220461-68-7

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-4-(3-Methyl-1H-pyrazol-1-yl)benzoic acid is utilized as an intermediate in the synthesis of various pharmaceuticals. Its unique structure, which includes a chloro and pyrazole group, allows for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Chloro-4-(3-Methyl-1H-pyrazol-1-yl)benzoic acid serves as a key intermediate in the production of agrochemicals. Its incorporation into these compounds can contribute to the creation of effective pesticides or other agricultural products designed to protect crops and enhance yield.
Used as a Building Block in Organic Chemistry:
2-Chloro-4-(3-Methyl-1H-pyrazol-1-yl)benzoic acid is also employed as a building block in the synthesis of diverse organic compounds. Its presence in these compounds can lead to the development of new materials with unique properties and applications across various industries.

Upstream product

• 85953-29-3 methyl 2-chloro-4-fluorobenzoate 
• 220461-67-6 2-chloro-4-(3-methyl-1H-pyrazol-1-yl)benzamide 
• 21900-54-9 2-chloro-4-fluorobenzoyl chloride 
• 220462-02-2 2-chloro-4-(3-methylpyrazol-1-yl)benzoic acid methyl ester 

Downstream Products

• 220460-92-4 VNA-932 
• 220602-55-1 [2-chloro-4-(3-methyl-1H-pyrazol-1-yl)-phenyl]-(6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-6-yl)-methanone 
• 1209963-38-1 5-[2-chloro-4-(3-methyl-1H-pyrazol-1-yl)benzoyl]-1-methyl-1,4,5,10-tetrahydro pyrazolo[3,4-b][1,5]benzodiazepine 
• 1143023-20-4 2-chloro-N-[(6-{[3-(4-methylpiperazin-1-yl)propyl]sulfonyl}-1,3-benzothiazol-2-yl)carbamoyl]-4-(3-methyl-1H-pyrazol-1-yl)benzamide 
• 220461-67-6 2-chloro-4-(3-methyl-1H-pyrazol-1-yl)benzamide 
• 233755-70-9 2-chloro-4-(3-methyl-1H-pyrazol-1-yl)benzoyl chloride 

Relevant academic research and scientific papers

LIT-001, the First Nonpeptide Oxytocin Receptor Agonist that Improves Social Interaction in a Mouse Model of Autism

Oxytocin (OT) and its receptor (OT-R) are implicated in the etiology of autism spectrum disorders (ASD), and OT-R is a potential target for therapeutic intervention. Very few nonpeptide oxytocin agonists have currently been reported. Their molecular and in vivo pharmacology remain to be clarified, and none of them has been shown to be efficient in improving social interaction in animal models relevant to ASD. In an attempt to rationalize the design of centrally active nonpeptide full agonists, we studied in a systematic way the structural determinants of the affinity and efficacy of representative ligands of the V1a and V2 vasopressin receptor subtypes (V1a-R and V2-R) and of the oxytocin receptor. Our results confirm the subtlety of the structure-affinity and structure-efficacy relationships around vasopressin/oxytocin receptor ligands and lead however to the first nonpeptide OT receptor agonist active in a mouse model of ASD after peripheral ip administration.

Subtlety of the Structure-Affinity and Structure-Efficacy Relationships around a Nonpeptide Oxytocin Receptor Agonist

Very few nonpeptide oxytocin agonists have currently been reported, and none of them seem suitable for the in vivo investigation of the oxytocin mediated functions. In an attempt to rationalize the design of better tools, we have systematically studied the structural determinants of the affinity and efficacy of representative ligands of the V1a, V2, and OT receptor subtypes. Despite apparently obvious similarity between the ligand structures on one hand, and between the receptor subtypes on the other hand, the binding affinity and the functional activity profiles of truncated and hybrid ligands highlight the subtlety of ligand-receptor interactions for obtaining nonpeptide OT receptor agonists.

Synthesis and structure-activity relationships of amide derivatives of (4,4-difluoro-1,2,3,4-tetrahydro-5H-1-benzazepin-5-ylidene)acetic acid as selective arginine vasopressin V2 receptor agonists

A series of (4,4-difluoro-1,2,3,4-tetrahydro-5H-1-benzazepin-5-ylidene)acetamide derivatives was synthesized, and their structure-activity relationships were examined in order to identify potent and selective arginine vasopressin V2 receptor agonists. Attempts to substitute other chemical groups in place of the 2-pyridilmethyl moiety of 1a led to the discovery that potent V2 binding affinity could be obtained with a wide range of functional groups. This structural tolerance allowed for the manipulation of other attributes, such as selectivity against V1a receptor affinity or avoidance of the undesirable inhibition of cytochrome P450 (CYP), without losing potent affinity for the V2 receptor. Some representative compounds obtained in this study were also found to decrease urine volume in awake rats.

Optimization of (4,4-difluoro-1,2,3,4-tetrahydro-5H-1-benzazepine-5-ylidene)acetamide derivatives as arginine vasopressin V2 receptor agonists and discussion of their binding modes

A series of (4,4-difluoro-1,2,3,4-tetrahydro-5H-1-benzazepine-5-ylidene)acetamide derivatives were optimized to achieve potent agonistic activity, both in vitro and in vivo, for the arginine vasopressin V2 receptor, resulting in the eventual di

Preparation of (4,4-difluoro-1,2,3,4-tetrahydro-5H-1-benzazepin-5-ylidene)acetamide derivatives as novel arginine vasopressin V2 receptor agonists

The present work describes the discovery of novel series of (4,4-difluoro-1,2,3,4-tetrahydro-5H-1-benzazepine-5-ylidene)acetamide derivatives as arginine vasopressin (AVP) V2 receptor agonists. By replacing the amide juncture in YM-35278 with a direct ring connection gave compound 10a, which acts as a V2 receptor agonist. These studies provided the potent, orally active non-peptidic V2 receptor agonists 10a and 10j.

Identification and synthesis of major metabolites of Vasopressin V2-receptor agonist WAY-151932, and antagonist, Lixivaptan

Small molecule agonists and antagonists of the V2-vasopressin receptor have been discovered and have undergone clinical trials. In conjunction with these discovery programs, the synthesis and biological testing of various metabolites associated with these clinical targets were actively pursued. We now report the results of our synthetic efforts and the corresponding biological data generated for several of the metabolites of WAY-151932 and CL-347985 (Lixivaptan).

TRICYCLIC VASOPRESSIN AGONISTS

The present invention provides compounds of general formula (I): wherein W is O or NH, optionally substituted, as well as methods and pharmaceutical compositions utilising these compounds for the treatment of disorder which may be remedied or alleviated by vasopressin agonist activity, including diabetes insipidus, nocturnal enuresis, nocturia, urinary incontinence, bleeding and coagulation disorders, or temporary delay of urination.

4,4-DIFLUORO-1,2,3,4-TETRAHYDRO-5H-1-BENZAZEPINE DERIVATIVES OR SALTS THEREOF

4,4-difluoro-1,2,3,4-tetrahydro-5H-1-benzazepine derivatives, which have excellent arginine vasopressin V2 activity and are useful for a drug for the treatment of central diabetes insipidus and/or nocturia.

Vasopressin agonist formulation and process

This invention provides novel formulations for vasopressin agonist compounds, or a pharmaceutically acceptable salt thereof, having the general structure: and processes for making them, the formulations comprising from about 1% to about 20% of active ingredient, from about 1% to about 18% of a surfactant component, from about 50% to about 80% of a component of one or more polyethylene glycols, from about 1% to about 20% of a component of one or more sucrose fatty acid esters and/or polyvinylpyrrolidone and, optionally, one or more preservatives or antioxidants.