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Volumn 46, Issue 16, 2003, Pages 3508-3513

Stereoselective preparation of N-[(R,R)-(E)-1-(3,4-dichlorobenzyl)-3-(2-oxoazepan-3-yl)carbamoyl]allyl- N-methyl-3,5-bis(trifluoromethyl)benzamide, a potent and orally active dual neurokinin NK1/NK2 receptor antagonist

Author keywords

[No Author keywords available]

Indexed keywords

BENZAMIDE DERIVATIVE; DNK 333; N [1 (3,4 DICHLOROBENZYL) 3 (2 OXOAZEPAN 3 YL)CARBAMOYL]ALLYL N METHYL 3,5 BIS(TRIFLUOROMETHYL)BENZAMIDE; NEUROKININ 1 RECEPTOR; NEUROKININ 1 RECEPTOR ANTAGONIST; NEUROKININ 2 RECEPTOR; NEUROKININ 2 RECEPTOR ANTAGONIST; NEUROKININ A; SUBSTANCE P; UNCLASSIFIED DRUG;

EID: 0041842669     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030786m     Document Type: Article
Times cited : (9)

References (32)
  • 2
    • 0028589913 scopus 로고
    • Receptors and antagonists for substance P and related peptides
    • (b) Regoli, D.; Boudon, A., Fauchére, J.-L. Receptors and antagonists for substance P and related peptides. Pharmacol. Rev. 1994, 46 (4), 551-599.
    • (1994) Pharmacol. Rev. , vol.46 , Issue.4 , pp. 551-599
    • Regoli, D.1    Boudon, A.2    Fauchére, J.-L.3
  • 3
    • 0003155094 scopus 로고
    • History of tachykinin peptides
    • Buck, S. H., Eds.; Humana: Totowa, NJ
    • (c) Maggio, J. E.; Mantyh, P. W. History of Tachykinin Peptides. In The Tachykinin Receptors; Buck, S. H., Eds.; Humana: Totowa, NJ, 1994; pp 1-21.
    • (1994) The Tachykinin Receptors , pp. 1-21
    • Maggio, J.E.1    Mantyh, P.W.2
  • 4
    • 0026100201 scopus 로고
    • Mammalian tachykinin receptors
    • Nakanishi, S. Mammalian tachykinin receptors. Annu. Rev. Neurosci. 1994, 14, 123-136.
    • (1994) Annu. Rev. Neurosci. , vol.14 , pp. 123-136
    • Nakanishi, S.1
  • 6
    • 0000949253 scopus 로고
    • Autoradiographic localization of receptors in peripheral tissues
    • Buck, S. H., Eds.; Humana: Totowa, NJ
    • (a) Burcher, E.; Mussap, C. J.; Stephenson, J. A. Autoradiographic localization of receptors in peripheral tissues. In The Tachykinin Receptors; Buck, S. H., Eds.; Humana: Totowa, NJ, 1994; pp 125-163.
    • (1994) The Tachykinin Receptors , pp. 125-163
    • Burcher, E.1    Mussap, C.J.2    Stephenson, J.A.3
  • 7
    • 0002754136 scopus 로고
    • Molecular biology of receptors
    • Buck, S. H., Eds.; Humana: Totowa, NJ
    • (b) Krause, J. E.; Blount, P.; Sachais, B. S. Molecular Biology of Receptors. In The Tachykinin Receptors; Buck, S. H., Eds.; Humana: Totowa, NJ, 1994, pp 165-218.
    • (1994) The Tachykinin Receptors , pp. 165-218
    • Krause, J.E.1    Blount, P.2    Sachais, B.S.3
  • 9
    • 0028967773 scopus 로고
    • Tachykinin antagonists in development
    • (b) Kucharczyk, N. Tachykinin antagonists in development. Expert Opin. Invest. Drugs 1995, 4 (4), 299-311.
    • (1995) Expert Opin. Invest. Drugs , vol.4 , Issue.4 , pp. 299-311
    • Kucharczyk, N.1
  • 10
    • 0030849519 scopus 로고    scopus 로고
    • Neurokinin receptor antagonists
    • (c) Elliott, J.; Seward, E. M. Neurokinin receptor antagonists. Expert Opin. Ther. Pat. 1997, 7 (1), 43-54.
    • (1997) Expert Opin. Ther. Pat. , vol.7 , Issue.1 , pp. 43-54
    • Elliott, J.1    Seward, E.M.2
  • 11
    • 0030722614 scopus 로고    scopus 로고
    • Neurokinin-receptor antagonists: Pharmacological tools and therapeutic drugs
    • (d) Longmore, J.; Hill, R. G.; Hargreaves, R. J. Neurokinin-receptor antagonists: pharmacological tools and therapeutic drugs. Can. J. Physiol. Pharmacol. 1997, 75, 612-621.
    • (1997) Can. J. Physiol. Pharmacol. , vol.75 , pp. 612-621
    • Longmore, J.1    Hill, R.G.2    Hargreaves, R.J.3
  • 12
    • 0001992161 scopus 로고    scopus 로고
    • Neurokinin antagonists as potential therapies for inflammation and rheumatoid arthritis
    • (e) von Sprecher, A.; Gerspacher, M.; Anderson, G. P. Neurokinin antagonists as potential therapies for inflammation and rheumatoid arthritis. Drugs 1998, 1 (1), 73-91.
    • (1998) Drugs , vol.1 , Issue.1 , pp. 73-91
    • Von Sprecher, A.1    Gerspacher, M.2    Anderson, G.P.3
  • 14
    • 0030431038 scopus 로고    scopus 로고
    • In vitro and in vivo characterisation of MDL 105,212A, a nonpeptide NK-1/NK-2 tachykinin receptor antagonists
    • (b) Kudlacz, E. M.; Scott, A.; Shatzer, S. A.; et al. In vitro and in vivo characterisation of MDL 105,212A, a nonpeptide NK-1/NK-2 tachykinin receptor antagonists. J. Pharmacol. Exp. Ther. 1996, 277, 840-851.
    • (1996) J. Pharmacol. Exp. Ther. , vol.277 , pp. 840-851
    • Kudlacz, E.M.1    Scott, A.2    Shatzer, S.A.3
  • 18
    • 0035935196 scopus 로고    scopus 로고
    • Discovery of novel, orally active dual NK1/NK2 antagonists
    • (f) Bernstein, P. R.; Aharony, D.; Albert, J. S.; et al. Discovery of novel, orally active dual NK1/NK2 antagonists. Bioorg. Med. Chem. Lett. 2001, 11, 2769-2773.
    • (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 2769-2773
    • Bernstein, P.R.1    Aharony, D.2    Albert, J.S.3
  • 20
    • 0036659628 scopus 로고    scopus 로고
    • Synthetic studies for the novel morpholine- and oxazolidine-based tachykinin receptor antagonists
    • (h) Nishi, T. Synthetic studies for the novel morpholine- and oxazolidine-based tachykinin receptor antagonists. Yuki Gosei Kagaku Kyokaishi 2002, 60 (7), 657-667.
    • (2002) Yuki Gosei Kagaku Kyokaishi , vol.60 , Issue.7 , pp. 657-667
    • Nishi, T.1
  • 21
    • 0027049669 scopus 로고
    • Novel therapeutic strategies for the treatment of human bronchial asthma
    • (a) Ford-Hutchinson, A. W.; Rodger, I. W.; Jones, T. R. Drug News Perspect. Novel therapeutic strategies for the treatment of human bronchial asthma. 1992, 5 (9), 542-549.
    • (1992) Drug News Perspect. , vol.5 , Issue.9 , pp. 542-549
    • Ford-Hutchinson, A.W.1    Rodger, I.W.2    Jones, T.R.3
  • 23
    • 0030874037 scopus 로고    scopus 로고
    • The role of tachykinin receptor antagonists in the prevention of bronchial hyperresponsiveness, airway inflammation, and cough
    • (c) Advenier, C.; Lagente, V.; Boichot, E. The role of tachykinin receptor antagonists in the prevention of bronchial hyperresponsiveness, airway inflammation, and cough. Eur. Respir. J. 1997, 10, 1892-1906.
    • (1997) Eur. Respir. J. , vol.10 , pp. 1892-1906
    • Advenier, C.1    Lagente, V.2    Boichot, E.3
  • 25
    • 0026628389 scopus 로고
    • Effects of FK-224, a novel compound NK-1 and NK-2 receptor antagonist, on airway constriction and airway edema induced by neurokinins and sensory nerve stimulation in guinea-pigs
    • (a) Murai, M.; Morimoto, H.; Maeda, Y.; Kiyotoh, S.; Nishikawa, M.; Fujii, T. Effects of FK-224, a novel compound NK-1 and NK-2 receptor antagonist, on airway constriction and airway edema induced by neurokinins and sensory nerve stimulation in guinea-pigs. J. Pharmacol. Exp. Ther. 1992, 262, 403-408.
    • (1992) J. Pharmacol. Exp. Ther. , vol.262 , pp. 403-408
    • Murai, M.1    Morimoto, H.2    Maeda, Y.3    Kiyotoh, S.4    Nishikawa, M.5    Fujii, T.6
  • 26
    • 0029951892 scopus 로고    scopus 로고
    • The effect of inhaled FK-224, a tachykinin NK-1 and NK-2 receptor antagonist on neurokinin A-induced bronchoconstriction in asthmatics
    • (b) Joos, G. F.; Van Schoor, J.; Kips, J. C.; Pauwels, R. A. The effect of inhaled FK-224, a tachykinin NK-1 and NK-2 receptor antagonist on neurokinin A-induced bronchoconstriction in asthmatics. Am. J. Respir. Crit. Care Med. 1996, 153, 1781-1784.
    • (1996) Am. J. Respir. Crit. Care Med. , vol.153 , pp. 1781-1784
    • Joos, G.F.1    Van Schoor, J.2    Kips, J.C.3    Pauwels, R.A.4
  • 27
    • 0035381322 scopus 로고    scopus 로고
    • Tachykinin receptor antagonists: Potential in airways diseases
    • (c) Joos, G. F.; Pauwels, R. A. Tachykinin receptor antagonists: potential in airways diseases. Curr. Opin. Pharmacol. 2001, 1 (3), 235-241.
    • (2001) Curr. Opin. Pharmacol. , vol.1 , Issue.3 , pp. 235-241
    • Joos, G.F.1    Pauwels, R.A.2
  • 29
    • 0011528389 scopus 로고
    • Silicon in organic synthesis; an improved preparation of α,β-unsaturated acids from carbonyl compounds
    • Lombardo, L.; Taylor, R. J. K. Silicon in organic synthesis; an improved preparation of α,β-unsaturated acids from carbonyl compounds. Synthesis 1978, 2, 131.
    • (1978) Synthesis , vol.2 , pp. 131
    • Lombardo, L.1    Taylor, R.J.K.2
  • 30
    • 0030714029 scopus 로고    scopus 로고
    • Preparation, characterisation, DNA binding, and in vitro cytotoxicity of the enantiomers of the platinum (II) complexes N-methyl-, N-ethyl- and N,N-dimethyl-(R)-and (S)-3-aminohexahydroazepinedichloroplatinum (II)
    • Rezler, E. M.; Fenton, R. R.; Esdale, W. J.; McKeage, M. J.; Russell, P. J.; Hambley, T. W. Preparation, characterisation, DNA binding, and in vitro cytotoxicity of the enantiomers of the platinum (II) complexes N-methyl-, N-ethyl- and N,N-dimethyl-(R)-and (S)-3-aminohexahydroazepinedichloroplatinum (II). J. Med. Chem. 1997, 40 (22), 3508-3515. L-α-Amino-ε-caprolactam is commercially available from Fluka Chemie AG, CH-9471 Buchs, Switzerland.
    • (1997) J. Med. Chem. , vol.40 , Issue.22 , pp. 3508-3515
    • Rezler, E.M.1    Fenton, R.R.2    Esdale, W.J.3    McKeage, M.J.4    Russell, P.J.5    Hambley, T.W.6
  • 31
    • 0041406265 scopus 로고    scopus 로고
    • Preparation of butenoic acids derivatives and their use in the treatment of rhinitis. Patent WO01/85696, 2001
    • Preparation of rac-3: Gerspacher, M.; Hoshiko, K. Preparation of butenoic acids derivatives and their use in the treatment of rhinitis. Patent WO01/85696, 2001.
    • Gerspacher, M.1    Hoshiko, K.2


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