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Usage

Uses

Used in Pharmaceutical Industry:
1-Benzyl-4-cyano-4-(phenylamino)piperidine is used as modulators of muscarinic receptors for the treatment of central nervous system (CNS) disorders. Its ability to interact with muscarinic receptors allows it to modulate the cholinergic system, which plays a crucial role in cognitive functions and other neurological processes. This makes it a promising candidate for the development of drugs targeting a range of CNS disorders, including Alzheimer's disease, schizophrenia, and other cognitive impairments.

InChI:InChI=1/C19H21N3/c20-16-19(21-18-9-5-2-6-10-18)11-13-22(14-12-19)15-17-7-3-1-4-8-17/h1-10,21H,11-15H2

Upstream product

• 3612-20-2 1-phenylmethyl-4-piperidone 
• 7677-24-9 trimethylsilyl cyanide 
• 62-53-3 aniline 
• 151-50-8 potassium cyanide 
• 127354-23-8 C₂₀H₂₁ClN₄O₃S 
• 143-33-9 sodium cyanide 
• 240486-11-7 4-(2-bromophenylamino)-1-(phenylmethyl)-4-piperidinecarbonitrile 
• 615-36-1 2-bromoaniline 

Downstream Products

• 120517-22-8 (1-Benzyl-4-thiazol-2-yl-piperidin-4-yl)-phenyl-amine 
• 122823-29-4 4-(2-furoyl)-4-anilinopiperidine 
• 122823-30-7 4-(2-thienyl)-4-anilinopiperidine 
• 120517-25-1 [1-Benzyl-4-(4,5-dimethyl-thiazol-2-yl)-piperidin-4-yl]-phenyl-amine 
• 120517-29-5 (1'-Benzyl-2',3',5',6'-tetrahydro-1'H-[2,4']bipyridinyl-4'-yl)-phenyl-amine 
• 63260-82-2 ethyl 1-benzyl-4-phenylamino-4-piperidinecarboxylate 
• 127354-23-8 C₂₀H₂₁ClN₄O₃S 
• 130819-94-2 1-benzyl-4-(propionanilido)piperidine-4-carbonitrile 
• 120115-93-7 1-benzyl-4-(4-methylthiazol-2-yl)-4-anilinopiperidine 
• 1096-03-3 1-benzyl-4-phenylaminopiperidine-4-carboxylic acid amide 
• 61085-60-7 methyl 4-(phenylamino)-1-(phenylmethyl)-4-piperidinecarboxylate 
• 61085-72-1 methyl 4-[N-(1-oxopropyl)-N-phenylamino]-1-benzyl-4-piperidinecarboxylate 
• 72996-78-2 methyl 4-[N-(1-oxopropyl)-N-phenylamino]-4-piperidinecarboxylate 
• 85098-64-2 1-benzyl-4-(phenylamino)piperidine-4-carboxylic acid 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of 2-arylaminopyrimidine derivatives bearing 1,3,8-triazaspiro[4,5]decan-4-one or piperidine-3-carboxamide moiety as novel Type-I1/2 ALK inhibitors

Aiming to develop novel Type-I1/2 inhibitors of ALK to overcome extensive resistance mutations, especially the L1196M mutation surrounding the ATP pocket, two series of 2-arylaminopyrimidine derivatives (11a-f and 22a-t) were designed based on scaffold hopping. The extensive structural elaboration discovered compound 22o which possessed excellent IC50 values of 0.06 and 0.23 μM against ALK-positive Karpas299 and H2228 cell lines, respectively. Meanwhile, 22o displayed encouraging inhibitory potency in the ALKWT (2.5 nM) and ALKL1196M (6.5 nM) enzymatic assays. Furthermore, the AO/EB and Hoechst 33258 assays illustrated 22o could induce cell apoptosis in a dose-dependent manner. Eventually, the molecular docking of 22o with ALK clearly presented the vital interactions within the active site, which was in accordance with Type-I1/2 inhibitor binding mode.

1,3,8-TRIAZASPIRO COMPOUNDS AND THEIR USE AS MEDICAMENTS FOR THE TREATMENT OF REPERFUSION INJURY

The present invention relates to a 1,3,8-triazaspiro compound of Formula (I), wherein A is -CH2, -SO2 -, -NH-CO-, -NH-CS- or -CO-; the dashed line represents a single or double bond; R1 is a substituent selected from (C1-C3) alkyl, phenyl, thienyl and cyclohexyl, said substituent being optionally substituted by halogen or (C1 -C3) alkyl; and R2 is a substituent selected from H, (C1-C3) alkyl, (C1-C3) alkoxy, -CF3 and halogen; and wherein, when the dashed line is a double bond, A is -CH2 - and R1 is phenyl, or a pharmaceutically acceptable salt thereof for use in the treatment of reperfusion injury diseases. The 1,3,8-triazaspiro compound of the invention is a selective inhibitor of the C subunit of the F1/Fo-ATP synthase complex and a modulator of the mitochondrial permeability transition pore activity in mammalian cells and tissues, in the treatment of reperfusion injury diseases.

OPIOID HAPTENS, CONJUGATES, VACCINES, AND METHODS OF GENERATING ANTIBODIES

The disclosure provides, inter alia, opioid haptens, opioid hapten conjugates, opioid vaccines, methods of treating or preventing opioid use disorder, methods of treating opioid overdose, and methods of generating and/or isolating antibodies selective for opioids.

Discovery of Novel 1,3,8-Triazaspiro[4.5]decane Derivatives That Target the c Subunit of F1/FO-Adenosine Triphosphate (ATP) Synthase for the Treatment of Reperfusion Damage in Myocardial Infarction

Recent cardiology research studies have reported the role, function, and structure of the mitochondrial permeability transition pore (mPTP) and have shown that its opening plays a key role in the progression of myocardial cell death secondary to reperfusion. In this manuscript, we validated a new pharmacological approach as an adjunct to reperfusion in myocardial infarction (MI) treatment and describe the discovery, optimization, and structure-activity relationship (SAR) studies of the first small-molecule mPTP opening inhibitors based on a 1,3,8-triazaspiro[4.5]decane scaffold that targets the c subunit of the F1/FO-ATP synthase complex. We identified three potential compounds with good mPTP inhibitory activity and beneficial effects in a model of MI, including a decreased apoptotic rate in the whole heart and overall improvement of cardiac function upon administration during reperfusion. The selected compounds did not show off-target effects at the cellular and mitochondrial levels. Moreover, the compounds preserved the mitochondrial ATP content despite interacting with the ATP synthase complex.

Synthesis of intermediate anilino methyl esters used in the production of synthetic opioid analgesics

An improved process or method of synthesis of carfentanil and other potent opioid analgesics of the N-alkyl 4-substituted 4-piperidinylamide class which can be used as morphine substitutes.

SUBSTITUTED 4-AMINO-PIPERIDINES

The present invention relates to new substituted 4-amino-piperidine opioid receptor modulators, pharmaceutical compositions thereof, and methods of use thereof

A facile method for preparation of [2H3]-sufentanil and its metabolites

An improved process for the synthesis of sufentanil with an overall yield of 26% is described. The reactive and high yielding N-debenzylation of the piperidine intermediate 7 using a mixture of Pd/C and Pd(OH)2 was applied to other drug intermediates affording free amines in short reaction times. The deuterium-labeled sufentanil and the metabolite desmethylsufentanil were synthesized applying the optimized process.

Aromatic amines as nucleophiles in the Bargellini reaction

Aromatic amines can be employed in the Bargellini reaction to generate useful intermediates. Rapid, practical access to functionalised, privileged structures may have significant utility in the synthesis of drug-like molecules. An improved synthesis of carfentanil analogues illustrates this point.

Piperidone derivatives and medical uses thereof

The present invention relates to compositions comprising 4-Oxo-piperidine-carboxylates and derivatives thereof, for example derivatives substituted with phenyl, nitrophenyl or benzyl groups. It also teaches the medical use of these and related compounds for treatment of retroviral diseases, in particular, HIV and HTLV, proliferative diseases, in particular CML and Trypanosomiasis.