N-alkylenepiperidino compounds and their enantiomers,...

C - Chemistry – Metallurgy – 07 – D

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C07D 211/34 (2006.01) A61K 31/445 (2006.01) A61K 31/495 (2006.01) A61K 31/535 (2006.01) C07D 211/46 (2006.01) C07D 211/54 (2006.01) C07D 211/58 (2006.01) C07D 401/06 (2006.01) C07D 401/12 (2006.01) C07D 405/00 (2006.01) C07D 409/00 (2006.01) C07D 413/00 (2006.01) C07D 417/00 (2006.01)

Patent

CA 2067924

Image in which: - m is equal to 2 or 3; - Ar represents a phenyl, unsubstituted or substituted one or more times with a halogen atom, preferably a chlorine or fluorine atom, with a C1-C, alkyl, with a trifluoromethyl, with an alkoxy in which the alkyl is a C1-C, group, with a hydroxyl or with a methylenedioxy; a thienyl, pyridyl or imidazolyl group which is or is not substituted with a C1-C, alkyl; - Ar' represents a phenyl group, unsubstituted or mono- or di-substituted with a halogen atom, preferably a chlorine or fluorine atom, with a C1-C, alkyl, with a trifluoromethyl, with an alkoxy in which the alkyl is a C1-C, group, with a hydroxyl or with a methylenedioxy; a thienyl group; an imidazolyl group or a benzothienyl group, each of which is unsubstituted or substituted with a,halogen, preferably with a chlorine or fluorine atom; a naphthyl group unsubstituted or substituted with a halogen, preferably with a fluorine atom; a biphenyl group; an indolyl unsubstituted or substituted on the nitrogen with a benzyl group; - X represents an oxygen atom, a sulphur atom, a sulphone or a sulphoxide, an -NH- group, an I Image group or an group in which Alk is a Image C1-C3 alkyl group; an Image group in which Alk represents a C1-C3 alkylene and X1 and X2 represent, independently, hydrogen, a C1-C3 alkyl or form, together with the nitrogen atom to which they are bonded, a heterocycle chosen from amongst 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 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 selected from Image W being an oxygen or sulphur atom, and - Z represents either M or OM when T represents the group, or M when T represents Image the group M represents hydrogen or a linear or branched C1-C6 alkyl; an .alpha.-hydroxybenzyl, an .alpha.-alkylbenzyl or a phenylalkyl in which the alkyl contains 1 to 3 carbon atoms, unsubstituted, mono- or polysubstituted on the aromatic ring with a halogen, a hydroxyl, an alkoxy of 1 to 4 carbon atoms, an alkyl of 1 to 4 carbon atoms; a pyridylalkyl in which the alkyl group contains 1 to 3 carbon atoms; a naphthylalkyl in which the alkyl group contains 1 to 3 carbon atoms; a pyridylthioalkyl in which the alkyl group contains 1 to 3 carbon atoms; a styryl; a 1-methyl-2-imidazolylthioalkyl in which the alkyl group contains 1 to 3 carbon atoms; a 1-oxophenyl-3-indan-2-yl; an unsubstituted, mono- or polysubstituted aromatic or heteroaromatic group; or one of their salts with inorganic or organic acids or one of their quaternary ammonium salts. Application: antagonists of neurokinin receptors.

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