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(12) United States Patent (10) Patent No.: US 8,802,596 B2 Rogers Et Al

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(12) United States Patent (10) Patent No.: US 8,802,596 B2 Rogers Et Al USOO8802596B2 (12) United States Patent (10) Patent No.: US 8,802,596 B2 Rogers et al. (45) Date of Patent: Aug. 12, 2014 (54) MULTI-FUNCTIONAL IONIC LIQUID (58) Field of Classification Search COMPOSITIONS FOR OVERCOMING None POLYMORPHISMAND IMPARTING See application file for complete search history. IMPROVED PROPERTIES FORACTIVE PHARMACEUTICAL, BIOLOGICAL, NUTRITIONAL AND ENERGETIC (56) References Cited INGREDIENTS U.S. PATENT DOCUMENTS Inventors: (75) Robin D. Rogers, Tuscaloosa, AL (US); 1943,176 A 1/1934 Graenacher Daniel T. Daly, Tuscaloosa, AL (US); 3,223,704 A 12, 1965 Shibe Richard P. Swatloski, Tuscaloosa, AL 3,344,018 A 9, 1967 Shibe (US); Whitney L. Hough-Troutman, 3.414,569 A 12/1968 Wieden Tuscaloosa, AL (US); James Hilliard 3.47 1423 A 10, 1969 Elmer 4,097.666 A 6, 1978 Johnson et al. Davis, Jr., Mobile, AL (US); Marcin 4,104,368 A 8, 1978 Lala et al. Smiglak, Tuscaloosa, AL (US); Juliusz 4,188,263. A 2, 1980 Hulsmann et al. Pernak, Pozan (PL); Scott K. Spear, 4,224,319 A 9, 1980 Marcadet Bankston, AL (US) 4,228, 162 A 10, 1980 Luzzi et al. 4,491,574 A 1/1985 Seifter et al. (73) Assignee: Board of Trustees of the University of 4,520,105 A 5, 1985 Sinner et al. Alabama, Tuscaloosa, AL (US) 4,637,830 A 1/1987 Dyer et al. 4,761,164 A 8, 1988 Pez et al. (*) Notice: Subject to any disclaimer, the term of this 4,973,456 A 1 1/1990 Quinn et al. patent is extended or adjusted under 35 5,175,353 A 12/1992 Jones et al. U.S.C. 154(b) by 0 days. 5,221,758 A 6/1993 Maynard 5,246,716 A 9, 1993 Sedun et al. (21) Appl. No.: 13/491,053 5,275,820 A 1/1994 Chang 5,428,000 A 6/1995 Innami et al. (22) Filed: Jun. 7, 2012 5,654,337 A 8, 1997 Roentsch et al. (65) Prior Publication Data 5,679,146 A 10, 1997 Kalt et al. 5,683,832 A 11/1997 Bonhote et al. US 2012/O264605 A1 Oct. 18, 2012 (Continued) Related U.S. Application Data FOREIGN PATENT DOCUMENTS (62) Division of application No. 1 1/545,938, filed on Oct. 10, 2006, now Pat. No. 8,232,265. CA 2619367 T 2009 (60) Provisional application No. 60/764,850, filed on Feb. DE 93-43O8410 3, 1993 2, 2006, provisional application No. 60/724,604, filed (Continued) on Oct. 7, 2005, provisional application No. 60/724,605, filed on Oct. 7, 2005. OTHER PUBLICATIONS Int. C. Office Action for Application No. JP 2008-534766 dated Sep. 13, (51) 2012. AOIN 57/18 (2006.01) Avent et al., Evidence for hydrogen bonding in solutions of 1-Ehtyl AOIN 43/707 (2006.01) 3-imidazolium Halides, and its implications for ambient temperature AOIN 43/66 (2006.01) Halogenoaluminate (III) ionic liquids, J. Chem. Soc. Dalton Trans. AOIN 43/68 (2006.01) 3405-3413 (1994). AOIN 43/58 (2006.01) Bates et al., CO2 capture by a task-specific ionic liquid, J. Am. Chem AOIN 43/82 (2006.01) Soc., 124(6):926-927 (2002). AOIN 43/78 (2006.01) AOIN 43/76 (2006.01) (Continued) AOIN 43/80 (2006.01) AOIN 43/653 (2006.01) Primary Examiner — Alton Pryor AOIN 43/10 (2006.01) (74) Attorney, Agent, or Firm — Meunier Carlin & Curfman, AOIN37/00 (2006.01) LLC AOIN37/18 (2006.01) AOIN33/18 (2006.01) AOIN 43/90 (2006.01) (57) ABSTRACT AOIN 43/54 (2006.01) Disclosed are ionic liquids and methods of preparing ionic AOIN 43/40 (2006.01) liquid compositions of active pharmaceutical, biological, AOIN 43/42 (2006.01) nutritional, and energetic ingredients. Also disclosed are AOIN 43/48 (2006.01) methods of using the compositions described herein to over (52) U.S. C. come polymorphism, overcome solubility and delivery prob USPC ........... 504/206:504/229; 504/231:504/232: lems, to control release rates, add functionality, enhance effi 504/236:504/238; 504/262:504/267: 504/270; cacy (synergy), and improve ease of use and manufacture. 504/271; 504/272; 504/289; 504/307: 504/334; 504/347; 504/241; 504/243; 504/244; 504/247; 504/253: 504/255 13 Claims, 6 Drawing Sheets US 8,802,596 B2 Page 2 (56) References Cited Bernstein, Crystal structure prediction and polymorphism, ACA Transactions, 39:14-23 (2004). U.S. PATENT DOCUMENTS Black et al., Increased chemical purity using a hydrage, Crystal Growth & Design, 4(3):539-544 (2004). 5,731, 101 A 3, 1998 Sherifet al. Bonhote et al., Hydrophobic, highly conductive ambient-temperature 5,792,399 A 8, 1998 Miester et al. 5,827,602 A 10, 1998 Koch et al. molten salts, Inorg. 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Cuppen et al., Crystal structure and growth behavior of aspartame 2010/0280090 A1 11/2010 Hamamoto et al. form I-A, Crystal Growth & Design, 5(3):917-923 (2005). Davis et al. Thiazolium-ion based organic ionic liquids (OILS). FOREIGN PATENT DOCUMENTS Novel OILs which promote the benzoinc condensation, Tetrahedron Lett., 40: 1621-1622 (1999). ES 8406412 4f1983 Davis et al., From curiosities to commodities: Ionic liquids begin the FR 1404697 5, 1965 transformation, Chem. Comm. 1209-1212 (2003). GB 869149 5, 1961 Domagk, A new class of disinfectants, Deut. Med. Wochenschr, GB 1067094 5, 1964 GB 1473.603 5, 1977 61:829-832 (1935). JP 61-236818 10, 1986 Dupont et al., Room temperature molten salts: Neuteric "Green” JP 62-198609 9, 1987 Solvents for chemical reactions and processes, Braz. Chem. Soc. JP 63-0565O1 3, 1988 11(4):337-344 (2000). 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