Invention Grant
- Patent Title: Process for the synthesis of cinacalcet hydrochloride
- Patent Title (中): 合成西那卡塞盐酸盐的方法
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Application No.: US12999648Application Date: 2008-06-18
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Publication No.: US08614354B2Publication Date: 2013-12-24
- Inventor: Massimo Ferrari , Marcello Ghezzi , Matteo Bonaldi
- Applicant: Massimo Ferrari , Marcello Ghezzi , Matteo Bonaldi
- Applicant Address: IT San Paolo d'Argon
- Assignee: Erregierre S.p.A.
- Current Assignee: Erregierre S.p.A.
- Current Assignee Address: IT San Paolo d'Argon
- Agency: Gifford, Krass, Sprinkle, Anderson & Citkowski, P.C.
- International Application: PCT/IT2008/000404 WO 20080618
- International Announcement: WO2009/153814 WO 20091223
- Main IPC: C07C211/00
- IPC: C07C211/00 ; C07C209/00

Abstract:
There is described a process for the preparation of cinacalcet hydrochloride (I) which includes the steps of: a) reacting (R)-(+)-1-(1-naphthyl)ethylamine (II) with 3-[3-(trifluoromethyl)phenyl]propenaldehyde (III) to afford the non isolated intermediate (R)—N-[3-[3-(trifluoromethyl)phenyl]-2-propenylimino-N-[1-(1-naphthyl)ethylamine (IV); b) reducing the non isolated intermediate (R)—N-[3-[3-(trifluoromethyl)phenyl]-2-propenylimino-N-[-1-(1-naphthyl)ethylamine (IV) with a sequential addition of:—a solution of sodium borohydride, methanol and a base,—oxalic acid and—a base to obtain (R)—N-[3-[3-(tifluoromethyl)phenyl]-2-propenyl]-1-(1-naphthyl)ethylamine (V) by passing through the precipitation of the oxalate salt of compound (V) after the addition of oxalic acid; c) hydrogenating (R)—N-[3-[3-(trifluoromethyl)phenyl]-2-propenyl]-1-(1-naphthyl)ethylamine (V) thus obtaining (R)—N-(3-(3-(trifluoromethyl)phenyl]propyl]-1-(1-naphthyl)ethylamine cinacalcet base (VI), which is retaken in ethyl acetate; and d) treating the solution of cinacalcet base (VI) in ethyl acetate with hydrochloric acid to afford cinacalcet hydrochloride (I).
Public/Granted literature
- US20110105799A1 PROCESS FOR THE SYNTHESIS OF CINACALCET HYDROCHLORIDE Public/Granted day:2011-05-05
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