78613-38-4

Basic information

• Product Name: Amorolfine hydrochloride
• Synonyms: AMOROLFINE HCL;Amorolfine HCI;Morpholine, 4-[3-[4-(1,1-dimethylpropyl)phenyl]-2-methylpropyl]-2,6-dimethyl-, hydrochloride, (2R,6S)-rel-;Morpholine, 4-[3-[4-(1,1-dimethylpropyl)phenyl]-2-methylpropyl]-2,6-dimethyl-, hydrochloride, cis-;Ro 14-4767/002;(+/-)-cis-2,6-Dimethyl-4-[2-methyl-3-(p-tert-pentylphenyl)propyl]morpholine hydrochloride;Amorolfine hydrochloride;(2R,6S)-rel-4-[3-[4-(1,1-dimethylpropyl)phenyl]-2-methylpropyl]-2,6-dimethyl-morpholine, hydrochloride (1:1)
• CAS NO: 78613-38-4
• Molecular Formula: C21H36ClNO
• Molecular Weight: 353.97
• EINECS: 276-715-9
• Product Categories: Antifungal (Topical);Antifungals for Research and Experimental Use;Biochemistry;HYTRIN
• Mol File: 78613-38-4.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 120 C
• Flash Point: 119.6 °C
• Appearance: white to beige/
• Density: 1.234
• Vapor Pressure: 7.75E-07mmHg at 25°C
• Refractive Index: 1.488
• Storage Temp.: room temp
• Solubility: DMSO: ≥5mg/mL (warmed)
• CAS DataBase Reference: Amorolfine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Amorolfine hydrochloride(78613-38-4)
• EPA Substance Registry System: Amorolfine hydrochloride(78613-38-4)

Safety Data

• Hazard Codes: Xn,N
• Statements: 20/21/22-36/37/38-50/53-38-22
• Safety Statements: 26-36-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 78613-38-4(Hazardous Substances Data)

Usage

Description

Amorolfine hydrochloride is the first morpholine antifungal agent useful in the topical treatment of onychomycosis. Mechanistically, it appears to inhibit two stages of the ergosterol biosynthetic pathway, which is necessary for fungal cell viability. Active against a broad spectrum of fungi, amorolfiie hydrochloride is particularly effective against yeasts such as Histoplasma capsulatum, dermatophytes and dematiaceous fungi.

Chemical Properties

Liquid

Uses

Different sources of media describe the Uses of 78613-38-4 differently. You can refer to the following data:
1. Amorolfine hydrochloride has been used as an antifungal agent.
2. antihypertensive

Definition

ChEBI: A hydrochloride resulting from the formal reacton of equimolar amounts of hydrogen chloride and amorolfine. An inhibitor of the action of squalene monooxygenase, Delta14 reductase and D7-D8 isomerase and an antifungal ag nt, it is used for the topical treatment of fungal nail and skin infections.

Biochem/physiol Actions

Amorolfine is a broad-based antifungal agent with fungicidal effects against most fungi, dermatophytes and yeasts. Amorolfine blocks ergosterol biosynthesis by interfering with delta 14 reduction and the delta 7-8 isomerisation.

Upstream product

• 78613-35-1 amorolfine 
• 288583-04-0 amorolfine 
• 141-91-3 cis-2,6-dimethylmorpholine 
• 1895-97-2 2-methyl-3-phenylacrylic acid 
• 75-85-4 tert-Amyl alcohol 
• 922734-43-8 (2R,6S)-2,6-dimethyl-4-(2-methyl-3-phenylpropyl)morpholine hydrochloride 
• 67467-96-3 2-methyl-3-(4-(tert-pentyl)phenyl)propanal 
• 594-36-5 2-methyl-2-butylchloride 

Relevant articles and documents

Preparation method of amorolfine hydrochloride

The invention relates to the technical field of pharmaceutical preparations. The invention discloses a preparation method of amorolfine hydrochloride. The method comprises the following steps: with 3-(4-tert-amylphenyl)-2-methyl propanol as a raw material, under alkaline condition, performing a reaction on the raw material with methylsulfonyl chloride and performing nucleophilic substitution reaction with cis-2,6-dimethylmorpholine; and finally performing a reaction with hydrogen chloride gas to form the amorolfine hydrochloride, that is, the final product. According to the present invention,the method has advantages of cheap raw material source, easily-controlled process operation, high yield, stable quality, less impurity, significantly-reduced cost compared to other methods, suitability for industrial production, and the like.

Amorolfine hydrochloride preparation method

The invention provides an amorolfine hydrochloride preparation method which specifically comprises the following steps: putting a compound of formula IIa shown in the specification into an organic solvent, further putting an amidation catalyst, carrying out a stirring reaction, further adding cis-2,6-dimethyl morpholine, and carrying out a reaction so as to obtain a compound III; carrying out backflow stirring on the compound III in absolute methanol, adding magnesium chips in batches, and carrying out a reaction so as to obtain a compound IV; carrying out a reaction on the compound IV under the action of a reducing agent, thereby obtaining a compound V. The method is novel in process route, cheap and easy in raw material obtaining, low in cost, simple in process operation, short in production cycle, gentle in reaction condition, high in yield, good in product quality and applicable to industrial production.

Process of producing amorolfine

The present invention refers to an improved process of producing Amorolfine base, which is a compound of formula (I): said process comprising the steps of: (i) contacting a compound of formula (II): with a Friedel-Crafts catalyst; and (ii) adding one equivalent of 2-halogeno-2-methylbutane, characterised in that the reaction mixture obtained in step (i) is cooled to a temperature between -40 to -60 °C prior to step (ii) and the Friedel-Craft catalyst is chosen among the group consisting of boron trifluoride complex, titanium chloride complex, zinc chloride, gallium chloride, antimony pentafluoride, molybdenum pentachloride, indium chloride, antimony pentachloride, lanthanide bromide, scandium(III)triflate, lanthanide (III) triflate, yterbium (III) triflate and silica gel associated with ferric chloride.