273748-51-9

Usage

Uses

Used in Pharmaceutical Synthesis:
2-(pyridin-3-ylmethyl)quinuclidin-3-one is used as a precursor in the synthesis of pharmaceutical compounds, particularly for the development of anticholinergic agents. Its structural properties make it a valuable component in creating medications that can block the action of acetylcholine, a neurotransmitter.
Used in Medicinal Chemistry and Drug Discovery:
In the field of medicinal chemistry, 2-(pyridin-3-ylmethyl)quinuclidin-3-one is utilized as a building block for the production of other organic compounds. Its versatility in chemical reactions contributes to the discovery and development of new drugs with potential therapeutic applications.
Used in Neuroprotective Research:
2-(pyridin-3-ylmethyl)quinuclidin-3-one is studied for its potential use as a cholinergic agent, which could have implications for the treatment of neurological disorders. Its neuroprotective properties are of interest to researchers looking for compounds that can protect and preserve nerve cells from damage or degeneration.
Used in Chemical Compound Production:
As a building block in the production of other organic compounds, 2-(pyridin-3-ylmethyl)quinuclidin-3-one is used across various chemical industries to create a range of products, from pharmaceuticals to specialty chemicals, leveraging its reactivity and structural attributes.

Upstream product

• 500-22-1 3-pyridinecarboxaldehyde 
• 1193-65-3 3-quinuclidinone hydrochloride 
• 3731-38-2 3-Quinuclidinone 
• 1111942-12-1 2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]octan-3-one hydrochloride 
• 273748-55-3 2-(pyridin-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one 
• 1193-65-3 quinuclidin-3-one hydrochloride 
• 273748-55-3 (±)-2-(pyridin-3-ylmethylidene)-1-azabicyclo[2.2.2]octan-3-one 

Downstream Products

• 1403993-34-9 3-(4-(3-methoxyphenyl)-1H-1,2,3-triazol-1-yl)-2-(pyridin-3-ylmethyl)quinuclidine 
• 1391013-37-8 cis-3-amino-2-(pyridin-3-ylmethyl)-1-azabicyclo[2.2.2]octane 
• 1391013-37-8 trans-3-amino-2-(pyridin-3-ylmethyl)-1-azabicyclo[2.2.2]octane 
• 639487-71-1 C₂₁H₂₅N₃O₂ 
• 1408251-39-7 C₂₀H₂₃N₃O₂ 
• 1408251-40-0 C₂₁H₂₅N₃O₂ 
• 1408251-41-1 C₂₀H₂₂FN₃O₂ 
• 1408251-42-2 C₂₀H₂₁Cl₂N₃O 
• 639486-97-8 C₂₀H₂₁Cl₂N₃O 
• 1408251-43-3 C₂₁H₂₃F₂N₃O₂ 
• 1111942-09-6 C₂₁H₂₇N₃ 
• 1111942-10-9 (2S,3R)-3-amino-2-(pyridin-3-ylmethyl)-1-azabicyclo[2.2.2]-octane di-p-toluoyl-D-tartrate 
• 1111942-11-0 (2S,3R)-N-[2-(pyridin-3-ylmethyl)-1-azabicyclo[2.2.2]oct-3-yl]benzo[b]furan-2-carboxamide p-toluenesulfonate 
• 1111942-08-5 (2S)-2-(pyridin-3-ylmethyl)-1-azabicyclo-[2.2.2]octan-3-one Di-p-toluoyl-D-tartrate 

Relevant academic research and scientific papers

Functional characterization of multifunctional ligands targeting acetylcholinesterase and alpha 7 nicotinic acetylcholine receptor

Alzheimer's disease (AD) is a neurodegenerative disorder associated with cholinergic dysfunction, provoking memory loss and cognitive dysfunction in elderly patients. The cholinergic hypothesis provided over the years with molecular targets for developing palliative treatments for AD, acting on the cholinergic system, namely, acetylcholinesterase and α7 nicotinic acetylcholine receptor (α7 nAChR). In our synthetic work, we used “click-chemistry” to synthesize two Multi Target Directed Ligands (MTDLs) MB105 and MB118 carrying tacrine and quinuclidine scaffolds which are known for their anticholinesterase and α7 nAChR agonist activities, respectively. Both, MB105 and MB118, inhibit human acetylcholinesterase and human butyrylcholinesterase in the nanomolar range. Electrophysiological recordings on Xenopus laevis oocytes expressing human α7 nAChR showed that MB105 and MB118 acted as partial agonists of the referred nicotinic receptor, albeit, with different potencies despite their similar structure. The different substitution at C-3 on the 2,3-disubstituted quinuclidine scaffold may account for the significantly lower potency of MB118 compared to MB105. Electrophysiological recordings also showed that the tacrine precursor MB320 behaved as a competitive antagonist of human α7 nAChR, in the micromolar range, while the quinuclidine synthetic precursor MB099 acted as a partial agonist. Taken all together, MB105 behaved as a partial agonist of α7 nAChR at concentrations where it completely inhibited human acetylcholinesterase activity paving the way for the design of novel MTDLs for palliative treatment of AD.

1,4-DISUBSTITUTED 1,2,3-TRIAZOLES, METHODS FOR PREPARING SAME, AND DIAGNOSTIC AND THERAPEUTIC USES THEREOF

A compound having the following general formula (I): wherein: X is a nitrogen atom and Y is a carbon atom; orX is a carbon atom and Y is a nitrogen atom;the Ar group is an aryl or heteroaryl group; andthe RN and RN′ groups, together with the carbon atoms

ANTIPRURITIC AGENT

An antipruritic which exerts an antipruritic effect based on a novel action mechanism and is effective for pruritus. The antipruritic contains as an effective ingredient a compound which activates a central type nicotinic acetylcholine receptor.

Discovery of (2S,3R)-N-[2-(pyridin-3-ylmethyl)-1-azabicyclo[2.2.2]oct-3-yl] benzo[b]furan-2-carboxamide (TC-5619), a selective α7 nicotinic acetylcholine receptor agonist, for the treatment of cognitive disorders

(2S,3R)-N-[2-(Pyridin-3-ylmethyl)-1-azabicyclo[2.2.2]oct-3-yl]benzo[b] furan-2-carboxamide (7a, TC-5619), a novel selective agonist of the α7 neuronal nicotinic acetylcholine receptor, has been identified as a promising drug candidate for the treatment of cognitive impairment associated with neurological disorders. 7a demonstrated more than a thousand-fold separation between the affinities for the α7 and α4β2 receptor subtypes and had no detectable effects on muscle or ganglionic nicotinic receptor subtypes, indicating a marked selectivity for the central nervous system over the peripheral nervous system. Results obtained from homology modeling and docking explain the observed selectivity. 7a had positive effects across cognitive, positive, and negative symptoms of schizophrenia in animal models and was additive or synergistic with the antipsychotic clozapine. Compound 7a, as an augmentation therapy to the standard treatment with antipsychotics, demonstrated encouraging results on measures of negative symptoms and cognitive dysfunction in schizophrenia and was well tolerated in a phase II clinical proof of concept trial in patients with schizophrenia.

Surface plasmon resonance biosensor based fragment screening using acetylcholine binding protein identifies ligand efficiency hot spots (le hot spots) by deconstruction of nicotinic acetylcholine receptor α7 ligands

The soluble acetylcholine binding protein (AChBP) is a homologue of the ligand-binding domain of the nicotinic acetylcholine receptors (nAChR). To guide future fragment-screening using surface plasmon resonance (SPR) biosensor technology as a label-free, direct binding, biophysical screening assay, a focused fragment library was generated based on deconstruction of a set of α7 nAChR selective quinuclidine containing ligands with nanomolar affinities. The interaction characteristics of the fragments and the parent compounds with AChBP were evaluated using an SPR biosensor assay. The data obtained from this direct binding assay correlated well with data from the reference radioligand displacement assay. Ligand efficiencies for different (structural) groups of fragments in the library were correlated to binding with distinct regions of the binding pocket, thereby identifying ligand efficiency hot spots (LE hot spots). These hot spots can be used to identity the most promising hit fragments in a large scale fragment library screen.

Evaluation of structurally diverse neuronal nicotinic receptor ligands for selectivity at the α6* subtype

Direct comparison of pyridine versus pyrimidine substituents on a small but diverse set of ligands indicates that the pyrimidine substitution has the potential to enhance affinity and/or functional activity at α6 subunit-containing neuronal nicotinic rece

2S,3R)-N-(2-((3-PYRIDINYL)METHYL)-1-AZABICYCLO[2.2.2]OCT-3-YL-BENZYOFURAN-2-CARBOXAMIDE, NOVEL SALT FORMS, AND METHODS OF USE THEREOF

The present invention relates to (2S,3R)—N-(2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)benzofuran-2-carboxamide, novel salt forms thereof, methods for its preparation, novel intermediates, and methods for treating a wide variety of conditions and

HETEROARYL-SUBSTiTUTED DIAZATRICYCLOALKANES, METHODS FOR ITS PREPARATION AND USE THEREOF

The present invention relates to amide and urea derivatives of heteroaryl- substituted diazatricycloalkanes, of the Formula (I) with the definition as set out in the description pharmaceutical compositions including the compounds, methods of preparing the

2-(Arylmethyl)-3-substituted quinuclidines as selective α7 nicotinic receptor ligands

A series of 2-(arylmethyl)-3-substituted quinuclidines was developed as α7 neuronal nicotinic acetylcholine receptor (nAChR) agonists based on a putative pharmacophore model. The series is highly selective for the α7 over other nAChRs (e.g., the α4β2 of the CNS, and the muscle and ganglionic subtypes) and is functionally tunable at α7. One member of the series, (+)-N-(1-azabicyclo[2.2.2]oct-3-yl)benzo[b]furan-2-carboxamide (+)-8l), has potent agonistic activity for the α7 nAChR (EC50 = 33 nM, Imax = 1.0), at concentrations below those that result in desensitization.

3-substituted-2(arylalkyl)-1-azabicycloalkanes and methods of use thereof

The present invention relates to 3-substituted-2-(arylalkyl)-1-azabicycloalkanes, methods of preparing the compounds and methods of treatment using the compounds. The azabicycloalkanes generally are azabicycloheptanes, azabicyclooctanes, or azabicyclononanes. The aryl group in the arylalkyl moiety is a 5- or 6-membered ring heteroaromatic, preferably 3-pyridinyl and 5-pyrimidinyl moieties, and the alkyl group is typically a C1-4 alkyl. The substituent at the 3-position of the 1-azabicycloalkane is a carbonyl group-containing moiety, such as an amide, carbamate, urea, thioamide, thiocarbamate, thiourea or similar functionality. The compounds exhibit activity at nicotinic acetylcholine receptors (nAChRs), particularly the α7 nAChR subtype, and are useful towards modulating neurotransmission and the release of ligands involved in neurotransmission. Methods for preventing or treating conditions and disorders, including central nervous system (CNS) disorders, which are characterized by an alteration in normal neurotransmission, are also disclosed. Also disclosed are methods for treating inflammation, autoimmune disorders, pain and excess neovascularization, such as that associated with tumor growth.