3-Halo-5,7-dimethylpyrazolo[1,5-a]pyrimidines, a Nonbenzodiazepinoid Class of Antianxiety Agents Devoid of Potentiation of Central Nervous System Depressant Effects of Ethanol or Barbiturates

Journal of Medicinal Chemistry

Volumn 20, Issue 3, 1977, Pages 386-393

  Kirkpatrick, William E ^a   Okabe, Takayuki ^a   Hillyard, Ira W ^a   Robins, Roland K ^a   Dren, Anthony T ^a,b   Novinson, Thomas ^a,c  

^a Valeant Pharmaceuticals International   (United States)

^b ABBOTT LABORATORIES   (United States)

^c Pilkington Barnes Hind   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ANALGESIC AGENT; BARBITAL; BARBITURIC ACID DERIVATIVE; CHLORDIAZEPOXIDE; CHLORPROMAZINE; DIAZEPAM; PYRAZOLOPYRIMIDINE; UNCLASSIFIED DRUG;

AGGRESSION; ANXIETY; ARTICLE; BEHAVIOR; CONVULSION; DRUG ANALYSIS; DRUG COMPARISON; DRUG EFFICACY; DRUG INTERACTION; DRUG SCREENING; DRUG SYNTHESIS; DRUG TOXICITY; IN VITRO STUDY; INTRAPERITONEAL DRUG ADMINISTRATION; MONKEY; MOUSE; ORAL DRUG ADMINISTRATION; RAT; STRUCTURE ACTIVITY RELATION; THEORETICAL STUDY;

AGGRESSION; ANALGESICS; ANIMALS; ANTI-ANXIETY AGENTS; ANTICONVULSANTS; AVOIDANCE LEARNING; BARBITAL; BARBITURATES; BEHAVIOR, ANIMAL; CHLORDIAZEPOXIDE; CHLORPROMAZINE; DEPRESSION, CHEMICAL; DIAZEPAM; DRUG SYNERGISM; ETHANOL; FEMALE; HAPLORHINI; HUMANS; LETHAL DOSE 50; MACACA MULATTA; MALE; METHODS; MICE; MOTOR ACTIVITY; MUSCLE RELAXANTS, CENTRAL; PYRIMIDINES; RATS;

EID: 0017615948     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00213a014     Document Type: Article

References (29)

1. T. Novinson, R. Hanson, M. K. Dimmitt, L. N. Simon R. K. Robins, and D. E. O'Brien, J. Med. Chem., 17, 645 (1974).
2. T. Novinson, J. P. Miller, M. Scholten, R. K. Robins, L. N. Simon, D. E. O'Brien, and R. B. Meyer, J. Med. Chem., 18, 460 (1975).
3. B. Beer, M. Chasin, D. E. Clody, J. R. Vogel, and Z. P. Horovitz, Science, 176, 428 (1972).
4. Z. P. Horovitz, B. Beer, D. E. Clody, J. R. Vogel, and M. Chasin, Psychosomatics, 13, 85 (1972).
5. O. S. Ray, in “Methods in Drug Evaluation”, P. Mantegazza and F. Piccinini, Ed., North Holland Press, Amsterdam, Holland, 1966.
6. S. Garattini, E. Mussini, and L. O. Randall, Ed., “The Benzodiazepines”, Raven Press, New York, N.Y., 1973, p 685.
7. N. W. Durham and T. S. Miya, J. Pharm. Soc., 46, 208 (1957).
8. J. von Druey and P. Schmidt, Helv. Chim. Acta, 39, 986 (1956).
9. J. von Druey and P. Schmidt, 41, 306 (1958).
10. B. Lynch, M. A. Khan, S. C. Sharma, and H. C. Leo, Can. J. Chem., 53, 119 (1975).
11. Y. Makisumi, Chem. Pharm. Bull., 10, 612 (1962).
12. Y. Makisumi, Chem. Pharm. Bull., 10, 620 (1962).
13. T. Novinson, R. K. Robins, and T. R. Matthews, J. Med. Chem., 20, 000 (1977).
14. presented at the 168th National Meeting of the American Chemical Society, Atlantic City, N.J., 1974, MEDI 42.
15. W. Ried and E. U. Kocher, Justus Liebigs Ann. Chem., 647, 116 (1961).
16. K. K. Kirk and L. A. Cohen, J. Am. Chem. Soc., 95, 4619 (1973).
17. T. Novinson, R. K. Robins, and D. E. O'Brien, Tetrahedron Lett., 3149 (1973).
18. H. Dorn and H. Dilcher, Justus Liebigs Ann. Chem., 707, 141 (1967).
19. W. Ried and K. P. Peuchert, Justus Liebigs Ann. Chem., 682, 136 (1965).
20. W. Ried and E. U. Kocher, Justus Liebigs Ann. Chem., 647, 116 (1961).
21. J. T. Witkowski, R. K. Robins, G. P. Khare, and R. W. Sidwell, J. Med. Chem., 16, 935 (1973).
22. Kyorin Seiyaku Ltd., Japanese Patent 4876893 (1973).
23. J. R. Vogel, B. Beer, and D. E. Clody, Psychopharmacologia, 21, 1 (1971).
24. C. J. E. Niemegeers, F. J. Verbruggen, and P. A. J. Janssen, Psychopharmacologia, 16, 161 (1969).
25. R. E. Tedeschi, D. H. Tedeschi, A. Mucha, L. Cook, P. A. Mattis, and E. J. Fellows, J. Pharmacol. Exp. Ther., 125, 28 (1959).
26. G. L. Polevoi, in “Transactions of the Science Conference on Analgetics and Antiinflammatory Agents”, Abstracts, Moscow, 1964, pp 159-161.
27. G. L. Polevoi, Ref. Zh., Biol. Khim., 8Ph1773 (1966).
28. A. Takamizawa and Y. Hamashima, Yakugaku Zasshi, 84, 1113 (1964).
29. A. Takamizawa and Y. Hamashima, Chem. Abstr., 62, 5276 (1965).