Crystalline forms of a prolyl hydroxylase inhibitor
The present disclosure relates to crystalline solid forms of [(4-hydroxy-1-methyl-7-phenoxy-isoquinoline-3-carbonyl)-amino]-acetic acid, the process of preparing the forms, and pharmaceutical compositions and methods of use thereof.
1. A method for treating, pretreating, or delaying onset or progression of a condition mediated at least in part by hypoxia inducible factor (HIF), comprising administering to a patient in need thereof, a therapeutically effective amount of crystalline [(4-hydroxy-1-methyl-7-phenoxy-isoquinoline-3-carbonyl)-amino]-acetic acid (Compound A Form A) characterized by an X-ray powder diffractogram comprising the following peaks: 8.5, 16.2, and 27.4°2θ±0.2°2θ.
2. The method of claim 1 , wherein the diffractogram further comprises peaks at 12.8, 21.6, and 22.9°2θ±0.2°2θ.
3. The method of claim 1 , wherein the diffractogram is substantially as shown in FIG. 1 .
4. The method of claim 1 , wherein the Compound A Form A is characterized by a differential scanning calorimetry (DSC) curve that comprises an endotherm at about 223° C.
5. The method of claim 4 , wherein the DSC curve is substantially as shown in FIG. 2 .
6. The method of claim 1 , wherein the condition mediated at least in part by HIF is tissue damage associated with ischemia or hypoxia.
7. The method of claim 6 , wherein the ischemia is associated with an acute event selected from the group consisting of myocardial infarction, pulmonary embolism, intestinal infarction, chronic kidney failure, ischemic stroke, and renal ischemic-reperfusion injury.
8. The method of claim 6 , wherein the ischemia is associated with a chronic event selected from the group consisting of cardiac cirrhosis, transient ischemic attack, macular degeneration, peripheral artery disease, and congestive heart failure.
9. A method for treating, pretreating, or delaying onset or progression of a condition mediated at least in part by erythropoietin (EPO), comprising administering to a patient in need thereof, a therapeutically effective amount of crystalline [(4-hydroxy-1-methyl-7-phenoxy-isoquinoline-3-carbonyl)-amino]-acetic acid (Compound A Form A) characterized by an X-ray powder diffractogram comprising the following peaks: 8.5, 16.2, and 27.4°2θ±0.2°2θ.
10. The method of claim 9 , wherein the diffractogram further comprises peaks at 12.8, 21.6, and 22.9°2θ±0.2°2θ.
11. The method of claim 9 , wherein the diffractogram is substantially as shown in FIG. 1 .
12. The method of claim 9 , wherein the Compound A Form A is characterized by a differential scanning calorimetry (DSC) curve that comprises an endotherm at about 223° C.
13. The method of claim 12 , wherein the DSC curve is substantially as shown in FIG. 2 .