(11) Application No. AU 2006302237 C1 (19) AUSTRALIAN PATENT OFFICE

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(11) Application No. AU 2006302237 C1 (19) AUSTRALIAN PATENT OFFICE (12) STANDARD PATENT (11) Application No. AU 2006302237 C1 (19) AUSTRALIAN PATENT OFFICE (54) Title Multi-functional ionic liquid compositions (51) International Patent Classification(s) C11D 17/00 (2006.01) (21) Application No: 2006302237 (22) Date of Filing: 2006.10.10 (87) WIPO No: WO07/044693 (30) Priority Data (31) Number (32) Date (33) Country 60/764,850 2006.02.02 US 60/724,605 2005.10.07 US 60/724,604 2005.10.07 US (43) Publication Date: 2007.04.19 (44) Accepted Journal Date: 2012.03.08 (44) Amended Journal Date: 2012.11.08 (71) Applicant(s) The University of Alabama (72) Inventor(s) Hough, Whitney L.;Davis Jr., James Hillard;Daly, Daniel T.;Spear, Scott K.;Smiglak, Marcin;Swatloski, Richard P.;Pernak, Juliusz;Rogers, Robin D. (74) Agent / Attorney Griffith Hack, GPO Box 1285, Melbourne, VIC, 3001 (56) Related Art D3: WELTON, Thomas: "Room-Temperature Ionic Liquids. Solvents for Synthesis and Catalysis" CHEMICAL REVIEWS, Vol. 99, No. 8, 7 July 1999, pages 2071-2083. JP 2005-082512 A (MEDOREKKUSU KK) 31 March 2005 AU 2005232025 A1 (THE UNIVERSITY OF YORK) 20 October 2005 WO 2002/0079269 A1 (THE UAB RESEARCH FOUNDATION) 10 October 2002 EP 1405646 A2 (YUNG SHIN PHARM. IND. CO. LTD.) 7 April 2004 PICQUET, M., et. al.: "Ionic liquids: media for better molecular catalysis" TOPICS IN CATALYSIS, vol. 29, no. 3-4, 1 June 2004 (2004-06-01), pages 139-143 (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau IIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIN (10) International Publication Number (43) International Publication Date PCT 19 April 2007 (19.04.2007) WO 2007/044693 A3 (51) International Patent Classification: Tuscaloosa, AL 35401 (US). SWATLOSKI, Richard, P. Cl ID 17/00 (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) International Filing Date: 10 October 2006 (10.10.2006) 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 [PT,/PL]; UL. Nalkowskiej, 8A, PT,-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 P.C., 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, ECT, ES, El, (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 (57) Abstract: Disclosed are ionic liquids [Hex]Siilfacetamide, [HexJCI & Na Sulfacetamide Dissolution and 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. llllllllllllllllllllllllllllllllllllllllllllllllllllll^ A3 Time (min) -------- Cation [Hex][ClJ 2007/044693 -------- Anion [NaJSulfacetamide -------- Ionic Liquid [Hex]Sulfacetaffiide wo WO 2007/044693 A3 lllllllllllllllllllllllllllllllllllllllllllll^ NA, NG, NI, NO, NZ, OM, PG, PH, PL. PT, RO, RS, RU, Published: SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, — with international search report TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. — before the expiration of the time limit for amending the claims and to be republished in the event of receipt of (84) Designated States (unless otherwise indicated, for every amendments kind of regional protection available)·. ARIPO (BW, GH, GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, (88) Date of publication of the international search report: ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), 23 August 2007 European (AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, ΈΙ, FR, GB, GR, HU, IE, IS, IT, LT, LU, LV, MC, NL, PL, PT, For two-letter codes and other abbreviations, refer to the "Guid­ RO, SE, SI, SK, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, ance Notes on Codes and Abbreviations" appearing at the begin­ GN, GQ, GW, ML, MR, NE, SN, TD, TG). ning of each regular issue of the PCT Gazette. WO 2007/044693 PCT/US2006/039454 MULTI-FUNCTIONAL IONIC LIQUID COMPOSITIONS FOR OVERCOMING POLYMORPHISM AND IMPARTING IMPROVED PROPERTIES FOR ACTIVE PHARMACEUTICAL, BIOLOGICAL, NUTRITIONAL, AND ENERGETIC INGREDIENTS 5 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, 10 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 15 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 20 Molecular Crystals,” IUCR Monographs on Crystallography 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 Sci 1975, 64:1269-1288). 25 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 30 been termed “pseudo-polymorphism.” Akin to polymorphs, such “pseudo-polymorphs,” 1 WO 2007/044693 PCT/US2006/039454 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 5 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 10 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, in Brittain, H.G., Ed., Vol. 95 οΐDrugs and the Pharmaceutical Sciences, Marcel Dekker, Inc., New York, 15 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 20 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 25 (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 30 properties. For example, one particular polymorph pseudo-polymorph may be more bioavailable, more stable (e.g., longer shelflife), or more easily formulated or tableted than another polymorph.
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