4-, 5-, 6- and 7-indole derivatives useful for the treatment...

Details 4-, 5-, 6- and 7-indole derivatives useful for the treatment... 4-, 5-, 6- and 7-indole derivatives useful for the treatment...

C - Chemistry, Metallurgy

07

D

C07D 403/06 (2006.01) A61K 31/4439 (2006.01) A61K 31/454 (2006.01) A61K 31/496 (2006.01) A61P 25/16 (2006.01) A61P 25/18 (2006.01) A61P 25/28 (2006.01) C07D 401/06 (2006.01) C07D 403/14 (2006.01)

Patent

CA 2419266

The present invention relates to 4-, 5-, 6- or 7-methylene substituted indolyl derivatives of Formula 1, wherein R is aryl or heteroaryl, where said aryl or heteroaryl groups may be substituted one or more times with a substituent selected from hydrogen, halogen, cyano, nitro, C1-6-alkyl, C2-6-alkenyl, C2-6- alkynyl, C3-8cycloalkyl, C3-8-cycloalkyl-C1-6-alkyl, C1-6-alkoxyl, C1-6- alkylthio, hydroxy, hydroxy-C1-6-alkyl trifluoromethyl, trifluoromethylsulfonyl, C1-6-alkylsulfonyl, amino, C1-6-alkylamino, di-(C1-6- alkyl) amino, acyl, aminocarbonyl and a methylene dioxy group; X is N, C or CH; provided that the dotted line indicates a bond when X is C and no bond when X is N or CH; R1 is hydrogen, C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3- 8-cycloalkyl, C3-8-cycloalkyl-C1-6-alkyl, aryl, aryl-C1-6-alkyl, acyl, thioacyl, C1-6-alkylsulfonyl, trifluoromethylsulfonyl or arylsulfonyl; and R2 and R3 are independently selected from hydrogen, halogen, cyano, nitro, C1-6- alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-8-cycloalkyl, C3-8-cycloalkyl-C1-6- alkyl, C1-6-alkoxy, C1-6-alkylthio, hydroxy, hydroxy-C1-6-alkyl trifluoromethyl, trifluoromethylsulfonyl, C1-6-alkylsulfonyl, amino, C1-6- alkylamino, di-(C1-6-alkyl)amino, acyl and aminocarbonyl; The compounds of the invention are selective dopamine D4 ligands.

La présente invention concerne des dérivés d'indolyle à substitution méthylène en 4, 5, 6 ou 7 représentés par la formule (I), dans laquelle R est aryle ou hétéroaryle, ces groupes aryle ou hétéroaryle pouvant être substitués une ou plusieurs fois par un substituant choisi parmi hydrogène, halogène, cyano, nitro, alkyle C¿1-6?, alcényle C¿2-6?, alkylnyle C¿2-6?, cycloalkyle C¿3-8?, cycloalkyle C¿3-8?-alkyle C¿1-6?, alcoxy C¿1-6?, alkylthio C¿1-6?, hydroxy, hydroxy-alkyle C¿1-6?, trifluorométhyle, trifluorométhylsulfonyle, alkylsulfonyle C¿1-6?, amino, alkylamino C¿1-6?, di-(alkyle C¿1-6?)amino, acyle, aminocarbonyle et un groupe méthylènedioxy; X est N, C ou CH, à condition que la ligne pointillée indique une liaison lorsque X est C et aucune liaison lorsque X est N ou CH; R?1¿ est hydrogène, alkyle C¿1-6?, alcényle C¿2-6?, alkynyle C¿2-6?, cycloalkyle C¿3-8?, cycloalkyle C¿3-8?-alkyle C¿1-6?, aryle, aryle-alkyle C¿1-6?, acyle, thioacyle, alkylsulfonyle C¿1-6?, trifluorométhylsulfonyle ou arylsulfonyle; et R?2¿ et R?3¿ sont indépendamment choisis parmi hydrogène, halogène, cyano, nitro, alkyle C¿1-6?, alcényle C¿2-6?, alkynyle C¿2-6?, cycloalkyle C¿3-8?, cycloalkyle C¿3-8?-alkyle C¿1-6?, alcoxy C¿1-6?, alkylthio C¿1-6?, hydroxy, hydroxy-alkyle C¿1-6?, trifluorométhyle, trifluorométhylsulfonyle, alkylsulfonyle C¿1-6?, amino, alkylamino C¿1-6?, di-(alkyle C¿1-6?)amino, acyle et aminocarbonyle. Les composés de l'invention sont des ligands sélectifs de la dopamine D¿4?.

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