Claims for Patent: 6,639,071

Summary for Patent: 6,639,071

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 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:	10/000,537
Patent Litigation and PTAB cases:	See patent lawsuits and PTAB cases for patent 6,639,071
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 an X-ray powder diffraction pattern as exhibited in FIG. 3. 2. Form II of (-)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-ben zoxazin-2-one which is characterized by an X-ray powder diffraction pattern as exhibited in FIG. 4. 3. Form III of (-)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-ben zoxazin-2-one which is characterized by an X-ray powder diffraction pattern as exhibited in FIG. 5. 4. Form III of (-)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-ben zoxazin-2-one as recited in claim 3, which is further characterized by a DSC curve as exhibited in FIG. 6. 5. Form III of (-)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-ben zoxazin-2-one as recited in claim 4, which is further characterized by a TG analysis as exhibited in FIG. 7. 6. Form I of (-)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-ben zoxazin-2-one characterized by crystallographic D-spacings of 14.5, 8.5, 8.0, 7.2, 6.7, 6.2, 5.2, 4.6, 4.4, 4.2 and 3.6 Angstroms. 7. Form I according to claim 6, having no detectable peaks for Form II or Form III in its X-ray powder diffraction pattern. 8. 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, 13.9, 8.0, 6.9, 6.6, 5.5, 4.6, 4.5, 4.3, 4.2, 3.9, 3.6, 3.4, 3.3 and 3.2 Angstroms. 9. Form II according to claim 8, having no detectable peaks for Form I or Form III in its X-ray powder diffraction pattern. 10. Form III of (-)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-ben zoxazin-2-characterized by crystallographic D-spacings of 12.2, 8.1, 6.4, 6.1, 4.7, 4.3, 4.1, 4.0, 3.9, 3.8, 3.7, 3.6, 3.3, 3.2 and 3.0 Angstroms. 11. Form III according to claim 10, having no detectable peaks for Form I or Form II in its X-ray powder diffraction pattern.