4-Amino-3(2H)-pyridazinones bearing arylpiperazinylalkyl groups and related compounds: Synthesis and antinociceptive activity

Farmaco

Volumn 58, Issue 11, 2003, Pages 1063-1071

  Dal Piaz, Vittorio ^a   Vergelli, Claudia ^a   Giovannoni, Maria Paola ^a   Scheideler, Mark A ^b   Petrone, Giuseppe ^b   Zaratin, Paola ^b  

^a UNIVERSITY OF FLORENCE   (Italy)

^b GSK   (Italy)

Author keywords

Antinociceptive activity; Arylpiperazinylalkylpyridazinones; Emorfazone; SARs studies; Synthesis

Indexed keywords

ALKYL GROUP; EMORFAZONE; PYRIDAZINONE DERIVATIVE;

ANTINOCICEPTION; ARTICLE; DOSE RESPONSE; DRUG EFFECT; DRUG SYNTHESIS; LIGATION; NOCICEPTIVE STIMULATION; REDUCTION; STRUCTURE ACTIVITY RELATION;

EID: 0142155717     PISSN: 0014827X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0014-827X(03)00162-9     Document Type: Article

References (19)

1. Allison M.C., Howatson A.G., Torrance C.J., Lee F.D., Russel R.I. Gastrointestinal damage associated with the use of nonsteroidal antiinflammatory drugs. N. Engl. J. Med. 327:1992;749-754.
2. Walsh T.D. Prevention of opioid side effects. J. Pain Symptom Manage. 5:1990;362-369.
3. Ollat H., Cesaro P. Pharmacology of neuropathic pain. Clin. Neuropharmacol. 18:1995;391-404.
4. Wermuth G.C. Derives pyridaziniques presentant un interet therapeutique I. Revue generale et contribution personnelle. Aggressologie. 6:1965;383-398.
5. Takaya M., Sato M., Terashima H., Tanizawa H., Maki Y. A new nonsteroidal analgesic-antiinflammatory agent. Synthesis and activity of 4-ethoxy-2-methyl-5-morpholino-3(2H)-pyridazinone and related compounds. J. Med. Chem. 22:1979;53-58.
6. Sato M., Ishizuka Y., Yamaguchi A. Pharmacological investigation of 4-ethoxy-2-methyl-5-morpholino-3(2H)-pyridazinone. Arzneim. Forsch. 31:1981;1738-1745.
7. Sato M., Yamaguchi A. Studies on mechanism of action of Emorfazone. Arzneim. Forsch. 32:1982;379-382.
8. Rubat C., Coudert P., Albuisson E., Bastide J., Couquelet J., Tronche P. Synthesis of Mannich bases of arylidenepyridazinones as analgesic agents. J. Pharm. Sci. 81:1992;1084-1087.
9. Dal Piaz V., Giovannoni M.P., Ciciani G., Barlocco D., Giardina G., Petrone G., Clarke G.D. 4,5-Functionalized 6-phenyl-3(2H)-pyridazinones: synthesis and evaluation of antinociceptive activity. Eur. J. Med. Chem. 31:1996;65-70.
10. Viaud M.C., Jamoneau P., Flouzat C., Bizot-Espiard J.G., Pfeiffer B., Renard P., Caignard D.H., Adam G., Guillaumet G. N-Substituted oxazolo[4,5-b]pyridin-2(1H)-ones: a new class of nonopiate antinociceptive agents. J. Med. Chem. 38:1995;1278-1286.
11. Pieretti S., Dal Piaz V., Matucci R., Giovannoni M.P., Galli A. Antinociceptive activity of 3(2H)-pyridazinone derivative in mice. Life Sci. 65:1999;1381-1394.
12. Sprio V., Aiello E., Mazza A. Studies on nitrogen heterocycles. Hydrogenation of isoxazolo[3,4-d]pyridazin-4-ones and isoxazolo[3,4-d]pyridazin- 4,7-diones. Ann. Chim. 57:1967;836-845.
13. Renzi G., Dal Piaz V. Studies on some ethyl-4,5-disubstituted isoxazole-3-carboxylates. Gazz. Chim. Ital. 95:1965;1478-1491.
14. Lespagnol A., Deprey J. Pyridazine derivatives. Bull. Soc. Chim. France. 3:1961;606-610.
15. Nitta Y., Yoneda F., Ohtaka T., Kato T. Pyridazines V. Derivatives of 6-phenyl-3(2H)-pyridazinones. Chem. Pharm. Bull. (Tokyo). 12:1964;69-73.
16. V. Dal Piaz, unpublished results.
17. Dal Piaz V., Ciciani G., Giovannoni M.P. Reductive cleavage of isoxazolo[3,4-d]pyridazinones: a synthetic approach to various 4,5-functionalized-3(2H)-pyridazinones. Heterocycles. 32:1991;1173-1179.
18. Siegmund E., Cadmus R., Lu G. Proc. Soc. Expt. Biol. Med. 95:1957;729-731.
19. Milne G.E., Twomey T.M. The analgesic properties of piroxicam in animals and correlation with experimentally determined plasma levels. Agents Actions. 10:1980;31-37.