Recently discovered sulfonamide-, acyl sulfonamide- and carboxylic acid-based endothelin antagonists

IDrugs

Volumn 6, Issue 3, 2003, Pages 232-239

  Wu, Chengde ^a   Holland, George W ^a   Brock, Tommy A ^a   Dixon, Richard A F ^a  

^a TEXAS BIOTECHNOLOGY CORPORATION   (United States)

Author keywords

Acyl sulfonamide; Carboxylic acid; Endothelin; Sulfonamide

Indexed keywords

2 (1,3 BENZODIOXOL 5 YL) 6 ISOPROPYL 4 (4 METHOXYPHENYL) 2H CHROMENE 3 CARBOXYLIC ACID; 2 [[2 [[2 [[(HEXAHYDRO 1H AZEPIN 1 YL)CARBONYL]AMINO] 4 METHYLPENTANOYL]AMINO] 3 (1 METHYL 1H INDOL 3 YL)PROPIONYL]AMINO] 3 (2 PYRIDYL)PROPIONIC ACID; 3 (2 CARBOXYMETHOXY 4 METHOXYPHENYL) 1 (3,4 METHYLENEDIOXYPHENYL) 5 PROPOXY 2 INDANCARBOXYLIC ACID; ACYL SULFONAMIDE; ATRASENTAN; BIPHENYLSULFONAMIDE; BMS 193884; BMS 207940; BOSENTAN; CARBOXYLIC ACID; CYCLO(DEXTRO TRYPTOPHYL DEXTRO ASPARTYLPROLYL DEXTRO VALYLLEUCYL); DARUSENTAN; ENDOTHELIN 1; ENDOTHELIN A RECEPTOR; ENDOTHELIN A RECEPTOR ANTAGONIST; ENDOTHELIN B RECEPTOR; ENDOTHELIN B RECEPTOR ANTAGONIST; ENDOTHELIN RECEPTOR ANTAGONIST; L 749329; L 754142; N PYRIMIDINEBENZENESULFONAMIDE; N PYRIMIDINEPYRIDINESULFONAMIDE; N PYRIMIDINESTYRENESULFONAMIDE; SITAXSENTAN; SULFONAMIDE; TBC 3214; TBC 3711; TEZOSENTAN; THIOPHENESULFONAMIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG; YM 598;

CELL PROLIFERATION; CLINICAL TRIAL; DOSE RESPONSE; DRUG BIOAVAILABILITY; DRUG HALF LIFE; DRUG POTENCY; DRUG POTENTIATION; DRUG RECEPTOR BINDING; DRUG RESEARCH; DRUG SELECTIVITY; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TISSUE LEVEL; DRUG TOLERABILITY; HEART FAILURE; HUMAN; HYPERTENSION; KIDNEY DYSFUNCTION; METASTASIS; MITOGENICITY; NONHUMAN; PLASMA CLEARANCE; PROSTATE CANCER; PROTEIN EXPRESSION; PROTEIN FUNCTION; PROTEIN LOCALIZATION; PULMONARY HYPERTENSION; REVIEW; SMOOTH MUSCLE; STRUCTURE ACTIVITY RELATION; VASOCONSTRICTION; VASODILATATION;

ANIMALS; CARBOXYLIC ACIDS; HUMANS; RECEPTORS, ENDOTHELIN; SULFONAMIDES; VASCULAR DISEASES;

EID: 0038344687     PISSN: 13697056     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (49)

1. Clozel M, Breu V, Grey GA, Kalina B, Loffler BM, Burri K, Cassal JM, Hirth G, Muller M, Neidhart W et al: Pharmacological characterization of bosentan, a new potent orally active non-peptide endothelin receptor antagonist. J Pharmacol Exp Ther (1994) 270:228-235.
2. Wu C, Chan MF, Stavros F, Raju B, Okun I, Mong S, Keller KM, Brock T, Kogan TP, Dixon RA: Discovery of TBC11251, a potent, long acting, orally active endothelin receptor-A selective antagonist. J Med Chem (1997) 40:1690-1697.
3. Givertz MM, Colucci WS, LeJemtel TH, Gottlieb SS, Hare JM, Slawsky MT, Leier CV, Loh E, Nicklas JM, Lewis BE: Acute endothelin A receptor blockade causes selective pulmonary vasodilation in patients with chronic heart failure. Circulation (2000) 101:2922-2927.
4. Barst RJ, Rich S, Horn EM, McLaughlin VV, Kerstein D, Widlitz AC, McFarlin JD, Dixon RAF: Efficacy and safety of chronic treatment with the oral selective endothelin-A receptor blocker sitaxsentan in pulmonary arterial hypertension (PAH). 73rd American Heart Association Scientific Sessions, Atlanta, GA, USA (2000):Abs 2076.
5. Barst RJ, Rich S, Widlitz A, Horn EM, McLaughlin V, McFarlin J: Clinical efficacy of sitaxsentan, an endothelin-A receptor antagonist, in patients with pulmonary arterial hypertension: Open-label pilot study. Chest (2002) 121:1860-1868.
6. Calhoun DA, Renfroe K, Alper AB: Oral sitaxsentan, an endothelin-A selective receptor antagonist, reduces systemic blood pressure in patients with mild-to-moderate primary hypertension. 73rd American Heart Association Scientific Sessions, Atlanta, GA, USA (2000):Abs 2029.
7. Ooi H, Colucci WS, Givertz MM: Endothelin mediates increased pulmonary vascular tone in patients with heart failure: Demonstration by direct intrapulmonary infusion of sitaxsentan. Circulation (2002) 106:1618-1621.
8. ICOS-Texas Biotechnology LP: ICOS-Texas Biotechnology LP announces phase 2b/3 trial results for sitaxsentan. October 21. (2002)
9. A selective endothelin antagonist. J Med Chem (2001) 44:1211-1216.
10. A selective endothelin antagonist. 7th International Conference on Endothelin, Edinburgh, UK (2001):Abs P33.
11. A selective endothelin antagonist. 223rd ACS National Meeting, Orlando, FL, USA (2002):Abs MEDI-121. Description of the properties of TBC-3711.
12. Wu C, Decker ER, Holland GW, Brown PM, Stavros FD, Brock TA, Dixon RAF: Nonpeptide endothelin antagonists in clinical development. Drugs Today (2001) 37:441-453.
13. A receptor antagonist. 219th ACS National Meeting, San Francisco, CA, USA (2000):Abs MEDI-164.
14. A antagonists. J Med Chem (2000) 43:3111-3117. Data on BMS-193884 are reported.
15. Murugesan N, Gu Z, Stein PD, Spergel S, Bisaha S, Liu EC, Zhang R, Webb ML, Moreland S, Barrish JC: Biphenylsulfonamide endothelin receptor antagonists. Part 3: Structure-activity relationship of 4′-heterocyclic biphenylsulfonamides. Bioorg Med Chem Lett (2002) 12:517-520.
16. A selective antagonist. J Med Chem (2003) 46:125-137
17. Packer M: ENABLE results show pitfalls of endothelin antagonists in treating CHF. 51st Annual Scientific Session of the American College of Cardiology, Atlanta, GA, USA (2002). http://www.acc.org/2002ann_meeting/ssnews/enable.htm
18. Kalra P, Moon J, Coats A: Do results of the ENABLE (endothelin antagonist bosentan for lowering cardiac events in heart failure) study spell the end for non-selective endothelin antagonism in heart failure? Int J Cardiol (2002) 85:195-197.
19. Morimoto H, Shimadzu H, Kushiyama E, Kawanishi H, Hosaka T, Kawase Y, Yasuda K, Kikkawa K, Yamauchi-Kohno R, Yamada K: Potent and selective ET-A antagonists. 1. Syntheses and structure-activity relationships of N-(6-(2-(aryloxy)ethoxy)-4-pyrimidinyl)sulfonamide derivatives. J Med Chem (2001) 44:3355-3368.
20. Morimoto H, Ohashi N, Shimadzu H, Kushiyama E, Kawanishi H, Hosaka T, Kawase Y, Yasuda K, Kikkawa K, Yamauchi-Kohno R, Yamad K: Potent and selective ET-A antagonists. 2. Discovery and evaluation of potent and water soluble N-(6-(2-(aryloxy)ethoxy)-4-pyrimidinyl)sulfonamide derivatives. J Med Chem (2001) 44:3369-3377.
21. Morimoto H, Shimadzu H, Hosaka T, Kawase Y, Yasuda K, Kikkawa K, Yamauchi-Kohno R, Yamada K: Modifications and structure-activity relationships at the 2-position of 4-sulfonamidopyrimidine derivatives as potent endothelin antagonists. Bioorg Med Chem Lett (2002) 12:81-84.
22. Harada H, Kazami J, Watanuki S, Tsuzuki R, Sudoh K, Fujimori A, Tanaka A, Tsukamoto S, Yanagisawa I: Ethenesulfonamide derivatives, a novel class of orally active endothelin-A receptor antagonists. Chem Pharm Bull (2001) 49:606-612.
23. Harada H, Kazami J, Watanuki S, Tsuzuki R, Sudoh K, Fujimori A, Sanagi M, Orita M, Nakahara H, Shimaya J, Tsukamoto S et al: Ethenesulfonamide and ethanesulfonamide derivatives, a novel class of orally active endothelin-A receptor antagonists. Bioorg Med Chem (2001) 9:2955-2968.
24. Harada H, Kazami J, Watanuki S, Tsuzuki R, Sudoh K, Fujimori A, Tokunaga T, Tanaka A, Tsukamoto S, Yanagisawa I: Synthesis and structure-activity relationships in a series of ethenesulfonamide derivatives, a novel class of endothelin receptor antagonists. Chem Pharm Bull (2001) 49:1593-1603.
25. Genentech Inc: Phase III clinical trial of Veletri for the treatment of acute heart failure symptoms does not meet primary efficacy objective. Press Release (2001) April 20.
26. Williams DL Jr, Murphy KL, Nolan NA, O'Brien JA, Pettibone DJ, Kivlighn SD, Krause SM, Lis EV Jr, Zingaro GJ, Gabel RA et al: Pharmacology of L-754,142, a highly potent, orally active, nonpeptidyl endothelin antagonist. J Pharmacol Exp Ther (1995) 275: 1518-1526.
27. A antagonists. Bioorg Med Chem Lett (2002) 12:125-128.
28. Elliott JD, Lago MA, Cousins RD, Gao A, Leber JD, Erhard KF, Nambi P, Elshourbagy NA, Kumar C, Lee JA, Bean JW et al: 1,3-Diarylindan-2-carboxylic acids, potent and selective non-peptide endothelin receptor antagonists. J Med Chem (1994) 37:1553-1557.
29. Kukkola PJ, Bilci NA, Ikler T, Savage P, Shetty SS, DelGrande D, Jeng AY: Isoindolines: A new series of potent and selective endothelin-A receptor antagonists. Bioorg Med Chem Lett (2001) 11:1737-1740.
30. A selectivity. Potency- and solubility-enhancing modifications. J Med Chem (1992) 35:2139-2142.
31. Aramori I, Hisataka N, Shoubo M, Sogabe K, Nakamura K, Kojo H, Notsu Y, Ono T, Nakanishi S: Subtype selectivity of a novel endothelin antagonist, FR139317, for the two endothelin receptors in transfected Chinese hamster ovary cells. Mol Pharmacol (1993) 43:127-131.
32. A receptor antagonist. J Pharmacol Exp Ther (1993) 264:1040-1046.
33. Morimoto H, Fukushima C, Yamauchi R, Hosino T, Kikkawa K, Yasuda K, Yamada K: Design, syntheses, and structure-activity relationships of indan derivatives as endothelin antagonists; New lead generation of non-peptidic antagonist from peptidic leads. Bioorg Med Chem (2001) 9:255-268.
34. A selective endothelin receptor antagonists. 1. Discovery of A-127722. J Med Chem (1996) 39:1039-1048.
35. Abbott Laboratories: Data suggests Abbott Laboratories' Atrasentan (ABT-627) inhibits progression of bone metastases in end-stage prostate cancer - First endothelin-A receptor antagonist under evaluation in oncology. Press Release (2001) May 13.
36. A antagonists. J Med Chem (2001) 44:3978-3984.
37. Riechers H, Albrecht HP, Amberg W, Baumann E, Bernard H, Böhm HJ, Klinge D, Kling A, Müller S, Raschack M, Unger L et al: Discovery and optimization of a novel class of orally active nonpeptidic endothelin-A receptor antagonists. J Med Chem (1996) 39:2123-2128.
38. A Receptor Blockade Trial). 73rd American Heart Association Scientific Sessions, Atlanta, GA, USA (2000): Abs 2876.
39. A antagonism. J Med Chem (2002) 45:2041-2055.
40. Texas Biotechnology Corp (Wu C, Holland GW, Blok N): Sulfonamides and derivatives thereof that modulate the activity of endothelin. WO-00149685 (2001).
41. Bristol Myers Squibb Co (Murugesan N, Tellew JE, Macor JE, Gu Z): Biphenyl sulfonamides as dual angiotensin endothelin receptor antagonists. WO-00144239 (2001).
42. Pfizer Inc (Banks BJ, Chubb NA, Eshelby JJ, Schulz DJ): Pyrazoles and their use as endothelin antagonists. EP-01072597 (2001).
43. Actelion Pharmaceuticals Ltd (Bolli M, Boss C, Clozel M, Fischli W): Bis-sulfonamides. WO-00117976 (2001).
44. Actelion Pharmaceuticals Ltd (Boss C, Bolli M, Clozel M, Fischli W, Weller T): Novel arylethene-sulfonamides. WO-00208200 (2002).
45. Yamanouchi Pharmaceutical Co Ltd (Yuyama H, Fujimori A, Sanagi M, Harada H, Koakutsu A, Mori M, Yamamoto N): Remedies for endothelin-induced diseases. WO-00160370 (2001).
46. Actelion Pharmaceuticals Ltd (Bolli M, Boss C, Clozel M, Fischli W, Weller T): Pyrimidine-sulfonamides having endothelin-antagonist activity. WO-00181335 (2001).
47. Actelion Pharmaceuticals Ltd (Boss C, Bolli M, Clozel M, Fischli W, Weller T): Substituted sulfonylaminopyrimidines. WO-00181338 (2001).
48. Actelion Pharmaceuticals Ltd (Bolli M, Boss C, Clozel M, Fischli W): Butyne diol derivatives. WO-00146156 (2001).
49. BASF AG (Amberg W, Kettschau G): Novel carbamates and carbamides, production and use thereof as endothelin receptor antagonists. WO-00190079 (2001).