Quinoline carboxamides as tnf inhibitors and as pde-iv...

Details Quinoline carboxamides as tnf inhibitors and as pde-iv... Quinoline carboxamides as tnf inhibitors and as pde-iv...

C - Chemistry, Metallurgy

07

D

C07D 215/48 (2006.01) A61K 31/47 (2006.01) A61K 31/505 (2006.01) A61K 31/535 (2006.01) A61K 45/06 (2006.01) C07D 401/12 (2006.01) C07D 401/14 (2006.01) C07D 417/12 (2006.01)

Patent

CA 2252531

A compound of general formula (i), wherein X is CO or CS; R is H, halogen or alkyl; R1 represents OH, alkoxy optionally substituted with one or more halogens, or thioalkyl; R2, R3 and R4 are the same or different and are each H, R7, OR11, COR7, C(=NOR7)R7, alkyl-C(=NOR7)R7, halogen CF3, alkyl-C(=NOH)R7, C(=NOH)R7, CN, CO2H, CO2R11, CONH2, CONHR7, CON(R7)2, NR9R10 or CONR12R13 where NR12R13 is a heterocyclic ring optionally substituted with one or more R15; R5 represents H, arylalkyl, heteroarylalkyl, heterocycloalkyl, S(O)mR11 or alkyl optionally substituted with one or more substituents chosen from hydroxy, alkoxy, CO2R8, SO2NR12R13, CONR12R13, CN, carbonyl oxygen, NR9R10, COR11 and S(O)nR11; R6 represents aryl, heteroaryl, heterocyclo, arylalkyl, heteroarylalkyl or heterocycloalkyl; in R5 and/or R6, the aryl/heteroaryl/heterocyclo portion is optionally substituted with one or more substituents alkyl-R14 or R14. The compounds can be used to treat disease states, for example disease states associated with proteins that mediate cellular activity, for example by inhibiting tumour necrosis factor and/or by inhibiting phosphodiesterase IV.

Composé de formule générale (i) dans laquelle X est CO ou CS; R est H, halogène ou alkyle; R¿1? représente OH, alcoxy éventuellement substitué par un ou plusieurs halogènes, ou thioalkyle; R¿2?, R¿3? et R¿4? sont identiques ou différents et sont chacun H, R¿7?, OR¿11?, COR¿7?, C(=NOR¿7?)R¿7?, alkyl-C(=NOR¿7?)R¿7?, halogène, CF¿3?, alkyl-C(=NOH)R¿7?, C(=NOH)R¿7?, CN, CO¿2?H, CO¿2?R¿11?, CONH¿2?, CONHR¿7?, CON(R¿7?)¿2?, NR¿9?R¿10? ou CONR¿12?R¿13? dans laquelle NR¿12?R¿13? est un noyau hétérocyclique éventuellement substitué par un ou plusieurs R¿15?; R¿5? est H, arylalkyle, hétéroarylalkyle, hétérocycloalkyle, S(O)¿m?R¿11? ou alkyle éventuellement substitué par un ou plusieurs substituants choisi parmi hydroxy, alcoxy, CO¿2?R¿8?, SO¿2?NR¿12?R¿13?, CON¿12?R¿13?, CN, oxygène carbonyle, NR¿9?R¿10?, COR¿11? et S(O)¿n?R¿11?; R¿6? est aryle, hétéroaryle, hétérocyclo, arylalkyle, hétéroarylalkyle ou hétérocycloalkyle; dans R¿5? et/ou R¿6?, la partie aryle/hétéroaryle/hétérocyclo est éventuellement substituée par un ou plusieurs substituants alkyl-R¿14? ou R¿14?. Lesdits composés peuvent être utilisés pour traiter des maladies, telles des états pathologiques associés aux protéines qui induisent l'activité cellulaire, par exemple en inhibant le facteur de nécrose tumorale (TNF) et/ou en inhibant la photodiestérase-IV.

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