CRYSTALLINE FORM OF y-AMINOBUTYRIC ACID ANALOG

Abstract

A crystalline form of a γ-aminobutyric acid analog, and methods of preparing same, are provided.

1 - 28 . (canceled) 
     
     
         29 . 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, restless legs syndrome, urinary incontinence and ethanol withdrawal syndrome in a patient in need of such treatment, comprising administering to the patient a therapeutically effective amount of crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid. 
     
     
         30 . The method of  claim 29 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has characteristic absorption peaks at 7.0°±0.3°, 8.2°±0.3°, 10.5°±0.3°, 12.8°±0.3°, 14.9°±0.3° and 16.4°±0.3° in an X-ray powder diffractogram using Cu Kα radiation. 
     
     
         31 . The method of  claim 30 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has a characteristic absorption peak at 17.9°±0.3° in the X-ray powder diffractogram using Cu Kα radiation. 
     
     
         32 . The method of  claim 30 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has a characteristic absorption peak at 18.1°±0.3° in the X-ray powder diffractogram using Cu Kα radiation. 
     
     
         33 . The method of  claim 30 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has a characteristic absorption peak at 18.9°±0.3° in the X-ray powder diffractogram using Cu Kα radiation. 
     
     
         34 . The method of  claim 30 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has a characteristic absorption peak at 20.9°±0.3° in the X-ray powder diffractogram using Cu Kα radiation. 
     
     
         35 . The method of  claim 30 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has a characteristic absorption peak at 23.3°±0.3° in the X-ray powder diffractogram using Cu Kα radiation. 
     
     
         36 . The method of  claim 30 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has a characteristic absorption peak at 25.3°±0.3° in the X-ray powder diffractogram using Cu Kα radiation. 
     
     
         37 . The method of  claim 30 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has a characteristic absorption peak at 26.6°±0.3° in the X-ray powder diffractogram using Cu Kα radiation. 
     
     
         38 . The method of  claim 30 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has characteristic absorption peaks at 17.9°±0.3°, 18.9°±0.3°, 20.9°±0.3°, 23.3°±0.3°, 25.3°±0.3°, and 26.6°±0.3° in the X-ray powder diffractogram using Cu Kα radiation. 
     
     
         39 . The method of  claim 30 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has characteristic absorption peaks at 18.1°±0.3°, 18.9°±0.3°, 20.9°±0.3°, 23.3°±0.3°, 25.3°±0.3°, and 26.6°±0.3° in the X-ray powder diffractogram using Cu Kα radiation. 
     
     
         40 . The method of  claim 30 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has characteristic absorption peaks at 17.9°±0.3°, 18.1°±0.3°, 18.9°±0.3°, 20.9°±0.3°, 23.3°±0.3°, 25.3°±0.3°, and 26.6°±0.3° in the X-ray powder diffractogram using Cu Kα radiation. 
     
     
         41 . The method of  claim 29 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has a melting point range of between 63° C. and 64° C. as determined by differential scanning calorimetry at a scan rate of 5° C./minute. 
     
     
         42 . The method of  claim 29 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has a melting point range of between 64° C. and 66° C. as determined by open capillary melting point determination. 
     
     
         43 . The method of  claim 30 , wherein the disease or disorder is epilepsy. 
     
     
         44 . The method of  claim 30 , wherein the disease or disorder is pain. 
     
     
         45 . The method of  claim 44 , wherein the pain is neuropathic pain, muscular pain or skeletal pain. 
     
     
         46 . The method of  claim 45 , wherein the pain is neuropathic pain. 
     
     
         47 . The method of  claim 44 , wherein the pain is post herpetic neuralgia. 
     
     
         48 . The method of  claim 30 , wherein the disease or disorder is anxiety. 
     
     
         49 . The method of  claim 30 , wherein the disease or disorder is hot flashes. 
     
     
         50 . The method of  claim 30 , wherein the disease or disorder is restless legs syndrome. 
     
     
         51 . The method of  claim 30 , wherein the disease or disorder is ethanol withdrawal syndrome. 
     
     
         52 . The method of  claim 30 , wherein the disease or disorder is inflammatory disease. 
     
     
         53 . The method of  claim 30 , wherein the disease or disorder is a gastrointestinal disorder. 
     
     
         54 . 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, restless legs syndrome, urinary incontinence, and ethanol withdrawal syndrome in a patient in need of such treatment, comprising administering to the patient a pharmaceutical composition comprising a therapeutically effective amount of crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid and a pharmaceutically acceptable vehicle. 
     
     
         55 . The method of  claim 54 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has characteristic absorption peaks at 7.0°±0.3°, 8.2°±0.3°, 10.5°±0.3°, 12.8°±0.3°, 14.9°±0.3° and 16.4°±0.3° in an X-ray powder diffractogram using Cu Kα radiation. 
     
     
         56 . The method of  claim 55 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has a characteristic absorption peak at 17.9°±0.3° in the X-ray powder diffractogram using Cu Kα radiation. 
     
     
         57 . The method of  claim 55 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has a characteristic absorption peak at 18.1°±0.3° in the X-ray powder diffractogram using Cu Kα radiation. 
     
     
         58 . The method of  claim 55 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has a characteristic absorption peak at 18.9°±0.3° in the X-ray powder diffractogram using Cu Kα radiation. 
     
     
         59 . The method of  claim 55 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has a characteristic absorption peak at 20.9°±0.3° in the X-ray powder diffractogram using Cu Kα radiation. 
     
     
         60 . The method of  claim 55 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has a characteristic absorption peak at 23.3°±0.3° in the X-ray powder diffractogram using Cu Kα radiation. 
     
     
         61 . The method of  claim 55 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has a characteristic absorption peak at 25.3°±0.3° in the X-ray powder diffractogram using Cu Kα radiation. 
     
     
         62 . The method of  claim 55 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has a characteristic absorption peak at 26.6°±0.3° in the X-ray powder diffractogram using Cu Kα radiation. 
     
     
         63 . The method of  claim 55 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has characteristic absorption peaks at 17.9°±0.3°, 18.90±0.3°, 20.9°±0.3°, 23.3°±0.3°, 25.3°±0.3°, and 26.6°±0.3° in the X-ray powder diffractogram using Cu Kα radiation. 
     
     
         64 . The method of  claim 55 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has characteristic absorption peaks at 18.1°±0.3°, 18.9°±0.3°, 20.9°±0.3°, 23.3°±0.3°, 25.3°±0.3°, and 26.6°±0.3° in the X-ray powder diffractogram using Cu Kα radiation. 
     
     
         65 . The method of  claim 55 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has characteristic absorption peaks at 17.9°±0.3°, 18.1°±0.3°, 18.9°±0.3°, 20.9°±0.3°, 23.3°±0.3°, 25.3°±0.3°, and 26.6°±0.3° in the X-ray powder diffractogram using Cu Kα radiation. 
     
     
         66 . The method of  claim 54 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has a melting point range of between 63° C. and 64° C. as determined by differential scanning calorimetry at a scan rate of 5° C./minute. 
     
     
         67 . The method of  claim 54 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has a melting point range of between 64° C. and 66° C. as determined by open capillary melting point determination. 
     
     
         68 . The method of  claim 55 , wherein the disease or disorder is epilepsy. 
     
     
         69 . The method of  claim 68 , wherein the pharmaceutical composition is an oral sustained release system. 
     
     
         70 . The method of  claim 55 , wherein the disease or disorder is pain. 
     
     
         71 . The method of  claim 70 , wherein the pain is neuropathic pain, muscular pain or skeletal pain. 
     
     
         72 . The method of  claim 71 , wherein the pain is neuropathic pain. 
     
     
         73 . The method of  claim 72 , wherein the pharmaceutical composition is an oral sustained release system. 
     
     
         74 . The method of  claim 70 , wherein the pain is post herpetic neuralgia. 
     
     
         75 . The method of  claim 74 , wherein the pharmaceutical composition is an oral sustained release system. 
     
     
         76 . The method of  claim 55 , wherein the disease or disorder is anxiety. 
     
     
         77 . The method of  claim 76 , wherein the pharmaceutical composition is an oral sustained release system. 
     
     
         78 . The method of  claim 55 , wherein the disease or disorder is hot flashes. 
     
     
         79 . The method of  claim 78 , wherein the pharmaceutical composition is an oral sustained release system. 
     
     
         80 . The method of  claim 55 , wherein the disease or disorder is restless legs syndrome. 
     
     
         81 . The method of  claim 80 , wherein the pharmaceutical composition is an oral sustained release system. 
     
     
         82 . The method of  claim 55 , wherein the disease or disorder is ethanol withdrawal syndrome. 
     
     
         83 . The method of  claim 82 , wherein the pharmaceutical composition is an oral sustained release system. 
     
     
         84 . The method of  claim 55 , wherein the disease or disorder is inflammatory disease, 
     
     
         85 . The method of  claim 84 , wherein the pharmaceutical composition is an oral sustained release system. 
     
     
         86 . The method of  claim 55 , wherein the disease or disorder is a gastrointestinal disorder. 
     
     
         87 . The method of  claim 86 , wherein the pharmaceutical composition is an oral sustained release system.