Crystalline forms of a prolyl hydroxylase inhibitor

Abstract

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.

What is claimed is: 
     
         1 . A process for preparing crystalline [(4-hydroxy-1-methyl-7-phenoxy-isoquinoline-3-carbonyl)-amino]-acetic acid (Compound A), comprising contacting Compound A, or a salt thereof, with acetic acid for a time sufficient to provide a crystalline Compound A wherein at least about 95% of the crystalline Compound A is Form A. 
     
     
         2 . The process of  claim 1 , wherein the process further comprises, following said contacting step, isolating the crystalline Compound A Form A. 
     
     
         3 . The process of  claim 2 , wherein the isolating comprises the steps of filtering, washing and drying the crystalline Compound A Form A. 
     
     
         4 . The process of  claim 1 , wherein the contacting comprises adding the acetic acid to Compound A at a temperature of from about 10° C. to about 90° C. 
     
     
         5 . The process of  claim 4 , wherein the acetic acid is added to the Compound A as an aqueous solution, slowly with stirring. 
     
     
         6 . The process of  claim 1 , wherein prior to contacting Compound A with the acetic acid, an aqueous solution of sodium hydroxide is added slowly to a stirred suspension of Compound A in water at temperature of from about 10° C. to about 90° C. 
     
     
         7 . The process 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. 
     
     
         8 . The process of  claim 7 , wherein the DSC curve is substantially as shown in  FIG. 2 . 
     
     
         9 . The process of  claim 1 , wherein the Compound A Form A is characterized by an X-ray powder diffractogram comprising a peak at 8.5°2θ±0.2°2θ. 
     
     
         10 . The process of  claim 1 , wherein the Compound A Form A is characterized by an X-ray powder diffractogram comprising a peak at 16.2°2θ±0.2°2θ. 
     
     
         11 . The process of  claim 1 , wherein the Compound A Form A is characterized by an X-ray powder diffractogram comprising a peak at 27.4°2θ±0.2°2θ. 
     
     
         12 . The process of  claim 1 , wherein the Compound A Form A is characterized by an X-ray powder diffractogram comprising peaks at 8.5, 16.2, and 27.4°2θ±0.2°2θ. 
     
     
         13 . The process of  claim 12 , wherein the X-ray powder diffractogram further comprises peaks at 12.8, 21.6, and 22.9°2θ±0.2°2θ. 
     
     
         14 . The process of  claim 1 , wherein the Compound A Form A is characterized by an X-ray powder diffractogram substantially as shown in  FIG. 1 . 
     
     
         15 . The process of  claim 1 , wherein at least about 99% of the crystalline Compound A produced by the process is Compound A Form A. 
     
     
         16 . The process of  claim 1 , wherein at least about 99.5% of the crystalline Compound A produced by the process is Compound A Form A. 
     
     
         17 . The process of  claim 1 , wherein at least about 99.9% of the crystalline Compound A produced by the process is Compound A Form A. 
     
     
         18 . The process of  claim 1 , wherein at least about 99.99% of the crystalline Compound A produced by the process is Compound A Form A.