Aryloxypropanolamine derivatives, method of preparation and applications thereof

Compounds of general formula I below:

• 26
• in which:
• R1, a substituent in the 2-, 3- or 4-position of the phenyl group, is a hydrogen atom, a halogen atom or one of the following groups:
• hydroxyl;
• C1-C10 lower alkyl selected in particular from methyl, ethyl, propyl, isopropyl, butyl and tert-butyl groups;
• C1-C10-alkoxy;
• benzyloxy;
• nitro;
• cyano;
• trifluoromethyl;
• or amino optionally substituted (monosubstituted or disubstituted) by 1 or 2 lower alkyl radicals as defined above;
• R2 is one of the following groups:
• —CH2—, —CH2—CH2—, —CH(CH3)—CH2—, —C(CH3)═CH—, —C(CH3)2—CH2—, or a bond;
• and
• Q is:
• (i) a phenyl radical 3,4-disubstituted by alkylenedioxy, which forms, with the phenyl radical, an unsubstituted benzodioxane unit, an unsubstituted benzodioxole unit or a benzodioxole unit 2-substituted by two radicals R3 and R4 according to the following formula:
• 27
• in which R3 and R4 are independently selected from the group comprising a hydrogen atom and a hydroxymethyl group;
• (ii) a 3- and/or 4-substituted phenyl radical of formula II below:
• 28
• Formula II
• in which:
• R5 is a hydrogen atom or a linear or branched C1-C6 lower alkyl radical;
• x is an integer between 1 and 3;
• and
• y is 0 or 1;
• (iii) a fused polycyclic hydrocarbon comprising at least two fused rings and selected from the following units:
• indene, indacene, naphthalene, azulene, biphenylene, acenaphthylene, fluorene, phenalene, phenanthrene and anthracene;
• or
• (iv) an optionally bridged, cyclic hydrocarbon system which consists of a cycloalkane comprising 1, 2 or 3 rings optionally containing substituents selected from methyl, ethyl, isopropyl, propyl, butyl and tert-butyl groups, the main ring containing 5 or 6 members.