AR125001A1 - PROCESSES FOR PREPARING MODULATORS OF THE CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR - Google Patents
PROCESSES FOR PREPARING MODULATORS OF THE CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATORInfo
- 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
Links
Landscapes
- 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.
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) |
-
2018
- 2018-12-10 AR ARP180103603A patent/AR125001A1/en unknown
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