61085-41-4

Basic information

• Product Name: 1-benzyl-4-[(4-fluorophenyl)amino]piperidine-4-carboxamide
• Synonyms: 1-benzyl-4-[(4-fluorophenyl)amino]piperidine-4-carboxamide;4-[(4-Fluorophenyl)amino]-1-(phenylmethyl)-4-piperidinecarboxamide
• CAS NO: 61085-41-4
• Molecular Formula: C₁₉H₂₂FN₃O
• Molecular Weight: 327.3958832
• EINECS: 262-586-6
• Mol File: 61085-41-4.mol

Chemical Properties

• Melting Point: 162.5 °C
• Boiling Point: 522°C at 760 mmHg
• Flash Point: 269.5°C
• Appearance: /
• Density: 1.25g/cm³
• Vapor Pressure: 5.42E-11mmHg at 25°C
• Refractive Index: 1.628
• PKA: 15.76±0.20(Predicted)
• CAS DataBase Reference: 1-benzyl-4-[(4-fluorophenyl)amino]piperidine-4-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 1-benzyl-4-[(4-fluorophenyl)amino]piperidine-4-carboxamide(61085-41-4)
• EPA Substance Registry System: 1-benzyl-4-[(4-fluorophenyl)amino]piperidine-4-carboxamide(61085-41-4)

Safety Data

• Hazardous Substances Data: 61085-41-4(Hazardous Substances Data)

Usage

Chemical structure

Piperidine derivative with a benzyl group attached to the nitrogen atom and a fluorophenylamino group attached to the piperidine ring

Pharmaceutical properties

May act as a receptor antagonist or agonist in the central nervous system

Research chemical

Applications in neuroscience and drug development

Further studies needed

To fully understand its pharmacological and toxicological properties

InChI:InChI=1/C19H22FN3O/c20-16-6-8-17(9-7-16)22-19(18(21)24)10-12-23(13-11-19)14-15-4-2-1-3-5-15/h1-9,22H,10-14H2,(H2,21,24)

Upstream product

• 61085-37-8 1-benzyl-4-((4-fluorophenyl)amino)piperidine-4-carbonitrile 
• 371-40-4 4-fluoroaniline 
• 3612-20-2 1-phenylmethyl-4-piperidone 

Downstream Products

• 167263-29-8 8-benzyl-1-(4-fluoro-phenyl)-1,3,8-triaza-spiro[4.5]dec-2-en-4-one 
• 58012-16-1 1-(4-fluoro-phenyl)-1,3,8-triaza-spiro[4.5]decan-4-one 
• 85098-78-8 8-benzyl-1-(4-fluoro-phenyl)-1,3,8-triaza-spiro[4.5]decan-4-one 

Relevant articles and documents

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.

TRIAZA-SPIRODECANONES AS DDR1 INHIBITORS

The present invention relates to compounds of formula (I) or pharmaceutically acceptable salts thereof, wherein L and R1 to R5 are as described herein, as well as processes for their manufacture, pharmaceutical compositions comprising them, and their use as medicaments.

TRPA1 MODULATORS

This disclosure relates to polycyclic heteroaromatic compounds useful as TRPA1 modulators, as well as compositions and methods of treating pain that include the compounds.

Design, synthesis, and biological evaluation of halogenated N-(2-(4-Oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-8-yl)ethyl)benzamides: Discovery of an isoform-selective small molecule phospholipase D2 inhibitor

Phospholipase D (PLD) catalyzes the conversion of phosphatidylcholine to the lipid second messenger phosphatidic acid. Two mammalian isoforms of PLD have been identified, PLD1 and PLD2, which share 53% sequence identity and are subject to different regulatory mechanisms. Inhibition of PLD enzymatic activity leads to increased cancer cell apoptosis, decreased cancer cell invasion, and decreased metastasis of cancer cells; therefore, the development of isoform-specific, PLD inhibitors is a novel approach for the treatment of cancer. Previously, we developed potent dual PLD1/PLD2, PLD1-specific (>1700-fold selective), and moderately PLD2-preferring (>10-fold preferring) inhibitors. Here, we describe a matrix library strategy that afforded the most potent (PLD2 IC50 = 20 nM) and selective (75-fold selective versus PLD1) PLD2 inhibitor to date, N-(2-(1-(3-fluorophenyl)-4-oxo-1, 3,8-triazaspiro[4.5]decan-8-yl)ethyl)-2-naphthamide (22a), with an acceptable DMPK profile. Thus, these new isoform-selective PLD inhibitors will enable researchers to dissect the signaling roles and therapeutic potential of individual PLD isoforms to an unprecedented degree.

TRIAZA-SPIROPIPERIDINE DERIVATIVES FOR USE AS GLYT-1 INHIBITORS IN THE TREATMENT OF NEUROLOGICAL AND NEUROPSYCHIATRIC DISORDERS

The invention relates to compounds of the general formula (I), wherein A-A is -CH2-CH2-, -CH2-CH2-CH2-, -CH2-0- or -0-CH2-; x is hydrogen or hydroxy; R1 is aryl or heteroaryl, unsubstituted or substituted by one or more substituents, selected from the group consisting of lower alkyl, lower alkoxy, halogen or trifluoromethyl; R2 is aryl or heteroaryl, unsubstituted or substituted by one or more substituents, selected from the group consisting of lower alkyl, lower alkoxy, halogen or trifluoromethyl, or is lower alkyl, -(CH2)n--cycloalkyl, -(CH2)n-CF3, -(CH2)p-0-lower alkyl, -(CH2)1,2-phenyl, optionally substituted by halogen, lower alkyl, lower alkoxy or trifluoromethyl, or is -(CH2)p-NRR", wherein W and R" form together with the N-atom a heterocyclic ring, selected from the group consisting of piperidine, morpholine, thiomorpholine or 1, I-dioxo thiomorpholine; R3, R4 are independently from each other hydrogen, lower alkyl, phenyl or benzyl; R5 is hydrogen, lower alkyl or benzyl; R6 is hydrogen or lower alkyl; n is 0, 1 or 2; and p is 2 or 3; and to pharmaceutically acceptable acid addition salts thereof for the treatment of psychoses, pain, neurodegenerative disfunction in memory and learning, schizophrenia, dementia and other diseases in which cognitive processes are impaired, such as attention deficit disorders or Alzheimer's disease.

SUBSTITUTED PYRROLIDIN-3-YL-ALKYL-PIPERIDINES

The present invention relates to substituted pyrrolidinyl-3-yl-alkyl-piperidines, their stereoisomers, and pharmaceutically acceptable salts thereof and processes for preparation of the same. The compounds of the present invention are useful in their pharmacological activities such as tachykinin antagonism, especially substance P and neurokinin A antagonism, and the like. Compounds having the property of tachykinin antagonism are indicated for conditions associated with neurogenic inflammation and other diseases described herein.