(12) United States Patent (10) Patent No.: US 9,358,295 B2 Tygesen Et Al

(12) United States Patent (10) Patent No.: US 9,358,295 B2 Tygesen Et Al

US009358295R2 (12) United States Patent (10) Patent No.: US 9,358,295 B2 Tygesen et al. (45) Date of Patent: *Jun. 7, 2016 (54) IMMEDIATE RELEASE COMPOSITION (56) References Cited RESISTANT TO ABUSEBY INTAKE OF ALCOHOL U.S. PATENT DOCUMENTS 2,685,553 A 8, 1954 Carroll et al. (71) Applicant: Egalet Ltd., London (GB) 3,835,221 A 9, 1974 Fulberth et al. 3,957,523 A 5, 1976 Ohno et al. (72) Inventors: Peter Holm Tygesen, Smoerum (DK), 4,330,3384,034,758 A 7,5, 19821977 TheeuwesBanker Jan Martin Oevergaard, Frederikssund 4.389,393 A 6, 1983 Schor et al. (DK); Joakim Oestman, Lomma (SE) 4.404,183 A 9, 1983 Kawata et al. 4,449,983 A 5/1984 Cortese et al. 4,503,067 A 3, 1985 Wiedemann et al. (73) Assignee: EGALET LTD., London (GB) 4,686,212 A 8, 1987 Ducatman et al. 4,824,675 A 4/1989 Wong et al. (*) Notice: Subject to any disclaimer, the term of this is: A 6. 3. Esthetricklet al. al. past list: sited under 35 4,892,742 A 1/1990 Shah M YW- 4,898,733. A 2f1990 De Prince et al. This patent is Subject to a terminal disis- 5,068,1125,019,396 A 1 5/19911/1991 SamejimaAyer et al. et al. claimer. 5,082,655 A 1/1992 Snipes et al. 5,102,668 A 4, 1992 Eichel et al. 5,213,808 A 5/1993 Bar-Shalom et al. (21) Appl. No.: 14/656,016 5,266,331 A 11/1993 Oshlack et al. 5,281,420 A 1/1994 Kelmet al. (22) Filed: Mar 12, 2015 5,352.455 A 10, 1994 Robertson 5,411,745 A 5/1995 Oshlack et al. (65) Prior Publication Data 5.432.1335.419,917. A 6/19955/1995 ConteChen et et al. al. 5,460,826 A 10, 1995 Merrill et al. US 2015/0313997 A1 Nov. 5, 2015 5,478,577 A 12/1995 Sackler et al. 5,508,042 A 4/1996 OShlack et al. 5,520,931 A 5/1996 Persson et al. Related U.S. Application Data 5,529,787 A 6/1996 Merrill et al. 5,549,912 A 8, 1996 OShlack et al. (63) Continuation of application No. 12/701.248, filed on 5,593,695 A 1/1997 Merrill et al. Feb. 5, 2010, now Pat. No. 9,005.660 5,609,885. A 3/1997 Rivera et al. s s vs.- ... -- w w / w w 5,614,218 A 3, 1997 Olsson et al. (60) Provisional application No. 61/150,577, filed on Feb. 5,618,560 A 4/1997 Bar-Shalom et al. 6, 2009, provisional application No. 61/151.491, filed 5,656,291 A 8, 1997 Olsson et al. on Feb. 10, 2009. (Continued) (30) Foreign Application Priority Data FOREIGN PATENT DOCUMENTS EP O435,726 8, 1991 Feb. 6, 2009 (DK) ................................. 2009 OO190 EP O493513 7, 1992 (Continued) (51) Int. Cl. A6 IK9/46 (2006.01) OTHER PUBLICATIONS A6 IK 9/16 (2006.01) U.S. Appl. No. 13/900,933, filed Aug. 25, 2006, Purdue Pharma C. A6 IK3I/44 (2006.01) Bravo et al., “In-vitro studies of diclofenac sodium controlled-release A6 IK3I/6 (2006.01) from biopolymeric hydrophilic matrices.” J. Pharmaceutical Sci A6 IK3I/485 (2006.01) ence, vol. 5, No. 3, pp. 213-219 (2002). A6 IK3I/67 (2006.01) The Condensed Chemical Dictionary, “mixture.” 9th edition, p. 584 A6 IK 9/28 (2006.01) (1977). A6 IK9/20 (2006.01) Giunchedi et al "Hydrophilic matrices for the extended release of a A6 IK 47/10 (2006.01) model drug exhibiting pH-dependent solubility.” International Jour A6 IK 47/02 (2006.01) nal of Pharmaceutics, vol. 85, pp. 141-147 (1992). A6 IK 47/12 (2006.01) (Continued) (52) U.S. Cl. CPC ............... A61K 47/10 (2013.01); A61 K9/0007 Primary Examiner — Shirley V Gembeh (2013.01); A61 K9/2031 (2013.01); A61 K (74) Attorney, Agent, or Firm — Foley & Lardner LLP 9/2866 (2013.01); A61 K9/2893 (2013.01); A61 K3I/I67 (2013.01); A61 K3I/485 (57) ABSTRACT (2013.01); A61 K47/02 (2013.01); A61 K47/12 The present invention provides immediate release pharma (2013.01); A61 K9/2095 (2013.01) ceutical compositions for oral administration that are resis (58) Field of Classification Search tant to abuse by intake of alcohol. USPC ........................... 424/466,495; 514/282, 629 See application file for complete search history. 19 Claims, 23 Drawing Sheets US 9,358,295 B2 Page 2 (56) References Cited 7,510,727 B2 3, 2009 Oshlack et al. 7,514,100 B2 4/2009 Oshlack et al. 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