Patent SG-11201908947Q-A (SG)
Title: Process for the preparation of 6-(cyclopropaneamido)-4-((2-methoxy-3-(1-methyl-1h-1,2,4-triazol-3-yl)phenyl)amino)-n-(methyl-d3)pyridazine-3-carboxamide
Inventor: CHEN KE
IPC: C07D403/12
Filed: 2018-03-29
Abstract: DC, N H 0 (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (43) International Publication Date 04 October 2018 (04.10.2018) W I PO I PCT omit VIII °nolo OH mil O II (10) International Publication Number WO 2018/183649 Al (51) International Patent Classification: C07D 403/12 (2006.01) A61P 29/00 (2006.01) A61K 31/501 (2006.01) (21) International Application Number: PCT/US2018/025100 (22) International Filing Date: 29 March 2018 (29.03.2018) (25) Filing Language: English (26) Publication Language: English (30) Priority Data: 62/478,789 30 March 2017 (30.03.2017) US (71) Applicant: BRISTOL-MYERS SQUIBB COMPANY [US/US]; Route 206 and Province Line Road, Princeton, New Jersey 08543 (US). (72) Inventors: CHEN, Ke; 42 South Drive, East Brunswick, New Jersey 08816 (US). DEERBERG, Joerg; 11 Irongate Ct., Columbus, New Jersey 08022 (US). LIN, Dong; c/o Bristol-Myers Squibb Company, Route 206 and Province Line Road, Princeton, New Jersey 08543 (US). DUM- MELDINGER, Michael; c/o Bristol-Myers Squibb Com- pany, Route 206 and Province Line Road, Princeton, New Jersey 08543 (US). INANKUR, Bahar; c/o Bristol-My- ers Squibb Company, Route 206 and Province Line Road, Princeton, New Jersey 08543 (US). KOLOTUCHIN, Sergei V.; c/o Bristol-Myers Squibb Company, Route 206 and Province Line Road, Princeton, New Jersey 08543 (US). LI, Jun; c/o Bristol-Myers Squibb Company, Route 206 and Province Line Road, Princeton, New Jersey 08543 (US). ROGERS, Amanda J.; c/o Bristol-Myers Squibb Company, Route 206 and Province Line Road, Princeton, New Jersey 08543 (US). ROSSO, Victor W.; c/o Bris- tol-Myers Squibb Company, Route 206 and Province Line Road, Princeton, New Jersey 08543 (US). SIMMONS, Eric M.; c/o Bristol-Myers Squibb Company, Route 206 and Province Line Road, Princeton, New Jersey 08543 (US). SOUMEILLANT, Maxime C. D.; c/o Bristol-My- ers Squibb Company, Route 206 and Province Line Road, Princeton, New Jersey 08543 (US). TREITLER, Daniel S.; c/o Bristol-Myers Squibb Company, Route 206 and Province Line Road, Princeton, New Jersey 08543 (US). WANG, Jianji; 9 Aster Way, Dayton, New Jersey 08810 (US). ZHENG, Bin; c/o Bristol-Myers Squibb Company, Route 206 and Province Line Road, Princeton, New Jersey 08543 (US). SMITH, Michael J.; c/o Bristol-Myers Squibb Company, Route 206 and Province Line Road, Princeton, New Jersey 08543 (US). STROTMAN, Neil A.; c/o Bris- tol-Myers Squibb Company, Route 206 and Province Line Road, Princeton, New Jersey 08543 (US). TYMONKO, Steven; 577 Oxford Ln, Lindenhurst, Illinois 60046 (US). BENKOVICS, Tamas; 7 Vincent Court, East Brunswick, New Jersey 08816 (US). (74) Agent: KORSEN, Elliott et al.; Bristol-Myers Squibb Company, Route 206 and Province Line Road, Princeton, New Jersey 08543 (US). (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, DJ, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IR, IS, JO, JP, KE, KG, KH, KN, KP, KR, KW, KZ, LA, LC, LK, LR, LS, 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, SA, 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, ST, 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, = (54) Title: PROCESS FOR THE PREPARATION OF 6-(CYCLOPROPANEAMIDO)-44(2-METHOXY-3-(1-METHYL-1H-1,2,4- TRIAZOL-3-YL)PHENYL)AMINO)-N-(METHYL-D3)PYRIDAZINE-3-CARBOXAMIDE (57) : The invention relates to an improved process for synthesiz- ing 6-(cyclopropaneamido)-4-((2-methoxy-3-(1-methy1-1H-1,2,4-triazol-3-y1)phenypamino)-N-(m ethyl-d3)pyridazine-3-carboxamide of the formula: [INSERT CHEMICAL STRUCTURE HERE] Compound I is currently in clinical trials for the treatment of auto-immune and auto-inflammatory dis- eases such as psoriasis. 0 HN W O 20 18/1836 49 Al f N N ,N Me0 [Continued on next page] WO 2018/183649 Al MIDEDIMOMMIDIREIDIMINIIMINIMEHMEMOIMIE TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, KM, ML, MR, NE, SN, TD, TG). Declarations under Rule 4.17: — of inventorship (Rule 4.17(iv)) Published: with international search report (Art. 21(3)) before the expiration of the time limit for amending the claims and to be republished in the event of receipt of amendments (Rule 48.2(h))