Claims for Patent: 6,939,964

Summary for Patent: 6,939,964

Title:	Crystal forms of (-)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-ben zoxazin-2-one
Abstract:	The instant invention describes a method for crystallizing (-)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-ben zoxazin-2-one from a solvent and anti-solvent solvent system and producing the crystalline product. The desired final crystal form, Form I, can be produced when using methanol or ethanol. Form II is isolated from 2-propanol and can be converted to the desired crystal form at low drying temperatures, such as between about a temperature of 40.degree. C. and 50.degree. C.
Inventor(s):	Crocker; Louis S. (Belle Mead, NJ), Kukura, II; Joseph L. (Somerset, NJ), Thompson; Andrew S. (Mountainside, NJ), Stelmach; Christine (Westfield, NJ), Young; Steven D. (Lansdale, PA)
Assignee:	Merck & Co., Inc. (Rahway, NJ)
Application Number:	10/891,749
Patent Litigation and PTAB cases:	See patent lawsuits and PTAB cases for patent 6,939,964
Patent Claims:	1. Form I of (-)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-ben zoxazin-2-one, which is characterized by crystallographic D-spacings of 14.5, 8.5 and 7.2 Angstroms. 2. Form I according to claim 1, characterized by crystallographic D-spacings of 14.5, 8.5, 7.2, 6.2, 4.4 and 4.2 Angstroms. 3. Form I according to claim 2, characterized by crystallographic D-spacings of 14.5, 8.5, 8.0, 7.2, 6.7, 6.2, 4.4 and 4.2 Angstroms. 4. Form I according to claim 1, having no detectable peaks for Form II or Form III in its X-ray powder diffraction pattern. 5. Form II of (-)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-ben zoxazin-2-one, characterized by crystallographic D-spacings of 24.3, 6.9 and 5.5 Angstroms. 6. Form II according to claim 5, characterized by crystallographic D-spacings of 24.3, 13.9, 6.9, 6.6, 5.5 and 4.3 Angstroms. 7. Form II according to claim 6, characterized by crystallographic D-spacings of 24.3, 13.9, 8.0, 6.9, 6.6, 5.5, 4.5, 4.3, and 3.6 Angstroms. 8. Form II according to claim 5, having no detectable peaks for Form I or Form III in its X-ray powder diffraction pattern. 9. Form III of (-)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-ben zoxazin-2-one, characterized by crystallographic D-spacings of 12.2, 6.1 and 4.3 Angstroms. 10. Form III according to claim 9, characterized by crystallographic D-spacings of 12.2, 8.1, 6.1, 4.7, 4.3 and 4.1 Angstroms. 11. Form III according to claim 10, characterized by crystallographic D-spacings of 12.2, 8.1, 6.4, 6.1, 4.7, 4.3, 4.1, 3.7 and 3.6 Angstroms. 12. Form III according to claim 9, having no detectable peaks for Form I or Form II in its X-ray powder diffraction pattern. 13. Form III according to claim 9, which is further characterized by a DSC curve with a peak temperature of about 118.degree. C. and an enthalpy of 34 J/g. 14. Form III according to claim 13, which is further characterized by a thermogravimetric analysis indicating no significant weight loss from 43.degree. C. to 137.degree. C.