4-aryl quinols and analogs thereof as therapeutic agents

Details 4-aryl quinols and analogs thereof as therapeutic agents 4-aryl quinols and analogs thereof as therapeutic agents

C - Chemistry, Metallurgy

07

D

C07D 277/64 (2006.01) A61K 31/33 (2006.01) A61P 35/00 (2006.01) C07C 35/08 (2006.01) C07C 45/30 (2006.01) C07C 45/51 (2006.01) C07C 49/747 (2006.01) C07C 49/753 (2006.01) C07C 323/22 (2006.01) C07C 323/59 (2006.01) C07D 209/12 (2006.01) C07D 215/14 (2006.01) C07D 235/12 (2006.01) C07D 263/56 (2006.01) C07D 307/80 (2006.01) C07D 333/54 (2006.01)

Patent

CA 2452592

The present invention pertains to compounds of the formula (1), which are, inter alia, antiproliferative agents, anticancer agents, antimycobacterial agents, antituberculosis agents, and/or thioredoxin/thioredoxin reductase inhibitors: wherein: Q is =O or =N-S(=O)2-RQ;RQ is -H or optionally substituted C1-7alkyl, C3-20heterocyclyl, or C5-20aryl; Ar is optionally substituted C5-20aryl; Ro is an oxy substituent; the bond marked .alpha. is a single bond or a double bond; the bond marked .szlig. is a single bond or a double bond; R3 and R5 are each independently ring substituents; R2 and R6 are each independently ring substituents; and pharmaceutically acceptable salts, esters, amides, solvates, hydrates, and protected forms thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, for example, in the treatment of proliferative conditions, (e.g., cancer), mycobacterial infections (e.g., tuberculosis), and/or conditions mediated by thioredoxin/thioredoxin reductase.

L'invention se rapporte à des composés représentés par la formule (1), ces composés étant, entre autres, des agents antiprolifératifs, des agents anticancers, des agents antimycobactériens, des agents antituberculeux, et/ou des inhibiteurs de réductase thiorédoxine/thiorédixine. Dans la formule (I), Q est =O ou =N-S(=O)¿2?-R?Q ¿; R?Q¿ est H ou facultativement C¿1-7?alkyl substitué, C¿3-20?hétérocyclyl, ou C¿5-20?aryl ; R?0¿ est un substituant d'oxy ; la liaison marquée .alpha. est une liaison simple ou une liaison double, R?3¿ et R?5¿ sont chacun indépendamment des substituants de noyau. L'invention concerne aussi des sels, des esters, des amides, des solvants, des hydrates et des formes protégées de ces éléments. L'invention se rapporte aussi à des compositions pharmaceutiques contenant ces composés, et à l'utilisation de ces composés et de ces compositions, à la fois in vitro et in vivo, par exemple dans le traitement d'états prolifératifs (comme le cancer), des infections mycobactériennes (comme la tuberculose), et/ou des états médiés par la réductase thiorédixine/thiorédixine.

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