Discovery of 1,5-benzodiazepines with peripheral cholecystokinin (CCK-A) receptor agonist activity (II): Optimization of the C3 amino substituent

Journal of Medicinal Chemistry

Volumn 39, Issue 26, 1996, Pages 5236-5245

  Hirst, Gavin C ^a   Aquino, Christopher ^a   Birkemo, Lawrence ^a   Croom, Dallas K ^a   Dezube, Milana ^b   Dougherty Jr , Robert W ^a   Ervin, Gregory N ^a   Grizzle, Mary K ^a   Henke, Brad ^a   James, Michael K ^a   Johnson, Michael F ^a   Momtahen, Tanya ^a   Queen, Kennedy L ^a   Sherrill, Ronald G ^a   Szewczyk, Jerzy ^a   Willson, Timothy M ^a   Sugg, Elizabeth E ^a  

^a GLAXOSMITHKLINE   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

BENZODIAZEPINE DERIVATIVE; BENZOIC ACID DERIVATIVE; CHOLECYSTOKININ RECEPTOR STIMULATING AGENT; GW 7854; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; GALLBLADDER CONTRACTION; GUINEA PIG; HUMAN; NONHUMAN; OBESITY; RECEPTOR AFFINITY; SATIETY; STRUCTURE ACTIVITY RELATION;

ANIMALS; APPETITE DEPRESSANTS; BENZODIAZEPINES; CALCIUM; CHO CELLS; CRICETINAE; FEEDING BEHAVIOR; GUINEA PIGS; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MICE; RATS; RECEPTOR, CHOLECYSTOKININ A; RECEPTORS, CHOLECYSTOKININ; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT;

EID: 0030447089     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9601664     Document Type: Article

References (28)

1. Crawley, J. N.; Corwin, R. L. Biological Actions of Cholecystokinin. Peptides 1994, 15, 731-755.
2. Larson, L.-I.; Rehfeld, J. F. Localisation and Molecular Heterogeneity of Cholocystokinin in the Central and Peripheral Nervous System. Brain Res. 1979, 165, 201-18.
3. Rehfeld, J. F.; Golterman, N. R.; Larson, L.-I.; Emson, P. M.; Lee, C. M. Gastrin and Cholecystokinin in Central and Perhipheral Neurons. Fed. Proc. 1979, 38, 2325.
4. Reeve, J. R. Jr.; Eysselein, V.; Walsh, J. H.; Ben Avram, C. M.; Shively, J. E. New Molecular Forms of Cholecystokinin. Microsequence Analysis of Forms Previously Characterized by Chromatographic Methods. J. Biol. Chem. 1986, 261, 16392-7.
5. Liddle, R. A.; Green, G. M.; Conrad, C. K.; Williams, J. A. Proteins But Not Amino Acids, Carbohydrates or Fats Stimulate Cholecystokinin Secretion in the Rat. Am. J Physiology 1986, 251, G243-248.
6. Silvente-Poirot, S.; Dufresne, M.; Vaysse, N.; Fourmy, D. The Peripheral Cholecystokinin Receptors Eur. J. Biochem. 1993, 215, 513-529.
7. Makovec, F. CCK-B/Gastrin Receptor Antagonists Drugs Future 1993, 18, 919-931.
8. Wank, S. A. Cholecystokinin Receptors Am. J. Physiol. 1995, G628-G646.
9. Kissileff, H. R.; Pi-Sunyer, F. X.; Thornton, J.; Smith, G. P. C-Terminal Octapeptide of Cholecystokinin Decreases Food Intake in Man. Am. J. Clin. Nutr. 1981, 34, 154-160.
10. Pi-Sunyer, X.; Kissileff, H. R.; Thornton, J.; Smith, G. P. C-Terminal Octapeptide of Cholecystokinin Decreases Food Intake in Obese Men. Physiol. Behav. 1982, 29, 627-630.
11. Sitzmann, J. V.; Pitt, H. A.; Steinborn, P. A.; Pasha, Z. R.; Sanders, R. C. Cholecystokinin Prevents Parenteral Nutrition Induced Biliary Sludge in Humans Surg. Gynacol. Obstetrics 1990, 170, 25-31.
12. Dourish, C. T.; Ruckert, A. C.; Tattersall, F. D.; Iversen, S. D. Evidence That Decreased Feeding Induced by Systemic Injection of Cholecystokinin is Mediated by CCK-A Receptors. Eur. J. Pharmacol. 1989, 173, 233-234.
13. Silverstone, T. In Obesity: Theory and Therapy Stunkard, A. J., Wadden, T. A., Eds.; Raven Press, Ltd.: New York, 1993; pp 275-283.
14. Aquino, C. J.; Armour, D. R.; Berman, J. M.; Birkemo, L. S.; Carr, R. A. E.; Croom, D. K.; Dezube, M.; Dougherty, R. W.; Ervin, G. N.; Grizzle, M. K.; Head, J. E.; Hirst, G. C.; James, M. K.; Johnson, M. F.; Long, J. E.; Miller, L. J.; Queen, K. L.; Rimele, T. J.; Smith, D. N.; Sugg, E. E. Discovery of 1,5-Benzodiazepines with Peripheral Cholecystokinin (CCK-A) Receptor Agonist Activity I. Optimization of the Agonist "Trigger". J. Med. Chem. 1996, 39, 562-569.
15. Bock, M. G.; DiPardo, R. M.; Evans, B. E.; Rittle, K. E.; Whitter, W. L.; Garsky, V. M.; Gilbert, K. F.; Leighton, J. L.; Carson, K. L.; Mellin, E. C.; Veber, D. F.; Chang, R. S. L.; Lotti, V. J.; Freeman, S. B.; Amith, A. J.; Patel, S.; Anderson, P. S.; Freidinger, R. M. Development of 1,4-Benzodiazepine Cholecystokinin Type B Antagonists. J. Med. Chem. 1993, 36, 4276-4292.
16. Eckhert, H.; Forster, B. Triphosgene, a Crystalline Phosgene Equivalent. Angew. Chem. 1987, 99, 922-933.
17. Jones, R. C. F.; Smallridge, M. J. Annulation of imidazolines. Synthesis of imidazo[1,2-a]pyridones. Tetrahedron Lett. 1988, 29, 5005-5008.
18. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; John Wiley and Sons, Inc.: New York, 1991.
19. Chemistry of the Amino Acids; John Wiley and Sons: New York, 1984; Vol. 2.
20. Evans, B. E.; Bock, M. G.; Rittle, K. E; Dipardo, R. M.; Whitter, W. L; Veber, D. L.; Anderson, P. S.; Freidinger, R. M. Design of Potent, Orally Effective, Nonpeptidyl Antagonists of the Peptide Hormone Cholecystokinin. Proc. Natl. Acad. Sci. U.S A. 1986, 53, 4918-4922.
21. Makovec, F.; Bani, M.; Cereda, R.; Chiste, R.; Pacini, M. A.; Revel, L.; Rovati, L. C. Antispasmodic Activity on the Gallbladder of the Mouse of CR1409 (Lorglumide), a Potent Antagonist of Peripheral Chlolecystokinin. Pharmacol. Res. Commun. 1987, 19, 41-51.
22. Dezube, M.; Sugg, E. E.; Birkemo, L. S.; Croom, D. K.; Dougherty, R. W., Jr.; Ervin, G. N.; Grizzle, M. K.; James, M. K.; Johnson, M. F.; Mosher, J. T.; Queen, K. L.; Rimele, T. J.; Sauls, H. K., Jr.; Triantafillou, J. A. Modification of Receptor Selectivity and Functional Activity in Cholecystokinin Peptoid Ligands J. Med. Chem. 1995, 36, 3384-3390.
23. 2 (A-71623). J. Med. Chem. 1995, 38, 207-211.
24. Bock, M. G.; Dipardo, R. M.; Evans, B. E.; Rittle, K. E; Whitter, W. L.; Veber, D. L.; Anderson, P. S.; Freidinger, R. M. Benzodiazepine Gastrin and Brain CCK Receptor Ligands L365,260 J. Med. Chem. 1989, 32, 13-16.
25. Evans, B. E.; Rittle, K. E.; Bock, M. G.; DiPardo, R. M.; Freidinger, R. M.; Whitter, W. L.; Lundell, G. F.; Veber, D. F.; Anderson, P. S.; Chang, R. S. L.; Lotti, V. J.; Cerino, D. J.; Chen, T. B.; Kling, P. J.; Kunkel, K. A.; Springer, J. P.; Hirshfield, J. Methods for Drug Discovery: Development of Potent, Selective, Orally Effective, Cholecystokinin Antagonists. J. Med. Chem. 1988, 31, 2235-2246.
26. Henke, B. R.; Willson, T. M.; Sugg, E. E.; Croom, D. K.; Dougherty, R. W.; Jr.; Queen, K. L.; Birkemo, L. S.; Ervin, G. N.; Grizzle, M. K.; Johnson, M. F.; James, M. K. 3-(1H-Indazol-3-ylmethyl)-1,5-benzodiazepines: CCK-A Agonists That Demonstrate Oral Activity as Satiety Agents. J. Med. Chem. 1996, 39, 2655-2658.
27. Willson, T. M.; Henke, B. R.; Momtahen, T. M.; Myers, P. L.; Sugg, E. E., Unwalla, R. J.; Croom, D. K.; Grizzle, M. K.; Johnson, M. F.; Queen, K. L.; Rimele, T. R.; Yingling, J. D. and James, M. K. 3-[2-N-Phenylacetamide)]-1,5-benzodiazepines: Orally Active, Binding Selective CCK-A Agonists J. Med. Chem. 1996, 39, 3030-3034.
28. Arunlakshana, O.; Schild, H. O. Some Quantitative Uses of Drug Antagonists Br. J. Pharmacol. 1959, 14, 48-58.