375815-87-5

Usage

Uses

Used in Pharmaceutical Industry:
Varenicline tartrate is used as a prescription medication for treating smoking addiction. It acts as a nicotinic α4β2 acetylcholine receptor partial agonist, which aids in smoking cessation by reducing the pleasurable effects of smoking and decreasing withdrawal symptoms.
Used in Smoking Cessation Aids:
Varenicline tartrate is used as a smoking cessation aid to help individuals quit smoking. It works by partially activating the nicotinic a4? acetylcholine receptors, which helps to alleviate cravings and withdrawal symptoms associated with nicotine dependence.
Used in Research and Development:
Varenicline tartrate is also utilized in research and development for the study of nicotinic cholinergic receptors and their role in addiction and other related conditions. This knowledge can contribute to the development of new treatments and therapies for various nicotine-related disorders.

Biological Activity

Orally active, subtype-selective partial agonist at α 4 β 2 nicotinic receptors (K i values are 0.06, 240, 322 and 3540 nM for α 4 β 2, α 3 β 4, α 7, α 1 β γ δ receptors respectively). Reduces nicotine-evoked dopamine release in vitro and decreases nicotine self-administration in vivo .

Biochem/physiol Actions

Varenicline tartrate is a partial α4β2 nicotinic receptor agonist and α7 full agonist. Varenicline competitively binds to α4β2 receptors and partially stimulates without creating a full nicotine effect, while simultaneoudly blocking the ability of nicotine to bind to the receptors. Varenicline thus blocks the ability of nicotine to activate α4β2 receptors and stimulate the central nervous mesolimbic dopamine system, believed to be the neuronal mechanism underlying reinforcement and reward experienced upon smoking.

InChI:InChI=1/C13H13N3.C4H6O6/c1-2-16-13-5-11-9-3-8(6-14-7-9)10(11)4-12(13)15-1;5-1(3(7)8)2(6)4(9)10/h1-2,4-5,8-9,14H,3,6-7H2;1-2,5-6H,(H,7,8)(H,9,10)/t;1-,2-/m.0/s1

Upstream product

• 230615-70-0 1-(9,10-dihydro-6H-6,10-methanoazepino[4,5-g]quinoxaline-8(7H)-yl)-2,2,2,-trifluoroethanone 
• 87-69-4 L-Tartaric acid 
• 230615-69-7 1-(7,8-diamino-4,5-dihydro-1H-1,5-methanobenzo[d]azepin-3(2H)-yl)-2,2,2-trifluoroethanone 
• 249296-44-4 varenicline 

Relevant academic research and scientific papers

CRYSTALLINE FORMS OF NOVEL VARENICLINE SALTS, PREPARATION METHODS THEREOF AND PHARMACEUTICAL COMPOSITIONS COMPRISING THEREOF

The present invention refers to crystalline form of 7, 8, 9, 10 - tetrahydro - 6, 10 - methano - 6H - [3] [2, 3 a-h] pyrazole roh it cuts the person number pin new salt, and manufacturing method of including pharmaceutical compositions are disclosed. (by machine translation)

Process for Preparing Quinoxaline Derivatives

The present invention provides an improved process for preparing a compound of formula (IIIA), an intermediate of the synthesis of varenicline. Also, the present invention provides an improved process for preparing varenicline, or a pharmaceutically acceptable salt or solvate thereof. Furthermore, the present invention provides a process for decolorizing varenicline, or a salt or solvate thereof. Still further, the present invention provides a process of preparing varenicline L-tartrate with improved yield. Still further, the present invention relates to the use of compound of formula (V), or a salt or solvate thereof, as a reference marker and reference standard for assessing the purity of varenicline, or a salt or solvate thereof.

HIGHLY PURE VARENICLINE OR A PHARMACEUTICALLY ACCEPTABLE SALT THEREOF SUBSTANTIALLY FREE OF METHYLVARENICLINE IMPURITY

Provided herein is an impurity of varenicline, 6-methyl-5,8,14-triazatetracyclo[l 0.3.1.02'n,04'9]hexadeca-2(l l),3,5,7,9-pentaene (methylvarenicline) impurity, and a process for the preparation and isolation thereof. Provided further herein is a highly pure varenicline or a pharmaceutically acceptable salt thereof substantially free of methylvarenicline impurity, a process for the preparation thereof, and pharmaceutical compositions comprising highly pure varenicline or a pharmaceutically acceptable salt thereof substantially free of methylvarenicline impurity.

IMPROVED PROCESS FOR THE PREPARATION OF SUBSTITUTED QUINOXALINES

The present invention is directed to an improved process for the preparation of substituted quinoxalines by cyclization of the corresponding dianiline in the presence of ion exchange resin.

PROCESS FOR PREPARING VARENICLINE, VARENICLINE INTERMEDIATES, AND PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF

Provided herein is an improved, convenient, commercially viable and environmentally friendly process for the preparation of varenicline or a pharmaceutically acceptable salt thereof comprising reacting l-(4,5-diamino-10-aza-tricyclo[6.3.1.02 7]dodeca-2(7),3,5-trien- 10-yl)-2,2,2-trifluoro-ethanone with chloroacetaldehyde in the pressence of an oxygen source. Provided further herein is an improved and industrially advantageous process for the preparation of l-(4,5-diamino-10-aza-tricyclo[6.3.1.02 7]dodeca-2(7),3,5-trien-10-yl)-2,2,2- trifluoro-ethanone.

IMPROVED PROCESSES FOR THE SYNTHESIS OF VARENICLINE L-TARTRATE

This invention provides a process of preparing varenicline L-tartrate salt. This invention also provides varenicline L-tartrate produced by the instant method, as well as a pharmaceutical composition comprising same.

Preparations of new polymorphic forms of varenicline tartrate

The present invention is directed to an amorphous form, three novel polymorph form of crystalline varenicline tartrate, namely Form D, Form E and Form F. The present invention also provides processes of their preparations and pharmaceutical composition comprising such material and their use in therapy. Form D is new anhydrous varenicline tartrate, and can be prepared from recrystallizing varenicline tartrate in a mixture of methanol and water or a mixture of N,N-dimethylformamide and water. Form E is a new varenicline tartrate monohydrate, and can be prepared recrystallizing varenicline tartrate in a mixture of isopropanol and water. Form F is another new varenicline tartrate monohydrate, and can be prepared recrystallizing varenicline tartrate in a mixture of acetone and water. The X-ray powder diffraction pattern (X-RPD), Fourier transform infrared (FT-IR), differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) techniques are used to characterize amorphous form and crystalline polymorphic forms.

VARENICLINE STANDARDS AND IMPURITY CONTROLS

The subject invention provides a varenicline composition that comprises varenicline, or a pharmaceutically acceptable salt thereof, and an amount of a compound selected from one or more of several mononitro, monoamine mixed aminonitro, diamino or dinitro intermediates, and the concentration of said compound is greater than O ppm and not greater than about 500 ppm, not greater than about 100 ppm or not greater than about 10 ppm. Methods for synthesizing and using such varenicline compositions are also provided.

PREPARATION OF SUBSTITUTED QUINOXALINES FROM THE DIANLINE WITH 2,3-DIHYDROXY-1,4-DIOXANE

The present invention relates to a new process for the preparation of substituted quinoxalines (I) by cyclization of the corresponding dianiline with 2,3 dihydroxy-1,4-dioxane. In a preferred embodiment, the invention provides a process for the preparation of compounds having the formula III wherein Q is a nitrogen protecting group. Compounds of formula III and their derivatives are precursors to certain aryl fused azapolycyclic compounds which exhibit activity as agents for the treatment of neurological and psychological disorders.