Asymmetric N-(3,3-diphenylpropyl)aminoalkyl esters of 4-aryl-2,6- dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acids with antihypertensive activity

European Journal of Medicinal Chemistry

Volumn 33, Issue 5, 1998, Pages 399-420

  Leonardi, Amedeo ^a   Motta, Gianni ^a   Pennini, Renzo ^a   Testa, Rodolfo ^a   Sironi, Giorgio ^a   Catto, Alberto ^a   Cerri, Alberto ^b   Zappa, Marco ^c   Bianchi, Giorgio ^d   Nardi, Dante ^e  

^a Recordati SpA   (Italy)

^b Prassis Sigma Tau Research Institute   (Italy)

^c Ist Biochimico Pavese Pharma S   (Italy)

^d Crinos Biological Research Laboratories   (Italy)

^e NONE   (Italy)

Author keywords

1,4 dihydropyridine; 2375; Antihypertensive; Calcium antagonist; Calcium entry blocker; Lercanidipine; Rec 15

Indexed keywords

1,4 DIHYDROPYRIDINE; CALCIUM CHANNEL; LERCANIDIPINE; NITRENDIPINE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIHYPERTENSIVE ACTIVITY; ARTICLE; BINDING SITE; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; FEMALE; MALE; MOUSE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; SPONTANEOUSLY HYPERTENSIVE RAT; STRUCTURE ACTIVITY RELATION;

EID: 0032104202     PISSN: 02235234     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0223-5234(98)80015-9     Document Type: Article

References (52)

1. [1] Opie L.H., Clinical Use of Calcium Channel Antagonist Drugs, Kluwer, Dordrecht, 1990, pp. 70-131.
2. [2] Zanchetti A., Am. J. Cardiol. 59 (1987) 130B-136B.
3. [3] Fisher M., Grotta G., Drugs 46 (1993) 961-975.
4. [4] Phillips R.A., J. Cardiovasc. Pharmacol. 20 (2) (1993) S55-S62.
5. [5] Nayler W.G., Drugs 42 (1991) 21-27.
6. [6] Morris A.D., Reid J.L., J. Cardiovasc. Pharmacol. 20 (A) (1992) S25-S32.
7. [7] Keogh A.M., Schroeder J.S., J. Cardiovasc. Pharmacol. 16 (6) (1990) S28-S35.
8. [8] Janis R.A., Silver P., Triggle D.J., Adv. Drug Res. 16 (1987) 309-591.
9. [9] Mannhold R., Drugs of Today 20 (1984) 69-90.
10. [10] Kendall H.E., Luscombe D.K., Prog. Med. Chem. 24 (1987) 249-297.
11. [11] Bossert F., Meyer H., Weheringer E., Angew. Chem. Int. Ed. Engl. 20 (1981) 762-769.
12. [12] Triggle D.J., Langs D.A., Janis R.A., Med. Res. Rev. 9 (1989) 123-180.
13. [13] Iwanami M., Shibanuma T., Fujimoto M., Kawai R., Tamazawa K., Takenaka T., Takahashi K., Murakami M., Chem. Pharm. Bull. 27 (1979) 1426-1440.
14. [14] Tamazawa K., Arima H., Kojima T., Isomura Y., Okada M., Fujita S., Furuya T., Takenaka T., Inagaki O., Terai M., J. Med. Chem. 29 (1986) 2504-2511.
15. [15] Muto K., Kuroda T., Kawato H., Karasawa A., Kubo K., Nakamizo N., Arzneim. Forsch. Drug Res. 38 (1988) 1662-1665.
16. [16] Meguro K., Aizawa M., Sohda T., Kawamatsu Y., Nagaoka A., Chem. Pharm. Bull. 33 (1985) 3787-3797.
17. [17] Osumi S., Morishita S., Wada K., Usui H., Kanda M., Matsui H., Kakeya N., Tohoku J. Exp. Med. 155 (1988) 205-206 [Chem. Abstr. 109 (1988) 183234r].
18. [17] Osumi S., Morishita S., Wada K., Usui H., Kanda M., Matsui H., Kakeya N., Tohoku J. Exp. Med. 155 (1988) 205-206 [Chem. Abstr. 109 (1988) 183234r].
19. [18] Kanno H., Yamaguchi H., Okamiya Y., Sunakawa K., Takeshita T., Naruchi T., Chem. Pharm. Bull. 40 (1992) 2049-2054.
20. [19] Godard P., Tillement J.P., Med. Actuelle 4 (1977) 165-172.
21. [20] Klein G., Drug Dev. Eval. 11 (1985) 3-23.
22. [21] Kasuya Y., Fujie K., Yakugaku Zasshi 78 (1958) 551-553 [Chem. Abstr. 52 (1958) 17196a].
23. [21] Kasuya Y., Fujie K., Yakugaku Zasshi 78 (1958) 551-553 [Chem. Abstr. 52 (1958) 17196a].
24. [22] Donaruma L.G., J. Org. Chem. 26 (1961) 4737-4738.
25. [23] Meyer H., Wehinger E., Bossert F., Scherling D., Arzneim. Forsch. Drug Res. 33 (1983) 106-112.
26. [24] Braine R., Bull. Soc. Chim. Belg. 63 (1954) 419-423.
27. [25] Sato Y., Ger. Offen 2,629,892 [Chem. Abstr. 86 (1977) 189726f].
28. [26] Grohe K., Frohberger P.E., Ger. Offen 2,253,027 [Chem. Abstr. 81 (1972) 25653].
29. [27] Guarneri L., Angelico P., Ibba M., Poggesi E., Taddei C., Leonardi A., Testa R., Arzneim. Forsch. Drug Res. 46 (1996) 15-24.
30. [28] Friebel H. et al., Arch. Exp. Path. Pharmacol. 232 (1958) 419.
31. [29] Loev B., Goodman M.M., Snader K.M., Tedeschi R., Macko E., J. Med. Chem. 17 (1974) 956-965.
32. [30] Bolger G.T., Gengo P., Klockowski R., Luchowski E., Siegel H., Janis R.A., Triggle A.M., Triggle D.J., J. Pharmacol. Exp. Ther. 225 (1987) 291-309.
33. [31] Coburn R.A., Wierzba M., Suto M.J., Solo A.J., Triggle A.M., Triggle D.J., J. Med. Chem. 31 (1988) 2103-2107.
34. [32] Sironi G., Montagna E., Greto L., Bianchi G., Leonardi A., Testa R., Arzneim. Forsch. Drug Res. 46 (1996) 145-152.
35. [33] Barchielli M., Dolfini E., Farina P., Leoni B., Targa G., Vinaccia V., Tajana A., J. Cardiovasc. Pharmacol. 29 (Suppl. 2) (1997) S1-S15.
36. [34] Herbette L.G., Vecchiarelli M., Leonardi A., J. Cardiovasc. Pharmacol. 29 (Suppl. 1) (1997) S19-S24.
37. [35] Guarneri L., Sironi G., Angelico P., Ibba M., Greto L., Colombo D., Leonardi A., Testa R., J. Cardiovasc. Pharmacol. 29 (Suppl. 1) (1997) S25-S32.
38. [36] Goldmann S., Stoltefuss J., Angew. Chem. Int. Ed. Engl. 30 (1991) 1559-1578.
39. [37] 'Focus on Lercanidipine, a New Calcium Antagonist'. J. Cardiovasc. Pharmacol. 29 (Suppl. 1) (1997); 'Clinical Profile of Lercanidipine', J. Cardiovasc. Pharmacol. 29 (Suppl. 2) (1997).
40. [37] 'Focus on Lercanidipine, a New Calcium Antagonist'. J. Cardiovasc. Pharmacol. 29 (Suppl. 1) (1997); 'Clinical Profile of Lercanidipine', J. Cardiovasc. Pharmacol. 29 (Suppl. 2) (1997).
41. [38] Testa R., Leonardi A., Tajana A., Riscassi E., Magliocca R., Sartani A., Cardiovasc. Drug Res., 15 (1997) 187-219.
42. [39] Dal Monte D., Sandri E., Cere W., Ann. Chim. 60 (1970) 801-814.
43. [40] Wehinger E., Bessert F., Ger. Offen 2,847,237 [Chem. Abstr. 93 (1977) 150124].
44. [41] Bockmuhl M., Stein L., Ger. Offen 925,468 [Chem. Abstr. 52 (1958) 3869e].
45. [42] Leonard N.J., Durand D.A., J. Org. Chem. 33 (1968) 1322-1333.
46. [43] Pitha J., Hermanek S., Vit J., Coll. Czech Chem. Commun. 25 (1960) 736-742.
47. [44] Goldberg S.D., Ringk W.M.F., Spoerri P.E., J. Am. Chem. Soc. (1939) 3562-3564.
48. [45] Albert A., Serjeant E.P., The Determination of Ionization Constants, Chapman and Hall, London, 1971.
49. [46] Motomura S., Hashimoto K., J. Cardiovasc. Pharmacol. 10 (1987) 627-635.
50. [47] Purcell W.P., Bass G.E., Clayton J.M., Strategy of Drug Design: A Guide to Biological Activity, Wiley, 1987, pp. 126-143.
51. [48] De Lean A., Munson P.J., Rodbard D., Am. J. Physiol. 235 (1978) E97-E102.
52. [49] Weil C.S., Biometrics 8 (1952) 249.