Novel azobenzene derivatives, process for their preparation and their use for therapeutic treatment associated with ionizing radiations

A compound of formula (I):

• in which:
• M represents a metal atom selected from Ce(III), Pr(III), Nd(III), Sm(III), Eu(III), Gd(III), Tb(III), Dy(III), Ho(III), Er(III), Tm(III), Yb(III), Mg(II), Ca(II), Mn(II), Fe(II), Fe(III), Cu(II), Zn(II), Ga(III), Y(III), Zr(III), Tc(IV), Tc (VI), Tc (VII), Ru(II), Ru(III), Ru(IV), Pd(II), Ag(I), In(III), Hf (IV), Re(VI), W(II), W(III), W(IV), W(V), W(VI), Os(III), Os(IV), Ir(III), Ir (IV), Pt(II), Au(I), Au (III), Tl(III), Zr(IV), Nb(III), Bi(III);
• n is 1, 2, 3, 4, 5, 6, or 7;
• V and V′, which may be identical or different, are hydrogen atoms or linear or branched C1-C10 alkyl or alkoxy chains, or C1-C10 alkyl chains linked together and comprising one or more heteroatoms selected from N, O, or S, optionally substituted with one or more substituents independently selected from halogen atoms, and nitrile, nitro, thio, amino, amido, aryl, heteroaryl, hydroxyl, carboxylic acid or carboxylate groups, to form a ring;
• R1, R1′, R2, R2′, which may be identical or different, are hydrogen atoms, or linear or branched C1-C10 alkyl or alkoxy chains optionally substituted with one or more substituents independently selected from halogen atoms, and nitrile, nitro, thio, amino, amido, aryl, heteroaryl, hydroxyl, carboxylic acid or carboxylate groups;
• R3 and R3′, which may be identical or different, are hydrogen atoms or linear or branched C1-C10 alkyl or alkoxy chains optionally substituted with one or more substituents independently selected from halogen atoms, and nitrile, nitro, thio, amino, amido, aryl, heteroaryl, hydroxyl, carboxylic acid or carboxylate groups, or R3 and R3′ are linked together to form a 5- to 14-membered heterocycle or heteroaryl;
• m and m′, which may be identical or different, are equal to 1 or 2;
• X, X′, X″, X′″, Y, Y′, Y″, Y′″, which may be identical or different, are independently selected from H;
• halogen atoms;
• alkoxy, alkyl or cycloalkyl groups optionally interrupted or substituted with one or more heteroatom(s) or group(s) COOH, CONH2, COSH, OH, NH2, SH;
• 5- to 12-membered aryl or heteroaryl groups optionally substituted with one or more COOH, CONH2, COSH groups;
• COOH or NH2 groups;
• Z represents an alkyl group optionally interrupted or substituted with one or more heteroatom(s) or a COOH, CONH2, COSH, OH, NH2, SH group;
• a 5- to 12-membered aryl or heteroaryl group optionally substituted with one or more COOH, CONH2, COSH groups;
• or a COOH or NH2 group;
• W and W′, which may be the same or different, independently represent a CH2 group;
• or an aryl or cycloalkyl group;
• an oxygen or nitrogen atom (secondary or ternary);
• an amide linkage;
• an ester linkage;
• a thioether linkage;
• U and U′, which may be the same or different, represent the CH or NH group, it being understood that the double bond U═U′ is in cis or trans form;
• T represents a CH2 group;
• a —C(═O)NH group;
• an alkoxy, alkyl or cycloalkyl group optionally interrupted or substituted with one or more heteroatom(s) or a COOH, CONH2, COSH, OH, NH2, SH group;
• a 5- to 12-membered aryl or heteroaryl group containing one or more heteroatom(s) and/or optionally substituted with one or more groups chosen from COOalkyl, CONHalkyl, COSHalkyl;
• R represents H, or linear or branched C1-C18 alkyl or alkoxy chain, optionally substituted with one or more substituents independently selected from halogen atoms, and nitrile, nitro, thio, amino, amido, aryl, heteroaryl, hydroxyl, carboxylic acid or carboxylate groups;
• p and q are integers between 0 and 6, in particular between 1 and 6;
• wherein the n cationic charges of M are optionally neutralized by 0 to n carboxylate groups (—COOH) optionally substituted on R1, R1′, R2, R2′, R3, R3′, V, V′, and/or by 0 to n of the counterions present in solution if necessary;
• and cis and/or trans isomers and mixtures thereof.