ChemicalBook CAS DataBase List 168273-06-1

168273-06-1

Name	Rimonabant
CAS	168273-06-1
EINECS(EC#)	200-223-5
Molecular Formula	C22H21Cl3N4O
MDL Number	MFCD04034714
Molecular Weight	463.79
MOL File	168273-06-1.mol

Chemical Properties

Melting point	154.7 °C
density	1.41±0.1 g/cm3(Predicted)
storage temp.	RT
solubility	Soluble in DMSO (up to 20 mg/ml) or in Ethanol (up to 20 mg/ml).
form	solid
pka	11.31±0.20(Predicted)
color	White
Stability:	Stable for 1 year from date of purchase as supplied. Protect from moisture. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
InChI	InChI=1S/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)
InChIKey	JZCPYUJPEARBJL-UHFFFAOYSA-N
SMILES	N1(C2=CC=C(Cl)C=C2Cl)C(C2=CC=C(Cl)C=C2)=C(C)C(C(NN2CCCCC2)=O)=N1
CAS DataBase Reference	168273-06-1(CAS DataBase Reference)

Hazard Information

Originator

Sanofi-Synthelabo (France)

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

Definition

ChEBI: Rimonabant is a carbohydrazide obtained by formal condensation of the carboxy group of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid with the amino group of 1-aminopiperidine. It is a potent and selective cannabinoid receptor 1 (CB1R) antagonist. Besides its antagonistic properties, numerous studies have shown that, at micromolar concentrations rimonabant behaves as an inverse agonist at CB1 receptors. The drug was the first selective CB1 antagonist/inverse agonist introduced into clinical practice to treat obesity and metabolic-related disorders. It was later withdrawn from market due to CNS-related adverse effects including depression and suicidal ideation. It has a role as an anti-obesity agent, a CB1 receptor antagonist and an appetite depressant. It is a member of pyrazoles, a dichlorobenzene, a carbohydrazide, an amidopiperidine and a member of monochlorobenzenes.

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.

Synthesis_168273-06-1

Questions And Answer

Spectrum Detail

Supplier

Guangzhou Dihao Medical Technology Co., Ltd

Telephone 18602015453

Websitehttps://www.chemicalbook.com/ShowSupplierProductsList1341519/0_EN.htm

Chengdu Kaitaichuang Pharmaceutical Technology Co., Ltd

Telephone 16608035117

Website

Baoji Didu Pharmaceutical and Chemical Co., Ltd

Telephone029-029-81148929 17791530722

Websitehttps://www.dideu.com

Guangzhou Hongyin Biotechnology Co., Ltd

Telephone 13779362612

Website

Chembest Research Laboratories Limited

Telephone+86-21-20908456

Websitehttp://www.BioChemBest.com

ShangHai DEMO Chemical Co.,Ltd

Telephone400-021-7337 2355568890

Websitehttp://www.demochem.com

Beijing HwrkChemical Technology Co., Ltd

Telephone18515581800 18501085097

Websitehttp://www.hwrkchemical.com

Jia Xing Isenchem Co.,Ltd

Telephone0573-85285100 18627885956

Websitehttps://www.chemicalbook.com/ShowSupplierProductsList14265/0_EN.htm

Shanghai Longsheng chemical Co.,Ltd.

Telephone021-58099652-8005 13585536065

Websitehttp://www.shlschem.com

Hangzhou Yuhao Chemical Technology Co., Ltd

Telephone0571-82693216

Websitehttp://www.chemyuhao.com

Beijing Yisiyan Technology Research Center

Telephone010-56645598 13366904824

Websitehttp://www.bjkaida.cn

Shanghai T&W Pharmaceutical Co., Ltd.

Telephone+86 21 61551611

Websitehttp://www.trustwe.com

Nanjing Norris-Pharm Technology Co., Ltd

Telephone 18652989687

Website

9ding chemical ( Shanghai) Limited

Telephone4009209199

Websitehttp://www.9dingchem.com

Shanghai Aladdin Bio-Chem Technology Co.,LTD

Telephone400-6206333 13167063860

Websitehttp://www.aladdin-e.com/

Nanjing Dulai Biotechnology Co., Ltd.

Telephone025-846993838003-8003 18013301590

Websitehttp://www.njduly.com

Guangzhou Isun Pharmaceutical Co., Ltd

Telephone020-39119399 18927568969

Websitehttp://www.isunpharm.com

Nanjing Sunlida Biological Technology Co., Ltd.

Telephone025-57798810

Websitehttp://www.sunlidabio.com

1of4

Related Products

Send Inquriy

168273-06-1

Chemical Properties

Hazard Information

Originator

Uses

Definition

Brand name

Synthesis

Questions And Answer

Description

References

Spectrum Detail

Supplier

Related Products