Patent SG-11201408013W-A (SG)
Title: Solid forms of an antiviral compound
Inventor: SCOTT ROBERT WILLIAM
IPC: C07D471/08
Filed: 2013-06-04
Abstract: (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (43) International Publication Date 12 December 2013 (12.12.2013) WIPOIPCT (10) International Publication Number WO 2013/184698 A1 (51) International Patent Classification: C07D 471/08 (2006.01) A61P 31/12 (2006.01) A61K31/4178 (2006.01) (21) International Application Number: (22) International Filing Date: (25) Filing Language: (26) Publication Language: (30) Priority Data: 61/655,934 61/759,295 13/800,374 5 June 2012 (05.06.2012) 31 January 2013 (31.01.2013) 13 March 2013 (13.03.2013) PCT/US2013/044138 4 June 2013 (04.06.2013) English English US US us (71) Applicant: GILEAD SCIENCES, INC. [US/US]; 333 Lakeside Drive, Foster City, California 94404 (US). (72) Inventors: SCOTT, Robert William; c/o Gilead Sciences, Inc., 333 Lakeside Drive, Foster City, California 94404 (US). WANG, Fang; c/o Gilead Sciences, Inc., 333 Lakeside Drive, Foster City, California 94404 (US). SHI, Bing; c/o Gilead Sciences, Inc., 333 Lakeside Drive, Foster — City, California 94404 (US). MOGALIAN, Erik; c/o Gilead Sciences, Inc., 333 Lakeside Drive, Foster City, California 94404 (US). (74) Agents: TANNER, Lorna L. et al.; Sheppard Mullin Richter & Hampton LLP, 379 Lytton Avenue, Palo Alto, California 94301-1479 (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, 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). Declarations under Rule 4.17: — as to applicant's entitlement to apply for and be granted a patent (Rule 4.17(H)) as to the applicant's entitlement to claim the priority of the earlier application (Rule 4.17(iii)) 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)) (54) Title: SOLID FORMS OF AN ANTIVIRAL COMPOUND o— 00 0\ 00 T-H rn T-H o CJ O Compound I (57) Abstract: Amorphous and crystalline solid forms of the anti-HCV compound (l-{3-[6-(9,9-difluoro-7-{2-[5-(2-methoxycar- bonylamino-3-methyl-butyryl)-5-aza-spiro[2.4]hept-6-yl]-3H-imidazol-4-yl}-9H-fluoren-2-yl)-lH- benzoimidazol-2-yl]-2-aza-bi- cyclo[2.2.1]heptane-2-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (Compound I) were prepared and characterized in the solid state: (Compound (I)). Also provided are processes of manufacture and methods of using the amorphous and crystalline forms.