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United States Patent (10) Patent No.: US 9,630,959 B2 Ando Et Al

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United States Patent (10) Patent No.: US 9,630,959 B2 Ando Et Al US009630959B2 (12) United States Patent (10) Patent No.: US 9,630,959 B2 Ando et al. (45) Date of Patent: Apr. 25, 2017 (54) TRPV1 ANTAGONISTS INCLUDING 4,797.419 A 1/1989 Moos et al. DHYDROXY SUBSTITUENT AND USES 5,059,595 A 10/1991 Le Grazie THEREOF 5,073,543 A 12/1991 Marshall 5, 120,548 A 6/1992 McClelland et al. (71) Applicants:pp.11canus: Purdue Phnarma L.P., SlamStamford, Iord, CT 5,138,058 A 8, 1992 Geisen et al. (US); Shionogi & Co., Ltd., Osaka-shi (Continued) (JP) FOREIGN PATENT DOCUMENTS (72) Inventors: Shigeru Ando, Toyonaka (JP); CA 2114178 1, 1994 Noriyuki Kurose, Toyonaka (JP); EP 1388538 T 2003 Laykea Tafesse, Robbinsville, NJ (US) (Continued) (73) Assignees: Purdue Pharma L.P., Stamford, CT (US); Shionogi & Co., Ltd., Osaka (JP) OTHER PUBLICATIONS c Russian Office Action for Russian patent application No. (*) Notice: Subject to any disclaimer, the term of this 201410 1255 dated Nov. 10, 2015. patent is extended or adjusted under 35 Continued U.S.C. 154(b) by 0 days. (Continued) (21) Appl. No.: 15/018,493 Primary Examiner — Nizal Chandrakumar 9 (74) Attorney, Agent, or Firm — Dechert LLP (22) Filed: Feb. 8, 2016 (57) ABSTRACT (65) Prior Publication Data The disclosure relates to Compounds of Formula (I) US 2016/02220O2 A1 Aug. 4, 2016 Related U.S. Application Data OH (I) (63) Continuation of application No. 14/127,903, filed as application No. PCT/IB2012/001252 on Jun. 21, HO R4 2012, now Pat. No. 9,273,043. (60) Provisional application No. 61/499,989, filed on Jun. N 22, 2011. 2N (51) Int. Cl. R CO7D 403/00 (2006.01) N CO7D 417/4 (2006.01) N A6 IK 3/428 (2006.01) VVV (CH), C07D 417/12 (2006.01) - A6 IK 3/496 (2006.01) C07C 57/15 (2006.01) 1. C07C 59/255 (2006.01) O NH C07C 309/29 (2006.01) 4. C07C 309/30 (2006.01) % Ns (52) U.S. Cl. CPC .......... C07D 417/14 (2013.01); A61K 31/428 (2013.01); A61 K3I/496 (2013.01); C07C 57/15 (2013.01); C07C 59/255 (2013.01); C07C309/29 (2013.01); C07C309/30 (2013.01); C07D 417/12 (2013.01) Rs Ro (58) Field of Classification Search CPC .................................................... CO7D 417/14 and pharmaceutically acceptable derivatives thereof, where USPC . 544/364 R. R. Rs. Ro, and m are as defined herein, compositions See application file for complete search history. comprising an effective amount of a Compound of Formula (56) References Cited (I) or a pharmaceutically acceptable derivative thereof, and methods for treating or preventing a condition Such as pain, U.S. PATENT DOCUMENTS pain associated with osteoarthritis, osteoarthritis, UI, an ulcer, IBD, and IBS, comprising administering to an animal 3. A g 1929 RSig in need thereof an effective amount of a Compound of 384 5,770 A 11, 1974 fE. et al. Formula (I) or a pharmaceutically acceptable derivative 3,916,899 A 1 1/1975 Theeuwes et al. thereof. 4,008,719 A 2f1977 Theeuwes et al. 4.409,229 A 10/1983. Ong et al. 34 Claims, 3 Drawing Sheets US 9,630,959 B2 Page 2 (56) References Cited 8,604,037 B2 12/2013 Sun et al. 8,642,634 B2 2/2014 Pasteris et al. U.S. PATENT DOCUMENTS s: R: 1 58 urOSet et al.1 5,354,556. A 10/1994 Sparks et al. 9.434,721 B2 9/2016 Sun et al. 5,399,574 A 3, 1995 Robertson et al. 2003. 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