Synthesis of long-wavelength absorbing photosensitizers

C - Chemistry – Metallurgy – 07 – F

Patent

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C07F 15/04 (2006.01) A61K 31/435 (2006.01) A61K 31/555 (2006.01) C07D 471/22 (2006.01) C07F 3/06 (2006.01)

Patent

CA 2254557

The present invention provides for novel therapeutic macrocycle compounds useful in photodynamic therapy that are based on the chlorin ring system. The macrocycle compounds have, in many cases, wavelengths of activation at about 670 nm, characteristic of chlorins, and are stabilized against oxidation by the attachment to the chlorin ring of a structure that comprises one or more exocyclic rings that contribute at least one nitrogen atom. Protonation or covalent modification of this nitrogen atom, or other covalent modification of the one or more exocyclic rings permits optimization of pharmacologically relevant properties including, for example, solubility. Representative chlorins include the pyridochlorins depicted as follows Image

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