US20170174613 Fenfluramine compositions and methods of preparing the same

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United States of America

Application Number 15385525

Application Date 20.12.2016

Publication Number 20170174613

Publication Date 22.06.2017

Grant Number 10351509

Grant Date 16.07.2019

Publication Kind B2

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Applicants ZOGENIX INTERNATIONAL LIMITED

Inventors Derek J. Londesbrough
Marc W. Andersen

Agents Karl Bozicevic
Bozicevic, Field & Francis LLP

Title

(EN) Fenfluramine compositions and methods of preparing the same

Abstract

(EN)

Methods of preparing a fenfluramine active pharmaceutical ingredient are provided. Aspects of the method include (a) hydrolyzing a 2-(3-(trifluoromethyl)phenyl)acetonitrile composition to produce a 2-(3-(trifluoromethyl)phenyl)acetic acid composition; (b) reacting the 2-(3-(trifluoromethyl)phenyl)acetic acid composition with acetic anhydride and a catalyst to produce a 1-(3-(trifluoromethyl)phenyl)propan-2-one composition; and

(c) reductively aminating the 1-(3-(trifluoromethyl)phenyl)propan-2-one composition with ethylamine using a borohydride reducing agent to produce a fenfluramine composition. Also provided are compositions and pharmaceutical ingredients prepared according to the subject methods including a pharmaceutically acceptable salt of fenfluramine and having less than 0.2% by weight in total of trifluoromethyl regioisomers.

C	CHEMISTRY; METALLURGY
07	ORGANIC CHEMISTRY
C	ACYCLIC OR CARBOCYCLIC COMPOUNDS
209	Preparation of compounds containing amino groups bound to a carbon skeleton
24	by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
28	by reduction with other reducing agents

C	CHEMISTRY; METALLURGY
07	ORGANIC CHEMISTRY
C	ACYCLIC OR CARBOCYCLIC COMPOUNDS
51	Preparation of carboxylic acids or their salts, halides, or anhydrides
42	Separation; Purification; Stabilisation; Use of additives
43	by change of the physical state, e.g. crystallisation

C	CHEMISTRY; METALLURGY
07	ORGANIC CHEMISTRY
C	ACYCLIC OR CARBOCYCLIC COMPOUNDS
51	Preparation of carboxylic acids or their salts, halides, or anhydrides
08	from nitriles

C	CHEMISTRY; METALLURGY
07	ORGANIC CHEMISTRY
C	ACYCLIC OR CARBOCYCLIC COMPOUNDS
45	Preparation of compounds having C=O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
78	Separation; Purification; Stabilisation; Use of additives
80	by liquid-liquid treatment

C	CHEMISTRY; METALLURGY
07	ORGANIC CHEMISTRY
C	ACYCLIC OR CARBOCYCLIC COMPOUNDS
45	Preparation of compounds having C=O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
61	by reactions not involving the formation of C=O groups
67	by isomerisation; by change of size of the carbon skeleton
68	by increase in the number of carbon atoms
72	by reaction of compounds containing C=O groups with the same or other compounds containing C=O groups

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1. US20170174613 - Fenfluramine compositions and methods of preparing the same

C	CHEMISTRY; METALLURGY
07	ORGANIC CHEMISTRY
B	GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
2200	Indexing scheme relating to specific properties of organic compounds
13	Crystalline forms, e.g. polymorphs