869891-96-3

Upstream product

• 1013649-25-6 5-(5-bromothiophen-2-yl)-1-(2,4-dichloro-phenyl)-4-methyl-5-thiophen-2-yl-1H-pyrazole-3-carboxylic acid ethyl ester 
• 13679-75-9 1-thiophen-2-yl-propan-1-one 
• 1013649-23-4 1-(2,4-dichloro-phenyl)-4-methyl-5-thiophen-2-yl-1H-pyrazole-3-carboxylic acid ethyl ester 

Downstream Products

• 869891-72-5 5-(5-bromothiophen-2-yl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide 
• 1627941-81-4 5-(5-bromothiophen-2-yl)-1-(2,4-dichlorophenyl)-4-methyl-N-(4-(pentafluoro-λ⁶-sulfanyl)phenyl)-1H-pyrazole-3-carboxamide 
• 1627941-80-3 5-(5-bromothiophen-2-yl)-1-(2,4-dichlorophenyl)-4-methyl-N-(4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carboxamide 
• 1627941-78-9 5-(5-bromothiophen-2-yl)-1-(2,4-dichlorophenyl)-4-methyl-N-(3-(pentafluoro-λ⁶-sulfanyl)phenyl)-1H-pyrazole-3-carboxamide 
• 1627941-77-8 5-(5-bromothiophen-2-yl)-1-(2,4-dichlorophenyl)-4-methyl-N-(3-(trifluoromethyl)phenyl)-1H-pyrazole-3-carboxamide 
• 1020100-71-3 5-(5-bromothiophen-2-yl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonyl chloride 
• 1627941-82-5 5-(5-bromothiophen-2-yl)-N-(4-(tert-butyl)phenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 

Relevant academic research and scientific papers

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.

Hair growth stimulator property of thienyl substituted pyrazole carboxamide derivatives as a cb1 receptor antagonist with in vivo antiobesity effect

A few thienyl substituted pyrazole derivatives were synthesized to aid in the characterization of the cannabinoid receptor antagonist and also to serve as potentially useful antiobesity agent. Structural requirements for selective CB1 receptor antagonistic activity of 5-thienyl pyrazole derivatives included the structural similarity with potent, specific antagonist rimonabant 1. Compound 3 has been identified as a hair growth stimulator and an antiobesity agent in animal models.

Bioisosteric replacement of the pyrazole 5-aryl moiety of N-(piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H- pyrazole-3-carboxamide (SR141716A). A novel series of alkynylthiophenes as potent and selective cannabinoid-1 receptor anta

Replacing the conventional pyrazole 5-aryl substituent of 1 (SR141716A) with the 2-thienyl moiety appended with an appropriate alkynyl unit, a novel class of 5-(5-alkynyl-2-thienyl)pyrazole derivatives, behaving as highly potent CB1 receptor antagonists w

PYRAZOLE COMPOUNDS

This invention relates to pyrazole compounds of formula (I) shown below: Each variable in formula (I) is defined in the specification. These compounds can be used to treat cannabinoid-receptor mediated disorders.

Oxadiazole Compounds

A compound of formula (I): in which A, R1, R2, and R3 are as defined herein. Also disclosed are (1) a pharmaceutical composition containing such a compound, and (2) a method for treating a cannabinoid receptor-mediated dis