Piperidino ureas as antidepressants

C - Chemistry – Metallurgy – 07 – D

Patent

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260/277, 260/294

C07D 211/58 (2006.01) C07D 211/72 (2006.01) C07D 213/75 (2006.01) C07D 401/02 (2006.01)

Patent

CA 1173037

ABSTRACT The invention concerns the preparation of compounds of formula Image (I) and acid addition and quaternary ammonium salts thereof, wherein the dotted line represents an optional bond, Ar represents a ring system of formula Image (Ia) in which Q is 0, 5, -CR7=CR8-, -N=CR8- and -N=N-; R4, R5 and R6, and R7 and R8 when present, each represent hydrogen or a substituent selected from lower alkyl, lower alkenyl, lower alkoxy, NO2, NH2, haloloweralkyl, hydroxyloweralkyl, aminoloweralkyl, substituted amino, loweralkoxycarbonyl, cyano, CONH2 and hydroxy; and additionally either R4 and R5 when adjacent or R6 and R8 when adjacent, together with the carbon atoms to which they are attached also represent a fused five or six membered carbocylic or heterocyclic ring optionally carrying one or more substituents as defined above; R is an optionally substituted aryl or heteroaryl radical or a cycloalkyl radical containing 5 to 7 carbon atoms; R1, R2, R3 and R9 are each hydrogen or a lower alkyl group; n is 0 or 1; X is =O, =S or =NH; Y is -O- or a direct bond and Z is -CO- or -CH2-, with the proviso that uhen Ar is unsubstituted phenyl and R9 is hydrogen then Y is -O-. The compounds of formula I exhibit psychotropic activity and are useful as antidepressants.

371466

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