Piclozotan

Base Information

• Chemical Name: Piclozotan
• CAS No.: 182415-09-4
• Molecular Formula: C₂₃H₂₄ClN₃O₂
• Molecular Weight: 409.915
• UNII: FQE44HS7AH
• DSSTox Substance ID: DTXSID90870153
• Nikkaji Number: J1.509.059F
• Wikipedia: Piclozotan
• Wikidata: Q7190969
• NCI Thesaurus Code: C90944
• Metabolomics Workbench ID: 153361
• ChEMBL ID: CHEMBL345237
• Mol file: 182415-09-4.mol

Synonyms:3-chloro-4-(4-(4-(2-pyridinyl)-1,2,3,6-tetrahydropyridin-1-yl)butyl)-1,4-benzoxazepin-5(4H)-one;Piclozotan;SUN N4057

Chemical Property of Piclozotan

Chemical Property:

• PSA: 45.67000
• LogP: 4.39920
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 409.1557047
• Heavy Atom Count: 29
• Complexity: 636

Purity/Quality:

97% ^*data from raw suppliers

PiclozotanDihydrochlorideLabeledd8 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CC=C1C2=CC=CC=N2)CCCCN3C(=COC4=CC=CC=C4C3=O)Cl
• Recent ClinicalTrials: Preliminary Study of Piclozotan in Patients With Motor Complications Associated With Parkinson's Disease
• Recent EU Clinical Trials: A Phase IIb Randomized, Double-Blind, Placebo-Controlled, Group-Sequential, Multicenter, Dose Finding Study of the Safety and Efficacy of SUN N4057 (Piclozotan)Administered for 72 Hours by Continuous Intravenous Infusion in Subjects with Acute Ischemic Stroke and Measurable Penumbra on MRI.

Technology Process of Piclozotan

There total 9 articles about Piclozotan 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: 97.0%

3-chloro-4-[4-[4-(2-pyridinyl)pyridinio-1-yl]butyl]-1,4-benzoxazepin-5(4H)-one iodide → Piclozotan (182415-09-4)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 20 ℃; for 0.166667h;

DOI:10.1016/j.bmc.2005.10.046

Reference yield: 84.0%

4-(pyridin-2-yl)-1,2,3,6-tetrahydropyridine (50461-51-3) + 3-Chloro-4-(4-Chlorobutyl)-4,5-Dihydro-1,4-Benzoxazepin-5-One (182415-82-3) → Piclozotan (182415-09-4)

Guidance literature:

With triethylamine; sodium iodide;

DOI:10.1016/S0960-894X(01)00008-7

Reference yield: 81.0%

3-chloro-4,5-dihydro-4-(4-(4-(pyridin-2-yl)pyridinio-1-yl)butyl)-1,4-benzoxazepin-5-one chloride → Piclozotan (182415-09-4)

Guidance literature:

With sodium borohydrid; In ethanol; water; ethyl acetate;

upstream raw materials:

4-(pyridin-2-yl)-1,2,3,6-tetrahydropyridine

3-Chloro-4-(4-Chlorobutyl)-4,5-Dihydro-1,4-Benzoxazepin-5-One

2,3,4,5-tetrahydro-1,4-benzoxazepine-3,5-dione

2-(ethoxycarbonylmethyloxy)benzamide

Refernces

• 1、 Kamei, Katsuhide,Maeda, Noriko,Nomura, Kayoko,Shibata, Makoto,Katsuragi-Ogino, Ryoko,Koyama, Makoto,Nakajima, Mika,Inoue, Teruyoshi,Ohno, Tomochika,Tatsuoka, Toshio. "Synthesis, SAR studies, and evaluation of 1,4-benzoxazepine derivatives as selective 5-HT1A receptor agonists with neuroprotective effect: Discovery of Piclozotan". . p. 1978 - 1992. Retrieved 2007/10/03.
• 2、 -. "Benzoxazepine derivatives and their salts and medicaments containing the same". . . Retrieved 2008/06/13.