Patent SG-11201804204Q-A (SG)
Title: Process for the preparation of tricyclic pi3k inhibitor compounds and methods for using the same for the treatment of cancer
Inventor: STUMPF ANDREAS
IPC: C07D498/14
Filed: 2016-12-16
Abstract: INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property -' Organization International Bureau (43) International Publication Date .... ....r .„,„1 22 June 2017(22.06.2017) WIPO I PCT (10) WO International 111111111111311111111111111111111111111111111111111111111111111111111111111111111111111111 2017/106647 Publication Al Number (51) International Patent Classification: (74) Agents: CULLMAN, Louis, C. et al.; K&L Gates LLP, 1 A61K 31/519 (2006.01) CO7D 498/14 (2006.01) Park Plaza, Twelfth Floor, Irvine, CA 92614 (US). A61K 31/5383 (2006.01) (81) Designated States (unless otherwise indicated, for every (21) International Application Number: kind of national protection available): AE, AG, AL, AM, PCT/US2016/067174 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, (22) International Filing Date: DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, 16 December 2016 (16.12.2016) HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KH, KN, (25) Filing Language: English KP, KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, (26) Publication Language: English NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, (30) Priority Data: RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, 62/268,149 16 December 2015 (16.12.2015) US TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, 62/288,832 29 January 2016 (29.01.2016) US ZA, ZM, ZW. 62/291,248 4 February 2016 (04.02.2016) US (84) Designated States (unless otherwise indicated, for every (71) Applicant: GENENTECH, INC. [US/US]; 1 DNA Way, kind of regional protection available): ARIPO (BW, GH, South San Francisco, CA 94080 (US). GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, (72) Inventors: STUMPF, Andreas; Genentech, Inc., 1 DNA TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, Way, South San Francisco, CA 94080 (US). AN- DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, GELAUD, Remy; Genentech, Inc., 1 DNA Way, South LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, San Francisco, CA 94080 (US). MCCLORY, Andrew; SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, Genentech, Inc., 1 DNA Way, South San Francisco, CA GW, KM, ML, MR, NE, SN, TD, TG). 94080 YAJIMA, Herbert; Genentech, Inc., 1 DNA (US). Published: Way, South San Francisco, CA 94080 (US). NDUBAKU, Chudi; Genentech, Inc., 1 DNA Way, South San Fran- — with international search report (Art 21(3)) cisco, CA 94080 (US). OLIVERO, Alan; Genentech, Inc., 1 DNA Way, South San Francisco, CA 94080 (US). (54) Title: PROCESS FOR THE PREPARATION OF TRICYCLIC PI3K INHIBITOR COMPOUNDS AND METHODS FOR US- ING THE SAME FOR THE TREATMENT OF CANCER GDC-0084 in AcOH, Water Mixtures at 70°C 0.7 0.6 0.5 —x—AcOH/water 98:2 0. 4 —s—AcOH/water 9:1 % acetate amide —N—AcOH/water 4:1 0.3 - 0.2 .4t 0.1 IN —4o—AcOH/water 1:1 11. 0 C 1-1 N 1-1 : The present disclosure 0 1 2 3 6 time/h FIG. 1 provides for methods for preparing tricyclic PI3K inhibitor compounds in high yield and pur - N (57) ity in aqueous solvent systems.