메뉴 건너뛰기




Volumn 3, Issue 4, 2012, Pages 337-341

Discovery of BMS-846372, a potent and orally active human CGRP receptor antagonist for the treatment of migraine

Author keywords

antagonist; CGRP; CGRP receptor; migraine

Indexed keywords

BMS 846372; CALCITONIN GENE RELATED PEPTIDE; CALCITONIN GENE RELATED PEPTIDE RECEPTOR ANTAGONIST; UNCLASSIFIED DRUG;

EID: 84859771560     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml300021s     Document Type: Article
Times cited : (32)

References (34)
  • 1
    • 0034883732 scopus 로고    scopus 로고
    • Prevalence and burden of migraine in the United States: Data from the American Migraine Study II
    • DOI 10.1046/j.1526-4610.2001.041007646.x
    • Lipton, R. B.; Stewart, W. F.; Diamond, S.; Diamond, M. L.; Reed, M. Prevalence and burden of migraine in the United States: Data from the American Migraine Study II Headache 2001, 41, 646-657 (Pubitemid 32777747)
    • (2001) Headache , vol.41 , Issue.7 , pp. 646-657
    • Lipton, R.B.1    Stewart, W.F.2    Diamond, S.3    Diamond, M.L.4    Reed, M.5
  • 2
    • 84944661463 scopus 로고
    • Mechanism of migraine headache and the action of ergotamine tartrate
    • Graham, J. P.; Wolff, H. G. Mechanism of migraine headache and the action of ergotamine tartrate Arch. Neurol. Psychiatry 1938, 39, 737-763
    • (1938) Arch. Neurol. Psychiatry , vol.39 , pp. 737-763
    • Graham, J.P.1    Wolff, H.G.2
  • 3
    • 67649598903 scopus 로고    scopus 로고
    • Origin of pain in migraine: Evidence for peripheral sensitisation
    • Olesen, J.; Burstein, R.; Ashina, M.; Tfelt-Hansen, P. Origin of pain in migraine: Evidence for peripheral sensitisation Lancet Neurol. 2009, 8, 679-690
    • (2009) Lancet Neurol. , vol.8 , pp. 679-690
    • Olesen, J.1    Burstein, R.2    Ashina, M.3    Tfelt-Hansen, P.4
  • 7
    • 0030665019 scopus 로고    scopus 로고
    • Neuroanatomical localization, pharmacological characterization and functions of CGRP, related peptides and their receptors
    • DOI 10.1016/S0149-7634(96)00023-1, PII S0149763496000231
    • van Rossum, D.; Hanisch, U. K.; Quirion, R. Neuroanatomical localization, pharmacological characterization and functions of CGRP, related peptides and their receptors Neurosci. Biobehav. Rev. 1997, 21, 649-678 (Pubitemid 27458805)
    • (1997) Neuroscience and Biobehavioral Reviews , vol.21 , Issue.5 , pp. 649-678
    • Van Rossum, D.1    Hanisch, U.-K.2    Quirion, R.3
  • 8
    • 30044452563 scopus 로고    scopus 로고
    • Calcitonin gene-related peptide antagonists as treatments of migraine and other primary headaches
    • DOI 10.2165/00003495-200565180-00002
    • Goadsby, P. J. Calcitonin gene-related peptide antagonists as treatments of migraine and other primary headaches Drugs 2005, 65, 2557-2567 (Pubitemid 43049952)
    • (2005) Drugs , vol.65 , Issue.18 , pp. 2557-2567
    • Goadsby, P.J.1
  • 9
    • 4043057222 scopus 로고    scopus 로고
    • Blockade of CGRP receptors in the intracranial vasculature: A new target in the treatment of headache
    • DOI 10.1111/j.1468-2982.2003.00719.x
    • Edvinsson, L. Blockade of CGRP receptors in the intracranial vasculature: A new target in the treatment of headache Cephalalgia 2004, 24, 611-622 (Pubitemid 39061250)
    • (2004) Cephalalgia , vol.24 , Issue.8 , pp. 611-622
    • Edvinsson, L.1
  • 10
    • 0035340714 scopus 로고    scopus 로고
    • Neurogenic inflammation in the context of migraine
    • DOI 10.1002/jemt.1081
    • Williamson, D. J.; Hargreaves, R. J. Neurogenic inflammation in the context of migraine Microsc. Res. Tech. 2001, 53, 167-178 (Pubitemid 32378031)
    • (2001) Microscopy Research and Technique , vol.53 , Issue.3 , pp. 167-178
    • Williamson, D.J.1    Hargreaves, R.J.2
  • 11
    • 0025143541 scopus 로고
    • Vasoactive peptide release in the extracerebral circulation of humans during migraine headache
    • DOI 10.1002/ana.410280213
    • Goadsby, P. J.; Edvinsson, L; Ekman, R. Vasoactive peptide release in the extracerebral circulation of humans during migraine headache Ann. Neurol. 1990, 28, 183-187 (Pubitemid 20244522)
    • (1990) Annals of Neurology , vol.28 , Issue.2 , pp. 183-187
    • Goadsby, P.J.1    Edvinsson, L.2    Ekman, R.3
  • 12
    • 0027509161 scopus 로고
    • The trigeminovascular system and migraine: Studies characterizing cerebrovascular and neuropeptide changes seen in humans and cats
    • DOI 10.1002/ana.410330109
    • Goadsby, P. J.; Edvinsson, L. The trigeminovascular system and migraine. Studies characterizing cerebrovascular and neuropeptide changes seen in humans and cats Ann. Neurol. 1993, 33, 48-56 (Pubitemid 23009909)
    • (1993) Annals of Neurology , vol.33 , Issue.1 , pp. 48-56
    • Goadsby, P.J.1    Edvinsson, L.2
  • 13
    • 67049108842 scopus 로고    scopus 로고
    • Calcitonin gene-related peptide: An update on the biology
    • Recober, A.; Russo, A. F. Calcitonin gene-related peptide: An update on the biology Curr. Opin. Neurol. 2009, 22, 241-246
    • (2009) Curr. Opin. Neurol. , vol.22 , pp. 241-246
    • Recober, A.1    Russo, A.F.2
  • 15
    • 84859737733 scopus 로고    scopus 로고
    • IDDB. Thomson Scientific reportsthat the development of BIBN4096BS has been discontinued.
    • IDDB. Thomson Scientific reportsthat the development of BIBN4096BS has been discontinued.
  • 16
    • 36148978527 scopus 로고    scopus 로고
    • Potent, orally bioavailable calcitonin gene-related peptide receptor antagonists for the treatment of migraine: Discovery of N-(3R,6S)-6-(2,3- difluorophenyl)-2-oxo-1-(2,2,2-trifluoroethyl)azepan-3-yl-4-(2-oxo-2, 3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide (MK-0974)
    • DOI 10.1021/jm070668p
    • Paone, D. V.; Shaw, A. W.; Nguyen, D. N.; Burgey, C. S.; Deng, J. Z.; Kane, S. A.; Koblan, K. S.; Salvatore, C. A.; Mosser, S. D.; Johnston, V. K.; Wong, B. K.; Miller-Stein, C. M.; Hershey, J. C.; Graham, S. L.; Vacca, J. P.; Williams, T. M. Potent, orally bioavailable calcitonin gene-related peptide receptor antagonists for the treatment of migraine: Discovery of N -[(3 R,6 S)-6-(2,3-difluorophenyl)-2-oxo-1- (2,2,2-trifluoroethyl)azepan-3-yl]-4- (2-oxo-2,3-dihydro-1 H -imidazo[4,5-b]pyridin- 1-yl)piperidine-1-carboxamide (MK-0974) J. Med. Chem. 2007, 50, 5564-5567 (Pubitemid 350106011)
    • (2007) Journal of Medicinal Chemistry , vol.50 , Issue.23 , pp. 5564-5567
    • Paone, D.V.1    Shaw, A.W.2    Nguyen, D.N.3    Burgey, C.S.4    Deng, J.Z.5    Kane, S.A.6    Koblan, K.S.7    Salvatore, C.A.8    Mosser, S.D.9    Johnston, V.K.10    Wong, B.K.11    Miller-Stein, C.M.12    Hershey, J.C.13    Graham, S.L.14    Vacca, J.P.15    Williams, T.M.16
  • 18
    • 78650963413 scopus 로고    scopus 로고
    • Excellent tolerability but relatively low initial clinical efficacy of telcagepant in migraine headache
    • Merck publicly announced the discontinuation of further development of telcagepant, but no specific reasons were given
    • Tfelt-Hansen, P. Excellent tolerability but relatively low initial clinical efficacy of telcagepant in migraine headache Headache 2011, 51, 118-123 Merck publicly announced the discontinuation of further development of telcagepant, but no specific reasons were given
    • (2011) Headache , vol.51 , pp. 118-123
    • Tfelt-Hansen, P.1
  • 19
    • 50249096199 scopus 로고    scopus 로고
    • Discovery of (R)-4-(8-fluoro-2-oxo-1,2-dihydroquinazolin-3(4 H)-yl)- N -(3-(7-methyl-1H-indazol-5-yl)-1-oxo-1-(4-(piperidin-1-yl)piperidin-1-yl) propan-2-yl)piperidine-1-carboxamide (BMS-694153): A potent antagonist of the human calcitonin gene- related peptide receptor for migraine with rapid and efficient intranasal exposure
    • Degnan, A. P.; Chaturvedula, P. V.; Conway, C. M.; Cook, D.; Davis, C. D.; Denton, R.; Han, X.; Macci, R.; Mathias, N. R.; Moench, P.; Pin, S. S.; Ren, S. X.; Schartman, R.; Signor, L.; Thalody, G.; Widmann, K. A.; Xu, C.; Macor, J. E.; Dubowchik, G. M. Discovery of (R)-4-(8-fluoro-2-oxo-1,2- dihydroquinazolin-3(4 H)-yl)- N -(3-(7-methyl-1H-indazol-5-yl)-1-oxo-1-(4- (piperidin-1-yl)piperidin-1-yl)propan-2-yl)piperidine-1-carboxamide (BMS-694153): A potent antagonist of the human calcitonin gene- related peptide receptor for migraine with rapid and efficient intranasal exposure J. Med. Chem. 2008, 51, 4858-4861
    • (2008) J. Med. Chem. , vol.51 , pp. 4858-4861
    • Degnan, A.P.1    Chaturvedula, P.V.2    Conway, C.M.3    Cook, D.4    Davis, C.D.5    Denton, R.6    Han, X.7    MacCi, R.8    Mathias, N.R.9    Moench, P.10    Pin, S.S.11    Ren, S.X.12    Schartman, R.13    Signor, L.14    Thalody, G.15    Widmann, K.A.16    Xu, C.17    MacOr, J.E.18    Dubowchik, G.M.19
  • 20
    • 84862777374 scopus 로고    scopus 로고
    • Calcitonin gene-related peptide (CGRP) receptor antagonists: Pyridine as a replacement for a core amide group
    • in press. DOI: doi.org/10.1016/j.bmcl.2012.02.065.
    • Luo, G.; Chen, L.; Civiello, R.; Pin, S. S.; Xu, C.; Kostich, W.; Kelley, M.; Conway, C. M.; Macor, J. E.; Dubowchik, G. M. Calcitonin gene-related peptide (CGRP) receptor antagonists: Pyridine as a replacement for a core amide group. Bioorg. Med. Chem. Lett. 2012, in press. DOI: doi.org/10.1016/j.bmcl. 2012.02.065.
    • (2012) Bioorg. Med. Chem. Lett.
    • Luo, G.1    Chen, L.2    Civiello, R.3    Pin, S.S.4    Xu, C.5    Kostich, W.6    Kelley, M.7    Conway, C.M.8    MacOr, J.E.9    Dubowchik, G.M.10
  • 23
    • 37049085667 scopus 로고
    • The synthesis and transition temperatures of some 4,4″-dialkyl- and 4,4″-alkoxyalkyl-1,1′:4′,1″-terphenyls with 2,3- or 2′,3′-difluoro substituents and of their biphenyl analogues
    • Gray, G. W.; Hird; Lacey, D.; Toyne, K. J. The synthesis and transition temperatures of some 4,4″-dialkyl- and 4,4″-alkoxyalkyl-1,1′: 4′,1″-terphenyls with 2,3- or 2′,3′-difluoro substituents and of their biphenyl analogues J. Chem. Soc. Perkin Trans. 2: Phys. Org. Chem. 1989, 2041-2054
    • (1989) J. Chem. Soc. Perkin Trans. 2: Phys. Org. Chem. , pp. 2041-2054
    • Gray, G.W.1    Hird2    Lacey, D.3    Toyne, K.J.4
  • 24
    • 0035861034 scopus 로고    scopus 로고
    • Tandem catalysis: The sequential mediation of olefin metathesis, hydrogenation, and hydrogen transfer with single-component Ru complexes
    • DOI 10.1021/ja016431e
    • Louie, J.; Bielawski, C. W.; Grubbs, R. H. Tandem catalysis: The sequential mediation of olefin metathesis, hydrogenation, and hydrogen transfer with single-component Ru complexes J. Am. Chem. Soc. 2001, 123, 11312-11313 (Pubitemid 33065377)
    • (2001) Journal of the American Chemical Society , vol.123 , Issue.45 , pp. 11312-11313
    • Louie, J.1    Bielawski, C.W.2    Grubbs, R.H.3
  • 25
    • 0001459128 scopus 로고
    • Arene-metal complexes in organic synthesis. Synthesis of acorenone and acorenone B
    • Semmelhack, M. F.; Yamashita, A. Arene-metal complexes in organic synthesis. Synthesis of acorenone and acorenone B J. Am. Chem. Soc. 1980, 102, 5924-5926
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 5924-5926
    • Semmelhack, M.F.1    Yamashita, A.2
  • 26
    • 0037025928 scopus 로고    scopus 로고
    • CP-263,114 synthetic studies. Construction of an isotwistane ring system via rhodium carbenoid C-H insertion
    • DOI 10.1016/S0040-4020(02)00664-6, PII S0040402002006646
    • Spiegel, D. A.; Njardarson, J. T.; Wood., J. L. CP-263,114 Synthetic studies. Construction of an isotwistane ring system via rhodium carbenoid C-H insertion Tetrahedron 2002, 58, 6545-6554 (Pubitemid 34879692)
    • (2002) Tetrahedron , vol.58 , Issue.32 , pp. 6545-6554
    • Spiegel, D.A.1    Njardarson, J.T.2    Wood, J.L.3
  • 27
    • 0041336779 scopus 로고    scopus 로고
    • Sequential amination/annulation/aromatization reaction of carbonyl compounds and propargylamine: A new one-pot approach to functionalized pyridines
    • DOI 10.1021/jo0347260
    • Abbiati, G.; Arcadi, A.; Bianchi, G.; Giuseppe, S. D.; Marinelli, F.; Rossi, E. Sequential amination/annulation/aromatization reaction of carbonyl compounds and propargylamine: A new one-pot approach to functionalized pyridines J. Org. Chem. 2003, 68, 6959-6966 (Pubitemid 37071775)
    • (2003) Journal of Organic Chemistry , vol.68 , Issue.18 , pp. 6959-6966
    • Abbiati, G.1    Arcadi, A.2    Bianchi, G.3    Di Giuseppe, S.4    Marinelli, F.5    Rossi, E.6
  • 28
    • 84859737731 scopus 로고    scopus 로고
    • See the Supporting Information for details. The absolute configuration was eventually proved by chiral synthesis of BMS-846372: Manuscript in preparation.
    • See the Supporting Information for details. The absolute configuration was eventually proved by chiral synthesis of BMS-846372: Leahy, D.; Org. Lett. Manuscript in preparation.
    • Org. Lett.
    • Leahy, D.1
  • 29
    • 33947146141 scopus 로고    scopus 로고
    • Conjugate addition of 2- and 4-pyridylcuprates: An expeditious asymmetric synthesis of natural (-)-evoninic acid
    • Spivey, A. C.; Shukla, L.; Hayler, J. F. Conjugate addition of 2- and 4-pyridylcuprates: An expeditious asymmetric synthesis of natural (-)-evoninic acid Org. Lett. 2007, 9, 891-894
    • (2007) Org. Lett. , vol.9 , pp. 891-894
    • Spivey, A.C.1    Shukla, L.2    Hayler, J.F.3
  • 31
    • 26444554565 scopus 로고    scopus 로고
    • Enantioselective synthesis of (+)(R)- and (-)(S)-nicotine based on Ir-catalysed allylic amination
    • Welter, C.; Moreno, R. M.; Streiff, S.; Helmchen, G. Enantioselective synthesis of (+)(R)- and (-)(S)-nicotine based on Ir-catalysed allylic amination Org. Biomol. Chem. 2005, 3, 3266-6268
    • (2005) Org. Biomol. Chem. , vol.3 , pp. 3266-6268
    • Welter, C.1    Moreno, R.M.2    Streiff, S.3    Helmchen, G.4
  • 32
    • 0347418212 scopus 로고    scopus 로고
    • First asymmetric total synthesis of (-)-(R)- and (+)-(S)-geibalansine
    • DOI 10.1016/j.tetasy.2003.09.052
    • Morel, A. F.; Larghi, E. L. First asymmetric total synthesis of (-)-(R)- and (+)-(S)-geibalansine Tetrahedron: Asymmetry 2004, 15, 9-10 (Pubitemid 38032726)
    • (2004) Tetrahedron Asymmetry , vol.15 , Issue.1 , pp. 9-10
    • Morel, A.F.1    Larghi, E.L.2
  • 33
    • 84989536113 scopus 로고
    • Highly enantioselective epoxidation catalysts derived from 1,2-diaminocyclohexane
    • The catalyst used here was an equal mixture of commercially available enantiomers
    • Jacobson, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. Highly enantioselective epoxidation catalysts derived from 1,2-diaminocyclohexane J. Am. Chem. Soc. 1991, 113, 7063-7064 The catalyst used here was an equal mixture of commercially available enantiomers
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 7063-7064
    • Jacobson, E.N.1    Zhang, W.2    Muci, A.R.3    Ecker, J.R.4    Deng, L.5
  • 34
    • 84859761001 scopus 로고    scopus 로고
    • To be published.
    • Keavy, D.; To be published.
    • Keavy, D.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.