4911. Imidapril

Nomenclature

CAS number: 89371-37-9
(4S)-3-[(2S)-2-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1-methyl-2-oxo-4-imidazolidinecarboxylic acid; (4S)-3-[(2S)-2-[N-[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]propionyl]-1-methyl-2-oxoimidazolidine-4-carboxylic acid.
C20H27N3O6; mol wt 405.44.
C 59.25%, H 6.71%, N 10.36%, O 23.68%.

Description and 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).

Chemical structure

Properties

Colorless crystals from ethyl acetate + n-hexane, mp 139-140°. [α]D20 71.7° (c = 0.5 in ethanol).

Derivative

Monohydrochloride.

Nomenclature

CAS number: 89396-94-1
TA-6366; Novaloc (Schering AG); Tanatril (Tanabe).
C20H27N3O6.HCl; mol wt 441.91.
C 54.36%, H 6.39%, N 9.51%, O 21.72%, Cl 8.02%.

Properties

Colorless crystals, mp 214-216° (dec). [α]D20 64.1° (c = 0.5 in ethanol).

Derivative

Diacid.

Nomenclature

CAS number: 89371-44-8
Imidaprilat.
C18H23N3O6; mol wt 377.39.
C 57.29%, H 6.14%, N 11.13%, O 25.44%.

Properties

Crystals, mp 239-241° (dec). [α]D19 88.4° (c = 1 in 5% NaHCO3).

Therapeutic Category

Antihypertensive.

Keywords

ACE-Inhibitor; Antihypertensive; N-Carboxyalkyl (peptide/lactam) Derivatives