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Wo 2007/044693 A2 (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (43) International Publication Date PCT (10) International Publication Number 19 April 2007 (19.04.2007) WO 2007/044693 A2 (51) International Patent Classification: Tuscaloosa, AL 35401 (US). SWATLOSKI, Richard, P. A61K 31/555 (2006.01) A61K 31/28 (2006.01) [US/US]; 1801 Waterford Lane, Tuscaloosa, AL 35405 (21) International Application Number: (US). HOUGH, Whitney, L. [US/US]; 226 Wolf Creek PCT/US2006/039454 Drive, Albertville, AL 35951 (US). DAVIS, James, Hillard [US/US]; 324 Vanderbilt Drive, Mobile, AL (22) 10 October 2006 (10.10.2006) International Filing Date: 36608 (US). SMIGLAK, Marcin [PL/US]; 3302 Sixth (25) Filing Language: English Avenue East, Apt. C, Tuscaloosa, AL 35405 (US). PER- (26) Publication Language: English NAK, Juliusz [PL/PL]; UL. Nalkowskiej, 8A, PL-60-573 Poznan (PL). SPEAR, Scott, K. [US/US]; 302 County (30) Priority Data: Road 49, Bankston, AL 35542 (US). 60/724,604 7 October 2005 (07.10.2005) US 60/724,605 7 October 2005 (07.10.2005) US (74) Agents: KATZ, Mitchell, A. et al.; Needle & Rosenberg, 60/764,850 2 February 2006 (02.02.2006) US PC, Suite 1000, 999 Peachtree Street, Atlanta, GA 30309- (71) Applicant (for all designated States except US): THE 3915 (US). UNIVERSITY OF ALABAMA [US/US]; 222 Rose (81) Designated States (unless otherwise indicated, for every Administration Building, Post Office Box 870106, kind of national protection available): AE, AG, AL, AM, Tuscaloosa, AL 35487-0106 (US). AT,AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, (72) Inventors; and CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, (75) Inventors/Applicants (for US only): ROGERS, Robin, GB, GD, GE, GH, GM, HN, HR, HU, ID, IL, IN, IS, JP, D. [US/US]; 32 Audubon Place, Tuscaloosa, AL 35401 KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, (US). DALY, Daniel, T. [US/US]; 1518 Mallard Circle, LU, LV,LY,MA, MD, MG, MK, MN, MW, MX, MY, MZ, [Continued on next page] (54) Title: MULTI-FUNCTIONAL IONIC LIQUID COMPOSITIONS FOR OVERCOMING POLYMORPHISM AND IMPART- ING IMPROVED PROPERTIES FOR ACTIVE PHARMACEUTICAL, BIOLOGICAL, NUTRITIONAL, AND ENERGETIC IN- GREDIENTS (57) Abstract: Disclosed are ionic liquids and [Hex]Sulfacetamide, [Hex]Cl & Na Sulfacetamide Dissolution methods of preparing ionic liquid compositions of active pharmaceutical, biological, nutritional, and energetic ingredients. Also disclosed are methods of using the compositions described herein to overcome polymorphism, overcome solubility and delivery problems, to control release rates, add functionality, enhance efficacy (synergy), and improve ease of use and manufacture. Time (mitt) NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, RO, SE, SI, SK, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, GN, GQ, GW, ML, MR, NE, SN, TD, TG). TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. Published: (84) Designated States (unless otherwise indicated, for every — without international search report and to be republished kind of regional protection available): ARIPO (BW, GH, upon receipt of that report GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), For two-letter codes and other abbreviations, refer to the "G uid European (AT,BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, ance Notes on Codes and Abbreviations" appearing at the beg in FR, GB, GR, HU, IE, IS, IT, LT,LU, LV,MC, NL, PL, PT, ning of each regular issue of the PCT Gazette. MULTI-FUNCTIONAL IONIC LIQUID COMPOSITIONS FOR OVERCOMING POLYMORPHISM AND IMPARTING IMPROVED PROPERTIES FORACTIVE PHARMACEUTICAL, BIOLOGICAL, NUTRITIONAL, AND ENERGETIC INGREDIENTS CROSS-REFERENCE TO RELATED APPLICATIONS This patent application claims the benefit of priority to U.S. Provisional Application No. 60/764,850, filed February 2, 2006, U.S. Provisional Application No. 60/724,604, filed October 7, 2005, and U.S. Provisional Application No. 60/724,605, filed October 7, 2005, which are each incorporated by reference herein in their entireties. FIELD The subject matter disclosed herein generally relates to ionic liquids and to methods of preparing ionic liquid compositions of active pharmaceutical, biological, nutritional, and energetic ingredients. Also the subject matter disclosed herein generally relates to methods of using the compositions described herein to overcome polymorphism, overcome solubility and delivery problems, to control release rates, add functionality, enhance efficacy (synergy), and improve ease of use and manufacture. BACKGROUND Polymorphism is the ability of a substance to exist in two or more crystalline forms that have a different arrangement and/or conformation of molecules in a crystalline lattice (see e.g., Chawla and Bansal, CRIPS 2004, 5(1):9-12; Bernstein, "Polymorphism in Molecular Crystals," IUCR Monographs on Crystallography 14 Oxford Science Publications, 2002, pp. 1-28, 240-256). It has been estimated that a large number of pharmaceuticals exhibit polymorphism. For example, 70% of barbiturates, 60% of sulfonamides, and 23% of steroids are believed to exist in different polymorphic forms or "polymorphs" (Haleblian et al, JPharm Sd 1975, 64:1269-1288). In some cases, when crystals of a compound are forming (e.g., crystallizing from a solution), solvent molecules may become entrapped or bound within the crystal lattice. The presence of the entrapped solvent molecules may affect the three-dimensional crystal lattice that eventually crystallizes. The occurrence of a compound (target molecule) crystallizing in different three-dimensional lattices based upon the presence of solvent molecules has been termed "pseudo-polymorphism." Akin to polymorphs, such "pseudo-polymorphs," also known as "solvates" (or "hydrates" when the solvent is water), are crystalline solids containing either stoichiometric (i.e., whole number ratios of target molecules to solvent molecules) or non-stoichiometric (i.e., non-whole number ratios of target molecules to solvent molecules) amounts of a solvent incorporated within the crystal structure. In general, different crystalline forms of molecules (e.g., pharmaceutical compounds) can exist in the same or different hydrated or solvated states. The Cambridge Structural Database (Allen, "The Cambridge Structural Database: a quarter of a million crystal structures and rising," Acta Crystallographica, 2002, B58, 380- 388) is a database of over 300,000 organic crystal structures and is a widely used reference source in crystallography. One survey of the Cambridge Structural Database shows that pharmaceutical compounds have been reported to exist as hemi-hydrates (0.5 water molecules) through decahydrates (10 water molecules). (Morris, "Structural Aspect of Hydrates and Solvates," Ch. 4 in- Polymorphism in Pharmaceutical Solids, inBrittain, H.G., Ed., Vol. 95 of Drugs and the Pharmaceutical Sciences, Marcel Dekker, Inc., New York, NY, 1999, 125-181.) The possibility of polymorphism or pseudo-polymorphism may exist for any particular compound, but the conditions required to prepare as yet unknown polymorphs or pseudo-polymorphs are not easily determined (see e.g., Bernstein, "Crystal Structure Prediction and Polymorphism," Am Crystallographic Assoc Trans, 2004, 39: 14-23). The knowledge that one type of polymorph or pseudo-polymorph of a crystalline form of a compound exists, or that a given set of crystallization conditions leads to the production of one type of polymorph or pseudo-polymorph, does not typically allow researchers to predict what other types of polymorph or pseudo-polymorph might exist, or what type of polymorph or pseudo-polymorph would be produced by other crystallization conditions (Guillory, "Generation of Polymorphs, Hydrates, Solvates, and Amorphous Solids," Ch. 5 in Polymorphism in Pharmaceutical Solids, Brittain, H. G., Ed., Vol. 95 of Drugs and the Pharmaceutical Sciences, Marcel Dekker, Inc., New York, NY, 1999, pp. 183-226). The existence of various polymorphs or pseudo-polymorphs can greatly affect a pharmaceutical' s performance since each form can have different physical and chemical properties. For example, one particular polymorph pseudo-polymorph may be more bioavailable, more stable (e.g., longer shelf life), or more easily formulated or tableted than another polymorph. Similarly, one polymorph pseudo-polymorph may be more active or less toxic than another. Some specific examples of the dramatic difference that can exist between various pharmaceutical polymorphs are described in, e.g., Brittain et al, JPharm Sci 2002, 91:1573-1580 and Morissette et al, Proc Natl Acad Sd USA 2003, 100:2180- 2184. The effects of polymorphism and pseudo-polymorphism on quality and performance of a drug is widely recognized. The exact solid state polymorph (or pseudo-polymorph) of a compound determines its physical properties such as dissolution rate, solubility, bioavailability, crystal habit, mechanical strength, etc. (Datta et al, Nature Reviews-Drug Discovery, 2004, 3:42-57). The delivery of an exact dosage in manufacture and the manufacturing process itself often depend on which of several possible polymorphs or pseudo-polymorphs are present. The variation in properties among different polymorphs (or pseudo-polymorphs) usually means that one crystalline form is desired or preferred over other forms. Obtaining a particular form can be difficult, however. Typically, researchers have to experiment with a multitude of variables in
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