143924-45-2

Basic information

• Product Name: 2-(1 Lamda{2}-piperidin-4-yl)pyridin-4-yl dihydrochloride
• Synonyms: 2-(1 Lamda{2}-piperidin-4-yl)pyridin-4-yl dihydrochloride;2-(Piperidin-4-yl)pyridine dihydrochloride
• CAS NO: 143924-45-2
• Molecular Formula: C₁₀H₁₄N₂*2ClH
• Molecular Weight: 235.15344
• Mol File: 143924-45-2.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 2-(1 Lamda{2}-piperidin-4-yl)pyridin-4-yl dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1 Lamda{2}-piperidin-4-yl)pyridin-4-yl dihydrochloride(143924-45-2)
• EPA Substance Registry System: 2-(1 Lamda{2}-piperidin-4-yl)pyridin-4-yl dihydrochloride(143924-45-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 143924-45-2(Hazardous Substances Data)

Usage

General Description

2-(1 Lamda{2}-Piperidin-4-yl)pyridin-4-yl dihydrochloride, also known as PNU-282987, is a chemical compound that acts as a selective agonist for the alpha7 nicotinic acetylcholine receptor. It is used in scientific research to study the role of alpha7 nicotinic acetylcholine receptors in various physiological and pathological processes, including learning and memory, neuroprotection, and neuroinflammation. The compound has been found to have potential therapeutic applications in treating conditions such as Alzheimer's disease, schizophrenia, and inflammatory bowel disease. Its unique pharmacological profile and selectivity make it a valuable tool for understanding the mechanisms of action and potential therapeutic benefits of targeting the alpha7 nicotinic acetylcholine receptor.

Upstream product

• 90606-77-2 3',6'-dihydro-2'H-[2,4']bipyridinyl-1'-carboxylic acid tert-butyl ester 
• 138647-49-1 4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 206446-49-3 3',4',5',6'-tetrahydro-2'H-[2,4'-bipyridine]-1'-carboxylic acid tert-butyl ester 
• 581-47-5 4-(2-pyridyl)pyridine 

Downstream Products

• 30532-37-7 4-(2-pyridinyl)piperidine 

Relevant articles and documents

CYCLIC AMINOMETHYL PYRIMIDINE DERIVATIVE

The present invention provides a cyclic aminomethyl pyrimidine derivative and a pharmaceutically acceptable salt thereof with high selectivity for dopamine D4 receptors, which are useful for treating a disease such as attention deficit hyperactivity disorder. Specifically, a compound of formula (1) or a pharmaceutically acceptable salt thereof is provided, wherein n and m are independently 1 or 2; Ra is C1-6 alkyl group, C3-6 cycloalkyl group, or amino group; Rb is hydrogen atom, C1-6 alkyl group or the like, provided that when Ra is amino group, then Rb is hydrogen atom; Rc1 and Rc2 are independently hydrogen atom, or C1-6 alkyl group; Rd1 and Rd2 are independently hydrogen atom, fluorine atom or the like; ring Q is an optionally-substituted pyridyl group or an optionally-substituted isoquinolyl group; and the bond having a dashed line is a single or double bond.

Discovery of 3-methyl-N-(1-oxy-3′,4′,5′,6′- tetrahydro-2′H-[2,4′-bipyridine]-1′-ylmethyl)benzamide (ABT-670), an orally bioavailable dopamine D4 agonist for the treatment of erectile dysfunction

The goal of this study was to identify a structurally distinct D4-selective agonist with superior oral bioavailability to our first-generation clinical candidate 1a (ABT-724) for the potential treatment of erectile dysfunction. Arylpiperazines such as (heteroarylmethyl)piperazine 1a, benzamide 2, and acetamides such as 3a,b exhibit poor oral bioavailability. Structure-activity relationship (SAR) studies with the arylpiperidine template provided potent partial agonists such as 4d and 5k that demonstrated no improvement in oral bioavailability. Further optimization with the (N-oxy-2-pyridinyl)piperidine template led to the discovery of compound 6b (ABT-670), which exhibited excellent oral bioavailability in rat, dog, and monkey (68%, 85%, and 91%, respectively) with comparable efficacy, safety, and tolerability to 1a. The N-oxy-2-pyridinyl moiety not only provided the structural motif required for agonist function but also reduced metabolism rates. The SAR study leading to the discovery of 6b is described herein.

Preparation of Piperidinylpyridines via Selective Reduction of Bipyridines with Nickel-Aluminum Alloy

Bipyridines were reduced to piperidinylpyridines in modest yield using nickel-aluminum alloy in potassium hydroxide solution.The reduction was selective, and 3-substituted rings were reduced in preference to 4-substitution.Thus 2,3-bipyridine gave only 2-(3'-piperidinyl)pyridine, 2,4-bipyridine gave only 2-(4'-piperidinyl)pyridine, and 3,4-bipyridine gave only 4-(3'-piperidinyl)pyridine.The symmetrical 2,2'- and 4,4'-bipyridines also gave the corresponding piperidinylpyridines, but the reduction of 3,3'-bipyridine was too sluggish to be practical.The products were identified using 13C NMR spectroscopy, and the 13C NMR spectra of the starting bipyridines were also recorded.