956907-34-9

Usage

Uses

Used in Organic Synthesis:
1-2-[(Tetrahydro-2H-pyran-2-yl)oxy]ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole is used as a building block for the synthesis of new compounds with potential biological activity. Its unique structure allows for the development of advanced materials and contributes to the creation of pharmaceuticals with novel properties.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 1-2-[(Tetrahydro-2H-pyran-2-yl)oxy]ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole is utilized as a key intermediate in the design and synthesis of pharmaceuticals. Its complex structure enables the exploration of new chemical spaces and the discovery of compounds with therapeutic potential.
Used in Laboratory Research:
1-2-[(Tetrahydro-2H-pyran-2-yl)oxy]ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole serves as a reagent in various laboratory reactions, facilitating the study of chemical processes and the development of new synthetic methodologies. Its presence in research settings aids scientists in understanding its reactivity and potential applications in different chemical transformations.

Upstream product

• 17739-45-6 2-(2-bromoethoxy)tetrahydropyran 
• 1195-66-0 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 269410-08-4 pyrazole-4-boronic acid pinacol ester 

Downstream Products

• 1227611-60-0 2-(4-{3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]-pyridin-5-yl}pyrazol-1-yl)ethanol 
• 1323919-71-6 2-(2-fluoro-phenyl)-4-(5-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-pyrazol-4-yl}-pyridin-3-yl)-[1,8]naphthyridine 
• 1323917-26-5 2-(4-{5-[2-(2-fluoro-phenyl)-[1,8]naphthyridin-4-yl]-pyridin-3-yl}-pyrazol-1-yl)-ethanol 
• 1354759-09-3 2-[2-(2-fluoro-phenyl)-pyridin-4-yl]-6-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-pyrazol-4-yl}-pyrazine 
• 1448429-60-4 6-[1-(2-tetrahydro-2H-pyran-2-yloxyethyl)-1H-pyrazol-4-yl]-1H-indazole 
• 1460285-72-6 3-(4-{1-[2-(tetrahydro-pyran-2-yloxy)ethyl]-1H-pyrazol-4-yl}phenyl)-2H-pyrrolo[1,2-a]pyrazin-1-one 
• 1460285-73-7 3-{4-[1-(2-hydroxy-ethyl)-1H-pyrazol-4-yl]phenyl}-2H-pyrrolo[1,2-a]pyrazin-1-one 

Relevant academic research and scientific papers

AZAINDOLE DERIVATIVE AND USE THEREOF AS FGFR AND C-MET INHIBITOR

A series of pyrazolopymidine derivatives, and use thereof in the preparation of a medicament for treating disease associated with FGFR and c-Met. The pyrazolopymidine derivative is a compound represented by formula (I), a tautomer, or a pharmaceutically acceptable salt thereof.

Fused Pyrazoles as FGFR Inhibitors

The present invention relates to fused pyrazole derivatives, and pharmaceutical compositions including the same, that are inhibitors of one or more FGFR enzymes and are useful in the treatment of FGFR-associated diseases such as cancer.

Discovery of 2-{3-[2-(1-isopropyl-3-methyl-1H-1,2-4-triazol-5-yl)-5,6- dihydrobenzo[f]imidazo[1,2- d ][1,4]oxazepin-9-yl]-1H-pyrazol-1-yl}-2- methylpropanamide (GDC-0032): A β-sparing phosphoinositide 3-kinase inhibitor with high unbound exposure and robust in vivo antitumor activity

Dysfunctional signaling through the phosphoinositide 3-kinase (PI3K)/AKT/mTOR pathway leads to uncontrolled tumor proliferation. In the course of the discovery of novel benzoxepin PI3K inhibitors, we observed a strong dependency of in vivo antitumor activity on the free-drug exposure. By lowering the intrinsic clearance, we derived a set of imidazobenzoxazepin compounds that showed improved unbound drug exposure and effectively suppressed growth of tumors in a mouse xenograft model at low drug dose levels. One of these compounds, GDC-0032 (11l), was progressed to clinical trials and is currently under phase I evaluation as a potential treatment for human malignancies.

Discovery of a novel class of exquisitely selective mesenchymal-epithelial transition factor (c-MET) protein kinase inhibitors and identification of the clinical candidate 2-(4-(1-(Quinolin-6-ylmethyl)-1 H -[1,2,3]triazolo[4,5- b ]pyrazin-6-yl)-1 H -pyrazol-1-yl)ethanol (PF-04217903) for the treatment of cancer

The c-MET receptor tyrosine kinase is an attractive oncology target because of its critical role in human oncogenesis and tumor progression. An oxindole hydrazide hit 6 was identified during a c-MET HTS campaign and subsequently demonstrated to have an unusual degree of selectivity against a broad array of other kinases. The cocrystal structure of the related oxindole hydrazide c-MET inhibitor 10 with a nonphosphorylated c-MET kinase domain revealed a unique binding mode associated with the exquisite selectivity profile. The chemically labile oxindole hydrazide scaffold was replaced with a chemically and metabolically stable triazolopyrazine scaffold using structure based drug design. Medicinal chemistry lead optimization produced 2-(4-(1-(quinolin-6- ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)-1H-pyrazol-1-yl)ethanol (2, PF-04217903), an extremely potent and exquisitely selective c-MET inhibitor. 2 demonstrated effective tumor growth inhibition in c-MET dependent tumor models with good oral PK properties and an acceptable safety profile in preclinical studies. 2 progressed to clinical evaluation in a Phase I oncology setting.

BENZOXEPIN PI3K INHIBITOR COMPOUNDS AND METHODS OF USE

Benzoxepin compounds of Formula I, and including stereoisomers, geometric isomers, tautomers, solvates, metabolites and pharmaceutically acceptable salts thereof, wherein: Z1 is CR1 or N; Z2 is CR2 or N; Z3 is CR3 or N; Z4 is CR4 or N; and where (i) X1 is N and X2 is S, (ii) X1 is S and X2 is N, (iii) X1 is CR7 and X2 is S, (iv) X1 is S and X2 is CR7; (v) X1 is NR8 and X2 is N, (vi) X1 is N and X2 is NR8, (vii) X1 is CR7 and X2 is O, (viii) X1 is O and X2 is CR7, (ix) X1 is CR7 and X2 is C(R7)2, (x) X1 is C(R7)2 and X2 is CR7; (xi) X1 is N and X2 is O, or (xii) X1 is O and X2 is N, are useful for inhibiting lipid kinases including p110 alpha and other isoforms of PI3K, and for treating disorders such as cancer mediated by lipid kinases. Methods of using compounds of Formula I for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

3-(3-PYRIMIDIN-2-YLBENZYL)-1,2,4-TRIAZOLO[4,3-B]PYRIDAZINE DERIVATIVES AS MET KINASE INHIBITORS

Compounds of the formula (I), in which R1, R2, R3, R3′, R4 have the meanings indicated in Claim 1, are inhibitors of tyrosine kinases, in particular of Met kinase, and can be employed, inter alia, for the treatment of tumours.