메뉴 건너뛰기




Volumn 48, Issue 15, 2005, Pages 4851-4860

Iterative approach to the discovery of novel degarelix analogues: Substitutions at positions 3, 7, and 8. Part II

Author keywords

[No Author keywords available]

Indexed keywords

AZALINE B; CARRIER PROTEIN; DEGARELIX; DEGARELIX 3 [BETA N (2 PYRIDYLMETHYL) 3 DEXTRO ALPHA,BETA DIAMINOPROPIONIC ACID]; DEGARELIX 7 [7 PROPARGYLGLYCINE]; DEGARELIX 8 [SIGMA N (ISOPROPYLGLYCINE) 8 ORNITHINE]; DEGARELIX[BETA N (ISOPROPYL BETA ALANINE) 8 DEXTRO ALPHA,BETA DIAMINOPROPIONIC ACID]; DEGARELIX[GAMMA N (ISOPROPYLGLYCINE) 8 ALPHA,GAMMA DIAMINOBUTYRIC ACID]; DEGARELIX[NALPHA METHYL 7 LEUCINE]; DEGARELIX[NEPSILON CYCLOHEXYL 8 LYSINE]; DEGARELIX[SIGMA N ISOPROPYL 8 ORNITHINE]; FE 200486; GONADORELIN ANTAGONIST; GONADORELIN RECEPTOR; HORMONE ANTAGONIST; LUTEINIZING HORMONE; UNCLASSIFIED DRUG;

EID: 22744439296     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm050134t     Document Type: Article
Times cited : (14)

References (56)
  • 3
    • 0031437969 scopus 로고    scopus 로고
    • Future trends in infertility treatment: Challenges ahead
    • Lunenfeld, B.; Insler, V. Future trends in infertility treatment: challenges ahead. Fertil. Steril. 1997, 68, 977-980.
    • (1997) Fertil. Steril. , vol.68 , pp. 977-980
    • Lunenfeld, B.1    Insler, V.2
  • 6
    • 0022665939 scopus 로고
    • GnRH analogue design structure-function studies toward the development of agonists and antagonists: Rationale and perspective
    • Karten, M. J.; Rivier, J. E. GnRH analogue design structure-function studies toward the development of agonists and antagonists: Rationale and perspective. Endocr. Rev. 1986, 7, 44-66.
    • (1986) Endocr. Rev. , vol.7 , pp. 44-66
    • Karten, M.J.1    Rivier, J.E.2
  • 11
    • 0002995352 scopus 로고
    • Novel antagonists of GnRH: A compendium of their physicochemical properties, activities, relative potencies and efficacy in humans
    • Lunenfeld, B., Insler, V., Eds.; Geneva, Switzerland, February 25-28, 1993; The Parthenon Publishing Group: Carnforth, Lancaster, U.K.
    • Rivier, J. Novel antagonists of GnRH: a compendium of their physicochemical properties, activities, relative potencies and efficacy in humans. GnRH Analogues. The State of the Art 1993; Lunenfeld, B., Insler, V., Eds.; Geneva, Switzerland, February 25-28, 1993; The Parthenon Publishing Group: Carnforth, Lancaster, U.K., 1993; pp 13-26.
    • (1993) GnRH Analogues. The State of the Art 1993 , pp. 13-26
    • Rivier, J.1
  • 15
    • 0023202874 scopus 로고
    • Effect of reductive alkylation of D-lysine in position 6 on the histamine-releasing activity of luteinizing hormone-releasing hormone antagonists
    • Hocart, S. J.; Nekola, M. V.; Coy, D. H. Effect of reductive alkylation of D-lysine in position 6 on the histamine-releasing activity of luteinizing hormone-releasing hormone antagonists. J. Med. Chem. 1987, 30, 739-743.
    • (1987) J. Med. Chem. , vol.30 , pp. 739-743
    • Hocart, S.J.1    Nekola, M.V.2    Coy, D.H.3
  • 16
    • 0010548878 scopus 로고
    • Effect of reductive alkylation of lysine in positions 6 and/or 8 on the histamine-releasing activity of luteinizing hormone-releasing hormone antagonists
    • Hocart, S. J.; Nekola, M. V.; Coy, D. H. Effect of reductive alkylation of lysine in positions 6 and/or 8 on the histamine-releasing activity of luteinizing hormone-releasing hormone antagonists. J. Med. Chem. 1987, 30, 1910-1914.
    • (1987) J. Med. Chem. , vol.30 , pp. 1910-1914
    • Hocart, S.J.1    Nekola, M.V.2    Coy, D.H.3
  • 18
    • 0342993927 scopus 로고    scopus 로고
    • A reductive alkylation procedure applicable to both solution- and solid-phase syntheses of secondary amines
    • Szardenings, A. K.; Burkoth, T. S.; Look, G. C.; Campbell, D. A. A reductive alkylation procedure applicable to both solution- and solid-phase syntheses of secondary amines. J. Org. Chem. 1996, 61, 6720-6722.
    • (1996) J. Org. Chem. , vol.61 , pp. 6720-6722
    • Szardenings, A.K.1    Burkoth, T.S.2    Look, G.C.3    Campbell, D.A.4
  • 19
    • 0000844109 scopus 로고    scopus 로고
    • Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures
    • Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures. J. Org. Chem. 1996, 61, 3849-3862.
    • (1996) J. Org. Chem. , vol.61 , pp. 3849-3862
    • Abdel-Magid, A.F.1    Carson, K.G.2    Harris, B.D.3    Maryanoff, C.A.4    Shah, R.D.5
  • 20
    • 0029330768 scopus 로고
    • Detection of secondary amines on solid phase
    • Vojkovsky, T. Detection of secondary amines on solid phase. Pept. Res. 1995, 8, 236-237.
    • (1995) Pept. Res. , vol.8 , pp. 236-237
    • Vojkovsky, T.1
  • 21
    • 0027261275 scopus 로고
    • New method for the synthesis of N-methyl amino acids containing peptides by reductive methylation of amino groups on the solid phase
    • Kaljuste, K.; Undén, A. New method for the synthesis of N-methyl amino acids containing peptides by reductive methylation of amino groups on the solid phase. Int. J. Pept. Protein Res. 1993, 42, 118-124.
    • (1993) Int. J. Pept. Protein Res. , vol.42 , pp. 118-124
    • Kaljuste, K.1    Undén, A.2
  • 22
    • 20344408524 scopus 로고    scopus 로고
    • Novel gonadotropin-releasing hormone antagonists with substitutions at position 5
    • Samant, M. P.; Hong, D. J.; Croston, G.; Rivier, C.; Rivier, J. Novel gonadotropin-releasing hormone antagonists with substitutions at position 5. Biopolymers 2005, 80, 386-391.
    • (2005) Biopolymers , vol.80 , pp. 386-391
    • Samant, M.P.1    Hong, D.J.2    Croston, G.3    Rivier, C.4    Rivier, J.5
  • 24
    • 0022472366 scopus 로고
    • New effective gonadotropin releasing hormone antagonists with minimal potency for histamine release in vitro
    • Rivier, J.; Porter, J.; Rivier, C.; Perrin, M.; Corrigan, A. Z.; Hook, W. A.; Siraganian, R. P.; Vale, W. W. New effective gonadotropin releasing hormone antagonists with minimal potency for histamine release in vitro. J. Med. Chem. 1986, 29, 1846-1851.
    • (1986) J. Med. Chem. , vol.29 , pp. 1846-1851
    • Rivier, J.1    Porter, J.2    Rivier, C.3    Perrin, M.4    Corrigan, A.Z.5    Hook, W.A.6    Siraganian, R.P.7    Vale, W.W.8
  • 32
    • 0027465167 scopus 로고
    • Primary structure and biological activity of a third gonadotropin- releasing hormone from lamprey brain
    • Sower, S. A.; Chiang, Y. C.; Lovas, S.; Conlon, J. M. Primary structure and biological activity of a third gonadotropin-releasing hormone from lamprey brain. Endocrinology 1993, 132, 1125-1131.
    • (1993) Endocrinology , vol.132 , pp. 1125-1131
    • Sower, S.A.1    Chiang, Y.C.2    Lovas, S.3    Conlon, J.M.4
  • 35
    • 33044497807 scopus 로고
    • Structure/activity relations of LH-RH in vertebrates requirements for amino acid residues in positions seven and eight
    • Quebec, Canada
    • Millar, R.; King, J.; Roeske, R.; Day, W.; Rivier, J.; Licht, P. Structure/activity relations of LH-RH in vertebrates requirements for amino acid residues in positions seven and eight. 7th International Congress of Endocrinology: Quebec, Canada, 1984; p 985.
    • (1984) 7th International Congress of Endocrinology , pp. 985
    • Millar, R.1    King, J.2    Roeske, R.3    Day, W.4    Rivier, J.5    Licht, P.6
  • 36
    • 0021846048 scopus 로고
    • Improved antagonists of luteinizing hormone-releasing hormone modified in position 7
    • Hocart, S. J.; Nekola, M. V.; Coy, D. H. Improved antagonists of luteinizing hormone-releasing hormone modified in position 7. J. Med. Chem. 1985, 28, 967.
    • (1985) J. Med. Chem. , vol.28 , pp. 967
    • Hocart, S.J.1    Nekola, M.V.2    Coy, D.H.3
  • 37
    • 0036129344 scopus 로고    scopus 로고
    • Pharmacological profile of a new, potent and long-acting gonadotropin-releasing hormone antagonist: Degarelix
    • Broqua, P.; Riviere, P.; Conn, P. M.; Rivier, J. E.; Aubert, M. K.; Junien, J.-L. Pharmacological profile of a new, potent and long-acting gonadotropin-releasing hormone antagonist: Degarelix. J. Pharmacol. Exp. Ther. 2002, 301, 95-102.
    • (2002) J. Pharmacol. Exp. Ther. , vol.301 , pp. 95-102
    • Broqua, P.1    Riviere, P.2    Conn, P.M.3    Rivier, J.E.4    Aubert, M.K.5    Junien, J.-L.6
  • 40
    • 14744267587 scopus 로고    scopus 로고
    • Degarelix; A novel GnRH antagonist tested in a multicenter, randomised dose-finding study in prostate cancer patients
    • Hawaii
    • Weston, P. M. T.; Hammonds, J.; Vaughton; et al. Degarelix; a novel GnRH antagonist tested in a multicenter, randomised dose-finding study in prostate cancer patients. 27th Congress of the Société Internationale d'Urologie: Hawaii, 2004.
    • (2004) 27th Congress of the Société Internationale D'Urologie
    • Weston, P.M.T.1    Hammonds, J.2    Vaughton3
  • 41
    • 14744273418 scopus 로고    scopus 로고
    • Synthesis and biological activity of GnRH antagonists modified at position 3 with 3-(2-methoxy-5-pyridyl)alanine
    • Samant, M. P.; Hong, D. J.; Croston, G.; Rivier, C. L.; Rivier, J. E. Synthesis and biological activity of GnRH antagonists modified at position 3 with 3-(2-methoxy-5-pyridyl)alanine. J. Pept. Res. 2005, 65, 284-291.
    • (2005) J. Pept. Res. , vol.65 , pp. 284-291
    • Samant, M.P.1    Hong, D.J.2    Croston, G.3    Rivier, C.L.4    Rivier, J.E.5
  • 42
    • 0006283238 scopus 로고
    • α-t-BOC-2,4-diaminobutyric acid (DBR) derivatives suitable for solid-phase peptide synthesis
    • α-t-BOC-2,4-diaminobutyric acid (DBR) derivatives suitable for solid-phase peptide synthesis. Org. Prep. Procedures Int. 1990, 22, 597-603.
    • (1990) Org. Prep. Procedures Int. , vol.22 , pp. 597-603
    • Stanfield, C.F.1    Felix, A.M.2    Danho, W.3
  • 44
    • 0021100147 scopus 로고
    • Substrate recognition by oligosaccharyltransferase. Studies on glycosylation of modifiedASN-X-THR/SER tripeptides
    • Welply, J. K.; Shenbagamurthi, P.; Lennarz, W. J.; Naider, F. Substrate recognition by oligosaccharyltransferase. Studies on glycosylation of modifiedASN-X-THR/SER tripeptides. J. Biol. Chem. 1983, 258, 11856-11863.
    • (1983) J. Biol. Chem. , vol.258 , pp. 11856-11863
    • Welply, J.K.1    Shenbagamurthi, P.2    Lennarz, W.J.3    Naider, F.4
  • 45
    • 0018908290 scopus 로고
    • 4-Dimethylasparagine), 8-lysine] vasopressin: The first 5-position neurohypophyseal hormone analogue to retain to retain significant antidiuretic potency
    • 4-Dimethylasparagine), 8-lysine]vasopressin: the first 5-position neurohypophyseal hormone analogue to retain to retain significant antidiuretic potency. J. Med. Chem. 1980, 23, 217-219.
    • (1980) J. Med. Chem. , vol.23 , pp. 217-219
    • Smith, C.W.1    Walter, R.2    Stavropoulos, G.3    Theodoropoulos, D.4
  • 46
    • 0018924390 scopus 로고
    • Oxytocin and lysine-vasopressin with N5,N5-dialkylglutamine in the 4 position: Effect of introducing sterically hindered groups into the hydrophilic cluster of neurohypophyseal hormones
    • Stahl, G. L.; Smith, C. W.; Walter, R.; Tsegenidis, T.; Stavropoulos, G.; Cordopatis, P.; Theodoropoulos, D. Oxytocin and lysine-vasopressin with N5,N5-dialkylglutamine in the 4 position: effect of introducing sterically hindered groups into the hydrophilic cluster of neurohypophyseal hormones. J. Med. Chem. 1980, 23, 213-217.
    • (1980) J. Med. Chem. , vol.23 , pp. 213-217
    • Stahl, G.L.1    Smith, C.W.2    Walter, R.3    Tsegenidis, T.4    Stavropoulos, G.5    Cordopatis, P.6    Theodoropoulos, D.7
  • 47
    • 0033018801 scopus 로고    scopus 로고
    • The design, synthesis, and biological evaluation of analogues of the serine-threonine protein phosphatase 1 and 2A selective inhibitor microcystin LA: Rational modifications imparting PP1 selectivity
    • Aggen, J. B.; Humphrey, J. M.; Gauss, C. M.; Huang, H. B.; Nairn, A. C.; Chamberlin, A. R. The design, synthesis, and biological evaluation of analogues of the serine-threonine protein phosphatase 1 and 2A selective inhibitor microcystin LA: rational modifications imparting PP1 selectivity. Bioorg. Med. Chem. 1999, 7, 543-564.
    • (1999) Bioorg. Med. Chem. , vol.7 , pp. 543-564
    • Aggen, J.B.1    Humphrey, J.M.2    Gauss, C.M.3    Huang, H.B.4    Nairn, A.C.5    Chamberlin, A.R.6
  • 50
    • 0015623118 scopus 로고
    • Synthetic luteinizing hormone releasing factor analogues Series of short chain amide LRF homologues converging to the amino terminus
    • Rivier, J.; Vale, W.; Burgus, R.; Ling, N.; Amoss, M.; Blackwell, R.; Guillemin, R. Synthetic luteinizing hormone releasing factor analogues Series of short chain amide LRF homologues converging to the amino terminus. J. Med. Chem. 1973, 16, 545-549.
    • (1973) J. Med. Chem. , vol.16 , pp. 545-549
    • Rivier, J.1    Vale, W.2    Burgus, R.3    Ling, N.4    Amoss, M.5    Blackwell, R.6    Guillemin, R.7
  • 51
    • 0014772602 scopus 로고
    • Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides
    • Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal. Biochem. 1970, 34, 595-598.
    • (1970) Anal. Biochem. , vol.34 , pp. 595-598
    • Kaiser, E.1    Colescott, R.L.2    Bossinger, C.D.3    Cook, P.I.4
  • 52
    • 0029837607 scopus 로고    scopus 로고
    • Peptide chemistry: Development of high-performance liquid chromatography and capillary zone electrophoresis
    • Miller, C.; Rivier, J. Peptide chemistry: Development of high-performance liquid chromatography and capillary zone electrophoresis. Biopolym. Pept. Sci. 1996, 40, 265-317.
    • (1996) Biopolym. Pept. Sci. , vol.40 , pp. 265-317
    • Miller, C.1    Rivier, J.2
  • 53
    • 0028234916 scopus 로고
    • A new general solid-phase method for the synthesis of backbone-to-backbone cyclized peptides
    • Kaljuste, K.; Undén, A. A new general solid-phase method for the synthesis of backbone-to-backbone cyclized peptides. Int. J. Pept. Protein Res. 1994, 43, 505-511.
    • (1994) Int. J. Pept. Protein Res. , vol.43 , pp. 505-511
    • Kaljuste, K.1    Undén, A.2
  • 54
    • 37049061588 scopus 로고
    • Substituted diphenylmethyl protecting groups in peptide synthesis
    • The Chaucer Press: Ltd.: London
    • Hanson, R. W.; Law, H. D. Substituted diphenylmethyl protecting groups in peptide synthesis. Journal of The Chemical Society; The Chaucer Press: Ltd.: London, 1965; pp 7285-7297.
    • (1965) Journal of the Chemical Society , pp. 7285-7297
    • Hanson, R.W.1    Law, H.D.2
  • 55
    • 0000749379 scopus 로고
    • Coupling N-methylated amino acids using PyBroP1 and PyCloP halogenophosphonium salts: Mechanism and fields of application
    • Coste, J.; Frérot, E.; Jouin, P. Coupling N-methylated amino acids using PyBroP1 and PyCloP halogenophosphonium salts: mechanism and fields of application. J. Org. Chem. 1994, 59, 2437-2446.
    • (1994) J. Org. Chem. , vol.59 , pp. 2437-2446
    • Coste, J.1    Frérot, E.2    Jouin, P.3
  • 56
    • 0028049114 scopus 로고
    • Gonadotropin-releasing hormone causes transcriptional stimulation followed by desensitization of the glycoprotein hormone alpha promoter in transfected alpha T3 gonadotrope cells
    • Kay, T. W.; Chedrese, P. J.; Jameson, J. L. Gonadotropin-releasing hormone causes transcriptional stimulation followed by desensitization of the glycoprotein hormone alpha promoter in transfected alpha T3 gonadotrope cells. Endocrinology 1994, 134, 568-573.
    • (1994) Endocrinology , vol.134 , pp. 568-573
    • Kay, T.W.1    Chedrese, P.J.2    Jameson, J.L.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.