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

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

Uses

Used in Pharmaceutical Research and Development:
1-Isopropylindazole-3-carboxylic acid is used as a key building block in the synthesis of new drugs and pharmaceuticals. Its unique structure and properties make it a promising candidate for the development of innovative therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, 1-Isopropylindazole-3-carboxylic acid is utilized as a valuable intermediate for the preparation of various organic compounds. Its reactivity and functional groups enable the formation of diverse chemical entities.
Used in Chemical Research:
1-Isopropylindazole-3-carboxylic acid is employed in chemical research to explore its properties, reactivity, and potential applications. It serves as a model compound for studying the behavior of carboxylic acid derivatives in various chemical reactions.
Used in the Production of Specialty Chemicals:
1-ISOPROPYLINDAZOLE-3-CARBOXYLIC ACID is also used in the manufacturing process of specialty chemicals, where its unique structure and properties contribute to the development of high-value products for specific applications.

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.

Sulfocoumarin-, Coumarin-, 4-Sulfamoylphenyl-Bearing Indazole-3-carboxamide Hybrids: Synthesis and Selective Inhibition of Tumor-Associated Carbonic Anhydrase Isozymes IX and XII

A series of sulfocoumarin-, coumarin-, and 4-sulfamoylphenyl-bearing indazole-3-carboxamide hybrids were synthesized and investigated as inhibitors of the human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms I and II (cytosolic isozymes), as well as hCA IX and XII (transmembrane, tumor-associated enzymes). Compounds 6 a–g (amide derivatives) and 7 a–h (triazoles) act as “prodrugs”, and their hydrolysis products are the de facto CA inhibitors. These compounds displayed sub-micromolar to high-nanomolar inhibitory activity against hCA isoforms IX and XII, which were recently validated as antitumor drug targets. Moreover, no inhibition of the off-target hCA I and II isoforms was observed. Compounds 8 a–f (another set of triazoles) exhibited nanomolar inhibition against hCA isoforms I, II, IX and XII, among which compounds 8 c, 8 d, and 8 f were found to inhibit the tumor-associated hypoxia-induced hCA isoform IX with Ki values of 1.8, 2.3, and 2.0 nm respectively. Further exploration of these compounds could be useful for the development of novel antitumor agents with selective mechanisms of CA inhibitory action.

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.

Indazole-carboxamide compounds

The invention provides novel indazole-carboxamide 5-HT4 receptor agonist compounds. The invention also provides pharmaceutical compositions comprising such compounds, methods of using such compounds to treat diseases associated with 5-HT4 receptor activity, and processes and intermediates useful for preparing such compounds.

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.

INDAZOLE-CARBOXAMIDE COMPOUNDS AS 5-HT4 RECEPTOR AGONISTS

The invention provides novel indazole-carboxamide 5-HT4 receptor agonist compounds. The invention also provides pharmaceutical compositions comprising such compounds, methods of using such compounds to treat diseases associated with 5-HT4 receptor activity, and processes and intermediates useful for preparing such compounds.

5-HT4 agonists and antagonists

Compounds of formula I: are used as antagonists and partial agonists for the serotonin receptor 5-HT4 and provide therapeutic methods for treatment of disorders caused by or affected by dysfunction of the 5-HT4 receptor.

Indazole derivatives having monocyclic amine

An indazole compound having the formula (I): wherein: R1 is hydrogen, C1 -C6 alkyl, C3 -C6 alkenyl or C3 -C6 cycloalkyl; Q is carbonyl, thiocarbonyl or methylene; and R2 is a group of the formula (II) or (IV); STR1 wherein R1 is C1 -C6 alkyl, C3 -C6 alkenyl or benzyl, of which a phenyl group thereof is optionally mono- or di-substituted by the same or different halogen or methoxy; m is 0 to 2; n and o is 1 or 2. The compound exhibits 5-HT4 receptor agonist activity.

Development of potent serotonin-3 (5-HT3) receptor antagonists. II. Structure-activity relationships of N-(1-benzyl-4-methylhexahydro-1H-1,4- diazepin-6-yl)carboxamides

Our studies on 4-amino-5-chloro-2-ethoxybenzamides led to the discovery that the N-(1,4-dimethylhexahydro-1H-1,4-diazepin-6-yl)benzamide 9 and the 1- benzyl-4-methylhexahydro-1H-1,4-diazepine analogue 10 are potent serotonin-3 (5-HT3) receptor antagonists. Structure-activity relationship (SAR) studies on the influence of the aromatic nucleus of 9 and 10 upon inhibition of the von Bezold-Jarisch reflex in rats are described. Heteroaromatic rings such as pyrrole, thiophene, furan, pyridine, pyridaziae, 1,2-benzisoxazole, indole, quinoline, and isoquinoline rings showed weak 5-HT3 receptor antagonistic activity. Within this series, use of the 1H-indazole ring as an aromatic moiety led to a substantial increase of the activity; the 1H- indazolylcarboxamides 54, 57, 97, and 102 showed potent 5-HT3 receptor antagonistic activity. The optimal compound identified via extensive SAR studies was N-(1-benzyl-4-methylhexahydro-1H-1,4-diazepin-6-yl)-1H-indazole- 3-carboxamide (54), whose effect was superior to that of the corresponding benzamide 10 and essentially equipotent to those of ondansetron (1) and granisetron (4).