Identification and structure-activity studies of novel ultrashort-acting benzodiazepine receptor agonists

Bioorganic and Medicinal Chemistry Letters

Volumn 12, Issue 21, 2002, Pages 3215-3218

  Stafford, Jeffrey A ^a,b   Pacofsky, Gregory J ^a,c   Cox, Richard F ^a   Cowan, Jill R ^a   Dorsey, George F ^a   Gonzales, Stephen S ^a   Jung, David K ^a   Koszalka, George W ^a   McIntyre, Maggie S ^a   Tidwell, Jeffrey H ^a   Wiard, Robert P ^a   Feldman, Paul L ^a  

^a GLAXOSMITHKLINE   (United States)

^b Takeda San Diego Inc   (United States)

^c Chrysalon   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BENZODIAZEPINE RECEPTOR STIMULATING AGENT; CARBOXYLIC ACID; GLUTAMIC ACID;

ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG HALF LIFE; DRUG SCREENING; DRUG SOLUBILITY; DRUG SYNTHESIS; NONHUMAN; RAT; RECEPTOR AFFINITY; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ANIMALS; BENZODIAZEPINES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HUMANS; MUSCULOSKELETAL EQUILIBRIUM; RATS; RECEPTORS, GABA-A; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 18644377071     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(02)00512-7     Document Type: Article

References (19)

1. (a) Marshall, B. E.; Longnecker, D. E. General Anesthetics. In The Pharmacological Basis of Therapeutics, 8th ed.; Gilman, A. G., Rall, T. W., Nies, A. S., Taylor, P., Eds.; Pergamon: New York, 1990; p 303.
2. (b) Rall, T. W. Ibid, p 346.
3. Shafer A. Crit. Care Med. 26:1998;947.
4. Kanto J.H. Pharmacotherapy. 5:1985;138.
5. Hudson R.D., Wolpert M.K. Arch Int. Pharmacodyn. Ther. 186:1970;388.
6. Feldman, P. L.; Jung, D. K.; Kaldor, I.; Pacofsky, G. J.; Stafford, J. A.; Tidwell, J. H. WO 0069836, 2000. CAN 134:4954.
7. (a) Remifentanil is marketed under the tradename Ultiva®.
8. (b) James, M. K.; Feldman, P. L.; Schuster, S. V.; Bilotta, J. M.; Brackeen, M. F.; Leighton, H. J. J. Pharmacol. Exp. Ther. 1991, 259, 712.
9. © Feldman, P. L.; James, M. K.; Brackeen, M. F.; Bilotta, J. M.; Schuster, S. V.; Lahey, A. P.; Lutz, M. W.; Johnson, M. R.; Leighton, H. J. J. Med. Chem. 1991 34, 2202.
10. Lutz M.W., Morgan P.H., James M.K., Feldman P.L., Brackeen M.F., Lahey A.P., James S.V., Bilotta J.M., Pressley J.C. J. Pharmacol. Exp. Ther. 271:1994;795.
11. Bolin D.R., Sytwu I.I., Humiec F., Meienhofer J. Int. J. Peptide Protein Res. 33:1989;353.
12. Carpino L.A., Cohen B.J., Stephens K.J. Jr., Sadat-Alaee S.Y., Tien J.-H., Langridge D.C. J. Org. Chem. 51:1986;3732.
13. For a synthesis of similar ester-containing BZDS from diethyl aspartate, see: Manghisi, E.; Salimbeni, A. Boll. Chim. Farm. 1974, 113, 642. These analogues were reported to be inactive.
14. Otera J., Ioka S., Nozaki H. J. Org. Chem. 54:1989;4013.
15. Bell S.C., McCaully R.J., Gochman C., Childress S.J., Gluckman M.I. J. Med. Chem. 11:1968;457.
16. Sherrill R.G., Sugg E.E. J. Org. Chem. 60:1995;730.
17. i values were calculated, see: Cheng, Y.-C.; Prusoff, W. H. Biochem. Pharmacol. 1973, 22, 3099.
18. Ananthan S., Clayton S.D., Ealick S.E., Wong G., Evoniuk G.E., Skolnick P. J. Med. Chem. 36:1993;479.
19. Hester J.B. Jr., Rudzik A.D., Kamdar B.V. J. Med. Chem. 14:1971;1078.