Granted Patent B2

US 8,686,034 · App. 13/164,620 · Granted Apr 1, 2014

Abstract

Claims (32)

1. A method of treating restless legs syndrome or post herpetic neuralgia 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,

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.

2. The method of claim 1 , 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.

3. The method of claim 1 , 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.

4. The method of claim 1 , 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.

5. The method of claim 1 , 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.

6. The method of claim 1 , 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.

7. The method of claim 1 , 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.

8. The method of claim 1 , 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.

9. The method of claim 1 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has characteristic absorption peaks at 17.9°±0.30, 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.

10. The method of claim 1 , 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.

11. The method of claim 1 , 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.

12. The method of claim 1 , 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.

13. The method of claim 1 , wherein the method treats post herpetic neuralgia.

14. The method of claim 1 , wherein the method treats restless legs syndrome.

15. A method of treating restless legs syndrome or post herpetic neuralgia 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,

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.

16. The method of claim 15 , wherein the crystalline 1-{[(α-isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-cyclohexane acetic acid has a characteristic absorption peak at 7.9°±0.3° in the X-ray powder diffractogram using Cu Kα radiation.

17. The method of claim 15 , 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.

18. The method of claim 15 , 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.

19. The method of claim 15 , 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.

20. The method of claim, 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.

21. The method of claim 15 , 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.

22. The method of claim 15 , 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.

23. The method of claim 15 , 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.

24. The method of claim 15 , 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.

25. The method of claim 15 , 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.

26. The method of claim 15 , 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.

27. The method of claim 15 , wherein the method treats post herpetic neuralgia.

28. The method of claim 27 , wherein the pharmaceutical composition is an oral sustained release system.

29. The method of claim 15 , wherein the method treats restless legs syndrome.

30. The method of claim 29 , wherein the pharmaceutical composition is an oral sustained release system.

Assignments (8)