2-imidazolinylaminobenzoxazole compounds useful as alpha-2...

C - Chemistry – Metallurgy – 07 – D

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C07D 413/12 (2006.01) A61K 31/42 (2006.01)

Patent

CA 2272683

This invention involves compounds having structure (I) wherein: a) R1, R2 and R3 are each independently selected from hydrogen; unsubstituted C1-C3 alkanyl, alkenyl or alkynyl; cycloalkanyl, cycloalkenyl; unsubstituted C1-C3 alkylthio or alkoxy; hydroxy; thio; nitro; cyano; amino; C1-C3 alkylamino or C1-C3 dialkylamino and halo; b) R4 is selected from hydrogen; unsubstituted C1-C3 alkanyl; amino, hydroxy, mercapto; C1-C3 alkylthio or alkoxy; C1-C3 alkylamino or C1-C3 dialkylamino and halo; c) R5 is hydrogen; or alkyl or nil; d) where R5 is nil, bond (a) is a double bond; e) the imidazolinylamino moiety is attached to the 5- or 6- position of the benzoxazole ring; and enantiomers, optical isomers, stereoisomers, diastereomers, tautomers, addition salts, biohydrolyzable amides and esters thereof, as well as pharmaceutical compositions comprising such novel compounds. The invention also relates to the use of such compounds for preventing or treating disorders modulated by alpha-2 adrenoceptors.

La présente invention concerne non seulement un composé représenté par la formule générale (I), mais également des énantiomères, des isomères optiques, des stéréoisomères des diastéréomères, des tautomères, des sels d'addition, certains de leurs amides ou de leurs esters biohydrolysables, ainsi que des compositions pharmaceutiques contenant de tels composés. L'invention concerne également l'utilisation de ces composés pour la prévention ou le traitement de troubles imputables à la modulation par les adrénorécepteurs .alpha.-2. Dans la formule générale (I), a) R¿1? R¿2? et R¿3? sont choisis chacun indépendamment dans le groupe des alcanyl, alcényl ou alkynyl en C¿1?-C¿3? non substitués; cyclonacanyl, cycloalcényl; alkylthio ou alcoxy en C¿1?-C¿3? non substitués; hydroxy; thio; nitro; cyano; amino; C¿1?-C¿3? alkylamino ou C¿1?-C¿3? dialkylamino et halo; b) R¿4? est choisi dans le groupe des hydrogène, alcanyl, en C¿1?-C¿3? non substitués; amino, hydroxy, mercapto; alkylthio ou alcoxy en C¿1?-C¿3?; alkylamino en C¿1?-C¿3? ou dialkylamino en C¿1?-C¿3? et halo; c) R¿5? est nul, ou alkyl ou nul; d) lorsque R¿5? est nul, la liaison (a) est une double liaison; e) le groupe fonctionnels imidazolinylamino est rattaché aux positions 5- ou 6- du cycle benzoxazole.

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