1369959-12-5

Usage

Uses

Used in Pharmaceutical Industry:
5-Chloro-3-nitro-1H-pyrazole is used as a synthetic intermediate for the production of various pharmaceuticals. Its unique structure allows it to be a building block in the creation of new drugs, potentially contributing to advancements in medicinal chemistry and the treatment of various diseases.
Used in Agrochemical Industry:
In the agrochemical sector, 5-Chloro-3-nitro-1H-pyrazole serves as an intermediate in the synthesis of crop protection products. Its reactivity and chemical properties make it suitable for the development of effective agents that can protect crops from pests and diseases, thereby enhancing agricultural productivity and crop yields.
The specific applications and properties of 5-chloro-3-nitro-1H-pyrazole may vary based on the synthesis method and the particular use for which it is intended, highlighting the compound's versatility in both the pharmaceutical and agrochemical fields.

Upstream product

• 1369959-11-4 3-chloro-1-nitro-1H-pyrazole 

Downstream Products

• 916211-79-5 3-chloro-1H-pyrazol-5-amine 

Relevant academic research and scientific papers

PYRAZOLOPYRIMIDINE AS MALT-1 INHIBITORS

The invention provides a compound of formula (I): herein R1, R2 and R3 of series (x), (y) and (z) are as defined in the specification which are potent inhibitors of the enzyme MALT1 and are useful in an immunooncology approach to the treatment of cancer, especially bladder cancer, colon cancer, hepatocellular cancer or small cell or non-small cell lung cancer.

COMPOUNDS FOR MALT1 DEGRADATION

Provided herein are bifunctional compounds that inhibit MALTl and/or promote targeted ubiquitination for the degradation of MALTl. In particular, provided are compounds that can bind MALTl, a protein whose activity is responsible for constitutive NF-KB signaling in certain cancers (e.g., activated B-cell diffuse large B-cell lymphoma (ABC-DLBCL)), and can assist in its degradation by recruiting an E3 ubiquitin ligase (e.g., Cereblon, VHL), which can ubiquitinate MALTl, marking it for proteasome degradation. Also provided are pharmaceutical compositions comprising the bifunctional compounds, methods of treating cancer with the bifunctional compounds, methods of promoting the degradation of MALTl, and methods of binding E3 ubiquitin ligase activity in a subject by administering a compound or composition described herein.

Discovery of ((S)-5-(methoxymethyl)-7-(1-methyl-1 H -indol-2-yl)-2- (trifluoromethyl)-4,7-dihydropyrazolo[1,5- a ]pyrimidin-6-yl)((S)-2-(3- methylisoxazol-5-yl)pyrrolidin-1-yl)methanone as a potent and selective I Kur inhibitor

Previously disclosed dihydropyrazolopyrimidines are potent and selective blockers of IKur current. A potential liability with this chemotype is the formation of a reactive metabolite which demonstrated covalent binding to protein in vitro. When substituted at the 2 or 3 position, this template yielded potent IKur inhibitors, with selectivity over hERG which did not form reactive metabolites. Subsequent optimization for potency and PK properties lead to the discovery of ((S)-5-(methoxymethyl)-7-(1-methyl-1H-indol- 2-yl)-2-(trifluoromethyl)-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)((S) -2-(3-methylisoxazol-5-yl)pyrrolidin-1-yl)methanone (13j), with an acceptable PK profile in preclinical species and potent efficacy in the preclinical rabbit atrial effective refractory period (AERP) model.