148849-68-7

Basic information

• Product Name: ent-Ivabradine Hydrochloride
• Synonyms: ent-Ivabradine Hydrochloride;Ivabradine R-Isomer HCl;3-[3-[[[(7R)-3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl]methylamino]propyl]-1,3,4,5-tetrahydro-7,8-dimethoxy-2H-3-benzazepin-2-one;Ivabradine R-Isomer hydrochloride
• CAS NO: 148849-68-7
• Molecular Formula: C27H37ClN2O5
• Molecular Weight: 505.04608
• Mol File: 148849-68-7.mol
• Article Data: 24

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ent-Ivabradine Hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: ent-Ivabradine Hydrochloride(148849-68-7)
• EPA Substance Registry System: ent-Ivabradine Hydrochloride(148849-68-7)

Safety Data

• Hazardous Substances Data: 148849-68-7(Hazardous Substances Data)

Usage

Description

Ent-Ivabradine Hydrochloride is a chemical compound that serves as an impurity in the synthesis of Ivabradine, a selective bradycardic agent with a direct effect on the pacemaker If current of the sinoatrial node. It is also known for its antianginal properties.

Uses

Used in Pharmaceutical Industry:
Ent-Ivabradine Hydrochloride is used as an impurity in the synthesis of Ivabradine for its role in the development of medications that target heart rate regulation and心绞痛 (angina) relief. Its presence in the synthesis process is crucial for the production of Ivabradine, which is a selective bradycardic agent that directly affects the pacemaker If current of the sinoatrial node, contributing to its antianginal properties.
Additionally, it is important to note that Ent-Ivabradine Hydrochloride is an impurity in the synthesis of 3,3''-(Propane-1,3-diyl)bis(7,8-dimethoxy-4,5-dihydro-1H-benzo[d]azepin-2(3H)-one) (P760340), which is another compound with potential applications in the pharmaceutical industry.

Upstream product

• 866783-13-3 1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride 
• 85175-65-1 7,8-dimethoxy-3-(3-chloropropyl)-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one 
• 1031767-75-5 [{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine d-camphorsulfonate 
• 93-17-4 3,4-dimethoxyphenylacetonitrile 
• 5663-56-9 2-(3,4-dimethoxyphenyl)acetamide 
• 148870-56-8 ({3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl)(methyl)amine 
• 73344-75-9 (±)-(3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methylamine 
• 73954-34-4 N-(2,2-dimethoxy-ethyl)-3,4-dimethoxyphenylacetamide 
• 73942-87-7 7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 866783-12-2 [{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine 
• 3144-16-9 (1S)-10-camphorsulfonic acid 
• 155974-00-8 ivabradine 
• 866462-51-3 3-[2-(1,3-Dioxolan-2-yl)-ethyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one 

Downstream Products

• 155974-00-8 ivabradine 
• 1462470-54-7 {2-[2-({3-[{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-4,3,5-trien-7-yl]methyl}(methyl)-amino]propyl}amino)ethyl]-4,5-dimethoxyphenyl}acetic acid 

Relevant articles and documents

Exploiting the Biocatalytic Toolbox for the Asymmetric Synthesis of the Heart-Rate Reducing Agent Ivabradine

Several chemoenzymatic routes have been evaluated for the production of the heart-rate reducing agent ivabradine. Lipases and ω-transaminases have been identified as useful biocatalysts for the preparation of key enantiopure precursors. The lipase-catalysed kinetic resolution by alkoxycarbonylation of a racemic primary amine and subsequent chemical reduction of the resulting carbamate provided an N-methylated (S)-amine, one step away from ivabradine. Alternatively, the dynamic kinetic resolution by asymmetric bioamination of an aldehyde precursor enabled, in a four-step sequence, the preparative scale synthesis of enantiopure ivabradine in 50% overall yield. (Figure presented.).

AN IMPROVED PROCESS FOR THE SYNTHESIS OF IVABRADINE AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS

: Disclosed herein is an improved process for the preparation of Ivabradine and pharmaceutically acceptable salts thereof. The invention more particularly disclosesthe synthesis of key intermediates viz.,(S)-N-[(4,5-dimethoxybenzocydobut-l-yl)-methyl]-N- (methyl)amine hydrochloride of Formula-II and 3-(3-Iodopropyl)-7,8-dimethoxy-1,3-dihydro-2H-3-benzapin-2-one of Formula-III, and its use in industrial synthesis of Ivabradine and pharmaceutically acceptable salts thereof.

A high-purity hydrochloric acid Ivabradine preparation method (by machine translation)

The invention discloses a high-purity hydrochloric acid Ivabradine preparation method, the method after the nucleophilic substitution, catalytic hydrogenation, into the hydrochloric acid salt of three-step reaction, the preparation of the hydrochloride of ivabradine, wherein the use of bicarbonate solution to wash the dehydrogenation Ivabradine solution to remove most of the un-reacted compound II, to avoid a column chromatography operation, the operation is simple; at the same time, the way using atmospheric pressure of hydrogenation, does not need to use high-pressure hydrogenation cauldron, also non-blocking condenser risk, safe operation; the resulting salts are acid Ivabradine purity to be 99.8%, most large [...]0.10%, does not need to re-refining can achieve the standard of the raw material, the reaction route is as follows. (by machine translation)