173600-05-0

Basic information

• Product Name: Methyl 1-isopropyl-1H-indazole-3-carboxylate
• Synonyms: Methyl 1-isopropyl-1H-indazole-3-carboxylate;1-Isopropyl-1H-indazole-3-carboxylic acid methyl ester;methyl 1-isopropyl-1H-indazol-3-ylcarboxylate
• CAS NO: 173600-05-0
• Molecular Formula: C12H14N2O2
• Molecular Weight: 218.25176
• Mol File: 173600-05-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 326.0±15.0 °C(Predicted)
• Appearance: /
• Density: 1.17±0.1 g/cm3(Predicted)
• PKA: -0.77±0.50(Predicted)
• CAS DataBase Reference: Methyl 1-isopropyl-1H-indazole-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 1-isopropyl-1H-indazole-3-carboxylate(173600-05-0)
• EPA Substance Registry System: Methyl 1-isopropyl-1H-indazole-3-carboxylate(173600-05-0)

Safety Data

• Hazardous Substances Data: 173600-05-0(Hazardous Substances Data)

Usage

General Description

Methyl 1-isopropyl-1H-indazole-3-carboxylate is a chemical compound with the molecular formula C13H15N2O2. It is a synthetic cannabinoid and an indazole-3-carboxylate derivative that acts as a potent agonist at the cannabinoid receptors CB1 and CB2. Methyl 1-isopropyl-1H-indazole-3-carboxylate has been found in various synthetic cannabinoid products and is known for its psychoactive effects, including euphoria, relaxation, and altered perception. It is important to note that the use of this compound for recreational purposes can be dangerous and potentially harmful to human health, as its long-term effects have not been extensively studied. As such, its use is often associated with legal and health risks.

Upstream product

• 75-30-9 2-iodo-propane 
• 1196678-72-4 indazol-3-carboxylic acid 
• 4498-67-3 1H-Indazole-3-carboxylic acid 
• 67-56-1 methanol 
• 173600-14-1 1-isopropyl-1H-indazole-3-carboxylic acid 
• 43120-28-1 methyl 1H-indazole-3-carboxylate 

Downstream Products

• 173600-14-1 1-isopropyl-1H-indazole-3-carboxylic acid 

Relevant articles and documents

Discovery and Preclinical Characterization of Usmarapride (SUVN-D4010): A Potent, Selective 5-HT4Receptor Partial Agonist for the Treatment of Cognitive Deficits Associated with Alzheimer's Disease

A series of oxadiazole derivatives were synthesized and evaluated as 5-hydroxytryptamine-4 receptor (5-HT4R) partial agonists for the treatment of cognitive deficits associated with Alzheimer's disease. Starting from a reported 5-HT4R antagonist, a systematic structure-activity relationship was conducted, which led to the discovery of potent and selective 5-HT4R partial agonist 1-isopropyl-3-{5-[1-(3-methoxypropyl) piperidin-4-yl]-[1,3,4]oxadiazol-2-yl}-1H-indazole oxalate (Usmarapride, 12l). It showed balanced physicochemical-pharmacokinetic properties with robust nonclinical efficacy in cognition models. It also showed disease-modifying potential, as it increased neuroprotective soluble amyloid precursor protein alpha levels, and dose-dependent target engagement and correlation of efficacy with oral exposures. Phase 1 clinical studies have been completed and projected efficacious concentration was achieved without any major safety concerns. Phase 2 enabling long-term safety studies have been completed with no concerns for further development.

HETEROARYL COMPOUNDS AS 5-HT4 RECEPTOR LIGANDS

The present invention relates to novel compounds of formula (I), and their pharmaceutically acceptable salts and compositions containing them. The present invention also relates to a process for the preparation of above said novel compounds, and their pharmaceutically acceptable salts. The compounds of formula (I) are useful in the treatment of various disorders that are related to 5-HT4 receptors.

Crystalline form of an indazole-carboxamide compound

The invention provides crystalline halide salts of 1-isopropyl-1H-indazole-3-carboxylic acid {(1S,3R,5R)-8-[2-(4-acetylpiperazin-1-yl)ethyl]-8-azabicyclo[3.2.1]oct-3-yl}amide and solvates thereof. The invention also provides pharmaceutical compositions comprising such salts, methods of using such crystalline salts to treat diseases associated with 5-HT4 receptor activity, and processes useful for preparing such crystalline salts.