Arylalkylamines, process for preparing them and pharmaceutical compositions containing them

Process for the preparation of a compound of Formula (I):

• ##STR124## wherein Y represents either
• a group Cy--N in which Cy represents a phenyl, unsubstituted or substituted one or more times with a substituent selected from the group consisting of hydrogen, a halogen atom, a hydroxyl , a C.sub.1 -C.sub.4 alkoxy, a C.sub.1 -C.sub.4 alkyl, a trifluoromethyl, the said substituents being identical or different;
• a C.sub.3 -C.sub.7 cycloalkyl group, a pyrimidinyl group or a pyridyl group;
• or
• a group ##STR125## in which Ar represents a phenyl, pyridyl or thienyl group, said phenyl group being unsubstituted or substituted one or more times with a substituent selected from the group consisting of hydrogen, a halogen atom, a hydroxyl, a C.sub.1 -C.sub.4 alkoxy, a trifluoromethyl, a C.sub.1 -C.sub.4 alkyl, the said substituents being identical or different;
• x is zero or one;
• and
• X represents a hydroxyl, a C.sub.1 -C.sub.4 alkoxy;
• a hydroxyalkyl in which the alkyl is a C.sub.1 -C.sub.3 group;
• a C.sub.1 -C.sub.4 acyloxy;
• a phenacyloxy;
• a carboxyl;
• a C.sub.1 -C.sub.4 carbalkoxy;
• a cyano;
• an aminoalkylene in which the alkylene is a C.sub.1 -C.sub.3 group;
• a group --N--(X.sub.1).sub.2 in which the groups X.sub.1 independently represent hydrogen or C.sub.1 -C.sub.4 alkyl;
• a group ##STR126## in which Alk represents a C.sub.1 -C.sub.6 alkyl;
• a group ##STR127## in which Alk.sub.1 is a C.sub.1 -C.sub.3 alkylene and Alk'.sub.1 is a C.sub.1 -C.sub.3 alkyl;
• a C.sub.1 -C.sub.4 acyl;
• a group --S--X.sub.2 in which X.sub.2 represents hydrogen or C.sub.1 -C.sub.4 alkyl;
• or alternatively X is a double bond between the carbon atom to which it is linked and the adjacent carbon in the heterocycle;
• m is 2 or 3;
• Ar' represents a phenyl, unsubstituted or substituted one or more times with a substituent selected from the group consisting of hydrogen, a halogen atom, a trifluoromethyl, a C.sub.1 -C.sub.4 alkoxy, a C.sub.1 -C.sub.4 alkyl, the said substituents being identical or different;
• a thienyl;
• a benzothienyl;
• a naphthyl;
• an indolyl;
• or an indolyl N-substituted with a C.sub.1 -C.sub.3 alkyl;
• R represents hydrogen or C.sub.1 -C.sub.4 alkyl;
• T represents a group selected from ##STR128## W being an oxygen or sulphur atom, and Z represents either hydrogen, or M or OM when T represents a ##STR129## group, or M when T represents a group ##STR130## M representing a C.sub.1 -C.sub.6 alkyl;
• a phenylalkyl in which the alkyl is a C.sub.1 -C.sub.3 group, optionally substituted on the aromatic ring with a halogen, a trifluoromethyl, a C.sub.1 -C.sub.4 alkyl, a hydroxyl, a C.sub.1 -C.sub.4 alkoxy;
• a pyridyl alkyl in which the alkyl is a C.sub.1 -C.sub.3 group;
• a naphthylalkyl in which the alkyl is a C.sub.1 -C.sub.3 group, optionally substituted on the naphthyl ring-system with a halogen, a trifluoromethyl, a C.sub.1 -C.sub.4 alkyl, a hydroxyl, a C.sub.1 -C.sub.4 alkoxy;
• a pyridylthioalkyl in which the alkyl is a C.sub.1 -C.sub.3 group;
• a styryl;
• or an optionally substituted mono-, di- or tricyclic aromatic or heteroaromatic group;
• or a salt of a compound of Formula I with an inorganic or organic acid;
• the process comprising the steps of:
• (a) reacting a free amine of Formula (II) ##STR131## in which m, Ar' and R are as defined above and E represents an O-protecting group or a group ##STR132## in which Y is defined as above wherein, when Y represents a group ##STR133## in which X is a hydroxyl, this hydroxyl may be protected;
• or a free amine of Formula (II'") ##STR134## in which m, Ar' and R are as defined above, with either a functional derivative of an acid of formula
• HO--CO--Z (III)
• in which Z is as defined above when a compound of Formula (I) in which T is --CO-- is to be prepared, or
• an iso(thio)cyanate of formula:
• W.dbd.C.dbd.N--Z (III')
• in which W and Z are as defined above, when a compound of Formula (I) in which T is --C(W)--NH-- is to be prepared,
• to form the compound of Formula (IV) ##STR135## (b) then, when E represents tetrahydropyranyloxy as an O-protecting group, removing the tetrahydropyranyl group by the action of an acid, said deprotection optionally being carried out directly on the compound of Formula (II) in order to yield a compound of Formula (II") which is then treated with a compound of Formula (III) or (III');
• (c) reacting the N-substituted alkanolamine thereby obtained, of formula:
• ##STR136## with methanesulphonyl chloride;
• (d) reacting the mesylate thereby obtained, of formula:
• ##STR137## with a secondary amine of formula:
• ##STR138## in which Y is as defined above;
• and (e) after deprotection, where appropriate, of the hydroxyl represented by X, optionally converting the product thereby obtained to one of its salts.