82586-55-8
82586-55-8 結(jié)構(gòu)式
基本信息
鹽酸三羰苯喹
鹽酸喹那普利
喹那普列
喹那普利鹽酸鹽
(3S-(2(R*(R*)),3R*))-2-(2-((1-乙氧羰基-3-苯丙基)氨基)-1-氧代丙基)-1,2,3,4-四氫-3-異喹啉羧酸鹽酸鹽
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
物理化學(xué)性質(zhì)
安全數(shù)據(jù)
制備方法
82586-54-7
82586-55-8
以喹那普利芐酯馬來酸鹽為原料合成(S)-2-((S)-2-(((S)-1-乙氧基-1-氧代-4-苯基丁-2-基)氨基)丙酰基)-1,2,3,4-四氫異喹啉-3-羧酸鹽酸鹽的一般步驟如下：將實施例6所得的1.73g（3.29mmol）喹那普利芐酯（IlIc，R = Bn）溶解于40ml乙酸乙酯中，加入約1ml干燥的HCl。在15-20℃及大氣壓（使用氫氣氣球）下，加入5% Pd/C催化劑（約100mg）進(jìn)行氫化反應(yīng)。通過LC-MS監(jiān)測反應(yīng)進(jìn)程，待原料完全消耗后，過濾去除催化劑，濃縮濾液。用甲基叔丁基醚（MTBE）研磨，得到目標(biāo)產(chǎn)物(S)-2-((S)-2-(((S)-1-乙氧基-1-氧代-4-苯基丁-2-基)氨基)丙?；?-1,2,3,4-四氫異喹啉-3-羧酸鹽酸鹽，為無色粉末，產(chǎn)量1.40g（收率90%），LC-MS純度>98%（MH+ 439）。1H NMR（顯示兩個旋轉(zhuǎn)異構(gòu)體）數(shù)據(jù)如下：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（寬m, 2H, NH2）, 12.80（寬m, 1H, COOH）。根據(jù)S.Klutchko等人所述（J. Med. Chem. 1986, 29, 1953-1961），可通過乙酸乙酯/甲苯混合溶劑結(jié)晶進(jìn)一步純化喹那普利鹽酸鹽。
參考文獻(xiàn)：
[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
常見問題列表
| Target | Value |
| ACE |
Quinapril (hydrochloride) (CI-906) is an angiotensin-converting enzyme inhibitor (ACE inhibitor) used in the treatment of hypertension and congestive heart failure. Quinapril is rapidly de-esterified after absorption to quinaprilat (the active diacid metabolite), a potent angiotensin converting enzyme (ACE) inhibitor.