118290-26-9

Usage

Uses

Used in Pharmaceutical Industry:
AF-DX 384 is used as a therapeutic agent for the treatment of cognitive impairments and memory deficits. Its application is based on its ability to selectively target M2 and M4 muscarinic acetylcholine receptors, leading to increased acetylcholine release in the hippocampus and cortex, which are key areas for learning and memory.
Used in Research Applications:
AF-DX 384 is utilized as a research tool for studying the role of M2 and M4 muscarinic acetylcholine receptors in cognitive functions and the potential development of treatments for conditions such as Alzheimer's disease and other age-related cognitive decline disorders. Its selectivity for M2 and M4 receptors over M1, M3, and M5 makes it a valuable compound for investigating receptor-specific functions and interactions.
Used in Drug Development:
AF-DX 384 serves as a lead compound in the development of new drugs targeting muscarinic acetylcholine receptors. Its antagonistic properties and selectivity for M2 and M4 receptors make it a promising candidate for the creation of novel medications aimed at improving cognitive function and treating memory-related disorders.

Upstream product

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• 267220-63-3 (S)-(-)-(N,N-dipropyl)piperidine-2-carboxamide 
• 267220-64-4 (S)-(+)-2-(N,N-dipropylaminomethyl)piperidine 
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• 267220-52-0 (R)-(-)-2-(N,N-dipropylaminomethyl)piperidine 
• 198058-50-3 (R)-(+)-N,N-dipropyl [(N'-methoxycarbonyl)piperidine]-2-carboxamide 
• 3433-37-2 piperidin-2-ylmethanol 
• 63587-45-1 Toluene-4-sulfonic acid 1-(toluene-4-sulfonyl)-piperidin-2-ylmethyl ester 
• 186790-30-7 Dipropyl-[1-(toluene-4-sulfonyl)-piperidin-2-ylmethyl]-amine 
• 186790-33-0 Toluene-4-sulfonic acid 1-cyanomethyl-piperidin-2-ylmethyl ester 
• 4377-33-7 2-chloromethylpyridine 
• 267220-59-7 (+/-)-[(N'-cyanomethyl)piperidine]-2-(N,N-dipropyl)carboxamide 

Relevant academic research and scientific papers

Syntheses of R and S isomers of AF-DX 384, a selective antagonist of muscarinic M2 receptors

Enantiomers of 5,11-dihydro-11-[2-[2-[(N,N-dipropylaminomethyl)piperidin-1-yl]ethylamino]-carbonyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one (AF-DX 384) 1, have been synthesized from (S)-(+) and (R)-(-)-2-[N,N-dipropylaminomethyl]piperidine 4. The enantiomeric excess of 1 has been determined by capillary electrophoresis by using the α-highly sulphated cyclodextrin (α-HSCD) as chiral selector within the running electrolyte. (S)-(+)-(4) was prepared from (S)-(-)-pipecolic acid in a 4-step procedure (overall yield: 30%, ee: 99%) and (R)-(-)-AF-DX 384 from (R)-(+)-pipecolic acid. The (R)-(-) isomer exhibited in vitro a 23-fold higher affinity than its enantiomer (S)-(+) towards muscarinic receptors of subtype 2. Copyright (C) 2000.

Syntheses of piperidine and perhydroazepine derivatives, precursors of two selective antagonists of muscarinic M2 receptors: AF-DX 384 and its perhydroazepine isomer

Several routes to the synthesis of the polyamines 2a and 2b required for the preparation of the muscarinic antagonists AF-DX 384 1a and its perhydroazepine isomer 1b respectively have been developed and compared. Piperidine 2a has been obtained in 4 steps in 13-15% overall yield from 2-(chloromethyl)-pyridine 3. The perhydroazepine 2b has been prepared in 4 steps in 49% overall yield from 3-aminolactam 7. Transformations of piperidinemethanol 11 afford exclusively compound 2a (5 steps, 17-20% overall yield), via the N-tosylpiperidine 12, but lead to a 1:1 mixture of isomers 2a and 2b (4 steps, 15-20% overall yield for compounds 2a and 2b) via the N-(cyanomethyl)piperidine 15. Limitations to the ring enlargement of piperidine derivatives as a function of the heterocyclic nitrogen substituent are defined.

Condensed diazepinones, processes for preparing them and pharmaceutical compositions containing these compounds

There are described new condensed diazepinones of general formula STR1 wherein B represents one of the divalent groups STR2 and D represents the groups STR3 and X1, X2 represents a =CH-- group or, if B assumes the meaning of the divalent group S, U or W, they may also represent an N atom, A1 and A2 in general represent lower alkylene groups, Z represents a C--C bond or the groups, --O--, --S--, --CH2 --, or --(CH2)2 --; R represents hydrogen or methyl, R1 and R2 generally represent alkyl groups which, together with the nitrogen atom between them, may also form a saturated monocylic, heterocyclic group, R3 represents alkyl, chlorine or hydrogen, R4 represents hydrogen or methyl, R5 and R6 represent hydrogen, halogen or alkyl, R7 represents hydrogen, chlorine or methyl, R8 represents hydrogen or lower alkyl, R9 represents hydrogen, halogen, lower alkyl and R10 represents hydrogen or methyl and R12 represents branched or unbranched alkyl. The compounds of general formula I and the acid addition salts thereof may be resolved into their isomers. The compounds of formula I and their salts may be used as vagal pacemakers for the treatment of bradycardia and bradyarrhythmia.