1314893-92-9

Usage

Uses

Used in Medicinal Chemistry:
3-bromo-6-chloropyrazolo[1,5-a]pyrimidine is utilized as a key building block in the synthesis of biologically active compounds. Its unique structure allows for the development of pharmaceuticals with specific therapeutic properties, making it a valuable asset in the field of medicinal chemistry.
Used in Drug Discovery and Development:
3-bromo-6-chloropyrazolo[1,5-a]pyrimidine is also recognized for its potential biological activities, which have been the subject of research in drug discovery and development. Its exploration as a precursor to pyrazolopyrimidine-based drugs highlights its importance in creating novel therapeutic agents with potential applications in treating various diseases and conditions.
Used in Pharmaceutical Production:
As a key intermediate in the production of pyrazolopyrimidine-based drugs, 3-bromo-6-chloropyrazolo[1,5-a]pyrimidine plays a crucial role in the manufacturing process of these medications. Its presence in the synthesis pathway ensures the creation of effective and targeted pharmaceuticals for a range of medical needs.

Upstream product

• 16461-94-2 3-amino-4-bromo-1H-pyrazole 
• 36437-19-1 2-chloromalonaldehyde 
• 2024538-64-3 6-chloropyrazolo[1,5-a]pyrimidine 

Downstream Products

• 1314893-24-7 (1R,2R)-2-(([5-chloro-4-(6-chloropyrazolo[1,5-a]-pyrimidin-3-yl)-thiophen-2-yl]carbonyl)-amino)-3,3-difluorocyclohexanaminium chloride 
• 1314894-07-9 tert-butyl (1R,2R)-2-({[4-(6-chloropyrazolo[1,5-a]pyrimidin-3-yl)-5-methylthiophen-2-yl]carbonyl}amino)-3,3-difluorocyclohexylcarbamate 
• 1314893-26-9 N-((1R,6R)-6-amino-2,2-difluorocyclohexyl)-4-(6-chloropyrazolo[1,5-a]pyrimidin-3-yl)-5-methylthiophene-2-carboxamide 
• 1314893-30-5 N-[(1R,6S)-6-amino-2,2-difluorocyclohexyl]-4-(6-chloropyrazolo[1,5-a]pyrimidin-3-yl)-5-ethylthiophene-2-carboxamide 

Relevant academic research and scientific papers

A Scaffold-Hopping Strategy toward the Identification of Inhibitors of Cyclin G Associated Kinase

We recently reported the discovery of isothiazolo[4,3-b]pyridine-based inhibitors of cyclin G associated kinase (GAK) displaying low nanomolar binding affinity for GAK and demonstrating broad-spectrum antiviral activity. To come up with novel core structures that act as GAK inhibitors, a scaffold-hopping approach was applied starting from two different isothiazolo[4,3-b]pyridines. In total, 13 novel 5,6- and 6,6-fused bicyclic heteroaromatic scaffolds were synthesized. Four of them displayed GAK affinity with Kd values in the low micromolar range that can serve as chemical starting points for the discovery of GAK inhibitors based on a different scaffold.

HETEROARYL SUBSTITUTED AMINOPYRIDINE COMPOUNDS

Disclosed are compounds of Formula (I) Formula(I) or salts thereof, wherein HET is a heteroaryl selected from oxazolyl, pyrazolyl, imidazo[l,2-b]pyridazin-3-yl, and pyrazolo[l,5-a]pyrimidin-3-yl, wherein said heteroaryl is attached to the pyridinyl group in the compound of Formula (I) by a carbon ring atom in the heteroaryl and wherein said heteroaryl is substituted with zero to 2 Rb; and R1, R3, and Rb are define herein. Also disclosed are methods of using such compounds as modulators of IRAK4, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing inflammatory and autoimmune diseases, or in the treatment of cancer.

HETEROARYL SUBSTITUTED AMINOPYRIDINE COMPOUNDS

Disclosed are compounds of Formula (I) or salts thereof, wherein: HET is a heteroaryl selected from imidazo[1,2-b]pyridazinyl and pyrazolo[1,5-a]pyrimidinyl, wherein said heteroaryl is attached to the pyridinyl group in the compound of Formula (I) by a carbon ring atom in the heteroaryl and wherein said heteroaryl is substituted with zero to 2 Rb; A is pyrazolyl, imidazolyl, or triazolyl, each substituted with zero or 1 Ra; and R3, Ra, and Rb are define herein. Also disclosed are methods of using such compounds as modulators of IRAK4, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing inflammatory and autoimmune diseases, or in the treatment of cancer.

PYRAZOLO[1,5-A]PYRIMIDINES AS MARK INHIBITORS

The invention encompasses pyrazolo[1,5-a]pyrimidine derivatives which selectively inhibit microtubule affinity regulating kinase (MARK) and are therefore useful for the treatment or prevention of Alzheimer's disease. Pharmaceutical compositions and methods of use are also included.