Method for the preparation of ( S )- N...

Details Method for the preparation of ( S )- N... Method for the preparation of ( S )- N...

2006-12-22

2011-12-06

Solola, Taofiq A (Department: 1622)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

08071791

ABSTRACT:
A method of preparation of (S)-N-methyl-3-(1-naphthyloxy)-3-(2-mienyl)propylamine of Formula (I) and its pharmaceutically acceptable salts, comprising a) reaction of (RS)-N,N-dimethyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine with optically active D-tartaric acid or an acid salt derived from D-tartaric acid forming a mixture of diastereoisomeric salts of N,N-dimethyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine and D-tartaric acid (2:1), b) isolation of the salt (S)-N,N-dimethyl-3-(naphthyloxy) -3-(2-thienyl)propylamine/D-tartrate (2:1) from the mixture of diastereoisomeric salts in an organic solvent, water or a mixture thereof and release of (S)-N,N-dimethyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine by action of an inorganic or organic base, c) demethylation of (S)-N,N-dimethyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine by action of an alkylchloroformate of formula ClCOOR (R=C1-C5alkyl, or C6-C12aryl or alkylraryl), especially phenyl, ethyl or methyl chloroformate, and d) hydrolytic release of the duloxetine base of formula I and optionally conversion of the base to a salt with the respective acid, or salt of a weak base.

REFERENCES:
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patent: WO 2005/108386 (2005-11-01), None
patent: WO 2006/045255 (2006-05-01), None
patent: WO 2006/126213 (2006-11-01), None
Sorbera et al., “Duloxetine Oxalate”, Drugs of the Future, Barcelona, ES, vol. 25, No. 9, 2000, pp. 907-916.
International Search Report for International Application No. PCT/CZ2006/000096 mailed Jun. 29, 2007.

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