Meso-monoiodo-substituted tetramacrocyclic compounds and methods for making and using the same

US5703230A · kind A · utility

Assignee

• University of British Columbia · CA

Inventors

• Ross W. Boyle · Vancouver, CA
• David Dolphin · Vancouver, CA
• Claire K. Johnson · Munich, DE

Key dates

• Filing date: Dec 2, 1994
• Grant date: Dec 30, 1997
• Expiry date: Dec 2, 2014

Classification

• Technology area (CPC A): Human Necessities
• CPC primary: A61P35/00
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

A meso-monoiodo-substituted tetramacrocyclic compound having the formula (I): ##STR1## wherein: each of A through D is independently a 5-membered, nitrogen-containing ring having the members necessary to complete a porphyrin, chlorin, bacteriochlorin or isobacteriochlorin nucleus; PA1 R.sub.1 through R.sub.8 are independently a hydrogen atom, a lower alkyl group, a lower alkyl carboxylic acid or acid ester group, keto, hydroxy, nitro, amino, or a group that, taken together with another ring, ring substituent or meso-substituent, forms a fused 5- or 6-membered ring; and PA1 each of S.sup.1 through S.sup.3 is H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heterocyclic ring. A method for synthesizing the compound comprises the step of iodinating a corresponding unhalogenated, de-metallated tetramacrocyclic compound, followed by metallating. The compound of the invention is an intermediate capable of coupling with an alkyne to achieve a desired mono-meso-alkynyl compound.