Azaoxindole derivatives

Details Azaoxindole derivatives Azaoxindole derivatives

C - Chemistry, Metallurgy

07

D

167/231, 260/273

C07D 471/04 (2006.01) A61K 31/435 (2006.01)

Patent

CA 2033531

This invention relates to novel 4-, 5-, 6-, and 7- azaoxindole derivatives of the formula: (see fig. I) (wherein one of A, B, D and E is N and the others are CH; Y is H, OR3, OH, lower alkyl, CF3, COR3, halogen, COOR3, CONR3R3, CN, NO2, SR3, SOR3, SO2R3 or SO2NR3R3; R1 is lower alkyl or CONHR4; R2 is lower alkyl, (CH2)nR5 [where n is 0 or 1] or NHR6; R3 is H, lower alkyl, allyl, optionally substituted phenyl or optionally substituted benzyl; R4 is H, lower alkyl, hydroxyalkyl, cycloalkyl, COR3, optionally substituted phenyl or optionally substituted heteroaryl; R5 is H, cycloalkyl, optionally substituted phenyl or optionally substituted heteroaryl; R6 is phenyl, thiophene or furan, each optionally substituted; W is H, alkanoyl, cycloalkylcarbonyl, phenoxycarbonyl, acyloxyalkyl, alkoxycarbonyloxyalkyll alkylsulfonyl, lower alkyl, methylphenylsulfonyl or dialkylphosphonate, with the proviso that (a) when E is N, then at least one of X and Y is other than H; and (b) when either R2 is NHR or R1 is lower alkyl, then W is H). The compounds are anti-inflammatory and analgesic agents and inhibitors of one or more of prostaglandin H2 synthase, 5-lipoxygenase and interleukin-1 biosynthesis. They are useful in the treatment of chronic inflammatory diseases, allergy, psoriasis, various bone diseases, and immune dysfunctions such as systemic lupus erythematosis.

L'invention porte sur de nouveaux dérivés de 4-, 5-, 6-, et 7- azaoxindole de formule (voir fig. I) (où l'un de A, B, D ou E est N, les autres étant CH; Y est H, OR3, OH, un alkyle inférieur, CF3, COR3, un halogène, COOR3, CONR3R3, CN, NO2, SR3, SOR3, SO2R3 ou SO2NR3R3; R1 est un alkyle inf. ou CONHR4; R2 est un alkyle inf., (CH2)nR5¢n étant 0 ou 1! ou NHR6; R3 est H, un groupe alkyle inf., allyle, phényle avec substitution facultative ou benzyle avec substitution facultative; R4 est H, un groupe alkyle inf., hydroxyalkyle, cycloalkyle, COR3, phényle avec substitution facultative ou hétéroaryle avec substitution facultative; R5 est H, un groupe cycloalkyle, phényle avec substitution facultative ou hétéroaryle avec substitution facultative; R6 est un groupe phényle, thiényle ou furyle, chacun avec substitution facultative; W est H, un groupe alcanoyle, cycloalkylcarbonyle, phénoxycarbonyle, acyloxyalkyle, alcoxycarbonyl-oxyalkyle, alkylsulfonyle, alkyle inf., méthylphénylsulfonyle ou dialkylphosphonate, à la condition que : a) lorsque E est N, alors au moins l'un de X ou de Y est autre que H; b) lorsque R2 est NHR ou R1 un alkyle inf., alors W est H). Ces composés sont des anti-inflammatoires et des analgésiques, ainsi que des inhibiteurs de la biosynthèse de l'un ou de plusieurs des composés suivants : prostaglandine H2 synthase, 5-lipoxygénase et interleukine-1. Ils sont utiles pour le traitement des maladies inflammatoires chroniques, des allergies, du psoriasis, de diverses maladies des os, et de dysfonctions du système immunitaire, comme le lupus érythémateux disséminé.

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