Derivatives of azetidine and pyrrolidine

C - Chemistry – Metallurgy – 07 – D

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Details

C07D 205/04 (2006.01) A61K 31/395 (2006.01) A61K 31/40 (2006.01) C07D 207/12 (2006.01) C07D 401/12 (2006.01) C07D 409/12 (2006.01)

Patent

CA 2321188

The invention relates to a compound having formula (I) wherein A is an optionally unsaturated 5- or 6-membered ring, which may comprise a heteroatom selected from N, 0 and S and which may be substituted with oxo or (1-6C)alkyl; R1, R2 and R3 are independently H, (1-6C)alkyl, (1-6C)alkoxy, (1-6C)alkoxy-(1-6C)alkyl, carbo(1-6C)alkoxy or halogen; X is O or S; and n is 1 or 2; or a pharmaceutically acceptable salt thereof, with the exception of 3-(naphth-1-yl-oxy)-pyrrolidin and 3-(5,6,7,8-tetrahydro-naphth-1-yl-oxy)-pyrrolidin. The compounds of the invention have antidepressant activity and can be used in treating or preventing serotonin-related diseases.

L'invention concerne un composé de formule (I), dans laquelle A est un noyau à 5 ou 6 éléments éventuellement insaturé, qui peut renfermer un hétéroatome choisi entre N, O et S et qui peut être substitué par oxo ou par alkyle C1-C6; R<1>, R<2> et R<3> sont indépendamment H, alkyle C1-C6, alcoxy C1-C6, alcoxy C1-C6-alkyle C1-C6, carbo-alcoxy C1-C6 ou halogène; X est O ou S; et n est 1 ou 2; ou un sel pharmaceutiquement acceptable dudit composé, à l'exception de la 3-(naphth-1-yl-oxy)-pyrrolidine et de la 3-(5,6,7,8-tétrahydro-naphth-1-yl-oxy)-pyrrolidine. Ces composés sont des antidépresseurs et peuvent être utilisés pour traiter ou prévenir les pathologies en rapport avec la sérotonine.

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