Synthesis and evaluation of N-(3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-1H- indole-carboxamides as cholecystokinin antagonists

Journal of Pharmacy and Pharmacology

Volumn 58, Issue 3, 2006, Pages 393-401

  Lattmann, Eric ^a   Singh, Harjit ^a   Boonprakob, Yodchai ^b   Lattmann, Pornthip ^a   Sattayasai, Jintana ^b  

^a ASTON UNIVERSITY   (United Kingdom)

^b KHON KAEN UNIVERSITY   (Thailand)

Author keywords

[No Author keywords available]

Indexed keywords

CHOLECYSTOKININ A RECEPTOR; CHOLECYSTOKININ OCTAPEPTIDE; CHOLECYSTOKININ RECEPTOR BLOCKING AGENT; DESIPRAMINE; N (3 OXO 2,3 DIHYDRO 1H PYRAZOL 4 YL) 1H INDOLECARBOXAMIDE DERIVATIVE; N (5 METHYL 3 OXO 1,2 DIPHENYL 2,3 DIHYDRO 1H PYRAZOL 4 YL) 1H INDOLE 2 CARBOXAMIDE; N (5 METHYL 3 OXO 1,2 DIPHENYL 2,3 DIHYDRO 1H PYRAZOL 4 YL) 2 (1H INDOL 3 YL)ACETAMIDE; N (5 METHYL 3 OXO 1,2 DIPHENYL 2,3 DIHYDRO 1H PYRAZOL 4 YL) 3 (1H INDOL 3 YL)PROPANAMIDE; N (5 METHYL 3 OXO 1,2 DIPHENYL 2,3 DIHYDRO 1H PYRAZOL 4 YL) 4 (1H INDOL 3 YL)BUTANAMIDE; N (5 METHYL 3 OXO 1,2 DIPHENYL 2,3 DIHYDRO 1H PYRAZOL 4YL) 1H INDOLE 3 CARBOXAMIDE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SYNTHESIS; IC 50; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION; SWIMMING; TRANQUILIZING ACTIVITY;

AMIDES; ANALGESICS; ANIMALS; ANTIDEPRESSIVE AGENTS; INDOLES; MALE; MAZE LEARNING; MICE; MICE, INBRED ICR; MOTOR ACTIVITY; PAIN MEASUREMENT; PYRAZOLES; RADIOLIGAND ASSAY; RECEPTOR, CHOLECYSTOKININ A; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33644782623     PISSN: 00223573     EISSN: None     Source Type: Journal    
DOI: 10.1211/jpp.58.3.0015     Document Type: Article

References (35)

1. Bock, M. G., DiPardo, R. M., Mellin, E. C., Newton, N. C. (1994) Second-generation benzodiazepine CCK-B antagonists. Development of subnanomolar analogues with selectivity and water solubility. J. Med. Chem. 37: 722-724
2. Bradwejn, J., Koszycki, D., Meterissian, G. (1990) Cholecystokinin tetrapeptide induces panic attacks in patients with panic disorder. Can. J. Psychiatry 35: 83-85
3. Charpentier, B., Pelaprat, D., Durieux, C., Dor, A., Reibaud, M., Blanchard, J. C., Roques, B. P. (1988) Cyclic cholecystokinin analogues with high selectivity for central receptors. Proc. Natl. Acad. Sci. U S A 85: 1968-1972
4. Cowan, A. (1990) Modern methods in pharmacology: recent approaches in the testing of analgesics in animals. Testing and evaluation of drugs of abuse. Wiley-Liss Inc., New York, p 33
5. Dourish, C. T. (1990) Cholecystokinin and anxiety. Trends Pharmacol. Sci. 11: 271-273
6. Dourish, C. T., Rycroft, W., Iversen, S. D. (1989) Postponement of satiety by blockade of brain cholecystokinin-B receptors. Science 245: 1509-1511
7. 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., Cerino, D. J. (1988) Methods for drug discovery: development of potent, selecive, orally effective cholecystokinin-A antagonists. J. Med. Chem. 31: 2235-2246
8. Farghaly, A. M. (1979) Synthesis of some substituted aminophenazones of possible therapeutic interest. Pharmazie 34: 70-73
9. Francesco, M. (1993) CCK-B/gastrin-receptor antagonists. Drugs of the Future 18: 919-928
10. Hirst, G. C., Aquino, C., Birkemo, L., Croom, G. K., Dezube, M. (1996) Discovery of 1,5-benzodiazepines with peripheral cholecystokinin (CCK-A) receptor agonist activity. J. Med. Chem. 39: 5236-5245
11. Hughes, J., Woodruff, G. N. (1992) Neuropeptides function and clinical applications. Arzneimittelforschung 42: 250-255
12. Hughes, J., Boden, P., Costall, B., Domeney, A., Kelly, E. (1990) Development of a class of selective cholecystokinin type B receptor antagonists having potent anxiolytic activity. Proc. Natl. Acad. Sci. U S A 87: 6728-6732
13. Kilfoil, T., Michel, A., Montgomery, D., Whithing, R. L. (1989) Effects of anxiolytic and anxiogenic drugs on exploratory activity in a simple model of anxiety in mice. Neuropharmacology 28: 901-905
14. Kitchen, I., Crowder, I. (1985) Assessment of the hot-plate antinociceptive test in mice: a new method for the statistical treatment of graded data. J. Pharmacol. Meth. 13: 1-7
15. Lattmann, E., Arayarat, P. (2003) From CNS-drugs to anti-neoplastic agents: cholecystokinin (CCK)-antagonists as modern anti-cancer agents. Science 31: 178-193
16. Lattmann, E., Billington, D. C., Poyner, D. R., Howitt, S. B., Offel, M. (2001) Synthesis and evaluation of asperlicin analogues as non-peptidal cholecystokinin-antagonists. Drug Design Discov. 17: 219-230
17. Lattmann, E., Billington, D. C., Poyner, D. R., Arayarat, P., Howitt, S. B., Lawrence, S., Offel, M. (2002a) Combinatorial solid phase synthesis of multiply-substituted 1,4-benzodiazepines and affinity studies on the CCK2 receptor (Part 1). Drug Design Discov. 18: 9-21
18. 2)-receptor ligands. J. Pharm. Pharmacol. 54: 827-834
19. Lattmann, E., Sattayasai, J., Boonprakob, J., Lattmann, P., Singh, H. (2005) Synthesis and evaluation of N-(5-methyl-3-oxo1,2-diphenyl-2,3-dihydro-1H- pyrazol-4yl)-N-phenylureas as cholecystokinin antagonists. Arzneimittelforschung 55: 251-258
20. Martin, I. L., Lattmann, E. (1999) Benzodiazepine recognition site ligands and GABAA receptors. Exp. Opin. Ther. Patents 9: 1347-1358
21. Masato, S., Yutaka, K., Yoshinori, O., Akito, N., Keiji, M. (1995) New 1,4-benzodiazepin-2-one derivatives as gastrin/cholecystokinin-B antagonists. Chem. Pharm. Bull. 43: 2159-2167
22. 2 receptor antagonists. Exp. Opin. Ther. Patents 11: 445-462
23. Porsolt, R. D., Le Pichon, M., Jalfre, M. (1977) Depression: a new animal model sensitive to antidepressant treatments. Nature 266: 730-732
24. Rasmussen, K., Czachura, J. F., Stockton, M. E., Howbert, J. J. (1993) Electrophysiological effects of diphenylpyrazolidinone cholecystokinin-B and cholecystokinin-A antagonists on midbrain dopamine neurons. J. Pharmacol. Exp. Ther. 264: 480-488
25. Rasmussen, K., Stockton, M. E., Czachura, J. F., Howbert, J. J. (1995) Cholecystokinin and schizophrenia: the selective CCK-B antagonists decreases midbrain dopamine unit activity. Exp. Opin. Invest. Drugs 4: 313-322
26. Roth, H. J., Kleemann, A. (1999) Drug synthesis. Pharmaceutical chemistry. Ellis Horwood, Chichester, pp 1, 202-297
27. Ruhkopf, H. (1940) Ueber einige oxy-pyrazolidine. Chem. Ber. 73: 820-822
28. 2+ mobilization. Eur. J. Pharmacol. 269: 249-254
29. Silverman, P. (1978) Approach to conditioned stimulus mazes. Animal behaviour in the laboratory. Chapman and Hall, London, p 110-119
30. Simpson, K., Serpell, M., McCubbins, T. D., Padfield, N. L., Edwards, N., Markam, K., Eastwood, D., Block, R., Rowbotham, D. J. (2001) Management of neuropathic pain in patients using a CCK antagonist Devazepide as an adjunct to srong opioids, 4th International Conference on the Mechanisms and Treatment of Neuropathic Pain, September 2001, San Francisco, USA
31. Stenzl, H., Staub, A., Simon, C. H., Baumann, W. (1950) Zur Kenntnis der 3-Amino-pyrazolone. Helv. Chim. Acta. 33: 1183-1195
32. Trivedi, K., Bharat, J. (1994) Cholecystokinin receptor antagonists: current status. Curr. Med. Chem. 1: 313-327
33. Vogel, H. G., Vogel, W. H. (1997) Pharmacological assays. Drug discovery and evaluation. Springer, Berlin, p 232-276
34. Walker, J. M., Dixon, W. C. (1985) A solid state device for the measuring sensitivity to thermal pain. Physiol. Behav. 30: 481-492
35. Yu, Y., Jawa, A., Pan, W., Kastin, A. J. (2004) Effects of peptides, with emphasis on feeding, pain, and behaviour. Peptides 25: 2257-2289