US 7,365,224 B2
Pharmaceutical compositions of isolated orthorhombic crystalline 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy]butyric acid and methods of use
Kenneth Walter Locke, Carlsbad, Calif. (US); and David Gregory Roe, Rockwood (Canada)
Assigned to Medicinova, Inc., San Diego, Calif. (US)
Filed on Dec. 29, 2005, as Appl. No. 11/319,272.
Application 11/319272 is a continuation of application No. 10/601862, filed on Jun. 24, 2003, granted, now 7,064,146.
Prior Publication US 2006/0135604 A1, Jun. 22, 2006
This patent is subject to a terminal disclaimer.
Int. Cl. C07C 321/00 (2006.01); A61K 31/19 (2006.01); A61K 31/235 (2006.01)
U.S. Cl. 562—431  [514/545; 514/571] 12 Claims
OG exemplary drawing
 
1. Isolated orthorhombic crystalline 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propyl- phenoxy]butyric acid, prepared by the method of: dissolving 4-[6-acetyl-3-[3 -(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propyl-phenoxy]butyric acid in ethanol, adding water and cooling the resulting mixture first to about 10-15° C. and second to about 5-10° C., adding more water, agitating the resulting mixture at about 5-10° C., and isolating the orthorhombic crystals of 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propyl-phenoxy]butyric acid,
wherein the isolated orthorhombic crystals of 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propyl-phenoxy]butyric acid are substantially free of monoclinic crystalline forms as evidenced by powder x-ray diffraction analysis showing the absence of doublet peaks between about 11.5 and 16 (2-Theta scale).