Patent SG-11201803810X-A (SG)
Title: 1,3,4-thiadiazole compounds and their use in treating cancer
Inventor: FINLAY MAURICE
IPC: C07D417/14
Filed: 2016-11-30
Abstract: INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property -' Organization International Bureau (43) International Publication Date .... ....r .„,„1 8 June 2017 (08.06.2017) W I P0 1 PCT ID Hit (10) 1111111111111111111 WO International Ell 1111111111 2017/093299 Publication 111111111111111111111 Number Al RID 1111 IIII IIII (51) International Patent Classification: raham Research Campus, Cambridge Cambridgeshire C07D 417/14 (2006.01) A61K 31/53 (2006.01) CB22 3AT (GB). A61K 31/501 (2006.01) A61P 35/00 (2006.01) (74) Agent: COOK, Andrew; AstraZeneca Intellectual Prop - (21) International Application Number: erty Mereside, Alderley Park, Macclesfield Cheshire SK10 PCT/EP2016/079250 4TG (GB). (22) International Filing Date: (81) Designated States (unless otherwise indicated, for every 30 November 2016 (30.11.2016) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, (25) Filing Language: English BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, (26) Publication Language: English DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, (30) Priority Data: KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, 62/260,789 30 November 2015 (30.11.2015) US MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, (71) Applicants: ASTRAZENECA AB [SE/SE]; SE-151 85 OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, Sodertalje (SE). CANCER RESEARCH TECHNO- SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, LOGY LIMITED [GB/GB]; Angel Building 407 St John TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, Street, London EC1V 4AD (GB). ZW. (72) Inventors: FINLAY, Maurice, Raymond, Verschoyle; (84) Designated States (unless otherwise indicated, for every AstraZeneca R&D Cambridge, Darwin Building Cam- kind of regional protection available): ARIPO (BW, GH, bridge Science Park, Milton Road, Cambridge Cambridge- GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, shire CB4 OFZ (GB). NISSINK, Johannes, Wilhelmus, TJ, TM), European AT, BE, BG, CH, CY, CZ, DE, Maria; AstraZeneca R&D Cambridge, Darwin Building (AL, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, Cambridge Science Park, Milton Road, Cambridge Cam- LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, bridgeshire CB4 OFZ (GB). CHARLES, Mark, David; SM, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, CRT Discovery Laboratories, Jonas Webb Building, Bab KM, ML, MR, NE, SN, TD, TG). [Continued on next page] (54) Title: 1,3,4-THIADIAZOLE COMPOUNDS AND THEIR USE IN TREATING CANCER : A Foi (57) compound of ula (I) or a pharmaceutically acceptable salt thereof, where: Q can be 1,2,4-triazin-3-yl, pyridazin- 3-yl, 6-methylpyridazin-3-yl, or 6- can fluoropyridazin-3-y1; R 1 be hydrogen, 3- R methoxy, trifluoromethoxy, oxetan-3-yl, fluoroazetidin-l-yl, 3-methoxyazetidin-l-yl, 3 or 3,3- difiuoroazetidin- 1 -y1; R 2 can be hy- or can or drogen fluor(); R 3 be hydrogen methoxy; and R 4 can be methoxy, ethoxy, or methoxymethyl; that when R 1 is hy- provided drogen, trifluoromethoxy, then methoxy or R 3 is hydrogen, R 4 is not and/or methoxy- methyl. The compound of foiinula (I) can in- hibit glutaminase, e.g., GLS1. \ ,-, .4t o,N cr\ ei en Q cr\ o N ,-, o ei I N (I) N O WO 2017/093299 Al IMIOHO1101 DIDIIM01011110111110111111111111110111011110111111 Published: — with international search report (Art. 21(3))