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(12) United States Patent (10) Patent No.: US 8,956,642 B2 Hobot Et Al

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(12) United States Patent (10) Patent No.: US 8,956,642 B2 Hobot Et Al USOO8956642B2 (12) United States Patent (10) Patent No.: US 8,956,642 B2 Hobot et al. (45) Date of Patent: Feb. 17, 2015 (54) BUPIVACAINE FORMULATION INA 4,735,804 A 4, 1988 Caldwell et al. POLYORTHOESTER CARRIER 4,758.436 A 7, 1988 Caldwell et al. 4,764,364 A 8, 1988 Heller et al. 4,765,973 A 8, 1988 Heller (75) Inventors: Christopher M. Hobot, Tonka Bay, MN 4,767,627 A 8, 1988 Caldwell et al. (US); Michael E. Benz, Ramsey, MN 4,780,319 A 10/1988 Zentner et al. (US); Keith R. Hildebrand, Houlton, 4,855,132 A 8, 1989 Heller et al. WI (US); Bryant J. Pudil, Plymouth, 4,898,928 A 2f1990 Heller et al. MN (US) 4.946,931 A 8, 1990 Heller et al. 4,957,998 A 9, 1990 Heller et al. (73) Assignee: Medtronic, Inc., Minneapolis, MN (US) 5,030,4575,013,821 A 7,5/1991 1991 N.Heller s et al. 5,108,755 A 4, 1992 Daniels et al. (*) Notice: Subject to any disclaimer, the term of this 5,211,951 A 5/1993 Sparer et al. patent is extended or adjusted under 35 35. A 1. E. gyet al. U.S.C. 154(b) by 1112 days. 5,374,681.- - w A 12/1994 Kronerget al. et al. 5,461,140 A 10, 1995 Heller et al. (21) Appl. No.: 12/426,005 5.487,739 A 1/1996 Aebischer et al. 5,587,507 A 12/1996 Kohnet al. (22) Filed: Apr. 17, 2009 5,618,563 A 4/1997 Berde et al. 5,700,485 A 12/1997 Berde et al. (65) Prior PublicationO O Data 5,747,0605,747,058 A 5/1998 TiptonSackler et et al. al. US 2009/O2O2436A1 Aug. 13, 2009 5,752.930 A 5/1998 Rise et al. 5,801, 188 A 9/1998 Hassenbusch, III et al. O O 5,824,343 A 10/1998 Ng et al. Related U.S. Application Data 5,837,228 A 11/1998 Shih et al. (60) Provisional application No. 61/046,343, filed on Apr. 3.26 A E. ity 1 18, 2008, provisional application No. 61/046,201, - - - be ea. filed on Apr. 18, 2008, provisional application No. (Continued) 61/046.213, filed on Apr. 18, 2008. FOREIGN PATENT DOCUMENTS 51) Int. Cl. (51) 2/00 (2006.01) EP O 168277 B1 1, 1986 EP O 168277 B2 1, 1986 AOIN 43/40 (2006.01) A6 IK3I/445 (2006.01) (Continued) A6IL 3L/I6 (2006.01) OTHER PUBLICATIONS (52) U.S. Cl. CPC ............... A6 IK3I/445 (2013.01); A61L 3 1/16 Moniche et al., in Anesthesiology 2002, 96,725-741.* (2013.01); A61 L 2300/402 (2013.01); A61 L (Continued) 2300/602 (2013.01) USPC - - - - - - - - - - - grgrrr. 424/426; 514/330 Primary Examiner — Dennis Heyer (58) Field of Classification Search Assistant Examiner — Daniel M Podgorski O See application file for complete search history. Attorney, Agent, or Firm — Sorell Lenna & Schmidt (56) References Cited (57) ABSTRACT U.S. PATENT DOCUMENTS Effective treatments of pain, such as chronic pelvic pain, for 2.957.856. A 10, 1960 G 1 extended periods of time are provided. The treatments 3.948,254 A 4, 1976 S.A. include the administration of one or more drug depots 4,079038 A 3, 1978 Choi et al. intraspinally wherein the drug depots include an effective 4,093,709 A 6, 1978 Choi et al. amount of bupivacaine formulated within a polyorthoester. 4,131,648 A 12/1978 Choi et al. By administration of one or more drug depots, one can relieve 3.SS- A 2.878 SSC pain caused by diverse sources, including but not limited to 4. i80,646 A 12, 1979 Choi et al. chronic pelvic pain syndromes, spinal disc herniation (i.e. 4,304.767 A 12/1981 Heller et al. sciatica), spondilothesis, Stenosis, discongenic back pain and 4.389,330 A 6, 1983 Tice et al. joint pain, as well as pain that is incidental to Surgery. In some is: A 1 i 3. instein et al. embodiments, the relief can be for at least thirty days, at least 4,532,335- K - A 7/1985 Helwingget al. S1Xty days, at least one hundred days or at least one hundred 4,549,010 A 10/1985 Sparer et al. and thirty-five days. 4,638.045 A 1, 1987 Kohn et al. 4,639,366 A 1, 1987 Heller 21 Claims, 6 Drawing Sheets US 8,956,642 B2 Page 2 (56) References Cited 2005, 00792O2 A1 4/2005 Chen et al. 2005/0090548 A1 4/2005 Hildebrand et al. 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WO WO 2005/OO9408 A2 2, 2005 6,790.458 9, 2004 Ng et al. WO WO 2005/OO9408 A3 2, 2005 6,793.938 9, 2004 Sankaram WO WO 2005/092337 A1 10/2005 6,822,000 11/2004 Ng et al. WO WO 2005/120435 A2 12/2005 6,861,068 3, 2005 Ng et al. WO WO 2007/133751 A2 11/2007 6,863,782 3, 2005 Newsome et al. WO WO 2008.005371 A2 1, 2008 6,921,541 7/2005 Chasin et al. 6,933,328 8, 2005 Schacht OTHER PUBLICATIONS 6,946,145 9, 2005 Ng et al. 6,969,383 11/2005 Hildebrand Al Malyan et al. in the Journal of Craniofacial Surgery 17,(2) 302 6,982,089 1, 2006 Tobinick 313, 2006.* 7,045,589 5, 2006 Heller et al. 7,163,694 1/2007 Heller et al. Einmahletal. in Investigative Ophthamology & Visual Science 42(3) 7,288,609 10, 2007 Pacetti 695-700 (2001).* 7,319,132 1, 2008 Musa Deng et al. in Pharmaceutical Development and Technology vol. 8, 2002fOO37300 3, 2002 Ng et al. No. 1, pp. 31-38, 2003.* 2002/0114835 8, 2002 Sackler et al. Kim et al. (International Journal of Pharmacuetics, 2005, 304, 165 2002/0176844 11, 2002 Ng et al. 177). 2003.0114394 6, 2003 Levine et al. PCT International Search Report, PCT/US2009/041 107, Mailed Oct. 2003. O138474 T/2003 Ng et al. 28, 2009. 2003/O152630 8, 2003 Ng et al. Anderson et al., “General Acid Catalysis of Ortho Ester Hydrolysis”. 2003/0170288 9, 2003 Carr et al. J. Org. Chem, 37(12): 1993-1996, Jun. 16, 1972. 2003/O185873 10, 2003 Chasin et al. Barret al., “PostSurgical Pain Management with Poly(ortho esters)”. 2003/0212148 11, 2003 Ng et al. 2004/OOO1872 1, 2004 Shih et al. Adv. Drug Deliv. Rev., 54(7): 1041-1048, Oct. 16, 2002. 2004/OO33251 2, 2004 Sparer et al. Chiang et al., “Effect of Phenyl Substitution on Ortho Ester 2004/OO39437 2, 2004 Sparer et al. Hydrolysis”. J.A.C.S., 96(14);4494-4499, Jul. 10, 1974. 2004.?00479.11 3, 2004 Lyu et al. Crivello et al., "Ketene Acetal Monomers: Systhesis and Character 2004/0086.569 5, 2004 Sparer et al. ization”. J.
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