Quinapril hydrochloride Chemical Properties

Melting point:

120-130°C

alpha 

D23 +14.5° (c = 1.2 in ethanol) (Klutchko); D25 +15.4° (c = 2 in methanol) (Goel, Krolls)

storage temp. 

2-8°C

solubility 

H2O: >10mg/mL

form 

solid

color 

white

Water Solubility 

H2O: >10mg/mL

InChIKey

IBBLRJGOOANPTQ-ZKASTLJSNA-N

SMILES

N1(C(=O)[C@H](C)N[C@H](C(=O)OCC)CCC2C=CC=CC=2)CC2C(=CC=CC=2)C[C@H]1C(=O)O.Cl |&1:3,6,28,r|

CAS DataBase Reference

82586-55-8(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

2

RTECS 

NW7176000

HS Code 

2933492250

Hazardous Substances Data

82586-55-8(Hazardous Substances Data)

Toxicity

Freely sol in aq solvents. LD50 in male, female mice, rats (mg/kg): 1739, 1840, 4280, 3541 orally; 504, 523, 158, 107 i.v. (Kaplan, 1989)

Quinapril hydrochloride Usage And Synthesis

Chemical Properties

White Crystalline Solid

Uses

Antihypertensive;Dopamine receptor agonist

Uses

Quinapril is an angiotensin converting enzyme (ACE) inhibitor. Antihypertensive.

Uses

Quinapril hydrochloride has been used as an angiotensin-converting enzyme (ACE) inhibitor to study its effects on renal tubular epithelial cell proliferation in human renal tubular epithelial cells. It has also been used as an ACE inhibitor to evaluate its effects on the expression of angiotensin II (AII) in patient-derived Atheroma samples.

Definition

ChEBI: Quinapril hydrochloride is a hydrochloride resulting from the reaction of equimolar amounts of quinapril and hydrogen chloride. A prodrug for quinaprilat hydrochloride (by hydrolysis of the ethyl ester to the corresponding carboxylic acid), it is used as an angiotensin-converting enzyme inhibitor (ACE inhibitor) for the treatment of hypertension and congestive heart failure. It has a role as an antihypertensive agent and an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor. It contains a quinapril(1+).

brand name

Accupril (Pfizer); Quinapril (Lupin); Quinapril (Ranbaxy) .

General Description

Quinapril hydrochloride,(S)-[(S)-N-[(S)21-carboxy3-phenylpropyl]alanyl]-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid 1-ethyl ester hydrochloride(Acuretic), forms the diacid quinaprilate in thebody. It is more potent than captopril and equipotent to theactive form of enalapril.

Biochem/physiol Actions

Quinapril is a short-acting angiotensin converting enzyme (ACE) inhibitor.

Synthesis

The general procedure for the synthesis of (S)-2-((S)-2-(((S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino)propanoyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride from quinapril benzyl ester maleate was as follows: 1.73 g (3.29 mmol) of quinapril benzyl ester obtained in Example 6 (IlIc, R = Bn) was dissolved in 40 ml of ethyl acetate and about 1 ml of dry HCl was added.The hydrogenation reaction was carried out at 15-20 °C and atmospheric pressure (using a hydrogen balloon) with the addition of 5% Pd/C catalyst (about 100 mg). The progress of the reaction was monitored by LC-MS and after complete consumption of the feedstock, the catalyst was removed by filtration and the filtrate was concentrated. Grinding with methyl tert-butyl ether (MTBE) afforded the target product (S)-2-((S)-2-(((S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino)propanoyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride as a colorless powder in the yield of 1.40 g (90% yield) with a purity of >98% by LC-MS (MH+ 439).1H NMR (showing two rotary isomers) data were as follows: δ 1.18, 1.25 (2t, 3H, OCH2CH3), 1.52 (2d, 3H, CH3), 2.08-2.30 (m, 2H, PhCH2CH2), 2.62, 2.78 (2m, 2H, PhCH2), 3.10-3.35 (m, 2H , H-4), 3.80, 3.93 (2m, 1H, NCHC=O), 4.14, 4.21 (2m, 2H, OCH2), 4.45-4.90 (3m, 3H, Hi, H-i', H-3), 5.15 (m, 1H, NHCHCH3), 7.15-7.35 (m, 9H, ArH), 9.80 (wide m, 2H , NH2), 12.80 (wide m, 1H, COOH). Quinapril hydrochloride can be further purified by ethyl acetate/toluene mixed solvent crystallization as described by S. Klutchko et al. (J. Med. Chem. 1986, 29, 1953-1961).

References

[1] Patent: WO2014/202659, 2014, A1. Location in patent: Page/Page column 22
[2] Patent: WO2004/54980, 2004, A1. Location in patent: Page 25;13;16

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