Substituted compounds derived from N-(benzyl)phenylacetamide, preparation and uses

A substituted N-(benzyl)phenylacetamide derivative, wherein it is represented by formula (II) below:

• in which,
• G represents:
• A NRaRb radical, cyclic or not;
• or
• A —NR′aCOR′b;
• or
• A —OR′a, —SR′a;
• or
• A —SORc or —SO2Rc radical;
• Ra and Rb, identical or different, substituted or not, representing a hydrogen atom or an alkyl, alkenyl, aryl, aralkyl radical or a heterocycle;
• Alternatively, Ra and Rb can form together a heterocycle with the nitrogen atom to which they are attached;
• R′aand R′b, identical or different, substituted or not, represent a hydrogen atom or an alkyl, alkenyl, aryl, aralkyl radical or a heterocycle;
• Alternatively, R′a and R′b can form together a heterocycle with the nitrogen atom,
• Rc representing an alkyl, alkenyl, aryl, aralkyl type radical or a heterocycle;
• G possibly being able to form a heterocycle with X1;
• R1 represents an alkyl, alkenyl, aryl, aralkyl type radical or a heterocycle;
• R2, R3 and R4 independently represent a hydrogen atom, an alkyl, alkenyl, aryl, aralkyl type radical or a heterocycle;
• R1 and R4 each, independently, being able to be linked to the molecular skeleton by a double linkage, R2 or R3 then being absent;
• R represents a hydrogen atom or an alkyl, alkenyl, aryl, aralkyl type radical or a heterocycle;
• Y represents an oxygen atom, a sulphur atom (possibly oxidised to sulphoxide or sulphone function), an amine group of the NR type (R being as defined above, in particular a hydrogen atom or an alkyl radical) or a selenium atom (possibly oxidised to selenoxide or selenone function);
• E represents:
• An alkyl or alkenyl chain, substituted by one or more W groups as defined below;
• or
• A chain corresponding to the formula —(CH2)m—Y1-Z-Y2-(CH2)n—CR5R6—W;
• in which,
• R5 and R6 independently represent a hydrogen atom, a halogen atom or an alkyl, alkenyl, aryl, aralkyl, —OR′a or —SR′a radical;
• alternatively R5 and R6 may form together a cycle,
• m and n independently represent an integer between 0 and 10;
• Y1 and Y2 independently represent a covalent linkage or a heteroatom chosen from nitrogen (of the NR type, R being as defined above, in particular a hydrogen atom or an alkyl radical), oxygen or sulphur;
• Z represents a covalent linkage or an alkyl, alkenyl, aryl, aralkyl radical;
• W represents:
• a carboxyl radical or a derivative, preferably of the —COOH, —COOR′a, —COSR′a, —CONR′aR′b, —CSNR′aR′b type;
• or
• an isosteric group of the carboxyl radical, preferably an acylsulphonamide (—CONHSO2Rc) or tetrazolyl radical;
• or
• sulphonic acid (—SO3H) or a derivative of the —SO3R′a or —SO2NR′aR′b type;
• R′a, R′b and Rc being as defined above;
• X1, X2, X3 and X4 independently represent a hydrogen or halogen atom, an —NO2 or —CN function, an alkyl, alkenyl, aryl, aralkyl, —OR′a, —SR′a, —NR′aR′b, —SORC or —SO2Rc, radical or a heterocycle;
• R′a, R′b and Rc being as defined above;
• X1 and X3 each being able to form a cycle (aromatic or not, heterocyclic or not) with X2 and X4 respectively;
• the optical and geometric isomers, racemates, tautomers, salts, hydrates and mixtures thereof.

Derivative selected in the group consisting of:

• 4-[1-(3-methyl-1-(2-(1-piperidinyl)phenyl)butyl)aminocarbonylmethyl]phenol;
• 4-[1-methyl-1-[1-(3-methyl-1-(2-(1-piperidinyl)phenyl)butyl)aminocarbonyl]methyl]phenol;
• 4-[1-(1-(2-(1-piperidinyl)phenyl)pentyl)aminocarbonylmethyl]phenol;
• 4-[1-(1-(2-(1-piperidinyl)phenyl)heptyl)aminocarbonylmethyl]phenol;
• N-ethyl-N-[4-[1-(3-methyl-1-(2-(1-piperidinyl)phenyl)butyl)aminocarbonylmethyl]phenyl]amine;
• 2-[1-(1-(2-(1-piperidinyl)phenyl)pentyl)aminocarbonylmethyl]phenol;
• 2-chloro-4-[1-(3-methyl-1-(2-(1-piperidinyl)phenyl)butyl)aminocarbonylmethyl]phenol;
• 4-[1-(1-(2-(1-piperidinyl)phenyl)butyl)aminocarbonylmethyl]phenol;
• 4-[1-(2-phenyl-1-(2-(1-piperidinyl)phenyl)ethyl)aminocarbonylmethyl]thiophenol;
• 4-[1-(1-(2-(diethylamino)phenyl)pentyl)aminocarbonylmethyl]phenol.