Drinabant

Base Information

• Chemical Name: Drinabant
• CAS No.: 358970-97-5
• Molecular Formula: C₂₃H₂₀Cl₂F₂N₂O₂S
• Molecular Weight: 497.393
• UNII: 61S98RLL5I
• DSSTox Substance ID: DTXSID50189455
• Wikipedia: Drinabant
• Wikidata: Q5307675
• NCI Thesaurus Code: C166890
• ChEMBL ID: CHEMBL3545166
• Mol file: 358970-97-5.mol

Synonyms:AVE1625

Chemical Property of Drinabant

Chemical Property:

• Boiling Point: 581.7±60.0 °C(Predicted)
• PKA: 5.44±0.10(Predicted)
• PSA: 49.00000
• Density: 1.458
• LogP: 6.53010
• Solubility.: ≤0.15mg/ml in ethanol;15mg/ml in DMSO;15mg/ml in dimethyl formamide
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 496.0590608
• Heavy Atom Count: 32
• Complexity: 686

Purity/Quality:

98%Min ^*data from raw suppliers

AVE-1625 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CS(=O)(=O)N(C1CN(C1)C(C2=CC=C(C=C2)Cl)C3=CC=C(C=C3)Cl)C4=CC(=CC(=C4)F)F
• Recent ClinicalTrials: Efficacy and Safety of AVE1625 as a Co-treatment With Antipsychotic Therapy in Schizophrenia
• Recent EU Clinical Trials: A double-blind placebo-controlled study of the activity of AVE1625 at doses of 10 mg and 40mg for 12 weeks in patients with mild to moderate Alzheimer's Disease
• Description: The central cannabinoid (CB1) receptor is a G protein-coupled receptor that is widely distributed in the central nervous system and several peripheral tissues and binds the active component of cannabis, Δ9-tetrahydrocannabinol. Signaling through the CB1 receptor is implicated in attentional and working memory deficits as well as obesity. AVE-1625 is a highly potent, selective antagonist for the CB1 receptor with Ki values of 0.16-0.44 nM. At 1-3 mg/kg, AVE-1625 significantly improves the performance of rodents in working memory tasks. At 30 mg/kg, AVE-1625 reduces caloric intake by more than 50% of controls and significantly increases lipolysis from fat tissues and reduces hepatic glycogen levels in rodents.
• Uses: AVE-1625 is a selective antagonist for the CB1 receptor.

Technology Process of Drinabant

There total 3 articles about Drinabant which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.2%

1-[bis(4-chlorophenyl)methyl]azetidin-3-yl methanesulphonate (358971-49-0) + N-(3,5-difluorophenyl)methanesulfonamide (358971-48-9) → Drinabant (358970-97-5)

Guidance literature:

With potassium phosphate; Tris(3,6-dioxaheptyl)amine; In dichloromethane; at 112 ℃; for 20h; Heating / reflux;

Reference yield: 68.0%

N-(3,5-difluorophenyl)methanesulfonamide (358971-48-9) + 1-[bis(4-chlorophenyl)methyl]azetidin-3-ol hydrobromide → Drinabant (358970-97-5)

Guidance literature:

1-[bis(4-chlorophenyl)methyl]azetidin-3-ol hydrobromide; With sodium hydroxide; In water; toluene; at 45 ℃; for 1h;

N-(3,5-difluorophenyl)methanesulfonamide; With di-isopropyl azodicarboxylate; triphenylphosphine; In isopropyl alcohol; toluene; at 36 - 90 ℃; for 2.5h;

Reference yield:

N-(3,5-difluorophenyl)methanesulfonamide (358971-48-9) + 1-[bis(4-chlorophenyl)methyl]-azetidin-3-ol (261924-66-7) → Drinabant (358970-97-5)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 16h; Product distribution / selectivity;

upstream raw materials:

1-[bis(4-chlorophenyl)methyl]azetidin-3-yl methanesulphonate

N-(3,5-difluorophenyl)methanesulfonamide

1-[bis(4-chlorophenyl)methyl]-azetidin-3-ol

Refernces

• 1、 -. "METHOD AND INTERMEDIATES FOR THE PREPARATION OF DERIVATIVES OF N (1-BENZHYDRYLAZETIDIN-3-YL)-N-PHENYLMETHYLSULFONAMIDE". Page/Page column 7. . Retrieved 2008/06/13.