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(12) United States Patent (10) Patent No.: US 8,414.914 B2 Bromley Et Al

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(12) United States Patent (10) Patent No.: US 8,414.914 B2 Bromley Et Al USOO841.4914B2 (12) United States Patent (10) Patent No.: US 8,414.914 B2 Bromley et al. (45) Date of Patent: *Apr. 9, 2013 (54) COMPOSITIONS FOR MIUCOSAL DELVERY (56) References Cited OFAGENTS U.S. PATENT DOCUMENTS (75) Inventors: Philip James Bromley, Fullerton, CA 4,740,365 A 4, 1988 Yukimatsu et al. ........... 424/435 (US); Lee Nickols Huang, Diamond 4,889,720 A 12, 1989 Konishi et al. ......... ... 424/447 4,900,552 A 2f1990 Sanvordeker et all ... 424/422 Bar, CA (US) 4,921,706 A 5/1990 Roberts et al. ..... ... 424/450 5,033,252 A 7/1991 Carter ............................. 534/25 (73) Assignee: Virun, Inc., Walnut, CA (US) 5,052,558 A 10, 1991 Carter ..... ... 206,439 5,154,924 A 10, 1992 Friden ............ 424,179.1 (*) Notice: Subject to any disclaimer, the term of this 5,178,878 A 1/1993 Wehling et al. ............... 424/466 5, 182,107 A 1/1993 Friden ........................ 424,85.91 patent is extended or adjusted under 35 5,234,957 A 8, 1993 Mantelle et al. U.S.C. 154(b) by 0 days. 5,298,246 A 3, 1994 Yano et al. 5,323,907 A 6/1994 Kalvelage ..................... 206,531 This patent is Subject to a terminal dis 5,527,527 A 6/1996 Friden ..... ... 424,178.1 claimer. (Continued) (21) Appl. No.: 13/507,928 FOREIGN PATENT DOCUMENTS CA 2229286 8, 1999 (22) Filed: Aug. 6, 2012 WO WO 2006/0098.25 1, 2006 (65) Prior Publication Data (Continued) US 2012/03O8644 A1 Dec. 6, 2012 OTHER PUBLICATIONS U.S. Appl. No. 60/527,962, filed Dec. 8, 2003, Masters et al. Related U.S. Application Data (Continued) (63) Continuation of application No. 12/930,978, filed on Primary Examiner — Anand Desai Jan. 20, 2011, now Pat. No. 8,252,323, which is a Assistant Examiner — Melissa Mercier continuation of application No. 1 1/155,262, filed on (74) Attorney, Agent, or Firm — McKenna Long & Aldridge Jun. 16, 2005, now Pat. No. 7,906, 140. LLP; Stephanie Seidman (60) Provisional application No. 60/580,877, filed on Jun. (57) ABSTRACT 17, 2004. Compositions and methods for mucosal delivery of agents are provided. The compositions are intended for administration (51) Int. C. to mucosal Surface, Such as oral, gastrointestinal and nasal A6 IK38/00 (2006.01) mucosa. The compositions provided contain one or more (52) U.S. C. mucoadhesive proteins and an agent to be delivered. Methods USPC ............................................... 424/450; 514/1 for delivery of agents using the compositions provided herein (58) Field of Classification Search ........................ None are also provided. See application file for complete search history. 24 Claims, 1 Drawing Sheet Oral insulin - Human G lucose Levels 250 200 10 O 50 i i Time (hrs) US 8,414.914 B2 Page 2 U.S. PATENT DOCUMENTS Ectotropin-6TM Website Printout, found at: www.ibe-technology. 5,620,708 A 4, 1997 Amkraut et al. .............. 424/491 com/ectotropin.htm retrieved on Jan. 20, 2006). 5,672,683 A 9, 1997 Friden et al. ... 530/350 Fehniger et al., “Exploring the context of the lung proteome within 5,702,727 A 12, 1997 Amkraut et al. ... 424/491 the airway mucosa following allergen challenge. J Proteome Res. 5,744, 155 A 4, 1998 Friedman et al. .. ... 424/434 3(2):307-320 (2004). 5,833,988 A 11/1998 Friden ......... 424,178.1 Good, R., "Surface free energy of solids and liquids: Thermodynam 5,977,307 A 11/1999 Friden et al. ... 530/350 5,993,846 A 11/1999 Friedman et al. .. 424/434 ics, molecular forces, and structure.” Journal of Colloid and Interface 6,071.535 A 6/2000 Hayward et al. ... ... 424/450 Science. 59(3):398-419 (1977). 6,329,508 B1 12/2001 Friden ......... 530,387.3 Gu et al., “Binding of acrylic polymers to mucin/epithelial Surfaces: 6,383,513 B1 5, 2002 Watts et al. ... 424/450 structure-property relationships.” Critical Reviews in Therapeutic 6.426,362 B1 7/2002 Miller et al. 514,458 Drug Carrier Systems 5(1): 21-67 (1988). 6,475,511 B2 11/2002 Gohlke et al. ... 424/441 Handbook of Pharmaceutical Excipients, “Lecithin.” Published by 6,552,024 B1 4/2003 Chen et al. ............... 514,252.16 American Pharmaceutical Association: Washington DC and the Phar 6,638,521 B2 10/2003 Dobrozsi et al. .............. 424/434 6,749,863 B1 6/2004 Chang et al. ... ... 424/450 maceutical Society of Great Britain: London, p. 165 (1986). 6,905,688 B2 6, 2005 Rosen et al. 424,192.1 HexaTropin-6TM Website Printout, found at: www.ibe-technology. 6,926,898 B2 8, 2005 Rosen et al. 424,192.1 com/hexatropin.htm retrieved on Jan. 20, 2006). 6,946,134 B1 9, 2005 Rosen et al. 424,192.1 Lehr et al., “Visualization studies of the mucoadhesive interface.” 6,994,857 B2 2/2006 Rosen et al. 424,192.1 Journal of Controlled Release, 18:249-260 (1992). 7,179,484 B2 2/2007 Singh ............. ... 424/450 Nogrady, M., Medicinal Chemistry a Biochemical Approach, Oxford 7,906,140 B2 * 3/2011 Bromley et al. 424/450 University Press, New York, pp. 388-392 (1985). 8,252.323 B2 * 8/2012 Bromley et al. .............. 424/450 8,282,977 B2 10/2012 Bromley ......................... 426,72 Oratropin-1TM Website Printout, foundat: www.ibe-technology.com/ 2003/017.0311 A1 9, 2003 Russell .... 424/489 oratropin.htm retrieved on Jan. 20, 2006). 2003/0171259 A1 9/2003 Modi et al. ........................ 514/2 Peppas, N. and P. Burl. "Surface, interfacial and molecular aspects of 2003/0171267 A1 9, 2003 Rosen et al. ... 514/12 polymer bioadhesion on soft tissues,” Journal of Controlled Release, 2003/0219472 A1 11, 2003 Pauletti et al. 424/449 2:257-275 (1985). 2003/0221201 A1 11/2003 Prior et al. ........................ 800.7 Press Release: “OmegaH2O.R. clear shelf stable Omega-3, CoQ10 2003/0226155 Al 12/2003 Sadeghi et al. ................... 800.7 2004/0010134 A1 1/2004 Rosen et al. 536,235 and other nonpolar compounds U.S. Appl. No. 12/383.244 approved 2004/OO23334 A1 2/2004 Prior ............................ 435/69.7 in Europe and Notice of Allowance in U.S.” Published on Jun. 4. 2004/0037809 A1 2/2004 Quay et al. .................... 424,856 2012 online Retrieved from:<URL:pr.com/press-relcase/4175994 2004/OO77540 A1 4/2004 Quay .......... ... 514/12 pages. 2005, 0196440 A1 9, 2005 Masters et al. 424/464 Press Release: "VIRUN patent granted mucosal adhesive penetrating 2005/O197495 A1 9, 2005 Naidu ............ ... 530/400 technology delivering naive compounds and peptides orally.” Pub 2005/028.1772 A1 12/2005 Bromley et al. 424.70.14 lished on Mar. 23, 2011 online Retrieved from:<URL: pricom/ 2006, OO84794 A1 4/2006 Rosen et al. ... ... 530,363 press-release/3079872 pages). 2006/0093594 A1 5, 2006 Naidu ...... 424/9345 2009/0297491 A1 12/2009 Bromley .. 424/94.1 Press Release: "VIRUNR) closes $2.1 million series—A funding to 2009/0297665 A1 12/2009 Bromley .. ... 426,72 bolster innovation and world-wide expansion.” Published on Aug. 2, 2009/0317532 A1 12/2009 Bromley ... 426,590 2012 online Retrieved from:<URL:pr.com/press-release/4315794 2010.0041622 A1 2/2010 Bromley et al. 514/52 pages. 2011/01171.84 A1 5/2011 Bromley ... 424/450 Ryan et al. “Immunomodulators and delivery systems for vaccination 2011/0236364 A1 9/2011 Bromley ...................... 424/94.1 by mucosal routes' Trends in Biotechnology, 293-304 (2001). 2012fOO16026 A1 1/2012 Bromley ....................... 514,560 Simoes et al., “Mechanisms of gene transfer mediated by lipoplexes FOREIGN PATENT DOCUMENTS associated with targeting ligands or pH-sensitive peptides.” Gene Ther. (11): 1798-1807 (1999). WO WO 2009,11715.1 9, 2009 Smart et al., “An in-vitro investigation of mucosa-adhesive materials WO WO 2009,117152 9, 2009 WO WO 2010/OO8475 1, 2010 for use in controlled drug delivery,” J. Pharm. Pharmacol. 36:295-299 WO WO 2010/O19255 2, 2010 (1984). WO WO 2011 119228 9, 2011 Smart et al., “In vitro techiniques for measuring mucoadhesion.” J. Pharm. Pharmacol. 34:70P (1982). OTHER PUBLICATIONS Tabor et al., " Surface forces and surface interactions' Journal of Colloid and Interface Science. 58(1):2-13 (1977). U.S. Appl. No. 60/887,754, filed Feb. 1, 2007, Borowy-Borowski et Virun home Webpage found at www.virun.com accessed on Mar. al. 24, 2011), 59 pages. Almeida et al., “Nasal delivery of vaccines,” Journal of Drug Target Virun Improving Life Through Safe & Effective Oral Delivery found ing, 3:456-467 (1996). at: www.sldeshare.net/virun?virun-improving-life-through-safe-ef Alonso et al., “Biodegradable nanostructures as carriers for fective-oral-delivery accessed on May 11, 2009), 15 pages. transmucosal delivery.” Presented at the 226th ACS National Meet Virun Intricate Science; found at www.slideshare.net/virun?virun ing, New York, NY, Sep. 8, 2003. Abstract. 1 page. intricate-science accessed May 25, 2011, 22 pages. Ansel, H., Introduction to Pharmaceutical Dosage Forms, Fourth Vogelson. C., “Advances in drug delivery systems. Modern Drug Edition, Philadelphia: Lea& Febiger, p. 126 (1985). Discovery, 4(4):59-50.52 (2001). Budavari, et al.(Eds.) The Merck Index, 12th Edition, Whitehouse Wadell, C. "Nasal drug delivery—in vitro studies on factors influ Station, N.J.Merck & Co., pp. THER-1 to THER-28, (1996). encing permeability and implications on absorption.” Acta Drug Delivery Technology, Alkaline Acidic Triggering Effect pam Universitatis Upsaliensis. Comprehensive Summaries of Uppsala phlet, Archimedes Laboratories, Inc., City of Industry, CA, 2 pages, Dissertations from the Faculty of Pharmacy 278.
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