Nonpeptide angiotensin II receptor antagonists: Synthesis, biological activities, and structure - Activity relationships of imidazole-5-carboxylic acids bearing alkyl, alkenyl, and hydroxyalkyl substituents at the 4-position and their related compounds

Journal of Medicinal Chemistry

Volumn 39, Issue 1, 1996, Pages 323-338

  Yanagisawa, Hiroaki ^a   Amemiya, Yoshiya ^a   Kanazaki, Takuro ^a   Shimoji, Yasuo ^a   Fujimoto, Koichi ^a   Kitahara, Yoshiko ^a   Sada, Toshio ^a   Mizuno, Makoto ^a   Ikeda, Masahiro ^a   Miyamoto, Shuichi ^a   Furukawa, Youji ^a   Koike, Hiroyuki ^a  

^a DAIICHI SANKYO CO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 BUTYL 4 CHLORO 1 [[2' (1H TETRAZOL 5 YL) 4 BIPHENYLYL]METHYL] 5 IMIDAZOLECARBOXYLIC ACID; ANGIOTENSIN RECEPTOR ANTAGONIST; CARBOXYLIC ACID DERIVATIVE; LOSARTAN POTASSIUM; OLMESARTAN; UNCLASSIFIED DRUG;

ADRENAL CORTEX; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CATTLE; DRUG ACTIVITY; DRUG POTENCY; DRUG SYNTHESIS; INTRAVENOUS DRUG ADMINISTRATION; MALE; NONHUMAN; ORAL DRUG ADMINISTRATION; PRESSOR RESPONSE; RAT; RECEPTOR AFFINITY; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ACETYLATION; ADRENAL CORTEX; AMINO ACID SEQUENCE; ANGIOTENSIN II; ANIMALS; ANTIHYPERTENSIVE AGENTS; BIOLOGICAL AVAILABILITY; CATTLE; IMIDAZOLES; KINETICS; MALE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; RATS; RATS, WISTAR; RECEPTORS, ANGIOTENSIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0030049822     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm950450f     Document Type: Article

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49. After completing our study, prodrugs of AII receptor antagonists have been reported; see: (a) Zydowsky, T. M.; Winn, M.; De, B.; Altenbach, R. J.; Rosenberg, S. H.; Kerkman, D. J.; DeBernardis, J. F.; Buckner, S. A.; Lee, J.; Brune, M.; Morse, P.; Warner, R. B.; Marsh, K.; Srivatsa, G. S.; Bauch, J. 4-Aminopyrimidine-5-carboxylic Acid Prodrugs as Angiotensin II Antagonists. Presented at the 204th National Meeting of the American Chemical Society, Washington, DC, August 23-28, 1992; MEDI 27. (b) Kubo, K.; Kohara, Y.; Yoshimura, Y.; Inada, Y.; Shiboura, Y.; Furukawa, Y.; Kato, T.; Nishikawa, K.; Naka, T. Nonpeptide Angiotensin II Receptor Antagonists. Synthesis and Biological Activity of Potential Prodrugs of Benzimidazole-7-carboxylic Acids. J. Med. Chem. 1993, 36, 2343-2349. (c) Kim, K. S.; Qian, L.; Bird, J. E.; Dickinson, K. E. J.; Moreland, S.; Schaeffer, T. R.; Waldron, T. L.; Delaney, C. L.; Weller, H. N.; Miller, A. V. Quinoxaline N-Oxide Containing Potent Angiotensin II Receptor Antagonists: Synthesis, Biological Properties, and Structure-Activity Relationships. J. Med. Chem. 1993, 36, 2335-2342. (d) Middlemiss, D.; Watson, S. P.; Ross, B. C.; Dowle, M. D.; Scopes, D. I. C.; Montana, J. G.; Stah, P.; Hirst, G. C.; Panchal, T. A.; Paton, J. M. S.; Pass, M.; Hubbard, T.; Hamblett, J.; Cardwell, K. S.; Jack, T. I.; Stuart, G.; Coote, S.; Bradshaw, J.; Drew, G. M.; Hilditch, A.; Clark, K. L.; Robertson, M. J.; Bayliss, M. K.; Donnelly, M.; Palmer, E.; Manchee, G. R. M. Benzofuran Based Angiotensin II Antagonists Related to GR117289: Enhancement of potency in vitro and Oral Activity. Bioorg. Med. Chem. Lett. 1993, 3, 589-594. (e) Carini, D. J.; Ardecky, R. J.; Ensinger, C. L.; Pruitt, J. R.; Wexler, R. R.; Wong, P. C.; Huang, S.-M.; Aungst, B. J.; Timmermans, P. B. M. W. M. Nonpeptide Angiotensin II Receptor Antagonists: The Discovery of DMP581 and DMP811. Bioorg. Med. Chem. Lett. 1994, 4, 63-68. (f) Ryono, D. E.; Poss, M. A.; Bird, J. E.; Buote, J.; Chong, S.; Dejneka, T.; Dickinson, K. E. J.; Gu, Z.; Mathers, P.; Moreland, S.; Morrison, R. A.; Petrillo, E. W.; Powell, J. R.; Shaeffer, T.; Spitzmiller, E. R.; White, R. E. Orally Active Prodrugs of Quinoline-4-carboxylic Acid Angiotensin II Receptor Antagonists. Bioorg. Med. Chem. Lett. 1994, 4, 201-206.
50. After completing our study, prodrugs of AII receptor antagonists have been reported; see: (a) Zydowsky, T. M.; Winn, M.; De, B.; Altenbach, R. J.; Rosenberg, S. H.; Kerkman, D. J.; DeBernardis, J. F.; Buckner, S. A.; Lee, J.; Brune, M.; Morse, P.; Warner, R. B.; Marsh, K.; Srivatsa, G. S.; Bauch, J. 4-Aminopyrimidine-5-carboxylic Acid Prodrugs as Angiotensin II Antagonists. Presented at the 204th National Meeting of the American Chemical Society, Washington, DC, August 23-28, 1992; MEDI 27. (b) Kubo, K.; Kohara, Y.; Yoshimura, Y.; Inada, Y.; Shiboura, Y.; Furukawa, Y.; Kato, T.; Nishikawa, K.; Naka, T. Nonpeptide Angiotensin II Receptor Antagonists. Synthesis and Biological Activity of Potential Prodrugs of Benzimidazole-7-carboxylic Acids. J. Med. Chem. 1993, 36, 2343-2349. (c) Kim, K. S.; Qian, L.; Bird, J. E.; Dickinson, K. E. J.; Moreland, S.; Schaeffer, T. R.; Waldron, T. L.; Delaney, C. L.; Weller, H. N.; Miller, A. V. Quinoxaline N-Oxide Containing Potent Angiotensin II Receptor Antagonists: Synthesis, Biological Properties, and Structure-Activity Relationships. J. Med. Chem. 1993, 36, 2335-2342. (d) Middlemiss, D.; Watson, S. P.; Ross, B. C.; Dowle, M. D.; Scopes, D. I. C.; Montana, J. G.; Stah, P.; Hirst, G. C.; Panchal, T. A.; Paton, J. M. S.; Pass, M.; Hubbard, T.; Hamblett, J.; Cardwell, K. S.; Jack, T. I.; Stuart, G.; Coote, S.; Bradshaw, J.; Drew, G. M.; Hilditch, A.; Clark, K. L.; Robertson, M. J.; Bayliss, M. K.; Donnelly, M.; Palmer, E.; Manchee, G. R. M. Benzofuran Based Angiotensin II Antagonists Related to GR117289: Enhancement of potency in vitro and Oral Activity. Bioorg. Med. Chem. Lett. 1993, 3, 589-594. (e) Carini, D. J.; Ardecky, R. J.; Ensinger, C. L.; Pruitt, J. R.; Wexler, R. R.; Wong, P. C.; Huang, S.-M.; Aungst, B. J.; Timmermans, P. B. M. W. M. Nonpeptide Angiotensin II Receptor Antagonists: The Discovery of DMP581 and DMP811. Bioorg. Med. Chem. Lett. 1994, 4, 63-68. (f) Ryono, D. E.; Poss, M. A.; Bird, J. E.; Buote, J.; Chong, S.; Dejneka, T.; Dickinson, K. E. J.; Gu, Z.; Mathers, P.; Moreland, S.; Morrison, R. A.; Petrillo, E. W.; Powell, J. R.; Shaeffer, T.; Spitzmiller, E. R.; White, R. E. Orally Active Prodrugs of Quinoline-4-carboxylic Acid Angiotensin II Receptor Antagonists. Bioorg. Med. Chem. Lett. 1994, 4, 201-206.
51. After completing our study, prodrugs of AII receptor antagonists have been reported; see: (a) Zydowsky, T. M.; Winn, M.; De, B.; Altenbach, R. J.; Rosenberg, S. H.; Kerkman, D. J.; DeBernardis, J. F.; Buckner, S. A.; Lee, J.; Brune, M.; Morse, P.; Warner, R. B.; Marsh, K.; Srivatsa, G. S.; Bauch, J. 4-Aminopyrimidine-5-carboxylic Acid Prodrugs as Angiotensin II Antagonists. Presented at the 204th National Meeting of the American Chemical Society, Washington, DC, August 23-28, 1992; MEDI 27. (b) Kubo, K.; Kohara, Y.; Yoshimura, Y.; Inada, Y.; Shiboura, Y.; Furukawa, Y.; Kato, T.; Nishikawa, K.; Naka, T. Nonpeptide Angiotensin II Receptor Antagonists. Synthesis and Biological Activity of Potential Prodrugs of Benzimidazole-7-carboxylic Acids. J. Med. Chem. 1993, 36, 2343-2349. (c) Kim, K. S.; Qian, L.; Bird, J. E.; Dickinson, K. E. J.; Moreland, S.; Schaeffer, T. R.; Waldron, T. L.; Delaney, C. L.; Weller, H. N.; Miller, A. V. Quinoxaline N-Oxide Containing Potent Angiotensin II Receptor Antagonists: Synthesis, Biological Properties, and Structure-Activity Relationships. J. Med. Chem. 1993, 36, 2335-2342. (d) Middlemiss, D.; Watson, S. P.; Ross, B. C.; Dowle, M. D.; Scopes, D. I. C.; Montana, J. G.; Stah, P.; Hirst, G. C.; Panchal, T. A.; Paton, J. M. S.; Pass, M.; Hubbard, T.; Hamblett, J.; Cardwell, K. S.; Jack, T. I.; Stuart, G.; Coote, S.; Bradshaw, J.; Drew, G. M.; Hilditch, A.; Clark, K. L.; Robertson, M. J.; Bayliss, M. K.; Donnelly, M.; Palmer, E.; Manchee, G. R. M. Benzofuran Based Angiotensin II Antagonists Related to GR117289: Enhancement of potency in vitro and Oral Activity. Bioorg. Med. Chem. Lett. 1993, 3, 589-594. (e) Carini, D. J.; Ardecky, R. J.; Ensinger, C. L.; Pruitt, J. R.; Wexler, R. R.; Wong, P. C.; Huang, S.-M.; Aungst, B. J.; Timmermans, P. B. M. W. M. Nonpeptide Angiotensin II Receptor Antagonists: The Discovery of DMP581 and DMP811. Bioorg. Med. Chem. Lett. 1994, 4, 63-68. (f) Ryono, D. E.; Poss, M. A.; Bird, J. E.; Buote, J.; Chong, S.; Dejneka, T.; Dickinson, K. E. J.; Gu, Z.; Mathers, P.; Moreland, S.; Morrison, R. A.; Petrillo, E. W.; Powell, J. R.; Shaeffer, T.; Spitzmiller, E. R.; White, R. E. Orally Active Prodrugs of Quinoline-4-carboxylic Acid Angiotensin II Receptor Antagonists. Bioorg. Med. Chem. Lett. 1994, 4, 201-206.
52. After completing our study, prodrugs of AII receptor antagonists have been reported; see: (a) Zydowsky, T. M.; Winn, M.; De, B.; Altenbach, R. J.; Rosenberg, S. H.; Kerkman, D. J.; DeBernardis, J. F.; Buckner, S. A.; Lee, J.; Brune, M.; Morse, P.; Warner, R. B.; Marsh, K.; Srivatsa, G. S.; Bauch, J. 4-Aminopyrimidine-5-carboxylic Acid Prodrugs as Angiotensin II Antagonists. Presented at the 204th National Meeting of the American Chemical Society, Washington, DC, August 23-28, 1992; MEDI 27. (b) Kubo, K.; Kohara, Y.; Yoshimura, Y.; Inada, Y.; Shiboura, Y.; Furukawa, Y.; Kato, T.; Nishikawa, K.; Naka, T. Nonpeptide Angiotensin II Receptor Antagonists. Synthesis and Biological Activity of Potential Prodrugs of Benzimidazole-7-carboxylic Acids. J. Med. Chem. 1993, 36, 2343-2349. (c) Kim, K. S.; Qian, L.; Bird, J. E.; Dickinson, K. E. J.; Moreland, S.; Schaeffer, T. R.; Waldron, T. L.; Delaney, C. L.; Weller, H. N.; Miller, A. V. Quinoxaline N-Oxide Containing Potent Angiotensin II Receptor Antagonists: Synthesis, Biological Properties, and Structure-Activity Relationships. J. Med. Chem. 1993, 36, 2335-2342. (d) Middlemiss, D.; Watson, S. P.; Ross, B. C.; Dowle, M. D.; Scopes, D. I. C.; Montana, J. G.; Stah, P.; Hirst, G. C.; Panchal, T. A.; Paton, J. M. S.; Pass, M.; Hubbard, T.; Hamblett, J.; Cardwell, K. S.; Jack, T. I.; Stuart, G.; Coote, S.; Bradshaw, J.; Drew, G. M.; Hilditch, A.; Clark, K. L.; Robertson, M. J.; Bayliss, M. K.; Donnelly, M.; Palmer, E.; Manchee, G. R. M. Benzofuran Based Angiotensin II Antagonists Related to GR117289: Enhancement of potency in vitro and Oral Activity. Bioorg. Med. Chem. Lett. 1993, 3, 589-594. (e) Carini, D. J.; Ardecky, R. J.; Ensinger, C. L.; Pruitt, J. R.; Wexler, R. R.; Wong, P. C.; Huang, S.-M.; Aungst, B. J.; Timmermans, P. B. M. W. M. Nonpeptide Angiotensin II Receptor Antagonists: The Discovery of DMP581 and DMP811. Bioorg. Med. Chem. Lett. 1994, 4, 63-68. (f) Ryono, D. E.; Poss, M. A.; Bird, J. E.; Buote, J.; Chong, S.; Dejneka, T.; Dickinson, K. E. J.; Gu, Z.; Mathers, P.; Moreland, S.; Morrison, R. A.; Petrillo, E. W.; Powell, J. R.; Shaeffer, T.; Spitzmiller, E. R.; White, R. E. Orally Active Prodrugs of Quinoline-4-carboxylic Acid Angiotensin II Receptor Antagonists. Bioorg. Med. Chem. Lett. 1994, 4, 201-206.
53. After completing our study, prodrugs of AII receptor antagonists have been reported; see: (a) Zydowsky, T. M.; Winn, M.; De, B.; Altenbach, R. J.; Rosenberg, S. H.; Kerkman, D. J.; DeBernardis, J. F.; Buckner, S. A.; Lee, J.; Brune, M.; Morse, P.; Warner, R. B.; Marsh, K.; Srivatsa, G. S.; Bauch, J. 4-Aminopyrimidine-5-carboxylic Acid Prodrugs as Angiotensin II Antagonists. Presented at the 204th National Meeting of the American Chemical Society, Washington, DC, August 23-28, 1992; MEDI 27. (b) Kubo, K.; Kohara, Y.; Yoshimura, Y.; Inada, Y.; Shiboura, Y.; Furukawa, Y.; Kato, T.; Nishikawa, K.; Naka, T. Nonpeptide Angiotensin II Receptor Antagonists. Synthesis and Biological Activity of Potential Prodrugs of Benzimidazole-7-carboxylic Acids. J. Med. Chem. 1993, 36, 2343-2349. (c) Kim, K. S.; Qian, L.; Bird, J. E.; Dickinson, K. E. J.; Moreland, S.; Schaeffer, T. R.; Waldron, T. L.; Delaney, C. L.; Weller, H. N.; Miller, A. V. Quinoxaline N-Oxide Containing Potent Angiotensin II Receptor Antagonists: Synthesis, Biological Properties, and Structure-Activity Relationships. J. Med. Chem. 1993, 36, 2335-2342. (d) Middlemiss, D.; Watson, S. P.; Ross, B. C.; Dowle, M. D.; Scopes, D. I. C.; Montana, J. G.; Stah, P.; Hirst, G. C.; Panchal, T. A.; Paton, J. M. S.; Pass, M.; Hubbard, T.; Hamblett, J.; Cardwell, K. S.; Jack, T. I.; Stuart, G.; Coote, S.; Bradshaw, J.; Drew, G. M.; Hilditch, A.; Clark, K. L.; Robertson, M. J.; Bayliss, M. K.; Donnelly, M.; Palmer, E.; Manchee, G. R. M. Benzofuran Based Angiotensin II Antagonists Related to GR117289: Enhancement of potency in vitro and Oral Activity. Bioorg. Med. Chem. Lett. 1993, 3, 589-594. (e) Carini, D. J.; Ardecky, R. J.; Ensinger, C. L.; Pruitt, J. R.; Wexler, R. R.; Wong, P. C.; Huang, S.-M.; Aungst, B. J.; Timmermans, P. B. M. W. M. Nonpeptide Angiotensin II Receptor Antagonists: The Discovery of DMP581 and DMP811. Bioorg. Med. Chem. Lett. 1994, 4, 63-68. (f) Ryono, D. E.; Poss, M. A.; Bird, J. E.; Buote, J.; Chong, S.; Dejneka, T.; Dickinson, K. E. J.; Gu, Z.; Mathers, P.; Moreland, S.; Morrison, R. A.; Petrillo, E. W.; Powell, J. R.; Shaeffer, T.; Spitzmiller, E. R.; White, R. E. Orally Active Prodrugs of Quinoline-4-carboxylic Acid Angiotensin II Receptor Antagonists. Bioorg. Med. Chem. Lett. 1994, 4, 201-206.
54. After completing our study, prodrugs of AII receptor antagonists have been reported; see: (a) Zydowsky, T. M.; Winn, M.; De, B.; Altenbach, R. J.; Rosenberg, S. H.; Kerkman, D. J.; DeBernardis, J. F.; Buckner, S. A.; Lee, J.; Brune, M.; Morse, P.; Warner, R. B.; Marsh, K.; Srivatsa, G. S.; Bauch, J. 4-Aminopyrimidine-5-carboxylic Acid Prodrugs as Angiotensin II Antagonists. Presented at the 204th National Meeting of the American Chemical Society, Washington, DC, August 23-28, 1992; MEDI 27. (b) Kubo, K.; Kohara, Y.; Yoshimura, Y.; Inada, Y.; Shiboura, Y.; Furukawa, Y.; Kato, T.; Nishikawa, K.; Naka, T. Nonpeptide Angiotensin II Receptor Antagonists. Synthesis and Biological Activity of Potential Prodrugs of Benzimidazole-7-carboxylic Acids. J. Med. Chem. 1993, 36, 2343-2349. (c) Kim, K. S.; Qian, L.; Bird, J. E.; Dickinson, K. E. J.; Moreland, S.; Schaeffer, T. R.; Waldron, T. L.; Delaney, C. L.; Weller, H. N.; Miller, A. V. Quinoxaline N-Oxide Containing Potent Angiotensin II Receptor Antagonists: Synthesis, Biological Properties, and Structure-Activity Relationships. J. Med. Chem. 1993, 36, 2335-2342. (d) Middlemiss, D.; Watson, S. P.; Ross, B. C.; Dowle, M. D.; Scopes, D. I. C.; Montana, J. G.; Stah, P.; Hirst, G. C.; Panchal, T. A.; Paton, J. M. S.; Pass, M.; Hubbard, T.; Hamblett, J.; Cardwell, K. S.; Jack, T. I.; Stuart, G.; Coote, S.; Bradshaw, J.; Drew, G. M.; Hilditch, A.; Clark, K. L.; Robertson, M. J.; Bayliss, M. K.; Donnelly, M.; Palmer, E.; Manchee, G. R. M. Benzofuran Based Angiotensin II Antagonists Related to GR117289: Enhancement of potency in vitro and Oral Activity. Bioorg. Med. Chem. Lett. 1993, 3, 589-594. (e) Carini, D. J.; Ardecky, R. J.; Ensinger, C. L.; Pruitt, J. R.; Wexler, R. R.; Wong, P. C.; Huang, S.-M.; Aungst, B. J.; Timmermans, P. B. M. W. M. Nonpeptide Angiotensin II Receptor Antagonists: The Discovery of DMP581 and DMP811. Bioorg. Med. Chem. Lett. 1994, 4, 63-68. (f) Ryono, D. E.; Poss, M. A.; Bird, J. E.; Buote, J.; Chong, S.; Dejneka, T.; Dickinson, K. E. J.; Gu, Z.; Mathers, P.; Moreland, S.; Morrison, R. A.; Petrillo, E. W.; Powell, J. R.; Shaeffer, T.; Spitzmiller, E. R.; White, R. E. Orally Active Prodrugs of Quinoline-4-carboxylic Acid Angiotensin II Receptor Antagonists. Bioorg. Med. Chem. Lett. 1994, 4, 201-206.
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