459448-06-7

Usage

Uses

Used in Medicinal Chemistry:
6-BROMO-3-ISOPROPYL-[1,2,4]TRIAZOLO[4,3-A]PYRIDINE is utilized as a key intermediate in the synthesis of biologically active molecules. Its presence in the molecular structure allows for the development of new drugs with diverse therapeutic applications.
Used in Drug Discovery:
In the field of drug discovery, 6-BROMO-3-ISOPROPYL-[1,2,4]TRIAZOLO[4,3-A]PYRIDINE serves as a valuable building block for the creation of novel compounds with potential therapeutic effects. Its unique structural features contribute to the design and optimization of new drug candidates for various diseases and conditions.
Used in Pharmaceutical Industry:
6-BROMO-3-ISOPROPYL-[1,2,4]TRIAZOLO[4,3-A]PYRIDINE is employed as a crucial component in the development of new pharmaceuticals. Its incorporation into drug molecules can enhance their efficacy, selectivity, and pharmacokinetic properties, leading to improved treatment options for patients.

Upstream product

• 668980-99-2 6-bromo-3-isopropyl[1,2,4]triazolo[4,3-a]pyridine hydrochloride 
• 77992-44-0 5-bromo-2-hydrazinylpyridine 
• 79-30-1 isobutyryl chloride 
• 459448-05-6 isobutyric acid N'-(5-bromo-pyridin-2-yl)-hydrazide 
• 1344738-15-3 C₉H₁₂BrN₃ 

Downstream Products

• 459448-04-5 3-isopropyl-[1,2,4]triazolo[4,3-a]-6-pyridinecarboxaldehyde 
• 745827-32-1 {2-[(3-isopropyl[1,2,4]triazolo[4,3-a]pyridin-6-yl)thio]phenyl}methanol 
• 876461-40-4 C₁₆H₁₃BrF₃N₃S 
• 876461-41-5 C₁₆H₁₃F₄N₃S 
• 876461-42-6 C₁₅H₁₂Cl₃N₃S 
• 1344738-33-5 1-{1-[3-(benzyloxy)phenyl]-3-tert-butyl-1H-pyrazol-5-yl}-3-{2-[(3-isopropyl[1,2,4]triazolo[4,3-a]pyridin-6-yl)thio]benzyl}urea 
• 1344737-98-9 1-{1-(3-hydroxyphenyl)-3-[1-methyl-1-(methylsulfinyl)ethyl]-1H-pyrazol-5-yl}-3-{2-[(3-isopropyl[1,2,4]triazolo[4,3-a]pyridin-6-yl)thio]benzyl}urea 
• 745828-08-4 1-{2-[(3-isopropyl[1,2,4]triazolo[4,3-a]pyridin-6-yl)thio]phenyl}methanamine 

Relevant academic research and scientific papers

Design and synthesis of inhaled p38 inhibitors for the treatment of chronic obstructive pulmonary disease

This paper describes the identification and optimization of a novel series of DFG-out binding p38 inhibitors as inhaled agents for the treatment of chronic obstructive pulmonary disease. Structure based drug design and "inhalation by design" principles have been applied to the optimization of the lead series exemplied by compound 1a. Analogues have been designed to be potent and selective for p38, with an emphasis on slow enzyme dissociation kinetics to deliver prolonged lung p38 inhibition. Pharmacokinetic properties were tuned with high intrinsic clearance and low oral bioavailability in mind, to minimize systemic exposure and reduce systemically driven adverse events. High CYP mediated clearance and glucuronidation were targeted to achieve high intrinsic clearance coupled with multiple routes of clearance to minimize drug-drug interactions. Furthermore, pharmaceutical properties such as stability, crystallinity, and solubility were considered to ensure compatibility with a dry powder inhaler. 1ab (PF-03715455) was subsequently identified as a clinical candidate from this series with efficacy and safety profiles confirming its potential as an inhaled agent for the treatment of COPD.

Continued exploration of the triazolopyridine scaffold as a platform for p38 MAP kinase inhibition

The structure based drug design, synthesis and structure-activity relationship of a series of C6 sulfur linked triazolopyridine based p38 inhibitors are described. The metabolic deficiencies of this series were overcome through changes in the C6 linker fr

Triazolopyridinylsulfanyl derivatives as p38 MAP kinase inhibitors

A compound of formula (I), or a pharmaceutically acceptable salt and/or solvate (including hydrate) thereof; and the use of a compound of formula (I) in the treatment of a TNF-mediated disease, disorder, or condition, or a p38-mediated disease, disorder, or condition, in particular the allergic and non-allergic airways diseases, more particularly obstructive or inflammatory airways diseases, preferably chronic obstructive pulmonary disease.

DI AND TRIFLUORO-TRIAZOLO-PYRIDINES ANTI-INFLAMMATORY COMPOUNDS

The present invention relates to novel triazolo-pyridines of the formula (I) wherein R1 is fluoro; s is an integer from two to three; R2 is (C3-C6)cycloalkyl optionally substituted by one or two moieties independently selected from the group consisting of halo, (Cl-C4)alkyl, hydroxy, (Cl-C6)alkoxy and (C1-C6)alkyl-(C=O)-0-; or R2 is (Cl-C6)alkyl optionally substituted by one or two moieties independently selected from the group consisting of halo, (C1-C6)alkyl, hydroxy, (C1-C6)alkoxy and (C1-C6)alkyl-(C=O)-0-; with the proviso that said compound of formula (I) cannot be 6-[4-(2,4-Difluoro-phenyl)-oxazol-5-yl]-3-isopropyl-[1,2,4]triazolo[4,3-a]pyridine; or 6-[4-(3,4-Difluoro-phenyl)-oxazol-5-yl]-3-isopropyl-[1,2,4]triazolo[4,3-a]pyridine; to intermediates for their preparation, to pharmaceutical compositions containing them and to their medicinal use. The compounds of the present invention are potent inhibitors of MAP kinases, preferably p38 kinase. They are useful in the treatment of inflammation, osteoarthritis, rheumatoid arthritis, cancer, repurfusion or ischemia in stroke or heart attack, autoimmune diseases and other disorders.

NOVEL PROCESSES AND INTERMEDIATES FOR PREPARING TRIAZOLO-PYRIDINES

The present invention relates and intermediates to a novel process for preparing triazolo-pyridines of the formula I wherein R1 is selected from the group consisting of hydrogen, (C,-C6)alkyl or other suitable substituents; R3 is selected from the group consisting óf hydrogen, (Cl-C6)alkyl or other suitable substituents; s is an integer from 0-5; R4is hydrogen or a suitable substituent and to intermediates for their preparation. The compounds prepared by the methods of the present invention are potent inhibitors of MAP kinases, preferably p38 kinase. They are useful in the treatment of inflammation, osteoarthritis, rheumatoid arthritis, cancer, reperfusion or ischemia in stroke or heart attack, autoimmune diseases and other disorders.

Alkyl-[4-(trifluorophenyl)-oxazol-5-yl]-triazolo-pyridines

The present invention relates to novel alkyl-[4-(trifluorophenyl)-oxazol-5-yl]-triazolo-pyridines, to intermediates and methods for their preparation, to pharmaceutical compositions containing them and to their medicinal use. The compounds of the present invention are potent inhibitors of MAP kinases, preferably p38 kinase. They are useful in the treatment of inflammation, osteoarthritis, rheumatoid arthritis, cancer, reperfusion or ischemia in stroke or heart attack, autoimmune diseases and other disorders.

Cycloalkyl-[4-(difluorophenyl)-oxazol-5-yl]-triazolo-pyridines

The present invention relates to novel cycloalkyl-[4-(difluorophenyl)-oxazol-5-yl]triazolo-pyridines, to intermediates for their preparation, to pharmaceutical compositions containing them and to their medicinal use. The compounds of the present invention are potent inhibitors of MAP kinases, preferably p38 kinase. They are useful in the treatment of inflammation, osteoarthritis, rheumatoid arthritis, cancer, reperfusion or ischemia in stroke or heart attack, autoimmune diseases and other disorders.

Alkyl-[4-(difluorophenyl)-oxazol-5-yl]-triazolo-pyridines

The present invention relates to novel alkyl-[4-(difluorophenyl)-oxazol-5-yl]-triazolo-pyridines, to intermediates for their preparation, to pharmaceutical compositions containing them and to their medicinal use. The compounds of the present invention are potent inhibitors of MAP kinases, preferably p38 kinase. They are useful in the treatment of inflammation, osteoarthritis, rheumatoid arthritis, cancer, reperfusion or ischemia in stroke or heart attack, autoimmune diseases and other disorders.

Novel crystalline forms of 3-isopropyl-6-[4-(2,5-difluoro-phenyl)-oxazol-5-yl]-[1,2,4]triazolo-[4,3-A]pyridine

The present invention relates to novel crystalline forms of 3-isopropyl-6-[4-(2,5-difluoro-phenyl)-oxazol-5-yl]-[1,2,4]triazolo-[4,3-a]pyridine to pharmaceutical compositions containing such crystal forms and to methods of treatment. 3-Isopropyl-6-[4-(2,5-difluoro-phenyl)-oxazol-5-yl]-[1,2,4]triazolo-[4,3-a]pyridine is a potent inhibitor of MAP kinases, preferably p38 kinase (MAPK14/CSBP/RK kinase). 3-Isopropyl-6-[4-(2,5-difluoro-phenyl)-oxazol-5-yl]-[1,2,4]triazolo-[4,3-a]pyridine is useful in the treatment of inflammation, osteoarthritis, rheumatoid arthritis, cancer, reperfusion or ischemia in stroke or heart attack, autoimmune diseases and other disorders.

Cycloalkyl-[4-(trifluorophenyl)-oxazol-5yl]-triazolo-pyridines

The present invention relates to novel cycloalkyl-[4-(trifluorophenyl)-oxazol-5-yl]-triazolo-pyridines, to intermediates for their preparation, to pharmaceutical compositions containing them and to their medicinal use. The compounds of the present invention are potent inhibitors of MAP kinases, preferably p38 kinase. They are useful in the treatment of inflammation, osteoarthritis, rheumatoid arthritis, cancer, reperfusion or ischemia in stroke or heart attack, autoimmune diseases and other disorders.