Derivatives of pyrimido¬6,1-a|isoquinolin-4-one

Details Derivatives of pyrimido¬6,1-a|isoquinolin-4-one Derivatives of pyrimido¬6,1-a|isoquinolin-4-one

C - Chemistry, Metallurgy

07

D

C07D 471/04 (2006.01) A61K 31/519 (2006.01) A61K 31/553 (2006.01) A61P 11/00 (2006.01) C07D 221/00 (2006.01) C07D 239/00 (2006.01) C07D 267/00 (2006.01) C07D 498/04 (2006.01)

Patent

CA 2368460

Compounds of general formula (I) wherein each of R1 and R2 independently represents a C1-6 alkyl or C2-7 acyl group; X represents OCH2 or a group CR3R4, wherein each of R3 or R4 independently represents a hydrogen atom or a C1-3 alkyl group; R5 represents a hydrogen atom or a C1-3 alkyl, C2-3 alkenyl or C2-3 alkynyl group; R6 represents a hydrogen atom or a C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, amino, C1-6 alkylamino, di(C1-6) alkylamino or C2-7 acylamino group; each of R7 and R8 independently represents a hydrogen or halogen atom or a hydroxy, trifluoromethyl, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C2-7 acyl, C1-6 alkylthio, C1-6 alkoxy, C3-6 cycloalkyl; R9 represents a hydrogen or halogen atom or a hydroxy, trifluoromethyl, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C2-7 acyl, C1-6 alkylthio, C1-6 alkoxy or C3-6 cycloalkyl group, or salts thereof are useful for treatment of respiratory disorders such as asthma. Compounds of the invention have a longer duration of action than the known compound trequinsin (9,10-dimethoxy-3-methyl- 2-mesitylimino-2,3,6,7-tetrahydro-4H-pyrimido[6,1-a]isoquinolin-4-one) and do not have trequinsin's very bitter taste.

L'invention concerne les composés de formule générale (I) dans laquelle R?1¿ et R?2¿ représentent, indépendamment, un groupe C¿1-6? alkyle ou C¿2-7? acyle; X représente OCH¿2? ou un groupe CR?3¿R?4¿, dans lequel R?3¿ et R?4¿ représentent, indépendamment, un atome d'hydrogène ou un groupe C¿1-3? alkyle; R?5¿ représente un atome d'hydrogène ou un groupe C¿1-3? alkyle, C¿2-3? alcényle ou C¿2-3? alcynyle; R?6¿ représente un atome hydrogène ou un groupe C¿1-6? alkyle, C¿2-6? alcényle, C¿2-6? alcynyle, amino, C¿1-6? alkyle, C¿2-6? alcényle, C¿2-6? alcynyle, amino, C¿1-6? alcylamino, di (C¿1-6?) alkylamino C¿2-7? alkylamino ; R?7¿ et R?8¿ représentent, indépendamment, un atome d'hydrogène ou un atome d'halogène ou un hydroxy, trifluorométhyle, C¿1-6? alkyle, C¿2-6? alcényle, C¿2-6? alcynyle, C¿2-7? acyle, C¿1-6? alkylthio, C¿1-6? alcoxy, C¿3-6? cycloalkyle; et R?9¿ représente un atome d'hydrogène ou un atome d'halogène ou un groupe hydroxy, trifluorométhyle, C¿1-6? alkyle, C¿2-6? alcényle, C¿2-6? alcynyle, C¿2-7? acyle, C¿1-6? alkylthio, C¿1-6? alcoxy ou C¿3-6? cycloalkyle, ou des sels desdits composés qui sont utiles pour le traitement de troubles respiratoires tels que l'asthme. Les composés de ladite invention ont une durée d'action plus longue que celle du composé connu tréquinsine (9, 10-diméthoxy-3-méthyle-2-mésitylimino-2,3,6,7-tétrahydro-4H-pyrimido [6,1-a] isoquinoléin-4-one) et n'ont pas le goût très amer de la tréquinsine.

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