Preparation of metal mesoporphyrin halide compounds
AssigneeWellSpring Pharmaceutical Corporation
InventorsRobert A. Vukovich, Benjamin Levinson, George S. Drummond, Robert Caroselli, Kazimierz G. Antczak, Christopher Boucher, Richard Mortimer
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Abstract
A method of preparing metal mesoporphyrin halide compounds is described. The metal mesoporphyrin halide compound may be formed by forming a novel mesoporphyrin IX intermediate compound and then converting the mesoporphyrin IX intermediate to the metal mesoporphyrin halide through metal insertion. The novel intermediate compound may be formed by a catalytic hydrogenation of hemin in acid and subsequent recovery.
Claims11
A process of preparing a formate salt of mesoporphyrin IX, which comprises:
- a) subjecting a reaction mixture of hemin and a hydrogenation catalyst in an acid to hydrogen pressure of about 30-60 psi and then raising the temperature to about 85-95 C. and maintaining the temperature within that range for a period of about 1-3 hours;
- b) subjecting the reaction mixture to a further hydrogen pressure of about 30-60 psi at a temperature range of about 45-50 C. for a period of about 3-6 hours;
- and
- c) recovering the formate salt of mesoporphyrin IX from the reaction mixture by precipitation of the mixture with a solvent.
A formate salt of mesoporphyrin IX.
A process of converting a formate salt of mesoporphyrin IX to a metal mesoporphyrin halide, which comprises:
- a) drying the formate salt of mesoporphyrin IX to obtain a mesoporphyrin IX formate;
- b) subjecting the mesoporphyrin IX formate to a chemical metal insertion process reaction with a metal halide compound in the presence of an oxidant under buffered, acidic reaction conditions;
- and
- c) recovering the metal mesoporphyrin halide from the reaction mixture.
A process of purifying a metal mesoporphyrin halide, which comprises:
- a) dissolving the metal mesoporphyrin halide in an aqueous basic solution to obtain a dissolved metal mesoporphyrin halide;
- b) treating said dissolved metal mesoporphyrin halide with charcoal to obtain a treated metal mesoporphyrin halide;
- c) adding said treated metal mesoporphyrin halide to a first aqueous acid solution to obtain a precipitated metal mesoporphyrin halide;
- d) triturating said precipitated metal mesoporphyrin halide in a second aqueous acid solution at elevated temperature to obtain a substantially pure metal mesoporphyrin halide;
- and
- e) drying said substantially pure metal mesoporphyrin halide.
Dependencies are inferred from the claim text.