Anthranilic acid analogs

Details Anthranilic acid analogs Anthranilic acid analogs

C - Chemistry, Metallurgy

07

C

C07C 233/55 (2006.01) C07D 213/79 (2006.01) C07D 213/80 (2006.01)

Patent

CA 2297412

Compounds of formula (I) wherein: R1, R2, R3, R4, R5, R6, R7 and R8 are, independently, hydrogen, COOR15, halogen, nitro, cyano, C1-10 alkoxy, C1-10 haloalkoxy, sulfonic acid, C1-10 alkylsulfonyl, C6-12 arylsulfonyl, C6-12 aralkylsulfonyl, C1-10 alkylsulfinyl, C6-12 arylsufinyl, C6-12 aralkylsulfinyl, sulfamoyl, C1-10 alkylsulfamido, C6-12 arylsulfamido, C1-10 alkanoyl, C6-12 aryloyl, C6-12 aralkanoyl, amino, C1-10 alkylamino, C2-10 dialkylamino, C6-12 arakylamino, C6-12 arylamino, carboxamido, C1-10 alkylcarboxamido, C6-12 arylcarboxamido, C1-10 haloalkyl, C1-10 alkyl, C2-12 alkenyl, C6-12 aryl, C6-12 aralkyl; with the proviso that at least one of R4 and R5 is COOR15; R9 is hydrogen, C1-10 alkyl, and C1-10 haloalkyl; R10 is hydrogen, C1-10 alkyl, C1-10 haloalkyl, or C2-12 alkylidene; R15 is hydrogen, metal cation, acetylamido, alkoxyacetoyl or a related moiety which delivers the carboxylate in vivo; the dotted line is an optional double bond; with the proviso that when R10 is an alkylidene moiety, the double bond is absent; and W is nitrogen or carbon bearing a hydrogen, or R4, R5 or R6 as hereinbefore defined; or pharmaceutical salts thereof, are useful in the treatment of disorders associated with smooth muscle contraction via potassium channel and chloride channel modulation.

L'invention concerne des composés de formule (I) dans laquelle: R¿1?, R¿2?, R¿3?, R¿4?, R¿5?, R¿6?, R¿7? et R¿8? représentent indépendamment, hydrogène, COOR¿15?, halogène, nitro, cyano, alcoxy C¿1-10?, haloalcoxy C¿1-10?, acide sulfonique, alkylsulfonyle C¿1-10?, arylsulfonyle C¿6-12?, aralkylsulfonyle C¿6-12?, alkylsulfinyle C¿1-10?, arylsulfinyle C¿6-12?, aralkylsulfinyle C¿6-12?, sulfamoyle, alkylsulfamido C¿1-10?, arylsulfamido C¿6-12?, alcanoyle C¿1-10?, aryloyle C¿6-12?, aralcanoyle C¿6-12?, amino, alkylamino C¿1-10?, dialkylamino C¿2-10?, aralkylamino C¿6-12?, arylamino C¿6-12?, carboxamido, alkylcarboxamido C¿1-10?, arylcarboxamido C¿6-12?, haloalkyle C¿1-10?, alkyle C¿1-10?, alcényle C¿2-12?, aryle C¿6-12?, aralkyle C¿6-12?, à la condition que R¿4? et/ou R¿5? représentent COOR¿15?; R¿9? représente hydrogène, alkyle C¿1-10? et haloalkyle C¿1-10?; R¿10? représente hydrogène, alkyle C¿1-10?, haloalkyle C¿1-10? ou alkylidene C¿2-12?; R¿15? représente hydrogène, un cation métallique, acétylamido, alcoxyacétoyle ou une fraction apparentée administrant le carboxylate in vivo; la ligne pointillée représente une double liaison optionnelle à la condition que lorsque R¿10? représente une fraction alkylidène, la double liaison est absente; et W représente azote ou carbone portant un hydrogène, ou R¿4?, R¿5? ou R¿6? tel que ci-dessus défini; ou bien leurs sels pharmaceutiques, lesquels composés sont utiles dans le traitement de troubles associés à la contraction des muscles lisses par la modulation des canaux potassiques et des canaux à chlorure.

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