PHTHALOCYANINE DERIVATIVE CONSISTING OF A MIXTURE OF 4 ISOMERS
There is described a phthalocyanine derivative of formula (I) consisting of 4 isomers wherein the relative isomer B content is less than or equal to 1% by weight.
1 . Phthalocyanine derivative of formula (I)
consisting of 4 isomers: A, B, C, D identified according to the symmetry classes D 2h , C 4h , C s , C 2v respectively,
wherein the isomer B is ≦1% by weight.
2 . Phthalocyanine derivative of formula (I) according to claim 1 wherein the isomer B is ≦1% by weight and isomer A is ≦12.5% by weight.
3 . Phthalocyanine derivative of formula (I) according to claim 1 wherein the isomer B is ≦0.2% by weight.
4 . Phthalocyanine derivative of formula (I) according to claim 1 wherein the isomer B is ≦0.2% by weight and isomer A is ≦12.5% by weight.
5 . Phthalocyanine derivative of formula (I) according to claim 4 wherein the isomers A/C/D are present in the following relative contents: 5.5-7.0%/56.0-63.5%/30.0-38.0%.
6 . Process for the preparation of a derivative of formula (I) according to claim 1 comprising a chromatographic purification of compound of formula (II)
to give the amine intermediate of formula (III).
7 . Process according to claim 6 wherein said chromatographic purification is carried out using a chromatographic column wherein the stationary phase is silica gel and the mobile phase is a constant or variable mixture of organic solvents.
8 . Process according to claim 7 wherein the silica gel is the stationary phase made of irregularly shaped or spherical shape silica gel particles, with particle size in the range 5-75 μm and pore size in the range 60-150 Angstrom.
9 . Process according to claim 7 wherein the stationary phase is used for more than one chromatographic run
10 . Process according to claim 7 wherein the mobile phase is constituted by at least two organic solvents comprising among dichloromethane, chloroform, ethyl acetate, acetone, tetrahydrofurane, N,N-dimethylformamide, methanol, ethanol, acetonitrile, diethyl ether, pentanes, hexanes, heptanes, petroleum ether, alkylamines.
11 . Process according to claim 7 wherein said mobile phase consists of two phases X and Y mixed in constant or variable manner along the time.
12 . Process according to claim 11 wherein X is constituted from at least 90% of chlorinated solvents and Y is constituted by pentanes, hexanes, heptanes, or petroleum ethers.
13 . Process according to claim 11 wherein X consists of a mixture of dichloromethane or chloroform with 0.1-10% of an agent or a mixture of agents with stronger elution power, comprising among tetrahydrofuran, ethyl acetate, methanol, ethanol, acetone, alkylamines and Y is constituted by pentanes, hexanes, heptanes, or petroleum ethers,
14 . Process according to claim 11 wherein X consists of a mixture 94/5/1 dichloromethane/tetrahydrofuran/methanol and Y consists of n-hexane or n-heptane.
15 . Compounds of formula (III)
and (IV)
as intermediates in the process according to claim 6 .
16 . Pharmaceutical compositions comprising as active principle a phthalocyanine derivative of formula (I) according to claim 1 in combination with pharmaceutically acceptable excipients and/or diluents, possibly in combination with chelating agents.
17 . (canceled)
18 . (canceled)
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20 . (canceled)
21 . (canceled)
22 . (canceled)
23 . (canceled)
24 . A method for the treatment of hypderproliferative diseases, psoriasis, actinic keratosis and pre-tumour or tumour pathologies with a pharmaceutical composition comprising as active principle a compound according to claim 1 .
25 . A method for the treatment by PDT of hyperproliferative diseases, psoriasis, actinic keratosis and pre-tumour or tumour pathologies with a pharmaceutical composition comprising as active principle a compound according to claim 1 .
26 . A method for the preventive or curative treatment of microbial infections with a pharmaceutical composition comprising as active principle a compound according to claim 1 .
27 . A method for the preventive or curative photodynamic treatment of microbial infections with a pharmaceutical composition comprising as active principle a compound according to claim 1 .
28 . A method for the incorporation of a pharmaceutical composition comprising as active principle a compound according to claim 1 as a component of medical devices.
29 . A method according to claim 28 wherein said medical devices are for the disinfection of wounds, as a sterilization agent, also ex vivo, and as in vivo diagnostic agent.
30 . A method for the preventive or curative treatment of microbial infections in animals with a pharmaceutical composition comprising as active principle a compound according to claim 1 .