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1. (WO1998049148) PREPARATION OF MIBEFRADIL II
Latest bibliographic data on file with the International Bureau

Pub. No.: WO/1998/049148 International Application No.: PCT/EP1998/002415
Publication Date: 05.11.1998 International Filing Date: 23.04.1998
Chapter 2 Demand Filed: 21.11.1998
IPC:
C07D 235/14 (2006.01)
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
235
Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
02
condensed with carbocyclic rings or ring systems
04
Benzimidazoles; Hydrogenated benzimidazoles
06
with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
14
Radicals substituted by nitrogen atoms
Applicants:
F. HOFFMANN-LA ROCHE AG [CH/CH]; Grenzacherstrasse 124 CH-4070 Basle, CH
Inventors:
HARRINGTON, Peter, John; US
WONG, Jim-Wah; US
Agent:
WITTE, Hubert; Grenzacherstrasse 124 CH-4070 Basle, CH
Priority Data:
60/046,79530.04.1997US
Title (EN) PREPARATION OF MIBEFRADIL II
(FR) PREPARATION DE MIBEFRADIL II
Abstract:
(EN) A method of preparing 2-[2-{[3-(1$i(H)-benzimidazol-2-yl) propyl]methyl-amino}ethyl]-6-fluoro-1-isopropyl-1,2,3,4- tetrahydronaphthalen-2-yl methoxyacetate comprises contacting (6-fluoro-2-hydroxy-1-isopropyl-1,2,3,4- tetrahydronaphthalen-2-yl)acetic acid or an activated derivative of (6-fluoro-2-hydroxy-1- isopropyl-1,2,3,4-tetrahydronaphthalen-2-yl)acetic acid with [3-(1$i(H)- benzimidazol-2-yl)propyl]methylamine to form $i(N)-[3-(1$i(H)-benzimidazol-2-yl) propyl]-2-(6-fluoro-2-hydroxy-1-isopropyl-1,2,3,4-tetrahydronaphthalen-2-yl) -$i(N)-methylacetamide, reducing this to 2-[2- {[3-(1$i(H)-benzimidazol-2-yl)propyl]methylamino}ethyl] -6-fluoro-1-isopropyl-1,2,3,4-tetrahydronaphthalen-2-ol, and treating the 2-[2- {[3-(1$i(H)-benzimidazol-2-yl)propyl]methylamino} ethyl]-6-fluoro-1-isopropyl-1,2,3,4-tetrahydronaphthalen -2-ol with methoxyacetic acid or an activated derivative of methoxyacetic acid.
(FR) L'invention a pour objet un procédé de préparation de 2-[2-{[3-(1$i(H)-benzimidazol-2-yl) propyl] méthyl-amino} éthyl]-6-fluoro-1-isopropyl-1,2,3,4-tétrahydronaphtalène- 2-yl-méthoxyacétate. Ce procédé consiste à placer l'acide acétique (6-fluoro-2-hydroxy-1-isopropyl-1,2,3,4- tétrahydro-naphtalène-2-yl) ou un dérivé activé d'acide acétique (6-fluoro-2-hydroxy-1- isopropyl-1,2,3,4-tétrahydronaphtalène-2-yl) en contact avec [3-(1$i(H)- benzimidazol-2-yl)propyl] méthylamine pour former N-[3-(1$i(H)-benzimidazol-2-yl) propyl]-2- (6-fluoro-2-hydroxy-1-isopropyl-1,2,3,4- tétrahydronaphtalène-2-yl)-N-méthylacétamide, et à réduire ce dernier en 2-[2- {[3-(1$i(H)-benzimidazol-2yl)propyl]méthylamino} éthyl]-6-fluoro-1-isopropyl-1,2,3,4, -tétrahydronaphtalène-2-ol. Ce procédé consiste ensuite à traiter le 2-[2-{ [3-(1$i(H)-benzimidazol-2-yl)propyl)] méthylamino}éthyl]-6-fluoro-1-isopropyl -1,2,3,4-tétrahydronaphtalène-2-ol avec de l'acide méthoxyacétique ou un dérivé activé d'acide méthoxyacétique.
Designated States: AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, CA, CH, CN, CU, CZ, DE, DK, EE, ES, FI, GB, GE, GH, GM, GW, HU, ID, IL, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MD, MG, MK, MN, MW, MX, NO, NZ, PL, PT, RO, RU, SD, SE, SG, SI, SK, SL, TJ, TM, TR, TT, UA, UG, UZ, VN, YU, ZW
African Regional Intellectual Property Organization (ARIPO) (GH, GM, KE, LS, MW, SD, SZ, UG, ZW)
Eurasian Patent Organization (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM)
European Patent Office (AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE)
African Intellectual Property Organization (BF, BJ, CF, CG, CI, CM, GA, GN, ML, MR, NE, SN, TD, TG)
Publication Language: English (EN)
Filing Language: English (EN)
Also published as:
AU1998079092