Patent SG-11202000441Q-A (SG)
Title: Process for the preparation of n-((1r,2s,5r)-5-(tert-butylamino)-2-((s)-3-(7-tert-butylpyrazolo[1,5-a][1,3,5]triazin-4-ylamino)-2-oxopyrrolidin-1-yl)cyclohexyl)acetamide
Inventor: AYTAR BURCU SELIN
IPC: C07C233/41
Filed: 2018-07-19
Abstract: Title: PROCESS FOR THE PREPARATION OF N-((1R,2S,5R)-5-(TERT-BUTYLAMINO)-2-((S)-3-(7-TERT-BUTYLPYRA- ZOLO[1,5-A][1,3,5]TRIAZIN-4-YLAMINO)-2-0XOPYRROLIDIN-1-YL)CYCLOHEXYL)ACETAMIDE (57) : The invention generally relates to an improved process for the preparation of N-((lR,2S,5R)-5-(tert-butylamino)-24(S)-3-(7-tert-butylpyrazolo[1,5-a][1,3,5]triazin-4-ylamino)-2- oxopyrrolidin- 1 -yl)cyclohexyl)acetamide, as well as novel inteiinediates employed in the process, which may be useful for the treatment of cancer. N N N ( N H N O (12) INTERNATIONAL APPLICATION PUBLISHED (19) World Intellectual Property Organization International Bureau UNDER THE PATENT COOPERATION TREATY (PCT) vitivio VIII 00 los OH u oimIE (10) International Publication Number WO 2019/018592 A2 PCT (43) International Publication Date 24 January 2019 (24.01.2019) WIP0 I New Brunswick, New Jersey 08903 (US). GREEN, Rebec- ca A.; c/o Bristol-Myers Squibb Company, 1 Squibb Dri- ve, New Brunswick, New Jersey 08903 (US). HICKEY, Matthew R.; c/o Bristol-Myers Squibb Company, 1 Squibb Drive, New Brunswick, New Jersey 08903 (US). KOPP, Nathaniel David; c/o Bristol-Myers Squibb Company, 1 Squibb Drive, New Brunswick, New Jersey 08903 (US). LA CRUZ, Thomas E.; c/o Bristol-Myers Squibb Com- pany, 1 Squibb Drive, New Brunswick, New Jersey 08903 (US). LAUSER, Kathleen; c/o Bristol-Myers Squibb Com- pany, 1 Squibb Drive, New Brunswick, New Jersey 08903 (US). LEE, Hong Geun; Seoul National University, De- partment of Chemistry 503-620, 1 Gwanak-Ro Gwanak-Gu, Seoul 08826 (KR). LEAHY, David K.; 10 Ida Road, Mar- blehead, MA 01945 (US). LUO, Helen Y.; c/o Bristol-My- ers Squibb Company, 1 Squibb Drive, New Brunswick, New Jersey 08903 (US). RAZLER, Thomas M.; c/o Bristol-Myers Squibb Company, 1 Squibb Drive, New Brunswick, New Jersey 08903 (US). SAVAGE, Scott A.; c/o Bristol-Myers Squibb Company, 1 Squibb Drive, New Brunswick, New Jersey 08903 (US). SFOUGGATAKIS, Chris; c/o Bristol-Myers Squibb Company, 1 Squibb Dri- ve, New Brunswick, New Jersey 08903 (US). SOUMEIL- LANT, Maxime C.D.; c/o Bristol-Myers Squibb Compa- ny, 1 Squibb Drive, New Brunswick, New Jersey 08903 (US). ZARETSKY, Serge; c/o Bristol-Myers Squibb Com- pany, 1 Squibb Drive, New Brunswick, New Jersey 08903 (US). ZHENG, Bin; c/o Bristol-Myers Squibb Company, 1 Squibb Drive, New Brunswick, New Jersey 08903 (US). ZHU, Ye; 111 Clementi Road, #07-02, Singapore 129792 (SG). (74) Agent: KORSEN, Elliott et al.; Bristol-Myers Squibb Company, Route 206 & Province Line Road, Princeton, New Jersey 08543 (US). (51) International Patent Classification: C07D 235/06 (2006.01) (21) International Application Number: PCT/US2018/042797 (22) International Filing Date: 19 July 2018 (19.07.2018) English English (25) Filing Language: (26) Publication Language: (30) Priority Data: 62/534,908 20 July 2017 (20.07.2017) US (71) Applicant: BRISTOL-MYERS SQUIBB COMPANY [US/US]; Route 206 and Province Line Road, Princeton, New Jersey 08543 (US). (72) Inventors: AYTAR, Burcu Selin; c/o Bristol-Myers Squibb Company, 1 Squibb Drive, New Brunswick, New Jersey 08903 (US). BOROVIKA, Anna; c/o Bristol-My- ers Squibb Company, 1 Squibb Drive, New Brunswick, New Jersey 08903 (US). CHAN, Collin; c/o Bristol-My- ers Squibb Company, 1 Squibb Drive, New Brunswick, New Jersey 08903 (US). DEERBERG, Joerg; 11 Iron- gate Court, Columbus, New Jersey 08022 (US). DO- MAGALSKI, Nathan R.; 33 Bush Hill Drive, Niantic, Connecticut 0637 (US). EASTGATE, Martin D.; c/o Bristol-Myers Squibb Company, 1 Squibb Drive, New Brunswick, New Jersey 08903 (US). FAN, Yu; 603 S. 5th Avenue, Highland Park, New Jersey 08904 (US). FENSTER, Michael David Bengt; c/o Bristol-Myers Squibb Company, 1 Squibb Drive, New Brunswick, New Jersey 08903 (US). FOREST, Robert V.; c/o Bristol-My- ers Squibb Company, 1 Squibb Drive, New Brunswick, New Jersey 08903 (US). GONZALEZ-BOBES, Francis- co; c/o Bristol-Myers Squibb Company, 1 Squibb Drive, W O 20 19/0 185 9 2 A2 (I) [Continued on next page] WO 2019/018592 IIIIIIIIIIIIIIIII IIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIII (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, 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: without international search report and to be republished upon receipt of that report (Rule 48.2(g))