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Last Updated: April 23, 2024

Claims for Patent: 8,178,664


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Summary for Patent: 8,178,664
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 (Holmdel, NJ), Levinson; Benjamin (Montgomery, NJ), Drummond; George S. (New York, NY), Caroselli; Robert (East Brunswick, NJ), Antczak; Kazimierz G. (Culver, IN), Boucher; Christopher (Newmarket, CA), Mortimer; Richard (Toronto, CA), Levin; Danny (Toronto, CA), Cooke; Keith A. (Milton, CA)
Assignee: Infacare Pharmaceutical Corporation (Trevose, PA)
Application Number:12/833,873
Patent Claims:1. A method of making mesoporphyrin IX formate, the method comprising: subjecting a mixture of hemin and a hydrogenation catalyst in formic acid to a first temperature and a first pressure for a first period of time; and subjecting the mixture to a second temperature and a second pressure for a second period of time to form the mesoporphyrin IX formate.

2. The method of claim 1, wherein the mesoporphyrin IX formate has a purity of at least about 97%.

3. The method of claim 1, further comprising isolating the mesoporphyrin IX formate from the mixture.

4. The method of claim 3, wherein isolating the mesoporphyrin IX formate from the mixture is by using an organic solvent.

5. The method of claim 4, wherein the organic solvent is selected from ether, methyl tert-butyl ether, diethyl ether, di-isopropyl ether, or a combination thereof.

6. The method of claim 4, wherein a ratio of an amount of hemin to an amount of organic solvent is about 1:10 to about 1:20.

7. The method of claim 1, further comprising purifying the mesoporphyrin IX formate.

8. The method of claim 7, wherein purifying the mesoporphyrin IX formate is by using a metal scavenger.

9. The method of claim 8, wherein the metal scavenger is selected from Si-thiol, Si-thiourea, Si-triamine, Si-triaminetetraacetatic acid, or a combination thereof.

10. The method of claim 7, wherein purifying the mesoporphyrin IX formate is for a period of time of about 10 to about 20 hours.

11. The method of claim 8, further comprising removing the metal scavenger.

12. The method of claim 1, wherein the first pressure is about 30 to about 60 psi.

13. The method of claim 1, wherein the first temperature is about 85.degree. C. to about 95.degree. C.

14. The method of claim 1, wherein the first period of time is from about 1 to about 3 hours.

15. The method of claim 1, wherein the second pressure is about 30 to about 60 psi.

16. The method of claim 1, wherein the second temperature is about 45.degree. C. to about 50.degree. C.

17. The method of claim 1, wherein the second period of time is from about 3 to about 6 hours.

18. The method of claim 1, further comprising filtering the mixture to make a filtrate.

19. The method of claim 18, further comprising concentrating the filtrate.

20. An isolated mesoporphyrin IX formate comprising the formula: ##STR00001##

21. A method of making mesoporphyrin IX formate, the method comprising: dissolving mesoporphyrin IX in formic acid to make a formic acid solution; and adding an organic solvent to the formic acid solution to isolate a mesoporphyrin IX formate.

22. The method of claim 21, wherein the organic solvent comprises ether, methyl tert-butyl ether, diethyl ether, di-isopropyl ether, or a combination thereof.

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