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Pub. No.: WO/2001/030742 International Application No.: PCT/DK2000/000586
Publication Date: 03.05.2001 International Filing Date: 20.10.2000
Chapter 2 Demand Filed: 09.05.2001
IPC:
C07C 209/26 (2006.01) ,C07C 209/62 (2006.01) ,C07C 209/70 (2006.01) ,C07C 211/42 (2006.01) ,C07C 251/20 (2006.01)
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
209
Preparation of compounds containing amino groups bound to a carbon skeleton
24
by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
26
by reduction with hydrogen
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
209
Preparation of compounds containing amino groups bound to a carbon skeleton
62
by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
209
Preparation of compounds containing amino groups bound to a carbon skeleton
68
from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
70
by reduction of unsaturated amines
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
211
Compounds containing amino groups bound to a carbon skeleton
33
having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
39
of an unsaturated carbon skeleton
41
containing condensed ring systems
42
with six-membered aromatic rings being part of the condensed ring systems
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
251
Compounds containing nitrogen atoms doubly- bound to a carbon skeleton
02
containing imino groups
20
having carbon atoms of imino groups being part of rings other than six-membered aromatic rings
Applicants: FISCHER, Erik[DK/DK]; DK (UsOnly)
TREPPENDAHL, Svend, Peter[DK/DK]; DK (UsOnly)
PEDERSEN, Søren, Bols[DK/DK]; DK (UsOnly)
A/S GEA FARMACEUTISK FABRIK[DK/DK]; Holger Danskes Vej 89 DK-2000 Frederiksberg, DK (AllExceptUS)
Inventors: FISCHER, Erik; DK
TREPPENDAHL, Svend, Peter; DK
PEDERSEN, Søren, Bols; DK
Agent: SIMONSEN, Christian, Rosendal ; Internationalt Patent-Bureau Høje Taastrup Boulevard 23 DK-2630 Taastrup, DK
Priority Data:
PA 1999 0154027.10.1999DK
Title (EN) IMPROVED SYNTHESIS OF RACEMIC SERTRALINE
(FR) SYNTHESE AMELIOREE DE SERTRALINE RACEMIQUE
Abstract:
(EN) The present invention describes an improved process for synthesis of sertraline, cis-(1S), (4S)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine. The new compound N-R-4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthaleneimine is hydrogenated to form N-R-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine which next is N-methylated to form N-R-N-methyl-4(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine. This latter compound is finally converted into sertraline by removal of the group R. The starting compound N-R-4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-napthaleneimine can be obtained in high yield from 4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone, tetralone, by reaction with R-amine. Further, new valuable intermediates for the synthesis of sertraline are provided.
(FR) La présente invention porte sur un procédé amélioré de synthèse de sertraline, cis-(1S), (4S)-N-méthyl-4-(3,4-dichlorophényl)-1,2,3,4-tétrahydro-1-naphthalèneamine. Le nouveau composé N-R-4-(3,4-dichlorophényl)-3,4-dihydro-1(2H)-naphthalèneimine est hydrogéné de façon à former N-R-4-(3,4-dichlorophényl)-1,2,3,4-tétrahydro-1-naphthalèneamine qui est ensuite N-méthylaté pour former N-R-N-méthyl-4(3,4-dichlorophényl)-1,2,3,4-tétrahydro-1-naphthalèneamine. Ce dernier composé est finalement converti en sertraline en le retirant du groupe R. Le composé de départ N-R-4-(3,4-dichlorophényl)-3,4-dihydro-1(2H)-napthalèneimine peut être produit à haut rendement à partir de 4-(3,4-dichlorophényl)-3,4-dihydro-1(2H)-naphthalenone, tétralone, par réaction avec R-amine. L'invention porte, en poutre, sur de nouveaux intermédiaires valables pour la synthèse de sertraline.
Designated States: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, BZ, CA, CH, CN, CR, CU, CZ, DE, DK, DM, DZ, EE, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NO, NZ, PL, PT, RO, RU, SD, SE, SG, SI, SK, SL, TJ, TM, TR, TT, TZ, UA, UG, US, UZ, VN, YU, ZA, ZW
African Regional Intellectual Property Organization (ARIPO) (GH, GM, KE, LS, MW, MZ, SD, SL, SZ, TZ, UG, ZW)
Eurasian Patent Office (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM)
European Patent Office (EPO) (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, GW, ML, MR, NE, SN, TD, TG)
Publication Language: English (EN)
Filing Language: English (EN)