1257704-57-6

Basic information

• Product Name: CEP 33779
• Synonyms: [8-(4-Methylsulfonylphenyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl][3-(4-methylpiperazin-1-yl)phenyl]amine;N-[3-(4-Methyl-1-piperazinyl)phenyl]-8-[4-(methylsulfonyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-amine;[1,2,4]Triazolo[1,5-a]pyridin-2-amine, N-[3-(4-methyl-1-piperazinyl)phenyl]-8-[4-(methylsulfonyl)phenyl]-;N-(3-(4-Methylpiperazin-1-yl)phenyl)-8-(4-(methylsulfonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridi;N-[3-(4-methylpiperazin-1-yl)phenyl]-8-(4-methylsulfonylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine
• CAS NO: 1257704-57-6
• Molecular Formula: C₂₄H₂₆N₆O₂S
• Molecular Weight: 462.56724
• Product Categories: Inhibitor;JAK/STAT;Inhibitors;JAK;STAT
• Mol File: 1257704-57-6.mol

Chemical Properties

• Appearance: /
• Density: 1.35
• Solubility: ≥23.15 mg/mL in DMSO with gentle warming; insoluble in EtOH
• PKA: 7.78±0.42(Predicted)
• CAS DataBase Reference: CEP 33779(CAS DataBase Reference)
• NIST Chemistry Reference: CEP 33779(1257704-57-6)
• EPA Substance Registry System: CEP 33779(1257704-57-6)

Safety Data

• Hazardous Substances Data: 1257704-57-6(Hazardous Substances Data)

Usage

Uses

Used in Anti-inflammatory Applications:
CEP 33779 is used as an anti-inflammatory agent for reducing the production of inflammatory cytokines. It has been shown to decrease splenomegaly and lymphomegaly in mouse models of systemic lupus erythematosus, thereby extending survival and improving clinical scores.
Used in Anti-arthritic Applications:
In the field of rheumatology, CEP 33779 is used as an anti-arthritic agent. It has demonstrated the ability to diminish inflammatory signaling and improve clinical scores in mice during collagen antibody-induced arthritis and collagen type II-induced arthritis.
Used in Anticancer Applications:
CEP 33779 is used as an anticancer agent, particularly in the treatment of colorectal cancer. It has been shown to induce regression of established colorectal tumors in mice by reducing angiogenesis and the proliferation of tumor cells.
Used in Pharmaceutical Industry:
CEP 33779 is used as a potent inhibitor of JAK2 for the development of therapeutic agents targeting inflammatory and immune-related disorders. Its selectivity and oral availability make it a valuable compound for the creation of new drugs to treat a variety of conditions, including autoimmune diseases and cancers.

Upstream product

• 747413-17-8 1-bromo-3-(4-methylpiperazin-1-yl)benzene 
• 1257704-13-4 8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5,a]-pyridine-2-ylamine 
• 13534-99-1 2-Amino-3-bromopyridine 
• 1124382-72-4 8-bromo-[1,2,4]triazolo[1,5-a]pyridine-2-ylamine 
• 31197-30-5 1-(3-bromophenyl)piperazine 
• 1124383-00-1 N-(3-bromo-2-pyridinyl)-N’-carboethoxy-thiourea 
• 109-01-3 1-methyl-piperazine 
• 108-36-1 1,3-dibromobenzene 
• 1257706-00-5 2-chloro-8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine 
• 148546-99-0 3-(4-methylpiperazin-1-yl)aniline 
• 149104-88-1 4-methanesulphonylphenylboronic acid 

Relevant articles and documents

An Improved Synthesis of the Free Base and Diglycolate Salt of CEP-33779; A Janus Kinase 2 Inhibitor

CEP-33779 is a triazole that has been reported to show highly selective inhibition of Janus kinase 2 (JAK2). An efficient process to form CEP-33779 will be presented that uses multiple palladium couplings to provide the drug substance in a convergent mann

JANUS KINASE 2 (JAK2) INHIBITOR FOR THE TREATMENT OF LUPUS

The present invention provides a method for treating lupus in a subject, comprising the step of administering to the subject COMPOUND A.

A selective, orally bioavailable 1,2,4-triazolo[1,5-a]pyridine-based inhibitor of janus kinase 2 for use in anticancer therapy: Discovery of CEP-33779

Members of the JAK family of nonreceptor tyrosine kinases play a critical role in the growth and progression of many cancers and in inflammatory diseases. JAK2 has emerged as a leading therapeutic target for oncology, providing a rationale for the development of a selective JAK2 inhibitor. A program to optimize selective JAK2 inhibitors to combat cancer while reducing the risk of immune suppression associated with JAK3 inhibition was undertaken. The structure-activity relationships and biological evaluation of a novel series of compounds based on a 1,2,4-triazolo[1,5-a]pyridine scaffold are reported. Para substitution on the aryl at the C8 position of the core was optimum for JAK2 potency (17). Substitution at the C2 nitrogen position was required for cell potency (21). Interestingly, meta substitution of C2-NH-aryl moiety provided exceptional selectivity for JAK2 over JAK3 (23). These efforts led to the discovery of CEP-33779 (29), a novel, selective, and orally bioavailable inhibitor of JAK2.

PREPARATION AND USES OF 1,2,4-TRIAZOLO [1,5a] PYRIDINE DERIVATIVES

This application relates to compounds of the general Formula I and salts thereof, wherein X, R1A, R1B, R2, R3, R4, and R5 are as defined herein. The application also relates to compositions and methods of treatment of hyperproliferative diseases or disorders.