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(12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (43) International Publication Date 19 December 2013 (19.12.2013) WIPOIPCT (10) International Publication Number WO 2013/186692 A1 (51) International Patent Classification: C07D 403/12 C07D 401/04 C07D C07D 403/04 C07D C07D 405/12 C07D 409/14 401/10 403/10 (2006.01) (2006.01) (2006.01) (2006.01) (2006.01) (2006.01) (2006.01) C07D 413/10 (2006.01) C07D 417/10 (2006.01) C07D 417/12 (2006.01) C07D 249/12 (2006.01) A61K31/4196 (2006.01) A61P 29/00 (2006.01) (21) International Application Number: (22) International Filing Date: (25) Filing Language: (26) Publication Language: PCT/IB2013/054752 10 June 2013 (10.06.2013) English (30) Priority Data: 1733/MUM/2012 15 June 2012 (15.06.2012) 61/668,146 5 July 2012 (05.07.2012) 3 319/MUM/2012 19 November 2012(19.11.2012) 61/735,679 11 December 2012 (11.12.2012) 387/MUM/2013 February 8 2013 (08.02.2013) 61/792,225 15 March 2013 (15.03.2013) English IN US IN US IN IN (71) Applicant: GLENMARK PHARMACEUTICALS S.A. [CH/CH]; Chemin de la Combeta 5, CH-2300 La Chaux- de-Fonds (CH). (72) Inventors: GHARAT, Laxmikant Atmaram; Flat No-203 Tirupati Apartments, Pokhran road no - 2, Majiwada, Thane (West), Maharashtra 400601 (IN). MUTHUKA- MAN, Nagarajan; # 20, Malay Amman Kovil Street, Kodumudi, Erode, Tamil Nadu 638151 (IN). KHAIR- ATKAR-JOSHI, Neelima; 101, Devprayag CHS, Bhakti Mandir Rd, Hari Niwas, Panchpakhadi, Thane (W), Maha rashtra 400602 (IN). KATTIGE, Vidya Ganapati; 101, Eureka, Hiranandani Estate, Patlipada, Off Ghodbunder Road, Thane (W), Maharashtra 400607 (IN). (81) Designated States (unless otherwise indicated, for every kind of national protection available)'. AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (84) Designated States (unless otherwise indicated, for every kind of regional protection available)'. ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, KM, ML, MR, NE, SN, TD, TG). Published: — with international search report (Art. 21(3)) (54) Title: TRIAZOLONE COMPOUNDS AS mPGES-1 INHIBITORS CJ o\ 00 (I) —' A T-H o CJ (57) Abstract: The present disclosure is directed to compounds of formula (I), and pharmaceutically acceptable salts thereof, as mP - GES-1 inhibitors. These compounds are inhibitors of the microsomal prostaglandin E synthase-1 (mPGES-1) enzyme and are there fore useful in the treatment of pain and/or inflammation from a variety of diseases or conditions, such as asthma, osteoarthritis, rheumatoid arthritis, acute or chronic pain and neurodegenerative diseases. |