New non-peptide endothelin-a receptor antagonists: Synthesis, biological properties, and structure-activity relationships of 5-(dimethylamino)-N- pyridyl-, -N-pyrimidinyl-, -N-pyridazinyl-, and -N-pyrazinyl-1- naphthalenesulfonamides

Journal of Medicinal Chemistry

Volumn 40, Issue 6, 1997, Pages 996-1004

  Bradbury, Robert H ^a   Bath, Colin ^a   Butlin, Roger J ^a   Dennis, Michael ^a   Heys, Christine ^a   Hunt, Sarah J ^a   James, Roger ^a   Mortlock, Andrew A ^a   Sumner, Neil F ^a   Tang, Eric K ^a   Telford, Berwick ^a   Whiting, Elaine ^a   Wilson, Campbell ^a  

^a ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1 NAPHTHALENESULFONAMIDE DERIVATIVE; 5 (DIMETHYLAMINO) N (5 CHLORO 3 METHOXY 2 PYRAZINYL) 1 NAPHTHALENESULFONAMIDE; 5 DIMETHYLAMINO N (3,4 DIMETHYL 5 ISOXAZOLYL) 1 NAPHTHALENESULFONAMIDE; BIG ENDOTHELIN 1; ENDOTHELIN A RECEPTOR; ENDOTHELIN A RECEPTOR ANTAGONIST; ENDOTHELIN B RECEPTOR; SULFONAMIDE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTIHYPERTENSIVE ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ANTAGONISM; DRUG SYNTHESIS; ERYTHROLEUKEMIA CELL; FEMALE; GUINEA PIG; HYPERTENSION; INTRAVENOUS DRUG ADMINISTRATION; MALE; MOUSE; NONHUMAN; ORAL DRUG ADMINISTRATION; PORTAL VEIN; PRESSOR RESPONSE; RAT; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION; VENOCONSTRICTION;

ANIMALS; ANTIHYPERTENSIVE AGENTS; BLOOD PRESSURE; DANSYL COMPOUNDS; ENDOTHELIN-1; ENDOTHELINS; GUINEA PIGS; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MOLECULAR STRUCTURE; PROTEIN BINDING; PROTEIN PRECURSORS; RATS; RATS, WISTAR; RECEPTOR, ENDOTHELIN A; RECEPTORS, ENDOTHELIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 15444356975     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9604585     Document Type: Article

References (55)

1. Yanagisawa, M.; Kurihara, H.; Kimura, H.; Tomobe, Y.; Kobayashi, M.; Mitsui, Y.; Goto, K.; Masaki, T. A Novel Potent Vasoconstrictor Peptide Produced by Vascular Endothelial Cells. Nature 1988, 332, 411-415.
2. Masaki, T.; Yanagisawa, M.; Goto, K. Physiology and Pharmacology of Endothelins. Med. Res. Rev. 1992, 4, 391-421.
3. Wilson, C.; Hargreaves, R. B. Inhibition of the Pharmacological Effects of Endothelin. Prog. Med. Chem. 1994, 31, 371-410.
4. Doherty, A. M. Development of Agents to Modulate the Effects of Endothelin. Current Med. Chem. 1994, 1, 271-312.
5. Walsh, T. F. Progress in the Development of Endothelin Antagonists. Annu. Rep. Med. Chem. 1995, 30, 91-100.
6. Takashi, K.; Totsune, K.; Mouri, T. Endothelin in Chronic Renal Failure. Nephron 1994, 66, 373-379.
7. Cosentino, F.; Katusic, Z. S. Does Endothelin-1 Play a Role in the Pathogenesis of Cerebral Vasospasm? Stroke 1994, 25, 904-908.
8. Gaid, A.; Yanagisawa, M.; Langleben, D.; Michel, R.; Levy, R.; Shennib, S.; Kimura, S.; Masaki, T.; Duguid, W.; Path, F. R. C.; Stewart, D. J. Expression of Endothelin-1 in the Lungs of Patients with Pulmonary Hypertension. N. Engl. J, Med, 1993, 328, 1732-1739.
9. Arai, H.; Hori, S.; Aramori, I.; Ohkubo, H.; Nakanishi, S. Cloning and Expression of a cDNA Encoding an Endothelin Receptor. Nature 1990, 348, 730-732.
10. Sakurai, T.; Yanagisawa, M.; Takuwu, Y.; Miyazaki, H.; Kimuar, S.; Goto, K.; Masaki, T. Cloning of a cDNA Encoding a Non-Isopeptide-Selective Subtype of the Endothelin Receptor. Nature 1990, 348, 732-735.
11. Panek, R. L.; Major, T. C.; Hingorani, G. P.; Doherty, A. M.; Taylor, D. G.; Rapundalo, S. T. Endothelin and Structurally Related Analogs Distinguish Between Endothelin Receptor Subtypes. Biochem. Biophys. Res. Commun. 1992, 183, 566-571.
12. B Receptors Mediate Vascular Smooth Muscle Contraction. Br. J. Pharmacol. 1992, 107, 858-860.
13. Warner, T. D.; Allcock, G. H.; Corder, R.; Vane, J. R. Use of the Endothelin Antagonists BQ-123 and PD 142893 to Reveal Three Endothelin Receptors Mediating Smooth Muscle Contraction and the Release of EDRF. Br. J. Pharmacol. 1993, 110, 777-782.
14. Ohlstein, E. H.; Arleth, A.; Bryan, H.; Elliott, J. D.; Sung, C. P. The Selective Endothelin-A Receptor Antagonist BQ-123 Antagonises ET-1 Mediated Mitogenesis in Vascular Smooth Muscle. Eur. J. Pharmacol. 1992, 225, 347-350.
15. B Receptor Mediates Both Vasodilatation and Vasoconstriction In Vivo. Biochem. Biophys. Res. Commun. 1992, 186, 867-873.
16. B Like Receptors. Biochem. Biophys. Res. Commun. 1992, 184, 100-106.
17. Godfraind, T. Endothelin Receptors in Human Coronary Arteries. Trends Pharmacol. Sci. 1994, 15, 136.
18. Davenport, A. P.; Maguire, J. J. Endothelin Receptors in Human Coronary Arteries - Reply. Trends Pharmacol. Sci. 1994, 15 136-137.
19. Tschudi, M. R.; Luscher, T. F. Characterization of Contractile Endothelin and Angiotensin Receptors in Human Resistance Arteries: Evidence for Two Endothelin and One Angiotensin Receptor. Biochem. Biophys. Res. Commun. 1994, 204, 685-690.
20. B Receptors Mediate Contraction in Human Blood Vessels. Circulation 1994, 89, 1203-1208.
21. Fukami, T.; Nagasi, T.; Fujita, K.; Hayama, T.; Niyama, K.; Mase, T.; Nakajima, S.; Fukuroda, T.; Saeki, T.; Nishikibe, M.; Ihara, M.; Yano, M.; Ishikawa, K. Structure-Activity Relationships of Cyclic Pentapeptide Endothelin A Receptor Antagonists. J. Med. Chem. 1995, 38, 4309-4324.
22. A Receptor Antagonist. J. Pharmacol. Exp. Ther. 1993, 264, 1040-1046.
23. Ishikawa, K.; Ihara, M.; Noguchi, K.; Mase, T.; Mino, N.; Saeki, T.; Fukuroda, T.; Fukami, T.; Ozaki, S.; Nagase, T.; Nishikibe, J.; Yano, M. Biochemical and PharmacologicalProfile of a Potent and Selective Endothelin B-Receptor Antagonist BQ-788. Proc. Natl. Acad. Sci. U.SA. 1994, 91, 4892-4896.
24. Cody, W. L,; Doherty, A. M.; He, J. X.; DePue, P. M.; Rapundalo, S. T.; Hingorani. G. A.; Major, T. C.; Panek, R. L.; Haleen, S.; La Douceur, D.; Reynolds, E. E.; Hill, K. E.; Flynn, M. A. Design of a Functional Antagonist of Endothelin. J. Med. Chem. 1992, 35, 3301-3303.
25. B Receptor Antagonist. Med. Chem. Res. 1993, 3, 154-162.
26. Ohlstein, E. H.; Vickery-Clark, L. M.; Storer, B. L.; Douglas, S. A. Antihypertensive Effects of the Endothelin Receptor Antagonist BQ-123 in Conscious Spontaneously Hypertensive Rats. J. Cardiovasc. Pharmacol. 1993, 22, S321-S324.
27. A Receptor Antagonist in the Rat. J. Clin. Invest. 1994, 93, 900-906.
28. Clozel, M.; Breu, V.; Burri, K.; Cassal, J.-M.; Fischli, W.; Gray, G. A.; Hirth, G.; Loffler, B. M.; Muller, M.; Neidhart, W.; Ramuz, H. Pathophysiological Roles of of Endothelin Revealed by the First Orally Active Endothelin Receptor Antagonist. Nature 1993, 365, 759-761.
29. Roux, S. P.; Clozel, M.; Sprecher, U.; Gray, G.; Clozel, J. P. Ro 47-0203, a New Endothelin Receptor Antagonist Reverses Chronic Vasospasm in Experimental Subarachnoid Hemorrhage. Circulation 1993, 88, 1-170.
30. Stein, P. D.; Hunt, J. T.; Floyd, D. M.; Moreland, S.; Dickinson, K. E. J.; Mitchell, C.; Liu, E. C.-K.; Webb, M. L.; Murugesan, N.; Dickey, J.; McMullen, D.; Zhang, R.; Lee, V. G.; Serafino, R.; Delaney, C.; Schaeffer, T. R.; Kozlowski, M. The Discovery of Sulfonamide Endothelin Antagonists and the Development of the Orally Active ETA Antagonist 5-(Dimethylamino)-N-(3,4-dimethyl-5-isoxazolyl)-1-naphthalenesulfonamide. J. Med. Chem. 1994, 37, 329-331.
31. A-Selective Antagonists. J. Med. Chem. 1995, 38, 1344-1354.
32. Elliott, J. D.; Lago, M. A.; Cousins, R. D.; Gao, A.; Leber, J. D.; Erhard, K. F.; Nambi, P.; Elshourbagy, N. A.; Kumar, C.; Lee, J. A.; Bean, J. W.; DeBrosse, C. W.; Eggleston, D. S.; Brooks, D. P.; Fueurstein, G.; Ruffolo, R. R.; Weinstock, J.; Gleason, J. G.; Peishoff, C. E.; Ohlstein, E. H. 1,3-Diarylindan-2-carboxylic Acids, Potent and Selective Non-Peptide Endothelin receptor Antagonists. J. Med. Chem. 1994, 37, 1553-1557.
33. Winn, M.; Tasker, A. S.; Boyd, S. A.; Jae, H.-S.; Von Geldern, T. N.; Bal, R.; Mantei, R. A.; Wu-Wong, R.; Chiou, W.; Dixon, D.; Opgenorth, T. J. Endothelin Antagonists, S.A.R. of 2,4-Diaryl-3-carboxypyrrolidine-1-acetamides. Book of Abstracts; 210th National Meeting of the American Chemical Society, Chicago, IL, 1995; American Chemical Society: Washington, DC, 1995; MEDI No. 030.
34. A) Antagonists. J. Med. Chem. 1995, 38, 1259-1263.
35. Fukuroda, T.; Kobayashi, M.; Ozaki, S.; Yano, M.; Miyauchi, T.; Onizuka, M.; Sugishita, Y.; Goto, K.; Nishikibe, M. Endothelin Receptor Subtypes in Human versus Rabbit Pulmonary Arteries. J. Appl. Physiol. 1994, 76, 1976-1982.
36. Main, B. G.; Rudge, D. A. Automated Chemical Synthesis. In International Symposium on Laboratory Automation and Robotics; Zymark Corp.: Hopkinton, MA, 1995; pp 425-434.
37. Magidson, O.; Menschikoff, G. Uber die Jodierung von α-Aminopyridin. (On the Iodination of α-Aminopyridine.) Ber. 1925, 58, 113-119.
38. Krchnak, V.; Arnold, Z. Novel Pyrimidine Derivatives, Reactions and Ultraviolet Spectra. Collect. Czech. Chem. Commun. 1975, 40, 1396-1402.
39. Sleek, E. A.; Brundage, P.; Fletcher, L. T. Pyridazine Derivatives. II. An improved Synthesis of 3-Aminopyridazine. J. Am. Chem. Soc. 1954, 76, 3225-3226.
40. Overend, W. G.; Wiggins, L. F. The Conversion of Sucrose into Pyridazine Derivatives. J. Chem. Soc. 1947, 239-244.
41. Takayashi, N. Synthesis of Pyridazine Derivatives VIII. Nucleophilic Substitution of 3,6-Dichloro-4-methylpyridazine. Pharm. Bull. 1957, 5, 229-234.
42. Barlin, G. B. Imidazo[1,2-b]pyridazines. I. Some 3-Alkoxy-6-halogeno-2-phenyl (and 4′-substituted phenyl)imidazo[1,2-b]-pyridazines and 3-Methoxy-2,6-diphenylimidazo[1,2-b]pyridazine. Aust. J. Chem. 1986, 39, 1803-1809.
43. Pitre, D.; Boveri, S.; Grabitz, E. B. Notiz uber 5-Methyl- und 6-Methyl-pyrazin-carbonsaure. (Note on 5-Methyl- and 6-Methylpyrazine carboxylic acid.) Chem. Ber. 1966, 99, 364-367.
44. Palamidessi, G.; Bernardi, L. On 2,5-Dichloropyrazine. J. Org. Chem. 1964, 29, 2491-2492.
45. Sato, N. Studies on Pyrazines, 8. An Improved Synthesis of 2-Amino-3,5-dibromo and 2-Amino-5-bromopyrazines. J. Heterocycl. Chem. 1982, 19, 673-674.
46. Sato, N. Studies on Pyrazines, 6. A Facile Separation Method for a Mixture of the Isomeric 2-Amino-3,5, and 6-methylpyrazines. J. Heterocycl. Chem. 1980, 17, 143-147.
47. Sato, N.; Takeuchi, R. Studies on Pyrazines; Part 20. A Simple Synthesis of 5-Substituted 2-Amino-3-cyanopyrazines: Useful Intermediates for Pteridine Synthesis. Synthesis 1990, 659-660.
48. Camerino, B.; Palamidessi, G. Derivati della Pirazina. - Nota 1. Aminopirazine. (Derivatives of Pyrazine - Note 1. Aminopyrazine.) Gazz. Chim. Ital. 1960, 90, 1807-1814.
49. Abignente, E.; Arena, F.; De Caprariis, P.; Nuzzetti, R.; Marmo, E.; Lampa, E.; Rosatti, F.; Ottavo, R. Research on Heterocyclic Compounds. X. Imidazo[1,2-α]pyrazine Derivatives - Synthesis and Antiinflammatory Activity. Farmaco Ed. Sci. 1981, 36, 61-80.
50. Nedospasov, A. A.; Sharina, I. G. The Synthesis of N(S)-Alkoxyethyl-Substituted Aminonaphthalenesulfonamides by Opening of the Aziridine Ring. Synlett 1992, 661-662.
51. Stein, P. D.; Hunt, J. T.; Murugesan, N. Sulfonamide Endothelin Antagonists. Eur. Pat. Appl. 558258, 1993.
52. Hirschberg, A.; Spoerri, P. E. The Synthesis and Properties of Iodopyrazines. J. Org. Chem. 1961, 26, 1907-1912.
53. Karmas, G.; Spoerri, P. E. The Preparation of Hydroxypyrazines and Derived Chloropyrazines. J. Am. Chem. Soc. 1952, 74, 1580-1584.
54. Coad, P.; Coad, R. A.; Clough, S.; Hyepock, J.; Salisbury, R.; Wilkins, C. Nucleophilic Substitution at the Pyridazine Ring Carbons. I. Synthesis of Iodopyridazines. J. Org. Chem. 1963, 28, 218-221.
55. Needham, M.; Gooding, C.; Hudson, K.; Antoniou, M.; Grosveld, F.; Hollis, M. LCR/MEL: A Versatile System for High-Level Expression of Heterologous Proteins in Erythroid Cells. Nucleic Acids Res. 1992, 20, 997-1003.