73954-34-4

Usage

Uses

Used in Pharmaceutical Industry:
N-(2,2-Dimethoxyethyl)-3,4-dimethoxyphenylacetamide is used as an impurity in the production of Ivabradine (I940500) for the treatment of angina pectoris. Its presence, although as an impurity, is significant in the context of the manufacturing process and quality control of the medication. N-(2,2-dimethoxy-ethyl)-3,4-dimethoxyphenylacetamide's role in the pharmaceutical industry is primarily related to its association with Ivabradine, a selective bradycardic agent that targets the sinoatrial node's pacemaker If current, providing a direct effect on heart rate regulation.

Upstream product

• 10313-60-7 3,4-dimethoxyphenylacetyl chloride 
• 22483-09-6 2,2-dimethoxyethylamine 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 93-17-4 3,4-dimethoxyphenylacetonitrile 
• 5663-56-9 2-(3,4-dimethoxyphenyl)acetamide 

Downstream Products

• 1174715-26-4 N-(3,4-dimethoxyphenethyl)-2,2-dimethoxyethanamine 
• 1104967-34-1 3-[2-(3,4-dimethoxyphenyl)ethyl]-7,8-dimethoxy-1,3-dihydrobenzo[d]azepin-2-one 
• 148870-57-9 7,8-dimethoxy-3-[3-iodopropane]-1,3-dihydro-2H-3-benzazepin-2-one 
• 20925-64-8 7,8-dimethoxy-2-oxo-2,3,4,5-tetrahydro-1H-3-benzazepine 
• 85177-13-5 1-[7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl]-3-[N-methyl-N-(2-{4-methoxy-phenyl}-ethyl)-amino]-propane 
• 96255-08-2 3-(3-{[2-(4-Chloro-phenyl)-ethyl]-methyl-amino}-propyl)-7,8-dimethoxy-1,3,4,5-tetrahydro-benzo[d]azepin-2-one 
• 96255-09-3 3-(3-{[2-(4-Hydroxy-phenyl)-ethyl]-methyl-amino}-propyl)-7,8-dimethoxy-1,3,4,5-tetrahydro-benzo[d]azepin-2-one 
• 125846-58-4 3-(3-{Bis-[2-(3,4-dimethoxy-phenyl)-ethyl]-amino}-propyl)-7,8-dimethoxy-1,3,4,5-tetrahydro-benzo[d]azepin-2-one 
• 85176-57-4 1-[7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl]-3-[N-ethoxycarbonyl-N-(2-{3,4-dimethoxy-phenyl}-ethyl)-amino]-propane 
• 125846-61-9 3-{3-[2-(3,4-Dimethoxy-phenyl)-ethanesulfonyl]-propyl}-7,8-dimethoxy-1,3,4,5-tetrahydro-benzo[d]azepin-2-one 
• 85176-56-3 1[7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl]-3-[N-acetyl-N-(2-{3,4-dimethoxy-phenyl}-ethyl)-amino]-propane 
• 125846-60-8 3-{3-[2-(3,4-Dimethoxy-phenyl)-ethanesulfinyl]-propyl}-7,8-dimethoxy-1,3,4,5-tetrahydro-benzo[d]azepin-2-one 
• 102247-09-6 N-[3-(7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl)-propyl]-N-[3-(3,4-dimethoxyphenylamino)-propyl]-methylamine 

Relevant academic research and scientific papers

Design of oxa-spirocyclic PHOX ligands for the asymmetric synthesis of lorcaserin: Via iridium-catalyzed asymmetric hydrogenation

Phosphine-oxazoline (PHOX) ligands are a very important class of privileged ligands in asymmetric catalysis. A series of highly rigid oxa-spiro phosphine-oxazoline (O-SIPHOX) ligands based on O-SPINOL was synthesized efficiently, and their iridium complexes were synthesized by coordination of the O-SIPHOX ligands to [Ir(cod)Cl]2 in the presence of sodium tetrakis-3,5-bis(trifluoromethyl)phenylborate (NaBArF). The cationic iridium complexes showed high reactivity and excellent enantioselectivity in the asymmetric hydrogenation of 1-methylene-tetrahydro-benzo[d]azepin-2-ones (up to 99% yield and up to 99% ee). A key intermediate of the anti-obesity drug lorcaserin could be efficiently synthesized using this protocol.

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.

PROCESS FOR THE PREPARATION OF BENZAZEPINE-2-ONE DERIVATIVE

The present, invention relates to a cost effective, environment friendly industrially viable process for the preparation of 7,8-dimethoxy-1,3-dihydro-2H-3-benzazepine-2-one, an intermediate used in the preparation of ivabradine, without using acid chloride intermediate and condensing agent.

PROCESS FOR THE SYNTHESIS OF BENZAZEPINE DERIVATIVES

Process for the synthesis of benzazepine derivatives The invention relates to a process for the synthesis of 7,8-dimethoxy-1,3-dihydro- benzazepin-2-one of formula (II), as well as to a process for the synthesis of compound of formula (I).

Functional reversal of (?)-Stepholidine analogues by replacement of benzazepine substructure using the ring-expansion strategy

(?)-Stepholidine is an active ingredient of the Chinese herb Stephania and naturally occurring tetrahydroprotoberberine alkaloid with mixed dopamine receptor D1 agonistic and dopamine receptor D2 antagonistic activities. In this work, a series of novel hexahydrobenzo[4,5]azepino [2,1-a]isoquinolines were designed and synthesized as ring-expanded analogues of (?)-Stepholidine. Initial pharmacological assays demonstrated that a benzazepine replacement was associated with significant increase in selectivity and functional reversal at dopamine receptor D1. Compound-(?)-15e (Ki?=?5.32?±?0.01?nm) is more potent than (?)-Stepholidine (Ki?=?13?nm) and was identified as a selective dopamine receptor D1 antagonist (IC50?=?0.14?μm). Moreover, molecular modeling suggested that (?)-15e might exert its dopamine receptor D1 antagonistic activities through interacting with the transmembrane helix 7 of dopamine receptor D1.

Synthesis and biological activity of some 1,3-dihydro-2H-3-benzazepin-2- ones with a piperazine moiety as bradycardic agents

A series of 1,3-dihydro-2H-3-benzazepin-2-ones with a piperazine moiety were designed and synthesized by treating the common intermediate of 1,3-dihydro-7,8-dimethoxy-3-[3-(1-piperazinyl)-propyl]-2H-3-benzazepin-2-ones with a variety of N-aryl-2-chloroacetamides and acyl chlorides. Their structures have been characterized by 1H-NMR, MS, and elemental analysis. The title compounds were evaluated for their bradycardic activity in vitro. Most of the synthesized compounds exhibited some vasorelaxant activity and heart-rate-reducing activity with bradycardic potency.

PROCESS FOR PREPARATION OF IVABRADINE

The present invention describes a new process for optical resolution of [N-[[3,4- dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl]-N-methylamine] which is an intermediate in the preparation of ivabradine.

A new synthetic approach towards isoquinobenzazepinone and isoindolinobenzazepinone using acid-mediated cyclisation and Heck reaction

Six-membered ring cyclisation of N-ethylbenzazepinone, prepared from the condensation of benzazepinone with phenethyl iodide under basic conditions, smoothly provided the corresponding product, isoquino[1,2-b][3]benzazepinone, under acid-mediated conditions. On the other hand, the attempted direct five-membered ring cyclisation using the acid-mediated conditions failed to give the 7,5 fused ring isoindolinobenzazepinone from N-benzylbenzazepinone, but the 7,6 fused ring product was instead obtained. However, five-membered ring cyclisation of N-benzylbenzazepinone could be effected efficiently by employing the Heck reaction followed by catalytic hydrogenation to furnish the desired isoindolinobenzazepinone.

HETEROCYCLIC AMIDE COMPOUNDS AS PROTEIN KINASE INHIBITORS

The present invention related to novel heterocyclic amide compounds of Formula 1: as disclosed herein or a pharmaceutically accept able salt, solvate, ester, prodrug or stereoisomer thereof. Also disclosedare compositions comprising said compounds, and methods for using said compounds for treating or preventing a proliferative disease, an anti-proliferative disorder, inflammation, arthritis, a neurological or neurodenerative disease, a cardiovascular disease, alopecia, a neuronal disease, an ischemic injury, a viral disease or a fungal disease

Process for the synthesis of 7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one, and application in the synthesis of ivabradine and addition salts thereof with a pharmaceutically acceptable acid

Process for the synthesis of the compound of formula (I): Application in the synthesis of ivabradine, addition salts thereof with a pharmaceutically acceptable acid and hydrates thereof.