Calcitonin gene-related peptide receptor antagonists for the treatment of migraine: a patent review

Bibliography

• Goadsby PJ, Lipton RB, Ferrari MD. Migraine – current understanding and treatment. N Engl J Med 2002;346:257-70
   PubMed Web of Science ®Google Scholar
• Durham PL. CGRP-receptor antagonists – a fresh approach to migraine therapy? N Engl J Med 2004;350:1073-5
   PubMed Web of Science ®Google Scholar
• Silberstein SD. Migraine. Lancet 2004;363:381-91
   PubMed Web of Science ®Google Scholar
• Poyner DR. Calcitonin gene-related peptide: multiple actions, multiple receptors. Pharmacol Ther 1992;56:23-51
   PubMed Web of Science ®Google Scholar
• Lassen LH, Haderslev PA, Jacobsen VB, CGRP may play a causative role in migraine. Cephalalgia 2002;22:54-61
   PubMed Web of Science ®Google Scholar
• Olesen J, Diener H.-C, Husstedt IW, . Calcitonin gene-related peptide receptor antagonist BIBN 4096 BS for the acute treatment of migraine. N Engl J Med 2004;350:1104-10
   PubMed Web of Science ®Google Scholar
• Paone DV, Shaw AW, Nguyen DN, 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). J Med Chem 2007;50:5564-7
   PubMed Web of Science ®Google Scholar
• Edvinsson L. New therapeutic target in primary headaches – blocking the CGRP receptor. Expert Opin Ther Targets 2003;7:377-83 and references cited therein
   PubMed Web of Science ®Google Scholar
• Goadsby PJ, Edvinsson L, Ekman R. Vasoactive peptide release in the extracerebral circulation of humans during migraine attack. Ann Neurol 1990;28:183-7
   PubMed Web of Science ®Google Scholar
• Edvinsson L. CGRP blockers in migraine therapy: where do they act? Br J Pharmacol 2008;155:967-9
   PubMed Web of Science ®Google Scholar
• Tepper SJ, Stillman MJ. Clinical and preclinical rationale for CGRP-receptor antagonists in the treatment of migraine. Headache 2008;48:1259-68
   PubMed Web of Science ®Google Scholar
• Conner AC, Hay DL, Howitt SG, Interaction of calcitonin-gene-related peptide with its receptors. Biochem Soc Trans 2002;30:451-5
   PubMed Web of Science ®Google Scholar
• Poyner DR, Sexton PM, Marshall I, International Union of Pharmacology. XXXII. The mammalian calcitonin gene-related peptides, adrenomedullin, amylin, and calcitonin receptors. Pharmacol Rev 2002;54:233-46
   PubMed Web of Science ®Google Scholar
• Boehringer Ingelheim. Modified aminoacids, pharmaceuticals containing these compounds and method for their production. WO 98/11128; 1998.
   Google Scholar
• Rudolf K, Eberlein W, Engel W, Development of human calcitonin gene-Related Peptide (CGRP) receptor antagonists. 1. Potent and selective small molecule CGRP antagonists. 1-[N2-[3,5-Dibromo-N-[[4-(3,4-dihydro-2(1H)-oxoquinazolin-3-yl)-1-piperidinyl]carbonyl]-D-tyrosyl]-L-lysyl]-4-(4-pyridinyl)piperazine: the first CGRP antagonist for clinical trials in acute migraine. J Med Chem 2005;48:5921-31
   PubMed Web of Science ®Google Scholar
• Doods H, Hallermayer G, Wu Dm, Pharmacological profile of BIBN4096BS, the first selective small molecule CGRP antagonist. Br J Pharmacol 2000;129:420-3
   PubMed Web of Science ®Google Scholar
• Mallee JJ, Salvatore CA, LeBourdelles B, Receptor activity-modifying protein 1 determines the species selectivity of non-peptide CGRP receptor antagonists. J Biol Chem 2002;277:14294-8
   PubMed Web of Science ®Google Scholar
• Escott KJ, Beattie DT, Connor HE, Trigeminal ganglion stimulation increases facial skin blood flow in the rat: a major role for calcitonin gene-related peptide. Brain Res 1995;669:93-9
   PubMed Web of Science ®Google Scholar
• Iovino M, Feifel U, Yong C-L, Safety, tolerability and pharmacokinetics of BIBN 4096 BS, the first selective small molecule calcitonin gene-related peptide receptor antagonist, following single intravenous administration in healthy volunteers. Cephalalgia 2004;24:645-56
   PubMed Web of Science ®Google Scholar
• Boehringer Ingelheim. Selected CGRP antagonists, method for production and use thereof as medicament. WO2007028812; 2007.
   Google Scholar
• Boehringer Ingelheim. Antagonists of calcitonin gene-related peptide. US 6313097; 2001.
   Google Scholar
• Boehringer Ingelheim. Selected CGRP antagonists, processes for preparing them and their use as pharmaceutical compositions. US 2006/0079504; 2006.
   Google Scholar
• Boehringer Ingelheim. CGRP antagonists. US 2007/0244099; 2007, continuation of US 2004/0132716; 2004 (abandoned)
   Google Scholar
• Boehringer Ingelheim. Selected CGRP-antagonists, process for preparing them and their use as pharmaceutical compositions. US7479488; 2009.
   Google Scholar
• Boehringer Ingelheim. Selected CGRP-antagonists process for preparing them and their use as pharmaceutical compositions. US7205294; 2007.
   Google Scholar
• Boehringer Ingelheim. Selected CGRP antagonists method for production and use thereof as medicament. WO 2007/045672; 2007.
   Google Scholar
• Boehringer Ingelheim. Selected CGRP-antagonists, processes for preparing them and their use as pharmaceutical compositions. US 2008/0280887; 2008.
   Google Scholar
• Boehringer Ingelheim. Selected CGRP-antagonists, processes for preparing them and their use as pharmaceutical compositions. US 2007/0049581; 2007.
   Google Scholar
• Boehringer Ingelheim. CGRP-antagonists, process for preparing them and their use as pharmaceutical compositions. US7528129; 2009.
   Google Scholar
• Boehringer Ingelheim. DE102006039038; 2008
   Google Scholar
• Boehringer Ingelheim. Selected CGRP-antagonists, process for preparing them and their use as pharmaceutical compositions. US7491717; 2009.
   Google Scholar
• Boehringer Ingelheim. Selected CGRP-antagonists, process for preparing them and their use as pharmaceutical compositions. US7439237; 2008.
   Google Scholar
• Boehringer Ingelheim. X = O: selected CGRP-antagonists, process for preparing them and their use as pharmaceutical compositions. US7279471; 2007; X = NH: selected CGRP-antagonists, process for preparing them and their use as pharmaceutical compositions. US7547694; 2009.
   Google Scholar
• Boehringer Ingelheim. Selected CGRP-antagonists, processes for preparing them and their use as pharmaceutical compositions. US2007/0072847; 2007.
   Google Scholar
• Boehringer Ingelheim. Selected CGRP-antagonists, process for preparing them and their use as pharmaceutical compositions. US2005/0250763; 2005.
   Google Scholar
• Boehringer Ingelheim. Production method. US2008/045705; 2008.
   Google Scholar
• Boehringer Ingelheim. Novel preparation process. WO2009/021942; 2009.
   Google Scholar
• Boehringer Ingelheim. Novel compounds. WO2009/043797; 2009.
   Google Scholar
• Boehringer Ingelheim Pharmaceuticals. BI 44370 TA in acute migraine attack. ClinicalTrials.gov identifier NCT00751803
   Google Scholar
• Boehringer Ingelheim. (a) Substituted piperidines, pharmaceutical compositions containing these compounds, their use and processes for the preparation thereof. US7026312; 2006. (b) Substituted piperidines, pharmaceutical compositions containing these compounds, their use and processes for the preparation thereof. US7538115; 2009.
   Google Scholar
• Boehringer Ingelheim. Substituted piperidines, pharmaceutical compositions containing these compounds, their use and processes for the preparation thereof. US6949541; 2005.
   Google Scholar
• Boehringer Ingelheim. Arylalkane, arylalkene and aryl azaalkane, medicaments containing said compounds and method for the production thereof. US7230001; 2007.
   Google Scholar
• Boehringer Ingelheim. Cyclopropane CGRP antagonists, medicaments containing these compounds, and method for the production thereof. US7407963; 2008.
   Google Scholar
• Boehringer Ingelheim. Novel compounds. WO2009/034028; 2009.
   Google Scholar
• Boehringer Ingelheim. Novel compounds. WO2009/034029; 2009.
   Google Scholar
• Boehringer Ingelheim. CGRP antagonists. WO2009/050232; 2009.
   Google Scholar
• Boehringer Ingelheim. CGRP antagonists. WO2009/050234; 2009.
   Google Scholar
• Boehringer Ingelheim. CGRP antagonists. WO2009/050235; 2009.
   Google Scholar
• Boehringer Ingelheim. CGRP antagonists. WO2009/050237; 2009.
   Google Scholar
• Boehringer Ingelheim. Novel compounds. WO2009/065919; 2009.
   Google Scholar
• Boehringer Ingelheim. Novel compounds. WO2009/065920; 2009.
   Google Scholar
• Boehringer Ingelheim. Novel compounds. WO2009/065922; 2009.
   Google Scholar
• Boehringer Ingelheim. Novel compounds. WO2009/065921; 2009.
   Google Scholar
• Williams TM, Stump CA, Nguyen DN, Non-peptide calcitonin gene-related peptide receptor antagonists from a benzodiazepine lead. Bioorg Med Chem Lett 2006;16:2595-8
   PubMed Web of Science ®Google Scholar
• Merck and Co., IncBenzodiazepine CGRP receptor antagonists. US7196079; 2007
   Google Scholar
• Merck and Co., Inc. CGRP receptor antagonists. WO2006/078554; 2006
   Google Scholar
• Merck and Co., IncBenzodiazepine CGRP receptor antagonists. US7476665; 2009
   Google Scholar
• Burgey CS, Stump CA, Nguyen DN, Benzodiazepine calcitonin gene-related peptide (CGRP) receptor antagonists: optimization of the 4-substituted piperidine. Bioorg Med Chem Lett 2006;16:5052-6
   PubMed Web of Science ®Google Scholar
• Merck and Co., Inc. Heterocyclic benzodiazepine CGRP receptor antagonists. WO2007/016087; 2007
   Google Scholar
• Shaw AS, Paone DV, Nguyen DN, Caprolactams as potent CGRP receptor antagonists for the treatment of migraine. Bioorg Med Chem Lett 2007;17:4795-8
   PubMed Web of Science ®Google Scholar
• Merck and Co., IncCGRP receptor antagonists. US7205292; 2007
   Google Scholar
• Merck and Co., Inc. CGRP receptor antagonists. US7491,713; 2009
   Google Scholar
• Merck and Co., Inc. CGRP receptor antagonists. US6953790; 2005. See also continuation patents (a) US7235545; 2007 (b) US7452903; 2008, and (c) US7534784; 2009
   Google Scholar
• Salvatore CA, Hershey JC, Corcoran HA, Pharmacological characterization of MK-0974 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], a potent and orally active calcitonin gene-related peptide receptor antagonist for the treatment of migraine. J Pharmacol Exp Ther 2008;324:416-21
   PubMed Web of Science ®Google Scholar
• Hershey JC, Corcoran HA, Baskin EP, Investigation of the species selectivity of a nonpeptide CGRP receptor antagonist using a novel pharmacodynamic assay. Regul Pept 2005;127:71-7
   PubMedGoogle Scholar
• Merck and Co., Inc. CGRP receptor antagonists. WO2006/041830; 2006
   Google Scholar
• Merck and Co., Inc. Benzazepine compounds as CGRP receptor antagonists. WO2008/085317; 2008
   Google Scholar
• Merck and Co., Inc. CGRP receptor antagonists. WO2006/044449; 2006
   Google Scholar
• Merck and Co., Inc. CGRP receptor antagonists. WO2006/047196; 2006
   Google Scholar
• Merck and Co., Inc. CGRP receptor antagonists. WO2006/044504; 2006
   Google Scholar
• Paone D. V.. Calcitonin gene-related peptide (CGRP) receptor antagonists for the treatment of migraine: development of orally bioavailable imidazoazepanes. Presented at the 235th American Chemical Society National Meeting, New Orleans, LA; April 2008;6:
   Google Scholar
• Merck and Co., Inc. CGRP receptor antagonists. WO2006/099268; 2006
   Google Scholar
• Nguyen DN, Paone DV, Shaw AS, Calcitonin gene-related peptide (CGRP) receptor antagonists: investigations of a pyridinone template. Bioorg Med Chem Lett 2008;18:755-8
   PubMed Web of Science ®Google Scholar
• Merck and Co., IncCarboxamide spirohydantoin CGRP receptor antagonists. US7288559; 2007
   Google Scholar
• Merck and Co., IncBenzodiazepine spirohydantoin CGRP receptor antagonists. US7205293; 2007
   Google Scholar
• Merck and Co., IncAryl spirohydantoin CGRP receptor antagonists. US7189722; 2007
   Google Scholar
• Merck and Co., IncMonocyclic anilide spirohydantoin CGRP receptor antagonists. US7192954; 2007
   Google Scholar
• Merck and Co., Inc. Monocyclic anilide spirolactam CGRP receptor antagonists. WO2008/112159; 2008
   Google Scholar
• Merck and Co., Inc. CGRP receptor antagonists with tertiary amide, sulfonamide, carbamate, and urea end groups. WO2008/127584; 2008
   Google Scholar
• Merck and Co., IncBicyclic anilide spirohydantoin CGRP receptor antagonists. US7202251; 2007
   Google Scholar
• Bell IM, Bednar RA, Fay JF, Identification of novel, orally bioavailable spirohydantoin CGRP receptor antagonists. Bioorg Med Chem Lett 2006;16:6165-9
   PubMed Web of Science ®Google Scholar
• Merck and Co., Inc. Tricyclic anilide spirohydantoin CGRP receptor antagonists. WO2006/031676; 2006
   Google Scholar
• Theberge CR, Bednar RA, Bell IM, Potent benzimidazolone-based CGRP receptor antagonists. Bioorg Med Chem Lett 2008;18:6122-5
   PubMed Web of Science ®Google Scholar
• Stump CA, Bell IM, Bednar RA, The discovery of highly potent CGRP receptor antagonists. Bioorg Med Chem Lett 2009:19:214-7
   PubMed Web of Science ®Google Scholar
• Merck and Co., Inc. Bicyclic anilide spirolactam CGRP receptor antagonists. WO2006/031610; 2006
   Google Scholar
• Merck and Co., Inc. Tricyclic anilide spirolactam CGRP receptor antagonists. WO2006/031491; 2006
   Google Scholar
• Bell IM, Bednar RA, Corcoran HA, The identification of potent, orally bioavailable tricyclic CGRP receptor antagonists. Bioorg Med Chem Lett 2009;19:4740-2
   PubMed Web of Science ®Google Scholar
• Merck and Co., Inc. Bicyclic anilide heterocyclic CGRP receptor antagonists. WO2008/130512; 2008
   Google Scholar
• Merck and Co., Inc. Tricyclic anilide heterocyclic CGRP receptor antagonists. WO2008/153852; 2008
   Google Scholar
• Merck and Co., Inc. Aryl spirolactam CGRP receptor antagonists. WO2006/031513; 2006
   Google Scholar
• Merck and Co., Inc. Aryl heterocyclic CGRP receptor antagonists. WO2008/130524; 2008
   Google Scholar
• Merck and Co., Inc. Monocyclic anilide spirolactam CGRP receptor antagonists. WO2006/029153; 2006
   Google Scholar
• Merck and Co., Inc. Constrained spirocyclic compounds as CGRP receptor antagonists. WO2008/073251; 2008
   Google Scholar
• Merck and Co., Inc. Substituted spirocyclic CGRP receptor antagonists. WO2008/020902; 2008
   Google Scholar
• Bell IM. Discovery of a novel, orally bioavailable CGRP receptor antagonist for the treatment of migraine. Presented at the 237th American Chemical Society National Meeting, Salt Lake City, UT; March 2009;22:
   Google Scholar
• Merck and Co., IncCarboxamide spirolactam CGRP receptor antagonists. US7390798; 2008
   Google Scholar
• Merck and Co., Inc. Carboxamide heterocyclic CGRP receptor antagonists. WO2008/153849; 2008
   Google Scholar
• Merck and Co., Inc. Bicyclic spirohydantoin CGRP receptor antagonists. WO2007/061695; 2007
   Google Scholar
• Merck and Co., Inc. Spirohydantoin tricyclic CGRP receptor antagonists. WO2007/061694; 2007
   Google Scholar
• Merck and Co., Inc. Spirolactam aryl CGRP receptor antagonists. WO2007/061677; 2007
   Google Scholar
• Merck and Co., Inc. Spirolactam tricyclic CGRP receptor antagonists. WO2007/061692; 2007
   Google Scholar
• Merck and Co., Inc. Spirohydantoin aryl CGRP receptor antagonists. WO2007/061676; 2007
   Google Scholar
• Merck and Co., Inc. Spirolactam bicyclic CGRP receptor antagonists. WO2007/061696; 2007
   Google Scholar
• Merck and Co., Inc. Hydroxypyridine CGRP receptor antagonists. WO2005/009962; 2005
   Google Scholar
• Merck and Co., IncBenzimidazolinyl piperidines as CGRP ligands. US6552043; 2003
   Google Scholar
• Bristol-Myers Squibb. Novel beta-turn mimetics as calcitonin gene related peptide receptor antagonists. US20050209256; 2005.
   Google Scholar
• Bristol-Myers Squibb. Calcitonin gene related peptide receptor antagonists. WO03/104326; 2003.
   Google Scholar
• Bristol-Myers Squibb. Heterocyclic anti-migraine agents. US2005/0153959; 2005.
   Google Scholar
• Bristol-Myers Squibb. CGRP antagonists. US2007/0049577; 2007.
   Google Scholar
• Bristol-Myers Squibb. US2007/0149502; 2007
   Google Scholar
• Bristol-Myers Squibb. US2007/0149503; 2007
   Google Scholar
• Bristol-Myers Squibb. Constrained compounds as CGRP-receptor antagonists. US7380930; 2008.
   Google Scholar
• Bristol-Myers Squibb. Constrained compounds as CGRP-receptor antagonists. US7380931; 2008.
   Google Scholar
• Bristol-Myers Squibb. Constrained compounds as CGRP-receptor antagonists. US7544680; 2009.
   Google Scholar
• Bristol-Myers Squibb. Constrained compounds as CGRP-receptor antagonists. US7470679; 2008.
   Google Scholar
• Bristol-Myers Squibb. Constrained compounds as CGRP-receptor antagonists. US7470680; 2008.
   Google Scholar
• Bristol-Myers Squibb. (a) Anti-migraine treatments. US7314883; 2008.
   Google Scholar
• Degnan AP, Chaturvedula PV, Conway CM, Discovery of (R)-4-(8-Fluoro-2-oxo-1,2-dihydroquinazolin-3-(4H)-yl-N-(3-(7-methyl-1H-indazol-5-yl)-1-oxo-1-(4-(piperidin-1-yl)piperidn-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;51:4858-61
   PubMed Web of Science ®Google Scholar
• Bristol-Myers Squibb. Novel therapeutic agents for the treatment of migraine. US2005/0215576; 2005.
   Google Scholar
• Degnan AP, Conway CM, Dalterio RA, Carbamates as potent calcitonin gene-related peptide antagonists with improved solution stability. Bioorg Med Chem Lett 2009;19:3555-8
   PubMed Web of Science ®Google Scholar
• Bristol-Myers Squibb. Calcitonin gene related peptide receptor antagonists. US7220862; 2007.
   Google Scholar
• Bristol-Myers Squibb. Calcitonin gene related peptide receptor antagonists. WO2005/065779; 2005.
   Google Scholar
• SmithKline Beecham Corporation. Compounds and methods. WO97/09046; 1997.
   Google Scholar
• Daines RA, Sham KKC, Taggart JJ, Quinine analogs as non-peptide calcitonin gene-related peptide (CGRP) receptor antagonists. Bioorg Med Chem Lett 1997;7:2673-6
   Web of Science ®Google Scholar
• SmithKline Beecham Corporation. Compounds and methods. WO98/09630; 1998.
   Google Scholar
• SmithKline Beecham Corporation. 4-Sulfinyl benzamides as calcitonin gene-related peptide receptor antagonists. WO98/56779; 1998.
   Google Scholar
• Aiyar N, Daines RA, Disa J, Pharmacology of SB-273779, a nonpeptide calcitonin gene-related peptide 1 receptor antagonist. J Pharmacol Exp Ther 2001;296:768-75
   PubMed Web of Science ®Google Scholar
• Glaxo Group Limited. 5-Phenyl-1,3,4-oxadiazol-2-yl-acetyl-4-piperidinyl derivatives as CGRP receptor antagonists. WO2009/000819; 2009.
   Google Scholar
• Glaxo Group Limited. Pyrrolo[2,3-d]pyrimidine derivatives as CGRP receptor antagonists. WO2009/060682; 2009.
   Google Scholar
• Vertex Pharmaceuticals Incorporated. CGRP receptor antagonists. WO2008/011190; 2008.
   Google Scholar
• Vertex Pharmaceuticals Incorporated. CGRP receptor antagonists. WO2007/146349; 2007.
   Google Scholar
• Neurogen Corporation. Biaryl ketone-substituted piperidines. WO2008/070014; 2008.
   Google Scholar
• Neurogen Corporation. Amide-substituted aryl piperidines. WO2008/060568; 2008.
   Google Scholar
• Grünenthal GmbH. Substituted cyclopentene compounds. US7109214; 2006.
   Google Scholar
• Ho TW, Mannix LK, Fan X, Randomized controlled trial of an oral CGRP receptor antagonist, MK-0974, in acute treatment of migraine. Neurology 2008;70:1304-12
   PubMed Web of Science ®Google Scholar
• Ho TW, Ferrari MD, Dodick DW, 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;372:2115-23
   PubMed Web of Science ®Google Scholar
• Doggrell SA. Telcagepant is a new oral treatment for migraine. Expert Opin Pharmacother 2009;10:1523-6
   PubMed Web of Science ®Google Scholar
• Boehringer Ingelheim. Use of selected CGRP-antagonists in combination with other antimigraine drugs for the treatment of migraine. US2006/0142273; 2006.
   Google Scholar
• Boehringer Ingelheim. CGRP-antagonist in combination with serotonin-reuptake inhibitor for the treatment of migraine. US2005/0233980; 2005.
   Google Scholar
• Boehringer Ingelheim. DE10314617; 2004
   Google Scholar
• Rita Dobmeyer. Medication for the treatment or prevention of migraine. EP1374870; 2004.
   Google Scholar