Imidapril

Base Information

• Chemical Name: Imidapril
• CAS No.: 89371-37-9
• Molecular Formula: C20H27N3O6
• Molecular Weight: 405.451
• UNII: BW7H1TJS22
• DSSTox Substance ID: DTXSID2048242
• Nikkaji Number: J325.987K
• Wikipedia: Imidapril
• Wikidata: Q1041804
• NCI Thesaurus Code: C72908
• Pharos Ligand ID: PWQ33AXH5MFW
• Metabolomics Workbench ID: 49615
• ChEMBL ID: CHEMBL317094
• Mol file: 89371-37-9.mol

Synonyms:1-methyl-3-(2-(N-(1-ethoxycarbonyl-3-phenylpropyl)amino)propionyl)-2-oxoimidazolidine-4-carboxylic acid;4-imidazolidinecarboxylic acid, 3-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)-1-methyl-2-oxo-, monohydrochloride, (4S-(3(R*(R*)),4R*))-;imidapril;imidapril HCl;imidapril hydrochloride;TA 6366;TA-6366;Tanatril

Chemical Property of Imidapril

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 3.71E-14mmHg at 25°C
• Melting Point: 195-197 °C
• Boiling Point: 577 °C at 760 mmHg
• PKA: 2.44±0.20(Predicted)
• Flash Point: 302.8 °C
• PSA: 116.25000
• Density: 1.266 g/cm³
• LogP: 1.14290
• Storage Temp.: -20°C Freezer
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 10
• Exact Mass: 405.18998559
• Heavy Atom Count: 29
• Complexity: 619

Purity/Quality:

99%min ^*data from raw suppliers

ImidaprilHCl ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CCC1=CC=CC=C1)NC(C)C(=O)N2C(CN(C2=O)C)C(=O)O
• Isomeric SMILES: CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2[C@@H](CN(C2=O)C)C(=O)O
• Recent ClinicalTrials: Antiproteinuric Effect of Imidapril Versus Ramipril in Type 2 Diabetic and Hypertensive Patients With Microalbuminuria
• Recent EU Clinical Trials: A multi-centre, double-blind, randomised, placebo-controlled, phase IIa exploratory study of the effects of Imidapril on body weight and body composition in Non-Small Cell Lung Cancer patients with cancer cachexia.
• Recent NIPH Clinical Trials: Prospective, randomized, open-label,clinical trial comparing the effects of olmesartan and imidapril on blood pressure, endothelial function and makers for obesity/oxidative stress/chronic kidney diseases
• Description: Imidapril is a new ACE inhibitor launched in Japan as a once-daily therapy for hypertension. Its active metabolite has more potent inhibitory effects on all tissue ACES from spontaneously hypertensive rats (SHRs) and Wistar Kyoto rats (WKYs) than many other ACE inhibitors including enalapril and captopril. It has a very long duration of action. In strokeprone spontaneously hypertensive rats (SHRSP), imidapril is effective in stroke prevention at a considerably lower dose than enalapril. This stroke preventive effect has been suggested to be primarily by an indirect mechanism related to the amelioration of kidney dysfunction.
• Uses: Angiotensin converting enzyme (ACE) inhibitor. Antihypertensive

Technology Process of Imidapril

There total 4 articles about Imidapril 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: 91.9%

benzyl (4S)-1-methyl-3-{(2S)-2-[N-((1S)-1-ethoxycarbonyl-3-phenylpropyl)amino]propionyl}-2-oxoimidazolidine-4-carboxylate (89371-36-8) → imidapril (89371-37-9,120294-10-2)

Guidance literature:

palladium; In ethanol; hydrogen;

Reference yield: 68.1%

hydrogen chloride-dioxane + tert-butyl (4S)-1-methyl-3-{(2S)-2-[N-((1S)-1-ethoxycarbonyl-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylate (89371-38-0) → imidapril (89371-37-9,120294-10-2)

Guidance literature:

In ethyl acetate;

Reference yield:

tert-Butyl (4S)-3-<(2S)-2-amino>propionyl>-1-methyl-2-oxoimidazolidine-4-carboxylate Hydrogenmaleate (117605-23-9) → imidapril (89371-37-9,120294-10-2)

Guidance literature:

With potassium carbonate; In water; Yield given;

DOI:10.1248/cpb.39.1374

upstream raw materials:

tert-Butyl (4S)-3-<(2S)-2-amino>propionyl>-1-methyl-2-oxoimidazolidine-4-carboxylate Hydrogenmaleate

tert-butyl (4S)-1-methyl-3-{(2S)-2-[N-((1S)-1-ethoxycarbonyl-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylate

benzyl (4S)-1-methyl-3-{(2S)-2-[N-((1S)-1-ethoxycarbonyl-3-phenylpropyl)amino]propionyl}-2-oxoimidazolidine-4-carboxylate

Downstream raw materials:

ethanol

(4S)-1-methyl-3-{(2S)-2-[N-((1S)-1-carboxy-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylic acid

Refernces

• 1、 Kubota,Nunami,Yamagishi,Nishimoto,Hayashi. "Studies on angiotensin converting enzyme inhibitors. V. The diastereoselective synthesis of 2-oxoimidazolidine derivatives". . p. 1374 - 1377. Retrieved 2007/10/02.