- A novel method for the large scale synthesis of cinacalcet hydrochloride using iron catalyzed C-C coupling
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A novel synthetic route for commercial preparation of cinacalcet hydrochloride (1), a calcimimetic agent and calcium-sensing receptor antagonist, is described. Our synthetic approach involves the preparation of cinacalcet using C-C bond formation catalyzed by iron acetylacetonate/NMP complex with aryl Grignard reagent benzotrifluoride magnesium bromide (8) and alkenyl halide N-chloropropene naphthylethylamine (6).
- Tewari, Neera,Maheshwari, Nitin,Medhane, Roshan,Nizar, Hashim,Prasad, Mohan
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- PROCESS FOR PREPARATION OF CINACALCET INTERMEDIATE AND CINACALCET HYDROCHLORIDE
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The present invention provides one pot process for preparation of highly pure unsaturated cinacalcet hydrochloride (II) comprising: i) converting 3-(trifluromethyl) cinnamic acid (III) into 3-(3-(trifluoromethyl)phenyl)prop-2-en-1-ol (IV), ii) converting 3-(3-(trifluoromethyl)phenyl)prop-2-en-1-ol (IV) to compound (V), wherein R is Cl, Br, I, tosylate and mesylate, Formula (V) iii) reacting compound (V) with (R)-1-(1-Naphthyl) ethylamine (VI) in presence of base followed by treatment with hydrochloric acid. The present invention further provides conversion of unsaturated cinacalcet hydrochloride (II) to cinacalcet hydrochloride (I).
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(2016/12/22)
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- PROCESSES FOR THE PREPARATION OF CINACALCET
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The present invention provides processes and intermediates for preparing cinacalcet base and pharmaceutically acceptable salts thereof.
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- PROCESSES FOR THE PREPARATION OF CINACALCET
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The present invention provides processes and intermediates for preparing cinacalcet base and pharmaceutically acceptable salts thereof.
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- UNSATURATED CINACALCET SALTS AND PROCESSES FOR PREPARING CINACALCET HYDROCHLORIDE
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Disclosed herein are convenient, industrially advantageous and environmentally friendly processes for the preparation of cinacalcet hydrochloride. Disclosed also herein are novel hydrochloride, oxalate and di-p-toluoyl-L-(+)-tartrate salts of (R)-a-methyl-N-[3-[3- (trifluoromethyl)phenyl]propylene]-l -naphthalenemethaneamine (unsaturated cinacalcet), solid state forms of the salts, and a process for their preparation thereof.
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Page/Page column 21
(2010/04/03)
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- HIGHLY PURE CINACALCET OR A PHARMACEUTICALLY ACCEPTABLE SALT THEREOF
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Provided herein are impurities of cinacalcet, (R)-α-methyl-N-[3-[3-(trifluoromethyl) phenyl]propyl]-1-(5,6,7,8-tetrahydronaphthalene)methaneamine (tetrahydro cinacalcet impurity), (R)-α-Methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-1- naphthalenemethaneamine-N-oxide (cinacalcet N-oxide impurity) and (R)-α-methyl-N-[3-[3- (trifiuoromethyl)phenyl]methyl]-1-naphthalenemethaneamine (benzylamine impurity); and processes for preparation and isolation thereof. Provided further herein is a highly pure cinacalcet or a pharmaceutically acceptable salt thereof substantially free of impurities, processes for the preparation thereof, and pharmaceutical compositions comprising highly pure cinacalcet or a pharmaceutically acceptable salt thereof substantially free of impurities.
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Page/Page column 40
(2010/07/02)
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