449808-50-8

Basic information

• Product Name: 6-(2,4-Difluorophenoxy)-8-Methyl-2-(Methylsulfonyl)pyrido[2,3-d]pyriMidin-7(8H)-one
• Synonyms: 6-(2,4-Difluorophenoxy)-8-Methyl-2-(Methylsulfonyl)pyrido[2,3-d]pyriMidin-7(8H)-one
• CAS NO: 449808-50-8
• Molecular Formula: C₁₅H₁₁F₂N₃O₄S
• Molecular Weight: 367.3273464
• Mol File: 449808-50-8.mol

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly, Sonicated)
• CAS DataBase Reference: 6-(2,4-Difluorophenoxy)-8-Methyl-2-(Methylsulfonyl)pyrido[2,3-d]pyriMidin-7(8H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(2,4-Difluorophenoxy)-8-Methyl-2-(Methylsulfonyl)pyrido[2,3-d]pyriMidin-7(8H)-one(449808-50-8)
• EPA Substance Registry System: 6-(2,4-Difluorophenoxy)-8-Methyl-2-(Methylsulfonyl)pyrido[2,3-d]pyriMidin-7(8H)-one(449808-50-8)

Safety Data

• Hazardous Substances Data: 449808-50-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
6-(2,4-difluorophenoxy)-8-methyl-2-(methylsulfonyl)pyrido[2,3-d]pyrimidin-7(8H)-one is used as an intermediate in the synthesis of Pamapimod (P167500) for its role as a selective inhibitor of the α-isoform of p38 MAP kinase. This makes it a valuable compound in the development of treatments for conditions where the inhibition of this kinase can provide therapeutic benefits.
Used in Research and Development:
In the field of medicinal chemistry and drug discovery, 6-(2,4-difluorophenoxy)-8-methyl-2-(methylsulfonyl)pyrido[2,3-d]pyrimidin-7(8H)-one is used as a research compound to explore its potential in creating new drugs with improved efficacy and selectivity. Its structural properties allow scientists to investigate its interactions with various biological targets, potentially leading to the discovery of novel therapeutic agents.
Used in the Treatment of Inflammatory Diseases:
Given that Pamapimod, the compound synthesized using 6-(2,4-difluorophenoxy)-8-methyl-2-(methylsulfonyl)pyrido[2,3-d]pyrimidin-7(8H)-one as an intermediate, is a p38 MAP kinase inhibitor, it is likely to be used in the treatment of inflammatory diseases. p38 MAP kinase is involved in the regulation of inflammatory responses, and its inhibition can help manage conditions such as rheumatoid arthritis, psoriasis, and inflammatory bowel disease.
Used in Oncology:
As p38 MAP kinase plays a role in cellular processes like apoptosis, cell proliferation, and differentiation, compounds like Pamapimod that inhibit this kinase may also have applications in oncology. 6-(2,4-difluorophenoxy)-8-methyl-2-(methylsulfonyl)pyrido[2,3-d]pyrimidin-7(8H)-one, by virtue of its role in synthesizing Pamapimod, could contribute to the development of cancer treatments, particularly for tumors where p38 MAP kinase activity is a factor in tumor growth or resistance to chemotherapy.

Upstream product

• 449811-63-6 methyl 2,4-difluorophenoxyacetate 
• 2223-96-3 4-chloro-2-ethylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester 
• 717-30-6 2-(2,4-difluorophenoxy)acetic acid ethyl ester 
• 367-27-1 2,4-difluorophenol 
• 76360-82-2 4-methylamino-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester 
• 5909-24-0 4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester 
• 17759-30-7 (4-methylamino-2-methylsulfanyl-pyrimidin-5-yl)-methanol 
• 449811-12-5 6?(2,4?difluorophenoxy)?8?methyl?2?(methylthio)pyrido[2,3?d]pyrimidin?7(8H)?one 

Downstream Products

• 449811-92-1 [14C]-R1487 
• 449811-23-8 6-(2,4-difluorophenoxy)-8-methyl-2-(tetrahydrothiopyran-4-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one 
• 1280218-19-0 6-(2,4-difluorophenoxy)-2-((R)-2-methanesulfonyl-1-methylethylamino)-8-methyl-8Hpyrido[2,3-d]pyrimidin-7-one 
• 1222660-39-0 6-(2,4-difluorophenoxy)-2-((S)-2-methanesulfonyl-1-methylethylamino)-8-methyl-8Hpyrido[2,3-d]pyrimidin-7-one 
• 1280218-56-5 6-(2,4-difluorophenoxy)-8-methyl-2-(piperidin-4-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one 
• 1280218-20-3 2-(1-acetylpiperidin-4-ylamino)-6-(2,4-difluorophenoxy)-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one 
• 757935-92-5 2-[(1-oxidotetrahydro-2H-thiopyran-4-yl)amino]-6-(2,4-difluorophenoxy)-8-methylpyrido[2,3-d]pyrimidin-7(8H)-one 
• 740078-01-7 2-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)amino]-6-(2,4-difluorophenoxy)-8-methylpyrido[2,3-d]pyrimidin-7(8H)-one 
• 1280218-54-3 6-(2,4-difluorophenoxy)-8-methyl-2-((R)-1-methyl-2-methylsulfanylethylamino)-8H-pyrido[2,3-d]pyrimidin-7-one 
• 1222665-27-1 6-(2,4-difluorophenoxy)-8-methyl-2-((S)-1-methyl-2-tetrazol-2-yl-ethylamino)-8Hpyrido[2,3-d]pyrimidin-7-one 
• 1222648-80-7 6-(2,4-difluorophenoxy)-8-methyl-2-((R)-1-methyl-2-tetrazol-2-yl-ethylamino)-8Hpyrido[2,3-d]pyrimidin-7-one 
• 449811-01-2 [14C]-Pamapimod 
• 1280218-55-4 2-(1-benzylpiperidin-4-ylamino)-6-(2,4-difluorophenoxy)-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one 
• 1280218-18-9 2-(2'-methylsulfonylethylamino)-6-(2,4-difluorophenoxy)-8-methylpyrido[2,3-d]pyrimidin-7(8H)-one 

Relevant articles and documents

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Activation of various interacting stress kinases, particularly the c-Jun N-terminal kinases (JNK), and a concomitant phosphorylation of insulin receptor substrate 1 (IRS-1) at serine 307 play a central role both in insulin resistance and in β-cell dysfunction. IRS-1 phosphorylation is stimulated by elevated free fatty acid levels through different pathways in obesity. A series of novel pyrido[2,3-d]pyrimidin-7-one derivatives were synthesized as potential antidiabetic agents, preventing IRS-1 phosphorylation at serine 307 in a cellular model of lipotoxicity and type 2 diabetes.

Discovery of 6-(2,4-difluorophenoxy)-2-[3-hydroxy-1-(2-hydroxyethyl) propylamino]-8-methyl-8 H -pyrido[2,3- d ]pyrimidin-7-one (pamapimod) and 6-(2,4-difluorophenoxy)-8-methyl-2-(tetrahydro-2 H -pyran-4-ylamino)pyrido[2,3- d ]pyrimidin-7(8 H)-one (R1487) as orally bioavailable and highly selective inhibitors of p38α mitogen-activated protein kinase

The development of a new series of p38α inhibitors resulted in the identification of two clinical candidates, one of which was advanced into a phase 2 clinical study for rheumatoid arthritis. The original lead, an lck inhibitor that also potently inhibited p38α, was a screening hit from our kinase inhibitor library. This manuscript describes the optimization of the lead to p38-selective examples with good pharmacokinetic properties.

6-Substituted pyrido-pyrimidines

The present invention provides compounds of the Formula I and II: wherein R1, R3, W, Z, X1, X2, Ar1, R8 and R9 are as defined herein, and methods and intermediates for their preparation and uses thereof.