139525-77-2

Usage

Uses

Used in Pharmaceutical Industry:
2-(7-Methoxy-1-naphthyl)ethylamine hydrochloride is used as a reagent for the synthesis of antidepressant agomelatine through a tandem allylic chlorination-isomerization process. 2-(7-Methoxy-1-naphthyl)ethylamine hydrochloride plays a crucial role in the development of novel antidepressant medications, which can help alleviate symptoms of depression and improve the quality of life for patients.
Additionally, 2-(7-Methoxy-1-naphthyl)ethylamine hydrochloride is used as a reagent in the design, preparation, and in vitro evaluation of melatonin derivatives as serotonin N-acetyltransferase inhibitors. These derivatives have the potential to regulate the sleep-wake cycle and improve sleep quality, making them valuable in the treatment of sleep disorders and circadian rhythm disturbances.
Furthermore, 2-(7-Methoxy-1-naphthyl)ethylamine hydrochloride is also known as Agomelatine Impurity 5, which is an impurity found in the synthesis process of agomelatine. The identification and control of such impurities are essential for ensuring the safety, efficacy, and quality of the final pharmaceutical product.

InChI:InChI=1/C13H15NO.ClH/c1-15-12-6-5-10-3-2-4-11(7-8-14)13(10)9-12;/h2-6,9H,7-8,14H2,1H3;1H

Upstream product

• 138113-09-4 2-(7-methoxynaphth-1-yl)ethylamine 
• 1424944-38-6 8-(2-chloroethyl)naphthalen-2-yl acetate 
• 58150-14-4 1-(2-chloroethyl)-7-methoxynaphthalene 
• 135-19-3 β-naphthol 
• 1331868-98-4 1-(2-chloroethyl)-7-hydroxynaphthalene 
• 1424944-39-7 N-formyl-N-(2-(7-methoxynaphthalen-1-yl)ethyl)formamide 
• 1424944-37-5 1-chloroacetyl-7-acetoxynaphthalene 
• 1523-11-1 naphthalen-2-yl acetate 
• 1617524-06-7 Tert-butyl (2-(7-methoxynaphthalen-1-yl)ethyl)carbamate 
• 91962-80-0 (7-methoxynaphthalen-1-yl)methanol 
• 185330-87-4 3-(7-methoxynaphthalen-1-yl)propanoic acid 
• 21568-72-9 7-methoxy-1-vinyl-1,2,3,4-tetrahydronaphthalen-1-ol 
• 6836-20-0 ethyl (7-methoxy-1,2,3,4-tetrahydro-1-naphthalenylidene)acetate 
• 63319-95-9 [7-Methoxy-3,4-dihydro-2H-naphthalen-(1E)-ylidene]-acetic acid 

Downstream Products

• 138112-91-1 S 20254 
• 138112-87-5 S 20253 
• 138112-80-8 S 20303 
• 138112-76-2 agomelatine 
• 138112-99-9 N-[2-(7-Methoxynaphth-1-yl)Ethyl]-Butyramide 
• 138113-13-0 N-[2-(7-methoxy-1-naphthyl)ethyl]cyclobutanecarboxamide 
• 138112-82-0 N-[2-(7-methoxynaphth-1-yl)ethyl]-4chlorobutyramide 
• 138112-84-2 S 20251 
• 1363155-79-6 N-(2-[7-methoxy-3-(4-methoxy-benzylamino)-naphthalen-1-yl]ethyl)acetamide 
• 1363156-07-3 N-[2-(3-cyclohexylmethyl-7-methoxy-naphthalen-1-yl)ethyl]acetamide 
• 1363156-02-8 N-[2-(3-cyclohexanecarbonyl-7-methoxy-naphthalen-1-yl)ethyl]acetamide 
• 1363155-75-2 2-(benzylmethylamino)-N-[2-(-7-methoxy-naphthalen-1-yl)ethyl]acetamide 
• 1096252-78-6 N-(2-{7-[(4-methoxybenzyl)amino]naphth-1-yl}ethyl)acetamide 
• 1176316-99-6 Agomelatine hydrochloride 

Relevant academic research and scientific papers

PROCESS FOR THE PREPARATION OF AGOMELATINE IN CRYSTALLINE FORM

The present invention pertains to a process for the preparation of polymorph form X of agomelatine, which comprises providing agomelatine, and crystallizing agomelatine in the presence of at least one of an acid and a salt thereof, and to a polymorph form of agomelatine.

2 - (7 - Methoxy -1 - naphthyl) ethylamine preparation method

The invention provides a preparation method of 2-(7-methoxy-1-naphthyl) ethylamine. The preparation method is characterized in that the raw material 4-toluene sulfonic acid1-(cyano methyl)-7-methoxynaphthalene-2-ester is reduced into the 2-(7-methoxy-1-naphthyl) ethylamine, a reducing agent used by the method is BH(OR)2, and R is propoxy or isopropoxy. The preparation method is few in reaction steps, high in yield, high in product purity and simple in post-processing.

Preparation method of Agomelatine

The invention relates to a preparation method of Agomelatine. The preparation method comprises the steps of directly reducing a raw material 4-methylbenzenesulfonic acid 1-(cyano methyl)-7-methoxynaphthalene-2-estoral into 2-(7-methoxyl-1-naphthyl) ethylamine, and then further transforming into the Agomelatine. The preparation method of the Agomelatine provided by the invention is less in reaction step, high in yield/purity, and simple in aftertreatment.

PROCESS FOR THE PREPARATION OF AGOMELATINE

The present invention relates to a method for economically and efficiently manufacturing agomelatine used as a medicine of depression, and a novel intermediate therefor. The manufacturing method comprises the steps of: (i) converting a hydroxy group of (7-methoxynaphthalene-1-yl)methanol of chemical formula II into a leaving group to obtain a compound of chemical formula III; (ii) coupling-reacting a compound of chemical formula IV or a compound of chemical formula V with the compound of chemical formula III, performing decarboxylation on the same, and obtaining 3-(7-methoxynaphthalene-1-yl)propanoic acid of chemical formula VI; (iii) performing Curtius rearrangement on the 3-(7-methoxynaphthalene-1-yl)propanoic acid of chemical formula VI, and obtaining 2-(7-methoxynaphthalene-1-yl)ethanamine of chemical formula VII; and (iv) performing an acetylization reaction on the 2-(7-methoxynaphthalene-1-yl)ethanamine of chemical formula VII.

A NOVEL PROCESS FOR THE PREPARATION OF TETRALIN AND NAPHTHALENE DERIVATIVES

The present invention relates to a novel process for the preparation or tetralin and naphthalene derivatives, including Agomelatine and pharmaceutical acceptable salts thereof. Such compounds are considered to be interesting either as useful building blocks or due to their biological activity.

Simple and Efficient Process for the Large-Scale Preparation of Agomelatine: An Antidepressant Drug

A simple and efficient process for the large-scale preparation of agomelatine (1), an antidepressant drug is, described. Agomelatine was prepared in a linear manner starting from readily available, inexpensive 2-naphthol. Key steps in the synthesis are Friedel-Crafts acylation of 2-naphthyl acetate with chloroacetyl chloride, reduction of keto intermediate, and nucleophilic displacement of chloro intermediate with sodium diformylamide. A systemic approach was described to streamline the process into a robust scalable process by controlling the impurities.

PROCESS FOR PREPARATION OF AGOMELATINE AND CRYSTALLINE FORM I THEREOF

An improved process for the preparation of agomelatine of formula (I) and a new process for the preparation of crystalline form I of agomelatine are provided.

AN IMPROVED PROCESS FOR PREPARATION OF AGOMELATINE

The present invention provides an improved process for preparing agomelatine of formula (I). The process comprises reacting 7-methoxy tetralone with cyanoacetic acid in an organic solvent to obtain (7-methoxy-3,4-dihydro- 1 -naphthalenyl)acetonitrile of Formula (B); treating compound of Formula (B) with a catalyst to obtain (7-methoxy- 1 - naphthyl)acetonitrile of Formula (C); reducing compound of formula (C) with hydrogen in presence of Raney nickel in ammoniacal methanol medium and subsequently converting to a salt using hydrochloric acid to obtain 2-(7-methoxy- 1 -naphthyI)ethanamine hydrochloride of formula (D); iv) reacting compound of formula (D) with acetic anhydride or acetic chloride in an organic solvent in presence of a base and a catalyst to obtain agomelatine of Formula (I); and optionally purifying agomelatine of Formula (I). The present invention also provides a process for preparing polymorphic Form-I of agomelatine of formula (I) comprising treating agomelatine of formula (I) in a suitable organic solvent; and isolating polymorphic Form-I of agomelatine of formula (I).

PROCESS FOR THE PREPARATION OF AGOMELATINE

The present invention provides a process for the preparation of agomelatine and its intermediate compounds. The invention also provides an intermediate compound of agomelatine represented by Formula (V).

Synthesis and biological evaluation of novel naphthalene compounds as potential antidepressant agents

In this study, a series of novel naphthalene compounds were synthesized and screened for their antidepressant-like activities in vitro and in vivo. Their values for two descriptors (ClogP, tPSA) of the blood-brain barrier (BBB) were calculated for early assessment of the central nervous system (CNS) drug-likeness. Seven of them (6d, 6i, 6k, 6o, 6p, 6s and 6t) demonstrated potential protective effects on corticosterone-induced lesion of PC12 cells although they cannot repair the irreversible oxidant injury to PC12 cells by hydrogen peroxide. Compounds with promising neurorestorative activities (6k, 6o and 6p) were further evaluated for their in vivo effects by forced swim test (FST) and open field test (OFT) in C57 mice models. The FST results showed that compounds 6k, 6o and 6p remarkably reduced the immobility time of the tested mice. Among them, compound 6k was the most potent one, much more effective than Agomelatine and comparable to Fluoxetine. The OFT results showed that mice treated with compound 6k traveled a longer distance than those treated with Agomelatine or Fluoxetine, indicating a better general locomotor activity. The paper also proposed a possible binding mode of compound 6k with glucocorticoid receptor by docking study. The in vitro cytotoxicity data on HEK293 and L02 cells suggested compound 6k to be a promising antidepressant candidate for subsequent investigation.