Non-peptide cholecystokinin-B/gastrin receptor antagonists based on bicyclic, heteroaromatic skeletons

Journal of Medicinal Chemistry

Volumn 39, Issue 9, 1996, Pages 1806-1815

  Kalindjian, S Barret ^a   Buck, Ildiko M ^a   Davies, Jonathan M R ^a   Dunstone, David J ^a   Hudson, Martin L ^a   Low, Caroline M R ^a   McDonald, Iain M ^a   Pether, Michael J ^a   Steel, Katherine I M ^a   Tozer, Matthew J ^a   Vinter, J G ^a,b  

^a James Black Foundation   (United Kingdom)

^b UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO[2.2.2]OCTANE DERIVATIVE; CHOLECYSTOKININ B RECEPTOR ANTAGONIST; GASTRIN ANTAGONIST;

ANIMAL EXPERIMENT; ARTICLE; DOG; DRUG EFFECT; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; INTRAVENOUS DRUG ADMINISTRATION; NONHUMAN; RAT; STOMACH ACID SECRETION;

ANIMALS; DOGS; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MODELS, MOLECULAR; POLYCYCLIC COMPOUNDS; RATS; RECEPTOR, CHOLECYSTOKININ B; RECEPTORS, CHOLECYSTOKININ; SPECIES SPECIFICITY;

EID: 15844389649     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9508907     Document Type: Article

References (18)

1. Douglas, B. R.; Jebbink, M. C. W.; Tjon a Tham, R. T. O.; Jansen, J. B. M. J.; Lamers, C. B. H. W. The Effect of Loxiglumide (CR-1505) on Basal and Bombesin Stimulated Gallbladder Volume in Man. Eur. J. Pharmacol. 1989, 166, 307-10.
2. Jebbink, M. C W.; Jansen, J. B. M. J.; Mooy, D. M.; Rovati, L. C.; Lamers, C. B. H. W. Effect of the Specific Cholecystokinin-Receptor Antagonist Loxiglumide on Bombesin Stimulated Pancreatic Enzyme Secretion in Man. Regul. Pept. 1991, 32, 361-8.
3. 3H-MK-329. J. Neurosci. 1990, 10.4, 1070-81.
4. Takeuchi, K.; Speir, G. R.: Johnson, L. R. Mucosal Gastrin Receptor. I. Assay Standardisation and Fulfillment of Receptor Criteria. Am. J. Physiol. 1979, 237, E284-94.
5. Moran, T. H.; Robinson, P. H.; Goldrich, M. S.; McHugh, P. R. Two Brain Cholecystokinin Receptors: Implications for Behavioural Actions. Brain Res. 1986, 362, 175-9.
6. Kalindjian, S. B.; Bodkin, M. J.; Buck, I. M.; Dunstone, D. J.; Low, C. M. R ; McDonald, I. M.; Pether, M. J.; Steel, K. I. M. A New Class of Non-Peptide Cholecystokinin-B/Gastrin Receptor Antagonists Based on Dibenzobicyclo[2.2.2]octane. J. Med. Chem. 1994, 37, 3671-3.
7. Kalindjian, S. B.; Buck, I. M.; Cushnir, J. R.; Dunstone, D. J.; Hudson, M. L.; Low, C M. R.; McDonald, I. M.; Pether, M. J.; Steel, K. I. M.; Tozer, M. J. Improving the Affinity and Selectivity of a Nonpeptide Series of Cholecystokinin-B/Gastrin Receptor Antagonists Based on the Dibenzobicyclo[2.2.2]octane Skeleton. J. Med. Chem. 1995, 38, 4294-4302.
8. Culhane, P. J; Woodward, G. E. 3-Nitrophthalic acid. Organic Synthesis; Wiley: New York, 1932; Collect. Vol. I, p 408-10.
9. Leonard, N. J.; Kazmierczak, F.; Rykowski, A. A Convenient Synthesis of lin-Benzopurines through a Common Intermediate. J. Org. Chem 1987, 52, 2933-5.
10. Terpestra, J. W.; van Leusen, A. M. A New Synthesis of Benzo-[b]thiophenes and benzo[c]thiophenes by Annulation of Disbustituted Thiophenes. J. Org. Chem. 1986, 51, 230-8.
11. 3H) via in Situ Generated Superelectrophilic Iodine (1) Trifluoromethanesulfonate. J. Org. Chem. 1993, 58, 3194-5.
12. Vinter, J. G.; Trollope, K. I.; Multi-conformational Composite Molecular Potential Fields in the Analysis of Drug Action. (I) Methodology and First Evaluation using 5-HT and Histamine Action as examples. J. Comput.-Aided Drug Des. 1995, 9, 297-307.
13. Vinter, J. G Extended Electron Distributions Applied to the Molecular Mechanics of Intermolecular Interactions. J. Comput.-Aided Drug Des. 1994, 8, 653-68.
14. (a) Harper, E. A.; Shankley, N. P; Roberts, S. P.; Black, J. W. Analysis of Variation and Complexity in L-365.260 Competition Curves in Radioligand Binding Assays. Br. J. Pharmacol., submitted.
15. (b) James Black Foundation Patent Publication Number WO patent Application 93/16982, 1993.
16. A-Receptor Antagonist. Br. J. Pharmacol. 1993, 108, 734-40.
17. Beinborn, W.; 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, 348-50.
18. Wank, S. A.; Pisegna, J. R.; De Weerth, A. Brain and Gastrointestinal Cholecystokinin Receptor Family: Structure and Functional Expression. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 8691-5.