The preparation of (perfluoroalkyl)imidazoles as nonpeptide angiotensin II receptor antagonists
A series of (perfluoroalkyl)imidazoles have been prepared and are potent angiotensin II antagonists. One of these compounds, DuP 532, 4-pentafluoroethyl-2-propyl-1-[[2′-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]imidazole-5-carboxylic acid, is a selective antagonist of angiotensin II which causes a mark...
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| Published in | Bioorganic & medicinal chemistry letters Vol. 3; no. 5; pp. 895 - 898 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
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Elsevier Ltd
01.05.1993
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| Abstract | A series of (perfluoroalkyl)imidazoles have been prepared and are potent angiotensin II antagonists. One of these compounds, DuP 532, 4-pentafluoroethyl-2-propyl-1-[[2′-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]imidazole-5-carboxylic acid, is a selective antagonist of angiotensin II which causes a marked and long-lasting drop in blood pressure when administered orally to a renal hypertensive rat.
A series of (perfluoroalkyl)imidazoles have been prepared and are potent angiotensin II antagonists. One of these compounds, DuP 532, is a selective antagonist of angiotensin II which causes a marked and long-lasting drop in blood pressure when administered orally to a renal hypertensive rat. |
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| AbstractList | A series of (perfluoroalkyl)imidazoles have been prepared and are potent angiotensin II antagonists. One of these compounds, DuP 532, 4-pentafluoroethyl-2-propyl-1-[[2′-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]imidazole-5-carboxylic acid, is a selective antagonist of angiotensin II which causes a marked and long-lasting drop in blood pressure when administered orally to a renal hypertensive rat.
A series of (perfluoroalkyl)imidazoles have been prepared and are potent angiotensin II antagonists. One of these compounds, DuP 532, is a selective antagonist of angiotensin II which causes a marked and long-lasting drop in blood pressure when administered orally to a renal hypertensive rat. |
| Author | Chiu, Andrew T. Wong, Pancras C. Carini, David J. Wexler, Ruth R. Timmermans, Pieter B.M.W.M. Johnson, Alexander L. |
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| Cites_doi | 10.1038/288280a0 10.1021/ja00264a043 10.1016/0165-6147(87)90013-7 10.1016/0006-291X(91)91969-J 10.1097/00005344-198507004-00014 10.1021/ja00303a042 10.1021/jm00112a031 10.1126/science.191908 10.1002/med.2610120203 10.1021/jm00167a008 10.1021/jm00167a007 10.1038/ki.1990.228 10.1016/S0022-1139(00)82335-0 |
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| References | Heinze, Burton (BIB13) 1985; 29 BIB9 Ondetti, Rubin, Cushman (BIB4) 1977; 196 Duncia, Carini, Chiu, Johnson, Price, Wong, Wexler, Timmermans, Carini, Duncia, Aldrich, Chiu, Johnson, Pierce, Price, Santella, Wells, Wexler, Wong, Yoo, Timmermans, Carini, Duncia, Johnson, Chiu, Price, Wong, Timmermans, Duncia, Chiu, Carini, Gregory, Johnson, Price, Wells, Wong, Calabrese, Timmermans (BIB7) 1992; 12 Weimers, Burton, Burton, Weimers (BIB12) 1986; 108 Soffer, Sen, Xie, Liu, Wong, Timmermans, Cogan (BIB6) 1985; 7 Sealy, Laraugh (BIB1) 1990 Marsden, Brenner, Ballermann (BIB3) 1990 Vallotton (BIB2) 1987; 8 Wong, Price, Chiu, Duncia, Carini, Wexler, Johnson, Timmermans (BIB8) 1990; 255 Chiu, Carini, Duncia, Leung, McCall, Price, Wong, Smith, Wexler, Timmermans, Wong, Hart, Chiu, Herblin, Carini, Smith, Wexler, Timmermans (BIB11) 1991; 177 Patchett, Harris, Tristram, Wyvratt, Wu, Taub, Peterson, Ikeler, ten Broeke, Payne, Ondeyka, Thorsett, Greenlee, Lohr, Hoffsommer, Joshua, Ruyle, Rothrock, Aster, Maycock, Robinson, Hirschmann, Sweet, Ulm, Gross, Vassil, Stone (BIB5) 1980; 288 BIB10 Wong (10.1016/S0960-894X(00)80688-5_BIB11_2) 1991; 259 Weimers (10.1016/S0960-894X(00)80688-5_BIB12_1) 1986; 108 Vallotton (10.1016/S0960-894X(00)80688-5_BIB2) 1987; 8 Duncia (10.1016/S0960-894X(00)80688-5_BIB7_1) 1992; 12 Wong (10.1016/S0960-894X(00)80688-5_BIB8) 1990; 255 Patchett (10.1016/S0960-894X(00)80688-5_BIB5) 1980; 288 Sealy (10.1016/S0960-894X(00)80688-5_BIB1) 1990 Soffer (10.1016/S0960-894X(00)80688-5_BIB6_1) 1985; 7 Duncia (10.1016/S0960-894X(00)80688-5_BIB7_4) 1990; 33 Heinze (10.1016/S0960-894X(00)80688-5_BIB13) 1985; 29 Carini (10.1016/S0960-894X(00)80688-5_BIB7_3) 1990; 33 Marsden (10.1016/S0960-894X(00)80688-5_BIB3) 1990 Chiu (10.1016/S0960-894X(00)80688-5_BIB11_1) 1991; 177 Burton (10.1016/S0960-894X(00)80688-5_BIB12_2) 1985; 107 Carini (10.1016/S0960-894X(00)80688-5_BIB7_2) 1991; 34 Xie (10.1016/S0960-894X(00)80688-5_BIB6_2) 1990; 38 Ondetti (10.1016/S0960-894X(00)80688-5_BIB4) 1977; 196 |
| References_xml | – volume: 255 start-page: 211 year: 1990 ident: BIB8 publication-title: J. Pharmacol. Exp. Ther. contributor: fullname: Timmermans – volume: 7 start-page: S69 year: 1985 ident: BIB6 publication-title: J. Cardiovasc. Pharmacol. contributor: fullname: Cogan – start-page: 1247 year: 1990 ident: BIB3 publication-title: Hypertension: Pathophysiology, Diagnosis and Management contributor: fullname: Ballermann – ident: BIB9 – volume: 177 start-page: 209 year: 1991 ident: BIB11 publication-title: Biochem. Biophys. Res. Comm. contributor: fullname: Timmermans – start-page: 1287 year: 1990 ident: BIB1 publication-title: Hypertension: Pathophysiology, Diagnosis and Management contributor: fullname: Laraugh – volume: 12 start-page: 149 year: 1992 ident: BIB7 publication-title: Med. Res. Rev. contributor: fullname: Timmermans – ident: BIB10 – volume: 196 start-page: 441 year: 1977 ident: BIB4 publication-title: Science contributor: fullname: Cushman – volume: 108 start-page: 832 year: 1986 ident: BIB12 publication-title: J. Am. Chem. Soc. contributor: fullname: Weimers – volume: 29 start-page: 359 year: 1985 ident: BIB13 publication-title: J. Fluorine Chem. contributor: fullname: Burton – volume: 8 start-page: 69 year: 1987 ident: BIB2 publication-title: Trends Pharmacol. Sci. contributor: fullname: Vallotton – volume: 288 start-page: 280 year: 1980 ident: BIB5 publication-title: Nature contributor: fullname: Stone – volume: 288 start-page: 280 year: 1980 ident: 10.1016/S0960-894X(00)80688-5_BIB5 publication-title: Nature doi: 10.1038/288280a0 contributor: fullname: Patchett – start-page: 1247 year: 1990 ident: 10.1016/S0960-894X(00)80688-5_BIB3 contributor: fullname: Marsden – volume: 108 start-page: 832 year: 1986 ident: 10.1016/S0960-894X(00)80688-5_BIB12_1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00264a043 contributor: fullname: Weimers – start-page: 1287 year: 1990 ident: 10.1016/S0960-894X(00)80688-5_BIB1 contributor: fullname: Sealy – volume: 8 start-page: 69 year: 1987 ident: 10.1016/S0960-894X(00)80688-5_BIB2 publication-title: Trends Pharmacol. Sci. doi: 10.1016/0165-6147(87)90013-7 contributor: fullname: Vallotton – volume: 177 start-page: 209 year: 1991 ident: 10.1016/S0960-894X(00)80688-5_BIB11_1 publication-title: Biochem. Biophys. Res. Comm. doi: 10.1016/0006-291X(91)91969-J contributor: fullname: Chiu – volume: 7 start-page: S69 year: 1985 ident: 10.1016/S0960-894X(00)80688-5_BIB6_1 publication-title: J. Cardiovasc. Pharmacol. doi: 10.1097/00005344-198507004-00014 contributor: fullname: Soffer – volume: 259 start-page: 861 year: 1991 ident: 10.1016/S0960-894X(00)80688-5_BIB11_2 publication-title: J. Pharmacol. Exp. Ther. contributor: fullname: Wong – volume: 107 start-page: 5014 year: 1985 ident: 10.1016/S0960-894X(00)80688-5_BIB12_2 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00303a042 contributor: fullname: Burton – volume: 34 start-page: 2525 year: 1991 ident: 10.1016/S0960-894X(00)80688-5_BIB7_2 publication-title: J. Med. Chem. doi: 10.1021/jm00112a031 contributor: fullname: Carini – volume: 196 start-page: 441 year: 1977 ident: 10.1016/S0960-894X(00)80688-5_BIB4 publication-title: Science doi: 10.1126/science.191908 contributor: fullname: Ondetti – volume: 255 start-page: 211 year: 1990 ident: 10.1016/S0960-894X(00)80688-5_BIB8 publication-title: J. Pharmacol. Exp. Ther. contributor: fullname: Wong – volume: 12 start-page: 149 year: 1992 ident: 10.1016/S0960-894X(00)80688-5_BIB7_1 publication-title: Med. Res. Rev. doi: 10.1002/med.2610120203 contributor: fullname: Duncia – volume: 33 start-page: 1330 year: 1990 ident: 10.1016/S0960-894X(00)80688-5_BIB7_3 publication-title: J. Med. Chem. doi: 10.1021/jm00167a008 contributor: fullname: Carini – volume: 33 start-page: 1312 year: 1990 ident: 10.1016/S0960-894X(00)80688-5_BIB7_4 publication-title: J. Med. Chem. doi: 10.1021/jm00167a007 contributor: fullname: Duncia – volume: 38 start-page: 473 year: 1990 ident: 10.1016/S0960-894X(00)80688-5_BIB6_2 publication-title: Kidney Intl. doi: 10.1038/ki.1990.228 contributor: fullname: Xie – volume: 29 start-page: 359 year: 1985 ident: 10.1016/S0960-894X(00)80688-5_BIB13 publication-title: J. Fluorine Chem. doi: 10.1016/S0022-1139(00)82335-0 contributor: fullname: Heinze |
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