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35. a 3. She & Gaia (Creatents out No. 1360S USOO835 0041B2 (12) United States Patent (10) Patent No.: US 8,350,041 B2 Carson et al. (45) Date of Patent: Jan. 8, 2013 (54) TRICYCLIC 8-OPIOID MODULATORS 2003. O166672 A1 9, 2003 Lubbert et al. 2005.0009860 A1 1/2005 Carson et al. 2006, OO30585 A1 2/2006 Dax et al. (75) Inventors: John R. Carson, Norristown, PA (US); 2006/0135522 A1 6/2006 Carson et al. Ellen Codd, Blue Bell, PA (US); 2006/01355.24 A1 6/2006 Carson et al. Christine M. Razler, Yardley, PA (US); 2006/0135763 A1 6, 2006 Coats et al. 2006/0148823 A1 7/2006 Coats et al. SEESRark McDonnell, Mrs. Lansdale, PAYS) (US); 2008.03189372006/0287297 A1 12/200812/2006 CoatsDeCorte et al.et al. James J. McNally, Souderton, PA (US) 2009 OO42871 A1 2/2009 Coats et al. (73) Assignee: Janssen Pharmaceutica, NV (BE) FOREIGN PATENT DOCUMENTS DE 2OO9555 10, 1970 (*) Notice: Subject to any disclaimer, the term of this EP 56O7 B1 11, 1979 patent is extended or adjusted under 35 E. 1992: R 1 39. U.S.C. 154(b) by 0 days. EP 1321169 A1 6, 2003 FR 22.902O2 A1 6, 1976 (21) Appl. No.: 13/334,374 GB 1128734 T 1966 WO WO9828275 A1 T 1998 (22) Filed: Dec. 22, 2011 WO WO 9900376 A1 1/1999 WO WO 014619 A1 6, 2001 O O WO WOO166543 A2 9, 2001 (65) Prior Publication Data WO WOO1723O3 A1 10, 2001 US 2012/0095010 A1 Apr. 19, 2012 WO WOO236573 A2 5, 2002 WO WOO248122 A2 6, 2002 O O WO WO O3035646 A2 5/2003 Related U.S. Application Data WO WO 2004.026030 A2 4/2004 (62) - - - of applit o30 fieddis in WOWo WOW56-66. 2004035541 A1A 10364, 2004 s , now Pat. No. 8,106.207, which is a division wo WO 2005OO3131 A1 1/2005 of application No. 12/536,635, filed on Aug. 6, 2009, OTHER PUBLICATIONS now Pat. No. 7,982,042, which is a division of application No. 10/873,527, filed on Jun. 22, 2004, Ananthan, S.: The AAPS Journal 2006, 8(1): El 18-E125. (in U.S. now Pat. No. 7,589, 103. Appl. No. 10/873,527). 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Primary Examiner – David KO'Dell 5502049 A 3/1996 Garret et al. (57) ABSTRACT g A '83. Air al The invention is directed to delta opioid receptor modulators. 6,153,626 A 11/2000 Pelcman et al. More specifically, the invention relates to tricyclic 6-opioid 7,060,711 B2 6, 2006 Lubbert et al. modulators. Pharmaceutical and Veterinary compositions and 7.432,257 B2 10/2008 Coats et al. methods of treating mild to severe pain and various diseases 2.- - - R: 1939. SEaX Cla. al using compounds of the invention are also described. 2003, OO18447 A1 1/2003 FlorSchuetz 22 Claims, No Drawings US 8,350,041 B2 Page 2 OTHER PUBLICATIONS Still, W. Clarket al.: Rapid Chromatographic Technique for Prepara Dorwald, FZ.: Side Reactions in Organic Synthesis (2005) Wiley: tive Separations with Moderate Resolution; J. Org. Chem. (1978) 43(14): 2923-2925. VCH. Weinheim p. 1X of Preface: 1-15. (in U.S. Appl. No. Structures in copending U.S. Appl. No. 11/195.231. (in U.S. Appl. 10/873,527). No. 1 1/424,311). 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