IP Library Granted Patent US 9,222,922
Granted Patent B2
US 9,222,922 · App. 14/330,745 · Granted Dec 29, 2015

Chromatography of metal complexes

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Quick Facts
Patent No.
US 9,222,922
App. No.
14/330,745
Granted
Dec 29, 2015
Kind
B2
Abstract

A high performance liquid chromatography method to routinely and reproducibly detect and quantitate metal complexes is provided. The metal complexes used in the method of the invention can be different metal complexes, or they can be stereoisomers of the same metal complexes. The high performance liquid chromatography method of the present invention is suitable for the separation of diastereomers of the same metal complexes. Also provided is a chiral high performance liquid chromatography method to separate enantiomers of metal complexes. Superoxide dismutase mimetic compounds are also provided.

Claims (18)

1. A high performance liquid chromatography method comprising:

loading a solution containing metal complexes onto a column, wherein the metal complexes are selected from a group consisting of catalase mimics and peroxynitrite decomposition catalysts;

eluting the metal complexes from the column with a mobile phase, said mobile phase comprising an excess of a salt of a coordinating anion in a solvent system, wherein the coordinating anion is selected from chloride anions, acetate anions, trifluoroacetate anions, and formate anions; and

detecting the metal complexes with a detector.

2. The method of claim 1 wherein the metal complexes comprise products of a reaction stream.

3. The method of claim 1 wherein the salt comprises sodium chloride, lithium chloride, potassium chloride, ammonium chloride, tetrabutylammonium chloride, potassium acetate, sodium acetate, ammonium acetate, ammonium trifluoroacetate, lithium acetate, potassium formate, sodium formate, ammonium formate, or lithium formate.

4. The method of claim 1 wherein the salt comprises sodium chloride, lithium chloride or tetrabutylammonium chloride.

5. The method of claim 1 wherein the solvent system comprises a solvent.

6. The method of claim 5 wherein the solvent comprises acetonitrile, dioxane, ethanol, methanol, isopropanol, tetrahydrofuran, or water.

7. The method of claim 1 wherein the solvent system comprises a mixture of solvents.

8. The method of claim 7 wherein the mixture of solvents comprises two or more of acetonitrile, dioxane, ethanol, methanol, isopropanol, tetrahydrofuran, and water.

9. The method of claim 8 wherein the solvents comprise acetonitrile and water.

10. The method of claim 8 wherein the solvents comprise methanol and water.

11. The method of claim 1 wherein the salt is present in the mobile phase at a concentration of between about 0.004 M to about 6 M.

12. The method of claim 8 wherein the sodium chloride is present in the mobile phase at a concentration of between about 0.1 M to about 1 M.

13. The method of claim 1 wherein the column is selected from the group consisting of a C1 modified column, a C3 modified column, a C4 modified column, an octyl (C8) modified column, an octadecyl (C18) modified column, a C18 polymer column, a phenyl column, and an amino-cyano column.

14. The method of claim 1 wherein the column comprises a chiral column.

15. The method of claim 1 wherein the detector comprises a UV detector.

Assignments (8)
LICENSE Recorded Aug 29, 2018
From: INOTEK PHARMACEUTICALS CORPORATION
To: GALERA THERAPEUTICS, LLC
Reel/Frame 046971/0691 →
BILL OF SALE Recorded Aug 29, 2018
From: ACTIVBIOTICS, INC.; METAPHORE PHARMACEUTICALS, INC.
To: KEREOS, INC.; INOTEK PHARMACEUTICALS CORPORATION
Reel/Frame 047092/0402 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 29, 2018
From: INOTEK PHARMACEUTICALS CORPORATION
To: GALERA THERAPEUTICS, LLC
Reel/Frame 046742/0880 →
CHANGE OF NAME Recorded Aug 26, 2015
From: GALERA THERAPEUTICS, LLC
To: GALERA LABS, LLC
Reel/Frame 036427/0622 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 27, 2015
From: ACTIVBIOTICS, INC.; METAPHORE PHARAMCEUTICALS, INC.
To: KEREOS, INC.; INOTEK PHARMACEUTICALS CORPORATION
Reel/Frame 035276/0439 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 27, 2015
From: INOTEK PHARMACEUTICAL CORPORATION
To: GALERA THERAPEUTICS, LLC
Reel/Frame 035276/0554 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 27, 2015
From: KEREOS, INC.
To: GALERA THERAPEUTICS, LLC
Reel/Frame 035276/0653 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 27, 2015
From: SLOMCZYNSKA, URSZULA J.; TRAWICK, BOBBY N.; RILEY, DENNIS P.; NAIK, ARATI
To: METAPHORE PHARMACEUTICALS, INC.
Reel/Frame 035276/0246 →