Phthalocyanine dyes and their preparation and use

#The invention relates to novel substituted, water-soluble phthalocyanine dyes, their salts, a method of their preparation and their use in pharmaceutical compositions and medicaments for photodynamic therapy and for the treatment of infectious diseases induced by viruses, fungi or microbes, cancer and dermatological diseases.

#Photodynamic therapy is a method for treatment of tumors and other tissue alterations by light in combination with a light sensitive substance, a so-called photosensitizer, and oxygen contained in the tissue. Such a sensitizer or one of its metabolic precursors is administered to a patient. This sensitizer or metabolic precursor selectively accumulates in the tumor. After a certain waiting time, the tumor and the surrounding healthy tissue are irradiated with light of an appropriate wavelength. Photophysical processes generate toxic substances, so-called reactive oxygen species, from oxygen contained in the tissue. These reactive oxygen species selectively damage the tumor, because the sensitizer has selectively accumulated in the tumor tissue.

#In comparison to a surgical treatment, photodynamic therapy has the advantage of a non-invasive or only slightly invasive treatment. In particular, there is no need, for security reasons, for the removal of a large amount of healthy tissue near the tumor. Irradiation with light is from 10 to 100 minutes at a typical light intensity of from 100 mW/cm2 to 100 mW/cm2. The tissue is therefore only slightly heated. Photodynamic therapy of tumors normally needs only a single treatment, it is however possible to repeat the treatment. As light of normal wavelength is used, the impact on the patient is relatively small in comparison to a “classical” treatment.

#FIG. 1 is the dye normalized absorption spectra of the phthalocyanine dye (100) according to the invention in aqueous solution and in an aqueous solution of polyethylene glycol.

#The present invention relates to novel phthalocyanine dyes of general formula (II),

#wherein R1-R8 independently represent a linear or branched alkyl group having up to 8 carbon atoms; R9-R12 independently represent hydrogen, a linear or branched alkyl group having up to 8 carbon atoms or halogen; Me represents zinc, magnesium, aluminum, hydrogen, gallium, germanium or tin; M represents hydrogen, a metal cation or an ammonium cation, which optionally may be substituted by one or more unsubstituted or substituted alkyl or hyxdoxyalkoxyalkyl groups each having from 1 to 12 carbon atoms and m, n, o, p independently are 1 or 2.

#Phthalocyanine dyes, wherein m, n, o and p are equal to 1, are preferred.