Details for Patent: 8,378,105

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)
Assignee:	SARcode Bioscience Inc. (Brisbane, CA)
Filing Date:	Oct 21, 2010
Application Number:	12/909,241
Claims:	1. A method of synthesizing a compound of Formula I: ##STR00020## or a salt thereof comprising the steps: a) performing base hydrolysis of Formula AA with a base in an aprotic solvent: ##STR00021## wherein R is a carbon containing moiety; and b) isolating a compound of Formula I, or a salt thereof, with an enantiomeric excess of greater than about 90%. 2. The method of claim 1, wherein the aprotic solvent is dioxane. 3. The method of claim 1, wherein the base is sodium hydroxide. 4. The method of claim 1, wherein R is a substituted or unsubstituted group selected from lower alkyl, lower alkenyl, lower alkynyl, cyclo(lower)alkyl, cyclo(lower)alkenyl, aryl, aralkyl, heterocyclyl, and heteroaryl groups. 5. The method of claim 1, comprising the steps: a) performing base hydrolysis of Formula A: ##STR00022## with a base in an aprotic solvent; and b) isolating a compound of Formula I or a salt thereof. 6. The method of claim 5, wherein the aprotic solvent is dioxane. 7. The method of claim 5, wherein the base is sodium hydroxide. 8. A method of synthesizing a compound of Formula I: ##STR00023## or a salt thereof comprising the steps: a) performing acid hydrolysis of Formula AA with an acid in an aprotic solvent: ##STR00024## wherein R is a carbon containing moiety; and b) isolating a compound of Formula I, or a salt thereof, with an enantiomeric excess of greater than about 90%. 9. The method of claim 8, wherein the aprotic solvent is dioxane. 10. The method of claim 8, wherein the acid is hydrogen chloride. 11. The method of claim 8, wherein R is a substituted or unsubstituted group selected from lower alkyl, lower alkenyl, lower alkynyl, cyclo(lower)alkyl, cyclo(lower)alkenyl, aryl, aralkyl, heterocyclyl, and heteroaryl groups. 12. The method of claim 8, comprising the steps: a) performing acid hydrolysis of Formula A: ##STR00025## with an acid in an aprotic solvent; and b) isolating a compound of Formula I or a salt thereof. 13. The method of claim 12, wherein the aprotic solvent is dioxane. 14. The method of claim 12, wherein the acid is hydrogen chloride.