Compounds for the treatment of metabolic disorders

C - Chemistry – Metallurgy – 07 – D

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C07D 319/08 (2006.01) A61K 31/192 (2006.01) A61K 31/34 (2006.01) A61K 31/357 (2006.01) A61K 31/36 (2006.01) C07C 59/13 (2006.01) C07D 317/30 (2006.01)

Patent

CA 2651598

Agents useful for the treatment of various metabolic disorders, such as insulin resistance syndrome, diabetes, polycystic ovary syndrome, hyperlipidemia, fatty liver disease, cachexia, obesity, atherosclerosis and arteriosclerosis are disclosed, compound of the formula (I): wherein n is 1 or 2; m is 0, 1, 2, 3, 4, 5, 6, 7 or 8; q is 0 or 1; t is 0 or 1; R1 is alkyl having from 1 to 3 carbon atoms; R2 is hydrogen, halo, alkyl having from 1 to 3 carbon atoms, or alkoxy having from 1 to 3 carbon atoms; R3 and R4 together are alkyl having two or three carbon atoms; or R3 and R4 are the same as each other and each is methyl or ethyl; R 5 is hydrogen or alkyl having from one to six carbon atoms. A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from: halo, hydroxy, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy; or A is cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl; or A is a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound of formula (I) by a ring carbon. Alternatively, the agent can be a pharmaceutically acceptable salt of the compound of Formula (I).

La présente invention concerne des agents utiles dans le traitement de divers troubles métaboliques, tels que le syndrome d'insulinorésistance, le diabète, le syndrome des ovaires polykystiques, l'hyperlipidémie, la stéatose hépatique, la cachexie, l'obésité, l'athérosclérose et l'artériosclérose, ainsi qu'un composé de formule (I) dans laquelle n est 1 ou 2; m est 0, 1, 2, 3, 4, 5, 6, 7 ou 8; q est 0 ou 1, t est 0 ou 1, R1 est alkyle ayant de 1 à 3 atomes de carbone, R2 est hydrogène, halo, alkyle ayant de 1 à 3 atomes de carbone ou alcoxy ayant de 1 à 3 atomes de carbone, R3 et R4 ensemble sont alkyle ayant deux ou trois atomes de carbone, ou bien R3 et R4 sont identiques l'un à l'autre et chacun est méthyle ou éthyle et R 5 est hydrogène ou alkyle ayant de un à six atomes de carbone. A est phényle, non substitué ou substitué par 1 ou 2 groupes sélectionnés parmi halo, hydroxy, alkyle ayant 1 ou 2 atomes de carbone, perfluorométhyle, alcoxy ayant 1 ou 2 atomes de carbone et perfluorométhoxy; ou bien A est cycloalkyle ayant de 3 à 6 atomes de carbone cyclique, le cycloalkyle étant non substitué ou un ou deux carbones cycliques étant indépendamment monosubstitués par méthyle ou éthyle; ou bien A est un noyau hétéroaromatique à 5 ou 6 éléments ayant 1 ou 2 hétéroatomes cycliques sélectionnés parmi N, S et O et le noyau hétéroaromatique est lié de manière covalente au reste du composé de formule (I) par un carbone cyclique. Dans une variante, l'agent peut être un sel pharmaceutiquement acceptable du composé de formule (I).

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