Title: Imidapril
CAS Registry Number: 89371-37-9
CAS Name: (4S)-3-[(2S)-2-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1-methyl-2-oxo-4-imidazolidinecarboxylic acid
Additional Names: (4S)-3-[(2S)-2-[N-[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]propionyl]-1-methyl-2-oxoimidazolidine-4-carboxylic acid
Molecular Formula: C20H27N3O6
Molecular Weight: 405.44
Percent Composition: C 59.25%, H 6.71%, N 10.36%, O 23.68%
Literature References: Angiotensin converting enzyme (ACE) inhibitor. Prepn: N. Yoneda et al., EP 95163; eidem, US 4508727 (1983, 1985 both to Tanabe Seiyaku); K. Hayashi et al., J. Med. Chem. 32, 289 (1989). Series of articles on pharmacology, pharmacokinetics and metabolism in animals: Arzneim.-Forsch. 42, 446-512 (1992). HPLC determn in plasma and urine: K. Tagawa et al., J. Chromatogr. 617, 95 (1993). Clinical pharmacology: P. Démolis et al., Fundam. Clin. Pharmacol. 8, 80 (1994). Clinical trial in hypertension: M. J. Vandenburg et al., Br. J. Clin. Pharmacol. 37, 265 (1994).
Properties: Colorless crystals from ethyl acetate + n-hexane, mp 139-140°. [a]D20 -71.7° (c = 0.5 in ethanol).
Melting point: mp 139-140°
Optical Rotation: [a]D20 -71.7° (c = 0.5 in ethanol)
Derivative Type: Monohydrochloride
CAS Registry Number: 89396-94-1
Manufacturers' Codes: TA-6366
Trademarks: Novaloc (Schering AG); Tanatril (Tanabe)
Molecular Formula: C20H27N3O6.HCl
Molecular Weight: 441.91
Percent Composition: C 54.36%, H 6.39%, N 9.51%, O 21.72%, Cl 8.02%
Properties: Colorless crystals, mp 214-216° (dec). [a]D20 -64.1° (c = 0.5 in ethanol).
Melting point: mp 214-216° (dec)
Optical Rotation: [a]D20 -64.1° (c = 0.5 in ethanol)
Derivative Type: Diacid
CAS Registry Number: 89371-44-8
Additional Names: Imidaprilat
Molecular Formula: C18H23N3O6
Molecular Weight: 377.39
Percent Composition: C 57.29%, H 6.14%, N 11.13%, O 25.44%
Properties: Crystals, mp 239-241° (dec). [a]D19 -88.4° (c = 1 in 5% NaHCO3).
Melting point: mp 239-241° (dec)
Optical Rotation: [a]D19 -88.4° (c = 1 in 5% NaHCO3)
Therap-Cat: Antihypertensive.
Keywords: ACE-Inhibitor; Antihypertensive; N-Carboxyalkyl (peptide/lactam) Derivatives. |