Patent JP-H05140103-A (JP)
Title: New n-alkylpiperidino compound and its enantiomer, method of their synthesis, and drug composition containing them
Inventor: ZABIE EMON ARUTO
IPC: A61K9/48
Filed: 1992-05-06
Abstract: The invention relates to compounds of formula: <IMAGE>  in which:     - m is equal to 2 or 3; - Ar represents a phenyl which is unsubstituted or substituted one or more times by a halogen atom, preferably a chlorine or fluorine atom, by a C1-C3 alkyl, by a trifluoromethyl, by an alkoxy in which the alkyl is C1-C3, by a hydroxyl or by a methylenedioxy; a thienyl, pyridyl or imidazolyl group which is unsubstituted or substituted by a C1-C3 alkyl; - Ar' represents a phenyl group which is unsubstituted or mono- or disubstituted by a halogen atom, preferably a chlorine or fluorine atom, by a C1-C3 alkyl, by a trifluoromethyl, by an alkoxy in which the alkyl is C1-C3, by hydroxyl or by a methylenedioxy; a thienyl group; an imidazolyl group or a benzothienyl group which is unsubstituted or substituted by a halogen, preferably by a chlorine or fluorine atom; a naphthyl group which is unsubstituted or substituted by a halogen, preferably by a fluorine atom; a biphenyl group; an indolyl which is unsubstituted or substituted on the nitrogen by a benzyl group; - X represents an oxygen atom, a sulphur atom, a sulphone or a sulphoxide, an -NH- group, a group <IMAGE> or a group <IMAGE> in which Alk is a C1-C3 alkyl group or a group <IMAGE> in which Alk represents a C1-C3 alkylene and X1 and X2 independently represent hydrogen, a C1-C3 alkyl or constitute, with the nitrogen atom to which they are bonded, a heterocycle chosen from pyrrolidine, piperidine or morpholine; - Q represents hydrogen, a C1-C4 alkyl group or an aminoalkyl group of formula -(CH2)q-Am', where q is 2 or 3 and Am' is a piperidino, 4-benzylpiperidino or dialkylamino group, it being possible for each alkyl to contain from 1 to 4 carbon atoms; - R represents hydrogen, a methyl group or a group (CH2)n-L, where n is an integer from 2 to 6 and L is hydrogen or an amino group;   - T represents a group chosen from: <IMAGE> W being an oxygen or sulphur atom, and   - Z represents either M or OM when T represents:  the group <IMAGE> or M when T represents the group <IMAGE> M represents hydrogen or a straight or branched C1-C6 alkyl; an  alpha -hydroxybenzyl, an  alpha -alkylbenzyl or a phenylalkyl in which the alkyl group comprises 1 to 3 carbon atoms, unsubstituted or mono- or polysubstituted on the aromatic ring by a halogen, a hydroxyl, an alkoxy containing 1 to 4 carbon atoms, or an alkyl containing 1 to 4 carbon atoms; a pyridylalkyl in which the alkyl group comprises 1 to 3 carbon atoms; a naphthylalkyl in which the alkyl group comprises 1 to 3 carbon atoms; a pyridylthioalkyl in which the alkyl group comprises 1 to 3 carbon atoms; a styryl; a 1-methylimidazol-2-ylthioalkyl in which the alkyl group comprises 1 to 3 carbon atoms; a 1-oxo-3-phenylindan-2-yl; an unsubstituted, mono- or polysubstituted aromatic or heteroaromatic group; or to one of their salts with inorganic or organic acids or to one of their quaternary ammonium salts formed with the nitrogen of piperidine. Application: Antagonists of receptors of neurokines (neurokins).