Substituted metal-phthalocyanines, their preparation and the use thereof

1. Compounds of general formula(I)

in which;

M is selected from the group consisting of Zn, Si(OR 8 ) 2 , Ge(OR 8 ) 2 and AIOR 8 ;

R is H or a group selected from alkyl, alkenyl and alkyloxy group, linear or branched, having from 1 to 10 carbon atoms provided that, when R is different from H, the positions 8, 11, 15, 18, 22, 25 or 9, 10, 16, 17, 23, 24 are substituted; and

R 1 and R 2 , equal or different from one another, are H or a group (X) p R 3 , wherein X is selected from the group consisting of O, S, -NR 6 and -CH 2 -; and R 3 is

where: Y is selected from the group consisting of C 1-10 alkyl and phenyl, optionally substituted, or it forms with the Z group, to which it is bound, a saturated or unsaturated heterocycle, optionally substituted, which may contain up to two heteroatoms selected from the group consisting of N, O and S; Z is selected from the group consisting of -N, -CH 2 N and -CONHCH 2 CH 2 N; R 4 and R 5 , equal or different from one another, are selected from the group consisting of C 1-15 alkyl and phenyl, or form with the Z group, to which they are bound, a saturated or unsaturated heterocycle, optionally substituted, which may contain up to two heteroatoms chosen in the group consisting of N, O and S; R 6 and R 7 , equal or different from one another, are selected from the group consisting of H and C 1 -C 15 alkyl; m, n, p, w, t and u, independently from one another, are 0 or 1 ; and v is integer between 1 and 3 , provided that when R 1 and R 2 is different from H, the position 1 , 4 or 2 , 3 , whereas, when only one between R 1 and R 2 is different from H, the position 1 or 2 is substituted, or R 1 and R 2 , taken together, form a saturated or unsaturated heterocycle, possibly substituted, which may contain up to two heteroatoms selected from the group consisting of N, O and S; R 8 is selected from H and C 1 - C 15 alkyl.

2. A compound of formula(I) according to claim 1 , wherein M is Zn.

3. A compound of formula (I) according to claims 1 , wherein said saturated or unsaturated heterocycle is selected from the group consisting of morpholine, piperidine, pyridine, pyrimidine, piperazine, pyrrolidine, pyrroline, imidazole, aniline and julolidine.

4. A compound of formula (I) according to claim 1 , wherein the said group (X) p R 3 contains substituents bearing tertiary or quaternary nitrogen.

5. A compound of formula(I) according to claim 4 , wherein the said group (X) p R 3 is selected from the group consisting of:

6. A conjugates of a compound of general formal (I) according to claim 1 with a macromolecule selected from the group consisting of aminoacids, polypeptides, proteins and polysaccharides.

7. A pharmaceutical composition containing as the active principle a compound of general formula (I) according to claim 1 or mixtures thereof, optionally in combination with a pharmaceutically acceptable excipient.

8. A diagnostic agent containing as the active ingredient a compound of formula (I) according to claim 1 , optionally in combination with a pharmaceutically acceptable carrier.

9. A sterilizing agents for blood and blood derivative containing as the active ingredient a compound of formula (I) according to claim 1 , optionally in combination with a pharmaceutically acceptable carrier.

10. A pharmaceutical composition containing as the active ingredient a conjugate of compound of formula (I) according to claim 6 , or mixtures thereof, optionally in combination with pharmaceutically acceptable excipient.

11. A diagnostic agents containing as the active ingredient a conjugate of compound of formula (I) according to claim 6 , optionally in combination with a pharmaceutically acceptable carrier.

12. A sterilizing agent for blood and blood derivative containing as the active ingredient a conjugate of compounds of formula (I) according to claim 6 , optionally in combination with a pharmaceutically acceptable carrier.

13. A compound of formula (I) according to claim 1 , wherein:

R=R 2 =H, and R 1 =1,3-bis-(dimethylamino)2-propyloxy in position 2;

R=R 2 =H, and R 1 =pyridin-∝yl-oxy in position2;

R=R 2 =H, and R 1 =3-(dimethylamino)phenoxy in position 2 ;

R=R 2 =H, and R 1 =1-methylpiperidin-4yl-oxy in position 2 ;

R=H, and R 1 =R 2 =pyridin-4yl-oxy in positions 2, and 3;

R=R 2 =H, and R 1 =1,3-bis-(dimethylamino)2-propyloxy in position 1;

R=H, and R 1 =R 2 =3-(piperidin-1 yl)propyloxy in positions 1, and 4;

R=H, and R 1 =R 2 =3-(dimethylamino)phenoxy in positions 2 , and 3;

R=R 2 =H, and R 1 =pyridin-2-yl-oxy in position 2;

R=R 2 =H, and R 1 =pyridin-3-yl-oxy in position 2;

R=R 2 =H, and R 1 =3-(dimethylamino)phenoxy in position 1;

R=H, and R 1 =R 2 =2-(diethylamino)ethylthio in positions 2and 3 ;

R=H, and R 1 =R 2 =pyridin-3-yl-oxy in positions 2, and 3;

R=R 2 =H, and R 1 =2-(dimethylamino)ethyloxy in position 1;

R=R 2 =H, and R 1 =2-(piperidin-1-yl)ethyloxy in position 1;

R=R 2 =H, and R 1 =2-(piperidin-1-yl)ethyloxy in position 2;

R=R 2 =H, and R 1 =N-(2-aminoethyl)benzamidoyl-4-oxy trifluoro acetate;

R=R 2 =H, and R 1 =1,3-bis-(trimethylammonium)2-propyloxy diiodide in position 2;

R=R 2 =H, and R 1 =3-(trimethylammonium)phenoxy iodide in position 2;

R=R 2 =H, and R 1 =1,1-dimethylpiperidinium-4-yl-oxy iodide in position 2;

R=H, and R 1 =R 2 =3-(1-methylpiperidinium-1-yl) propyloxy iodide in positions 1, and;

R=H, and R 1 =R 2 =3-(trimethylammonium)phenoxy iodide in positions 2, and 3;

R=R 2 =H, and R 1 =R 2 =1,3-bis-(trimethylammonium)2-propyloxy diiodide in position 1;

R=R 2 =H, and R 1 =R 2 =3-(trimethylammonium)phenoxy iodide in position 1;

R=H, and R 1 =R 2 =2(diethylmethylammonium)ethylthio iodide in positions 2, and 3; and

R=R 2 =H, and R 1 =1-methylpyridinium-4-yl-oxy in position 2.