Patent NZ-330910-A (NZ)
Title: Substituted N-methyl-N-(4-(piperidin-1-yl)-2-(aryl)butyl)benzamides useful for the treatment of allergic diseases
Inventor: MAYNARD GEORGE DANIEL
IPC: C07D401/04
Filed: 1997-01-27
Abstract: A compound of the formula (I) wherein: R' is from 1 to 3 substituents each independently chosen from the group consisting of hydrogen, halogen, alkyl, and alkoxy; R" is hydrogen or a triazole radical optionally substituted with alkyl or CF3; Ar1 is a radical of formulae (II) wherein: R1 is from 1 to 3 substituents each independently chosen from the group consisting of hydrogen, halogen, hydroxy, -CF3, alkyl, and alkoxy; R2 is from 1 to 2 substituents each independently chosen from the group consisting of hydrogen, halogen, alkyl, and alkoxy; X1 and X2 are as defined in one of parts A), B), or C): A) X1 is hydrogen and X2 is a radical chosen formulae (III) wherein : p is 1 or 2; R3 and R4 are independently selected from 1 to 3 substituents each independently chosen from the group consisting of hydrogen, halogen, -CF3, alkyl, and alkoxy; R5 is hydrogen or hydroxy; Ar2 is a radical chosen from formulae (IV) wherein: R6 is from 1 to 3 substituents each independently chosen from the group consisting of hydrogen, halogen, -CF3, alkyl, alkoxy, and -CO2R9 wherein R9 is chosen from the group consisting of hydrogen and alkyl; R7 is from 1 to 2 substituents each independently chosen from the group consisting of hydrogen, halogen, alkyl, and alkoxy; R8 is chosen from the group consisting of hydrogen,-CH3, and -CH2OH; R10 is chosen from the group consisting of hydrogen, alkyl, and benzyl; Z is chosen from the group consisting of hydrogen, alkyl, -(CH2)w-O-(CH2)t-Y, -(CH2)fA, -(CH2)uCO2R11, -(CH2)uC(O)NR12R13, -(CH2)gC(O)(CH2)hCH3, -(CH2)w-O-Ar3, -CH2CH20CF3, -CH2CF3, -CH2CH2CH2CF3, -(CH2)2CH=CH2, -CH2CH=CH2, -CH2CH=CHCH3, -CK2CH=CKCK2CH3, -CH2CH=C(CH3)2, and -CH2OCH2CH2Si(CH3)3 wherein w is an integer from 2 to 5; t is an integer from 1 to 3; f is 2 or 3; u is an integer from 1 to 4; ; g is an integer from 1 to 3; h is an integer from 0 to 3; w is an integer from 2 to 4; Y is chosen from the group consisting of hydrogen, -CF3, -CH=CH2, -CH=C(CH3)2, and -CO2R14 wherein R14 is chosen from the group consisting of hydrogen and alkyl; A is chosen from the group consisting of -NR15R16, acetylamino, and morpholino wherein R15 is chosen from the group consisting of hydrogen and alkyl and R16 is alkyl; R11 is chosen from the group consisting of hydrogen and alkyl; R12 is chosen from the group consisting of hydrogen, alkyl, and benzyl; R13 is chosen from the group consisting of hydrogen and alkyl; Ar3 is a radical chosen from the group consisting of (V) wherein: v is an integer from 1 to 3; R17 is chosen from the group consisting of hydrogen and -C02R18 wherein R18 is chosen from the group consisting of hydrogen and alkyl; B) X1 is hydroxy and X2 is a radical chosen from the group consisting of formulae (VI) wherein p, R3, Z, and Ar2 are as previously defined; C) X2 is a radical of the formula (VII) wherein R3 and R4 are as previously defined; and X1 and Z1 taken together form a second bond between the carbon atoms bearing X1 and Z1; and stereoisomers and pharmaceutically acceptable salt thereof. The compounds are useful for treating allergic rhinitis, asthma, emesis and inflammatory bowel disease.