Please use this identifier to cite or link to this item: http://hdl.handle.net/2445/96772
Title: Synthesis of cinacalcet: an enantiopure active pharmaceutical ingredient (API)
Author: Barniol-Xicota, Marta
Leiva Martínez, Rosana
Escolano Mirón, Carmen
Vázquez Cruz, Santiago
Keywords: Amides
Amines
Medicaments
Amides
Amines
Drugs
Issue Date: Feb-2016
Publisher: Universidad Nacional de La Plata
Abstract: Cinacalcet hydrochloride is the only approved drug acting as calcimimetic, a new class of compds. used in the therapy of secondary hyperparathyroidism and parathyroid carcinoma. Several generic drug manufacturers and research groups from academia have reported alternative approaches to this mol., mainly from (R)​-​(+)​-​1-​(1-​naphthyl)​ethylamine. There are mainly three strategies that have been used to couple this readily accessible enantiopure amine to the other part of the mol.: amide formation followed by redn., reaction with an aldehyde and redn. of the resulting imine, and nucleophilic substitution with a suitable partner that carries a leaving group. More exotic approaches have also been disclosed. In the present review all of them are discussed. 1 Introduction 2 Synthetic Approaches Involving the Synthesis of an Amide Followed by Its Redn. 2.1 Approaches Involving Satd. Amide 2 from Acid 32.2 Approaches Involving Acrylamide 52.3 Alternatives Approaches Involving Amides 3 Synthetic Approaches Involving a Reductive Amination 3.1 Processes for the Synthesis of 3-​(Trifluoromethyl)​cinnamaldehyde (18) and 3-​[3-​(Trifluoromethyl)​phenyl]​propanal (20) 3.2 Processes Involving 183.3 Processes Involving 204 Synthetic Approaches Involving a Substitution Reaction 4.1 Substitutions Involving Alkyl Halides or Pseudohalides 4.2 Substitutions Involving Allyl Halides or Pseudohalides 4.3 Substitution Involving a Propynyl Mesylate 4.4 Direct Substitution without Activating the Hydroxyl Group 5 Misc. Synthetic Approaches 6 Conclusions.
Note: Reproducció del document publicat a: http://dx.doi.org/10.1055/s-0035-1561506
It is part of: Synthesis, 2016, vol. 48, num. 6, p. 783-803
Related resource: http://dx.doi.org/10.1055/s-0035-1561506
URI: http://hdl.handle.net/2445/96772
ISSN: 0328-1205
Appears in Collections:Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
Articles publicats en revistes (Institut de Biomedicina (IBUB))

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