PROCESS FOR THE PREPARATION OF PORPHYRIN DERIVATIVES AS ANTIMICROBIAL AGENTS BY PHOTODYNAMIC THERAPY (PDT)

摘要

There is provided a process for the preparation of 5,15-bis-[4-(3-trimethylammonio-propyloxy)-phenyl]-porphyrin dihalide, wherein the process comprises step (a) of providing 4-(3-bromopropyloxy)benzaldehyde, step (b) of providing dipyrrolmethane, step (c) of reacting the 4-(3-bromopropyloxy)benzaldehyde with the dipyrrol-methane, together with trifluoro acetic acid, in the presence of an oxidation reagent to produce 5,15-bis-[4-(3-bromo-propyloxy)-phenyl]-porphyrin which is purified by Soxhlet extraction from the adsorbed state on a bed of alumina under highly controlled conditions; and step (d) of reacting the 5,15-bis-[4-(3-bromo-propyloxy)-phenyl]-porphyrin with trimethylamine in the presence of dry dimethylformamide to produce 5,15-bis-[4-(3-trimethylammonio-propyl-oxy)-phenyl]-porphyrin dibromide. In a preferred embodiment, the process further comprises step (e) of passing the 5,15-bis-[4-(3-trimethylammonio-propyloxy)-phenyl]-porphyrin dibromide produced in step (d) through an anion exchanger to produce 5,15-bis-[4-(3-trimethylammonio-propyloxy)-phenyl]-porphyrin dichloride. There is provided a process for the preparation of 5,15-bis-(4-{3-[(3-dimethylamino-propyl)-dimethyl-ammonio]-propyloxy}-phenyl]-porphyrin dihalide.