3246-03-5

Usage

Chemical Properties

Yellow Syrup

Uses

Intermediate in the preparation of Carvedilol derivatives.

Upstream product

• 4463-59-6 2-(methoxyphenoxy)ethylbromide 
• 100-46-9 benzylamine 
• 1836-62-0 2-(2-methoxy-phenoxy)-ethylamine 
• 100-39-0 benzyl bromide 
• 100-52-7 benzaldehyde 
• 53815-60-4 1-(2-chloroethoxy)-2-methoxybenzene 
• 90-05-1 2-methoxy-phenol 
• 121496-39-7 N-(tert-butoxycarbonyl)-N-benzylethanolamine 
• 204122-21-4 N-[2-(2-methoxyphenoxy)ethyl]-N-benzylcarbamic acid tert-butyl ester 

Downstream Products

• 85320-68-9 amosulalol 
• 81748-66-5 5-{1-Hydroxy-2-[2-(2-methoxyphenoxy)ethylamino]ethyl}-2-methoxybenzenesulfonamide 
• 70959-72-7 5-{1-Hydroxy-2-[2-(2-methoxy-phenoxy)-ethylamino]-propyl}-2-methoxy-benzenesulfonamide 
• 245762-95-2 N-benzyl-3-(1H-indol-3-yl)-N-[2-(2-methoxyphenoxy)ethyl]propionamide 
• 245762-23-6 N-benzyl-4-(1H-indol-3-yl)-N-[2-(2-methoxyphenoxy)ethyl]butyramide 
• 245762-28-1 N-[3-(5-fluoro-1H-indol-3-yl)propyl]-N-[2-(2-methoxyphenoxy)ethyl]benzylamine 
• 1198090-72-0 1-(benzyl(2-(2-methoxyphenoxy)ethyl)amino)-3-(4-(3-(benzyl(2-(2-methoxyphenoxy)ethyl)amino)-2-hydroxypropoxy)-9H-carbazol-9-yl)propan-2-ol 
• 72955-94-3 1-[benzyl[2(2-methoxyphenoxy)ethyl]amino]-3-(9H-carbazol-4-yloxy)propan-2-ol 
• 245762-25-8 benzyl-[4-(1H-indol-3-yl)butyl]-[2-(2-methoxyphenoxy)ethyl]amine 
• 245762-24-7 benzyl-[3-(1H-indol-3-yl)propyl]-[2-(2-methoxyphenoxy)ethyl]amine 
• 3243-96-7 N-<2-(2-Methoxy-phenoxy)-ethyl>-N-<3-(2,5-dimethoxy-phenoxy)-propyl>-benzylamin 
• 81748-67-6 2-Hydroxy-5-{1-hydroxy-2-[2-(2-methoxyphenoxy)ethylamino]-ethyl}benzenesulfonamide 

Relevant academic research and scientific papers

Novel acetylcholinesterase inhibitory derivatives, preparation method thereof, and pharmaceutical composition for use in preventing or treating nervous system diseases containing the same as an active ingredient

The present invention relates to a novel acetylcholinesterase inhibiting derivative, a production method thereof, and a pharmaceutical composition for preventing or treating neurological disease containing the same as an active ingredient. The compound, a

Synthesis and characterization of potential impurities of carvedilol, an antihypertensive drug

Carvedilol (Coreg) is a nonselective -adrenergic blocking agent with vasodilating activity. It is used for the treatment of congestive heart failure and hypertension. During the bulk synthesis of carvedilol, we have observed six impurities: Imp-I, Imp-II, Imp-III, Imp-IV, Imp-V, and Imp-VI. The present work describes the synthesis and characterization of these impurities. Copyright

Synthesis of impurity A in Carvedilol: a β-adrenergic receptor

Carvedilol is prepared by different synthetic approaches. Almost in all the approaches the major impurities that are known in the literature A, B, C, D and E are listed in European pharmacopoeia. The control of pharmaceutical impurities is currently a critical issue to the pharmaceutical industry. In this publication, a description of these impurities and their origins in Carvedilol process are presented along with the preparation of impurity A.

Studies toward the discovery of the next generation of antidepressants. 3. Dual 5-HT1A and serotonin transporter affinity within a class of N-aryloxyethylindolylalkylamines

N-Aryloxylethylindolealkylamines (5) having dual 5-HT transporter and 5-HT1A affinity are described. These compounds represent truncated analogues of our previously reported piperidinyl derivatives (3). Compounds in this investigation were found to have more similar affinities and functional activities for the 5-HT1A receptor and 5-HT transporter. Though 5-HT1A antagonism is not consistently observed throughout series 5, several molecular features were found to be essential to obtain high and balanced activities. The proper placement of a heteroatom in the aryl ring and the length of the linkage used to tether the indole moiety had significant influence on 5-HT1A and 5-HT transporter affinities. Introduction of a halogen into the aryl ring usually lowered intrinsic activity and in some cases led to full 5-HT1A antagonists. Compounds 33 and 34 were observed to be full 5-HT1A antagonists with Ki values of approximately 30 nM for the 5-HT1A receptor and Ki values of 5 and 0.5 nM for the 5-HT transporter, respectively. Unfortunately, similar to our previous series (3), compounds in this report also had high affinity for the α1 receptor.

Process and intermediates for preparing 1-[9'H-carbazol-4'-yloxy]-3-[ 2''-(2'''- methoxy -phenoxy)-ethyl)-amino]-propan-2-ol[carvedilol]

A subject matter of the invention is a process for preparing 1-[9'H-carbazol-4'-yloxy]-3-[{2''-(2'''--phenoxy)- ethyl}-amino]-propan-2-ol as well as the R or S enantiomer thereof and mixtures of the enantiomers and acid addition salts of these compounds, in which a) 4-(oxiranylmethoxy)-9H-carbazole or the R or S enantiomer thereof is reacted with N-[2-(2'--phenoxy)-ethyl] -benzylamine in a protic organic solvent, and the thus formed 1-[N-{benzyl}-2'-({2''--phenoxy)-ethyl}-amino]-3-[9'''H-carbazol-4'''-yloxy] -propan-2-ol [benzyl-carvedilol] is debenzylated by catalytic hydrogenation or b) the N-[2-(2'--phenoxy) -ethyl]-benzylamine is reacted with epichlorohydrin, the thus formed 1-[N-{benzyl}-2'-({2''--phenoxy)-ethyl}-amino]-3-[chloro] -propan-2-ol is reacted with 4-(hydroxy)-9H-carbazole and the thus formed 1-[N-{benzyl}-2'-({2''--phenoxy)-ethyl}- amino]-3-[9'''H-carbazol-4'''-yloxy]-propan-2-ol is debenzylated by catalytic hydrogenation