Fused heteroaromatic glucokinase activators

C - Chemistry – Metallurgy – 07 – D

Patent

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Details

C07D 263/58 (2006.01) A61K 31/4184 (2006.01) A61K 31/423 (2006.01) A61K 31/428 (2006.01) A61K 31/47 (2006.01) A61P 3/10 (2006.01) C07D 215/38 (2006.01) C07D 235/30 (2006.01) C07D 277/82 (2006.01)

Patent

CA 2429642

Glucokinase activating compounds or pharmaceutically acceptable salts of Formula I-0: (See formula I-0) wherein M is (See formula I) or (See formula II) Q is (See formula III) or (See formula IV) R1 is an alkyl having from 1 to 3 carbon atoms; R2 is hydrogen, halo, nitro, cyano, or perfluoro-methyl; R3 is a cycloalkyl having from 4 to 7 carbon atoms or 2- propyl; R5 is halogen; R6 is halogen; W is O, S or NH; each Y is independently CH or N; Z is CH2-CH2-CH2-CH2 or CH=CR4-CH=CH-, wherein R4 is hydrogen, halo, or an alkyl sulfone having from 1 to 3 carbon atoms; and dotted lines collectively represent O or 2 additional double bonds in the heterocyclic ring structure. Compounds of Formula 1-0 may be present either as a racemate or in the isolated "R" configuration at the asymmetric carbon shown.

La présente invention concerne des composés activateurs de la glucokinase ou des sels pharmaceutiquement acceptables de la formule I-0, dans laquelle M correspond à la formule II ou à la formule III; Q à la formule IV ou à la formula V; R<1> est un alkyle renfermant de 1 à 3 atomes de carbone; R<2> est un hydrogène, halo, nitro, cyano ou perfluoro-méthyle; R<3> est un cycloalkyle renfermant de 4 à 7 atomes de carbone ou un 2-propyle; R<5> est un halogène; R<6> est un halogène; W est O, S ou NH; chaque Y est indépendamment CH ou N; Z est CH2-CH2-CH2-CH2 ou CH=CR<4>-CH=CH-, où R<4> est un hydrogène, un halo, ou an alkyl sulfone renfermant de 1 à 3 atomes de carbone; et les lignes pointillées représentent collectivement O ou 2 doubles liaisons supplémentaires dans la structure du noyau hétérocyclique. Les composés de la formule I-0 peuvent être présents soit dans le racémate soit dans la configuration </= R >/= isolée du carbone asymétrique illustré.

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