AR125001A1 - PROCESSES FOR PREPARING MODULATORS OF THE CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR - Google Patents

PROCESSES FOR PREPARING MODULATORS OF THE CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR

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Publication number
AR125001A1
AR125001A1 ARP180103603A ARP180103603A AR125001A1 AR 125001 A1 AR125001 A1 AR 125001A1 AR P180103603 A ARP180103603 A AR P180103603A AR P180103603 A ARP180103603 A AR P180103603A AR 125001 A1 AR125001 A1 AR 125001A1
Authority
AR
Argentina
Prior art keywords
salt
compound
formula
trimethylpyrrolidine
processes
Prior art date
Application number
ARP180103603A
Other languages
Spanish (es)
Inventor
Paul T Angell
Cristian Harrison
Bernice Lewandowski
Benjamin J Litter
Vito Melillo
William A Nugent
Robert M Hughes
Original Assignee
Vertex Pharma
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Vertex Pharma filed Critical Vertex Pharma
Publication of AR125001A1 publication Critical patent/AR125001A1/en

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  • Pyrrole Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Reivindicación 1: Un método para preparar un compuesto de fórmula (1), una sal farmacéuticamente aceptable del mismo, o un derivado deuterado de cualquiera de los anteriores, en donde: R¹ es un compuesto de fórmula (2) o (3); y el Anillo A es fenilo o un compuesto de fórmula (4); caracterizado porque comprende: (a) hacer reaccionar 2,2,6,6-tetrametil-piperidin-4-ona, o una sal de la misma, con cloroformo y al menos una base; (b) hacer reaccionar los productos de la reacción en (a) con un ácido para producir 5,5-dimetil-3-metilenopirrolidin-2-ona o una sal de la misma; (c) realizar una hidrogenación enantioselectiva de 5,5-dimetil-3-metilenopirrolidin-2-ona, o una sal de la misma, para producir (S)-3,5,5-trimetil-pirrolidin-2-ona o una sal de la misma; (d) reducir (S)-3,5,5-trimetil-pirrolidin-2-ona o una sal de la misma para producir (S)-2,2,4-trimetilpirrolidina; (e) opcionalmente tratar la (S)-2,2,4-trimetilpirrolidina con ácido para producir una sal de (S)-2,2,4-trimetilpirrolidina; y (f) hacer reaccionar (S)-2,2,4-trimetilpirrolidina, o una sal de la misma, con un compuesto de fórmula (5) o una sal de la misma, en donde: R¹ es un compuesto de fórmula (2) o (3); el Anillo A es fenilo o un compuesto de fórmula (4); y Xᵃ se selecciona entre halógenos, y en donde un compuesto de fórmula (1), una sal farmacéuticamente aceptable del mismo, o un derivado deuterado de cualquiera de los anteriores es producido.Claim 1: A method of preparing a compound of formula (1), a pharmaceutically acceptable salt thereof, or a deuterated derivative of any of the foregoing, wherein: R¹ is a compound of formula (2) or (3); and Ring A is phenyl or a compound of formula (4); characterized in that it comprises: (a) reacting 2,2,6,6-tetramethyl-piperidin-4-one, or a salt thereof, with chloroform and at least one base; (b) reacting the reaction products in (a) with an acid to produce 5,5-dimethyl-3-methylenepyrrolidin-2-one or a salt thereof; (c) carrying out an enantioselective hydrogenation of 5,5-dimethyl-3-methylenepyrrolidin-2-one, or a salt thereof, to produce (S)-3,5,5-trimethyl-pyrrolidin-2-one or a get out of it; (d) reducing (S)-3,5,5-trimethyl-pyrrolidin-2-one or a salt thereof to produce (S)-2,2,4-trimethylpyrrolidine; (e) optionally treating (S)-2,2,4-trimethylpyrrolidine with acid to produce a salt of (S)-2,2,4-trimethylpyrrolidine; and (f) reacting (S)-2,2,4-trimethylpyrrolidine, or a salt thereof, with a compound of formula (5) or a salt thereof, wherein: R¹ is a compound of formula ( 2 or 3); Ring A is phenyl or a compound of formula (4); and Xᵃ is selected from halogens, and wherein a compound of formula (1), a pharmaceutically acceptable salt thereof, or a deuterated derivative of any of the above is produced.

ARP180103603A 2017-12-08 2018-12-10 PROCESSES FOR PREPARING MODULATORS OF THE CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR AR125001A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US201762596452P 2017-12-08 2017-12-08

Publications (1)

Publication Number Publication Date
AR125001A1 true AR125001A1 (en) 2023-05-31

Family

ID=86688879

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP180103603A AR125001A1 (en) 2017-12-08 2018-12-10 PROCESSES FOR PREPARING MODULATORS OF THE CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR

Country Status (1)

Country Link
AR (1) AR125001A1 (en)

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