573675-27-1

Basic information

• Product Name: 3-AMINO-5-BROMO-PYRIDINE-2-CARBONITRILE
• Synonyms: 3-AMINO-5-BROMO-PYRIDINE-2-CARBONITRILE;3-Amino-5-bromopicolinonitrile
• CAS NO: 573675-27-1
• Molecular Formula: C₆H₄BrN₃
• Molecular Weight: 198.02006
• Mol File: 573675-27-1.mol

Chemical Properties

• Boiling Point: 376.5±42.0 °C(Predicted)
• Appearance: /
• Density: 1.80±0.1 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: -1.28±0.10(Predicted)
• CAS DataBase Reference: 3-AMINO-5-BROMO-PYRIDINE-2-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINO-5-BROMO-PYRIDINE-2-CARBONITRILE(573675-27-1)
• EPA Substance Registry System: 3-AMINO-5-BROMO-PYRIDINE-2-CARBONITRILE(573675-27-1)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 573675-27-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-AMINO-5-BROMO-PYRIDINE-2-CARBONITRILE is used as a building block for the synthesis of various nitrogen-containing heterocycles and biologically active compounds. Its presence of different functional groups allows for a wide range of chemical reactions, making it a valuable component in the creation of complex organic molecules.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 3-AMINO-5-BROMO-PYRIDINE-2-CARBONITRILE is utilized for the development of pharmaceuticals. Its unique structure contributes to the design of new drugs with potential therapeutic properties, particularly in the synthesis of compounds targeting specific biological pathways or receptors.
Used in Agrochemical Development:
3-AMINO-5-BROMO-PYRIDINE-2-CARBONITRILE is also used in the development of agrochemicals, where it serves as an intermediate for the synthesis of compounds with pesticidal or herbicidal properties. Its versatility in chemical reactions allows for the creation of effective agents for agricultural applications.
Used as an Intermediate in Industrial Applications:
Due to its properties, 3-AMINO-5-BROMO-PYRIDINE-2-CARBONITRILE is an important intermediate in the production of numerous valuable compounds for various industrial applications. Its role in these processes is crucial for the synthesis of end products that find use in a wide array of sectors, including but not limited to pharmaceuticals, agrochemicals, and other specialty chemical industries.

Upstream product

• 90902-84-4 2,5-dibromopyridin-3-ylamine 
• 573675-25-9 5-bromo-3-nitropyridine-2-carbonitrile 
• 15862-34-7 5-bromo-3-nitro-2-pyridone 
• 6945-68-2 5-bromo-3-nitro-pyridin-2-ylamine 
• 15862-37-0 2,5-dibromo-3-nitro-pyridine 

Downstream Products

• 2241325-66-4 4-(3-(trans-2,6-dimethylmorpholino)isothiazolo[4,3-b]pyridin-6-yl)-2-methoxyaniline 
• 2241325-66-4 6-(4-amino-3-methoxyphenyl)-3-(cis-2,6-dimethylmorpholino)isothiazolo[4,3-b]pyridine 

Relevant articles and documents

Selective inhibitors of cyclin G associated kinase (GAK) as anti-hepatitis C agents

Cyclin G associated kinase (GAK) emerged as a promising drug target for the treatment of viral infections. However, no potent and selective GAK inhibitors have been reported in the literature to date. This paper describes the discovery of isothiazolo[5,4-

Design, synthesis, and evaluation of potent RIPK1 inhibitors with in vivo anti-inflammatory activity

RIPK1 plays a key role in the necroptosis pathway that regulates inflammatory signaling and cell death in various diseases, including inflammatory and neurodegenerative diseases. Herein, we report a series of potent RIPK1 inhibitors, represented by compound 70. Compound 70 efficiently blocks necroptosis induced by TNFα in both human and mouse cells (EC50 = 17–30 nM). Biophysical assay demonstrates that compound 70 potently binds to RIPK1 (Kd = 9.2 nM), but not RIPK3 (Kd > 10,000 nM). Importantly, compound 70 exhibits greatly improved metabolic stability in human and rat liver microsomes compared to compound 6 (PK68), a RIPK1 inhibitor reported in our previous work. In addition, compound 70 displays high permeability in Caco-2 cells and excellent in vitro safety profiles in hERG and CYP assays. Moreover, pre-treatment of 70 significantly ameliorates hypothermia and lethal shock in SIRS mice model. Lastly, compound 70 possesses favorable pharmacokinetic parameters with moderate clearance and good oral bioavailability in SD rat. Taken together, our work supports 70 as a potent RIPK1 inhibitor and highlights its potential as a prototypical lead for further development in necroptosis-associated inflammatory disorders.

A Scaffold-Hopping Strategy toward the Identification of Inhibitors of Cyclin G Associated Kinase

We recently reported the discovery of isothiazolo[4,3-b]pyridine-based inhibitors of cyclin G associated kinase (GAK) displaying low nanomolar binding affinity for GAK and demonstrating broad-spectrum antiviral activity. To come up with novel core structures that act as GAK inhibitors, a scaffold-hopping approach was applied starting from two different isothiazolo[4,3-b]pyridines. In total, 13 novel 5,6- and 6,6-fused bicyclic heteroaromatic scaffolds were synthesized. Four of them displayed GAK affinity with Kd values in the low micromolar range that can serve as chemical starting points for the discovery of GAK inhibitors based on a different scaffold.

Optimization of Isothiazolo[4,3- b]pyridine-Based Inhibitors of Cyclin G Associated Kinase (GAK) with Broad-Spectrum Antiviral Activity

There is an urgent need for strategies to combat dengue and other emerging viral infections. We reported that cyclin G-associated kinase (GAK), a cellular regulator of the clathrin-associated host adaptor proteins AP-1 and AP-2, regulates intracellular trafficking of multiple unrelated RNA viruses during early and late stages of the viral lifecycle. We also reported the discovery of potent, selective GAK inhibitors based on an isothiazolo[4,3-b]pyridine scaffold, albeit with moderate antiviral activity. Here, we describe our efforts leading to the discovery of novel isothiazolo[4,3-b]pyridines that maintain high GAK affinity and selectivity. These compounds demonstrate improved in vitro activity against dengue virus, including in human primary dendritic cells, and efficacy against the unrelated Ebola and chikungunya viruses. Moreover, inhibition of GAK activity was validated as an important mechanism of antiviral action of these compounds. These findings demonstrate the potential utility of a GAK-targeted broad-spectrum approach for combating currently untreatable emerging viral infections.

IMINOTHIADIAZINE DIOXIDES BEARING AN AMINE-LINKED SUBSTITUENT AS BACE INHIBITORS, COMPOSITIONS, AND THEIR USE

In its many embodiments, the present invention provides certain iminothiazine dioxide compounds, including compounds Formula (I): or a tautomers thereof, and pharmaceutically acceptable salts of said compounds and said tautomers, wherein R1, R2, ring A, RA, m, ringB, RB, and n are as defined herein. The novel compounds of the invention are useful as BACE inhibitors and/or for the treatment and prevention of various pathologies related thereto. Pharmaceutical compositions comprising one or more such compounds (alone and in combination with one or more other active agents), and methods for their preparation and use, including for the possible treatment of Alzheimer's disease, are also disclosed.

GAK MODULATORS AS ANTIVIRALS

The present invention relates to the use of a class of novel isothiazolo[4,3-b]pyridine derivatives as well as to pharmaceutical compositions comprising one or more of said isothiazolo[4,3- b]pyridine derivatives and one or more pharmaceutically acceptable excipients as biologically active ingredients, more specifically as medicaments for the treatment of disorders and pathologic conditions such as viral diseases.

NOVEL GAK MODULATORS

The present invention relates to a class of novel isothiazolo[4,3-b]pyridine derivatives and a method for their preparation, as well as to pharmaceutical compositions comprising one or more of said isothiazolo[4,3-b]pyridine derivatives and one or more pharmaceutically acceptable excipients. The present invention further relates to the use of said novel isothiazolo[4,3-b]pyridine derivatives as biologically active ingredients, more specifically as medicaments for the treatment of disorders and pathologic conditions such as, but not limited to, cell-proliferative and neurodegenerative diseases.

ANDROGEN RECEPTOR MODULATING COMPOUNDS

Compounds of formula (I) wherein R1 to R16, A. B and E are as defined in the claims and pharmaceutically acceptable salts and esters thereof, are disclosed. The compounds of formula (I) possess utility as tissue-selective androgen receptor modulators (SARM) and are particularly useful as medicaments in the treatment of prostate cancer and other AR dependent conditions and diseases where AR antagonism is desired.

CAPSAICIN RECEPTOR AGONISTS

Capsaicin receptor agonists are provided. Such compounds are ligands that may be used to modulate VRl activity in vivo or in vitro, and are particularly useful in the treatment of conditions responsive to capsaicin receptor activation in humans, domesticated companion animals and livestock animals. Pharmaceutical compositions and methods for using them to treat such disorders are provided, as are methods for using such ligands for receptor localization studies.