Structure-activity relationship investigations of a potent and selective benzodiazepine oxytocin antagonist

Bioorganic and Medicinal Chemistry Letters

Volumn 11, Issue 10, 2001, Pages 1301-1305

  Wyatt, Paul G ^a   Allen, Michael J ^a   Chilcott, Josie ^a   Hickin, Gwen ^a   Miller, Neil D ^a   Woollard, Patrick M ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BENZODIAZEPINE DERIVATIVE; GW 405212X; OXYTOCIN ANTAGONIST; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG CLEARANCE; DRUG POTENCY; DRUG STRUCTURE; HUMAN; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ADMINISTRATION, ORAL; ANIMALS; BENZODIAZEPINES; BIOLOGICAL AVAILABILITY; DOGS; HUMANS; INHIBITORY CONCENTRATION 50; INJECTIONS, INTRAVENOUS; OXYTOCIN; PEPTIDE LIBRARY; PROTEIN BINDING; RECEPTORS, OXYTOCIN; STRUCTURE-ACTIVITY RELATIONSHIP; TOCOLYTIC AGENTS;

EID: 0035927248     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(01)00202-5     Document Type: Article

References (16)

1. Goldenberg R.L., Rouse D.J. N. Engl. J. Med. 339:1998;313.
2. Higby K., Suiter C.R. Drugs Safety. 21:1999;35.
3. Kimura T., Takemura M., Nomura S., Nobunaga T., Kubota Y., Inoue T., Hashimoto K., Kumazawa I., Ito Y., Ohashi K., Koyama M., Azuma C., Kitamura Y., Saji F. Endocrinology. 137:1996;780.
4. Keelan J.A., Coleman M., Mitchell M.D. Clin. Obstet. Gynecol. 40:1997;460.
5. Goodwin T.M., Zograbyan A. Clin Perinatol. 25:1998;859.
6. Bossmar T. J. Perinat. Med. 26:1998;458.
7. Pettibone D.J., Clineschmidt B.V., Guidotti M.T., Lis M.T., Reiss D.R., Woyden C.J., Bock M.G., Evans B.E., Freidinger R.M., Hobbs D.W., Veber D.F., Williams P.D., Chiu S.-H.L., Thompson K.L., Schorn T.W., Siegel P.K.S., Kaufman M.J., Cukierski M.A., Haluska G.J., Cook M.J., Novy M.J. Drug Devel. Res. 30:1993;129.
8. Bell I.M., Erb J.M., Freidinger R.M., Gallicchio S.N., Guare J.P., Guidotti M.T., Halpin R.A., Hobbs D.W., Homnick C.F., Kuo M.S., Lis M.T., Mathre D.J., Michelson S.R., Pawluczyk J.M., Pettibone D.J., Reiss D.R., Vickers S., Williams P.D., Woyden C.J. J. Med. Chem. 41:1998;2146.
9. Evans B., Pipe A.J., Clark E.A., Banks M. Bioorg. Med. Chem. Lett. 11:2001;1297.
10. 12 Oxytocin was obtained as the acetate salt (Sigma, UK).
11. Kimura T., Tanizawa O., Mori K., Brownstein M.J., Okayama H. Nature. 356:1992;526. [published erratum appears in Nature 1992, 357, 176].
12. Rees S., Coote J., Stables J., Goodson S., Harris S., Lee M.G. Biotechniques. 20:1996;102.
13. Cheng Y., Prusoff W.H. Biochem. Pharmacol. 22:1973;3099.
14. Solid-phase chemistry was carried out on Tentagel amino High Load 160 micron beads supplied by Rapp Polymere, Rapp Polymere GmbH, Ernst-Simon-Str. 9, D 72072 Tübingen, Germany. (R,S)-FMOC-3-amino-N-1-carboxymethyl-2-oxo-5-phenyl-1,4-benzodiazepine was purchased from Neosystem Laboratoire, 7 Rue de Boulogne, 67100 Strasbourg, France.
15. Compound 6 (R,S)-2-oxo-5-phenyl-3-(phenylmethoxycarbonylamino)-1,4-benzodiazepine was purchased from Neosystem Laboratoire, 7 Rue de Boulogne, 67100 Strasbourg, France.
16. Bock M.G., DiPardo R.M., Evans B.E., Rittle K.E., Whitter W.L. J. Med. Chem. 36:1993;4276.