183232-62-4

Basic information

• Product Name: 5-(4-CHLOROPHENYL)-1-(2,4-DICHLOROPHENYL)-4-METHYLPYRAZOLE-3-CARBOXYLICACID
• Synonyms: 1-(2,4-Dichlorophenyl)-4-methyl-5-(4-bromophenyl)-1H-pyrazole-3-carboxylicacid ethyl ester;5-(4-Bromophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic acidethyl ester; Ethyl5-(4-Bromophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylate
• CAS NO: 183232-62-4
• Molecular Formula: C₁₉H₁₅BrCl₂N₂O₂
• Molecular Weight: 381.64
• Mol File: 183232-62-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-(4-CHLOROPHENYL)-1-(2,4-DICHLOROPHENYL)-4-METHYLPYRAZOLE-3-CARBOXYLICACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-CHLOROPHENYL)-1-(2,4-DICHLOROPHENYL)-4-METHYLPYRAZOLE-3-CARBOXYLICACID(183232-62-4)
• EPA Substance Registry System: 5-(4-CHLOROPHENYL)-1-(2,4-DICHLOROPHENYL)-4-METHYLPYRAZOLE-3-CARBOXYLICACID(183232-62-4)

Safety Data

• Hazardous Substances Data: 183232-62-4(Hazardous Substances Data)

Upstream product

• 13123-92-7 (2,4-dichlorophenyl)hydrazine 
• 850554-39-1 ethyl 2,4-dioxo-3-methyl-4-(4-bromophenyl)butanoate lithium salt 
• 10342-83-3 4'-Bromopropiophenone 
• 5446-18-4 2,4-dichlorophenyl hydrazine hydrochloride 
• 95-92-1 oxalic acid diethyl ester 
• 64-17-5 ethanol 
• 5467-74-3 4-Bromophenylboronic acid 
• 1166390-93-7 ethyl 4-(4-bromophenyl)-3-methyl-2,4-dioxobutanoate 
• 288104-75-6 4-(4-bromo-phenyl)-2-[(2,4-dichloro-phenyl)-hydrazono]-3-methyl-4-oxo-butyric acid ethyl ester 

Downstream Products

• 288104-76-7 ethyl 4-(bromomethyl)-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxylate 
• 1245626-05-4 AM 6545 
• 183232-66-8 1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-(1-piperidinyl)-1H-pyrazole-3-carboxamide 
• 183232-63-5 1-(2,4-dichlorophenyl)-5-(4-bromophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide 
• 183232-64-6 5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic chloride 
• 850554-41-5 1-(2,4-dichloro-phenyl)-4-methyl-5-{4-[5-(tetrahydro-pyran-2-yloxy)-pentyl]-phenyl}-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide 
• 850554-43-7 methanesulfonic acid 5-{4-[2-(2,4-dichloro-phenyl)-4-methyl-5-(piperidin-1-ylcarbamoyl)-2H-pyrazol-3-yl]-phenyl}-pentyl ester 
• 850554-42-6 N-(piperidin-1-yl)-1-(2,4-dichlorophenyl)-5-{4-(5-hydroxypentyl)phenyl}-4-methyl-1H-pyrazole-3-carboxamide 

Relevant articles and documents

Process for Making Biologically Active Compounds and Intermediates Thereof

A process of manufacturing biologically active compounds, their analogs, pharmaceutically acceptable salts, solvates, polymorphs, isotopic variants, and intermediates thereof. Notably, the compounds of the formula IA, 1B, 1C. 1D. 1E, 1F and IG for which novel processes have been disclosed, selectively act on the cannabinoid receptors, and with high affinity. The processes for the preparation of the compounds enable the syntheses of cannabinoid modulators on a large-scale that are eco-friendly and economically viable. Additionally, the processes disclosed enable the synthesis of cannabinoid modulators with high purity and in high yield for their use in making drug substance and drug products.

Compounds for Treating Cannabinoid Toxicity and Acute Cannabinoid Overdose

The present invention relates to novel compounds that can act as antidotes for treating “Acute Cannabinoid Overdose” produced by classical cannabinoids such as Δ9-tetrahydrocannabinol (THC) and several synthetic psychoactive cannabinoids (SPCs). The cannabis constituent THC exerts its psychotropic effects via CB1 receptor activation and SPCs mimic the effects of THC with higher potency and severe neurotoxicity. Compounds disclosed in this invention, their enantiomers, diastereomers, geometric isomers, racemates, tautomers, rotamers, atropisomers, metabolites, N-oxides, salts, solvates, hydrates, isotopic variations and their polymorphic forms can be therapeutically useful in an emergency setting for counteracting the intoxicating effects of acute THC ingestion and SPC overdose. Also, aspects of the invention are concerned with pyrazoles, imidazoles, triazoles, thiazoles, oxazoles, dihydropyrazoles, pyrrolidinones, azetidines, oxyazetidines and azaspiro[3.3]heptanes with unique pharmacokinetic and pharmacodynamic properties for treating “Acute Cannabinoid Overdose”.

Divalent cannabinoid-1 receptor ligands: A linker attachment point survey of SR141716A for development of high-affinity CB1R molecular probes

The cannabinoid-1 receptor (CB1R) inverse agonist SR141716A has proven useful for study of the endocannabinoid system, including development of divalent CB1R ligands possessing a second functional motif attached via a linker unit. These have predominantly employed the C3 position of the central pyrazole ring for linker attachment. Despite this precedent, a novel series of C3-linked CB1R-D2R divalent ligands exhibited extremely high affinity at the D2R, but only poor affinity for the CB1R. A systematic linker attachment point survey of the SR141716A pharmacophore was therefore undertaken, establishing the C5 position as the optimal site for linker conjugation. This linker attachment survey enabled the identification of a novel divalent ligand as a lead compound to inform ongoing development of high-affinity CB1R molecular probes.

"One-poto" synthesis of 4-substituted 1,5-diaryl-1H-pyrazole-3- carboxylic acids via a MeONa/LiCl-mediated sterically hindered claisen condensation-Knorr reaction-hydrolysis sequence

A "one-poto" synthesis of 4-substituted 1,5-diaryl-1H-pyrazole-3- carboxylic acids was first reported in moderate to good yields. This concise procedure, featuring efficiency and green chemistry, was composed of MeONa/LiCl-mediated sterically hindered Claisen condensation, Knorr reaction and hydrolysis. Georg Thieme Verlag KG · Stuttgart · New York.

Imidazol-4-one and Imidazole-4-thione Compounds

Imidazol-4-one or imidazole-4-thione compounds of formula (I): wherein X, R1, R2, R3, R4, R5, and R6 are defined herein. Also disclosed is a method for treating a cannabinoid receptor-mediated disorder with these compounds.

Discovery of 2-[5-(4-chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-ethyl-1H- pyrazol-3-yl]-1,5,5-trimethyl-1,5-dihydro-imidazol-4-thione (BPR-890) via an active metabolite. A novel, potent and selective cannabinoid-1 receptor inverse agonist with high antiobes

By using the active metabolite 5 as an initial template, further structural modifications led to the identification of the titled compound 24 (BPR-890) as a highly potent CB1 inverse agonist possessing an excellent CB2/1 selectivity and remarkable in vivo

A method for parallel solid-phase synthesis of Lodinated analogues of the CB1 receptor inverse agonist rimonabant

A method for the parallel solid-phase synthesis (SPS) of iodinated analogues of Sanofi-Aventis' type 1 cannabinoid (CB1) receptor Inverse agonist rimonabant (acomplia) has been developed. The method allows the synthesis of a range of C3 amide/hydrazide derivatives from a resin-bound C3 ester precursor. The C-Ge linkage to the Hypogel-200 resin Is stable to the diversification conditions but allows ipsoiododegermylative cleavage using Nal/NCS even for the products containing the oxidatively labile hydrazide moiety.

Derivatives of N′-(1,5-diphenyl-1H-pyrazol-3-yl) sulfonamide with CB1 receptor affinity

The invention relates to compounds of formula (I): Wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 are as defined herein. The invention also relates to the prepa

NOVEL HETEROPYRROLE ANALOGS ACTING ON CANNABINIOD RECEPTORS

Disclosed are biologically active hetero pyrrole analogs such as imidazoles, thiazoles, oxazoles and pyrazoles capable of interacting with the CB1 and/or the CB2 cannabinoid receptors. One aspect discloses hetero pyrrole analogs acting as antagonists for

Synthesis of novel 5-substituted pyrazole derivatives as cannabinoid antagonists

A facile seven-step sequence was developed from 4′- bromopropiophenone, utilizing a Suzuki-type coupling with an alkene, to give several novel 5-substituted pyrazole derivatives in overall yields of 11-31%. They are potent CB1 antagonists and have binding