953-79-7

Usage

Uses

Used in Pharmaceutical Research:
1-Benzyl-4-(methylamino)piperidine-4-carbonitrile is used as a chemical intermediate in the synthesis of potential drugs for the treatment of various medical conditions. Its unique structure allows for the development of new therapeutic agents with novel mechanisms of action.
Used in Medicinal Chemistry:
As a piperidine derivative, 1-Benzyl-4-(methylamino)piperidine-4-carbonitrile is utilized in medicinal chemistry for the design and optimization of drug candidates. Its structural features can be modified to enhance pharmacokinetic and pharmacodynamic properties, leading to improved drug efficacy and safety.
Used in Neuroscience Research:
1-Benzyl-4-(methylamino)piperidine-4-carbonitrile is employed as a research tool in neuroscience to study its potential effects on the central nervous system. 1-Benzyl-4-(methylamino)piperidine-4-carbonitrile may provide insights into the development of new treatments for neurological disorders and help understand the underlying mechanisms of action.
Used in Psychopharmacology:
Due to its potential psychoactive properties, 1-Benzyl-4-(methylamino)piperidine-4-carbonitrile is used in psychopharmacological research to explore its effects on cognitive and emotional processes. This may contribute to the development of new therapies for mental health conditions and enhance our understanding of the neurochemical basis of behavior and mood regulation.

InChI:InChI=1/C14H19N3/c1-16-14(12-15)7-9-17(10-8-14)11-13-5-3-2-4-6-13/h2-6,16H,7-11H2,1H3

Upstream product

• 3612-20-2 1-phenylmethyl-4-piperidone 
• 143-33-9 sodium cyanide 
• 74-89-5 methylamine 
• 593-51-1 methylamine hydrochloride 
• 151-50-8 potassium cyanide 

Downstream Products

• 235101-00-5 1-benzyl-4-cyano-4-(methyl)methanesulfonylamidopiperidine 
• 685545-02-2 1-(1-benzyl-4-cyanopiperidin-4-yl)-3-(4-cyanophenyl)-1-methylurea 
• 685545-06-6 4-(1-methyl-2,4-dioxo-1,3,8-triazaspiro[4.5]dec-3-yl)benzonitrile 
• 685545-05-5 4-(8-benzyl-1-methyl-2-oxo-1,3,8-triazaspiro[4.5]dec-3-yl)benzonitrile 
• 685545-04-4 4-(8-benzyl-1-methyl-2,4-dioxo-1,3,8-triazaspiro[4.5]dec-3-yl)benzonitrile 
• 685544-99-4 4-(8-benzyl-4-hydroxy-1-methyl-2-oxo-1,3,8-triazaspiro[4.5]dec-3-yl)benzonitrile 
• 685544-52-9 3-{[3-(4-cyanophenyl)-1-methyl-2,4-dioxo-1,3,8-triazaspiro[4.5]decane-8-carbonyl]amino}-3-phenylpropionic acid ethyl ester 
• 685545-49-7 3-{[3-(4-carbamimidoylphenyl)-1-methyl-2,4-dioxo-1,3,8-triazaspiro[4.5]decane-8-carbonyl]amino}-3-phenylpropionic acid ethyl ester 

Relevant academic research and scientific papers

Discovery of Novel 2,8-Diazaspiro[4.5]decanes as Orally Active Glycoprotein IIb-IIIa Antagonists

In our efforts to develop orally active GPIIb-IIIa antagonists with improved pharmaceutical properties, we have utilized a novel 2,8-diazaspiro[4.5]decane scaffold as a template. We describe here our investigation of a variety of templates including spiropiperidinyl-γ -lactams, spiropiperidinylimide, spiropiperidinylureas, and spiropiperidinylhydantoins. With the appropriate acidic and basic pharmacophores in place, each template yielded analogues with potent GPIIb-IIIa inhibitory activity. One of the compounds, 59 (CT50787), was also used to demonstrate for the first time the use of a pharmacological agent which is αIIbβ3 specific to display biological activity in a lower species such as mouse and to extend bleeding times. Evaluation of the pharmacokinetic properties of selected compounds from each series in rat, dog, and cynomolgus monkey has led to the identification of 22 (CT51464), a double prodrug, with excellent pharmacokinetic properties. It exhibited good pharmacokinetic profile across species (F% = 33 (Cyno), 73 (dog), 22 (rat); t1/2β = 14. 2 h (Cyno), 8.97 h (dog), 1.81 h (rat)). The biologically active form, 23 (CT50728), displayed inhibition of platelet aggregation in platelet rich plasma (PRP) with an IC50 value of 53 nM in citrate buffer, 110 nM in PPACK anticoagulated PRP, and 4 nM in solid-phase GPIIb-IIIa competition binding assay (ELISA). Both 23 and 22 were stable in human liver microsomes, did not inhibit the P450 3A4 isozyme, and had low protein binding (18.22% for 23) and a desirable log P (0.45 ± 0.06 for 22, and -0.91 ± 0.32 for 23). It is predicted that the high oral bioavailability for these compounds in multiple species should translate into lower intra- and intersubject variability in man. The long plasma half-life of the lead is consistent with once or twice daily administration for chronic therapy. Analogue 22 (CT51464) thus appears to be a promising oral GPIIb-IIIa inhibitor with significantly improved pharmacokinetic properties over the previously described clinical candidates and may be found useful in the treatment of arterial occlusive disorders.

The CSIC [carbanion mediated sulfonate (sulfonamido) intramolecular cyclization] reaction: Scope and limitations

The CSIC (Carbanion-mediated Sulfonate-Sulfonamide-Intramolecular Cyclization) reaction has been extended to new carbonyl containing substrates, showing the scope and limitations of this process. Suitable derivatives of ketones (e.g acetophenone (1)), β-keto esters (e.g ethyl acetoacetate (4)), γ-keto esters (e.g ethyl 2-oxocyclohexaneacetate (5) and ethyl levulinate (6)) proved reluctant to undergo this protocol. Cyclopropyl methyl ketone (2) gave the heterocycle (3), only in the 'sulfonamide' synthetic sequence of the CSIC reaction. Cyclic azaketones (e.g tropinone (7)) fated also, but 4-piperidones (9, 10) afforded the novel 3,8- disubstituted 4-amino-8-aza-1-oxa-2-thiaspiro[4.5]dec-3-ene 2,2-dioxide (12, 15a-c) and 8-substituted 4-amino-1,8-diaza-2-thiaspiro[4.5]dec-3-ene 2,2- dioxide (18a, 18b, 21a, 21b) ring systems; the former compounds are the first examples of such ring systems substituted at the 3-position, whereas the latter represent the first ever representatives of spiro fused systems containing the 4-amino-2,3-dihydroisothiazole 1,1-dioxide moiety. Base promoted (NaH or DBU) cyclization of precursors 11b, 14a-c, 17b, 17c and 20 give the final adducts in good overall yield. Finally, we were unsuccessful with some conveniently functionalized anthranilonitrile derivatives (8a-d), in an attempt to extend the CSIC reaction to β-aminonitriles. As a result of these studies the substrate dependent reactivity in the CSIC reaction has been analyzed in depth and some restrictions and limitations have been observed and discussed.