Novel selective hindlimb vasodilators: Synthesis and biological activity of 1-acyl-4-aminopiperidine derivatives

Journal of Medicinal Chemistry

Volumn 46, Issue 14, 2003, Pages 3033-3044

  Teramoto, Shuji ^a   Tanaka, Michinori ^a   Shimizu, Hiroshi ^a   Fujioka, Takafumi ^b   Tabusa, Fujio ^a   Imaizumi, Takashi ^c   Yoshida, Kenji ^d   Fujiki, Hiroyuki ^c   Mori, Toyoki ^c   Sumida, Takumi ^d   Tominaga, Michiaki ^e  

^a Medicinal Chemistry Research Institute   (Japan)

^b Tokushima Research Institute   (Japan)

^c Res Inst Pharmacol/Therapeut D   (Japan)

^d Fujii Memorial Research Institute   (Japan)

^e OTSUKA PHARMACEUTICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 (3,5 DIMETHYL 4 PROPIONYLAMINO)BENZOYL 4 (N METHYL 2 PHENYLETHYL)AMINOPIPERIDINE HYDROCHLORIDE; 1 ACYL 4 AMINOPIPERIDINE DERIVATIVE; 6 (4 AMINO 1 PIPERIDINYL)CARBONYL 2(1H) QUINOLONE DERIVATIVE; UNCLASSIFIED DRUG; VASODILATOR AGENT;

ANIMAL TISSUE; ARTERY BLOOD FLOW; ARTICLE; BLOOD PRESSURE; CLINICAL TRIAL; CORONARY ARTERY BLOOD FLOW; DOG; DRUG ACTIVITY; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; FEMORAL ARTERY; HINDLIMB; HUMAN; INTERMITTENT CLAUDICATION; ISOLATED HEART; LEG BLOOD FLOW; NONHUMAN; RAYNAUD PHENOMENON; STRUCTURE ACTIVITY RELATION; VASODILATATION;

ANIMALS; ARTERIES; BLOOD PRESSURE; CORONARY CIRCULATION; DOGS; FEMUR; HINDLIMB; PIPERIDINES; QUINOLONES; REGIONAL BLOOD FLOW; STRUCTURE-ACTIVITY RELATIONSHIP; VASODILATOR AGENTS;

EID: 0038121711     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020597o     Document Type: Article

References (16)

1. Dawson, D. L.; Cutler, B. S.; Meissner, M. H.; Strandness, D. E., Jr. Cilostazol has beneficial effects in treatment of intermittent claudication. Circulation 1998, 98, 678-686.
2. Lievre, M.; Morand, S.; Besse, B.; Fiessinger, J.-N.; Boissel, J.P. Oral Beraprost sodium, a prostaglandin I2 analogue, for intermittent claudication. Circulation 2000, 102, 426-431.
3. Rynaud's Treatment Study Investigators. Comparison of sustained-release nifedipine and temperature biofeedback for treatment of primary Raynaud's phenomenon. Arch. Intern. Med. 2000, 160, 1101-1108.
4. Coffman, J. D.; Clement, D. L.; Creager, M. A.; Dormandy, J. A.; Janssens, M. M.-L.; McKendry, R. J. R.; Murray, G. D.; Nielsen, S. L. International study of Ketanserin in Raynaud's phenomenon. Am. J. Med. 1989, 87, 264-268.
5. Black, C. M.; Halkier-Sørensen, L.; Belch, J. J. F.; Ullman, S.; Madhok, R.; Smit, A. J.; Banga, J.-D.; Watson, H. R. Oral Iloprost in Raynaud's phenomenon secondary to systemic sclerosis: A multicentre, placebo-controlled, dose-comparison study. Br. J. Rheumatol. 1998, 37, 952-960.
6. Ettinger, W. H.; Wise, R. A.; Schaffhauser, D.; Wigley, F. M. Controlled double-blind trial of Dazoxiben and Nifedipine in the treatment of Raynaud's phenomenon. Am. J. Med. 1984, 77, 451-456.
7. Wigley, F. M.; Wise, R. A.; Malamet, R.; Scott, T. E. Nicardipine in the treatment of Raynaud's phenomenon. Arthritis Rheum. 1987, 30, 281-286.
8. Wigley, F. M.; Korn, J. H.; Csuka, M. E.; Medsger, T. A., Jr.; Rothfield, N. F.; Ellman, M.; Martin, R.; Collier, D. H.; Weinstein, A.; Furst, D. E.; Jimenez, S. A.; Mayes, M. D.; Merkel, P. A.; Gruber, B.; Kaufman, L.; Varga, J.; Bell, P.; Kern, J.; Marrott, P.; White, B.; Simms, R.; Phillips, A. C.; Seibold, J. R. Oral Iloprost treatment in patients with Raynaud's phenomenon secondary to systemic sclerosis. Arthritis Rheum. 1998, 41, 670-677.
9. Wollersheim, H.; Thien, T. Dose-response study of prazosin in Raynaud's phenomenon: Clinical effectiveness versus side effects. J. Clin. Pharmacol. 1988, 28, 1089-1093.
10. Tominaga, M.; Yo, E.; Ogawa, H.; Yamashita, S.; Yabuuchi, Y.; Nakagawa, K. Studies on positive inotropic agents. II. Synthesis of (4-substituted 1-piperazinylcarbonyl)-2(1H)-quinolinone derivatives. Chem. Pharm. Bull. 1986, 34, 682-693.
11. Kametani, T.; Nemoto, H. Chichibabin reaction. II. Chichibabin reaction of 8-methylquinoline and migration of the methyl group in the synthesis of 3,4-dihydro-8-methylcarbostyril by Friedel-Crafts reaction. (Studies on the syntheses of heterocyclic compounds. CCIII). Chem. Pharm. Bull. 1967, 15, 1910-1915.
12. Gassman, P. G.; Gruetzmacher, G. D. Azasulfonium salt. Intermediates in a general procedure for the alkylation of aromatic amines. J. Am. Chem. Soc. 1974, 96, 5487-5495.
13. King, L. C. The reaction of iodine with some ketones in the presence of pyridine. J. Am. Chem. Soc. 1944, 66, 894-895.
14. Adachi, M.; Sasakura, K.; Sugasawa, T. Aminohaloborane in organic synthesis. IX. Exclusive ortho acylation reaction of N-monoaminoalkylanilines. Chem. Pharm. Bull. 1985, 33, 1826-1835.
15. Orito, K.; Imaizumi, T.; Yoshida, K.; Fujiki, H.; Kishi, M.; Teramoto, S.; Tanaka, M.; Shimizu, H.; Tominaga, M.; Kimura, Y.; Kambayashi, J.; Mori, T. Mechanisms of action of OPC-28326, a selective hindlimb vasodilator. J. Pharmacol. Exp. Ther. 1999, 291, 604-611.
16. Endoh, M.; Hashimoto, K. Pharmaceutical evidence of autonomic nerve activity in canine papillary muscle. Am. J. Physiol. 1979, 218, 1459-1463.