173600-14-1

Basic information

• Product Name: 1-ISOPROPYLINDAZOLE-3-CARBOXYLIC ACID
• Synonyms: 1-ISOPROPYLINDAZOLE-3-CARBOXYLIC ACID;1-(propan-2-yl)-1H-indazole-3-carboxylic acid;1-Isopropyl-3-indazole carboxylic acid;1-isopropyl-1H-indazole-3-carboxylic acid
• CAS NO: 173600-14-1
• Molecular Formula: C₁₁H₁₂N₂O₂
• Molecular Weight: 204.23
• Mol File: 173600-14-1.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 378.287°C at 760 mmHg
• Flash Point: 182.582°C
• Appearance: /
• Density: 1.269g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.619
• CAS DataBase Reference: 1-ISOPROPYLINDAZOLE-3-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ISOPROPYLINDAZOLE-3-CARBOXYLIC ACID(173600-14-1)
• EPA Substance Registry System: 1-ISOPROPYLINDAZOLE-3-CARBOXYLIC ACID(173600-14-1)

Safety Data

• Hazardous Substances Data: 173600-14-1(Hazardous Substances Data)

Usage

General Description

1-Isopropylindazole-3-carboxylic acid is a chemical compound with the molecular formula C11H11N3O2. It is a carboxylic acid derivative of indazole, a nitrogen-containing heterocyclic compound. This chemical compound is used as a building block in organic synthesis and pharmaceutical research. It has potential applications in the development of new drugs and pharmaceuticals due to its unique structure and properties. Additionally, it may also be used in chemical research and in the production of specialty chemicals. Overall, 1-isopropylindazole-3-carboxylic acid is a versatile compound with various potential uses in the field of chemistry and pharmaceuticals.

InChI:InChI=1/C11H12N2O2/c1-7(2)13-9-6-4-3-5-8(9)10(12-13)11(14)15/h3-7H,1-2H3,(H,14,15)

Upstream product

• 4498-67-3 1H-Indazole-3-carboxylic acid 
• 75-26-3 isopropyl bromide 
• 75-30-9 2-iodo-propane 
• 43120-28-1 methyl 1H-indazole-3-carboxylate 
• 173600-05-0 methyl 1-isopropyl-1H-indazol-3-ylcarboxylate 

Downstream Products

• 173600-05-0 methyl 1-isopropyl-1H-indazol-3-ylcarboxylate 
• 1408237-71-7 N-(4-hydroxy-3,5-dimethylphenyl)-1'-iso-propyl-1H-indazol-3'-carboxyamide 
• 934302-39-3 C₁₉H₂₁N₅O₂S 
• 934302-38-2 C₁₉H₂₁N₅O₂S 
• 934302-41-7 C₁₉H₂₁N₅OS 
• 934302-43-9 C₁₈H₁₈ClN₅OS 
• 934302-40-6 C₁₉H₂₁N₅OS 
• 934302-37-1 C₁₉H₂₁N₅O₂S 
• 934302-42-8 C₁₉H₂₁N₅OS 
• 934302-36-0 C₁₈H₁₉N₅OS 

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.

PROCESS FOR LARGE SCALE PRODUCTION OF 1-ISOPROPYL-3-{5- [1-(3-METHOXYPROPYL) PIPERIDIN-4-YL]-[1,3,4]OXADIAZOL-2-YL}- 1H-INDAZOLE OXALATE

The present invention relates to a process suitable for adoption to large scale manufacture of l-IsopropyI-3-{5-[l1-(3-methoxypropyl) piperidin-4-yl]-[ 1,3,4] oxadiazol-2-yl}- 1H-indazole oxalate of formula (I), which is a selective 5-HT4 receptor ligand intended for the symptomatic treatment of Alzheimer's disease and other disorders of memory and cognition like Attention deficient hyperactivity, Parkinson's and Schizophrenia.

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.