1246892-67-0

Usage

Structure

Contains a oxazoloazepine ring and a tetrahydro-2-pyridinyl group

Class

Heterocyclic compound

Usage

Commonly used in pharmaceutical research and drug development

Potential Therapeutic Applications

Due to its unique structure and properties

Ongoing Scientific Study

Subject of current research for its biological activities and potential uses

Need for Further Research

To explore its pharmacological and medicinal properties.

Upstream product

• 1246891-83-7 2-(pyridin-2-yl)-5-tosyl-5,6,7,8-tetrahydro-4H-oxazolo[4,5-c]azepine 
• 1247884-75-8 benzyl 7,8-dihydro-2-(pyridin-2-yl)-4H-oxazolo[4,5-c]azepine-5(6H)-carboxylate 

Downstream Products

• 1246891-84-8 3-(2-(pyridin-2-yl)-7,8-dihydro-4H-oxazolo[4,5-c]azepin-5(6H)-yl)benzonitrile 

Relevant academic research and scientific papers

Design, synthesis, and structure-activity relationships of novel bicyclic azole-amines as negative allosteric modulators of metabotropic glutamate receptor 5

A novel series of diaryl bicyclic azole-amines that are potent selective negative modulators of metabotropic glutamate receptor 5 (mGluR5) were identified through rational design. An initial hit compound 5a of modest potency (IC50 = 1.2 μM) was synthesized. Evaluation of structure-activity relationships (SAR) on the left-hand side of the molecule revealed a preference for a 2-substituted pyridine group linked directly to the central heterocycle. Variation of the central azolo-amine portion of the molecule revealed a preference for the [4,5-c]-oxazoloazepine scaffold, while right-hand side variants showed a preference for ortho- and meta-substituted benzene rings linked directly to the tertiary amine of the saturated heterocycle. These iterations led to the synthesis of 29b, a potent (IC50 = 16 nM) and selective negative modulator that showed good brain penetrance, high receptor occupancy, and a duration of action greater than 1 h in rat when administered intraperitoneally. Formal PK studies in rat and Rhesus monkey revealed a short half-life that was attributable to high first-pass clearance.

COMPOUNDS FOR TREATING DISORDERS MEDIATED BY METABOTROPIC GLUTAMATE RECEPTOR 5, AND METHODS OF USE THEREOF

Provided herein are compounds and methods of synthesis thereof. The compounds provided herein are useful for the treatment, prevention, and/or management of various disorders, such as neurological disorders, psychiatric disorders, neuromuscular disorders, gastrointestinal disorders, lower urinary tract disorder, and cancer. Compounds provided herein modulate the activity of metabotropic glutamate receptor 5 (mGluR5) in the central nervous system or the periphery. Pharmaceutical formulations containing the compounds and their methods of use are also provided herein.