168273-06-1 Usage
Description
Different sources of media describe the Description of 168273-06-1 differently. You can refer to the following data:
1. Rimonabant is an inverse antagonist for the cannabinoid receptor (CB1). It acts by selectively blocking CB1 receptors found in the brain and in peripheral organs important in glucose and lipid metabolism, including adipose tissue, the liver, gastrointestinal tract, and muscle. Thus, rimonabant constitutes a therapeutic approach to obesity and cardiovascular risk factors. As an anorectic antiobesity drug, it was used as an adjunct to diet and exercise for obese or overweight patients with associated risk factors in Europe in 2006. Nevertheless, adverse effects including suicidality, depression, and anxiety were reported, based on which rimonadant was withdrawn worldwide in 2008.
Andogenous cannabinoids are related to the pleasurable effect of nicotine, rimonabant, as a cannabinoid receptor blocker, is also being tested as a potential anti-smoking treatment.
2. Rimonabant is a first-in-class drug launched as an oral treatment
for obesity, and its mechanism of action involves the selective antagonism
of cannabinoid type 1 (CB1) receptor. It is specifically indicated as an adjunct
to diet and exercise for the treatment of obese patients (body mass index
[BMI]≥30 kg/m2), or overweight patients (BMI＞27 kg/m2) with associated risk
factors such as type 2 diabetes or dyslipidemia. Additionally, rimonabant is
currently under development as a treatment for nicotine dependence. The CB1
and CB2 receptors, along with their endogenous ligands, constitute the endocannabinoid
system. The CB1 receptor is expressed in the brain, adipose tissue,
and several peripheral organs; the CB2 receptor is predominantly expressed in
immune cells. Activation of the CB1 receptor in the CNS is associated with
appetite stimulation and the modulation of brain reward mechanism, whereas
activation in the periphery favors metabolic processes that lead to hepatic lipogenesis
and impaired glucose homeostasis. Rimonabant acts by selectively
blocking the action of central and peripheral CB1 receptors, thereby reducing
food intake and improving lipid and glucose metabolism.
References
Different sources of media describe the References of 168273-06-1 differently. You can refer to the following data:
1. [1] https://www.drugs.com/acomplia.html
[2] Leite CE, Mocelin CA, Petersen GO, Leal MB, Thiesen FV (2009) Rimonabant: an antagonist drug of the endocannabinoid system for the treatment of obesity, Pharmacol Rep., 61, 217-224
2. 1) Rinaldi-Carmona et al. (1994) SR141716A, a potent and selective antagonist of the brain cannabinoid receptor; FEBS Lett. 350 240
2) Rinaldi-Carmona et al. (1995) Biochemical and pharmacological characterization of SR141716A, the first potent and selective cannabinoid receptor antagonist; Life Sci. 56 1941
Uses
Rimonabant is a selective antagonist of CB1 with IC50 of 13.6 nM and EC50 of 17.3 nM in hCB1 transfected HEK 293 membrane
Brand name
Acomplia (Sanofi-Synthe-labo).
Synthesis
The reported preparation of rimonabant,
both in small and large scale, is shown in the scheme. Lithium enolate formation of p-chlorophenyl ethyl ketone 54 with LiHMDS in THF at -78oC for 45 min followed
by reaction with diethyl oxalate at -78oC and warming
to room temperature over 16 h provided the lithium enolate
salt of the diketoester 55. Reaction of diketoester salt 55 with
2,4-dichlorophenyl hydrazine (56) in ethanol at room temperature
gave intermediate hydrazone 57 which is then cyclized
in refluxing acetic acid for 24 h to obtain pyrazole
ester 58. Hydrolysis of ester 58 with KOH in refluxing
methanol:water mixture gave acid 59 which was then converted
to the acid chloride 60 with thionyl chloride in refluxing
toluene in very good yield. On scale, the synthesis of the
acid chloride was performed in cyclohexane at 83oC. Reaction
of acid chloride 60 with 1-aminopiperidine (61) in the
presence of triethylamine at 0oC to room temperature over 3h
gave rimonabant (VIII) which was isolated as the HCl salt
by treating it with HCl in ether.
Check Digit Verification of cas no
The CAS Registry Mumber 168273-06-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,6,8,2,7 and 3 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 168273-06:
(8*1)+(7*6)+(6*8)+(5*2)+(4*7)+(3*3)+(2*0)+(1*6)=151
151 % 10 = 1
So 168273-06-1 is a valid CAS Registry Number.
InChI:InChI=1/C22H21Cl3N4O/c1-14-20(22(30)27-28-11-3-2-4-12-28)26-29(19-10-9-17(24)13-18(19)25)21(14)15-5-7-16(23)8-6-15/h5-10,13H,2-4,11-12H2,1H3,(H,27,30)
168273-06-1Relevant articles and documents
Process for Making Biologically Active Compounds and Intermediates Thereof
-
, (2022/02/05)
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.
PYRAZOLE CARBOXYLIC ACID ANALOGUES AS ANTI-MYCOBACTERIAL DRUG CANDIDATES
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Page/Page column 14; 15, (2014/11/13)
The present invention relates to the pyrazole carboxylic acid analogues of Formula (1) or stereoisomers, or esters or pharmaceutically acceptable salts thereof, as potent anti- mycobacterial agents. Formula Further it discloses the pharmaceutical composition comprising compounds of Formula-I for the treatment of mycobacterial infections.
PROCESS FOR PREPARING FORM I OF RIMONABANT
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Page/Page column 6, (2010/01/12)
The present invention describes new process for the preparation of Form I of Rimonabant through the intermediate formation of the corresponding acid addition salt.
