78628-81-6

Usage

Uses

cis-Terbinafine is an impurity in the production of Terbinafine hydrochloride.

Upstream product

• 14489-75-9 N-methyl-1-naphthalenemethylamine 
• 78629-20-6 3-hydroxy-6,6-dimethylhept-1-ene-4-yne 
• 635708-74-6 (Z)-1-chloro-6,6-dimethylhept-2-en-4-yne 
• 78628-80-5 terbinafine hydrochloride 
• 176168-78-8 N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthylmethyl amine hydrochloride 
• 704909-67-1 (Z)-N-(3-chloro-2-propenyl)-N-methyl-1-naphthalenemethanamine 
• 917-92-0 3,3-Dimethylbut-1-yne 
• 134865-58-0 (2E)-3-chloro-N-methyl-N-(naphthalen-1-ylmethyl)prop-2-en-1-amine 

Relevant academic research and scientific papers

Process for the preparation of terbinafine and salts thereof

A process for the preparation of Terbinafine and salts thereof by reacting 1-chloro-6,6-dimethylhept-2-en-4-yne and N-methyl-N-(1-naphthylmethyl)amine in a basic aqueous medium is disclosed. Also disclosed is a process for the preparation of 1-chloro-6,6-dimethylhept-2-en-4-yne.

Identification of impurities in the production of terbinafine hydrochloride

The purity of the parent substance of (E)-N-(6,6-dimethylhept-2-en-4-ynyl)- N-methylnaphth-1-ylmethylamine (terbinafine) is evaluated via TLC identification of the main impurities appearing during its synthesis via alkylation of N-methylnaphth-1-ylmethylamine with 1-chloro-6,6-dimethyl-2-hept-2-en-4-yne The possible formation of impurities including N-methyl-N,N-di(methylnaphth-1-yl) amine, N-methylnaphth-1-ylmethylamine, N-methylnaphth-2-ylmethylamine, (E)-N-(6,6-dimethylhept-2-en-4-ynyl)-N-methylnaphth-1-ylmethylamine, (Z)-N-(6,6-dimethylhept-2-en-4-ynyl)-N-methylnaphth-1-ylmethylamine, (E)-N-(6,6-dimethylhept-2-en-4-ynyl)-N-methylnaphth-2-ylmethylamine, and (Z)-N-(6,6-dimethylhept-2-en-4-ynyl)-N-methylnaphth-2-ylmethylamine was confirmed by means of countersynthesis.

PROCESS FOR PREPARING TERBINAFINE BY USING PLATINUM AS CATALYST

A process for the preparation of terbinafine, comprising the reaction of a compound of formula (II), or a salt thereof, wherein X is a leaving group, with tert-butylacetylene, in the presence of a platinum catalyst.

Synthesis and Antifungal Activity of (E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethanamine (SF 86-327) and Related Allylamine Derivatives with Enhanced Oral Activity

The allylamine derivatives are a new class of synthetic antifungal agents inhibiting fungal squalene epoxidase.A new subclass, which features an acetylene group conjugated with the allylamine double bond, is characterized by enhanced antifungal activity, especially on oral treatment of guinea pig dermatophytoses.Increased branching of the alkyl group next to the triple bond led to the tert-butylacetylene derivative SF 86-327, a compound with strikingly increased activity in vitro and in vivo, which is now under clinical evaluation.Versatile synthetic routes, comparative biological data, and structure-activity relationship are presented.