Details for Patent: 9,150,503

Title:	Crystalline form of .gamma.-aminobutyric acid analog
Abstract:	A crystalline form of a .gamma.-aminobutyric acid analog, and methods of preparing same, are provided.
Inventor(s):	Estrada; Tono (Santa Clara, CA), Raillard; Stephen P. (Mountain View, CA), Frauenfelder; Christine (Glis, CH), Zacher; Uwe (Brig, CH)
Assignee:	XenoPort, Inc. (Santa Clara, CA)
Filing Date:	Mar 12, 2014
Application Number:	14/206,893
Claims:	1. A method of treating a disease or disorder selected from epilepsy, pain, depression, anxiety, psychosis, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, panic, inflammatory disease, insomnia, gastrointestinal disorders, hot flashes, and ethanol withdrawal syndrome in a patient in need of such treatment, comprising administering to the patient a therapeutically effective amount of crystalline 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid having characteristic absorption peaks at 7.0.degree..+-.0.3.degree., 8.2.degree..+-.0.3.degree., 10.5.degree..+-.0.3.degree., 12.8.degree..+-.0.3.degree., 14.9.degree..+-.0.3.degree., and 16.4.degree..+-.0.3.degree. in an X-ray powder diffractogram using Cu K.alpha. radiation. 2. The method of claim 1, wherein the crystalline 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has a characteristic absorption peak at 17.9.degree..+-.0.3.degree. in the X-ray powder diffractogram using Cu K.alpha. radiation. 3. The method of claim 1, wherein the crystalline 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has a characteristic absorption peak at 18.1.degree..+-.0.3.degree. in the X-ray powder diffractogram using Cu K.alpha. radiation. 4. The method of claim 1, wherein the crystalline 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has a characteristic absorption peak at 18.9.degree..+-.0.3.degree. in the X-ray powder diffractogram using Cu K.alpha. radiation. 5. The method of claim 1, wherein the crystalline 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has a characteristic absorption peak at 20.9.degree..+-.0.3.degree. in the X-ray powder diffractogram using Cu K.alpha. radiation. 6. The method of claim 1, wherein the crystalline 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has a characteristic absorption peak at 23.3.degree..+-.0.3.degree. in the X-ray powder diffractogram using Cu K.alpha. radiation. 7. The method of claim 1, wherein the crystalline 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has a characteristic absorption peak at 25.3.degree..+-.0.3.degree. in the X-ray powder diffractogram using Cu K.alpha. radiation. 8. The method of claim 1, wherein the crystalline 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has a characteristic absorption peak at 26.6.degree..+-.0.3.degree. in the X-ray powder diffractogram using Cu K.alpha. radiation. 9. The method of claim 1, wherein the crystalline 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has characteristic absorption peaks at 17.9.degree..+-.0.3.degree., 18.9.degree..+-.0.3.degree., 20.9.degree..+-.0.3.degree., 23.3.degree..+-.0.3.degree., 25.3.degree..+-.0.3.degree., and 26.6.degree..+-.0.3.degree. in the X-ray powder diffractogram using Cu K.alpha. radiation. 10. The method of claim 1, wherein the crystalline 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has characteristic absorption peaks at 18.1.degree..+-.0.3.degree., 18.9.degree..+-.0.3.degree., 20.9.degree..+-.0.3.degree., 23.3.degree..+-.0.3.degree., 25.3.degree..+-.0.3.degree., and 26.6.degree..+-.0.3.degree. in the X-ray powder diffractogram using Cu K.alpha. radiation. 11. The method of claim 1, wherein the crystalline 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has characteristic absorption peaks at 17.9.degree..+-.0.3.degree., 18.1.degree..+-.0.3.degree., 18.9.degree..+-.0.3.degree., 20.9.degree..+-.0.3.degree., 23.3.degree..+-.0.3.degree., 25.3 .degree..+-.0.3.degree., and 26.6.degree..+-.0.3.degree. in the X-ray powder diffractogram using Cu K.alpha. radiation. 12. The method of claim 1, wherein the crystalline 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has a melting point range of between 63.degree. C. and 64.degree. C. as determined by differential scanning calorimetry at a scan rate of 5.degree. C./minute. 13. The method of claim 1, wherein the method treats pain. 14. The method of claim 13, wherein the method treats neuropathic pain, muscular pain or skeletal pain. 15. The method of claim 14, wherein the method treats neuropathic pain. 16. The method of claim 1, wherein the disease or disorder is hot flashes. 17. The method of claim 1, wherein the disease or disorder is ethanol withdrawal syndrome. 18. The method of claim 1, wherein the crystalline 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid is administered as a pharmaceutical composition comprising a therapeutically effective amount of the crystalline 1-{[(.alpha.-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid and a pharmaceutically acceptable vehicle. 19. The method of claim 18, wherein the pharmaceutical composition is an oral sustained release system.