6781-17-5

Usage

Uses

Used in Pharmaceutical Industry:
2-(2-Ethoxyphenoxy)ethanamine is used as an impurity in the production of Tamsulosin, a medication specifically designed to treat benign prostatic hypertrophy (BPH). As an α1-adrenoceptor antagonist, Tamsulosin works by relaxing the muscles in the prostate and bladder neck, improving urine flow and reducing symptoms associated with BPH.

InChI:InChI=1/C10H15NO2/c1-2-12-9-5-3-4-6-10(9)13-8-7-11/h3-6H,2,7-8,11H2,1H3

Upstream product

• 153334-07-7 C₁₈H₁₇NO₄ 
• 94-71-3 2-Ethoxyphenol 
• 792931-60-3 2-(2-ethoxyphenoxy)acetamide 

Downstream Products

• 38752-73-7 4-[2-(2-ethoxyphenoxy)ethylamino]-1-(4-fluorophenyl)-1-butanol 
• 38752-72-6 N-[2-(2-ethoxyphenoxy)-ethyl]-3-(4-fluorobenzoyl)propionamide 
• 1220748-16-2 C₂₆H₂₉NO₄ 
• 882494-06-6 oxalate salt of tamsulosin 
• 1255188-24-9 2-(2-(benzyloxy)phenoxy)-N-(2-(2-ethoxyphenoxy)ethyl)acetamide 
• 852619-17-1 C₂₀H₂₆N₂O₅S 
• 56152-14-8 N-{2-(2-ethoxyphenoxy)ethyl}-3-(4-fluorophenoxy)propylamine hydrochloride 
• 80223-99-0 (+/-)-Tamsulosin hydrochloride 
• 103545-88-6 5-[2-(2-Ethoxy-phenoxy)-ethylamino]-2-isopropyl-2-(3,4,5-trimethoxy-phenyl)-pentanenitrile 
• 20640-17-9 2-<2-(o-Ethoxy-phenoxy)-ethylamino>-ethanthiol 
• 160970-14-9 1-acetyl-5-[2-[2-(2-ethoxyphenoxy)ethylamino]propyl]indoline-7-carbonitrile 

Relevant academic research and scientific papers

New serotonin 5-HT1A receptor agonists endowed with antinociceptive activity in vivo

We report the synthesis of new compounds 4-35 based on two different openings (A and B) of the chromane ring present in the previously identified 5-HT1A receptor (5-HT1AR) ligand 3. The synthesized compounds were assessed for binding affinity, selectivity, and functional activity at the 5-HT1AR. Selected candidates resulting from B opening were also evaluated for their potential antinociceptive effect in vivo and pharmacokinetic properties in vitro. Analogue 19 [2-(4-{[2-(2-ethoxyphenoxy) ethyl]amino}butyl)tetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione] has been characterized as a high-affinity and potent 5-HT1AR agonist (K i = 2.3 nM; EC50 = 19 nM). Pharmacokinetic studies indicated that compound 19 displays a good metabolic stability in human liver microsomes (t1/2 ～ 3 h and CLint = 3.5 mL/min/kg, at 5 μM), and a low level of protein binding (25%, at 5 μM). Interestingly, 19 (3 mg/kg, ip, and 30 mg/kg, po) caused significant attenuation of formalin-induced behavior in early and late phases of the mouse intradermal formalin test of pain, and this in vivo effect was reversed by the selective 5-HT1AR antagonist WAY-100635. Thus, the new 5-HT1AR agonist identified in this work, 19, exhibits oral analgesic activity, and the results herein represent a step toward identifying new therapeutics for the control of pain.

Discovery of a new series of 5-HT1A receptor agonists

Starting from compounds previously identified as α1-adrenoceptor antagonists that were also found to bind to the 5-HT1A receptor, in an attempt to separate the two activities, a new series of 5-HT1A receptor agonists was identified and shown to have high potency and/or high selectivity. Of these, compound 13, which combines high selectivity (5-HT1A/α1 = 151) and good agonist potency (pD2 = 7.82; Emax = 76), was found to be the most interesting.

PREPARATION OF 2-(2-ALKOXY PHENOXY) ETHYLAMINE, AN INTERMEDIATE OF CARVEDILOL AND TAMSULOSIN

The present patent application relates to a process for the preparation of 2-(2-Alkoxy phenoxy) ethylamine or a salt thereof, which is a useful intermediate in the preparation of several active pharmaceutical ingredients including Carvedilol and Tamsulosin. It also provides 2-(2-methoxy phenoxy) ethylamine in solid form.

METHOD FOR PREPARING 2-ALKOXYPHENOXYETHANAMINES FROM 2-ALKOXYPHENOXYETHYLACETAMIDES

The present invention relates to a method for preparing 2-Alkoxyphenoxyethanamines and more particularly relates to the preparation of the new chemical entity 2-Alkoxyphenoxyethylacetamides, in particular as intermediates in said method. An industrial process for the synthesis of 2-Alkoxyphenoxyethanamines which is cheap and easy to perform, is a long felt need for those skilled in the art. The object of the present invention is therefore to provide a process for the industrial production of phenoxyethanamine which is cheap and easy to perform. This object is solved by the new chemical entity 2-Alkoxyphenoxyacetamide which is prepared by reacting an ortho substituted phenol with a 2-Alkyloxazoline. By hydrolysis of the acetamide with water in the presence of organic or mineral acids such as hydrochloric acid and/or sulfuric acid, the 2-Alkylphenoxyethanamine is obtained.