162758-35-2

Usage

Uses

Used in Pharmaceutical Industry:
5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic acid is used as a key intermediate in the synthesis of biarylpyrazole-based derivatives. These derivatives are known to act as cannabinoid CB1 receptor antagonists, which have potential applications in the development of antiobesity medications.
Specifically, 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic acid is identified as metabolite M9 of Rimonabant (R517800), an antiobesity agent. Rimonabant has been shown to help in weight management by targeting the endocannabinoid system, which is involved in regulating appetite and energy balance.

InChI:InChI=1/C17H11Cl3N2O2/c1-9-15(17(23)24)21-22(14-7-6-12(19)8-13(14)20)16(9)10-2-4-11(18)5-3-10/h2-8H,1H3,(H,23,24)

Upstream product

• 877-37-2 2-bromo-1-(4-chlorophenyl)-1-propanone 
• 2213-43-6 1-Aminopiperidine 
• 158941-22-1 ethyl 1-(2,4-dichlorophenyl)-4-methyl-5-(4-chlorophenyl)-1H-pyrazole-3-carboxylate 
• 168272-78-4 5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid methyl ester 
• 6285-05-8 4'-chloropropiophenone 
• 5446-18-4 2,4-dichlorophenyl hydrazine hydrochloride 
• 1012314-40-7 ethyl 4-(4-chlorophenyl)-3-methyl-4-oxydo-2-oxobuten-3-oate lithium salt 
• 95-92-1 oxalic acid diethyl ester 
• 13123-92-7 (2,4-dichlorophenyl)hydrazine 
• 170937-37-8 4-(4-chlorophenyl)-2-[(2,4-dichlorophenyl)-hydrazono]-3-methyl-4-oxobutyric acid ethyl ester 
• 944154-78-3 C₁₉H₁₈Cl₃N₂O₃^(1-)*Li⁽¹⁺⁾ 
• 192702-54-8 5-(4-chloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester 
• 1193-72-2 1-bromo-2,4-dichlorobenzene 
• 68716-47-2 2,4-dichlorophenylboronic acid 

Downstream Products

• 1159835-97-8 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(phenylsulfonyl)-1H-pyrazole-3-carboxamide 
• 1159836-00-6 5-(4-chlorophenyl)-N-(4-chlorophenylsulfonyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1159836-17-5 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-(isopropylsulfonyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1159836-18-6 N-(butylsulfonyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1159836-14-2 N-(benzylsulfonyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1159836-09-5 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-(3-fluorophenylsulfonyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1159836-03-9 5-(4-chlorophenyl)-N-(3-chlorophenylsulfonyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1159836-06-2 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-(4-fluorophenylsulfonyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1159836-12-0 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-ntosyl-1H-pyrazole-3-carboxamide 
• 1331784-11-2 N-(2-(2H-tetrazol-5-yl)propan-2-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1332262-52-8 (Z)-N-(1-amino-1-(hydroxyimino)-2-methylpropan-2-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1332262-54-0 C₂₂H₂₂Cl₃N₅O₂ 
• 1332262-56-2 C₂₁H₁₈Cl₃N₅O₂ 
• 1332262-58-4 C₂₂H₂₀Cl₃N₅O₂ 

Relevant academic research and scientific papers

An improved synthesis of rimonabant: Anti-obesity drug

A novel, cost-effective, and efficient process was developed for the large-scale synthesis of Rimonabant 1, an anti-obesity drug. The process involves the conversion of 4-chloro propiophenone 2 to cyclized acid 6 as a key intermediate that afforded Rimonabant 1 in good yield.

Synthesis of 3-substituted pyrazole derivatives by mixed anhydride method and study of their antibacterial activities

A convenient synthesis of 3-substituted pyrazole derivatives by a mixed anhydride method using i-butylchloroformate and N-methylmorpholine at-20 °C in tetrahydrofuran and study of in vitro antibacterial activities of the prepared compounds against Staphyl

Novel 1,5-diaryl pyrazole-3-carboxamides as selective COX-2/sEH inhibitors with analgesic, anti-inflammatory, and lower cardiotoxicity effects

COX-2 selective drugs have been withdrawn from the market due to cardiovascular side effects, just a few years after their discovery. As a result, a new series of 1,5-diaryl pyrazole carboxamides 19–31 was synthesized as selective COX-2/sEH inhibitors wit

MMPL3 INHIBITORS, COMPOSITIONS AND USES THEREOF

Disclosed are inhibitors of mycobacterial membrane protein MmpL3, compositions comprising the inhibitors, and methods of preparation and use thereof.

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.

Preparation method for rimonabant hydrochloride

The invention discloses a preparation method for rimonabant hydrochloride, belonging to the field of chemical pharmacy. An ester is used as an initial raw material and undergoes hydrolysis, condensation and salt formation so as to obtain the rimonabant hydrochloride. The preparation method is simple and convenient to operate and has low cost and high yield.

SUBSTITUTED PYRAZOLE COMPOUNDS AS CB1 RECEPTOR ANTAGONISTS AND USES THEREOF

The present invention relates to compounds of formula 1, or isotopic forms, stereoisomers, tautomers, pharmaceutically acceptable salts, solvates, polymorphs, prodrugs, S-oxides or N-oxides thereof, and processes for their preparation. The invention furth

1,5-Diarylpyrazole and vanillin hybrids: Synthesis, biological activity and DFT studies

Herein, we report the design and synthesis of 13 diarylpyrazole hybrids with vanillin constructed as dual compounds against oxidative stress and diabetes. Compounds were tested in two different antioxidant assays. It was found that all compounds showed an

Discovery of rimonabant and its potential analogues as anti-TB drug candidates

Rimonabant and its analogues have been synthesized in moderate to good yields using a simple synthetic route. All the newly synthesized compounds were subjected to in vitro screening against M. tuberculosis and M. smegmatis. The most potent analogue JMG-14 exhibits MIC value of 3.13 compared to 3.25 and 50 μ/ml for ethambutol and pyrazinamide, respectively. The molecular docking reveals that pyrazole ring, number and position of halogen atoms play a crucial role in deciding interactions with MTCYP-121. These findings open up a new avenue in the search of potent anti-TB drugs with rimonabant and its novel analogue JMG-14 as lead molecules.

The pentafluorosulfanyl group in cannabinoid receptor ligands: Synthesis and comparison with trifluoromethyl and tert-butyl analogues

An array of cannabinoid ligands, bearing meta- and para-substituted pentafluorosulfanyl (SF5) aniline groups in position 3 of the pyrazole ring, was efficiently synthesised and compared with the exact trifluoromethyl and tert-butyl analogues. In general, the SF5 substituted ligands showed higher lipophilicity (i.e. logP values) than the CF3 counterparts and lower lipophilicity than the tert-butyl ones. In terms of pharmacological activity, SF5 pyrazoles generally showed slightly higher or equivalent CB1 receptor affinity (Ki), always in the nanomolar range, and selectivity towards the CB2 relative to both CF3 and tert-butyl analogues. Functional β-arrestin recruitment assays were used to determine equilibrium dissociation constants (Kb) and showed that all of the tested SF 5 and CF3 compounds are CB1 neutral antagonists. These results confirm the possibility of successfully using an aromatic SF5 group as a stable, synthetically accessible and effective bioisosteric analogue of the electron-withdrawing CF3 group, and possibly also of bulky aliphatic groups, for drug discovery and development applications. This journal is the Partner Organisations 2014.