77837-09-3

Basic information

• Product Name: METHYL 5-CARBOXY-N-PHENYL-2-1H-PYRIDONE
• Synonyms: 1,6-Dihydro-6-oxo-1-phenyl-nicotinic Acid Methyl Ester;Methyl 6-Oxo-1-phenyl-1,6-dihydropyridine-3-carboxylate;6-Oxo-1-phenyl-1,6-dihydro-pyridine-3-carboxylic acid methyl ester
• CAS NO: 77837-09-3
• Molecular Formula: C₁₃H₁₁NO₃
• Molecular Weight: 229.23
• Product Categories: Aromatics Compounds;Aromatics;Metabolites;Metabolites & Impurities
• Mol File: 77837-09-3.mol

Chemical Properties

• Melting Point: 160-162 °C
• Boiling Point: 370.016°C at 760 mmHg
• Flash Point: 177.58°C
• Appearance: /
• Density: 1.271g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.596
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -1.40±0.63(Predicted)
• CAS DataBase Reference: METHYL 5-CARBOXY-N-PHENYL-2-1H-PYRIDONE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 5-CARBOXY-N-PHENYL-2-1H-PYRIDONE(77837-09-3)
• EPA Substance Registry System: METHYL 5-CARBOXY-N-PHENYL-2-1H-PYRIDONE(77837-09-3)

Safety Data

• Hazardous Substances Data: 77837-09-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 5-CARBOXY-N-PHENYL-2-1H-PYRIDONE is used as an active pharmaceutical ingredient (API) for the development of new drugs targeting kidney disease in patients with diabetes. Its role as a metabolite of Pirfenidone contributes to its potential therapeutic effects in managing and treating this specific health condition.
Used in Research and Development:
In the field of medical research, METHYL 5-CARBOXY-N-PHENYL-2-1H-PYRIDONE serves as a valuable compound for studying the effects and mechanisms of Pirfenidone in treating kidney disease associated with diabetes. This research can lead to the development of more effective treatments and a better understanding of the underlying causes of the disease.
Used in Drug Formulation:
METHYL 5-CARBOXY-N-PHENYL-2-1H-PYRIDONE can be used as a key component in the formulation of new drugs or drug combinations for the treatment of kidney disease in diabetic patients. Its chemical properties and metabolite status make it a promising candidate for improving the efficacy and safety of existing treatments.
Used in Quality Control and Standardization:
In the pharmaceutical industry, METHYL 5-CARBOXY-N-PHENYL-2-1H-PYRIDONE can be employed as a reference compound for quality control and standardization purposes. Its unique chemical properties and association with Pirfenidone make it an ideal candidate for ensuring the consistency, purity, and potency of drugs targeting kidney disease in diabetic patients.

InChI:InChI=1/C13H11NO3/c1-17-13(16)10-7-8-12(15)14(9-10)11-5-3-2-4-6-11/h2-9H,1H3

Upstream product

• 66171-50-4 6-oxo-1,6-dihydropyridin-3-carboxylic acid methyl ester 
• 98-80-6 phenylboronic acid 
• 6018-41-3 methyl coumalate 
• 62-53-3 aniline 
• 500-05-0 2H-pyran-2-one-5-carboxylic acid 

Downstream Products

• 77837-08-2 6-oxo-1-phenyl-1,6-dihydro-3-pyridinecarboxylic acid 
• 1392219-90-7 N-(1-azabicyclo[2.2.2]octan-3-yl)-6-oxo-1-phenyl-3-pyridinecarboxamide 
• 1392221-19-0 6-oxo-1-phenyl-1,6-dihydro-pyridine-3-carbonyl chloride 
• 1392221-04-3 (1-azabicyclo[2.2.2]octan-3-yl)-6-oxo-1-phenyl-3-pyridinecarboxylate 
• 1093952-03-4 5-(hydroxy(methyl-d2))-1-phenylpyridin-2(1H)-one 

Relevant articles and documents

Substituent Effects of 2-Pyridones on Selective O-Arylation with Diaryliodonium Salts: Synthesis of 2-Aryloxypyridines under Transition-Metal-Free Conditions

An efficient transition-metal-free strategy to synthesize 2-aryloxypyridine derivatives has been developed by a selective O-arylation of 2-pyridones with diaryliodonium salts. The reaction was compatible with a series of functional groups for 2-pyridones and diaryliodonium salts such as halides, nitro, cyano, and ester groups. The substituents at the C6-position of 2-pyridones favored O-arylation products because of steric hindrance. The reaction was easily performed on a gram-scale and 6-chloro-2-pyridone was a good precursor to access various unsubstituted 2-aryloxypyridines by dehalogenation. A P2Y 1 lead compound analogue could be prepared in good yield over two steps.

Synthesis, pharmacophores, and mechanism study of pyridin-2(1H)-one derivatives as regulators of translation initiation factor 3A

Twenty-seven 1,5-disubstituted-pyridin-2(1H)-one derivatives were synthesized and evaluated for their anti-cancer and anti-fibrosis activity by A549 and NIH3T3 cell viability assays, respectively. To study the selectivity between the cancer and fibrosis cell lines, pharmacophore models (F 1-F4) were built in advance for compounds with pyridin-2(1H)-one scaffold, which revealed the relationship between the occupation of the aromatic sub-site F4 and potent anti-cancer activity. The relationship between structure and anti-cancer activity for all target compounds is also reported herein: 1-Phenyl-5-((m-tolylamino)methyl) pyridine-2(1H)-one (22) displayed both potency and selectivity (IC50 = 0.13 mM) toward the A549 cell line through the inhibition of translation initiation, especially by eIF3a suppression, and can be treated as a lead for the design of novel eIF3a regulators and anti-lung cancer agents. A series of pyridin-2(1H)-one derivatives were synthesized. Elucidation of their pharmacophores and mechanism of action suggested that structures with F 4 occupation displayed more selective anti-cancer than anti-fibrosis activity and that they interrupt the initiation phase of translation by acting on the eukaryotic translation initiation factor 3, subunit A.

Discovery of dap-3 polymyxin analogues for the treatment of multidrug-resistant gram-negative nosocomial infections

We report novel polymyxin analogues with improved antibacterial in vitro potency against polymyxin resistant recent clinical isolates of Acinetobacter baumannii and Pseudomonas aeruginosa. In addition, a human renal cell in vitro assay (hRPTEC) was used to inform structure-toxicity relationships and further differentiate analogues. Replacement of the Dab-3 residue with a Dap-3 in combination with a relatively polar 6-oxo-1-phenyl-1,6-dihydropyridine-3- carbonyl side chain as a fatty acyl replacement yielded analogue 5x, which demonstrated an improved in vitro antimicrobial and renal cytotoxicity profiles relative to polymyxin B (PMB). However, in vivo PK/PD comparison of 5x and PMB in a murine neutropenic thigh model against P. aeruginosa strains with matched MICs showed that 5x was inferior to PMB in vivo, suggesting a lack of improved therapeutic index in spite of apparent in vitro advantages.

PHARMACEUTICAL COMPOSITION COMPRISING PYRIDONE DERIVATIVES

A pyridone derivative compound and a pharmaceutically acceptable salt, isomer, solvate or hydrate thereof, and a preventive or therapeutic pharmaceutical composition for cognitive disorders that includes the pyridone derivative compound or a pharmaceutically acceptable salt, isomer, solvate or hydrate thereof.

PHARMACEUTICAL COMPOSITION COMPRISING PYRIDONE DERIVATIVES

A pyridone derivative compound and a pharmaceutically acceptable salt, isomer, solvate or hydrate thereof, and a preventive or therapeutic pharmaceutical composition for cognitive disorders that includes the pyridone derivative compound or a pharmaceutically acceptable salt, isomer, solvate or hydrate thereof.

SUBSTITUTED N-ARYL PYRIDINONES

Disclosed herein are methods of administering deuterated pirfenidone and kits thereof.

DEUTERATED PYRIDINONES

This invention relates to novel substituted pyridinones, their deuterium-modified derivatives and pharmaceutically acceptable salts thereof. This invention also provides compositions comprising a compound of this invention and the use of such compositions in methods of treating diseases and conditions that are beneficially treated by administering a TNF (tumor necrosis factor) alpha production inhibitor/TGF (transforming growth factor) beta inhibitor.

SUBSTITUTED N-ARYL PYRIDINONES

Disclosed herein are substituted N-Aryl pyridinone fibrotic inhibitors and/or collagen infiltration modulators of Formula I, process of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.