4-arylmethyloxymethyl piperidines as tachykinin antagonists

Details 4-arylmethyloxymethyl piperidines as tachykinin antagonists 4-arylmethyloxymethyl piperidines as tachykinin antagonists

C - Chemistry, Metallurgy

07

D

C07D 211/08 (2006.01) A61K 31/395 (2006.01) A61K 31/695 (2006.01) C07D 207/08 (2006.01) C07D 211/22 (2006.01) C07D 211/96 (2006.01) C07D 401/00 (2006.01) C07D 401/06 (2006.01) C07D 401/12 (2006.01) C07D 403/00 (2006.01) C07D 405/00 (2006.01) C07D 409/00 (2006.01) C07D 413/00 (2006.01) C07D 413/06 (2006.01) C07D 417/06 (2006.01) C07D 453/02 (2006.01) C07D 521/00 (2006.01) C07F 7/10 (2006.01)

Patent

CA 2146767

Compounds of formula (I) wherein m is 2, 3 or 4; n is 0, 1 or 2 when m is 2 or 3, and n is 0 or 1 when m is 4; X represents O or S; R1 represents phenyl optionally substituted by 1, 2 or 3 groups selected from C1-6alkyl, C2-6alkenyl, C2-6alkynyl, halo, cyano, nitro, trifluor- omethyl, trimethylsilyl, -ORa, SRa, SORa, SO2Ra, -NRaRb, -NRaCORb, -NRaCO2Rb, -CO2Ra or -CONRaRb, where Ra and Rb each independently represent H, C1-6alkyl, phenyl or trifluoromethyl; R2 represents phenyl optionally substituted by 1, 2 or 3 groups selected from C1-6alkyl, C2-6alkenyl, C2-6alkynyl, halo, cyano, nitro, trifluoromethyl, trimethylsilyl, -ORa, SRa, SORa, SO2Ra, -NRaRb, -NRaCORb, -NRaCO2Rb, -CO2Ra or -CONRaRb, where Ra and Rb are as previously defined; heteroaryl selected from indazolyl, thienyl, fu- ryl, pyridyl, thiazolyl, tetrazolyl and quinolyl; benzhydryl; or benzyl; wherein each heteroa- ryl and each phenyl moiety of benzyl and benzhydryl may be substituted by C1-6alkyl, C1-6alkoxy, halo or trifluoromethyl; and R3 represents H, COR9, CO2R10, CO- CONR10R11, COCO2R10, SO2R15, CONR10SO2R15, C1-6alkyl optionally substituted by agroup selected from (CO2R10, CONR10R11, hydroxy, cyano, COR9, NR10R11, C(NOH)NR10R11, CONHphenyl(C1-4alkyl), COCO2R10, COCONR10R11, SO2R15, CONR10SO2R15 and phenyl optionally substituted by one or more substituents selected from C1-6alkyl, C1-6alkoxy, halo and trifluoromethyl), Y-R8 or CO-Z- (CH2)q-R12; R4, R5, R6 and R7 each independently represent H or C1-6alkyl; R8 represents an optionally substituted aro- matic heterocycle; R9 represents H, C1-6alkyl or phenyl; R10 and R11 each independently represent H or C1-6alkyl; R12 re- presents NR13R14 or an optionally substituted aromatic or non-aromatic azacyclic or azabicyclic group; R13 and R14 each independently represent H, C1-6alkyl, phenyl optionally substituted by one or more of C1-6alkyl, C1-6alkoxy, halo or trifluor- omethyl or phenylC1-4alkyl optionally substituted in the phenyl ring by one or more of C1-6alkyl, C1-6alkoxy, halo or triflu- oromethyl; R15 represents C1-6alkyl, trifluoromethyl or phenyl optionally substituted by one or more substituents selected from C1-6alkyl, C1-6alkoxy, halo and trifluoromethyl; Y represents a hydrocarbon chain of 1, 2, 3 or 4 carbon atoms which way optionally be substituted by oxo; Z represents CH2, O, S or NR10; and q represents 0, 1, 2, 3, 4, 5 or 6 and their salts are useful as tachykinin antagonists.

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