Fused tropane-derivatives, their preparation and use

Details Fused tropane-derivatives, their preparation and use Fused tropane-derivatives, their preparation and use

C - Chemistry, Metallurgy

07

D

C07D 471/18 (2006.01) A61K 31/46 (2006.01) A61K 31/55 (2006.01) C07D 451/00 (2006.01)

Patent

CA 2236707

The present invention discloses compound of formula (I) or any of its enantiomers or any mixture thereof, a pharmaceutically acceptable addition salt thereof or the N-oxide thereof wherein X and Y together form =O, =S, =NOR2, =CR3R4, =N-CN, =N-NR7R8, -(CH2)m-, or -W'-(CH2)p-W"-, or one of X and Y is hydrogen and the other is -OR5, -SR5, or -NR5R6, Z is hydrogen, -COOR9; R3 and R4 are independently hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkynyl, alcoxy, aryl, arylalkyl, or -(CH2)q-COOR2; R2, R5 and R6 are independently hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkynyl, aryl, or arylalkyl, -CO-alkyl, or -SO2-alkyl; R7 and R8 are independently hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkynyl, aryl or arylalkyl; R9 is alkyl, alkenyl or alkynyl; R1 is alkyl, alkenyl, alkynyl, aryl, or arylalkyl; where said aryl groups may be substituted one or more times with substituents selected from the group consisting of halogen, CF3, CN, alkoxy, cycloalkoxy, alkyl, cycloalkyl, alkenyl, alkynyl, amino and nitro; W' and W" are each independently O or S; n is 1, 2, 3 or 4; m is 2, 3, 4 or 5; p is 1, 2, 3, 4, or 5; and q is 0, 1, 2, 3, or 4. The compounds possess valuable properties as monoamine neurotransmitter, i.e dopamine, and serotonine, reuptake inhibitors.

La présente invention concerne des composés de la formule (I) ou l'un quelconque de leurs énantiomères, ou tout mélange de ceux-ci, ou un sel d'addition d'acide de ces composés, ou un N-oxyde de ceux-ci. Dans cette formule, X et Y forment ensemble =O, =S, =NOR?2¿, =CR?3¿R?4¿, =N-CH, =N-NR?7¿R?8¿, -(CH¿2?)¿m?-, ou -W'-(CH¿2?)¿p?-W", ou bien l'un ou l'autre représente hydrogène, l'autre représentant -OR?5¿, -SR?5¿ ou -NR?5¿R?6¿, Z représente hydrogène, -COOR?9¿, R?3¿ et R?4¿ représentent indépendamment hydrogène, halogène, alkyle, cycloalkyle, cycloalkylalkyle, alcényle, alcynyle, alcoxy, aryle, arylalkyle ou -(CH¿2?)¿q?-COOR?2¿, R?2¿, R?5¿ et R?6¿ représentent indépendamment hydrogène, alkyle, cycloalkyle, cycloalkylalkyle, alcényle, alcynyle, aryle ou arylalkyle, -CO-alkyle ou -SO¿2?-alkyle, R?7¿ et R?8¿ représentent indépendamment hydrogène, alkyle, cycloalkyle, cycloalkylalkyle, alcényle, alcynyle, aryle ou arylalkyle, R?9¿ représente alkyle, alcényle ou alcynyle, R?1¿ représente alkyle, alcényle, alcynyle, aryle ou arylalkyle, les groupes aryles pouvant être substitués une ou plusieurs fois par des substituants choisis dans le groupe constitué par halogène, CF¿3?, CN, alcoxy, cycloalcoxy, alkyle, cycloalkyle, alcényle, alcynyle, amino et nitro, W' et W" représentent chacun indépendamment O ou S, n vaut 1, 2, 3 ou 4, m vaut 2, 3, 4 ou 5, p vaut 1, 2, 3, 4 ou 5 et q vaut 0, 1, 2, 3 ou 4. Ces composés possèdent des propriétés appréciables en tant que neurotransmetteurs de monoamines, c'est-à-dire en tant qu'inhibiteurs de recaptage de la dopamine et de la sérotonine.

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