USOO9005660B2 (12) United States Patent (10) Patent No.: US 9,005,660 B2 Tygesen et al. (45) Date of Patent: Apr. 14, 2015 (54) IMMEDIATE RELEASE COMPOSITION 4,873,080 A 10, 1989 Bricklet al. RESISTANT TO ABUSEBY INTAKE OF 4,892,742 A 1, 1990 Shah 4,898,733. A 2f1990 DePrince et al. ALCOHOL 5,019,396 A 5/1991 Ayer et al. 5,068,112 A 11/1991 Samejima et al. (75) Inventors: Peter Holm Tygesen, Smoerum (DK); 5,082,655 A 1/1992 Snipes et al. Jan Martin Oevergaard, Frederikssund 5,102,668 A 4, 1992 Eichel et al. 5,213,808 A 5/1993 Bar Shalom et al. (DK); Joakim Oestman, Lomma (SE) 5,266,331 A 11/1993 Oshlack et al. 5,281,420 A 1/1994 Kelmet al. (73) Assignee: Egalet Ltd., London (GB) 5,352.455 A 10, 1994 Robertson 5,411,745 A 5/1995 Oshlack et al. (*) Notice: Subject to any disclaimer, the term of this 5,419,917 A 5/1995 Chen et al. patent is extended or adjusted under 35 5,422,123 A 6/1995 Conte et al. U.S.C. 154(b) by 473 days. 5,460,826 A 10, 1995 Merrill et al. 5,478,577 A 12/1995 Sackler et al. 5,508,042 A 4/1996 OShlack et al. (21) Appl. No.: 12/701.248 5,520,931 A 5/1996 Persson et al. 5,529,787 A 6/1996 Merrill et al. (22) Filed: Feb. 5, 2010 5,549,912 A 8, 1996 OShlack et al. 5,593,695 A 1/1997 Merrill et al. (65) Prior Publication Data 5,609,885 A 3, 1997 Rivera et al. 5,614,218 A 3, 1997 Olsson et al. US 2010/0204259 A1 Aug. 12, 2010 5,618,560 A 4/1997 Bar-Shalom et al. 5,656,291 A 8, 1997 Olsson et al. 5,656.295 A 8, 1997 OShlack et al. Related U.S. Application Data 5,667,805 A 9, 1997 Merrill et al. 5,672,360 A 9, 1997 Sackler et al. (60) Provisional application No. 61/151,491, filed on Feb. 5,741,524 A 4/1998 Staniforth et al. 10, 2009, provisional application No. 61/150,577, (Continued) filed on Feb. 6, 2009. FOREIGN PATENT DOCUMENTS (30) Foreign Application Priority Data DE 202006O14131 1, 2007 Feb. 6, 2009 (DK) ................................. 2009 OO190 EP O435,726 8, 1991 (Continued) (51) Int. Cl. A6 IK9/46 (2006.01) OTHER PUBLICATIONS A6 IK 9/16 (2006.01) A6 IK3I/44 (2006.01) Notification of Transmittal of the International Search Report and the A6 IK3I/6 (2006.01) Written Opinion of the International Searching Authority issued Jul. A6 IK3I/485 (2006.01) 8, 2008 in International Application No. PCT/DK2008/000016. A6 IK3I/67 (2006.01) Preliminary Amendment filed Jul. 13, 2009 in co-pending U.S. Appl. A6 IK 9/28 (2006.01) No. 12/523,045. Notification of Transmittal of the International Search Report and the A6 IK9/20 (2006.01) Written Opinion of the International Searching Authority issued Apr. (52) U.S. Cl. 21, 2010 in International Application No. PCT/EP2010/000728. CPC ............. A61 K9/0007 (2013.01); A61 K3I/485 Notification of Transmittal of the International Search Report and the (2013.01); A61 K3I/I67 (2013.01); A61 K Written Opinion of the International Searching Authority issued May 9/2893 (2013.01); A61 K9/2031 (2013.01); 28, 2010 in International Application No. PCT/DK2010/000019. A61 K9/2095 (2013.01); A61 K9/2866 Fischer, et al., “Nonmedical Use of Prescription Opioids: Furthering (2013.01) a Meaningful Research Agenda.” J. Pain. 9:6, 2008 490-493. (58) Field of Classification Search (Continued) USPC ........................... 424/466,495; 514/282, 629 See application file for complete search history. Primary Examiner — Shirley V Gembeh (74) Attorney, Agent, or Firm — Foley & Lardner LLP (56) References Cited U.S. PATENT DOCUMENTS (57) ABSTRACT The present invention relates to immediate release pharma 2,685,553 A 8, 1954 Carroll et al. ceutical compositions for oral administration that are resis 3,835,221 A 9, 1974 Fulberth et al. 3,957,523 A 5, 1976 Ohno et al. tant to abuse by intake of alcohol. In particular, this disclosure 4,034,758 A 7, 1977 Theeuwes provides immediate release pharmaceutical compositions 4,330,338 A 5, 1982 Banker comprising a polyglycol having a molecular weight of from 4.389,393 A 6, 1983 Schor et al. about 900 to about 17,000 daltons, a drug substance, one or 4.404,183 A 9, 1983 Kawata et al. more effervescent agents, and, optionally, one or more disin 4,449,983 A 5, 1984 Cortese et al. 4,503,067 A 3, 1985 Wiedemann et al. tegrants, such that the composition is formulated to be resis 4,686,212 A 8, 1987 Ducatman et al. tant to abuse by intake of alcohol. 4,824,675 A 4/1989 Wong et al. 4,844,984 A 7, 1989 Eckenhoffetal. 13 Claims, 23 Drawing Sheets US 9,005,660 B2 Page 2 (56) References Cited 7,771,707 B2 8, 2010 Hirsh et al. 7,776,314 B2 8/2010 Bartholomaus et al. U.S. PATENT DOCUMENTS 7,842,307 B2 11/2010 Oshlack et al. 7,846,476 B2 12/2010 Oshlack et al. 5,866,161 A 2f1999 Childers et al. 7,883,722 B2 2/2011 Bar-Shalom. 5,866,164 A 2/1999 Kuczynski et al. 7,883,772 B2 2/2011 Pourdeyhimi et al. 5,869,097 A 2/1999 Wong et al. 7,897,080 B2 3, 2011 Yang et al. 5,879,705 A 3, 1999 Heafield et al. 7,906,143 B1 3/2011 Odidi et al. 5,882,682 A 3, 1999 Rork et al. 7,943,174 B2 5, 2011 Oshlack et al. 5,914, 131 A 6, 1999 Merrill et al. 7968,120 B2 62011 Liet al. 5.948,787 A 9, 1999 Merrill et al. 7.972,624 B2 7/2011 Lietal. 5,952,005 A 9, 1999 Olsson et al. 7,981,439 B2 7/2011 Kumar et al. 5,968,551 A 10/1999 Oshlack et al. 8,017,148 B2 9/2011 Sackler 6,046,177 A 4/2000 Stella et al. 8,017,150 B2 9/2011 Yang et al. 6,066,339 A 5, 2000 Stark et al. 8,029,822 B2 10/2011 Faour et al. 6,077,533 A 6, 2000 OShlack et al. 8,075,872 B2 12/2011 Arkenau-Maric et al. 6,077,538 A 6, 2000 Merrill et al. 8, 101,630 B2 1/2012 Kumar et al. 6,103,261 A 8, 2000 Chasin et al. 8, 105,631 B2 1/2012 Kaiko et al. 6,117,453 A 9, 2000 Seth et al. 8, 114,383 B2 2/2012 Bartholomaus et al. 6,143,328 A 11/2000 Heafield et al. 8,114,384 B2 2/2012 Arkenau et al. 6,183,778 B1 2/2001 Conte et al. 8,133,507 B2 3/2012 Yum et al. 6.225.343 B1 5, 2001 Behlet al. 8,142,811 B2 3/2012 Oshlack et al. 6,245.351 B 62001 Nara et al. 8, 147,870 B2 4/2012 Yum et al. 6.245,357 B1 6/2001 Edgren et al. 8,153,152 B2 4/2012 Yum et al. 6,267,981 B1 7/2001 Okamoto et al. 8,168,217 B2 5/2012 Yum et al. 6,267,985 B1 7/2001 Chen et al. 8,173,152 B2 5/2012 Crowley et al. 6,277.384 B1 8/2001 Kaiko et al. 8, 182,836 B2 5/2012 Mehta 6,284.274 B1 9, 2001 Merrill et al. 8, 192,722 B2 6/2012 Arkenau-Maric et al. 6,294,195 B1 9, 2001 Oshlack et al. 8,231,898 B2 7/2012 Oshlack et al. 6,348.216 B1 2/2002 Kushla et al. 8,246,986 B2 8/2012 Cruz et al. 6,375,957 B1 4/2002 Kaiko et al. 8,309,060 B2 11/2012 Bartholomaus et al. 6,383,471 B1 5, 2002 Chen et al. 8.323,889 B2 12/2012 Arkenau-Maric et al. 6,395.299 B1 5/2002 Babich et al. 8,329.720 B1 12/2012 King et al. 6,399,096 B1 6, 2002 Miller et al. 8.337,888 B2 12/2012 Wright et al. 6.403.579 B1 6, 2002 Heller 8.338,444 B1 12/2012 King et al. 6.451848 B1 9/2002 Behlet al. 8,354,124 B2 1/2013 Yum et al. 6.458,772 B1 10/2002 Zhou et al. 8,361,499 B2 1/2013 Oshlack et al. 6,458,824 B1 10/2002 Iwata et al. 8,367,693 B1 2/2013 King et al. 6,475,494 B2 11/2002 Kaiko et al. 8,372.432 B2 2/2013 Han et al. 6,482.437 B2 11/2002 Debregeas et al. 8,377,453 B2 2/2013 Han et al. 6,488.962 B1 12/2002 Berner et al. 8,383,152 B2 2/2013 Janset al. 6,488.963 B1 12/2002 McGinity et al. 8,383,154 B2 2/2013 Bar-Shalom 6,491.945 B1 12/2002 Childers et al. 8,383,155 B2 2/2013 Bar-Shalom 6,517,866 B1 2/2003 Am Ende et al. 8,389,007 B2 3/2013 Wright et al.