794466-70-9

Usage

Uses

Used in Cardiology:
Vernakalant is used as an antiarrhythmic agent for the treatment of atrial fibrillation. It helps to restore and maintain normal heart rhythm by blocking the potassium channels involved in the irregular electrical activity of the heart.
Used in Pharmaceutical Industry:
Vernakalant is used as a drug candidate for the development of new treatments for cardiac arrhythmias. Its atrial selectivity and ability to reduce side effects make it a promising option for the management of atrial fibrillation and potentially other related conditions.

Pharmacological action

Venakaran works by blocking peak sodium currents by blocking overdrive-activated delayed rectifier currents (IKur). IKur, encoded by the Kv1.5 channel protein, is abundantly expressed in atrial myocytes, is the main current mediating atrial repolarization in humans, and is activated during atrial fibrillation. Venakalan inhibition of IKur can prolong the action potential duration of the atrium, thereby prolonging the atrial effective refractory period and slowing down atrial conduction, so as to shorten the time of atrial fibrillation and quickly achieve the effect of atrial fibrillation conversion.

Originator

Cardiome Pharma Corp. (Canada)

Upstream product

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• 1370354-69-0 C₂₇H₃₅NO₅ 
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• 906802-36-6 (3R)-1-(2-(3,4-dimethoxyphenethoxy)cyclohexyl)-2,5-dioxopyrrolidin-3-yl acetate 
• 795281-92-4 (3R)-3-benzyloxy-1-{(1R,2R)-2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexyl}pyrrolidine 

Downstream Products

• 748810-28-8 Vernakalant hydrochloride 

Relevant academic research and scientific papers

A method for preparing weinaweina kalland hydrochloride (by machine translation)

The invention discloses a method for preparing weinaweina kalland hydrochloride. The method to selectively amino protection, nucleophilic addition, nucleophilic substitution, deprotected, cyclized, reduction, into a salt by the reaction of the compound Wina carland hydrochloride. And after nuclear magnetic analysis test technology confirm its structure. It adopts the cheap and easily obtained starting materials to prepare, preparation method has advantages of simple operation, mild condition, easy industrialized production and the like, and avoids the use of heavy metal, is beneficial to the development of the oral. (by machine translation)

A highly efficient asymmetric synthesis of vernakalant

A novel synthesis of vernakalant is described. Using inexpensive and readily available reagents, the key transformations involve (1) an efficient zinc-amine-promoted etherification, (2) a highly stereoselective enzyme-catalyzed dynamic asymmetric transamination to set up the two contiguous chiral centers in the cyclohexane ring, and (3) a pyrrolidine ring formation via alkyl-B(OH)2-catalyzed amidation and subsequent imide reduction.

PROCESS FOR PREPARATION OF AMINOCYCLOHEXYL ETHERS AND INTERMEDIATE PRODUCTS USED IN THE PROCESS

A process for preparation of a compound of formula (I) or or a pharmaceutically acceptable salt, ester, or prodrug thereof, is disclosed. The process involves hydrogenating, in the presence of a catalyst, a compound of formula (II). The different substituents are as described in the specification. Also disclosed are intermediates and processes for their preparation. Further, the process can provide an alternate route for the synthesis of Vernakalant from starting materials that can be readily available.

PRODUCTION METHOD OF OPTICALLY ACTIVE CYCLOHEXANE ETHER COMPOUNDS

The present invention relates to an industrial synthetic method of an optically active cyclohexane ether compound (IIIa) or a salt thereof, which is useful as a pharmaceutical agent, and an intermediate useful for the production method of the present invention. The production method of the present invention is as shown below: wherein each symbol is as defined in the specification. According to the production method of the present invention, efficient and stable supply of an optically active cyclohexane ether compound (IIIa) in a high yield at a lower cost can be afforded. Therefore, an optically active cyclohexane ether compound (IIIa) extremely useful as a pharmaceutical agent can be provided by an industrially highly advantageous method.

SYNTHETIC PROCESS FOR AMINOCYCLOHEXYL ETHER COMPOUNDS

Methods for the preparation of stereoisomerically substantially aminocyclohexyl ether compounds such as trans-(1R,2R)-aminocyclohexyl ether compounds and/or trans-(1S,2S)-aminocyclohexyl ether compounds as well as various intermediates and substrates are disclosed.

SYNTHETIC PROCESSES FOR THE PREPARATION OF AMINOCYCLOHEXYL ETHER COMPOUNDS

This invention is directed to stereoselective synthesis of compounds of formula (I) or formula (II) or a pharmaceutically acceptable salt, ester, amide, complex, chelate, clathrate, solvate, polymorph, stereoisomer, metabolite or prodrug thereof; wherein R3, R4 and R5 are defined herein. Compounds of formula (I) and formula (II) are known to be useful in treating arrhythmias.