581812-76-2

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
1H-Indazole-1-carboxylic acid, 4-amino-, methyl ester (9CI) is utilized as a key building block in the synthesis of various pharmaceutical compounds for its structural properties and potential to contribute to the development of new medications. Its role in this application is to provide a foundation for the creation of molecules with specific therapeutic effects, enhancing the diversity of available treatments.
Used in the Synthesis of Bioactive Molecules:
In the field of medicinal chemistry, 1H-Indazole-1-carboxylic acid, 4-amino-, methyl ester (9CI) serves as a starting material for the production of new bioactive molecules. Its unique structure allows for the design and synthesis of compounds with potential applications in treating various diseases and conditions, thereby expanding the range of therapeutic options.
Note: Since the provided materials do not specify particular industries or detailed applications beyond the general areas of pharmaceutical research and drug development, the uses listed are broad and pertain to these overarching fields. Further information would be required to delineate specific applications within particular industries or for more targeted uses.

Upstream product

• 2942-40-7 nitro-4 indazole 
• 603-83-8 3-nitro-o-tolylamine 
• 581812-75-1 4-nitroindazole-1-carboxylic acid methyl ester 

Downstream Products

• 581812-77-3 4-[3-(3,4-dichlorobenzyl)ureido]indazole-1-carboxylic acid methyl ester 
• 735331-29-0 N-1H-indazol-4-yl-N'-(3-phenylpropyl)urea 
• 1254716-40-9 methyl 4-(phenoxycarbonylamino)-1H-indazole-1-carboxylate 
• 946388-31-4 1-(2-benzyl-4-(8-azabicyclo[3.2.1]octan-8-yl)benzyl)-3-(1H-indazol-4-yl)urea 

Relevant academic research and scientific papers

SUBSTITUTED AROMATIC CARBOXAMIDE AND UREA DERIVATIVES AS VANILLOID RECEPTOR LIGANDS

The invention relates to substituted aromatic carboxamide and urea derivatives, to processes for the preparation thereof, to pharmaceutical compositions containing these compounds and also to the use of these compounds for preparing pharmaceutical compositions (formula (I)).

TRPV1 ANTAGONISTS

Disclosed herein are compounds of Formula (I), or pharmaceutically acceptable salts, solvates, prodrugs, salts of prodrugs, or combinations thereof, wherein R1, R2, R3, R4, and m are defined in the specification. Compositions comprising such compounds and methods for treating conditions and disorders using such compounds and compositions are also disclosed.

TRPV1 ANTAGONISTS

Disclosed herein are compounds of formula (I), or pharmaceutically acceptable salts, solvates, prodrugs, salts of prodrugs, or combinations thereof, wherein R1, R2, R3, R4, and m are defined in the specification. Compositions comprising such compounds and methods for treating conditions and disorders using such compounds and compositions are also disclosed.

Identification of (R)-1-(5-tert-butyl-2,3-dihydro-1H-inden-1-yl)-3-(1H- indazol-4-yl)urea (ABT-102) as a potent TRPV1 antagonist for pain management

Vanilloid receptor TRPV1 is a cation channel that can be activated by a wide range of noxious stimuli, including capsaicin, acid, and heat. Blockade of TRPV1 activation by selective antagonists is under investigation by several pharmaceutical companies in an effort to identify novel agents for pain management. Here we report that replacement of substituted benzyl groups by an indan rigid moiety in a previously described N-indazole-N′-benzyl urea series led to a number of TRPV1 antagonists with significantly increased in vitro potency and enhanced drug-like properties. Extensive evaluation of pharmacological, pharmacokinetic, and toxicological properties of synthesized analogs resulted in identification of (R)-7 (ABT-102). Both the analgesic activity and drug-like properties of (R)-7 support its advancement into clinical pain trials.

α-Methylation at benzylic fragment of N-aryl-N′-benzyl ureas provides TRPV1 antagonists with better pharmacokinetic properties and higher efficacy in inflammatory pain model

SAR studies for N-aryl-N′-benzyl urea class of TRPV1 antagonists have been extended to cover α-benzyl alkylation. Alkylated compounds showed weaker in vitro potencies in blocking capsaicin activation of TRPV1 receptor, but possessed improved pharmacokinetic properties. Further structural manipulations that included replacement of isoquinoline core with indazole and isolation of single enantiomer led to TRPV1 antagonists like (R)-16a with superior pharmacokinetic properties and greater potency in animal model of inflammatory pain.

Antagonists of the Vanilloid Receptor Subtype 1 (VR1) and Uses Thereof

The present invention is directed to compounds of formula (I) wherein variables X1, X2, Y, R1a, R1b, R2a, R2b, A1, A2, A3, and A4 are as defined

Prodrugs of compounds that inhibit TRPV1 receptor

Compounds of formula (I) wherein A, R1, R2, and R3 are defined in the specification, and which are useful as therapeutic compounds particularly for treating disorders or conditions associated with inflammation, pain, bladd

Structure-activity studies of a novel series of 5,6-fused heteroaromatic ureas as TRPV1 antagonists

Novel 5,6-fused heteroaromatic ureas were synthesized and evaluated for their activity as TRPV1 antagonists. It was found that 4-aminoindoles and indazoles are the preferential cores for the attachment of ureas. Bulky electron-withdrawing groups in the para-position of the aromatic ring of the urea substituents imparted the best in vitro potency at TRPV1. The most potent derivatives were assessed in in vivo inflammatory and neuropathic pain models. Compound 46, containing the indazole core and a 3,4-dichlorophenyl group appended to it via a urea linker, demonstrated in vivo analgesic activity upon oral administration. This derivative also showed selectivity versus other receptors in the CEREP screen and exhibited acceptable cardiovascular safety at levels exceeding the therapeutic dose.

Chromanylurea compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor and uses thereof

Compounds that are antagonists of the VR1 receptor, having formula (I) [image] or a pharmaceutically acceptable salt, prodrug, or salt of a prodrug thereof, wherein A1, A2, A3, A4, R7, R8, R9, X, Y, Z, L, n, and m, are as defined herein, and are useful in disorders prevented or ameliorated by inhibiting the VR1 receptor.

Fused azabicyclic compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor

Compounds of formula (I) are novel VR1 antagonists that are useful in treating pain, inflammatory thermal hyperalgesia, urinary incontinence and bladder overactivity, wherein X1, X2, X3, X4, X5, R5, R6, R7, R8a, R8b, R9, Z1, Z2 and L are as defined in the description.