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Generated: August 24, 2017

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Title:Crystalline pharmaceutical and methods of preparation and use thereof
Abstract: Novel crystalline polymorphic forms, Forms A, B, C, D, and E of a compound of Formula I, which has been found to be a potent inhibitor of LFA-1, are disclosed. Methods of preparation and uses thereof in the treatment of LFA-1 mediated diseases are also disclosed in this invention. ##STR00001##
Inventor(s): Burnier; John (Pacifica, CA), Gadek; Thomas (Oakland, CA), Naud; Frederic (Binningen, CH)
Assignee: Sarcode Bioscience Inc. (Brisbane, CA)
Filing Date:Apr 15, 2009
Application Number:12/386,361
Claims:1. A compound of the formula: ##STR00028## or its pharmaceutically acceptable salts.

2. A compound of the formula: ##STR00029## or its pharmaceutically acceptable salts.

3. A compound of the formula: ##STR00030##

4. A compound of the formula: ##STR00031## or its pharmaceutically acceptable salts.

5. A reaction mixture comprising the compound of claim 1 or 2, a solvent, and a coupling reagent.

6. The reaction mixture of claim 5 further comprising a base.

7. The reaction mixture of claim 6 comprising the compound of ##STR00032## or its pharmaceutically acceptable salts.

8. The reaction mixture of claim 7 wherein a compound of the formula: ##STR00033## is produced.

9. The reaction mixture of claim 5 wherein the solvent is DMF.

10. The reaction mixture of claim 5 wherein the coupling reagent is 2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU).

11. The reaction mixture of claim of claim 6 wherein the base is triethylamine.

12. A compound of the formula: ##STR00034##

13. A reaction mixture comprising the compound of claim 4, a solvent, and an acid.

14. The reaction mixture of claim 4 wherein a compound of the formula: ##STR00035## is produced.

15. The reaction mixture of claim 13 wherein the solvent is dioxane.

16. The reaction mixture of claim 13 wherein the acid is HCl.

17. A reaction mixture comprising the compound of claim 12, a solvent, and a base.

18. The reaction mixture of claim 17 further comprising benzofuranoyl chloride.

19. The reaction mixture of claim 18 wherein a compound of the formula: ##STR00036## is produced.

20. The reaction mixture of claim 17 wherein the solvent is methylene chloride.

21. The reaction mixture of claim 17 wherein the base is diisopropylethylamine.
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