111111
`
`1111111111111111111111111111111111111111111111111111111111111
`US009492393B2
`
`c12) United States Patent
`McKenna et al.
`
`(10) Patent No.:
`(45) Date of Patent:
`
`US 9,492,393 B2
`*Nov. 15, 2016
`
`(54) TAMPER RESISTANT DOSAGE FORMS
`
`(71) Applicants:Purdue Pharma L.P., Stamford, CT
`(US); Purdue Pharmaceuticals L.P.,
`Wilson, NC (US)
`
`(72)
`
`Inventors: William H. McKenna, Yonkers, NY
`(US); Richard 0. Mannion, Furlong,
`PA (US); Edward P. O'Donnell,
`Basking Ridge, NJ (US); Haiyong H.
`Huang, Princeton, NJ (US)
`
`(73) Assignees: PURDUE PHARMA L.P., Stamford,
`CT (US); PURDUE
`PHARMACEUTICALS L.P., Wilson,
`NC (US)
`
`( *) Notice:
`
`Subject to any disclaimer, the term of this
`patent is extended or adjusted under 35
`U.S.C. 154(b) by 0 days.
`This patent is subject to a terminal dis-
`claimer.
`
`(21) Appl. No.: 14/729,660
`
`(22) Filed:
`
`Jun. 3, 2015
`
`(65)
`
`Prior Publication Data
`US 2015/0265600 Al
`Sep. 24, 2015
`
`Related U.S. Application Data
`(60) Continuation of application No. 14/515,924, filed on
`Oct. 16, 2014, now Pat. No. 9,084,816, which is a
`continuation of application No. 13/803,132, filed on
`Mar. 14, 2013, now abandoned, which is a division of
`application No. 11/844,872, filed on Aug. 24, 2007,
`now Pat. No. 8,894,987.
`(60) Provisional application No. 60/840,244, filed on Aug.
`25, 2006.
`
`(51)
`
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`
`Int. Cl.
`A61K 311485
`A61K 9128
`A61K 47110
`A61K 9120
`A61K 9116
`A61J 3106
`A61K 9100
`A61K 47134
`A61K 9124
`A61K 45106
`A61J 3110
`B29C 43100
`(52) U.S. Cl.
`CPC .. A61K 9128 (2013.01); A61J 3106 (2013.01);
`A61J 3110 (2013.01); A61K 910002 (2013.01);
`A61K 911641 (2013.01); A61K 91209
`(2013.01); A61K 912013 (2013.01); A61K
`912018 (2013.01); A61K 912031 (2013.01);
`A61K 912054 (2013.01); A61K 912077
`(2013.01); A61K 912095 (2013.01); A61K
`912853 (2013.01); A61K 912866 (2013.01);
`
`A61K 912893 (2013.01); A61K 311485
`(2013.01); A61K 45106 (2013.01); A61K 47110
`(2013.01); A61K 47134 (2013.01); B29C
`431003 (2013.01); A61K 9/2072 (2013.01)
`(58) Field of Classification Search
`CPC .. A61K 31/485; A61K 9/2893; A61K 47/10;
`A61K 51/1258
`See application file for complete search history.
`
`(56)
`
`References Cited
`
`U.S. PATENT DOCUMENTS
`
`636,438 A
`1,468,805 A
`1,485,673 A
`2,772,270 A
`3,096,248 A
`3,806,603 A
`3,885,027 A
`3,941,865 A
`3,966,747 A
`3,980,766 A
`4,070,494 A
`4,175,119 A
`4,404,183 A
`4,501,828 A
`4,599,342 A
`4,612,008 A
`4,616,644 A
`4,619,988 A
`4,629,621 A
`4,629,624 A
`4,690,822 A
`4,713,243 A
`4,744,976 A
`
`1111899 Lovejoy
`9/1923 Freund
`3/1924 Freund
`1111956 Weiss
`7/1963 Rudzki
`4/1974 Gaunt eta!.
`5/1975 Shaw eta!.
`3/1976 Miller eta!.
`6/1976 Monkovic et a!.
`9/1976 Shaw eta!.
`111978 Hoffmeister et al.
`1111979 Porter
`9/1983 Kawata et al.
`2/1985 Hadermann et a!.
`7/1986 LaHann
`9/1986 Wong et al.
`10/1986 Saferstein et a!.
`10/1986 Leung eta!.
`12/1986 Snipes
`12/1986 Grouiller et a!.
`9/1987 Uemura eta!.
`12/1987 Schiraldi et a!.
`5/1988 Snipes eta!.
`(Continued)
`
`FOREIGN PATENT DOCUMENTS
`
`CA
`CA
`
`10/1981
`1110972 A1
`6/2000
`2352874 A1
`(Continued)
`
`OTHER PUBLICATIONS
`
`Mai et al. (Materiaux et Constructions 1982. 15(2); pp. 99-106).*
`(Continued)
`
`Primary Examiner- Misook Yu
`Assistant Examiner- Kauser Akhoon
`(74) Attorney, Agent, or Firm- Troutman Sanders LLP
`
`(57)
`
`ABSTRACT
`
`The present invention relates to pharmaceutical dosage
`forms, for example to a tamper resistant dosage form includ-
`ing an opioid analgesic, and processes of manufacture, uses,
`and methods of treatment thereof.
`
`30 Claims, 27 Drawing Sheets
`
`KASHIV1001
`IPR of Patent No. 9,492,393
`
`

`

`(56)
`
`References Cited
`
`U.S. PATENT DOCUMENTS
`
`4,764,378 A
`4,765,989 A
`4,774,074 A
`4,783,337 A
`4,806,337 A
`4,861,598 A
`RE33,093 E
`4,892,778 A
`4,960,814 A
`4,970,075 A
`5,004,601 A
`5,019,397 A
`5,051,222 A
`5,139,790 A
`5,169,645 A
`5,200,197 A
`5,211,892 A
`5,266,331 A
`5,273,758 A
`5,273,760 A
`5,286,493 A
`5,330,766 A
`5,350,741 A
`5,356,467 A
`5,378,474 A
`5,393,528 A
`5,405,366 A
`5,458,887 A
`5,472,712 A
`5,478,577 A
`5,508,042 A
`5,549,912 A
`5,580,578 A
`5,654,005 A
`5,656,295 A
`5,672,360 A
`5,695,781 A
`5,801,201 A
`5,849,240 A
`5,866,161 A
`5,866,164 A
`5,886,164 A
`5,914,131 A
`5,945,125 A
`5,948,787 A
`5,958,452 A
`5,958,459 A
`5,968,551 A
`6,008,355 A
`6,009,690 A
`6,096,339 A
`6,117,453 A
`6,177,567 B1
`6,228,863 B1
`6,238,697 B1
`6,245,357 B1
`6,251,430 B1
`6,261,599 B1
`6,262,266 B1
`6,277,409 B1
`6,306,438 B1
`6,309,668 B1
`6,340,475 B2
`6,357,957 B1
`6,375,957 B1
`6,436,441 B1
`6,461,644 B1
`6,488,962 B1
`6,488,963 B1
`6,491,683 B1
`6,534,089 B1
`6,547,997 B1
`6,572,885 B2
`6,635,280 B2
`6,699,503 B1
`
`8/1988 Keith eta!.
`8/1988 Wong eta!.
`9/1988 Snipes
`1111988 Wong eta!.
`2/1989 Snipes eta!.
`8/1989 Oshlack
`10/1989 Schiraldi et a!.
`111990 Theeuwes et a!.
`10/1990 Wu eta!.
`1111990 Oshlack
`4/1991 Snipes
`5/1991 Wong eta!.
`9/1991 Marten eta!.
`8/1992 Snipes
`12/1992 Shukla et al.
`4/1993 Wright eta!.
`5/1993 Gueret
`1111993 Oshlack et a!.
`12/1993 Royce
`12/1993 Oshlack et a!.
`2/1994 Oshlack et a!.
`7/1994 Morella et al.
`9/1994 Takada
`10/1994 Oshlack et a!.
`111995 Morella et al.
`2/1995 Staab
`4/1995 Fox eta!.
`10/1995 Chen eta!.
`12/1995 Oshlack et a!.
`12/1995 Sackler et a!.
`4/1996 Oshlack et a!.
`8/1996 Oshlack et a!.
`12/1996 Oshlack et a!.
`8/1997 Chen eta!.
`8/1997 Oshlack et a!.
`9/1997 Sackler et a!.
`12/1997 Zhang eta!.
`9/1998 Graudums et a!.
`12/1998 Miller eta!.
`2/1999 Childers et a!.
`2/1999 Kuczynski et al.
`3/1999 Bird eta!.
`6/1999 Merrill eta!.
`8/1999 Kim
`9/1999 Merrill eta!.
`9/1999 Oshlack et a!.
`9/1999 Chasin et al.
`10/1999 Oshlack et a!.
`12/1999 Huang eta!.
`112000 Rosenberg et a!.
`8/2000 Ayer et al.
`9/2000 Seth eta!.
`112001 Chiu eta!.
`5/2001 Palermo et a!.
`5/2001 Kumar et al.
`6/2001 Edgren eta!.
`6/2001 Zhang eta!.
`7/2001 Oshlack et a!.
`7/2001 Chiu eta!.
`8/2001 Luber et al.
`10/2001 Oshlack et a!.
`10/2001 Bastin eta!.
`112002 Shell et al.
`3/2002 Champlin
`4/2002 Kaiko et al.
`8/2002 Sako eta!.
`10/2002 Jackson et al.
`12/2002 Berner eta!.
`12/2002 McGinity et al.
`12/2002 Dong eta!.
`3/2003 Ayer et al.
`4/2003 Breitenbach et a!.
`6/2003 Oshlack et a!.
`10/2003 Shell et al.
`3/2004 Sako eta!.
`
`US 9,492,393 B2
`Page 2
`
`4/2004 Gusler eta!.
`6,723,340 B2
`5/2004 Oshlack et a!.
`6,733,783 B2
`3/2005 Lin eta!.
`6,864,370 B1
`7/2005 Lam eta!.
`6,919,373 B1
`8/2005 Lam eta!.
`6,930,129 B2
`10/2006 Chapman et al.
`7,129,248 B2
`1112006 Oshlack et a!.
`7,141,250 B2
`12/2006 Casner eta!.
`7,153,966 B2
`1/2007 Sackler
`7,157,103 B2
`4/2007 Kumar eta!.
`7,201,920 B2
`7/2008 Hirsh eta!.
`7,399,488 B2
`3/2010 Chapman et al.
`7,674,799 B2
`3/2010 Chapman et al.
`7,674,800 B2
`3/2010 Chapman et al.
`7,683,072 B2
`8/2010 Bartholomaus et al.
`7,776,314 B2
`1112010 Oshlack et a!.
`7,842,307 B2
`2/2012 Bartholomaus et al.
`8,114,383 B2
`4/2012 Gupta eta!.
`8,163,798 B2
`1112012 Bartholomaus et al.
`8,309,060 B2
`12/2012 Wright eta!.
`8,337,888 B2
`8/2014 McKenna et a!.
`8,808,741 B2
`8/2014 McKenna et a!.
`8,815,289 B2
`9/2014 McKenna et a!.
`8,821,929 B2
`9/2014 McKenna et a!.
`8,834,925 B2
`9/2014 McKenna et a!.
`8,846,086 B2
`1112014 McKenna et a!.
`8,894,987 B2
`1112014 McKenna et a!.
`8,894,988 B2
`12/2014 McKenna et a!.
`8,911,719 B2
`7/2015 McKenna et a!.
`9,084,816 B2
`200110031278 A1
`10/2001 Oshlack et a!.
`1112001 Oshlack et a!.
`200110036476 A1
`1112001 Kolter eta!.
`200110038852 A1
`5/2002 Shell eta!.
`2002/0051820 A1
`8/2002 Ayer et al.
`2002/0114838 A1
`12/2002 Joshi eta!.
`2002/0187192 A1
`12/2002 Oshlack et a!.
`2002/0192277 A1
`112003 Kao et al.
`2003/0004177 A1
`112003 Krull eta!.
`2003/0015814 A1
`3/2003 Ziegler et a!.
`2003/0044464 A1
`4/2003 Oshlack et a!.
`2003/0064099 A1
`4/2003 Caruso eta!.
`2003/0065002 A1
`2003/0068375 A1 * 4/2003 Wright .
`2003/0068392 A1
`4/2003 Sackler
`2003/0069318 A1
`4/2003 Dang eta!.
`2003/0091630 A1
`5/2003 Louie-Helmet al.
`2003/0092724 A1
`5/2003 Kao et al.
`2003/0104052 A1
`6/2003 Berner et al.
`2003/0104053 A1
`6/2003 Gusler eta!.
`2003/0118641 A1
`6/2003 Maloney et a!.
`2003/0124185 A1
`7/2003 Oshlack et a!.
`2003/0129234 A1
`7/2003 Baichwal et al.
`2003/0133985 A1
`7/2003 Louie-Helmet al.
`2003/0152622 A1
`8/2003 Louie-Helmet al.
`2003/0161882 A1
`8/2003 Waterman
`2003/0203024 A1
`10/2003 Sako et al.
`2003/0224051 A1
`12/2003 Fink eta!.
`2003/0229158 A1
`12/2003 Chen eta!.
`2004/0010000 A1
`112004 Ayer et al.
`2004/0011806 A1
`112004 Luciano et a!.
`2004/0024006 A1
`2/2004 Simon
`2004/0047907 A1
`3/2004 Oshlack et a!.
`2004/0110781 A1
`6/2004 Harmon eta!.
`2004/0126428 A1
`7/2004 Hughes et al.
`2004/0137156 A1
`7/2004 Lee eta!.
`2004/0156899 A1
`8/2004 Louie-Helmet al.
`2004/0170680 A1
`9/2004 Oshlack et a!.
`2004/0185097 A1
`9/2004 Kannan et al.
`2004/0185105 A1
`9/2004 Berner et al.
`2004/0213848 A1
`10/2004 Li et al.
`2004/0241234 A1
`12/2004 Vilkov
`2005/0031546 A1 * 2/2005 Bartholomaus .
`
`A61K 9/2013
`424/468
`
`A61K 9/2031
`424/10.1
`
`2005/0106249 A1
`2005/0112067 A1
`2005/0127555 A1
`2005/0152843 A1
`2005/0222188 A1
`2005/0236741 A1
`
`5/2005 Hwang eta!.
`5/2005 Kumar eta!.
`6/2005 Gusik et al.
`7/2005 Bartholomaus et al.
`10/2005 Chapman et al.
`10/2005 Arkenau et al.
`
`KASHIV1001
`IPR of Patent No. 9,492,393
`
`

`

`US 9,492,393 B2
`Page 3
`
`(56)
`
`References Cited
`
`U.S. PATENT DOCUMENTS
`
`2005/0266084 A1
`2006/0002859 A1
`2006/0002860 A1
`2006/0173029 A1
`2006/0188447 A1
`2006/0193914 A1
`2006/0240107 A1
`2006/0240110 A1
`2006/0251724 A1
`2006/0269603 A1
`2007/0003616 A1
`2007/0020335 A1
`2007/0048228 A1
`2007/0092573 A1
`2007/0117826 A1
`2007/0117829 A1
`2007/0117831 A1
`2007/0183979 A1
`2007/0183980 A1
`2007/0196396 A1
`2008/017 5908 A1
`2008/0248113 A1
`2008/0274183 A1
`2008/0317854 A1
`2009/0005408 A1
`2009/0022798 A1
`2009/0081290 A1
`2010/0168148 A1
`201110038930 A1
`2013/0251796 A1
`2013/0251797 A1
`2013/0251800 A1
`2013/0251801 A1
`2013/0259938 A1
`2014/0024669 A1
`2014/0030327 A1
`2015/0028512 A1
`2015/0037411 A1
`2015/0037412 A1
`2015/0037413 A1
`
`12/2005 Li eta!.
`112006 Arkenau et a!.
`112006 Bartholomaus et a!.
`8/2006 Chapman et a!.
`8/2006 Arkenau-Maric eta!.
`8/2006 Ashworth et a!.
`10/2006 Lenaerts et a!.
`10/2006 Kiick eta!.
`1112006 Farrell et a!.
`1112006 Brown Miller et a!.
`112007 Arkenau-Maric eta!.
`112007 Chen eta!.
`3/2007 Arkenau-Maric eta!.
`4/2007 Joshi et al.
`5/2007 Janjikhel et a!.
`5/2007 Chapman et a!.
`5/2007 Chapman et a!.
`8/2007 Arkenau-Maric eta!.
`8/2007 Arkenau-Maric eta!.
`8/2007 Pilgaonkar et a!.
`7/2008 Liu eta!.
`10/2008 Bartholomaus et a!.
`1112008 Cook
`12/2008 Arkenau et a!.
`112009 Arkenau-Maric eta!.
`112009 Rosenberg et a!.
`3/2009 McKenna et a!.
`7/2010 Wright eta!.
`2/2011 Barnscheid et a!.
`9/2013 McKenna et a!.
`9/2013 McKenna et a!.
`9/2013 McKenna et a!.
`9/2013 McKenna et a!.
`10/2013 McKenna et a!.
`112014 McKenna et a!.
`112014 McKenna et a!.
`112015 McKenna et a!.
`2/2015 McKenna et a!.
`2/2015 McKenna et a!.
`2/2015 McKenna et a!.
`
`FOREIGN PATENT DOCUMENTS
`
`CA
`CA
`CA
`CA
`CA
`CH
`CN
`CN
`DE
`DE
`DE
`DE
`DE
`DE
`DE
`DE
`DE
`DE
`DE
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`
`2502965 A1
`2534925 A1
`2534932 A1
`2551231 A1
`2572491 A1
`689109 A5
`1130352 c
`1514721 A
`4309528 A1
`19753534 A1
`19800698 A1
`19822979 A1
`19855440 A1
`10036400 A1
`10227077
`69429710 T2
`10250083 A1
`10250084 A1
`10336400 A1
`0008131 A1
`0111144 A1
`0177893 A2
`0216453 A2
`0226061 A2
`0228417 A1
`0232877 A2
`0277289 A1
`0293066 A2
`0328775 A1
`0583726 A2
`0598606 A1
`0647448 A1
`
`5/2004
`2/2005
`2/2005
`7/2005
`112006
`10/1998
`12/2003
`7/2004
`9/1994
`6/1999
`7/1999
`12/1999
`6/2000
`6/2002
`6/2002
`8/2002
`12/2003
`5/2004
`3/2005
`2/1980
`6/1984
`4/1986
`4/1987
`6/1987
`7/1987
`8/1987
`8/1988
`1111988
`8/1989
`2/1994
`5/1994
`4/1995
`
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`GB
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`
`0661045 A1
`0682945 A2
`0693475 A1
`0696598 A1
`0780369 A1
`0820698 A1
`0889045 A1
`0974343 A1
`0980894 A1
`0998271 A1
`1250045 A2
`1293127 A2
`1658055 A1
`1859789 A1
`1897545 A1
`2070538 A1
`2080514 A1
`2082742 A1
`2292229 A1
`2292230 A1
`2311459 A1
`2343071 A1
`2384754 A1
`2399579 A1
`2399580 A1
`2450691 A
`W0-9003776 A1
`W0-9107950 A1
`W0-9306723 A1
`W0-9310758 A1
`W0-9311749 A1
`W0-9406414 A1
`W0-9408567 A1
`W0-9514460 A1
`W0-9520947 A1
`W0-9522319 A1
`W0-9530422 A1
`W0-9600066 A1
`W0-9608253 A1
`W0-9614058 A1
`W0-9632097 A1
`W0-9733566 A2
`W0-9737689 A2
`W0-9749384 A1
`W0-9749385 A1
`W0-9820073 A2
`W0-9844911 A1
`W0-9856354 A2
`W0-9856359 A2
`W0-9920255 A1
`W0-9932119 A1
`W0-9932120 A1
`W0-9944591 A1
`W0-0009639 A2
`W0-0032166 A2
`W0-0033835 A1
`W0-0115667 A1
`W0-0145644 A2
`W0-0226928 A1
`W0-02087512 A2
`W0-03013476 A1
`W0-030 13479 A1
`W0-03015531 A2
`W0-03024429 A1
`W0-03024430 A1
`W0-03026624 A1
`W0-03028698 A2
`W0-030286200 A1
`W0-03035029 A1
`W0-03035053 A1
`W0-03035054 A1
`W0-03035177 A2
`W0-03053417 A2
`W0-03072086 A1
`W0-03094812 A1
`W0-03105808 A1
`W0-2004016618 A1
`W0-2004026262 A2
`W0-2004026263 A2
`
`7/1995
`1111995
`111996
`2/1996
`6/1997
`111998
`111999
`1/2000
`212000
`5/2000
`10/2002
`3/2003
`5/2006
`1112007
`3/2008
`6/2009
`7/2009
`7/2009
`3/2011
`3/2011
`4/2011
`7/2011
`1112011
`12/2011
`12/2011
`112009
`4/1990
`6/1991
`4/1993
`6/1993
`6/1993
`3/1994
`4/1994
`6/1995
`8/1995
`8/1995
`1111995
`111996
`3/1996
`5/1996
`10/1996
`9/1997
`10/1997
`12/1997
`12/1997
`5/1998
`10/1998
`12/1998
`12/1998
`4/1999
`7/1999
`7/1999
`9/1999
`212000
`6/2000
`6/2000
`3/2001
`6/2001
`4/2002
`1112002
`2/2003
`2/2003
`2/2003
`3/2003
`3/2003
`4/2003
`4/2003
`4/2003
`5/2003
`5/2003
`5/2003
`5/2003
`7/2003
`9/2003
`1112003
`12/2003
`2/2004
`4/2004
`4/2004
`
`KASHIV1001
`IPR of Patent No. 9,492,393
`
`

`

`US 9,492,393 B2
`Page 4
`
`(56)
`
`References Cited
`
`FOREIGN PATENT DOCUMENTS
`
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`wo
`
`W0-2004037230 A1
`W0-2004037259 A1
`W0-2004037260 A1
`W0-2004093819 A2
`2005/000310 A1
`W0-2005016303 A2
`W0-2005016313 A1
`W0-2005016314 A1
`W0-2005041968 A2
`W0-2005063214 A1
`W0-2005079760 A1
`W0-2005097801 A1
`W0-2005102286 A1
`W0-2006002883 A1
`W0-2006002884 A1
`W0-2006002886 A1
`0679550 A2
`W0-2006082097 A1
`W0-2006082099 A1
`W0-2006084211 A2
`W0-2007008752 A2
`W0-2007048233 A1
`W0-2007053698 A2
`W0-2008086804 A2
`W0-2009114648 A1
`
`5/2004
`5/2004
`5/2004
`1112004
`1/2005
`2/2005
`2/2005
`2/2005
`5/2005
`7/2005
`9/2005
`10/2005
`1112005
`112006
`112006
`112006
`8/2006
`8/2006
`8/2006
`8/2006
`1/2007
`5/2007
`5/2007
`7/2008
`9/2009
`
`OTHER PUBLICATIONS
`
`A!Khatib eta!. (AAPS PharmSciTech, 2010. 11(1); pp. 253-266). *
`Mpofu eta!. (Journal of Colloid and Interface Science. 2004, 271;
`pp. 145-156).*
`Remington, 20th Edition, 2003, "Oral Solid Dosage Forms"
`Remington, 20th Edition, 2003, "Sustained and Controlled-Release
`Drug Delivery Systems"
`Gissinger et a!, A comparative evaluation of the properties of some
`tablet disintegrants, Drug Development and Industrial Pharmacy
`6(5): 511-536. 1980.
`JB. Ashworth, eta!., "Effect of Tablet mechanical Stability on Drug
`Preference and Relative Street Value of Oxycodone Controlled-
`Release (CR) Tablets inExperienced Oxycodone CR Abusers"
`(Abstract) Presented at the 69th Annual Scientific Meeting of the
`College on Problems of Drug Dependence (Quebec City, Canada,
`Jun. 16, 2007).
`J. Bartholomaeus, et a!., "A New Technology to Increase the
`Mechanical Stability of Matrix Tablets to Prevent Abuse by Crush-
`ing or Chewing" (Abstract) Presented at the Drug Formulations and
`Abuse Liability Conference "Impact of Drug Formulation onAbuse
`Liability, Safety and Regulatory Decisions" (North Bethesda, Mary-
`land, Apr. 19-20, 2005), pp. 12-13.
`V.K. Thoma eta!., "Bestimmung der In-vitro-Freigabe von schwach
`basischen Wirkstoffen aus Retardarzneiformen," Pharm. Ind. 51, Nr.
`3 (1989).
`S. Janicki eta!., "Slow-Release Microballs: Method of Preparation,"
`Acta Pharm. Techno!. 33(3) 154-155 (1987).
`R. Mank et a!., "Darstellung wirkstoffhaltiger Extrusionsformlinge
`auf der Basis von Thermoplasten," Pharmazie 45 (1990), H. 8; pp.
`592-593.
`R. Mank et a!., "Darstellung wirkstoffhaltiger Extrusionsformlinge
`auf der Basis von Thermoplasten," Pharmazie 44 (1989) H. 11; pp.
`773-776.
`P. Shivanand et a!., "Factors Affecting Release of KCI from Melt
`Extruded Polyethylene Disks," Pharmaceutical Research, Official
`Journal of the American Association of Pharmaceutical Scientists;
`Oct. 1991, vol. 8, No. 10.
`L. Yang eta!., "Characterization of Compressibility and Compat-
`ibility of Poly(ethylene oxide) Polymers for Modified Release
`Application by Compaction Simulator," Journal of Pharmaceutical
`Sciences, vol. 85, No. 10, Oct. 1996.
`F. Zhang et a!., "Properties of Sustained-Release Tablets Prepared
`by Hot-Melt Extrusion," Pharmaceutical Development and Tech-
`nology, 4(2), 241-250 (1999) pp. 241-250.
`
`A. Apicella et a!., "Poly(ethylene oxide) (PEO) and different
`molecular weight PEO blends monolithic devices for drug release,"
`Biomaterials 1993, vol. 14, No. 2, pp. 83-90.
`M.M. Crowley et a!., "Stability of polyethylene oxide in matrix
`tablets prepared by hot-melt extrusion," Biomaterials 23 (2002)
`4241-4248.
`M. Efentakis et a!., "Evaluation of High Molecular Weight
`Poly(Oxyethylene) (Polyox) Polymer: Studies of Flow Properties
`and Release Rates of Furosemide and Captopril from Controlled-
`Release Hard Gelatin Capsules," Pharmaceutical Development
`andTechnology, 5(3), 339-346 (2000).
`N. Follonier et al., "Various ways of modulating the release of
`diltiazem hydrochloride from hot-melt extruded sustained release
`pellets prepared using polymeric materials," Journal of Controlled
`Release 36 (1995) 243-250.
`N.B. Graham, "Poly(Ethylene Glycol) Gels and Drug Delivery,"
`Poly(Ethylene Glycol) Chemistry: Biotechnical and Biomedical
`Applications, Chapter 17, 1992.
`C. D. Hanning eta!., "The Morphine Hydrogel Suppository," British
`Journal of Anaesthesia, 1988, 61, 221-227.
`Kim et a!., "Preparation and Evaluation of Eudragit Gels V. Rectal
`Gel Preparations for Sustained Release and Avoidance of First-Pass
`Metabolism of Lidocaine," Chern. Pharm. Bull. 40(10) 2800-2804
`(1992).
`Cherng-Ju Kim, "Drug Release from Compressed Hydrophilic
`POLYOX-WSR Tablets," Journal of Pharmaceutical Sciences, vol.
`84, No. 3, Mar. 1995.
`S.L. Madorsky eta!., "Thermal Degradation of Polyethylene Oxide
`and Polypropylene Oxide," Journal of Polymer Science, vol.
`XXXVI, pp. 183-194 (1959).
`A. Moroni
`et
`a!.,
`"Application of Poly(Oxyethylene)
`Homopolymers in Sustained Release Solid Formulations," Drug
`Development and Industrial Pharmacy, 21(12), 1411-1428 (1995).
`N. Ohnishi et a!., "Effect of the Molecular Weight of Polyethylene
`Glycol on the Bioavailability of Indomethacin Sustained-Release
`Suppositories Prepared with Solid Dispersions," Chern. Pharm.
`Bull., 35 (8) 3511-3515 (1987).
`T. Ozeki et al., "Control of medicine release from solid dispersion
`the poly( ethylene oxide )-carboxyvinylpolymer
`composed of
`interpolymer complex by varying molecular weight of poly( ethyl-
`ene oxide)," Journal of Controlled Release 58 (1999) 87-95.
`Pharmaceutical Research, Official Journal of the American Asso-
`ciation of Pharmaceutical Scientists, Sep. 1989 (Supplement), vol.
`6, No. 9, 6.S-98.
`Pharmaceutical Research, Official Journal of the American Asso-
`ciation of Pharmaceutical Scientists, Oct. 1991 (Supplement), Vo. 8,
`No. 10, 8.S-192.
`W. Prapaitrakul et a!., "Release of Chlorpheniramine Maleate from
`Fatty Acid Ester Matrix Disks Prepared by Melt-extrusion," J.
`Pharm. Pharmacol. 1991, 43: 377-381.
`J. Scheirs eta!., "Characterizing the solid-state thermal oxidation of
`poly( ethylene oxide) powder," Polymer, 1991, vol. 32, No. 11.
`O.L. Sprockel et a!., "Permeability of Cellolose Polymers: Water
`Vapour Transmission Rates," J. Pharm. Pharmacol. 1990, 42: 152-
`157.
`J.L. Stringer et a!., "Diffusion of small molecular weight drugs in
`radiation-crosslinked poly( ethylene oxide) hydro gels," Journal of
`Controlled Release 42 (1996) 195-202.
`E. G. Rippie et a!., "Regulation of Dissolution Rate by Pellet
`Geometry," Journal of Pharmaceutical Sciences, Vo. 58, No.4, Apr.
`1969, pp. 428-431.
`Remington's Pharmaceutical Sciences 17th ed., Mack Publishing
`Co., (1985) 1418.
`M.S. Mesiha et al., "A Screening Study of Lubricants in Wet Powder
`Masses Suitable for Extrusion-Spheronization," Drug Development
`and Industrial Pharmacy, 19(8), 943-959 (1993).
`N. Follonier et al., "Evaluation of Hot-Melt Extrusion as a New
`Technique for the Production of Polymer-Based Pellets for Sus-
`tained Release Capsules Containing High Loadings of Freely
`Soluble Drugs," Drug Development and Industrial Pharmacy,
`20(8),1323-1339 (1994).
`"2.9.8. Resistance to Crushing of Tablets," Pharmaceutical Techni-
`cal Procedures, European Pharmacopoeia, p. 135 (1997).
`
`KASHIV1001
`IPR of Patent No. 9,492,393
`
`

`

`US 9,492,393 B2
`Page 5
`
`(56)
`
`References Cited
`
`OTHER PUBLICATIONS
`
`Bauer eta!., Coated Pharmaceutical Dosage Forms: Fundamentals,
`Manufacturing Techniques, Biopharmaceutical Aspects, Test Meth-
`ods and Raw Materials, Scientific Publishers Stuttgart 1998, CRC
`Press, 8 pp.
`Commonwealth of Australia, In the matter of Australian Patent
`Application No. 2002305559 in the name ofEndo Pharmaceuticals,
`Inc. and Opposition thereto by Mundipharma Pty Limited, apmm
`A0111098466v3 206030879 1.10., pp. 1-4, 2008.
`Coppens et a!., "Hypromellose, Ethylcellulose, and Polyethylene
`Oxide Use in Hot Melt Extrusion," Pharmaceutical Technology, 5
`pp. (2005/2006).
`Huang, Hugh, Poster and Abstract on extruded POLYOX tablets
`presented at the poster session of 2000 AAPS Annual Meeting, 4 pp.
`Maggi et al., "Dissolution behaviour of hydrophilic matrix tablets
`containing two different polyethylene oxides (PEOs) for the con-
`trolled release of a water-soluble drug. Dimensionality study,"
`Biomaterials, vol. 23, pp. 1113-1119 (2002).
`Proeschel et al., "Task-dependence of Activity/Bite-force Relations
`and its Impact on Estimation of Chewing Force from EMG," J Dent
`Res, vol. 81, No. 7, pp. 464-468 (2002).
`im
`Schroeder et a!., "Granulierung hydrophober Wirkstoffe
`Planetwalzenextruder" (Summary in English), Wissenschaft und
`Technik, Pharm. Ind., vol. 65, No.4, 367-372 (2003).
`"Oral Solid Dosage Forms," Remington's Pharmaceutical Sciences,
`18th edition, Chapter 89, pp. 1633-1665 (1990).
`Chiao et a!., "Sustained-Release Drug Delivery Systems,"
`Remington: The Science and Practice of Pharmacy, Chapter 94,
`Alfonso R. Gennaro, Ed., pp. 1660-1675 (1995).
`EP 1014941: Opposition brief filed by opponent Grunenthal dated
`Dec. 23, 2009 (includes English-language translation) (24 pages).
`EP1658054: Affidavit by Inventor of EP1658054, Prof. Johannes
`Bartholornaus, dated Oct. 7, 2009, with English translation (28
`pages).
`EP1658054: Annex to Third party observation-Test Report by
`Professor McGinity dated Jan. 26, 2009 ( 4 pages).
`EP1658054: English translation of Patentee's response dated Jan.
`15, 2009 (Reference C7) (8 pages).
`EP1658054: Opposition brief filed on Mar. 27, 2008 (15 pages).
`EP1658054: Patentee's Response to Opposition dated Jan. 15, 2009
`(12 pages).
`EP1658054: Third party observation dated Feb. 2, 2009 (4 pages).
`EP1658054: Third party observation dated Mar. 27, 2009 (3 pages).
`EP1658054: Wolfgang, Ritschel, Die Tablette: Handbuch der
`Entwicklung, Herstellung and Qualitatssicherung (extract), with
`English translation (2002) (5 pages).
`EP1658055: Annex to Third Party Observation-Test Report by
`Prof. McGinity dated Jan. 26, 2009 (4 pages).
`EP1658055: Berger et a!., Water-Soluble Resins, pp. 169-201
`(1962) (34 pages).
`EP1658055: Ethylene Oxide Polymers, Union Carbide Corporation,
`Technical Booklet (reprinted from Encyclopedia of Polymer Sci-
`ence and Technology, vol. 6, pp. 103-145 (1967).
`EP1658055: European Pharmacopoeia, 3rd Ed., chapter 2.9.8, 3
`pages (1997).
`EP1658055: Excerpt from Purdue Laboratory notebook (calibrated
`Instron test results) (4 pages)-Mar. 12, 2008.
`EP1658055: Experimental Report-Breaking strength tests on cali-
`brated Instron tester dated Mar. 12, 2008 (4 pages).
`EP1658055: Experimental Report-Breaking strength tests on
`uncalibrated Instron tester dated Dec. 6, 2007 (10 pages).
`EP1658055: IP Search, Sununary of prior art search for EP1658055
`provided by Swiss Intellectual Property Office dated Dec. 3, 2007
`(117 pages).
`EP1658055: Opposition brief filed on Dec. 14, 2007 (14 pages).
`EP1658055: Patentee's Response to Opposition dated Oct. 31,
`2008, with English translation (23 pages).
`EP1658055: Third Party Observation dated Feb. 2, 2009 (4 pages).
`EP1658055: Third Party Observation dated Mar. 27, 2009 (3 pages).
`
`EP1897545: Communicated dated Dec. 20,2007 from the European
`Patent Office containing the European Search Report (6 pages).
`EP1897545: Response to Office Communication dated May 21,
`2008 (15 pages).
`EP2070538: Annex! of the Report: Photos from First Hydration
`Rate (9 pages)-Mar. 5, 2010.
`EP2070538: Communication dated Jun. 25, 2009 from the Euro-
`pean Patent Office ( 4 pages).
`EP2070538: Communication dated May 18, 2009 from the Euro-
`pean Patent Office including the European Search Report (3 pages).
`EP2070538: Response to Office Communicated dated Mar. 5, 2010
`(23 pages).
`EP2080514: Communication dated Jun. 15, 2009 from the Euro-
`pean Patent Office containing the European Search Report (3
`pages).
`EP2080514: Office Action from EPO dated Jul. 14, 2009 ( 4 pages).
`EP2080514: Response to Office Communicated dated Mar. 19, 2010
`(14 pages).
`EP2082742: Communication dated Jul. 9, 2009 from the European
`Patent Office ( 4 pages).
`EP2082742: Communication dated Jun. 15, 2009 from the Euro-
`pean Patent Office containing the European Search Report (3
`pages).
`EP2082742: Response to Office Communication dated Mar. 19,
`2010 (21 pages).
`Falbe eta!. (Eds.), "Rompp Chemie Lexikon," with English trans-
`lation, 9 pages ( 1992).
`Andrx Lab Paragraph IV Letter, Feb. 7, 2011. [Confidential-Filed
`Under Seal].
`Watson Paragraph IV Letter, Feb. 7, 2011. [Confidential-Filed
`Under Seal].
`Teva Paragraph IV Letter, Feb. 9, 2011. [Confidential-Filed Under
`Seal].
`Actavis Paragraph IV Letter, Feb. 15, 2011. [Confidential-Filed
`Under Seal].
`Purdue v. Impax Paragraph IV Letter, Feb. 23, 2011. [Confiden-
`tial-Filed Under Seal].
`Ranbaxy Paragraph IV Letter, Feb. 24, 2011. [Confidential-Filed
`Under Seal].
`Ranbaxy Paragraph IV Letter, Mar. 23, 2010. [Confidential-Filed
`Under Seal].
`Mylan Paragraph IV Letter, Apr. 1, 2010. [Confidential-Filed
`Under Seal].
`Actavis Paragraph IV Letter, Apr. 8, 2010. [Confidential-Filed
`Under Seal].
`Ranbaxy Paragraph IV Letter, Apr. 8, 2010. [Confidential-Filed
`Under Seal].
`Mylan Paragraph IV Letter (U.S. Pat. No. 7,683,072), Apr. 9, 2010.
`[Confidential-Filed Under Seal].
`Mylan Paragraph IV Letter (U.S. Pat. No. 7,674,799 and U.S. Pat.
`No. 7,674,800), Apr. 9, 2010. [Confidential-Filed Under Seal].
`Varam, Inc. Paragraph IV Letter, Jun. 28, 2010. [Confidential-
`Filed Under Seal].
`Ranbaxy Paragraph IV Letter (NDA No. 02-2272), Aug. 25, 2011.
`[Confidential-Filed Under Seal].
`Purdue Paragraph IV Letter (Amneal Pharmaceuticals), Sep. 28,
`2011. [Confidential-Filed Under Seal].
`Sandoz Paragraph IV Letter, May 23, 2011 [Confidential-Filed
`Under Seal].
`Podczeck et a!., "Investigations into the tensile failure of doubly-
`convex cylindrical tablets under diametral loading using finite
`element methodology," International Journal of Pharmaceutics 454
`(2013) 412-424.
`Wikipedia-Newton (unit) (2014).
`Purdue v. Teva, Trial Decision (Case 04-MD-01603-SHS 568) (#
`149 Jan. 14, 2014).
`Report: Cured v. Heat-Compressed PEO Tablets (Mar. 2010);
`submitted in EP 2 070 538 (Application No. 09156832.9) and other
`EP and foreign applications.
`Choi et ai, "Development of a directly compressible poly( ethylene
`oxide) matrix for the sustained-release of dihydrocodeine bitartrate"
`Drug Dev and Ind. Pharm, 2003, 29(10), 1045-1052.
`
`KASHIV1001
`IPR of Patent No. 9,492,393
`
`

`

`US 9,492,393 B2
`Page 6
`
`(56)
`
`References Cited
`
`OTHER PUBLICATIONS
`
`Vippagunta eta!., "Chrystalline solids", Advanced Drug Delivery
`Reviews, 2001, 48, pp. 3-26.
`Braga et a!, "Crystal polymorphism and multiple crystal forms"
`Struct. Bond, 2009, 132, pp. 25-50.
`Mueller U, "Polymorphism", Inorganic Structural Chemistry, John
`Wiley and Sons, 1993, pp. 14-15.
`Donnelly, Craig L, "ADHD medications: past and future," Behav-
`ioral Health Management, (May 1, 2002).
`Ciccone Patrick, "Attempted Abuse of Concerta," Letters to the
`Editor, J. Am. Acad. Child Adolesc. Psychiatry, 41:7, (Jul. 2002).
`Cone, E.J., "Ephemeral profiles of prescription drug and forumla-
`tion tampering: Evolving pseudoscience on the Internet," Drug and
`Alcohol Dependence 83S S31-S39 (2006).
`Jaffe, Steven L., M.D., "Failed Attempts at Intranasal Abuse of
`concerta," Letters to the Editor, J. Am. Acad. Child Adolesc,
`Psychiatry, 41:1, (Jan. 2002).
`Bruan, David B.,"Poly(Ethylene Oxide)," Published by Union Car-
`bide Corporation, at p. 19-20 (1980).
`Griffith, Dorsey, "Potential new ADHD drug creating lots of big
`hopes," Sacramento Bee (California), (Oct. 30, 2002).
`"Practice Parameter for the Use of Stimulant Medications in the
`Treatment of Children, Adolescents, and Adults," J. Am. Acad.
`Child Adolesc. Psychiatry, 41:2 Supplement, (Feb. 2002).
`Huang, H., et al., "Preparation of Controlled Release Oral Dosage
`Froms by Low Temperature Melt Extrusion," American Association
`of Pharmaceutical Scientists,
`(Nov. 2000), Annual Meeting
`Extracts, Union Carbide Corporation.
`Currie, A.C., Some Reactions of 14-Hydroxycodeine, J. chemical
`Soc 'y 773 ( 1960).
`Stewart, A.W., Heterocyclic Division, 16 Ann. Rep. on Progress
`Chemistry 104 (1919).
`Apicella et a!., "Poly(ethylene oxide) (PEO) Constant Release
`Monolithic Devices" Polymers in Medicine: Biomedical and Phar-
`maceutical Applications, Chapter 3 (1993).
`Harris, Daniel C., Quantitative Chemical Analysis 646-49 (5th ed.
`1999).
`De Jong, Pharmaceutisch Weekblad Scientific Edition, 24-28
`(1987).
`Dow Technical Data, Polyox TM WSR, (Feb. 2003).
`Final Draft Labeling for Concerta Extended Release Tablets, (dated
`Jul. 2000 ), http:/ /www.accessdata.fda.gov/ drugsatfda.sub.---docs/
`label/2000/211-211b1.pdf.
`Handbook of Pharmaceutical Excipients, Arthur H. Kibbe, ed. at
`399 (3rd ed. 2000).
`Handbook of Pharmaceutical Excipients 280, (Ainley Wade & Paul
`J. Wellers eds. 2d. 1994).
`Handbook of Pharmaceutical Excipients 454, 460 (Raymond C.
`Rowe et a!. eds., 4th ed. 2003).
`http://www. accessdata.fda. gov I sri pts/ cder/ drugsatfda!index.
`cfm?fuseaction-Search.DrugDetails (accessed Aug. 21, 2013).
`http://www. bl ueli ght.ru/vb/ archive/index. php/t-36 8 56 .html
`(accessed Apr. 26, 20 13).
`http://www. bluelight.ru/vb/archive/index.php/t -39723 .html
`(accessed Apr. 26, 20 13).
`Ikuo lijima eta!., Studies in the ( + )-Morphinan Series, 5, Synthesis
`and Biological Properties of(+) Naloxone, 21 J. Medicinal Chem-
`istry 398 (1978).
`Seki, Isco, Studies on the Morphine Alkaloids and Its Related
`Compounds, XV, 17 Chemical & Pharm. Bull, 1549 ( 1969).
`Letter from Janet Woodcock, M.D., Director, Center for Drug
`Evaluation and Research, FDA to Philip C. Strassburger, Purdue
`Pharma L.P. and Edward B. Mahony, Rhodes Technologies Inc.,
`Responding to Citizen Petition and Petition for Stay of Action(Mar.
`24, 2008).
`Chapman, Robert, U.S. Appl. No. 60/651,778, "Process for prepar-
`ing oxycodone hydrochloride having
`less
`than 25 PPM
`14-hydroxycodeinone" (filed Feb. 10, 2005).
`Skelly et a!., Scaleup of Oral Extended-Release Dosage Forms,
`Pharmaceutical Research 10(12) 1800-05 (1993).
`
`Compilation of Monographs from Physicians' Desk Reference, 54th
`ed (2000).
`McGinity eta!., Hot-Melt Extrusion as a Pharmaceutical Process, V.
`4 (2) ' 25-36 (200 1 ).
`FDA's Guidance for Industry SUPAC-MR: Modified Release Solid
`Oral Dosage Forms, (Sep. 1997).
`Maurer, Peter J. et a!., Nitrogen-Bridged Conformationally Con-
`strained Etrophine Analogues. Synthesis and Biological Evaluation,
`30 J. Med. Chern. 2016 (1987).
`Morrison et a!., Organic Chemistry pp. 382-384; 548-549 (Allyn
`and Bacon, Inc. 4th ed. 1983).
`Harano,Teruo et al., 3a-Jydroxy-5.beta., 14.beta.-chol-8-en-24-oic
`Acid and its Isomer, Dehydration Products of Chenod