Atropisomers of halogenated tetraphenylbacteriochlorins and chlorins and their use in photodynamic therapy

Abstract

This invention relates to atroipsomers of reduced tetraphenylporphyrin derivatives with halogen atoms (F, Cl, Br) in the ortho positions of the phenyl groups, particularly halogenated tetraphenylchlorins and halogenated tetraphenylbacteriochlorins, which can be used in photodynamic therapy. According to the formulae of the invention, the ortho-phenyl substituents X, X, X, X, X, X, Xand Xmay be identical or different and represent halogen atoms or hydrogen atoms, provided that at least all of X, X, Xand Xare halogens, and the meta-phenyl substituents R, R, Rand Rare independently chosen from —OH, —OR or —SOR″, where R″ are each independently chosen from —Cl, —OH, -aminoacid, —OR, —NHR, or —NR, where R are alkyl of 1 to 12 carbon atoms or Rrepresents cycloalkyl with 2 to 12 carbon atoms. The atropisomers of this invention have the majority of the substituents R, R, Rand Ron the same side of the plane defined by the macrocycle. The invention also relates to an anticancer and/or antimicrobial and/or antiviral pharmaceutical composition where atropisomers αand αβ are the main active ingredients, such that the mixture of atropisomers αand αβ constitutes more than 70% of the atropisomers present in the active ingredient and/or the atropisomer αconstitutes more than 20% of the atropisomers present in the pharmaceutical composition.