Anthranilic acid analogs

Details Anthranilic acid analogs Anthranilic acid analogs

C - Chemistry, Metallurgy

07

C

C07C 233/63 (2006.01) A61K 31/16 (2006.01) A61K 31/42 (2006.01) C07D 261/18 (2006.01) C07D 263/34 (2006.01)

Patent

CA 2297409

Compounds of formula (I) wherein: R1, R2 and R3 are, independently, hydrogen, nitro, cyano, C1-10 haloalkoxy, amino, C1-10 alkylamino, sulfo, sulfamoyl, C1- 10 alkylsulfonamido, C2-10 alkylcarboxamido C2-10 alkanoyl, C1-10 alkylsulfonyl, C1-10 haloalkylsulfonyl, C1-10 carboxyl, C1-10 haloalkyl and C6- 12 aryl; with the provisos: (1) that R1, R2 and R3 may not all simultaneously be hydrogen, and (2) when R1 and R2 are hydrogen, R3 may not be meta-CF3; R4, R5 and R6 are, independently , hydrogen, halogen, nitro, cyano, C1-10 carboalkoxy, C1-10 haloalkoxy, amino C1-10 alkylamino, sulfo, sulfamoyl, C1-10 alkylsulfonamido, C2-10 alkylcarboxamido C2-10 alkanoyl, C1-10 alkylsulfonyl, C1-10 haloalkylsulfonyl, C1-10 carboxyl, C1-10 haloalkyl, C1-10 alkyl and C6- 12 aryl; R7 is hydrogen , metal cation, acetylamido, alkoxyacetoyl or a related moiety which delivers the carboxylate in vivo; and X, Y and Z may form a C3-13 carbocyclic ring, oxazole, isoxazole, thiazole, isothiazole, furan, thiophene, 2H-pyrrole, pyrrole, 2-pyrroline, 3-pyrroline, imidazole, pyrazole, 1,2,3-oxadiazole or 1,2,3-triazole bound to the carbon skeleton; or pharmaceutically acceptable salts thereof useful in the treatment of disorders associated with smooth muscle contraction via potassium channel and chloride channel modulation.

Composés de formule (I), dans laquelle R¿1?, R¿2? et R¿3? représentent indépendamment, hydrogène, nitro, cyano, haloalcoxy C¿1-10?, amino, alkylamino C¿1-10?, sulfo, sulfamoyle, alkylsulfonamido C¿1-10?, alkylcarboxamido C¿2-10? alcanoyle C¿2-10?, alkylsulfonyle C¿1-10?, haloalkylsulfonyle C¿1-10?, carboxyle C¿1-10?, haloalkyle C¿1-10? et aryle C¿6-12?; à condition: (1) que R¿1?, R¿2? et R¿3? ne peuvent pas être simultanément hydrogène, et (2) lorsque R¿1? et R¿2? représentent hydrogène, R¿3? ne peut pas être méta-CF¿3?; R¿4?, R¿5? et R¿6? représentent séparément hydrogène, halogène, nitro, cyano, carboalcoxy C¿1-10?, haloalcoxy C¿1-10?, amino C¿1-10? alkylamino, sulfo, sulfamoyle, alkylsulfonamido C¿1-10?, alkylcarboxamido C¿2-10? alcanoyle, alkylsulfonyle C¿1-10?, haloalkylsulfonyle C¿1-10?, carboxyle C¿1-10?, haloalkyle C¿1-10?, alkyle C¿1-10? et aryle C¿6-12?; R¿7? représente hydrogène, cation métal, acétylamido, alcoxyacétoyle, ou une partie associée qui dégage le carboxylate in vivo; et X, Y et Z peuvent former un cycle carboxylique, oxazole, isoxazole, thiazole, isothiazole, furane, thiophène, 2H-pyrrole, pyrrole, 2-pyrroline, 3-pyrroline, imidazole, pyrazole, 1,2,3-oxadiazole ou 1,2,3-triazole lié au squelette carboné; ou des sels pharmaceutiquement acceptables de ceux-ci, utiles dans le traitement de troubles associés à une contraction d'un muscle lisse, par modulation du canal potassium et le canal chlorure.

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