Patent SG-11201408100Y-A (SG)
Title: Prodrug derivatives of (e)-n-methyl-n-((3-methylbenzofuran-2-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide
Inventor: PARTRIDGE JOHN J
IPC: A61P31/04
Filed: 2013-06-19
Abstract: (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (43) International Publication Date 27 December 2013 (27.12.2013) WIPOIPCT (10) International Publication Number WO 2013/190384 A1 (51) International Patent Classification: C07F 9/6561 (2006.01) A61P 31/04 (2006.01) A61K31/675 (2006.01) C07F 9/60 (2006.01) (21) International Application Number: (22) International Filing Date: (25) Filing Language: (26) Publication Language: PCT/IB2013/001780 19 June 2013 (19.06.2013) English English (30) Priority Data: 61/661,559 19 June 2012 (19.06.2012) US (71) Applicant: AFFINIUM PHARMACEUTICALS, INC. [CA/CA]; 200 Front Street West, Suite 3004, P.O. Box 31, Toronto, Ontario, M5V 3K2 (CA). (72) Inventors: PARTRIDGE, John, J.; P.O. Box 16832, Chapel Hill, NC 27516-6832 (US). COLUCCI, John; 19011 Rue Poitiers, Kirkland, QC H9K 1S2 (CA). GAR- EAU, Yves; 55 Roger-maillet, Notre-Dame de L'ile-Perrot, QC J7V 7P2 (CA). THERIEN, Michel; 944 21st Avenue, Laval, QC H7R 4R2 (CA). ZAMBONI, Robert; 90 Kirk- wood, Beaconsfield, QC H9W 5L4 (CA). HAFKIN, Barry; 7000 North Mopac Expressway, Suite 200, Austin, TX 78731 (US). MARFAT, Anthony; 333 Lantern Hill Road, Mystic, CT 06355 (US). ZAGHDANE, Helmi; 835 de la falaise, Pincourt, Quebec J7W 0B9 (CA). (74) Agent: GRAVELLE, Micheline; Bereskin & Parr llp/S.E.N.C.R.L., Sri, 40 King street West, 40th Floor, Toronto, Ontario M5H 3Y2 (CA). (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). 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: PRODRUG 5,6,7,8-TETRAHYDRO-l, DERIVATIVES OF (E)-N-METHYL-N-((3-METHYLBENZOFURAN-2-YL)METHYL)-3-(7-OXO- 8-NAPHTHYRIDIN-3 -YL)ACRYLAMIDE •t 00 m o 0\ i-H o CJ (57) Abstract: In part, the present disclosure is directed to derivatives of (E)-N-methyl-N-(( 3-methylta l,8-naphthyndin-3-yl)acryl- amide compounds with significant solubility, solid state stability and bioavailability profiles. Said compounds have been found to be effective inhibitors of bacterial fatty acid metabolism via the effective inhibition of FabL hi addition, certain compounds are shown to be stable towards gamma radiation sterilization treatments, and are thus well-suited to the production of a sterile formulation for use in the treatment of illnesses caused by bacterial infections.