Progress in the development of oxytocin antagonists for use in preterm labor

Advances in Experimental Medicine and Biology

Volumn 449, Issue , 1998, Pages 473-479

  Williams, Peter D ^a   Bock, Mark G ^a   Evans, Ben E ^a   Freidinger, Roger M ^a   Pettibone, Douglas J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 [1 [4 (3 ACETAMIDOPROPOXY)BENZOYL] 4 PIPERIDYL] 1,2,3,4 TETRAHYDRO 2 QUINOLINONE; 1 [[[2 [2 AMINO 4 (METHYLSULFONYL)BUTYRAMIDO] 7,7 DIMETHYLBICYCLO[2.2.1]HEPTAN 1 YL]METHYL]SULFONYL] 4 (2 METHYLPHENYL)PIPERAZINE; 1,4 DIHYDRO 1 [1 [2 METHOXY 4 [1 (2 METHYL 1 OXIDO 3 PYRIDINYLMETHYL) 4 PIPERIDINYLOXY]BENZOYL] 4 PIPERIDINYL]BENZ[D][1,3]OXAZIN 2 ONE; ATOSIBAN; OXYTOCIN ANTAGONIST; OXYTOCIN RECEPTOR; UNCLASSIFIED DRUG; VASOPRESSIN RECEPTOR;

CLINICAL TRIAL; DRUG BIOAVAILABILITY; DRUG EFFICACY; DRUG IDENTIFICATION; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SAFETY; DRUG SELECTIVITY; DRUG SOLUBILITY; HUMAN; INTRAVENOUS DRUG ADMINISTRATION; NONHUMAN; ORAL DRUG ADMINISTRATION; PREMATURE LABOR; PRIORITY JOURNAL; RECEPTOR AFFINITY; REVIEW; TOCOLYSIS; UTERUS CONTRACTION;

CANIS FAMILIARIS; DRYOBALANOPS; MACACA MULATTA;

EID: 0031704132     PISSN: 00652598     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-1-4615-4871-3_61     Document Type: Review

References (18)

1. Fuchs AR, Fuchs F, Stubblefield PG (editors) Preterm Birth. Causes, Prevention, and Management, second edition. 1993, McGraw-Hill, New York.
2. Canadian Preterm Labor Investigators Group (1992) Treatment of preterm labor with the beta-adrenergic agonist ritodrine. N Engl J Med 327:308-12.
3. Goodwin TM, Valenzuela GJ, Silver H, Creasy G (1996) Dose ranging study of the oxytocin antagonist atosiban in the treatment of preterm labor. Obstet Gynecol 88: 331-6.
4. Pettibone DJ, Clineschmidt BV, Anderson PS, Freidinger RM, Lundell GF, Koupal LR, Schwartz CD, Williamson JM, Goetz MA, Hensens OD, Liesch JM, Springer JP (1989) A unique, potent, and selective oxytocin antagonist derived from Streptomyces silvensis. Endocrinol 125:217-22.
5. Bock MG, DiPardo RM, Williams PD, Pettibone DJ, Clineschmidt BV, Ball RG, Veber DF, Freidinger RM (1990) Receptor ligands which bind the oxytocin receptor with selectivity and high affinity. Chemical modification of a Streptomyces silvensis derived cyclic hexapeptide. J Med Chem 33:2321-3.
6. Williams PD, Bock MG, Tung RD, Garsky VM, Perlow DS, Erb JM, Lundell GF, Gould NP, Whitter WL, Hoffman JB, Kaufman MJ, Clineschmidt BV, Pettibone DJ, Freidinger RM, Veber DF (1992) Development of a novel class of cyclic hexapeptide oxytocin antagonists based on a natural product. J Med Chem 35:3905-18.
7. Pettibone DJ, Clineschmidt BV, Lis EV, Reiss DR, Totaro JA, Woyden CJ, Bock MG, Freidinger RM, Tung RD, Veber DF, Williams PD, Lowensohn RI (1991) In vitro pharmacological profile of anovel structural class of oxytocin antagonists. J Pharmacol Exp Ther 256:304-8.
8. Evans BE, Leighton JL, Rittle KE, Gilbert KF, Lundell GF, Gould NP, Hobbs DW, DiPardo RM, Veber DF, Pettibone DJ, Clineschmidt BV, Anderson PS, Freidinger RM (1992) Orally active, nonpeptide oxytocin antagonists. J Med Chem 35:3919-27.
9. Pettibone DJ, Clineschmidt BV, Kishel MT, Lis EV, Reiss DR, Woyden CJ, Evans BE, Freidinger RM, Veber DF, Cook MJ, Haluska GJ, Novy MJ, Lowensohn RI (1993) Identification of an orally active, nonpeptidyl oxytocin antagonist. J Pharmacol Exp Ther 264:308-14.
10. Evans BE, Lundell GF, Gilbert KF, Bock MG, Rittle KE, Carroll LA, Williams PD, Pawluczyk JM, Leighton JL, Young MB, Erb JM, Hobbs DW, Gould NP, DiPardo RM, Hoffman JB, Perlow DS, Whitter WL, Veber DF, Pettibone DJ, Clineschmidt BV, Anderson PS, Freidinger RM (1993) Nanomolar-affinity, non-peptide oxytocin receptor antagonists. J Med Chem 36:3993-4005.
11. Williams PD, Anderson PS, Ball RG, Bock MG, Carroll LA, Chiu SL, Clineschmidt BV, Culberson JC, Erb JM, Evans BE, Fitzpatrick SL, Freidinger RM, Kaufman MJ, Lundell GF, Murphy JS, Pawluczyk JM, Perlow DS, Pettibone DJ, Pitzenberger SM, Thompson KL, Veber DF (1994) 1-(((7,7-Dimethyl-2(S)-(2(S)-amino-4-(methylsulfonyl)butyramido)bicyclo[2.2.1 ]heptan-1 (S)-yl)methyl)sulfonyl)-4-(2-methylph enyl)piperazine (L-368,899): An orally bioavailable, non-peptide oxytocin antagonist with potential utility for managing preterm labor. J Med Chem 37:565-71.
12. Pettibone DJ, Clineschmidt BV, Guidotti MT, Lis EV, Reiss DR, Woyden CJ, Bock MG, Evans BE, Freidinger RM, Hobbs DW, Veber DF, Williams PD, Chiu SL, Thompson KL, Schorn TW, Siegl PKS, Kaufman MJ, Cukierski MA, Haluska GJ, Cook MJ, Novy MJ (1993) L-368,899, a potent orally active oxytocin antagonist for potential use in preterm labor. Drug Devel Res 30:129-42.
13. Hatangandi S, Grasing K, Murphy MG, Siebold JR, Barren JS, Chavez C, Constanzer M, Vigna T, Baglivo P, Capra N, Gonyo G, Knuppel RA (1994) Human tolerability and pharmacokinetics of L-368,899: a novel oxytocin receptor antagonist. Society for Gynecologic Investigation Annual Meeting P271.
14. Egerman R, Murphy MG, Dougherty E, Capra N, Staub T, Winchell G, Constanzer ML, Chavez C, Meyer N, Cotroneo M, Caritis S, Sibai B (1995) The oxytocin antagonist, L-368,899, inhibits oxytocin-stimulated uterine contractions in the immediate postpartum period. Am J Obstet Gynecol 172:414.
15. Chiu SHL, Thompson KA, Vincent SH, Alvaro RF, Huskey SEW, Stearns RA, Pettibone DJ (1995) The role of drug metabolism in drug discovery: a case study in the selection of an oxytocin receptor antagonist for development. Toxicol Pathol 23:124-130.
16. Williams PD, Ball RG, Clineschmidt BV, Culberson JC, Erb JM, Freidinger RM, Pawluczyk JM, Perlow DS, Pettibone DJ, Veber DF (1994) Conformationally constrained o-tolylpiperazine camphorsulfonamide oxytocin antagonists. Structural modifications that provide high receptor affinity and suggest a bioactive conformation. Bioorg Med Chem 2:971-85.
17. Ohnishi A, Ko Y, Fujihara H, Miyamoto G, Okada K, Odomi M (1993) Pharmacokinetics, safety, and pharmacologie effects of OPC21268, a nonpeptide orally active vasopressin VI receptor antagonist, in humans. J Clin Pharm 33:230-8.
18. Williams PD, Clineschmidt BV, Erb JM, Freidinger RM, Guidotti MT, Lis EV, Pawluczyk JM, Pettibone DJ, Reiss DR, Veber DF, Woyden CJ (1995) 1-{1-[4-[(N-Acetyl-4-piperidiny])oxy]-2-methoxybenzoyl]piperidin-4-yl}-4H-3,1- benzoxazin-2(1H)-one (L-371,257): a new, orally bioavailable, non-peptide oxytocin antagonist. J Med Chem 38:4634-6.