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1. (WO2013124823) AN IMPROVED PROCESS FOR THE PREPARATION OF APREPITANT
Latest bibliographic data on file with the International Bureau   

Pub. No.:    WO/2013/124823    International Application No.:    PCT/IB2013/051440
Publication Date: 29.08.2013 International Filing Date: 22.02.2013
IPC:
C07D 413/06 (2006.01), C07D 265/32 (2006.01), A61K 31/5377 (2006.01)
Applicants: PIRAMAL ENTERPRISES LIMITED [IN/IN]; Piramal Tower, Ganpatrao Kadam Marg, Lower Parel, Mumbai 400013 (IN)
Inventors: LADKAT, Prashant; (IN).
WAGH, Ganesh; (IN).
JAGTAP, Ashutosh; (IN).
ROY, Mita; (IN).
HARIHARAN, Sivaramakrishnan; (IN).
CHOUKEKAR, Milind; (IN)
Priority Data:
495/MUM/2012  23.02.2012 IN
Title (EN) AN IMPROVED PROCESS FOR THE PREPARATION OF APREPITANT
(FR) PROCÉDÉ PERFECTIONNÉ POUR LA PRÉPARATION D'APRÉPITANT
Abstract: front page image
(EN)The present invention provides a process for the preparation of 5-[[(2R,3S)-2-[(1R)-1-[3,5- bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]methyl]-1,2-dihydro- 3H-1,2,4-triazol-3-one (Aprepitant) comprising condensation of 2-(R)-[(1R)-1-[3,5- bis(trifluoromethyl)phenyl]ethoxy]-3-(S)-(4-fluorophenyl)morpholine hydrochloride salt with 2-(2-chloro-1-iminoethyl)hydrazinecarboxylic acid methyl ester to obtain the reaction mixture containing 2-[2-[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4- fluorophenyl)-4-morpholinyl]-1-iminoethyl]hydrazinecarboxylic acid methyl ester, which is in-situ cyclized in the presence of dimethylsulfoxide and a polar protic solvent at a low temperature to yield aprepitant having purity ≥ 99.5%.
(FR)La présente invention porte sur un procédé pour la préparation de 5-[[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluorométhyl)phényl]éthoxy]-3-(4-fluorophényl)-4-morpholinyl]méthyl]-1,2-dihydro-3H-1,2,4-triazol-3-one (aprépitant) comprenant la condensation de sel chlorhydrate de 2-(R)-[(1R)-1-[3,5-bis(trifluorométhyl)phényl]éthoxy]-3-(S)-(4-fluorophényl)morpholine avec de l'ester méthylique de l'acide 2-(2-chloro-1-iminoéthyl)hydrazinecarboxylique afin d'obtenir le mélange réactionnel contenant de l'ester méthylique de l'acide 2-[2-[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluorométhyl)phényl]éthoxy]-3-(4-fluorophényl)-4-morpholinyl]-1-iminoéthyl]hydrazinecarboxylique, qui est cyclisé in situ en présence de diméthylsulfoxyde et d'un solvant protique polaire à une basse température pour produire de l'aprépitant ayant une pureté ≥ 99,5 %.
Designated States: 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, KM, 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.
African Regional Intellectual Property Organization (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, UG, ZM, ZW)
Eurasian Patent Organization (AM, AZ, BY, KG, KZ, RU, TJ, TM)
European Patent Office (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)
African Intellectual Property Organization (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG).
Publication Language: English (EN)
Filing Language: English (EN)