168272-91-1

Upstream product

• 158941-22-1 ethyl 1-(2,4-dichlorophenyl)-4-methyl-5-(4-chlorophenyl)-1H-pyrazole-3-carboxylate 

Downstream Products

• 1174985-54-6 1-((5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl)methyl)piperidine 
• 917081-45-9 5-(4-chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-hydroxymethyl-1H-pyrazole-3-carboxylic acid cyclohexylamide 
• 1429241-60-0 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-(piperidin-1-yl)-4-((pyrrolidine-1-sulfonamido)methyl)-1H-pyrazole-3-carboxamide 
• 1429242-21-6 4-(aminomethyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide 
• 1016557-50-8 ethyl 4-((1H-1,2,4-triazol-1-yl)-methyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxylate 

Relevant academic research and scientific papers

Repurposing of a drug scaffold: Identification of novel sila analogues of rimonabant as potent antitubercular agents

The structural similarity between an MmpL3 inhibitor BM212, and a cannabinoid receptor modulator rimonabant, prompted us to investigate the anti-tubercular activity of rimonabant and its analogues. Further optimization, particularly through incorporation of silicon into the scaffold, resulted in new compounds with significant improvement in anti-tubercular activity against Mycobacterium tuberculosis (H37Rv). The sila analogue 18a was found to be the most potent antimycobacterial compound (MIC, 31?ng/mL) from this series with an excellent selectivity index.

PYRAZOLE COMPOUNDS

Compounds of formula (I): wherein R1, R2, R3, R4, R5, and X are defined herein. Also disclosed are pharmaceutical compositions and methods related to use of these compounds.

Synthesis and structure-activity relationship of 1,2,4-triazole-containing diarylpyrazolyl carboxamide as CB1 cannabinoid receptor-ligand

Numerous research groups have been engaged in searching for novel CB1 receptor antagonists, since SR141716A (rimonabant), a CB1 receptor antagonist, proved to be efficacious in human for the treatment of obesity. In the present study, a series of 1,2,4-triazole-containing diarylpyrazolyl carboxamides based on the 1,5-diarylpyrazole template of rimonabant, was synthesized and tested for CB1 receptor binding affinity. The structure-activity relationship studies demonstrated that incorporation of 1,2,4-triazole ring onto the pyrazole scaffold via a methylene linker led to a significant improvement for CB1 receptor binding affinity. Importantly, these analogues also exhibited excellent selectivity for CB1 receptor over CB2 receptor.

Discovery of 2-(4-((1H-1,2,4-triazol-1-yl)methyl)-5-(4-bromophenyl)-1-(2- chlorophenyl)-1H-pyrazol-3-yl)-5-tert-butyl-1,3,4-thiadiazole (GCC2680) as a potent, selective and orally efficacious cannabinoid-1 receptor antagonist

Structure-activity relationship studies in a series of diarylpyrazolyl thiadiazoles identified cannabinoid-1 receptor antagonists with excellent potency and selectivity. Based on its exceptional in vivo efficacy in animal models and its favorable pharmaco

Oxadiazole-diarylpyrazole 4-carboxamides as cannabinoid CB1 receptor ligands

Cannabinoid CB-1 receptors have been the focus of extensive studies since the first clinical results of rimonabant (SR141716) for the treatment of obesity and obesity-related metabolic disorders were reported in 2001. To further evaluate the properties of

Pentacycle derivatives as cannabinoid CB1 receptor ligands

Cannabinoid CB-1 receptors have been the focus of extensive studies since the first clinical results of rimonabant (SR141716) for the treatment of obesity and obesity-related metabolic disorders were reported in 2001. To further evaluate the properties of

FUSED PYRAZOLE DERIVATIVES AS CANNABINOID RECEPTOR MODULATORS

The present invention relates to novel cannabinoid receptor modulators of formula (I), in particular cannabinoid 1 (CB1) or cannabinoid 2 (CB2) receptor modulators, and uses thereof for treating diseases, conditions and/or disorders modulated by a cannabi

Biarylpyrazolyl oxadiazole as potent, selective, orally bioavailable cannabinoid-1 receptor antagonists for the treatment of obesity

Since the CB1 cannabinoid receptor antagonist 1 (SR141716, rimonabant) was previously reported to modulate food intake, CB1 antagonism has been considered as a new therapeutic target for the treatment of obesity. In the present study, biarylpyrazole analo

PYRAZOLE DERIVATES AS CANNABINOID RECEPTOR MODULATORS

Compounds of formula (I), are cannabinoid CB1 receptors, useful, inter alia in the treatment of obesity: (I) wherein A1 is hydrogen, -COOH, or tetrazolyl, and A2 is hydrogen, -COOH, tetrazolyl, -CN, -CF3, -COR6, -SO2R6, -OR7, -NR7R8, -NHCOR6, and -NR7SO2R8 provided that one of A1 and A2 is either -COOH or tetrazolyl; p is O or 1 and A3 is phenyl or cycloalkyl, either of which is optionally substituted with R4 and/or R5; q is O or 1 ; R1 is a bond, or - (CH2)aB1(CH2)b- wherein a and b are independently O, 1 , 2 or 3 provided that a+b is not greater than 4, and B1 is -CO-, -0-, -S-, -SO-, -SO2-, -CH2-, -CHOH- or -NR7-; R2 is a bond, -(CH2)aB1 (CH2)b- or -[(CH2)aB1 (CH2)b]n-A4-[(CH2)cB2(CH2)d]m- wherein a, b, and B1 are as defined for R1; B2 is as defined for B1, c and d are independently 0,1 , 2 or 3; with the proviso that a+b+c+d is not greater than 6, n and m are independently O or 1 and A4 is a monocarbocyclic or monoheterocyclic ring, having 3 to 8 ring atoms, optionally substituted with one or more of -F, -Cl, -Br, -CN, -CF3, C1-C4 alkyl, cycloalkyl, -OR9, oxo or -NR7R8; R3 is hydrogen, C1-C4 alkyl, cycloalkyl, -CF3, -OR9, -NR7R8, -(CH2)SCOR6, -(CH2)SSO2R6, -(CH2)SNR7COR6, -(CH2)SNR7COOR8, -(CH2)SNR7SO2R6, wherein s is 1 , 2, 3 or 4; R4 and R5 independently -R9, -CN, -F, -Cl, -Br, -OR9, -NR7R8, -NR7COR6, -NR7SO2R6, -COR6, -SR9, -SOR9, -SO2R6, (C1-C4 alkyl)OR9, -(C1-C4 alkyl)NR7R8, -(C1-C4 alkyl)NR7COR6, C1-C4 alkyl)NR7COOR8, -(C1-C4 alkyl)NR7SO2R6, -(C1-C4 alkyl)COR6, -(C1-C4 alkyl)SO2R6, -NR7COOR8, or [N-(C1-C4 alkyl)]- tetrazolyl; R6 is C1-C4 alkyl, cycloalkyl, -CF3 or -NR7R8; R7 and R8 are independently hydrogen, C1-C4 alkyl or cycloalkyl and R9 is hydrogen, C1-C4 alkyl, cycloalkyl, fully or partially fluorinated C1-C4 alkyl.

Pyrazole derivatives, method for preparing same, and pharmaceutical compositions containing said derivatives

PCT No. PCT/FR96/01847 Sec. 371 Date May 19, 1998 Sec. 102(e) Date May 19, 1998 PCT Filed Nov. 21, 1996 PCT Pub. No. WO97/19063 PCT Pub. Date May 29, 1997Compounds of formula (I), wherein R1 is fluorine, hydroxy, (C1-5) alkoxy, (C1-5) alkylthio, hydroxy(C