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Claims for Patent: 9,364,489

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Claims for Patent: 9,364,489

Title:Crystals and process of making 5-({[2-amino-3-(4-Carbamoyl-2,6-dimethyl-phenyl)-propionyl]-[1-(4-phenyl-- 1h-imidazol-2-yl)-ethyl]-amino}-methyl)-2-methoxy-benzoic acid
Abstract: The present invention relates to a novel crystals of 5-({[2-amino-3-(4-carbamoyl-2,6-dimethyl-phenyl)-propionyl]-[1-(4-phenyl-- 1h-imidazol-2-yl)-ethyl]-amino}-methyl)-2-methoxy-benzoic acid and methods of making the zwitterion of 5-({[2-amino-3-(4-carbamoyl-2,6-dimethyl-phenyl)-propionyl]-[1-(4-phenyl-- 1h-imidazol-2-yl)-ethyl]-amino}-methyl)-2-methoxy-benzoic acid.
Inventor(s): Anzalone; Luigi (West Chester, PA), Villani; Frank J. (Perkasie, PA), Teleha; Christopher A. (Fort Washington, PA), Feibush; Penina (Ambler, PA), Fegely; Barry (Quakertown, PA)
Assignee: Forest Tosara Limited (Dublin, IE)
Application Number:14/806,465
Patent Claims: 1. A method of treating a mammal suffering from irritable bowel syndrome comprising administering to said mammal an effective amount of a Form .alpha. crystal of 5-({[2-amino-3-(4-carbamoyl-2,6-dimethyl-phenyl)-propionyl]-[1-(4-phenyl-- 1H-imidazol-2-yl)-ethyl]-amino}-methyl)-2-methoxy-benzoic acid.

2. The method of claim 1, wherein said Form .alpha. crystal is characterized by a powder X-ray diffraction pattern having powder X-ray diffraction peaks at about 14.0, 14.3, and 14.7 degrees 2-theta.

3. The method of claim 1, wherein said Form .alpha. crystal is characterized by a powder X-ray diffraction pattern having powder X-ray diffraction peaks at about 10.2, 11.3, 14.0, 14.3, and 14.7 degrees 2-theta.

4. The method of claim 1, wherein said Form .alpha. crystal is characterized by a powder X-ray diffraction pattern having powder X-ray diffraction peaks at about 10.2, 11.3, 11.8, 14.0, 14.3, 14.7, 16.1, and 18.3 degrees 2-theta.

5. The method of claim 1, wherein said Form .alpha. crystal is characterized by a powder X-ray diffraction pattern having powder X-ray diffraction peaks substantially as shown in Table 1.

6. The method of claim 1, wherein said Form .alpha. crystal is characterized by a powder X-ray diffraction pattern having powder X-ray diffraction peaks substantially similar to the powder X ray diffraction peaks of FIG. 1.

7. The method of claim 1, wherein said Form .alpha. crystal is characterized by a thermal gravimetric analysis (TGA) substantially similar to the TGA in FIG. 2.

8. The method of claim 1, wherein said Form .alpha. crystal is characterized by a differential scanning calorimetry (DSC) measurement substantially similar to the DSC in FIG. 3.

9. A method of treating a mammal suffering from pain comprising administering to said mammal an effective amount of a Form .alpha. crystal of 5-({[2-amino-3-(4-carbamoyl-2,6-dimethyl-phenyl)-propionyl]-[1-(4-phenyl-- 1H-imidazol-2-yl)-ethyl]-amino}-methyl)-2-methoxy-benzoic acid.

10. The method of claim 9, wherein said Form .alpha. crystal is characterized by a powder X-ray diffraction pattern having powder X-ray diffraction peaks at about 14.0, 14.3, and 14.7 degrees 2-theta.

11. The method of claim 9, wherein said Form .alpha. crystal is characterized by a powder X-ray diffraction pattern having powder X-ray diffraction peaks at about 10.2, 11.3, 14.0, 14.3, and 14.7 degrees 2-theta.

12. The method of claim 9, wherein said Form .alpha. crystal is characterized by a powder X-ray diffraction pattern having powder X-ray diffraction peaks at about 10.2, 11.3, 11.8, 14.0, 14.3, 14.7, 16.1, and 18.3 degrees 2-theta.

13. The method of claim 9, wherein said Form .alpha. crystal is characterized by a powder X-ray diffraction pattern having powder X-ray diffraction peaks substantially as shown in Table 1.

14. The method of claim 9, wherein said Form .alpha. crystal is characterized by a powder X-ray diffraction pattern having powder X-ray diffraction peaks substantially similar to the powder X ray diffraction peaks of FIG. 1.

15. The method of claim 9, wherein said Form .alpha. crystal is characterized by a thermal gravimetric analysis (TGA) substantially similar to the TGA in FIG. 2.

16. The method of claim 9, wherein said Form .alpha. crystal is characterized by a differential scanning calorimetry (DSC) measurement substantially similar to the DSC in FIG. 3.

17. A method of treating a mammal suffering from irritable bowel syndrome comprising administering to said mammal an effective amount of a Form .beta. crystal of 5-({[2-amino-3-(4-carbamoyl-2,6-dimethyl-phenyl)-propionyl]-[1-(4-phenyl-- 1H-imidazol-2-yl)-ethyl]-amino}-methyl)-2-methoxy-benzoic acid.

18. A method of treating a mammal suffering from pain comprising administering to said mammal an effective amount of a Form .beta. crystal of 5-({[2-amino-3-(4-carbamoyl-2,6-dimethyl-phenyl)-propionyl]-[1-(4-phen- yl-1H-imidazol-2-yl)-ethyl]-amino}-methyl)-2-methoxy-benzoic acid.

19. The method of claim 17, wherein said Form .beta. crystal is characterized by a powder X-ray diffraction pattern having powder X-ray diffraction peaks at about 11.0, 12.4, and 15.2 degrees 2-theta.

20. The method of claim 17, wherein said Form .beta. crystal is characterized by a powder X-ray diffraction pattern having powder X-ray diffraction peaks at about 11.0, 12.4, 14.9, 15.2, and 22.1 degrees 2-theta.

21. The method of claim 17, wherein said Form .beta. crystal is characterized by a powder X-ray diffraction pattern having powder X-ray diffraction peaks at about 11.0, 12.4, 14.9, 15.2, 22.1, 25.6, 27.4, and 30.4 degrees 2-theta.

22. The method of claim 17, wherein said Form .beta. crystal is characterized by a powder X-ray diffraction pattern having powder X-ray diffraction peaks substantially as shown in Table 2.

23. The method of claim 17, wherein said Form .beta. crystal is characterized by a powder X-ray diffraction pattern having powder X-ray diffraction peaks substantially similar to the powder X ray diffraction peaks of FIG. 1.

24. The method of claim 17, wherein said Form .beta. crystal is characterized by a thermal gravimetric analysis (TGA) substantially similar to the TGA in FIG. 4.

25. The method of claim 17, wherein said Form .beta. crystal is characterized by a differential scanning calorimetry (DSC) measurement substantially similar to the DSC in FIG. 5.

26. The method of claim 18, wherein said Form .beta. crystal is characterized by a powder X-ray diffraction pattern having powder X-ray diffraction peaks at about 11.0, 12.4, and 15.2 degrees 2-theta.

27. The method of claim 18, wherein said Form .beta. crystal is characterized by a powder X-ray diffraction pattern having powder X-ray diffraction peaks at about 11.0, 12.4, 14.9, 15.2, and 22.1 degrees 2-theta.

28. The method of claim 18, wherein said Form .beta. crystal is characterized by a powder X-ray diffraction pattern having powder X-ray diffraction peaks at about 11.0, 12.4, 14.9, 15.2, 22.1, 25.6, 27.4, and 30.4 degrees 2-theta.

29. The method of claim 18, wherein said Form .beta. crystal is characterized by a powder X-ray diffraction pattern having powder X-ray diffraction peaks substantially as shown in Table 2.

30. The method of claim 18, wherein said Form .beta. crystal is characterized by a powder X-ray diffraction pattern having powder X-ray diffraction peaks substantially similar to the powder X ray diffraction peaks of FIG. 1.

31. The method of claim 18, wherein said Form .beta. crystal is characterized by a thermal gravimetric analysis (TGA) substantially similar to the TGA in FIG. 4.

32. The method of claim 18, wherein said Form .beta. crystal is characterized by a differential scanning calorimetry (DSC) measurement substantially similar to the DSC in FIG. 5.
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