, -SH, -CONHOH or -PO3H2 group, or is a 5- or 6-membered heterocycle containing one or two heteroatoms selected from oxygen, nitrogen or sulfur, which can be optionally benzocondensed and/or substituted by at least one group selected from pyridyl, -SH, -PO3H2, carboxy or CONHOH, or is a group of the formula -(CH2)n-X, in which n is zero or the integers 1 or 2, and X is selected from -SH, -PO3H2, -CONHOH, carboxy, amino, mono-(C1-C4)alkylamino, di- (C1-C4)alkylamino, enantiomers, diastereoisomers, racemates and mixtures thereof, as well as salts thereof with pharmaceutically acceptable acids and bases, as antitumor and antimetastatic agents.

La présente invention concerne des composés selon la formule générale (I). Dans cette dernière, R et R' sont indépendamment sélectionnés parmi des groupes hydrogène, hydroxy, chlore, brome, iode, fluor, alkyle (C¿1?-C¿6?), alcoxy (C¿1?-C¿4?), acyloxy (C¿1?-C¿4?), amino, mono-(C¿1?-C¿4?)alkylamino, di-(C¿1?-C¿4?)alkylamino, -SH, alkylthio(C¿1?-C¿4?), carboxy, alcoxycarbonyl(C¿1?-C¿4?). R¿1? et R¿1?' sont indépendamment sélectionnés parmi des groupes hydrogène, hydroxy, hydroxyméthyle, amino, carboxy, alkyl(C¿1?-C¿4?); A est un groupe phényle ou naphtyle substitué par au moins un groupe sélectionné parmi des groupes hydroxy, carboxy, -SH, -CONHOH ou -PO¿3?H¿2?, ou est un hétérocycle à 5 ou 6 éléments contenant un ou deux hétéroatomes sélectionnés parmi de l'oxygène, azote ou soufre, qui peuvent éventuellement être benzocondensés et/ou substitués par au moins un groupe sélectionné parmi pyridyl, -SH, -PO¿3?H¿2?, carboxy ou CONHOH ou est un groupe présentant la formule -(CH¿2?)n-X dans laquelle n est égal à zéro ou les nombres entiers 1 ou 2, et X est sélectionné parmi -SH, -PO¿3?H¿2?, -CONHOH, carboxy, amino, mono-(C¿1?-C¿4?)alkylamino, di-(C¿1?-C¿4?)alkylamino, énantiomères, diastéréoisomères, composés racémiques et mélanges de ces derniers, ainsi que des sels de ces derniers avec des acides pharmaceutiquement acceptables et des bases, comme agents antitumoraux et antimétastastiques.

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