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1. (WO2007003982) IMPROVED PROCESS FOR THE MANUFACTURE OF FLECAINIDE
Latest bibliographic data on file with the International Bureau

Pub. No.: WO/2007/003982 International Application No.: PCT/IB2005/002682
Publication Date: 11.01.2007 International Filing Date: 09.09.2005
Chapter 2 Demand Filed: 24.04.2006
IPC:
C07D 213/127 (2006.01) ,C07D 213/40 (2006.01)
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
213
Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
02
having three double bonds between ring members or between ring members and non-ring members
04
having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
06
containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
127
Preparation from compounds containing pyridine rings
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
213
Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
02
having three double bonds between ring members or between ring members and non-ring members
04
having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
24
with substituted hydrocarbon radicals attached to ring carbon atoms
36
Radicals substituted by singly-bound nitrogen atoms
40
Acylated substituent nitrogen atom
Applicants:
GLADE ORGANICS PRIVATE LIMITED [IN/IN]; 19, Crystal 1st Floor, Juhu Road Santacruz (W) Mumbai 400 054, IN (AllExceptUS)
CHAWLA, Harmander, Pal, Singh [IN/IN]; IN (UsOnly)
CHOWDHARY, Anil, shankar [IN/IN]; IN (UsOnly)
LIMBAD, Piyush, Bhikhubhai [IN/IN]; IN (UsOnly)
JHA, Rajesh, Jagannathbhai [IN/IN]; IN (UsOnly)
JOSHI, Vipul, Narbheshankar [IN/IN]; IN (UsOnly)
Inventors:
CHAWLA, Harmander, Pal, Singh; IN
CHOWDHARY, Anil, shankar; IN
LIMBAD, Piyush, Bhikhubhai; IN
JHA, Rajesh, Jagannathbhai; IN
JOSHI, Vipul, Narbheshankar; IN
Agent:
SHUKLA, Vibha; K & S Partners 84-C, C-6 Lane Off Central Avenue Sainik Farms New Delhi 110062, IN
Priority Data:
789/MUM/200504.07.2005IN
Title (EN) IMPROVED PROCESS FOR THE MANUFACTURE OF FLECAINIDE
(FR) PROCÉDÉ AMÉLIORÉ DE FABRICATION DE LA FLÉCAÏNIDE
Abstract:
(EN) The invention describes an improved process for the manufacture of a Flecainide intermediate viz N-(pyridin-2-ylmethyl)-2,5-bis(2,2,2-trifluoroethoxy) benzamide (II). It consists of reacting 2,5-bis (2,2,2-trifluoroethoxy) benzoic acid with an acid chloride in a solvent mixture in presence of a base at -10 to -50°C. The resulting mixed anhydride is then condensed with 2-aminomethylpyridine at -10 to -40°C and the resulting product after aqueous workup is purified by crystallization. This affords the intermediate II in vastly improved yields and quality. The intermediate II on catalytic hydrogenation affords N-(2-piperidinylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide (Flecainide), isolated as its acetate.
(FR) La présente invention concerne un procédé amélioré de fabrication d'un intermédiaire de la flécaïnide à savoir le N-(pyridin-2-ylméthyl)-2,5-bis(2,2,2-trifluoroéthoxy)benzamide (II). Il consiste à faire réagir l'acide 2,5-bis(2,2,2-trifluoroéthoxy)benzoïque avec un chlorure d’acide dans un mélange de solvants en présence d'une base à une température de -10 à -50 °C. L'anhydride mélangé résultant subi alors une condensation avec la 2-aminométhylpyridine à une température de -10 à -40 °C et le produit résultant, après un traitement final aqueux, est purifié par cristallisation. Ceci permet d’obtenir l’intermédiaire II avec des rendements et une qualité énormément améliorés. L’intermédiaire II après hydrogénation catalytique donne le N-(2-pipéridinylméthyl)-2,5-bis(2,2,2-trifluoroéthoxy)benzamide (flécaïnide), isolé sous la forme de son acétate.
Designated States: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW
African Regional Intellectual Property Organization (ARIPO) (BW, GH, GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW)
Eurasian Patent Organization (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM)
European Patent Office (AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LT, LU, LV, MC, NL, PL, PT, RO, SE, SI, SK, 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)
Also published as:
EP1907360US20100184990