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(12) United States Patent (10) Patent No.: US 8.445,023 B2 Guimberteau Et Al

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(12) United States Patent (10) Patent No.: US 8.445,023 B2 Guimberteau Et Al USOO8445,023B2 (12) United States Patent (10) Patent No.: US 8.445,023 B2 Guimberteau et al. (45) Date of Patent: May 21, 2013 (54) ANTI-MISUSE MICROPARTICULATE ORAL 6.264,983 B1 7/2001 Upadhyay PHARMACEUTICAL FORM 6,309.668 B1 10/2001 Bastin et al. 6,444,246 B1 9/2002 Popplewell et al. (75) Inventors: Florence Guimberteau, Montussan 6,566,560 B2 5, 2003 Travis (FR); Frederic Dargelas, Pessac (FR) (Continued) (73) Assignee: Flamel Technologies (FR) FOREIGN PATENT DOCUMENTS EP O198769 10, 1986 (*) Notice: Subject to any disclaimer, the term of this EP O7O9087 5, 1996 patent is extended or adjusted under 35 (Continued) U.S.C. 154(b) by 335 days. OTHER PUBLICATIONS (21) Appl. No.: 12/638,739 In the U.S. Patent and Trademark Office, Office Action in re: U.S. (22) Filed: Dec. 15, 2009 Appl. No. 1 1/651.577, dated Dec. 26, 2008, 22 pages. (65) Prior Publication Data (Continued) US 2010/0092.553 A1 Apr. 15, 2010 Primary Examiner — Paul Dickinson Related U.S. Application Data (74) Attorney, Agent, or Firm — Patton Boggs LLP (62) Division of application No. 1 1/439,432, filed on May 24, 2006. (57) ABSTRACT (60) Provisional application No. 60/735,182, filed on Nov. 10, 2005. The present invention relates to solid microparticulate oral pharmaceutical forms whose composition and structure make (30) Foreign Application Priority Data it possible to avoid misuse of the pharmaceutical active prin ciple (AP) they contain. Nov. 10, 2005 (FR) ...................................... O5 53437 The object of the present invention is to prevent solid oral (51) Int. Cl. drugs from being misappropriated for any use other than the A6 IK 9/16 (2006.01) therapeutic use(s) officially approved by the competent pub (52) U.S. Cl. lic health authorities. In other words, the object is to avoid the USPC .......................................................... 424/490 Voluntary or involuntary misuse of Solid oral drugs. (58) Field of Classification Search The invention relates to a solid oral pharmaceutical form None which is characterized in that it contains anti-misuse means, See application file for complete search history. in that at least part of the AP it comprises is contained in coated microparticles for modified release of the AP, and in (56) References Cited that the coated microparticles of AP have a coating layer (Ra) which assures the modified release of the AP and simulta U.S. PATENT DOCUMENTS neously imparts crushing resistance to the coated micropar 4,070,494 A 1/1978 Hoffmeister et al. ticles of AP so as to avoid misuse. 5,603,957 A * 2/1997 Burguiere et al. ............ 424/489 5,780,055 A 7, 1998 Habib et al. 6,248,363 B1 6, 2001 Patel et al. 31 Claims, 4 Drawing Sheets 120 -- EXAMPLE1 10 12 14 16 US 8,445,023 B2 Page 2 U.S. PATENT DOCUMENTS WO WO-2005, O79760 9, 2005 6,696,088 B2 2/2004 OShlack et al. WO WO-2006/056712 6, 2006 WO WO-2006/056713 6, 2006 2002.0068365 A1 6, 2002 Kuhrts WO WO-2006/089843 8, 2006 2003, OO68276 A1 4/2003 Hughes et al. WO WO-2006/125819 11, 2006 2003.0068371 A1 4/2003 Oshlack et al. WO WO-2006,133733 12/2006 2003.0068392 A1 4/2003 Sackler WO WO-2006,134018 12/2006 2003/0083286 A1 5/2003 Teng et al. 2003.01.18641 A1 6/2003 Maloney et al. .............. 424/465 OTHER PUBLICATIONS 2003/0224051 Al 12/2003 Finket al. 2004/0010984 A1 1/2004 Wright In the U.S. Patent and Trademark Office, Final Office Action in re: 2004/0022849 A1 2/2004 Castan et al. U.S. Appl. No. 1 1/651,577, dated Jul. 31, 2009, 8 pages. 2004/OO52731 A1 3, 2004 Hirsh et al. th d Trad k Off f Ar is r^ 2004.0053887 A1 3, 2004 Obae et al. In the U.S. Patent and Trademark Office, Office Action in re: U.S. 2004/0126428 A1 7/2004 Hughes et al. Appl. No. 1 1/651.577, dated Jan. 6, 2010, 7 pages. 2004/0208936 A1 10, 2004 Chorin et al. In the U.S. Patent and Trademark Office, Final Office Action in re: 2004/0228924 A1 11/2004 Oshlack et al. U.S. Appl. No. 1 1/651,577, dated Jul. 9, 2010, 8 pages. 2004/0234601 A1 1 1/2004 Legrand et al. In the U.S. Patent and Trademark Office, Office Action in re: U.S. 2005/0163856382.83. A1A 7/2005338 R.".Maloney et al.. 424,469 I ERN'EENU.S. Patentaen and TTrademark OUITIce,EAE Final UITIceO Action in re:re 2005, 018104.6 A1 8, 2005 Oshlack et al. U.S. Appl. No. 1 1/651,577, dated Apr. 29, 2011, 10 pages.Ar is r^ 2005/0214223 A1 9/2005 Bartholomaeus et al. In the U.S. Patent and Trademark Office, Office Action in re: U.S. 2005/0266078 A1 12, 2005 Jorda et al. Appl. No. 1 1/791,336, dated Jun. 23, 2010, 14 pageS. 2005/0281748 A1 12, 2005 Hirsh et al. In the U.S.U.S. Patentat anda TrademarkCa Office.ce, FinalFina. OfficeCACO Act 2007/0183980 A1 8/2007 Arkenau-Maric et al. U.S. Appl. No. 1 1/791,336, dated Dec. 8, 2010, 7 pages. 2007/0202049 A1 8, 2007 Guimberteau et al. In the U.S. Patent and Trademark Office, Requirement for Restric 2007/0224129 A1 9, 2007 Guimberteau et al. tion/Election in re: U.S. Appl. No. 1 1/651.577, dated Apr. 9, 2008, 7 2007/0264326 A1 11/2007 Guimberteau et al. pageS. 2008, OOO8659 A1 1/2008 Guimberteau et al. In the U.S. Patent and Trademark Office, Requirement for Restric 2008/0193540 Al 8, 2008 Soula et al. tion/Election in re: U.S. Appl. No. 1 1/791,336, dated Feb. 16, 2010, 2009/0041838 A1 2/2009 Guimberteau et al. 6 pages. FOREIGN PATENT DOCUMENTS In the U.S. Patent and Trademark Office, Office Action in re: U.S. Appl. No. 1 1/439.432, dated Dec. 7, 2012, 8 pages. F. 2.29 298. In the U.S. Patent and Trademark Office, Final Office Action in re: U.S. Appl. No. 1 1/439,432, dated Feb. 29, 2012, 10 pages. WOFR WO-01/086612837 100 2,9, 20012003 In the U.S. Patent and Trademark Office, Office Action in re: U.S. WO WO-03/013467 2, 2003 Appl. No. 1 1/439.432, dated Jul. 13, 2011, 6 pages. WO WO-03/013479 2, 2003 In the U.S. Patent and Trademark Office, Final Office Action in re: WO WO-03/O13538 2, 2003 U.S. Appl. No. 1 1/439,432, dated Dec. 22, 2009, 12 pages. WO WO-O3,O3O878 4/2003 In the U.S. Patent and Trademark Office, Office Action in re: U.S. WO WO-O3,O77888 9, 2003 Appl. No. 1 1/439.432, dated Jan. 30, 3009, 21 pages. WO WO-03/082204 10, 2003 In the U.S. Patent and Trademark Office, Requirement for Restric WO WO-03/103.538 12/2003 tion/Election in re: U.S. Appl. No. 1 1/439,432, dated Apr. 29, 2008, WO WO-2004/004693 1, 2004 13 pages. W. W858; 8. 3.39. Remington's The Science and Practice of Pharmacy, 1995, 19th WO WO 2004.05633 4/2004 edition, Mack Publishing Co., Pennsylvania, USA. WO Wo.3064/O37259 5, 2004 New Pharmaceutical Forms: Technological, Biopharmaceutical and WO WO-2004/052346 6, 2004 Medical Aspects, Buri, Puisieux, Doelker and Benoit 1985, pp. 175 WO WO-2004/054542 T 2004 227. WO WO-2005/O16313 2, 2005 * cited b WO WO-2005, 016314 2, 2005 cited by examiner U.S. Patent May 21, 2013 Sheet 1 of 4 US 8.445,023 B2 120 & 60 -- EXAMPLE1 O -H EXAMPLE ... --O . EXAMPLE2(a) ... -o- . EXAMPLE 2 (b) - - -o- ... EXAMPLE 2 (c) ... -A. EXAMPLE2(d) U.S. Patent May 21, 2013 Sheet 2 of 4 US 8.445,023 B2 (A): Observation with the naked eye (B): Observation under an optical microscope FIG. 3 120 100 80 60 40 2O O O 2 4. 6 8 O 12 t(h) FIG. 4 U.S. Patent May 21, 2013 Sheet 3 of 4 US 8.445,023 B2 U.S. Patent May 21, 2013 Sheet 4 of 4 US 8.445,023 B2 -H Intact -A- Crushed O 2 4 6 8 10 12 14 16 t(h) FIG. 6 US 8,445,023 B2 1. 2 ANT-MISUSE MICROPARTICULATE ORAL At the present time there is also a particularly serious PHARMACEUTICAL FORM undesirable behavior which affects teenagers and concerns analgesic AP (aAP), more especially morphine and opium CLAIM FOR PRIORITY derivatives. In fact, teenagers prepare for their parties a cock tail of vodka with oxycodone, which they easily extract from This application is a divisional of U.S. application Ser. No. the tablets with water and alcohol. This process consists in 11/439,432, filed May 24, 2006, which claims priority to U.S. crushing the tablet and pouring the powder into a glass of Provisional Patent Application Ser. No. 60/735,182, filed Vodka or water and then waiting for a sufficient time to com Nov. 10, 2005, and FR 05/53437, filed Nov. 10, 2005; the pletely extract the morphine derivatives, which can subse contents of which are herein incorporated by reference in 10 quently be absorbed. their entirety. Solid oral drugs can also be misused by chewing the drug before Swallowing it, instead of Swallowing it quickly in FIELD OF THE INVENTION accordance with the dosage instructions.
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