Some content of this application is unavailable at the moment.
If this situation persist, please contact us atFeedback&Contact
1. (WO2013120465) A PROCESS FOR THE PREPARATION OF RIVAROXABAN BASED ON THE USE OF (S)-EPICHLOROHYDRIN
Latest bibliographic data on file with the International Bureau   

Pub. No.: WO/2013/120465 International Application No.: PCT/CZ2013/000015
Publication Date: 22.08.2013 International Filing Date: 18.02.2013
IPC:
C07D 413/10 (2006.01) ,C07D 413/14 (2006.01)
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
413
Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
02
containing two hetero rings
10
linked by a carbon chain containing aromatic rings
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
413
Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
14
containing three or more hetero rings
Applicants:
ZENTIVA, K.S. [CZ/CZ]; U Kabelovny 130 102 37 Praha 10, CZ
Inventors:
HALAMA Ales; CZ
KRULIS Radim; CZ
DAMMER, Ondrej; CZ
KALASEK, Stanislav; CZ
Agent:
JIROTKOVA Ivana; Rott, Ruzicka & Guttmann P.O. Box 44, 120 00 Praha 2, CZ
Priority Data:
PV 2012-11116.02.2012CZ
Title (EN) A PROCESS FOR THE PREPARATION OF RIVAROXABAN BASED ON THE USE OF (S)-EPICHLOROHYDRIN
(FR) PROCÉDÉ DE PRÉPARATION DE RIVAROXABAN FONDÉ SUR L'UTILISATION DE (S)-ÉPICHLOROHYDRINE
Abstract:
(EN) The invention relates to the stereoisomers of 4-{4-[(S/R)-5-[(((aryl)methylene)- amino)methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-ones described by the chemical formulae (S)-(9) and (R)-(9). The optical isomer of compound (9) with the (S)- configuration is industrially applicable for the manufacture of the antithrombotic drug rivaroxaban (1). The new preparation process of rivaroxaban comprises a reaction of (S)-1- chloro-3-(((aryl)methylene)amino)propan-2-ols (S)-(14) with alkyl 4-(3-oxomorpholine-4- yl)phenylcarbamates (15) providing the key intermediate (S)-(9), which is further subjected to hydrolytic deprotection and subsequent acylation, producing rivaroxaban. The commercially available (S)-epichlorohydrin has been conveniently used as the chiral building block for the production of the key intermediate.
(FR) L'invention concerne les stéréoisomères de 4-{4-[(S/R)-5-[(((aryl)méthylène)-amino)méthyl]-2-oxo-1,3-oxazolidin-3-yl]phényl}morpholin-3-ones décrits par les formules chimiques (S)-(9) et (R)-(9). L'isomère optique du composé (9) de configuration (S) est applicable industriellement pour la fabrication du médicament antithrombotique rivaroxaban (1). Le nouveau procédé de préparation de rivaroxaban comprend une réaction de (S)-1-chloro-3-(((aryl)méthylène)amino)propan-2-ols (S)-(14) avec des 4-(3-oxomorpholine-4- yl)phénylcarbamates d'alkyle (15), fournissant l'intermédiaire clé (S)-(9), qui est ensuite soumis à une déprotection hydrolytique et une acylation ultérieure pour produire du rivaroxaban. La (S)-épichlorohydrine disponible dans le commerce a été utilisée de manière pratique en tant que constituant chiral pour la production de l'intermédiaire clé.
front page image
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 (ARIPO) (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, UG, ZM, ZW)
Eurasian Patent Office (AM, AZ, BY, KG, KZ, RU, TJ, TM)
European Patent Office (EPO) (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)