Tricyclic derivatives and their use as anti-cancer agents

Details Tricyclic derivatives and their use as anti-cancer agents Tricyclic derivatives and their use as anti-cancer agents

C - Chemistry, Metallurgy

07

D

C07D 487/04 (2006.01) A61K 31/38 (2006.01) A61K 31/395 (2006.01) A61K 31/40 (2006.01) A61K 31/675 (2006.01) A61K 31/695 (2006.01) A61K 31/70 (2006.01) C07D 495/04 (2006.01) C07F 7/10 (2006.01) C07F 9/6561 (2006.01) C07H 5/06 (2006.01) C07H 13/10 (2006.01)

Patent

CA 2211979

A compound of formula (I) or a salt or physiologically functional derivative thereof, wherein A is (a), (b), (c) (d), X is O, S, SO, SO2, CH2, CO or NR7, wherein R7 is H, alkyl, aralkyl, aryl, alkenyl, acyl, alkynyl, sulphonyl, substituted sulphonyl, or COOMe; Y is O, S, SO, SO2, CH2, CO or NR7; R1 is COR8, CHO, CH2OH, CH2OR9, CONH2, COOR8, CONHR8, CONR8R9, CSOR8, CSSR8, COSR8, CSNHR8, CSNR8R9, CNHOR8 wherein R8 and R9 are independently hydrogen, alkoxyalkyl, heterocycloalkyl, heteroaralkyl, or C1-10 optionally substituted hydrocarbyl group which may optionally contain one or two oxygen atoms in the chain; or R8 and R9 are a sugar group. R2 is H, halo, cyano, COOR8, alkyl, aryl, alkenyl, alkynyl, alkoxy, (wherein alkyl, aryl, alkenyl, alkynyl and alkoxy can be substituted) or CH2CH2CO2R12 wherein R12 is alkyl or aryl; R3 is H, alkyl, halogen, cyano, amino, COOR8, CONHR8, COR8, CH2OH, CH2OR8, CONH2, CONR8R9, CSOR8, CSSR8, COSR8, CSNHR8, CSNR8R9 or CNHOR8; R4 is H, halogen, cyano, amino, alkyl, COOR8, CONHR8, COR8, CH2OH, CH2OR8, CONH2, CONR8R9, CSOR8, CSSR8, COSR8, CSNHR8, CSNR8R9 or CNHOR8; R5 is H, hydroxy, aryloxy, aralkyloxy, alkyl, substituted alkyl, aralkyl, nitro, amino, halo, cyano COOR8 or CNHOR8; R5 is H, hydroxy, CHO or COR13 wherein R13 is alkyl or aryl; wherein R8 is not H when R2 is H and R3 is not H or Me when A is (c). Processes for their preparation are described, together with their use in medicine, particularly cancer therapy and pharmaceutical formulations comprising the compounds.

Un composé de formule (I) ou un sel ou un dérivé physiologiquement fonctionnel de ce dernier, où A est (a), (b), (c) (d), X est O, S, SO, SO2, CH2, CO ou NR7, où R7 est H, un groupe alkyle, aralkyle, aryle, alkényle, acyle, alkynyle, sulfonyle, sulfonyle substitué ou COOMe; Y est O, S, SO, SO2, CH2, CO ou NR7; R1 est COR8, CHO, CH2OH, CH2OR9, CONH2, COOR8, CONHR8, CONR8R9, CSOR8, CSSR8, COSR8, CSNHR8, CSNR8R9, CNHOR8 où R8 et R9 sont indépendamment un atome d'hydrogène, un groupe alcoxyalkyle, hétérocycloalkyle, hétéroaralkyle ou un groupe hydrocarbyle en C1-C10 facultativement substitué dont la chaîne peut facultativement contenir un ou deux atomes d'oxygène; ou R8 et R9 sont un groupe glucidique. R2 est H, un groupe halo, un cyano, COOR8, un alkyle, un aryle, un alkényle, un alkynyle, un alcoxy, (où les groupes alkyle, aryle, alkényle, alkynyle et alcoxy peuvent être substitués) ou CH2CH2CO2R12 où R12 est un alkyle ou un aryle; R3 est H, un alkyle, un halogène, un cyano, un amino, COOR8, CONHR8, COR8, CH2OH, CH2OR8, CONH2, CONR8R9, CSOR8, CSSR8, COSR8, CSNHR8, CSNR8R9 ou CNHOR8; R4 est H, un halogène, un cyano, un amino, un alkyle, COOR8, CONHR8, COR8, CH2OH, CH2OR8, CONH2, CONR8R9, CSOR8, CSSR8, COSR8, CSNHR8, CSNR8R9 ou CNHOR8; R5 est H, un hydroxy, un aryloxy, un aralkyloxy, un alkyle, un alkyle substitué, un aralkyle, un nitro, un amino, un halo, un cyano, COOR8 ou CNHOR8; R5 est H, un hydroxy, CHO ou COR13 où R13 est un alkyle ou un aryle; où R8 n'est pas H lorsque R2 est H et R3 n'est pas H ou Me lorsque A est (c). On décrit des procédés pour leur préparation, ainsi que leur utilisation en médecine, particulièrement dans le traitement du cancer, et des formulations pharmaceutiques comprenant ces composés.

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