1096-03-3

Usage

Uses

Used in Pharmaceutical Industry:
4-anilino-1-benzylpiperidine-4-carboxamide is used as a modulator of muscarinic receptors for the treatment of central nervous system (CNS) disorders. Its interaction with muscarinic receptors can help in managing various conditions related to the CNS, such as Alzheimer's disease, schizophrenia, and other cognitive impairments.
The compound's ability to modulate muscarinic receptors is attributed to its structural features, which allow it to selectively bind and influence the receptor's activity. This selective modulation can lead to improved therapeutic outcomes and reduced side effects compared to non-selective treatments.

InChI:InChI=1/C19H23N3O/c20-18(23)19(21-17-9-5-2-6-10-17)11-13-22(14-12-19)15-16-7-3-1-4-8-16/h1-10,21H,11-15H2,(H2,20,23)

Upstream product

• 3612-20-2 1-phenylmethyl-4-piperidone 
• 62-53-3 aniline 
• 968-86-5 1-benzyl-4-(phenylamino)piperidine-4-carbonitrile 

Downstream Products

• 61085-60-7 methyl 4-(phenylamino)-1-(phenylmethyl)-4-piperidinecarboxylate 
• 85098-64-2 1-benzyl-4-(phenylamino)piperidine-4-carboxylic acid 
• 130819-96-4 4-(anilinomethyl)-1-benzyl-4-chloropiperidine 
• 130819-95-3 1'-benzyl-3-phenylspiro<4,5-dihydro-3H-1,2,3-oxathiazol-4,4'-piperidine> 
• 974-42-5 1-(phenylmethyl)-4,4-(2-phenyl-2,4-diaza-4-oxo-cyclopentane)piperidine 
• 974-41-4 8-benzyl-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one 
• 1021-25-6 1-Phenyl-1,3,8-triaza-spiro[4.5]decan-4-one 
• 72996-78-2 methyl 4-[N-(1-oxopropyl)-N-phenylamino]-4-piperidinecarboxylate 
• 61085-72-1 methyl 4-[N-(1-oxopropyl)-N-phenylamino]-1-benzyl-4-piperidinecarboxylate 
• 61087-51-2 1-benzyl-4-anilinoisonipecotic acid dihydrochloride 
• 256507-84-3 1-benzyl-4-[phenyl(propionyl)amino]piperidine-4-carboxylic acid 
• 690272-33-4 1-benzyl-4-[(3-methylbutanoyl)(phenyl)amino]piperidine-4-carboxylate ethyl ester oxalate 

Relevant academic research and scientific papers

Syntheses, biological evaluation, and molecular modeling of 18F-labeled 4-anilidopiperidines as μ-opioid receptor imaging agents

The synthesis, evaluation, and molecular modeling of a series of 18F-labeled 4-anilidopiperidines with high affinities for the μ-opioid receptor (μ-OR) are reported. On the basis of the high brain uptake and selective retention in brain regions that contain a high concentration of the μ-OR, combined with a good metabolic stability, [ 18F]fluoro-pentyl carfentanil ([18F]4) and 2-(±)[18F]-fluoropropyl-sufentanil ([18F]6) were selected as the lead compounds for further evaluation. The binding affinity to the human μ-OR was 0.74 and 0.13 nM for [18F]4 and [ 18F]6, respectively. In vitro autoradiography of [18F] 4 and [18F] 6 on rat brain sections produced patterns in accordance with the known distribution of μ-OR expression. Structure-activity relationships of the fluorinated compounds are discussed with respect to the interaction with an activated-state model of the μ-OR. Taken together, the in vivo and in vitro data indicate that [18F] 4 and [18F] 6 hold promise for studying the μ-opioid receptor in humans by means of positron emission tomography.

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.

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.

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 Hindered α-Amino Carbonyls: Copper-Catalyzed Radical Addition with Nitroso Compounds

The synthesis of sterically hindered anilines has been a significant challenge in organic chemistry. Here we report a Cu-catalyzed radical addition with in situ-generated nitroso compounds to prepare sterically hindered amines directly from readily available materials. The transformation is conducted at room temperature, uses abundant copper salts, and is tolerant of a range of functional groups.

Synthesis of 4-anilinopiperidine methyl esters, intermediates in the production of carfentanil, sufentanil, and remifentanil

Two spirodiaza intermediates have been made and employed in the synthesis of 4-anilinopiperidine methyl esters. These intermediates can be utilized in the production of commercial synthetic analgesics carfentanil, sufentanil, and remifentanil.

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.