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Last Updated: March 28, 2024

Claims for Patent: 7,777,028


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Summary for Patent: 7,777,028
Title:Preparation of metal mesoporphyrin compounds
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.
Inventor(s): Vukovich; Robert A. (Holmdel, NJ), Levinson; Benjamin (Montgomery, NJ), Drummond; George S. (New York, NY), Caroselli; Robert (East Brunswick, NJ), Antczak; Kazimierz G. (Culver, IN), Boucher; Christopher P. (Newmarket, CA), Mortimer; Richard (Toronto, CA), Levin; Daniel (Toronto, CA), Cooke; Keith A. (Milton, CA)
Assignee: Infacare Pharmaceutical Corporation (Trevose, PA)
Application Number:11/957,317
Patent Claims:1. A process of preparing mesoporphyrin IX formate comprising the steps of: (a) subjecting a mixture of hemin and a hydrogenation catalyst in formic acid to hydrogen at a temperature of 85-95.degree. C. and (b) followed by subsequently subjecting said mixture to hydrogen at a temperature of from 45-50.degree. C., to produce mesoporphyrin IX formate, having the following formula: ##STR00001##

2. The process of claim 1, wherein the hydrogen of step (a) is at a pressure of about 30-60 psi.

3. The process of claim 1, wherein the hydrogen of step (b) is at a pressure of 30-60 psi.

4. The process of claim 1, wherein step (a) endures for about 1-3 hours.

5. The process of claim 4, wherein step (a) endures for about 1 hour.

6. The process of claim 1, wherein the hydrogen of step (a) is at a temperature of about 90.degree. C.

7. The process of claim 1, wherein step (b) endures for about 3-6 hours.

8. The process of claim 1, wherein said hydrogenation catalyst is selected from the group consisting of palladium, platinum, nickel, and palladium on carbon.

9. The process of claim 1, further comprising minimizing the exposure of the reaction to visible or ultraviolet light.

10. The process of claim 1, further comprising: (c) recovering the mesoporphyrin IX formate.

11. The process of claim 10, wherein said recovering is by the addition of ethers.

12. The process of claim 1, further comprising: (c) dissolving the formate in formic acid and using a metal scavenger to purify the formate by removing residual metal catalysts.

13. The process of claim 12, wherein said metal scavenger is selected from the group consisting of: Si-thiol, Si-thiourea, Si-triamine, and Si-triaminetetraacetatic acid.

14. The process of claim 11, wherein the ether is selected from the group consisting of: methyl tert-butyl ether, diethyl ether, and di-isopropyl ether.

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