Discovery of 1,5-benzodiazepines with peripheral cholecystokinin (CCK-A) receptor agonist activity. 1. Optimization of the agonist "trigger"

Journal of Medicinal Chemistry

Volumn 39, Issue 2, 1996, Pages 562-569

  Aquino, Christopher J ^a   Armour, Duncan R ^b   Berman, Judd M ^a   Birkemo, Larry S ^a   Carr, Robin A E ^b   Croom, Dallas K ^a   Dezube, Milana ^a   Dougherty Jr , Robert W ^a   Ervin, Gregory N ^a   Grizzle, Mary K ^a   Head, Julie E ^b   Hirst, Gavin C ^a   James, Michael K ^a   Johnson, Michael F ^a   Miller, Laurence J ^c   Queen, Kennedy L ^a   Rimele, Thomas J ^a   Smith, David N ^b   Sugg, Elizabeth E ^a  

^a GLAXOSMITHKLINE   (United States)

^b GLAXOSMITHKLINE   (United Kingdom)

^c MAYO CLINIC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (2,3 DIHYDRO 1 METHYL 2 OXO 5 PHENYL 1H 1,4 BENZODIAZEPIN 3 YL) 3 (3 METHYLPHENYL)UREA; BENZODIAZEPINE DERIVATIVE; CHOLECYSTOKININ OCTAPEPTIDE; CHOLECYSTOKININ RECEPTOR STIMULATING AGENT; DEVAZEPIDE;

ANIMAL TISSUE; ARTICLE; DRUG EFFECT; DRUG SCREENING; GALLBLADDER CONTRACTION; GUINEA PIG; NONHUMAN; OBESITY; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION;

AMINO ACID SEQUENCE; ANIMALS; APPETITE DEPRESSANTS; BENZODIAZEPINES; CHO CELLS; CRICETINAE; GALLBLADDER; GUINEA PIGS; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR SEQUENCE DATA; MUSCLE CONTRACTION; RATS; RECEPTOR, CHOLECYSTOKININ A; RECEPTORS, CHOLECYSTOKININ; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT;

EID: 0030064088     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm950626d     Document Type: Article

References (27)

1. Crawley, J. N.; Corwin, R. L. Biological Actions of Cholecystokinin. Peptides 1994, 15, 731-755.
2. 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.
3. 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.
4. 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 1990170, 25-31
5. 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.
6. Hermkens, P. H. H.; Ottenheijm, H. C. J.; van der Werf-Pieters, J. M. L.; Broekkamp, C. L. E.; de Boer, T.; van Nispen, J. W. CCK-A Agonists: Endeavours Involving Structure-Activity Relationship Studies. Recl. Trav. Chim. Pays-Bas 1993, 112, 95-106.
7. Shiosaki, K.; Lin, C. W.; Kopecka, H.; Craig, R.; Wagenaar, F. L.; Bianchi, B.; Miller, T.; Witte, D.; Nadzan, A M. Development of CCK-Tetrapeptide Analogues as Potent and Selective CCK-A Receptor Agonists. J. Med. Chem. 1990, 33, 2950-2952.
8. Freidinger, R. M. Toward Peptide Receptor Ligand Drugs: Progress on Nonpeptides. Prog. Drug Res. 1985, 40, 33-98.
9. Giannis, A.; Kolter T. Peptidomimetics for Receptor Ligands Discovery, Development, and Medicinal Perspectives. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244-1267.
10. Rees, D. C. Non-Peptide Ligands for Membrane-Bound Peptide Receptors. Curr. Med. Chem. 1994, 1, 145-158.
11. 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, 83, 4918-4922.
12. Bock, M. G.; Dipardo, R. M.; Evans, B. E.; Rittle, K. E.; Whitter, W. L.; Veber, D. F.; Anderson, P. S.; Freidinger, R. M. Benzodiazepine Gastrin and Brain CCK Receptor Ligands: L365,260. J. Med. Chem. 1989, 32, 13-16.
13. Chang, R. S.; Lotti, V. J.; Monaghan, R. L.; Birnbaum, J.; Stapley, E. O.; Goetz, M. A.; Albers-Schonberg, G.; Patchett, A. A.; Liesch, J. M.; Hensens, O. D. A Potent Nonpeptide Cholycystokinin Antagonist Selective for Peripheral Tissues Isolated from Aspergillus Alliaceus. Science 1985, 230, 177-179.
14. 2 (A-71623). J. Med. Chem. 1995, 38, 207-211.
15. Abdel-Magid, A, P.; Maryanoff, C. A.; Carson, K. G. Reductive Amination of Aldehydes and Ketones by Using Sodium Triacetoxyborohydride. Tetrahedron Lett. 1990, 31, 5595-5598.
16. Koetsch, C. F.; Britain, J. W. Effect of N-Alkyl on Formation of Quinolines from N-Alkylbenzoylacetanilides. J. Org. Chem. 1959, 24, 1551-1553.
17. Marshall, G. R. A Hierarchical Approach to Peptidomimetic Design Tetrahedron 1993, 17, 3547-3558.
18. Strader, C. D.; Fong, T. M.; Tata, M. R.; Underwood, D. Structure and Function of G Protein-Coupled Receptors. Ann. Rev. Biochem. 1994, 63, 101-132.
19. Schwartz, T. W. Locating Ligand-Binding Sites in 7TM Receptors by Protein Engineering. Curr. Opin. Biotech. 1994, 5, 434-444.
20. Heerding, J.; Raynor, K.; Kong, H.; Yu, L.; and Reisine, T. Mutagenesis Reveals that Agonists and Peptide Antagonists Bind in Fundamentally Distinct Manners to the Rat mu Receptor than Do Nonpeptide Antagonists. Regulatory Peptides 1994, 54, 119-120.
21. Wang, J. B.; Imai, Y.; Johnson, P. S.; Walther, D.; Stein, C.; Schaefer, M.; Wu, J. M.; Wang, W. F.; Moriwaki, A.; Uhl, G. R. Human μ Receptor: Gene Structure, Expression, and μ/κ chimeras That Define Nontransmembrane Domains Influencing Peptide Binding Affinities. Ibid. 1994, 54, 317-320.
22. Onogi, T.; Minami, M.; Katao, Y.; Nakagawa, T.; Aoki, Y.; Toya, T.; Katsumata, S.; and Satoh, M. DAMGO, A μ-Opioid Receptor Selective Agonist, Distinguishes Between μ- and δ-opioid receptors Around their First Extracellular Loops. FEBS Lett. 1995, 357, 93-97.
23. Beinborn, M.; Lee, Y. M.; McBride, E. W.; Quinn, S. M.; Kopin, A. S. A Single Amino Acid of the Cholecystokinin-B/Gastrin Receptor Determines Specificity for Non-Peptide Antagonists. Nature 1993, 362, 348-350.
24. Mantamadiotis, T.; Baldwin, G. S. The Seventh Transmembrane Domain of Gastrin/CCK Receptors Contributes to Nonpeptide Antagonist Binding. Biochem. Biophys. Res. Commun. 1994, 201, 1381-1389.
25. Furst, S.; Hosztafi, S; Friedmann, T. Structure Activity Relationships of Synthetic and Semisynthetic Opioid Agonists and Antagonists. Curr. Med. Chem. 1995, 1, 423-440.
26. Perlman, S.; Schambye, J. T.; Rivero, R. A.; Greenlee, W. J.; Hjorth, S. A.; Schwartz, T. W. Nonpeptide Angiotensin Agonist. J. Biol. Chem. 1995, 270, 1493-1496.
27. Kivlign, S. D.; Huckle, W. R.; Zingaro, G. J.; Rivero, R. A.; Lotti, V. J.; Chang, R. S. L.; Schorn, T. W.; Kevin, N.; Johnson, R. G., Jr.; Greenlee, W. J.; Siegl, P. K. S. Discovery of L-162,313: A Nonpeptide That Mimics the Biological Actions of Angiotensin II. Am. J. Physiol., 1995, 268, R820-R823.