Patent SG-11201408207T-A (SG)
Title: NOVEL 2,3-DIHYDRO-1H-IMIDAZO{1,2-a}PYRIMIDIN-5-ONE and this1,2,3,4-TETRAHYDROPYRIMIDO{1,2-a}PYRIMIDIN-6-ONE DERIVATIVES COMPRISING A SUBSTITUTED MORPHOLINE, PREPARATION THEREOF AND PHARMACEUTICAL USE THEREOF
Inventor: EL-AHMAD YOUSSEF
IPC: C07D487/04
Filed: 2013-06-21
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 2013/190510 A3 (51) International Patent Classification: C07D 233/46 (2006.01) C07D 519/00 (2006.01) C07D 239/14 (2006.01) A61K 31/5377 (2006.01) C07D 487/04 (2006.01) A61P 35/00 (2006.01) (21) International Application Number: (22) International Filing Date: (25) Filing Language: (26) Publication Language: PCT/IB2013/055099 21 June 2013 (21.06.2013) English (30) Priority Data: 1255917 22 June 2012 (22.06.2012) English FR (71) Applicant: SANOFI [FR/FR]; 54 rue La Boetie, F-75008 Paris (FR). (72) Inventors: EL-AHMAD, Youssef; c/o Sanofi, Patent De­ partment, 54 rue La Boetie, F-75008 Paris (FR). FILOCHE-ROMME, Bruno; c/o Sanofi, Patent Depart­ ment, 54 rue La Boetie, F-75008 Paris (FR). LETALLEC, Declarations under Rule 4.17: Jean-Philippe; c/o Sanofi, Patent Department, 54 rue La Boetie, F-75008 Paris (FR). MARCINIAK, Gilbert; c/o Sanofi, Patent Department, 54 rue La Boetie, F-75008 Par­ is (FR). RONAN, Baptiste; c/o Sanofi, Patent Department, 54 rue La Boetie, F-75008 Paris (FR). VIVET, Bertrand; c/o Sanofi, Patent Department, 54 rue La Boetie, F-75008 Paris (FR). (74) Agent: BOURGOUIN-MULLER, Alessandra; c/o San­ ofi, Patent Department, 54 rue La Boetie, F-75008 Paris (FR). (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). — of inventorship (Rule 4.17(iv)) 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)) (88) Date of publication of the international search report: 6 March 2014 (54) Title: NOVEL 2,3-DIHYDRO-lH-IMIDAZO{l,2-a}PYRIMIDIN-5-ONE and thisl,2,3,4-TETRAHYDROPYRIMIDO{l,2-a}PYRIMIDIN-6- ONE DERIVATIVES COMPRISING SUBSTITUTED MORPHOLINE, A PREPARATION THEREOF AND PHARMACEUTICAL USE THERE­ OF R7. VV 1 X ]]] si N'T JF R8 O. -U R12 1 R9 R10 R11 (I) ir, © o\ i-H cn i-H o CJ o & formula 1a formula 1b °o sy (57) Abstract: The invention relates to the novel products of formula (I) with p, q = 0, 1 or 2; R1 phenyl, pyridyl; = -(CH ) 2 m -Ra; alkylene; cycloalkyl; heterocycloalkyl; alkyl; -SO2 -Rb; -CO-Re; m = 1 or 2; Ra = aryl, heteroaryl, -CO-cycloalkyl, -CO-heterocyc- loalkyl, -CO-Rb, -C(Rb)=N-ORc, -CO 2 Rd, -CONRxRy; Rb = alkyl, aryl, heteroaryl; Rc = H, alkyl; Rd = alkyl, cycloalkyl; Re = al­ kyl, cycloalkyl, aryl, heteroaryl; NRxRy with Rx,Ry = H, alkyl, cycloalkyl, alkoxy, phenyl, or form with N a ring with optionally O, N; R2, R3 = H, alkyl, CF 3, or form with C a ring with optionally O, S and N; R4 = H, F, CI, CH 3 or CN; the morpholine substi­ is tuted with Me, and optionally substituted with F, OH; or is (Formula la) and the isomer of configuration R,R (Formula lb) these products being in all the isomer forms and the salts, as medicaments, in particular as anticancer medicaments.