Guanidinylamino heterocycle compounds useful as alpha-2...

C - Chemistry – Metallurgy – 07 – D

Patent

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C07D 215/40 (2006.01) A61K 31/395 (2006.01) C07D 235/06 (2006.01)

Patent

CA 2272098

This invention involves compounds having the structure (1) (see figure I) wherein a) R1 is hydrogen; or C1-C3 alkanyl or C2-C3 alkenyl or nil; where R1 is nil, bond (a) is a double bond; b) D is CR2 and R2 is selected from hydrogen; unsubstituted C1-C3 alkanyl; amino, hydroxy, mercapto; C1-C3 alkylthio or C1- C3 alkoxy; C1-C3 alkylamino or C1-C3 dialkylamino and halo; or when B is CR3; D may be N; c) B is NR9, CR3=CR8, CR3=N, CR3, S, O, SO or SO2; wherein R9 is selected from hydrogen; and unsubstituted C1-C3 alkanyl, C2-C3 alkenyl or C2-C3 alkynyl; C3 cycloalkanyl, C3 cycloalkenyl; and wherein R3 and R8 are each independently selected from hydrogen; unsubstituted C1-C3 alkanyl, C2-C3 alkenyl or C2-C3 alkynyl; C3 cycloalkanyl, C3 cycloalkenyl; unsubstituted C1-C3 alkylthio or C1-C3 alkoxy; hydroxy; thio; nitro; cyano; amino; C1-C3 alkylamino or C1-C3 dialkylamino and halo; d) R4, R5 and R6 are each independently selected from hydrogen; unsubstituted C1- C3 alkanyl, C2-C3 alkenyl or C2-C3 alkynyl; C3 cycloalkanyl, C3 cycloalkenyl; unsubstituted C1-C3 alkylthio or C1-C3 alkoxy; hydroxy; thio; nitro; cyano; amino; C1- C3 alkylamino or C1-C3 dialkylamino; halo; and NH-C(=NR10)NHR11 (guanidinyl); wherein R10 and R11 are independently selected from hydrogen; methyl; and ethyl; and wherein one and only one of R4, R5 and R6 is guanidinyl; e) R7 is selected from hydrogen; unsubstituted C1-C3 alkanyl, C2-C3 alkenyl or C2-C3 alkynyl; C3 cycloalkanyl, C3 cycloalkenyl; unsubstituted C1-C3 alkylthio or C1-C3 alkoxy; hydroxy; thio; nitro; cyano; amino; C1-C3 alkylamino or C1-C3 dialkylamino and halo; and enantiomers, optical isomers, stereoisomers, diastereomers, tautomers, addition salts, bihydrolyzable 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.

L'invention concerne des composés qui correspondent à la structure (I) et sont décrits dans les revendications, ainsi que des énantiomères, isomères optiques, stéréo-isomères, diastéréomères, tautomères, sels d'addition, amides et esters biohydrolysables de ces composés. L'invention concerne également des compositions pharmaceutiques comprenant de tels nouveaux composés, ainsi que l'utilisation de ceux-ci dans le traitement ou la prévention de troubles induits par les adrénorécepteurs alpha-2.

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