910543-72-5

Usage

Uses

Used in Pharmaceutical Industry:
3-AMINO-5-BROMO-1-METHYLPYRIDIN-2(1H)-ONE is used as a key intermediate in the synthesis of 5-phenylpyridin-2(1H)-one derivatives. These derivatives have demonstrated potent inhibitory activity against Bruton's tyrosine kinase (BTK), a critical enzyme involved in various inflammatory and immune responses. By targeting BTK, these derivatives have shown promise as effective treatments for rheumatoid arthritis, a chronic autoimmune disorder characterized by inflammation and pain in the joints.
In the development of antiarthritic agents, 3-AMINO-5-BROMO-1-METHYLPYRIDIN-2(1H)-ONE contributes to the creation of reversible BTK inhibitors. These inhibitors are designed to alleviate the symptoms of rheumatoid arthritis by modulating the immune system's response and reducing inflammation. The use of 3-AMINO-5-BROMO-1-METHYLPYRIDIN-2(1H)-ONE in the synthesis of such inhibitors highlights its importance in advancing therapeutic options for patients suffering from this debilitating condition.
Furthermore, the versatility of 3-AMINO-5-BROMO-1-METHYLPYRIDIN-2(1H)-ONE as a reagent allows for the exploration of its potential applications in other areas of medicinal chemistry. Its unique structure and functional groups make it a promising candidate for the development of additional pharmaceutical agents targeting a variety of diseases and disorders. As research continues, the applications of 3-AMINO-5-BROMO-1-METHYLPYRIDIN-2(1H)-ONE may expand, further solidifying its significance in the field of drug discovery and development.

Upstream product

• 153888-45-0 5-bromo-1-methyl-3-nitropyridine-2(1H)-one 
• 15862-34-7 5-bromo-3-nitro-1H-pyridin-2-one 
• 1013-88-3 Benzophenone imine 
• 14529-54-5 3,5-dibromo-1-methyl-1H-pyridin-2-one 
• 15862-34-7 5-bromo-3-nitro-2-pyridone 
• 1072-97-5 5-bromo-2-pyridylamine 

Downstream Products

• 1011797-06-0 N-[3-(5-amino-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-2-methyl-phenyl]-4-tert-butyl-benzamide 
• 1178884-09-7 6-(dimethylamino)-2-(2-(hydroxymethyl)-3-(1-methyl-5-(5-(morpholine-4-carbonyl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)phenyl)-3,4-dihydroisoquinolin-1(2H)-one 
• 1198765-28-4 C₃₄H₃₄N₆O₅ 
• 1178884-20-2 6-tert-butyl-2-(2-hydroxymethyl-3-{1-methyl-5-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-phenyl)-3,4-dihydro-2H-isoquinolin-1-one 
• 1198765-39-7 acetic acid 2(5-amino-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-6-(6-dimethylamino-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-benzyl ester 
• 1198765-36-4 C₁₄H₁₂BrN₃O₃S 

Relevant academic research and scientific papers

HETEROCYCLIC COMPOUNDS AS BET INHIBITORS

Novel bromodomain and extraterminal domain (BET) inhibitors and to therapeutic methods of treating conditions and diseases using these novel BET inhibitors are provided.

Stereochemical Differences in Fluorocyclopropyl Amides Enable Tuning of Btk Inhibition and Off-Target Activity

Bruton's tyrosine kinase (Btk) is thought to play a pathogenic role in chronic immune diseases such as rheumatoid arthritis and lupus. While covalent, irreversible Btk inhibitors are approved for treatment of hematologic malignancies, they are not approved for autoimmune indications. In efforts to develop additional series of reversible Btk inhibitors for chronic immune diseases, we sought to differentiate from our clinical stage inhibitor fenebrutinib using cyclopropyl amide isosteres of the 2-aminopyridyl group to occupy the flat, lipophilic H2 pocket. While drug-like properties were retained - and in some cases improved - a safety liability in the form of hERG inhibition was observed. When a fluorocyclopropyl amide was incorporated, Btk and off-target activity was found to be stereodependent and a lead compound was identified in the form of the (R,R)- stereoisomer.

New Pyridinones and Isoquinolinones as Inhibitors of the Bromodomain BRD9

The present invention encompasses compounds of general formula (I) wherein the groups R1 to R9, X1 and X2 have the meanings given in the claims and in the specification. The compounds of the invention are suitable for the treatment of diseases characterized by excessive or abnormal cell proliferation, e.g. cancer, pharmaceutical preparations containing such compounds and their uses as a medicament.

Synthesis and profiling of a 3-aminopyridin-2-one-based kinase targeted fragment library: Identification of 3-amino-5-(pyridin-4-yl)pyridin-2(1H)-one scaffold for monopolar spindle 1 (MPS1) and Aurora kinases inhibition

Screening a 3-aminopyridin-2-one based fragment library against a 26-kinase panel representative of the human kinome identified 3-amino-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2(1H)-one (2) and 3-amino-5-(pyridin-4-yl)pyridin-2(1H)-one (3) as ligand efficient inhibitors of the mitotic kinase Monopolar Spindle 1 (MPS1) and the Aurora kinase family. These kinases are well recognised as attractive targets for therapeutic intervention for treating cancer. Elucidation of the binding mode of these fragments and their analogues has been carried out by X-ray crystallography. Structural studies have identified key interactions with a conserved lysine residue and have highlighted potential regions of MPS1 which could be targeted to improve activity and selectivity.

HETEROARYL PYRIDONE AND AZA-PYRIDONE COMPOUNDS AS INHIBITORS OF BTK ACTIVITY

Heteroaryl pyridone and aza-pyridone compounds of Formula I are provided, where one or two of X, X, and Xare N, and including stereoisomers, tautomers, and pharmaceutically acceptable salts thereof, useful for inhibiting Btk kinase, and for treating immune disorders such as inflammation mediated by Btk kinase. Methods of using compounds of Formula I foranddiagnosis, and treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

Development of a scalable synthesis of a Bruton's tyrosine kinase inhibitor via C-N and C-C bond couplings as an end game strategy

A scalable and convergent synthesis of a BTK (Bruton's tyrosine kinase) inhibitor has been developed. Synthetic routes to key intermediates were explored for the scale-up campaign, especially the process for 6-dimethylaminodihydroisoquinolinone, which was prepared via a regioselective cyclization of an isocyanate, mediated by AlCl3. Improved routes to key building blocks were demonstrated by expedient multikilogram productions. The target compound was assembled through a Pd-catalyzed amidation reaction followed by a Suzuki-Miyaura cross-coupling reaction.

An expeditious copper-catalyzed access to 3-aminoquinolinones, 3-aminocoumarins and anilines using sodium azide

An efficient copper-catalyzedin in situ C-(sp2)-NH2 bond formation to provide a range of 3-aminoquinolin-2(1H)-ones and 3-aminocoumarins from 3-bromoquinolinones and 3-bromocoumarins, respectively, has been achieved. The reaction conditions involve the use of copper powder as the catalyst, eco-friendly ethanol as the solvent in the pres ence of pipecolinic acid as the ligand and ascorbic acid as the additive. The efficiency of this practical method was demonstrated in the synthesis of various anilines.

CERTAIN SUBSTITUTED AMIDES, METHOD OF MAKING, AND METHOD OF USE THEREOF

Compounds of Formula I that inhibit Btk are described herein. Pharmaceutical compositions comprising at least one compound of Formula I, together with at least one pharmaceutically acceptable vehicle chosen from carriers, adjuvants, and excipients, are de

Certain Substituted Amides, Method of Making, and Method of Use Thereof

At least one chemical entity chosen from compounds of Formula 1 and pharmaceutically acceptable salts, solvates, chelates, non-covalent complexes, prodrugs, and mixtures thereof is described herein. Pharmaceutical compositions comprising at least one chemical entity of the invention, together with at least one pharmaceutically acceptable vehicle chosen from carriers adjuvants, and excipients, are described. Methods of treating patients suffering from certain diseases responsive to inhibition of Btk activity and/or B-cell activity are described. Methods for determining the presence of Btk in a sample are described.

Calcitonin gene-related peptide (CGRP) receptor antagonists: Investigations of a pyridinone template

In our effort to find potent, orally bioavailable CGRP receptor antagonists for the treatment of migraine, a novel series based on a pyridinone template was investigated. After optimizing the privileged structure and the placement of the attached phenyl r