Preparation of metal mesoporphyrin compounds
View Patent ↗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.
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° C. to about 95° 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° C. to about 50° 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:
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.