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(12) United States Patent (10) Patent No.: US 9,642,809 B2 Hemmingsen Et Al

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(12) United States Patent (10) Patent No.: US 9,642,809 B2 Hemmingsen Et Al USOO9642809B2 (12) United States Patent (10) Patent No.: US 9,642,809 B2 Hemmingsen et al. (45) Date of Patent: *May 9, 2017 (54) CONTROLLED RELEASE 4.389,393 A 6, 1983 Schor et al. PHARMACEUTICAL COMPOSITIONS FOR 4.404,183 A 9, 1983 Kawata et al. 4,449,983 A 5/1984 Cortese et al. PROLONGED EFFECT 4,503,067 A 3, 1985 Wiedemann et al. 4,686,212 A 8, 1987 Ducatman et al. (71) Applicant: Egalet Ltd., London (GB) 4,769,372 A 9, 1988 Kreek 4,824,675 A 4/1989 Wong et al. (72) Inventors: Pernille Hoyrup Hemmingsen, 4,844,984 A 7, 1989 Eckenhoff et al. Bagsvaerd (DK); Anders Vagno 4,873,080 A 10, 1989 Bricklet al. 4,892,742 A 1, 1990 Shah Pedersen, Virum (DK); Daniel 4,898,733. A 2f1990 De Prince et al. Bar-Shalom, Kokkedal (DK) 5,019,396 A 5/1991 Ayer et al. 5,068,112 A 11/1991 Samejima et al. (73) Assignee: EGALET LTD., London (GB) (Continued) (*) Notice: Subject to any disclaimer, the term of this FOREIGN PATENT DOCUMENTS patent is extended or adjusted under 35 U.S.C. 154(b) by 0 days. EP O 435 T26 A2 7, 1991 EP O 908 181 4f1999 This patent is Subject to a terminal dis claimer. (Continued) (21) Appl. No.: 14/446,234 OTHER PUBLICATIONS Krogel et al (Pharmaceutical Research, 1998, vol. 15, pp. 474 (22) Filed: Jul. 29, 2014 481).* U.S. Appl. No. 13/803,132, filed Aug. 25, 2006, Purdue Pharma C. (65) Prior Publication Data U.S. Appl. No. 13/900,933, filed Aug. 25, 2006, Purdue Pharma C. U.S. Appl. No. 13/949.966, filed Dec. 18, 2002, Pain Therapeutics US 2015/OO24O48 A1 Jan. 22, 2015 A. International Search Report issued on Jul. 8, 2008 in application No. Related U.S. Application Data PCT/DK2008/000016 (corresponding to U.S. Pat. No. 8,603,526). International Search Report issued on Oct. 20, 2009 in application (63) Continuation of application No. 12/602.953, filed as No. PCTDK2009/000192. application No. PCT/EP2008/056910 on Jun. 4, 2008, International Search Report issued on Apr. 21, 2010 in application now Pat. No. 8,821,928. No. PCT/EP2010/00728 (corresponding to US 2010/0204259). International Search Report issued on May 18, 2010 in application No. PCT/DK2010/00019 (corresponding to U.S. Pat. No. (60) Provisional application No. 60/941,848, filed on Jun. 8,603,526). 4, 2007. (Continued) (30) Foreign Application Priority Data Primary Examiner — Mark V Stevens (74) Attorney, Agent, or Firm — Foley & Lardner LLP Jun. 4, 2007 (DK) ................................. 2007 OO816 (57) ABSTRACT (51) Int. Cl. Layered pharmaceutical composition Suitable for oral use in A6 IK 9/20 (2006.01) the treatment of diseases where absorption takes place over A6 IK 9/28 (2006.01) a large part of the gastrointestinal tract. The composition A6 IK3I/I67 (2006.01) comprising A) a Solid inner layer comprising i) an active Substance, and A6 IK 3/485 (2006.01) ii) one or more disintegrants/exploding agents, one of more A 6LX 3/573 (2006.01) effervescent agents or a mixture thereof. A6 IK 9/24 (2006.01) The solid inner layer being sandwiched between two outer (52) U.S. Cl. layers B1) and B2), each outer layer comprising CPC ............ A61K 9/2086 (2013.01); A61K 9/209 iii) a substantially water soluble and/or crystalline polymer (2013.01); A61 K9/2072 (2013.01); A61 K or a mixture of substantially water soluble and/or crys 9/2853 (2013.01); A61K 9/2866 (2013.01); talline polymers, the polymer being a polyglycol in the A61K 31/167 (2013.01); A61K 31/485 form of one of a) a homopolymer having a MW of at least (2013.01); A61 K3I/573 (2013.01) about 100,000 daltons, and b) a copolymer having a MW (58) Field of Classification Search of at least about 2,000 daltons, or a mixture thereof, and CPC ..... A61 K9/2086; A61 K9/2072: A61 K9/209 iv) an active Substance, which is the same as in said solid See application file for complete search history. inner layer A), and layer A being different from layer B. the layered composition being coated with a coating C) that (56) References Cited has at least one opening exposing at least one Surface of said outer layer, the coating being Substantially insoluble in and U.S. PATENT DOCUMENTS impermeable to fluids and comprising a polymer, and the composition having a cylindrical form optionally with one 2,685,553 A 3, 1951 Carroll et al. or more tapered ends, wherein the ratio between the surface 3,835,221 A 9, 1974 Fulberth et al. area of one end surface of the cylinder and the length of the 3,957,523 A 5, 1976 Ohno et al. 4,034,758 A 7, 1977 Theeuwes cylinder is in a range of from 0.02 to 45 mm. 4,330,338 A 5, 1982 Banker 27 Claims, 24 Drawing Sheets US 9,642.809 B2 Page 2 (56) References Cited 6,733,783 B2 5, 2004 OShlack et al. 6,757,558 B2 6/2004 Lange et al. U.S. PATENT DOCUMENTS 6,787,156 B1 9/2004 Bar-Shalom 6,800,668 B1 10/2004 Odidi et al. 5,102,668 A 4, 1992 Eichel et al. 6,837,696 B2 1/2005 Sowden et al. 5,213,808 A * 5/1993 Bar-Shalom ......... A61K 9, 2086 6,852,337 B2 2/2005 Gabel et al. 424/473 6,960,357 B2 11/2005 Chopra 5. A 6 CE." 7,063,864 B1 6/2006 Marechal et al. 5,352.455. A 10, 1994 Robertson 7,090,867 B2 8/2006 Odidi et al. 541745 A 5, 1995 Oshlack et al. 7,144,587 B2 12/2006 O'Shlack et al. 5.432.133 A 6, 1995 Conte et al. 7.201.920 B2 4/2007 Kumar et al. 5,460.826 A 10/1995 Merrillet al. 7,270,831 B2 9/2007 Oshlack et al. 5,478,577 A 12/1995 Sackler et al. 7,332,182 B2 22008 Sackler 5,508,042 A 4, 1996 Oshlack et al. 7,399.488 B2 7/2008 Hirsh et al. 5,520,931 A 5, 1996 Persson et al. 7,419,686 B2 9/2008 Kaiko et al. 5,549,912 A 8/1996 Oshlack et al. 7,476,402 B2 1/2009 Kumar et al. 5,593,695 A 1/1997 Merrill et al. 7,510,726 B2 3/2009 Kumar et al. 5,609,885. A 3, 1997 Rivera et al. 7,510,727 B2 3/2009 Oshlack et al. 5,618,560 A 4, 1997 Bar Shalom et al. 7,666,337 B2 2/2010 Yang et al. 5,656,291. A 8/1997 Olsson et al. 7,749,542 B2 7.2010 Kaiko et al. 5,656.295 A 8/1997 Oshlack et al. 7,771,707 B2 8/2010 Hirsh et al. 5,667,805. A 9, 1997 Merrill et al. 7,776.3 14 B2 8/2010 Bartholomaus et al. 5,672360 A 9, 1997 Sackler et all 7,790,215 B2 9/2010 Sackler et al. 5,741.524. A 4/1998 Staniforth et al. 7,842,307 B2 11/2010 Oshlack et al. 5,866,164 A 2/1999 Kuczynski et al. 7,883,722 B2 2/2011 Bar-Shalom 5,869,097 A 2/1999 Wong et al. 7,883,772 B2 2/2011 Pourdeyhimi et al. 5,879,705. A 3/1999 Heafield et al. 7,897,080 B2 3/2011 Yang et al. 591431 A 6, 1999 Merrill et al. 7,943,174 B2 5/2011 Oshlack et al. 5.948,787 A 9/1999 Merrilletal. 7968,120 B2 62011 Li et al. 5,952.005 A 9, 1999 Olsson et al. 7.972,624 B2 7/2011 Li et al. 5,968,551- - 4 A 10/1999 Oshlack et al. 7.981,439 B2 7/2011f Kumarkl et al. 6,046, 177 A 4/2000 Stella et al. 8,017,148 B2 9/2011 Sackler 6,077.533. A 6/2000 Oshlack et al. 8,029,822 B2 10/2011 Faour et al. 6,077,538 A 6, 2000 Merrill et al. 8,075,872 B2 12/2011 Arkenau-Marie et al. 6,103,261 A 8/2000 Chasin et al. 8, 101,630 B2 1/2012 Kumar et al. 6.143,328 A 11/2000 Heafield et all 8, 114,383 B2 2/2012 Bartholomaus et al. 683,778 B1 2/2001 Conte et al. 8,114,384 B2 2/2012 Arkenau et al. 6,245,351 B1 6/2001 Nara et al. 8,142,811 B2 3/2012 Oshlack et al. 6.245,357 B1 6/2001 Edgren et al. 8, 147,870 B2 4/2012 Yum et al. 6,267,981 B1 7/2001 Okamoto et al. 8,153,152 B2 4/2012 Yum et al. 6,277.384 B1 8, 2001 Kaiko et al. 8,173,152 B2 5/2012 Crowley et al. 6,284.274 B1 9/2001 Merrill et al. 8, 182,836 B2 5/2012 Mehta 6 294 195 B1 9, 2001 Oshlack et al. 8, 192,722 B2 6, 2012 Arkenau-Maric et al. 6,348.216 Bf 2.2002 Kushlaeal 8,231,898 B2 7/2012 Oshlack et al. 6,375,957 B1 4/2002 Kaiko et al. 8,246,986 B2 8/2012 Cruz et al.
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