Aleglitazar

Base Information

• Chemical Name: Aleglitazar
• CAS No.: 475479-34-6
• Molecular Formula: C24H23NO5S
• Molecular Weight: 437.516
• UNII: 41T4OAG59U
• DSSTox Substance ID: DTXSID70197193
• Wikipedia: Aleglitazar
• Wikidata: Q3609417
• NCI Thesaurus Code: C72687
• Pharos Ligand ID: 95U9DZRMC66K
• Metabolomics Workbench ID: 152000
• ChEMBL ID: CHEMBL519504
• Mol file: 475479-34-6.mol

Synonyms:aleglitazar

Chemical Property of Aleglitazar

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 146-147 °C
• Refractive Index: 1.627
• Boiling Point: 665.151 °C at 760 mmHg
• PKA: 3.54±0.46(Predicted)
• Flash Point: 356.071 °C
• PSA: 110.03000
• Density: 1.291 g/cm³
• LogP: 5.12830
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 437.12969401
• Heavy Atom Count: 31
• Complexity: 586

Purity/Quality:

98%Min ^*data from raw suppliers

Aleglitazar ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(N=C(O1)C2=CC=CC=C2)CCOC3=C4C=CSC4=C(C=C3)CC(C(=O)O)OC
• Isomeric SMILES: CC1=C(N=C(O1)C2=CC=CC=C2)CCOC3=C4C=CSC4=C(C=C3)C[C@@H](C(=O)O)OC
• Recent ClinicalTrials: A Study of Aleglitazar in Combination With Metformin in Patients With Type 2 Diabetes Mellitus Who Are Inadequately Controlled With Metformin Alone
• Recent EU Clinical Trials: A Phase 3b Study To Evaluate The Potential Of Aleglitazar To Reduce Cardiovascular Risk In Patients With Stable Cardiovascular Disease And Glucose Abnormalities
• Use Description: Aleglitazar is a pharmaceutical compound developed for its potential applications in the medical field, specifically in the treatment of cardiovascular diseases and diabetes. In the field of medicine, it has been studied for its role as a dual peroxisome proliferator-activated receptor (PPAR) agonist, which means it can simultaneously activate two types of PPAR receptors—PPAR-alpha and PPAR-gamma. This dual activation can have beneficial effects on lipid metabolism, insulin sensitivity, and glucose regulation, making it a candidate for the management of conditions like type 2 diabetes and dyslipidemia. However, it's important to note that as of my last knowledge update in September 2021, aleglitazar had faced challenges in clinical development due to safety concerns, particularly related to cardiovascular events. Therefore, its exact role and usage in the medical field were still under evaluation and required further research and regulatory approval. Please consult more recent sources for the latest information on aleglitazar's status and applications in the medical field.

Technology Process of Aleglitazar

There total 6 articles about Aleglitazar 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%

(Z)-2-methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-acrylic acid (849150-55-6) → [14C]-Aleglitazar (475479-34-6) + (2R)-2-methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionic acid (849150-59-0)

Guidance literature:

With sodium hydroxide; hydrogen; Ru(OAc)2((S)-(6-MeO-2-naphthyl)-MeOBIPHEP); In methanol; dichloromethane; water; at 40 ℃; for 24h; under 11251.1 Torr; Product distribution / selectivity;

Reference yield: 70.0%

(Z)-2-methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-acrylic acid (849150-55-6) → [14C]-Aleglitazar (475479-34-6)

Guidance literature:

With hydrogen; [Ir((S,S)-DBT-Bn-SIPHOX)(COD)]BARF; (S)-1-phenyl-ethylamine; In tetrahydrofuran; methanol; at 60 - 80 ℃; for 10h; under 22502.3 Torr; Product distribution / selectivity;

Reference yield:

2-methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionic acid (475479-24-4) → [14C]-Aleglitazar (475479-34-6)

Guidance literature:

2-methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionic acid; With (S)-1-phenyl-ethylamine; In tetrahydrofuran; Reflux;

With hydrogenchloride; In water; ethyl acetate; at 20 ℃; for 1h;

upstream raw materials:

(Z)-2-methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-acrylic acid

(S)-4-benzyl-3-((S)-2-methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionyl)-oxazolidin-2-one

2-methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionic acid

Downstream raw materials:

diisopropylammonium (S)-2-methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propanoate

(S)-2-methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionic acid L-norephedrine salt

(S)-2-methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionic acid (S)-phenyl ethylamine salt

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF PROPIONIC ACID DERIVATIVES". Page/Page column 25-26. . Retrieved 2011/06/26.
• 2、 Benardeau, Agnes,Benz, Joerg,Binggeli, Alfred,Blum, Denise,Boehringer, Markus,Grether, Uwe,Hilpert, Hans,Kuhn, Bernd,Maerki, Hans Peter,Meyer, Markus,Puentener, Kurt,Raab, Susanne,Ruf, Armin,Schlatter, Daniel,Mohr, Peter. "Aleglitazar, a new, potent, and balanced dual PPARα/γ agonist for the treatment of type II diabetes". experimental part. p. 2468 - 2473. Retrieved 2010/03/24.