1187449-01-9

Usage

Uses

Used in Organic Synthesis:
2-amino-4-bromo-5-chloropyridine is used as a key intermediate in the synthesis of various organic compounds. Its unique structure with bromine and chlorine substitutions on the pyridine ring allows for versatile chemical reactions, making it a valuable building block in the creation of complex molecules.
Used in Pharmaceutical Industry:
2-amino-4-bromo-5-chloropyridine is used as a starting material for the development of new pharmaceutical compounds. Its reactivity and structural features enable the synthesis of potential drug candidates with desired therapeutic properties.
Used in Chemical Research:
2-amino-4-bromo-5-chloropyridine is used as a research tool in academic and industrial laboratories. It serves as a model compound for studying the effects of bromine and chlorine substitutions on the reactivity and properties of pyridine derivatives, contributing to the understanding of fundamental chemical principles and the development of new synthetic strategies.

Upstream product

• 84249-14-9 2-amino-4-bromopyridine 

Downstream Products

• 1610033-94-7 2-((2R,4R)-1-(4-(((3,4-trans)-1-(5-chloro-2-methoxypyridin-4-yl)-3-methylpiperidin-4-yl)oxy)phenyl)-4-(trifluoromethyl)pyrrolidin-2-yl)acetonitrile 
• 1610035-80-7 2-((2R,4R)-1-(4-((1-(5-chloro-2-methoxypyridin-4-yl)piperidin-4-yl)methyl)phenyl)-4-methoxypyrrolidin-2-yl)acetic acid 
• 1610035-84-1 methyl 2-((2R,4R)-1-(4-((1-(5-chloro-2-methoxypyridin-4-yl)piperidin-4-yl)methyl)phenyl)-4-methoxypyrrolidin-2-yl)acetate 
• 1211534-25-6 4-bromo-5-chloro-2-methoxypyridine 

Relevant academic research and scientific papers

Discovery of AZD4573, a Potent and Selective Inhibitor of CDK9 That Enables Short Duration of Target Engagement for the Treatment of Hematological Malignancies

A CDK9 inhibitor having short target engagement would enable a reduction of Mcl-1 activity, resulting in apoptosis in cancer cells dependent on Mcl-1 for survival. We report the optimization of a series of amidopyridines (from compound 2), focusing on properties suitable for achieving short target engagement after intravenous administration. By increasing potency and human metabolic clearance, we identified compound 24, a potent and selective CDK9 inhibitor with suitable predicted human pharmacokinetic properties to deliver transient inhibition of CDK9. Furthermore, the solubility of 24 was considered adequate to allow i.v. formulation at the anticipated effective dose. Short-term treatment with compound 24 led to a rapid dose- and time-dependent decrease of pSer2-RNAP2 and Mcl-1, resulting in cell apoptosis in multiple hematological cancer cell lines. Intermittent dosing of compound 24 demonstrated efficacy in xenograft models derived from multiple hematological tumors. Compound 24 is currently in clinical trials for the treatment of hematological malignancies.

PYRROLO-AROMATIC HETEROCYCLIC COMPOUND, PREPARATION METHOD THEREFOR, AND MEDICAL USE THEREOF

The present invention relates to pyrrolo-aromatic heterocyclic compounds, a preparation method therefor and medical use thereof. Particularly, the present invention relates to a compound represented by formula I, a preparation method therefor, a pharmaceu

Chemical Compounds

Provided are a series of novel pyridine or pyrimidine derivatives which inhibit CDK9 and may be useful for the treatment of hyperproliferative diseases. In particular the compounds are of use in the treatment of proliferative disease such as cancer including hematological malignancies such as acute myeloid leukemia, multiple myeloma, chronic lymphocytic leukemia, diffuse large B cell lymphoma, Burkitt's lymphoma, follicular lymphoma and solid tumors such as breast cancer, lung cancer, neuroblastoma and colon cancer.

Discovery and analgesic evaluation of 8-chloro-1,4-dihydropyrido[2,3- b ]pyrazine-2,3-dione as a novel potent d -amino acid oxidase inhibitor

A series of 5-azaquinoxaline-2,3-dione derivatives were synthesized and evaluated on d-amino acid oxidase (DAAO) inhibition as potential α-hydroxylactam-based inhibitors. The potent inhibitory activities in vitro suggested that 5-nitrogen could significantly enhance the binding affinity by strengthening relevant hydrogen bond interactions. The analgesic effects of intrathecal and systemic injection of 8-chloro-1,4-dihydropyrido[2,3-b]pyrazine-2,3-dione, a representative molecule of 5-azaquinoxaline-2,3-dione, were investigated in rodents. This research not only confirmed the analgesic effect of the DAAO inhibitors but provided a new class of chemical entities with oral application potential for the treatment of chronic pain and morphine analgesic tolerance.

Dihydropyrazole GPR40 modulators

The present invention provides compounds of Formula (I): or a stereoisomer, or a pharmaceutically acceptable salt thereof, wherein all of the variables are as defined herein. These compounds are GPR40 G protein-coupled receptor modulators which may be used as medicaments.

Discovery and Structure-Guided Optimization of Diarylmethanesulfonamide Disrupters of Glucokinase-Glucokinase Regulatory Protein (GK-GKRP) Binding: Strategic Use of a N → S (nN → σ? S-X) Interaction for Conformational Constraint

The HTS-based discovery and structure-guided optimization of a novel series of GKRP-selective GK-GKRP disrupters are revealed. Diarylmethanesulfonamide hit 6 (hGK-hGKRP IC50 = 1.2 μM) was optimized to lead compound 32 (AMG-0696; hGK-hGKRP IC50 = 0.0038 μM). A stabilizing interaction between a nitrogen atom lone pair and an aromatic sulfur system (nN → σ?S-X) in 32 was exploited to conformationally constrain a biaryl linkage and allow contact with key residues in GKRP. Lead compound 32 was shown to induce GK translocation from the nucleus to the cytoplasm in rats (IHC score = 0; 10 mg/kg po, 6 h) and blood glucose reduction in mice (POC = -45%; 100 mg/kg po, 3 h). X-ray analyses of 32 and several precursors bound to GKRP were also obtained. This novel disrupter of GK-GKRP binding enables further exploration of GKRP as a potential therapeutic target for type II diabetes and highlights the value of exploiting unconventional nonbonded interactions in drug design.

PYRROLIDINE GPR40 MODULATORS

The present invention provides compounds of Formula (I): or a stereoisomer, or a pharmaceutically acceptable salt thereof, wherein all of the variables are as defined herein. These compounds are GPR40 G protein-coupled receptor modulators which may be used as medicaments.

PYRROLO[2,3-B]PYRIDINE CDK9 KINASE INHIBITORS

Disclosed are compounds of Formula (IIa), wherein R1, R2, R3A, R3B, R3C, R3D, R3E, and R4 are as defined in the specification, and pharmaceutically acceptable salts thereof. The compounds may be used as agents in the treatment of diseases, including cancer. Also provided are pharmaceutical compositions comprising one or more compounds of Formula (IIa)

PYRIDINE CDK9 KINASE INHIBITORS

Disclosed are compound of Formula (Ia), wherein R2, R12, R16, J, Q, X, Y and Z are as defined in the specification, and pharmaceutically acceptable salts thereof.The compounds may be used as agents in the treatment of diseases, including cancer. Also provided are pharmaceutical compositions comprising one or more compounds of Formula (Ia).

Discovery of a new series of Aurora inhibitors through truncation of GSK1070916

Novel Aurora inhibitors were identified truncating clinical candidate GSK1070916. Many of these truncated compounds retained potent activity against Aurora B with good antiproliferative activity. Mechanistic studies suggested that these compounds, dependi