Quinapril

Base Information

• Chemical Name: Quinapril
• CAS No.: 85441-61-8
• Molecular Formula: C25H30N2O5
• Molecular Weight: 438.524
• UNII: RJ84Y44811
• DSSTox Substance ID: DTXSID4023547
• Nikkaji Number: J39.673G
• Wikipedia: Quinapril
• Wikidata: Q596022
• NCI Thesaurus Code: C62074
• RXCUI: 35208
• Pharos Ligand ID: 1W4XLJCGSA9T
• Metabolomics Workbench ID: 43156
• ChEMBL ID: CHEMBL1592
• Mol file: 85441-61-8.mol

Synonyms:2-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid;Accupril;CI 906;CI-906;PD 109,452 2;PD 109452 2;PD 109452-2;PD 1094522;PD-109,452-2;quinapril;quinapril hydrochloride

Chemical Property of Quinapril

Chemical Property:

• Appearance/Colour: white solid
• Melting Point: 120-130 °C
• Boiling Point: 662 °C at 760 mmHg
• PKA: 3.39±0.20(Predicted)
• Flash Point: 354.1 °C
• PSA: 95.94000
• Density: 1.217 g/cm³
• LogP: 2.89590
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 438.21547206
• Heavy Atom Count: 32
• Complexity: 648

Purity/Quality:

99% ^*data from raw suppliers

Quinapril ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Angiotensin-Converting Enzyme Inhibitors
• Canonical SMILES: CCOC(=O)C(CCC1=CC=CC=C1)NC(C)C(=O)N2CC3=CC=CC=C3CC2C(=O)O
• Isomeric SMILES: CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2CC3=CC=CC=C3C[C@H]2C(=O)O
• Recent ClinicalTrials: Diabetic Autonomic Neuropathy and Left Ventricular Function
• Recent EU Clinical Trials: Multi-center, Open-label Study of the Safety and Efficacy of Control of Proteinuria with ACE Inhibitors and ARBS in Patients with Fabry Diseaswe Who Are receiving Farazyme : Tha Farazyme + Arbs + ACE inhibitors Treatments (FAACET) Study: The FAACET Study
• Description: Quinapril is an orally active, non-sulfhydryl ACE inhibitor reportedly useful in the treatment of essential hypertension. The main claimed advantage of quinapril compared with other available ACE inhibitors is its side-effect profile. It is also effective in the management of congestive heart failure.
• Clinical Use: Angiotensin converting enzyme inhibitor: Hypertension Congestive heart failure

Technology Process of Quinapril

There total 11 articles about Quinapril 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: 83.9%

L-Tic-OH (74163-81-8) + N-(1-ethoxycarbonyl-3-phenylpropyl)-L-alanine (877932-98-4,122076-80-6) + L-alanine acid chloride (129178-93-4) → quinapril (85441-61-8,82768-84-1)

Guidance literature:

With benzenesulfonamide; phosphorus pentachloride; triethylamine; In n-heptane; dichloromethane; water;

Reference yield:

quinapril benzyl ester (82586-54-7) → quinapril (85441-61-8,82768-84-1)

Guidance literature:

With hydrogen; palladium on activated charcoal;

DOI:10.1081/SCC-200048435

Reference yield:

C33H38N2O5 → quinapril (85441-61-8,82768-84-1)

Guidance literature:

With hydrogenchloride; hydrogen; 5%-palladium/activated carbon; In ethanol; water; at 35 - 40 ℃; for 5h; under 367.786 Torr; Product distribution / selectivity;

upstream raw materials:

tert-butyl (S)-2-(((S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)-L-alanyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

quinapril hydrochloride

quinapril benzyl ester

[1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine

Downstream raw materials:

ethanol

quinaprilate

<3S-<2(R*),3α,11aβ>>-1,3,4,6,11,11a-hexahydro-3-methyl-1,4-dioxo-α-(2-phenylethyl)-2H-pyrazino<1,2-b>isoquinoline-2-acetic acid, ethyl ester

Refernces

• 1、 -. "A PROCESS FOR THE PREPARATION OF SUBSTANTIALLY PURE 1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID DERIVATIVES". Page/Page column 16-17. . Retrieved 2008/06/13.
• 2、 Li,Guo,Zografi. "Effects of a citrate buffer system on the solid-state chemical stability of lyophilized quinapril preparations". . p. 20 - 26. Retrieved 2007/10/03.