Phthalocyanine derivative consisting of a mixture of 4 isomers

Abstract

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) 
     
     
         19 . (canceled) 
     
     
         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 .