Biarylcarboxylic acids and -amides: Inhibition of phosphodiesterase type IV versus [3H]rolipram binding activity and their relationship to emetic behavior in the ferret

Journal of Medicinal Chemistry

Volumn 39, Issue 1, 1996, Pages 120-125

  Duplantier, Allen J ^a   Biggers, Michael S ^a   Chambers, Robert J ^a   Cheng, John B ^a   Cooper, Kelvin ^a   Damon, David B ^a   Eggler, James F ^a   Kraus, Kenneth G ^a   Marfat, Anthony ^a   Masamune, Hiroko ^a   Pillar, Joann S ^a   Shirley, John T ^a   Umland, John P ^a   Watson, John W ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 [3 (5 PHENYLPENTOXY) 4 METHOXYPHENYL] 2 METHYLBENZOIC ACID; 5 (4 ACETAMIDOPHENYL) 2(1H) PYRAZINONE; AMIDE; BENZOIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CYCLIC GMP; PHOSPHODIESTERASE; PHOSPHODIESTERASE INHIBITOR; PHOSPHODIESTERASE IV; ROLIPRAM; TRITIUM; UNCLASSIFIED DRUG; VINPOCETINE; ZAPRINAST;

AIRWAY OBSTRUCTION; ANAPHYLAXIS; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BINDING SITE; BRAIN; CONTROLLED STUDY; DRUG BINDING; ENZYME INHIBITION; FERRET; GUINEA PIG; MALE; MOUSE; NONHUMAN; ORAL DRUG ADMINISTRATION; VOMITING;

3',5'-CYCLIC-NUCLEOTIDE PHOSPHODIESTERASE; ANIMALS; BENZOATES; BENZOIC ACIDS; BINDING SITES; BRAIN; FERRETS; GUINEA PIGS; HUMANS; MICE; PHOSPHODIESTERASE INHIBITORS; PHOSPHORIC DIESTER HYDROLASES; PYRROLIDINONES; ROLIPRAM; STRUCTURE-ACTIVITY RELATIONSHIP; VOMITING;

EID: 13344295098     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9505066     Document Type: Article

References (22)

1. Schmiechen, R.; Schneider, H. H.; Wachtel, H. Close correlation between behavioural response and binding in vivo for inhibitors of the rolipram-sensitive phosphodiesterase. Psychopharmacology 1990, 102, 17-20.
2. Schneider, H. H.; Schmiechen, R.; Brezinski, M.; Seidler, J. Stereospecific binding of the antidepressant rolipram to brain protein structures. Eur. J. Pharmacol. 1986, 127, 105-115.
3. Torphy, T. J.; Stadel, J. M.; Burman, M.; Cieslinski, L. B.; McLaughlin, M. M.; White, J. R.; Livi, G. P. Coexpression of Human cAMP-specific Phosphodiesterase Activity and High Affinity Rolipram Binding in Yeast. J. Biol. Chem. 1992, 267, 1798-1804.
4. Duplantier, A. J.; Cheng, J. B. Emerging Opportunities in the Treatment of Asthma and Allergy. Annu. Rep. Med. Chem. 1994, 29, 73-81.
5. Nicholson, C. D.; Shahid, M. Inhibitors of Cyclic Nucleotide Phosphodiesterase Isozymes - their Potential Utility in the Therapy of Asthma. Pulmonary Pharmacol. 1994, 7, 1-17.
6. Torphy, T. J.; Livi, G. P.; Christensen, S. B. Novel Phosphodiesterase Inhibitors for the Therapy of Asthma. Drug News Perspect. 1993, 6, 203-214.
7. Lowe, J. A., III; Cheng, J. B. The PDE IV family of calcium-independent phosphodiesterase enzymes. Drugs Future 1992, 17, 799-807.
8. Zeller, E; Stief, H. J.; Pflug, B; Sastre, Y.; Hernandez, M. Results of a phase II study of the antidepressant effect of rolipram. Pharmacopsychiatry 1984, 17, 188-190.
9. Carpenter, D. O ; Briggs, D. B.; Knox, A. P.; Strominger, N. Excitation of Area Postrema Neurons by Transmitters, Peptides, and Cyclic Nucleotides. J. Neurophysiol. 1988, 59, 358-369.
10. Saccomano, N. A.; Vinick, F. J.; Koe, K.; Nielsen, J. A.; Whalen, W. M.; Meltz, M.; Phillips, D.; Thadieo, P. F.; Jung, S.; Chapin, D. S.; Lebel, L. A.; Russo, L. L.; Helweg, D. A.; Johnson, J. L.; Ives, J. L.; Williams, I. H. Calcium-Independent Phosphodiesterase Inhibitors as Putative Antidepressants: [3-(Bicycloalkyloxy)-4-methoxyphenyl]-2-imidazolidinones. J. Med. Chem. 1991, 34, 291-298.
11. Barnette, M. S. Challenges for drug discovery. New Drugs for Asthma-III, Montebello, Quebec, July, 1994.
12. 3H]Rolipram Binding, and Reserpine-Induced Hypothermia in Mice. Drug Dev. Res. 1990, 21, 135-142.
13. Mitsunobu, O. The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products. Synthesis 1981, 1-28.
14. Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. Olefin homologation with titanium methylene compounds. J. Am. Chem. Soc. 1978, 100, 3611-3613.
15. Smith, R. D.; Simmons, H. E. Org. Synth. 1961, 41, 72-75.
16. Erdik, E. Transition metal catalyzed reactions of organozinc reagents. Tetrahedron 1992, 48, 9577-9648.
17. Cavalla, D.; Frith, R. Phosphodiesterase IV Inhibitors: Structural Diversity and Therapeutic Potential in Asthma. Curr. Med. Chem. 1995, 2, 561-572.
18. Engels, P.; Fichtel, K.; Lubbert, H. Expression and regulation of human and rat phosphodiesterase type IV isogenes. FEBS Lett. 1994, 350, 291-295.
19. Reeves, M. L.; Leigh, B. K.; England, P. J. The identification of a new cyclic nueleotide phosphodiesterase activity in human and guinea-pig cardiac ventricle. Biochem. J. 1987, 241, 535-541.
20. 1 receptor. Br. J. Pharmacol. 1995, 115, 84-94.
21. The preparation of 2a has been reported: Meyers, A. I.; Snyder, L. The Synthesis of Aracemic 4-Substituted Pyrrolidinones and 3-Substituted Pyrrolidines. An Asymmetric Synthesis of (-)-Rolipram. J. Org. Chem. 1993, 58, 36-42.
22. The substrate may also be disolved in THF and treated with ammonium hydroxide to give a similar result.