Translocator protein (TSPO) ligands for the diagnosis or treatment of neurodegenerative diseases: a patent review (2010 – 2015; part 2)

References

• Romeo E, Cavallaro S, Korneyev A, et al. Stimulation of brain steroidogenesis by 2-aryl-indole-3-acetamide derivatives acting at the mitochondrial diazepam-binding inhibitor receptor complex. J Pharmacol Exp Ther. 1993 Oct;267(1):462–471.
   PubMed Web of Science ®Google Scholar
• Wadsworth H, Jones PA, Chau WF, et al. [F-18]GE-180: A novel fluorine-18 labelled PET tracer for imaging Translocator protein 18 kDa (TSPO). Bioorg Med Chem Lett. 2012 Feb 1;22(3):1308–1313.
   PubMed Web of Science ®Google Scholar
• Li H, Papadopoulos V. Peripheral-type benzodiazepine receptor function in cholesterol transport. Identification of a putative cholesterol recognition/interaction amino acid sequence and consensus pattern. Endocrinology. 1998 Dec;139(12):4991–4997.
   PubMed Web of Science ®Google Scholar
• Bordet T, Buisson B, Michaud M, et al. Identification and characterization of cholest-4-en-3-one, oxime (TRO19622), a novel drug candidate for amyotrophic lateral sclerosis. J Pharmacol Exp Ther. 2007 Aug;322(2):709–720.
   PubMed Web of Science ®Google Scholar
• Owen DR, Gunn RN, Rabiner EA, et al. Mixed-affinity binding in humans with 18-kDa translocator protein ligands. J Nucl Med. 2011 Jan;52(1):24–32.
   PubMed Web of Science ®Google Scholar
• Trigg WJ, Jones PA. S-enantiomer of tetracyclic indole derivative as pbr ligands. WO2015040151 A1. 2015.
   Google Scholar
• Kozikowski AP, Ma D, Brewer J, et al. Chemistry, binding affinities, and behavioral properties of a new class of antineophobic mitochondrial Dbi receptor complex (Mdrc) ligands. J Med Chem. 1993 Oct 1;36(20):2908–2920.
   PubMed Web of Science ®Google Scholar
• Liao Y, Kozikowski AP, Guidotti A, et al. Synthesis and pharmacological evaluation of benzofuran-acetamides as “antineophobic” mitochondrial DBI receptor complex ligands. Bioorg Med Chem Lett. 1998 Aug 18;8(16):2099–2102.
   PubMed Web of Science ®Google Scholar
• Da Settimo F, Simorini F, Taliani S, et al. Anxiolytic-like effects of N,N-dialkyl-2-phenylindol-3-ylglyoxylamides by modulation of translocator protein promoting neurosteroid biosynthesis. J Med Chem. 2008 Sep 25;51(18):5798–5806.
   PubMed Web of Science ®Google Scholar
• Primofiore G, Da Settimo F, Taliani S, et al. N,N-dialkyl-2-phenylindol-3-ylglyoxylamides. A new class of potent and selective ligands at the peripheral benzodiazepine receptor. J Med Chem. 2004 Mar 25;47(7):1852–1855.
   PubMed Web of Science ®Google Scholar
• Barresi E, Bruno A, Taliani S, et al. Deepening the topology of the translocator protein binding site by novel N,N-Dialkyl-2-arylindol-3-ylglyoxylamides. J Med Chem. 2015 Aug 13;58(15):6081–6092.
   PubMed Web of Science ®Google Scholar
• Okubo T, Yoshikawa R, Chaki S, et al. Design, synthesis, and structure-activity relationships of novel tetracyclic compounds as peripheral benzodiazepine receptor ligands. Bioorg Med Chem. 2004 Jul 1;12(13):3569–3580.
   PubMed Web of Science ®Google Scholar
• Arstad E, Wilson I, Luthra SK, et al. Tetracyclic indole derivatives as in vivo imaging agents and having peripheralbenzodiazepine receptor affinity (pbr). WO 2007057705A1. 2007.
   Google Scholar
• Wadsworth HJ, Shan B, O’shea D, et al. Imaging neuroinflammation. WO2010037851 A2. 2010.
   Google Scholar
• O’Shea D, Ahmad R, Arstad E, et al. Exploration of the structure-activity relationship of a novel tetracyclic class of TSPO ligands-potential novel positron emitting tomography imaging agents. Bioorg Med Chem Lett. 2013 Apr 15;23(8):2368–2372.
   PubMed Web of Science ®Google Scholar
• Jones PA. In vivo imaging method of mood disorders. US20130177501 A1. 2013.
   Google Scholar
• Wadsworth HJ, O’shea D, Passmore J, et al. Indole derivatives. WO2010109007 A2. 2010.
   Google Scholar
• Morrison MS, Morisson-Iveson V, Trigg WJ. Macrophage imaging. WO2015040087 A1. 2015.
   Google Scholar
• Jones PA. In vivo imaging method for cancer. WO2012041953 A1. 2012.
   Google Scholar
• Achanath R, Balaji S, Fairway SM, et al. Tricyclic indole derivatives as pbr ligands. EP255289 A1. 2013.
   Google Scholar
• Trigg WJ, Jones PA. Carbazole compounds for in vivo imaging. WO2015040148 A1. 2015.
   Google Scholar
• Leducq N, Bono F, Sulpice T, et al. Role of peripheral benzodiazepine receptors in mitochondrial, cellular, and cardiac damage induced by oxidative stress and ischemia-reperfusion. J Pharmacol Exp Ther. 2003 Sep;306(3):828–837.
   PubMed Web of Science ®Google Scholar
• Vin V, Leducq N, Bono F, et al. Binding characteristics of SSR180575, a potent and selective peripheral benzodiazepine ligand. Biochem Biophys Res Commun. 2003 Oct 24;310(3):785–790.
   PubMed Web of Science ®Google Scholar
• Bribes E, Bourrie B, Casellas P. Ligands of the peripheral benzodiazepine receptor have therapeutic effects in pneumopathies in vivo. Immunol Lett. 2003 Sep 8;88(3):241–247.
   PubMed Web of Science ®Google Scholar
• Benavides J, Evanno Y, Ferzaz B, et al. Use of pyridazino[4,5-b]indole-1-acetamide deravatives for preparing medicines for treating diseases related to the dysfunction of peripheral benzodiazepine receptors. WO2000044384 A1. 2000.
   Google Scholar
• Chauveau F, Boutin H, Van Camp N, et al. In vivo imaging of neuroinflammation in the rodent brain with [C-11]SSR180575, a novel indoleacetamide radioligand of the translocator protein (18 kDa). Eur J Nucl Med Mol Imaging. 2011 Mar;38(3):509–514.
   PubMed Web of Science ®Google Scholar
• Benavides J, Boutin H, Castel MN, et al. Use of 7-chloro-n,n,5-trimethyl-4-oxo-3-phenyl-3,5-dihydro-4h-pyridazino[4,5-b] indole-1-acetamide as a biomarker of peripheral benzodiazepine receptor levels. US20120039816 A1. 2012.
   Google Scholar
• Cheung YY, Nickels ML, Tang D, et al. Facile synthesis of SSR180575 and discovery of 7-chloro-N,N,5-trimethyl-4-oxo-3(6-[(18)F]fluoropyridin-2-yl)-3,5-dihydro-4H-pyri dazino[4,5-b]indole-1-acetamide, a potent pyridazinoindole ligand for PET imaging of TSPO in cancer. Bioorg Med Chem Lett. 2014 Sep 15;24(18):4466–4471.
   PubMed Web of Science ®Google Scholar
• Damont A, Marguet F, Puech F, et al. Synthesis and in vitro characterization of novel fluorinated derivatives of the TSPO 18 kDa ligand SSR180575. Eur J Med Chem. 2015 Aug 28;101:736–745.
   PubMed Web of Science ®Google Scholar
• Do Rego JL, Vaudry D, Vaudry H. The non-benzodiazepine anxiolytic drug etifoxine causes a rapid, receptor- independent stimulation of neurosteroid biosynthesis. Plos One. 2015;10(3):e0120473/1–e73/20.
   PubMed Web of Science ®Google Scholar
• Wolf L, Bauer A, Melchner D, et al. Enhancing neurosteroid synthesis - relationship to the pharmacology of translocator protein (18 kDa) (TSPO) ligands and benzodiazepines. Pharmacopsychiatry. 2015;48(2):72–77.
   PubMed Web of Science ®Google Scholar
• Nothdurfter C, Rammes G, Baghai TC, et al. Translocator protein (18 kDa) as a target for novel anxiolytics with a favourable side-effect profile. J Neuroendocrinol. 2012;24(1):82–92.
   PubMed Web of Science ®Google Scholar
• Aouad M, Petit-Demouliere N, Goumon Y, et al. Etifoxine stimulates allopregnanolone synthesis in the spinal cord to produce analgesia in experimental mononeuropathy. Eur J Pain. 2014;18(2):258–268.
   PubMed Web of Science ®Google Scholar
• Nguyen N, Fakra E, Pradel V, et al. Efficacy of etifoxine compared to lorazepam monotherapy in the treatment of patients with adjustment disorders with anxiety: a double-blind controlled study in general practice. Hum Psychopharmacol. 2006;21(3):139–149.
   PubMed Web of Science ®Google Scholar
• Rajan ST, Rao GVP, inventors; Msn Laboratories Limited, India. assignee. Process for the preparation of etifoxine hydrochloride. patent IN2012CH03232 A. 2014.
   Google Scholar
• Putman D, Hogenkamp D, Dasse O, et al. Enantiomerically pure S-etifoxine, pharmaceutical compositions thereof and methods of their use. US8110569 B2. 2012.
   Google Scholar
• Verleye M, Guern MEL, Girard P, et al. Neuroprotective compounds and pharmaceutical compositions comprising them. US8338410 B2. 2012.
   Google Scholar
• Verleye M, Girard P, Le GME. Treatment of degenerations and light-induced damage to the retina. WO2015113991 A1. 2015.
   Google Scholar
• Jeon KI, Xu X, Aizawa T, et al. Vinpocetine inhibits NF-kappaB-dependent inflammation via an IKK-dependent but PDE-independent mechanism. Proc Natl Acad Sci U S A. 2010 May 25;107(21):9795–9800.
   PubMed Web of Science ®Google Scholar
• Zhao YY, Yu JZ, Li QY, et al. TSPO-specific ligand vinpocetine exerts a neuroprotective effect by suppressing microglial inflammation. Neuron Glia Biol. 2011 May;7(2–4):187–197.
   PubMedGoogle Scholar
• Wang H, Zhang K, Zhao L, et al. Anti-inflammatory effects of vinpocetine on the functional expression of nuclear factor-kappa B and tumor necrosis factor-alpha in a rat model of cerebral ischemia-reperfusion injury. Neurosci Lett. 2014 Apr 30;566:247–251.
   PubMed Web of Science ®Google Scholar
• Owen D, Wilkins M. Methods to predict binding affinity of tspo imaging agents to tspo. US20140301947 A1. 2014.
   Google Scholar
• Gulyas B, Vas A, Toth M, et al. Age and disease related changes in the translocator protein (TSPO) system in the human brain: positron emission tomography measurements with [11C]vinpocetine. NeuroImage. 2011 Jun 1;56(3):1111–1121.
   PubMed Web of Science ®Google Scholar
• Gulyas B, Toth M, Vas A, et al. Visualising neuroinflammation in post-stroke patients: a comparative PET study with the TSPO molecular imaging biomarkers [11C]PK11195 and [11C]vinpocetine. Curr Radiopharm. 2012 Jan;5(1):19–28.
   PubMedGoogle Scholar
• Nyakas C, Felszeghy K, Szabo R, et al. Neuroprotective effects of vinpocetine and its major metabolite cis-apovincaminic acid on NMDA-induced neurotoxicity in a rat entorhinal cortex lesion model. CNS Neurosci Ther. 2009 Summer;15(2):89–99.
   PubMed Web of Science ®Google Scholar
• Dolle F, Luus C, Reynolds A, et al. Radiolabelled molecules for imaging the translocator protein (18 kDa) using positron emission tomography. Curr Med Chem. 2009;16(22):2899–2923.
   PubMed Web of Science ®Google Scholar
• Éles J, Borza I, Tihanyi K, et al. A new diaza-benzofluoranthene derivative as drug. WO2013076646 A1. 2013.
   Google Scholar
• Katsumata S, Mitsui K, inventors; Ono Pharmaceutical Co., Ltd., Japan. assignee. Drug and method for preventing/treating stress-induced diseases. patent WO2015190568 A1. 2015.
   Google Scholar
• Ohmoto K, Kato M, Kagamiishi Y, et al. Tricyclic compound and use thereof. WO2006068164 A1. 2006.
   Google Scholar
• Martin LJ. Olesoxime, a cholesterol-like neuroprotectant for the potential treatment of amyotrophic lateral sclerosis. IDrugs. 2010 Aug;13(8):568–580.
   PubMed Web of Science ®Google Scholar
• Sunyach C, Michaud M, Arnoux T, et al. Olesoxime delays muscle denervation, astrogliosis, microglial activation and motoneuron death in an ALS mouse model. Neuropharmacology. 2012 Jun;62(7):2346–2352.
   PubMed Web of Science ®Google Scholar
• Magalon K, Zimmer C, Cayre M, et al. Olesoxime accelerates myelination and promotes repair in models of demyelination. Ann Neurol. 2012 Feb;71(2):213–226.
   PubMed Web of Science ®Google Scholar
• Zanetta C, Nizzardo M, Simone C, et al. Molecular therapeutic strategies for spinal muscular atrophies: current and future clinical trials. Clin Ther. 2014 Jan 1;36(1):128–140.
   PubMed Web of Science ®Google Scholar
• Schaller S, Paradis S, Ngoh GA, et al. TRO40303, a new cardioprotective compound, inhibits mitochondrial permeability transition. J Pharmacol Exp Ther. 2010 Jun;333(3):696–706.
   PubMed Web of Science ®Google Scholar
• Pruss R, Drouot C. Use of at least one oxime derivative of 3,5-seco-4-nor-cholestane as antioxidants. US8338488 B2. 2012.
   Google Scholar
• Le Lamer S, Paradis S, Rahmouni H, et al. Translation of TRO40303 from myocardial infarction models to demonstration of safety and tolerance in a randomized Phase I trial. J Transl Med. 2014;12:38.
   PubMed Web of Science ®Google Scholar
• Atar D, Arheden H, Berdeaux A, et al. Effect of intravenous TRO40303 as an adjunct to primary percutaneous coronary intervention for acute ST-elevation myocardial infarction: MITOCARE study results. Eur Heart J. 2015 Jan 7;36(2):112–119.
   PubMed Web of Science ®Google Scholar
• Ms G. Rationale and design of the ‘MITOCARE’ study: a phase II, multicenter, randomized, double-blind, placebo-controlled study to assess the safety and efficacy of TRO40303 for the reduction of reperfusion injury in patients undergoing percutaneous coronary intervention for acute myocardial infarction. Cardiology. 2012;123(4):201–207.
   PubMed Web of Science ®Google Scholar
• Schaller S, Michaud M, Latyszenok V, et al. TRO40303, a mitochondrial-targeted cytoprotective compound, provides protection in hepatitis models. Pharmacol Res Perspect. 2015 Jun;3(3):e00144.
   Google Scholar
• Ayuso MI, Chioua M, Martinez-Alonso E, et al. CholesteroNitrones for stroke. J Med Chem. 2015 Aug 27;58(16):6704–6709.
   PubMed Web of Science ®Google Scholar
• Midzak A, Akula N, Lecanu L, et al. Novel androstenetriol interacts with the mitochondrial translocator protein and controls steroidogenesis. J Biol Chem. 2011 Mar 18;286(11):9875–9887.
   PubMed Web of Science ®Google Scholar
• Midzak A, Rammouz G, Papadopoulos V. Structure-activity relationship (SAR) analysis of a family of steroids acutely controlling steroidogenesis. Steroids. 2012 Nov;77(13):1327–1334.
   PubMed Web of Science ®Google Scholar
• Akula N, Greeson J, Lecanu L, et al. Structure based drug design of steroidogenesis inhibitors. WO2007103162 A2. 2007.
   Google Scholar
• Midzak AS, Akula N, Rone MB, et al. Computational modeling and biological validation of novel non-steroidal ligands for the cholesterol recognition/interaction amino acid consensus (CRAC) motif of the mitochondrial translocator protein (TSPO). Pharmacol Res. 2015 Sep;99:393–403.
   PubMed Web of Science ®Google Scholar
• Lecanu L, Yao ZX, McCourty A, et al. Control of hypercholesterolemia and atherosclerosis using the cholesterol recognition/interaction amino acid sequence of the translocator protein TSPO. Steroids. 2013 Feb;78(2):137–146.
   PubMed Web of Science ®Google Scholar
• Snyder SH, Verma A, Trifiletti RR. The peripheral-type benzodiazepine receptor: a protein of mitochondrial outer membranes utilizing porphyrins as endogenous ligands. FASEB J. 1987 Oct;1(4):282–288.
   PubMed Web of Science ®Google Scholar
• Verma A, Nye JS, Snyder SH. Porphyrins are endogenous ligands for the mitochondrial (peripheral-type) benzodiazepine receptor. Proc Natl Acad Sci U S A. 1987 Apr;84(8):2256–2260.
   PubMed Web of Science ®Google Scholar
• Guo YZ, Kalathur RC, Liu Q, et al. Structure and activity of tryptophan-rich TSPO proteins. Science. 2015 Jan 30;347(6221):551–555.
   PubMed Web of Science ®Google Scholar
• Ricchelli F, Sileikyte J, Bernardi P. Shedding light on the mitochondrial permeability transition. Biochim Biophys Acta. 2011 May;1807(5):482–490.
   PubMed Web of Science ®Google Scholar