[11C]MK-4232: The first positron emission tomography tracer for the calcitonin gene-related peptide receptor

ACS Medicinal Chemistry Letters

Volumn 4, Issue 9, 2013, Pages 863-868

  Bell, Ian M ^a   Gallicchio, Steven N ^a   Stump, Craig A ^a   Bruno, Joseph G ^a   Fan, Hong ^a   Gantert, Liza T ^a   Hostetler, Eric D ^a   Kemmerer, Amanda L ^a   McWherter, Melody ^a   Moore, Eric L ^a   Mosser, Scott D ^a   Purcell, Mona L ^a   Riffel, Kerry ^a   Salvatore, Christopher A ^a   Sanabria Bohórquez, Sandra ^a   Staas, Donnette D ^a   White, Rebecca B ^a   Williams, Mangay ^a   Zartman, C Blair ^a   Cook, Jacquelynn J ^a   Hargreaves, Richard J ^a   Kane, Stefanie A ^a   Graham, Samuel L ^a   Selnick, Harold G ^a   more..

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

calcitonin gene related peptide receptor; MK 4232; positron emission tomography

Indexed keywords

CALCITONIN GENE RELATED PEPTIDE RECEPTOR; MK 4232; MK 4232 C 11; TELCAGEPANT; TRACER; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CEREBELLUM; CONTROLLED STUDY; DRUG IDENTIFICATION; HUMAN; HUMAN CELL; IN VIVO STUDY; LIPOPHILICITY; MEMBRANE PERMEABILITY; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; SYNTHESIS; WHITE MATTER;

EID: 84884274090     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml400199p     Document Type: Article

References (20)

1. Stovner, L. J.; Hagen, K.; Jensen, R.; Katsarava, Z.; Lipton, R. B.; Scher, A. I.; Steiner, T. J.; Zwart, J. A. The global burden of headache: a documentation of headache prevalence and disability worldwide Cephalalgia 2007, 27, 193-210
2. Ho, T. W.; Edvinsson, L.; Goadsby, P. J. CGRP and its receptors provide new insights into migraine pathophysiology Nat. Rev. Neurol. 2010, 6, 573-582
3. Durham, P. L. Inhibition of calcitonin gene-related peptide function: a promising strategy for treating migraine Headache 2008, 48, 1269-1275
4. Olesen, J.; Diener, H.-C.; Husstedt, I. W.; Goadsby, P. J.; Hall, D.; Meier, U.; Pollentier, S.; Lesko, L. M. Calcitonin gene-related peptide receptor antagonist BIBN 4096 BS for the acute treatment of migraine N. Engl. J. Med. 2004, 350, 1104-1110
5. Ho, T. W.; Ferrari, M. D.; Dodick, D. W.; Galet, V.; Kost, J.; Fan, X.; Leibensperger, H.; Froman, S.; Assaid, C.; Lines, C.; Koppen, H.; Winner, P. K. Efficacy and tolerability of MK-0974 (telcagepant), a new oral antagonist of calcitonin gene-related peptide receptor, compared with zolmitriptan for acute migraine: a randomised, placebo-controlled, parallel-treatment trial Lancet 2008, 372, 2115-2123
6. Hewitt, D. J.; Aurora, S. K.; Dodick, D. W.; Goadsby, P. J.; Ge, Y.; Bachman, R.; Taraborelli, D.; Fan, X.; Assaid, C.; Lines, C.; Ho, T. W. Randomized controlled trial of the CGRP receptor antagonist MK-3207 in the acute treatment of migraine Cephalalgia 2011, 31, 712-722
7. Diener, H.-C.; Barbanti, P.; Dahlof, C.; Reuter, U.; Habeck, J.; Podhorna, J. BI 44370 TA, an oral CGRP antagonist for the treatment of acute migraine attacks: results from a phase II study Cephalalgia 2011, 31, 573-584
8. Edvinsson, L.; Ho, T. W. CGRP receptor antagonism and migraine Neurotherapeutics 2010, 7, 164-175
9. 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
10. Bell, I. M.; Gallicchio, S. N.; Wood, M. R.; Quigley, A. G.; Stump, C. A.; Zartman, C. B.; Fay, J. F.; Li, C.-C.; Lynch, J. L.; Moore, E. L.; Mosser, S. D.; Prueksaritanont, T.; Regan, C. P.; Roller, S.; Salvatore, C. A.; Kane, S. A.; Vacca, J. P.; Selnick, H. G. Discovery of MK-3207: a highly potent, orally bioavailable CGRP receptor antagonist ACS Med. Chem. Lett. 2010, 1, 24-29
11. Salvatore, C. A.; Hershey, J. C.; Corcoran, H. A.; Fay, J. F.; Johnston, V. K.; Moore, E. L.; Mosser, S. D.; Burgey, C. S.; Paone, D. V.; Shaw, A. W.; Graham, S. L.; Vacca, J. P.; Williams, T. M.; Koblan, K. S.; Kane, S. A. Pharmacological characterization of MK-0974 [ 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], a potent and orally active calcitonin gene-related peptide receptor antagonist for the treatment of migraine J. Pharmacol. Exp. Ther. 2008, 324, 416-421
12. Salvatore, C. A.; Moore, E. L.; Calamari, A.; Cook, J. J.; Michener, M. S.; O'Malley, S.; Miller, P. J.; Sur, C.; Williams, D. L.; Zeng, Z.; Danziger, A.; Lynch, J. J.; Regan, C. P.; Fay, J. F.; Tang, Y. S.; Li, C.-C.; Pudvah, N. T.; White, R. B.; Bell, I. M.; Gallicchio, S. N.; Graham, S. L.; Selnick, H. G.; Vacca, J. P.; Kane, S. A. Pharmacological properties of 2-[(8 R)-8-(3,5-difluorophenyl)-10-oxo-6,9-diazaspiro[4.5]dec-9-yl]- N -[(2 R)-2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2, 3′-pyrrolo[2,3- b ]pyridin]-5-yl]acetamide (MK-3207), a potent and orally active calcitonin gene-related peptide receptor antagonist J. Pharmacol. Exp. Ther. 2010, 333, 152-160
13. Eckelman, W. C.; Gibson, R. E.; Rzeszotarski, W. J.; Vieras, F.; Mazaitis, J. K.; Francis, B.; Reba, W. C. The Design of Receptor Binding Radiotracers. In Principles of Radiopharmacology; Colombetti, L. G., Ed.; CRCP: New York, 1979; Vol. 1, pp 251-274.
14. Patel, S.; Gibson, R. In vivo site-directed radiotracers: a mini-review Nucl. Med. Biol. 2008, 35, 805-815
15. Sanabria, S.; Fan, H.; O'Malley, S.; Miller, P.; Zeng, Z.; Ryan, C.; Riffel, K.; Williams, M.; Eng, W.; Gallicchio, S. N.; Bell, I. M.; Selnick, H.; Salvatore, C.; Hargreaves, R.; Kane, S.; Graham, S.; Sur, C.; Cook, J. J.; Hostetler, E. [C-11]MK-4232: The First PET Tracer for the Calcitonin Gene-Related Peptide (CGRP) Receptor and its Evaluation in Rhesus Monkey, Sixth Annual World Molecular Imaging Congress, Montreal, Canada, September 23-26, 2009; poster presentation number 0813.
16. Lin, J. H. CSF as a surrogate for assessing CNS exposure: an industrial perspective Curr. Drug Metab. 2008, 9, 46-59
17. Bell, I. M.; Stump, C. A.; Gallicchio, S. N.; Staas, D. D.; Zartman, C. B.; Moore, E. L.; Sain, N.; Urban, M.; Bruno, J. G.; Calamari, A.; Kemmerer, A. L.; Mosser, S. D.; Fandozzi, C.; White, R. B.; Zrada, M. M.; Selnick, H. G.; Graham, S. L.; Vacca, J. P.; Kane, S. A.; Salvatore, C. A. MK-8825: a potent and selective CGRP receptor antagonist with good oral activity in rats Bioorg. Med. Chem. Lett. 2012, 22, 3941-3945
18. Selnick, H. G.; Bell, I. M.; McWherter, M.; Staas, D. D.; Stachel, S. J.; Steele, T.; Stump, C. A.; Wood, M. R.; Zartman, C. B. WO 2009/120652.
19. Wood, M. R.; Gallicchio, S. N.; Selnick, H. G.; Zartman, C. B.; Bell, I. M.; Stump, C. A. U.S. Patent 7,629,338, 2009.
20. Stump, C. A.; Bell, I. M.; Bednar, R. A.; Bruno, J. G.; Fay, J. F.; Gallicchio, S. N.; Johnston, V. K.; Moore, E. L.; Mosser, S. D.; Quigley, A. G.; Salvatore, C. A.; Theberge, C. R.; Zartman, C. B.; Zhang, X.-F.; Kane, S. A.; Graham, S. L.; Vacca, J. P.; Williams, T. M. The discovery of highly potent CGRP receptor antagonists Bioorg. Med. Chem. Lett. 2009, 19, 214-217