Nelivaptan

Base Information

• Chemical Name: Nelivaptan
• CAS No.: 439687-69-1
• Molecular Formula: C30H32ClN3O8S
• Molecular Weight: 630.11
• European Community (EC) Number: 685-405-6
• UNII: 3TY57MQ4OA
• DSSTox Substance ID: DTXSID7047358
• Wikipedia: Nelivaptan
• Wikidata: Q6989992
• NCI Thesaurus Code: C132046
• Pharos Ligand ID: TB1GVQYVUW2B
• Metabolomics Workbench ID: 153593
• ChEMBL ID: CHEMBL582857
• Mol file: 439687-69-1.mol

Synonyms:1-(5-chloro-1-((2,4-dimethoxyphenyl)sulfonyl)-3-(2-methoxyphenyl)-2-oxo-2,3-dihydro-1H-indol-3-yl)-4-hydroxy-N,N-dimethyl-2-pyrrolidinecarboxamide;SSR 149415;SSR-149415;SSR149415

Chemical Property of Nelivaptan

Chemical Property:

• PSA: 134.30000
• LogP: 3.95200
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 8
• Exact Mass: 629.1598639
• Heavy Atom Count: 43
• Complexity: 1140

Purity/Quality:

99% ^*data from raw suppliers

SSR149415 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN(C)C(=O)C1CC(CN1C2(C3=C(C=CC(=C3)Cl)N(C2=O)S(=O)(=O)C4=C(C=C(C=C4)OC)OC)C5=CC=CC=C5OC)O
• Isomeric SMILES: CN(C)C(=O)[C@@H]1C[C@H](CN1[C@]2(C3=C(C=CC(=C3)Cl)N(C2=O)S(=O)(=O)C4=C(C=C(C=C4)OC)OC)C5=CC=CC=C5OC)O
• Recent ClinicalTrials: An Eight-week Study Evaluating the Efficacy and Tolerability of Two Doses of SSR149415 in Outpatients With Generalized Anxiety Disorder
• Recent EU Clinical Trials: A 14-week, multicentre, double-blind, randomised, placebo-controlled phase II study with an 8-week treatment period to assess the efficacy and tolerability of a fixed dose of BH-200 (250 mg BID) in outpatients with Major Depressive Disorder (MDD)
• Uses: SSR 149415 is a vasopressin V1b receptor antagonist.

Technology Process of Nelivaptan

There total 5 articles about Nelivaptan 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: 100.0%

C22H24ClN3O4 (352278-36-5) + 2,4-dimethoxybenzenesulfonylchloride (63624-28-2) → Nelivaptan (439687-69-1)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.05h;

DOI:10.1016/j.bmcl.2010.03.108

Reference yield:

C22H24ClN3O4 (352278-37-6) + 2,4-dimethoxybenzenesulfonylchloride (63624-28-2) → C30H32ClN3O8S (947602-61-1,439687-69-1)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃;

DOI:10.1016/j.bmcl.2010.03.108

Reference yield:

(2S,4R)-1-[5-Chloro-3-(2-methoxyphenyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-4-hydroxypyrrolidine-2-carboxylic acid dimethylamide (905077-26-1) + 2,4-dimethoxybenzenesulfonylchloride (63624-28-2) → Nelivaptan (439687-69-1) + C30H32ClN3O8S (947602-61-1,439687-69-1)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2011.03.012

upstream raw materials:

C₂₂H₂₄ClN₃O₄

2,4-dimethoxybenzenesulfonylchloride

(2S,4R)-1-[5-Chloro-3-(2-methoxyphenyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-4-hydroxypyrrolidine-2-carboxylic acid dimethylamide

C₂₂H₂₄ClN₃O₄

Refernces

Potent and selective oxindole-based vasopressin 1b receptor antagonists with improved pharmacokinetic properties

10.1016/j.bmcl.2011.03.012

This research details the discovery and optimization of a novel series of vasopressin 1b (V1b) receptor antagonists. The study begins with the potent but metabolically unstable oxindole SSR149415, known for its anxiolytic and anti-depressant effects in rodent models. The researchers aimed to enhance its metabolic stability and pharmacokinetic properties. They explored various strategies, including replacing phenyl rings with heteroaryl rings and introducing additional amine groups. Notably, masking the proline N,N-dimethyl amide moiety as an oxazole and attaching a benzylic amine moiety to the northern phenyl ring led to significant improvements. The optimized compound, 18c, demonstrated high potency, selectivity for the V1b receptor, and enhanced metabolic stability in both human and rat liver microsomes. It also showed good oral bioavailability, a long terminal half-life, and the ability to penetrate the blood-brain barrier. In a rat model of anti-depressant activity, 18c exhibited efficacy, suggesting its potential as a novel treatment for depression and anxiety disorders.

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 439687-69-1 (2S,4R)-1-[(R)-5-CHLORO-1-(2,4-DIMETHOXY-BENZENESULFONYL)-3-(2-METHOXY-PHENYL)-2-OXO-2,3-DIHYDRO-1H-INDOL-3-YL]-4-HYDROXY-PYRROLIDINE-2-CARBOXYLIC ACID DIMETHYLAMIDE

Send

Send

Metric Ton KG G Pound L ML

Send

Send