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T |?: 9. 3:08: Such Pharmaceutical Compositions. (52) U.S USOO93O8213B2 (12) United States Patent (10) Patent No.: US 9,308,213 B2 Bannister et al. 45) Date of Patent: *Apr. 12,9 2016 (54) SOLID SOLUTION COMPOSITIONS AND USE (2013.01); A61 K9/2013 (2013.01); A61 K IN CHRONIC INFLAMMATION 31/192 (2013.01); A61 K3I/60 (2013.01); A61K 47/44 (2013.01); A61 K3 1/201 (2013.01); (71) Applicant: Infirst Healthcare Limited, London A61 K 3 1/202 (2013.01); A61K 31/25 (2013.01); (GB) A61 K 3 1/337 (2013.01); A61 K3I/704 (72) Inventors: Robin M. Bannister, Essex (GB); John (2013.01) Brew, Hertfordshire (GB); Richard R. (58) Field of Classification Search Caparros Wanderley, Buckinghamshire A61 K31/704; A61 K31/60; A61 K31/202 (GB) USPC .......................................... 514/159,570,571 See application file for complete search history. (73) Assignee: Infirst Healthcare Limited (GB) (*) Notice: Subject to any disclaimer, the term of this (56) References Cited patent is extended or adjusted under 35 U.S.C. 154(b) by 0 days U.S. PATENT DOCUMENTS This patent is Subject to a terminal dis- 3,228,831 A 1/1966 Nicholson et al. claimer 3,800,038 A 3, 1974 Rudel 4,571.400 A 2f1986 Arnold 4,684.666 A 8, 1987 HaaS (21) Appl. No.: 14/155,108 4,918, 103 A 4/1990 Park et al. 5,011,852 A 4, 1991 Park et al. (22) Filed: Jan. 14, 2014 5,059,626 A 10, 1991 Park et al. 5,154,930 A 10/1992 Popescu (65) Prior Publication Data 5,552,160 A 9/1996 Liversidge et al. 5,645,856 A 7/1997 Lacy et al. US 2014/O162988 A1 Jun. 12, 2014 5,955.451 A 9/1999 Lichtenberger et al. 6,267,985 B1 7/2001 Chen et al. 6,294,192 B1 9, 2001 Patel et al. Related U.S. Application Data 6,319,513 B1 1 1/2001 Dobrozsi 6,383,471 B1 5/2002 Ch tal. (63) Continuation-in-part of application No. 13/365,824, 6,451,339 B2 9, 2002 ES filed on Feb. 3, 2012, now Pat. No. 8,895,536, which is 6,923,988 B2 8, 2005 Patel et al. a continuation-in-part of application No. 7,473.432 B2 ck 3. Cevc et al. 1 f 8,895,536 B2 * 1 1/2014 Bannister et al. ............. 514f159 PCT/GB2012/0521 15, filed on Oct. 31, 2O1 1. 8,895,537 B2 * 1 1/2014 Bannister et al. ............. 514f159 application No. 14/155,108, which is a continuation-in-part of application No. 13/365,828, (Continued) filed on Feb. 3, 2012, now Pat. No. 8,895,537. FOREIGN PATENT DOCUMENTS (60) Provisional application No. 61/752,309, filed on Feb. 4, 2013, provisional application No. 61/752,356, filed CN 1736,369 2, 2006 on Jan. 14, 2013. CN 101.129335 A * 2, 2008 (Continued) (30) Foreign Application Priority Data OTHER PUBLICATIONS Oct. 29, 2010 (GB) ................................... 1018289.7 Feb. 4, 2011 (GB) ... ... 11 O1937.9 CN 101 12935 A. English translation and English-translated abstract Aug. 10, 2011 (GB) ..... 11 13728.8 (2008).* Aug. 10, 2011 (GB) ..... ... 1113729.6 (Continued) Aug. 10, 2011 (GB) ................................... 1113730.4 (51) Ek',I/60 (2006.01) Primary Examiner — Kevin E Weddington A6 IK3I/9 (2006.01) (74) Attorney, Agent, or Firm One3 IP Management, P.C.; A6 IK3I/66 (2006.01) Dean G. Stathakis; Peter D. Weisintein A6 IK3I/92 (2006.01) A6 IK9/08 (2006.01) A6 IK 47/44 (2006.01) (57) ABSTRACT A6 IK9/20 (2006.01) The present specification discloses pharmaceutical composi A61 K3 1/25 (2006.01) tions, methods of preparing Such pharmaceutical composi A61 K3 L/704 (2006.01) tions, and methods and uses of treating a chronic inflamma A61 K3 1/337 (2006.01) tion and/or an inflammatory disease in an individual using t |?: 9. 3:08: Such pharmaceutical compositions. (52) U.S. Cl. CPC ................. A61 K3I/616 (2013.01); A61 K9/08 26 Claims, 10 Drawing Sheets US 9,308,213 B2 Page 2 (56) References Cited WO 2008.120207 A3 10, 2008 WO 2008, 134512 A1 11, 2008 U.S. PATENT DOCUMENTS WO 2009/033131 A2 3, 2009 WO 2009/047785 A3 4/2009 2003,0008003 A1 1/2003 Jamali WO 2009/067734 A1 6, 2009 2003/0170279 A1 9, 2003 Lambert et al. WO 2009/069139 A1 6, 2009 2003/0232097 A1 12/2003 Radhakrishnan et al. WO 2010/059717 A2 5, 2010 2004.0024057 A1 2, 2004 Earl et al. WO 2010/087947 A2 8, 2010 2004/025.3276 A1 12, 2004 Sato et al. WO 2010/0973.32 A1 9, 2010 2005/0152968 A1 7/2005 Brophy et al. WO 2010/097334 A1 9, 2010 2006, OO6281.0 A1 3, 2006 WoO et al. WO 2010.103312 A1 9, 2010 2006/0078616 A1 4/2006 Georgewill et al. WO 2011/095814 A1 8, 2011 2007/0015834 A1 1/2007 Flashner-Barak et al. WO 2012/056251 A1 5, 2012 2007/0026062 A1 2/2007 Holm et al. WO 2012, 104654 A1 8, 2012 2007.0036831 A1, 2, 2007 Baker WO 2012, 104655 A2 8, 2012 2007, 0104741 A1 5/2007 Murty et al. 2007. O190080 A1 8, 2007 Friedman OTHER PUBLICATIONS 3883 A. 258. Still al. The English translation abstract for FR 2810243 A1, Woo et al. 2008. O15421.0 A1 6/2008 Jordan et al. (2001). 20090304782 A1 12, 2009 De Blas et al. Csizmazia, E., et al., Penetration enhancer effect of Sucrose laurate 2010.0099767 A1 4/2010 Davis and Transcutol on ibuprofen, Journal of Drug Delivery Science and 2010, 0125060 A1 5, 2010 RaZZak et al. Technology, vol. 21, No. 5 Sep. 2011 XP009 168551. 2011/O142945 A1 6, 2011 Chen et al. Hesson Chung, et al., Oil Components Modulate Physical Charac 2011/O195993 A1 8/2011 Masson et al. teristics and Function of the Natural Oil Emulsions as Drug or Gene 2012fO270845 A1 10, 2012 Bannister et al. Delivery System, Journal of Controlled Release 71:339-350 (2001). 2012fO270899 A1 10, 2012 Bannister et al. List et al., Hydrogenation of Soybean Oil Triglycerides: Effect of 2013, O156853 A1 6/2013 Zhang et al. Pressure on Selectivity. JAOCS (2000), vol. 77, pp. 311-314. Nickitas-Etienne, PCT International Preliminary Report on Patent FOREIGN PATENT DOCUMENTS ability, PCT/GB2011/050 189, pp. 11 (Aug. 7, 2012). Nickitas-Etienne, PCT International Preliminary Report on Patent CN 102.793628 A 11, 2012 ability, PCT/GB2011/052115, pp. 8 (Apr. 30, 2013). EP 306060 A2 3, 1989 PCT International Search Report and the Written Opinion of the EP 0521.344 A2 1/1993 Internation Searching Authority PCT/EP2014/050627. FR 2810243 A1 * 12/2001 PCT International Search Report and the Written Opinion of the SE 2315 A 3. Internation Searching Authority PCT/EP2014/050628. JP 6009381 3, 1992 PCT International Search Report and the Written Opinion of the JP 2008143807 12/2006 Internation Searching Authority PCT/EP2014/050637. JP 2009 155282 T 2009 Schule, PCT International Search Report & Written Opinion, WO 92.09272 A1 6, 1992 PCTGB2012050241, pp. 24 (Jul 13, 2012). WO 95/11039 A1 4f1995 Schule, PCT International Search Report & Written Opinion, WO 97.03655 A1 2, 1997 PCTGB2012050242, pp. 12 (Jan. 22, 2013). WO 98.25595 A1 6, 1998 Strickley, Solubilizing Excipients in Oral and Inkectable Formula WO OOf 27372 A1 5.2000 tions Pharaceutical (2004), vol. 21, pp. 21, pp. 201-230. WO OO57859 A1 5, 2000 Wolfgang Grebe, et al., A Multicenter, Randomized, Double-Blind, WO OOf 67728 A2 11/2000 Double-Dummy, Placebo- and Active-Controlled, Parallel-Group W. oo:: A. 3.399 Comparison of Diclofenac-K and Ibuprofen for the Treatment of WO O3,O13566 A1 2, 2003 Adults with Influenza-like Symptoms, Clinical Therapeutics 25(2): WO 2004/082.588 A2 9, 2004 444-459 (2003). WO 2005/009436 A1 2, 2005 Vane JR et al., Mechanism of action of anti-inflammatory drugs, Int WO 2006/099325 A2 9, 2006 J Tissue React. 1998;20(1):3-15, abstract. WO 20060968.06 A2 9, 2006 WO 2008/070950 A1 6, 2008 * cited by examiner U.S. Patent Apr. 12, 2016 Sheet 1 of 10 US 9,308,213 B2 Ibuprofen 10 m W 25 50 35 40 45 50 55 60 65 70 75 80 85 90 95 100 Temperature (C) FIG. 1A Gelucire 45/01 10 m W 25 30 35 40 45 50 55 60 65 70 Temperature (C) FIG. 1B U.S. Patent Apr. 12, 2016 Sheet 2 of 10 US 9,308,213 B2 Vehicle LA 5-61 2m W 25 50 35 40 45 50 55 60 65 70 75 80 Temperature (C) FIG. 1C Ibuprofen LA 35-1 25 30 35 40 45 50 55 60 65 70 75 80 85 90 95 100 Temperature (C) FIG. 1D U.S. Patent Apr. 12, 2016 Sheet 3 of 10 US 9,308,213 B2 |buprofen LA 35-2 25 50 35 40 45 50 55 60 65 70 75 80 85 90 95 100 Temperoture (C) FIG. 1E Ibuprofen LA 55-3 25 30 35 40 45 50 55 60 65 70 75 80 85 90 95 100 Temperature (C) FIG. 1 F U.S. Patent Apr. 12, 2016 Sheet 4 of 10 US 9,308,213 B2 Ibuprofen LA 3-51 2 mW 25 30 35 40 45 50 55 60 65 70 75 80 85 90 95 100 Temperature (C) FIG. 1G |buprofen LA 3-57 25 30 35 40 45 50 55 60 65 70 75 80 85 90 95 100 Temperature (C) FIG.
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