| Identification | More | [Name]
Quinapril hydrochloride | [CAS]
82586-55-8 | [Synonyms]
(3S)-2-[(2S)-2-[[(1S)-1-(ETHOXYCARBONYL)-3-PHENYLPROPYL]AMINO]-1-OXOPROPYL]-1,2,3,4-TETRAHYDRO-3-ISOQUINOLINECARBOXYLIC ACID HYDROCHLORIDE
ACCUPRIL
ACCUPRIN
ACCUPRO
CI-906
PD-109452-2
QUINAPRIL HCL
QUINAPRIL HYDROCHLORIDE
3-isoquinolinecarboxylicacid,1,2,3,4-tetrahydro-2-(2-((1-(ethoxycarbonyl)-3-p
monohydrochloride,(3s-(2(r*(r*)),3r*))-henylpropyl)amino)-1-oxopropyl)
QUINAPRIL HYDROCHLORIDE, RELATED COMPOUND B3-ISOQUINOLINECARBOXYLIC ACID, 2-[2-[(1-CARBOXY-3-PHENYLPROPYL)AMINO]-1-OXOPROPYL]-1,2,3,4-TETRAHYDRO-,[3S-[2[R*(R*)],3R*]]-USP STANDARD
QUINAPRIL HYDROCHLORIDE, RELATED COMPOUND A ETHYL[3S-[2(R*),3A,11A BETA]]-1,3,4,6,11,11A-HEXAHYDRO-3-METHYL-1,4-DIOXO-ALPHA-(2-PHENYLETHYL)-2H-PYRAZINO[1,2-B]ISOQUINOLINE-2-ACETATE USP STANDARD
QuinaprilHclC25H30N205.HC1
CI-906, PD-109452-2, Accupril, Accuprin, Accupro
Accupron
3-Isoquinolinecarboxylic acid, 2-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-, monohydrochloride, (3S)-(9CI)
3-Isoquinolinecarboxylic acid, 2-[2-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-, monohydrochloride, [3S-[2[R*(R*)],3R*]]-
Acequide
Acequin
Acuitel | [EINECS(EC#)]
620-479-5 | [Molecular Formula]
C25H31ClN2O5 | [MDL Number]
MFCD00889215 | [Molecular Weight]
474.98 | [MOL File]
82586-55-8.mol |
| Chemical Properties | Back Directory | [Appearance]
White Crystalline Solid | [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 | [Usage]
An angiotensin converting enzyme (ACE) inhibitor. Antihypertensive | [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 Data | Back Directory | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [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) |
| Hazard Information | Back Directory | [Chemical Properties]
White Crystalline Solid | [Uses]
Antihypertensive;Dopamine receptor agonist | [Uses]
Quinapril is an angiotensin converting enzyme (ACE) inhibitor. Antihypertensive. | [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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