Patent SG-11201908863V-A (SG)
Title: Building blocks for stapled peptides
Inventor: YUEN TSZ YING
IPC: C07D265/34
Filed: 2018-03-23
Abstract: INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (43) International Publication Date 27 September 2018 (27.09.2018) WIPO I PCT mu °million °nolo olomommolomiono oimIE (10) International Publication Number WO 2018/174826 Al (51) International Patent Classification: C07C 227/18 (2006.01) C07D 265/32 (2006.01) C07C 229/48 (2006.01) C07D 265/34 (2006.01) C07K 1/107 (2006.01) (21) International Application Number: PCT/SG2018/050129 (22) International Filing Date: 23 March 2018 (23.03.2018) (25) Filing Language: English (26) Publication Language: English (30) Priority Data: 10201702443S 24 March 2017 (24.03.2017) SG (71) Applicant: AGENCY FOR SCIENCE, TECHNOLO- GY AND RESEARCH [SG/SG]; 1 Fusionopolis Way, Connexis North Tower, #20-10, Singapore 138632 (SG). (72) Inventors: YUEN, Tsz Ying; c/o Institute of Chemical and Engineering Sciences, 1 Pesek Road, Jurong Island, Sin- gapore 627833 (SG). JOHANNES, Charles William; c/ o Institute of Chemical and Engineering Sciences, 1 Pesek Road, Jurong Island, Singapore 627833 (SG). VERDINE, Greg; c/o Harvard University, Cambridge, Massachusetts 02138 (US). (74) Agent: SPRUSON & FERGUSON (ASIA) PTE LTD; P.O. Box 1531, Robinson Road Post Office, Singapore 903031 (SG). (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: with international search report (Art. 21(3)) in black and white; the international application as filed contained color or greyscale and is available for download from PATENTSCOPE (54) Title: BUILDING BLOCKS FOR STAPLED PEPTIDES R 2 () R 3 (57) : This invention relates to a method for producing an alkenyl 1 -aminocyclopropane-1 -carboxylic acid of Formula I wherein R 1 is a protecting group, n is an integer between 1 and 10, and A and B are chiral centres such that when A is S, B is R and when A is R, B is S. The method comprises a stereoselective formation of the cyclopropane moiety by cycloaddition onto a double bond, in a molecule comprising a chiral template, Formula lc. Further provided is the use of Formula I in the production of stapled peptides.