Synthesis and SAR of new 5-phenyl-3-ureido-1,5-benzodiazephines as cholecystokinin-B receptor antagonists

Journal of Medicinal Chemistry

Volumn 43, Issue 20, 2000, Pages 3596-3613

  Ursini, A ^a   Capelli, A M ^a   Carr, R A E ^a,b   Cassara P ^a,c   Corsi, M ^a   Curcuruto, O ^a   Curotto, G ^a   Dal Cin, M ^a   Davalli, S ^a   Donati, D ^a   Feriani, A ^a   Finch, H ^a,b   Finizia, G ^a   Gaviraghi, G ^a   Marien, M ^a,d   Pentassuglia, G ^a   Polinelli, S ^a   Ratti, E ^a   Reggiani, A ^a   Tarzia, G ^a,e   Tedesco, G ^a   Tranquillini, M E ^a   Trist, D G ^a   Van Amsterdam, F T M ^a   more..

^a GSK   (Italy)

^b GLAXOSMITHKLINE   (United Kingdom)

^c Pro Bio Sint Srl gruppo Archimica   (Italy)

^d INSTITUT DE RECHERCHE PIERRE FABRE   (France)

^e UNIVERSITY OF URBINO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

4 [[2 [2 [[(2 ADAMANTYLOXY)CARBONYL]AMINO] 3 (1H INDOL 3 YL) 2 METHYLPROPIONAMIDO] 1 PHENYLETHYL]AMINO] 4 OXOBUTYRIC ACID MEGLUMINE; 5 PHENYL 3 UREIDO 1,5 BENZODIAZEPINE; CHOLECYSTOKININ B RECEPTOR ANTAGONIST; DEVAZEPIDE; GV 150013; UNCLASSIFIED DRUG; UREA;

ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG ACTIVITY; DRUG CONFORMATION; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTI-ANXIETY AGENTS; BENZODIAZEPINES; CALLITHRIX; CEREBRAL CORTEX; CRYSTALLOGRAPHY, X-RAY; GUINEA PIGS; HELA CELLS; HUMANS; MEMBRANES; MICE; MODELS, MOLECULAR; PANCREAS; RADIOLIGAND ASSAY; RATS; RECEPTOR, CHOLECYSTOKININ A; RECEPTOR, CHOLECYSTOKININ B; RECEPTORS, CHOLECYSTOKININ; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0034609855     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm990967h     Document Type: Article

References (45)

1. Structure of porcine secretin. Amino acid sequence
2. New peptide in the vertebrate CNS [central nervous system] reacting with antigastrin antibodies
3. Immunochemical evidence of cholecystokinin-like peptides in brain
4. The physiology of cholecystokinin in brain and gut
5. Central cholecystokinin 5receptors: Opportunity for drug discovery
6. Evidence for two cholecystokinin receptors mediating the contraction of the guinea pig isolated ileum longitudinal muscle myenteric plexus
7. Analysis of the effect of CCK-8S, pentagastrin and CCK-4 on gastric acid secretion in the isolated rat gastric mucosa
8. Design of potent, orally effective non peptidal antagonists of the peptide hormone cholecystokinin
9. Design of nonpeptidal ligands for a peptide receptor: Cholecystokinin antagonists
10. Rationally designed 'dipeptoid' analogues of CCK. α-methyltryptophan derivatives as highly selective and orally active gastrin and CCK-B antagonists with potent anxiolytic properties
11. Evidence for the neuropeptide cholecystokinin as an antagonist of opiate analgesia
12. Cholecystokinin receptor antagonists: Current status
13. 1,5-benzodiazepines as CCK-B antagonists. Effect of halogen substitution at the benzo-fused ring on potency and selectivity
14. 1,2,4,5-tetrahydro-2,4-dioxo-3H-1,5-benzodiazepins
15. Discovery of 1,5-benzodiazepines with peripheral cholecystokinin (CCK-A) receptor agonist activity. 1. Optimization of the agonist 'trigger'
16. Reaction between 2',3',5'-tri-O-acetyladenosine and aryl chloroformates. 2',3',5'-tri-O-acetyl-N(6)-phenoxycarbonyladenosine as an intermediate in the synthesis of 6-ureidopurine ribosides
17. Crystallization-induced asymmetric transformation; stereospecific synthesis of a potent peripheral CCK antagonists
18. Synthesis and resolution of 3-amino-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-ones
19. Benzodiazepine gastrin and brain cholecystokinin receptor ligands: L-365,260
20. A new amine resolution method and its application to 3-Aminobenzodiazepines
21. Development of 1,4-benzodiazepine cholecystokinin type B antagonists
22. A new method for the resolution of amines and its application to 3-amino-1,5-Benzodiazepines
23. A chemical method for the preparation of novel 1,5-benzodiazepines acting as CCK-B antagonists in high enantiomeric purity
24. Distinct in brain and pancreas. Cholecystokinin receptor
25. Cholecystokinin receptors: Biochemical demonstration and autoradiographical localization in rat brain and pancreas using [3H]cholecystokinin8 as radioligand
26. Anxiolytic activity of GV150013, a new potent and selective cholecystokinin-B (CCK-B) antagonist
27. Novel 1,5-Benzodiazepines as CCK-B ligands. Effect of aryl-carbamic substituents at the C-3 position together with halogen substitution on the benzo-fused ring
28. Synthesis and evaluation of 1,5-Benzodiazepines with bridged cycloalkyl substituents at the N-1-position as potent and selective CCK-B ligands
29. Generating optimal linear PLS estimations (GOLPE): An advanced chemometric tool for handling 3D-QSAR problems
30. A new easily accessible steric parameter for structure-activity relationships
31. A unique geometry of the active site of angiotensin-converting enzyme consistent with structure-activity studies
32. Computer simulation of the conformational properties of oligopeptides. Comparison of theoretical methods and analysis of experimental results
33. The characterization in functional assays of GV150013: A novel CCK-B receptor antagonist
34. Electrochemical oxidation of polyfluoroaromatic amines. I. Synthesis of fluorophenazines
35. Synthesis of aldehydes by a one carbon homologation of ketones and aldehydes via α,β-unsaturated isocyanades
36. Synthesis and polymerization of dimethylaminophenyl isocyanates