Elinogrel

Base Information

• Chemical Name: Elinogrel
• CAS No.: 936500-94-6
• Molecular Formula: C₂₀H₁₅ClFN₅O₅S₂
• Molecular Weight: 523.953
• UNII: 915Y8E749J
• ChEMBL ID: CHEMBL2103828
• DSSTox Substance ID: DTXSID50918262
• Metabolomics Workbench ID: 149747
• NCI Thesaurus Code: C96896
• Nikkaji Number: J2.991.489C
• Pharos Ligand ID: NMCGDBKZSGYL
• Wikidata: Q15408411
• Wikipedia: Elinogrel
• Mol file: 936500-94-6.mol

Synonyms:elinogrel;PRT 060128;PRT-060128;PRT060128

Chemical Property of Elinogrel

Chemical Property:

• PSA: 182.53000
• Density: 1.651 g/cm³
• LogP: 4.92860
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 523.0187168
• Heavy Atom Count: 34
• Complexity: 914

Purity/Quality:

99% ^*data from raw suppliers

Elinogrel ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC1=C(C=C2C(=C1)NC(=O)N(C2=O)C3=CC=C(C=C3)NC(=O)NS(=O)(=O)C4=CC=C(S4)Cl)F
• Recent ClinicalTrials: A Phase 2 Safety and Efficacy Study of PRT060128, a Novel Intravenous and Oral P2Y12 Inhibitor, in Non-Urgent PCI
• Recent EU Clinical Trials: A Randomized, Double-Blind, Active-Controlled Trial to Evaluate Intravenous and Oral PRT060128, a Selective and Reversible P2Y12-Receptor Inhibitor, vs. Clopidogrel, as a Novel Antiplatelet Therapy in Patients Undergoing Non-Urgent Percutaneous Coronary Interventions (INNOVATE-PCI)
• Description: Elinogrel is a reversible antagonist of the platelet purinergic P2Y12 receptor (Ki = 23 nM) that inhibits platelet aggregation in a human platelet-rich plasma (hPRP) assay (IC50 = 2.81 nM). It inhibits thrombosis in a mouse model of vascular injury induced by iron (III) chloride (FeCl3) when administered at a dose of 60 mg/kg.
• Uses: Elinogrel is a direct acting reversible P2Y12 inhibitor, which shows an antiplatelet effect and platelet reactivity associated with cytochrome P 450 2C19 and 3A5 gene polymorphisms.

Technology Process of Elinogrel

There total 8 articles about Elinogrel 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: 93.0%

(5-chloro-2-thienyl)sulfonylcarbamic acid ethyl ester (849793-87-9) + 3-(4-aminophenyl)-6-fluoro-7-(methylamino)quinazoline-2,4(1H,3H)-dione (936501-00-7) → Elinogrel (936500-94-6)

Guidance literature:

In dimethyl sulfoxide; at 65 ℃; for 15h; Product distribution / selectivity;

Reference yield: 92.0%

(5-chloro-2-thienyl)sulfonylcarbamic acid ethyl ester (849793-87-9) + 3-(4-aminophenyl)-6-fluoro-7-(methylamino)quinazoline-2,4(1H,3H)-dione → Elinogrel (936500-94-6)

Guidance literature:

In acetonitrile; for 36h; Product distribution / selectivity; Heating / reflux;

Reference yield:

2-amino-4,5-difluoro-benzoic acid,methyl ester (207346-42-7) → Elinogrel (936500-94-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dichloromethane / 3 h / 40 °C

2.1: triethylamine / tetrahydrofuran / 0.42 h

2.2: 2 h / 65 °C

3.1: methanol; sodium methylate / tetrahydrofuran / 4.33 h / 25 - 30 °C

4.1: hydrogenchloride / 1,4-dioxane / 5 - 6 h / 20 - 30 °C

5.1: ethanol; dimethyl sulfoxide / 5.67 h / 25 - 110 °C

6.1: dimethyl sulfoxide / 15 h / 65 °C

With hydrogenchloride; methanol; sodium methylate; triethylamine; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; dimethyl sulfoxide;

upstream raw materials:

(5-chloro-2-thienyl)sulfonylcarbamic acid ethyl ester

3-(4-aminophenyl)-6-fluoro-7-(methylamino)quinazoline-2,4(1H,3H)-dione

C₁₅H₁₀F₂N₂O₆

C₁₉H₁₇F₂N₃O₄

Refernces

• 1、 -. "SUBSTITUTED-(QUINAZOLINYL)PHENYL THIOPHENYL-SULFONYLUREAS, METHODS FOR MAKING AND INTERMEDIATES THEREOF". Page/Page column 43-44. . Retrieved 2010/11/27.