Carbon-11 patents (2012–2022): synthetic methodologies and novel radiotracers for PET imaging

References

• Matthews PM, Rabiner EA, Passchier J, et al. Positron emission tomography molecular imaging for drug development: PET for drug development. Br J Clin Pharmacol. 2012;73(2):175–186.
   PubMed Web of Science ®Google Scholar
• Lindner JR, Link J. Molecular imaging in drug discovery and development. Circ Cardiovasc Imaging. 2018:11.
   Web of Science ®Google Scholar
• Donnelly DJ. PET imaging in drug discovery and development. In: Scott P, Kilbourn M, editors. Handbook of radiopharmaceuticals. United Kingdom: Wiley; 2020. p. 703–725.
   Google Scholar
• Anand S, Singh H, Dash A. Clinical applications of PET and PET-CT. Med J Armed Forces India. 2009;65(4):353–358.
   PubMedGoogle Scholar
• Rohren EM, Turkington TG, Coleman RE. Clinical applications of PET in oncology. Radiology. 2004;231(2):305–332.
   PubMed Web of Science ®Google Scholar
• Li Z, Gupte AA, Zhang A, et al. Pet imaging and its application in cardiovascular diseases. Methodist DeBakey Cardiovasc J. 2017;13(1):29.
   PubMedGoogle Scholar
• Tai YF. Applications of Positron Emission Tomography (PET) in neurology. J Neurol Neurosurg Psychiatry. 2004;75:669–676.
   PubMed Web of Science ®Google Scholar
• Innis RB, Cunningham VJ, Delforge J, et al. Consensus nomenclature for in vivo imaging of reversibly binding radioligands. J Cereb Blood Flow Metab. 2007;27(9):1533–1539.
   PubMed Web of Science ®Google Scholar
• Pichler BJ, Wehrl HF, Kolb A, et al. Positron emission tomography/magnetic resonance imaging: the next generation of multimodality imaging? Semin Nucl Med. 2008;38(3):199–208.
   PubMed Web of Science ®Google Scholar
• Goud NS, Kanth Makani VK, Pranay J, et al. Synthesis, 18F-radiolabeling and apoptosis inducing studies of novel 4, 7-disubstituted coumarins. Bioorg Chem. 2020;97:103663.
   PubMed Web of Science ®Google Scholar
• Ghosh KK, Padmanabhan P, Yang CT, et al. Positron emission tomographic imaging in drug discovery. Drug Discov Today. 2021;27(1) :280–291.
   PubMed Web of Science ®Google Scholar
• Shukla A, Kumar U. positron emission tomography: an overview. J Med Phys. 2006;31(1):13.
   PubMedGoogle Scholar
• Hung JC. Bringing new PET drugs to clinical practice - a regulatory perspective. Theranostics. 2013;3(11):885–893.
   PubMed Web of Science ®Google Scholar
• Huang YY. An overview of PET radiopharmaceuticals in clinical use: regulatory, quality and pharmacopeia monographs of the United States and Europe. In: Nuclear Medicine Physics Book. IntechOpen; 2019.
   Google Scholar
• Jackson IM, Lee SJ, Sowa AR, et al. Use of 55 PET radiotracers under approval of a Radioactive Drug Research Committee (RDRC). EJNMMI Radiopharm Chem. 2020;5(1):24.
   PubMedGoogle Scholar
• Thompson S, Kealey S, Sephton SM, et al. Radiochemistry with carbon‐11. In: Handbook radiopharmaceuticals book. Wiley; 2020;143–249.
   Google Scholar
• Yang L, Scott PJH, Shao X. [11C]carbon dioxide: starting point for labeling PET radiopharmaceuticals. In: Carbon dioxide chemistry, capture and oil recovery book. IntechOpen; 2018.
   Google Scholar
• Lu S, Simeon FG, Telu S, et al. The chemistry of labeling heterocycles with carbon-11 or fluorine-18 for biomedical imaging. In: Advances in heterocyclic chemistry. Vol. 132. Elsevier; 2020. p. 241–384.
   Google Scholar
• Szlosek-Pinaud M, Allard M, Fouquet E, et al. State of art in 11C labelled radiotracers synthesis. CMC. 2008;15:235–277.
   PubMed Web of Science ®Google Scholar
• Mille PW, Long NJ, Vilar R, et al. Synthesis of 11 C, 18 F, 15 O, and 13 N radiolabels for positron emission tomography. Angew Chem Int Ed. 2008;47(47):8998–9033.
   PubMed Web of Science ®Google Scholar
• Scott PJH. Methods for the incorporation of carbon-11 to generate radiopharmaceuticals for PET imaging. Angew Chem Int Ed. 2009;48(33):6001–6004.
   PubMed Web of Science ®Google Scholar
• Deng X, Rong J, Wang L, et al. Chemistry for positron emission tomography: recent advances in 11 C-, 18 F-, 13 N-, and 15 O-labeling reactions. Angew Chem Int Ed. 2019;58(9):2580–2605.
   PubMed Web of Science ®Google Scholar
• Rotstein BH, Liang SH, Placzek MS, et al. 11CO bonds made easily for positron emission tomography radiopharmaceuticals. Chem Soc Rev. 2016;45(17):4708–4726.
   PubMed Web of Science ®Google Scholar
• Eriksson J, Antoni G, Långström B, et al. The development of 11C-carbonylation chemistry: a systematic view. Nucl Med Biol. 2021;92:115–137.
   PubMed Web of Science ®Google Scholar
• Dahl K, Halldin C, Schou M. New methodologies for the preparation of carbon-11 labeled radiopharmaceuticals. Clin Transl Imaging. 2017;5(3):275–289.
   PubMed Web of Science ®Google Scholar
• Joshi RK, Goud NS, Nagaraj C, et al. Radiosynthesis challenges of 11C and 18F-labeled radiotracers in the FX2C/N tracerlab and their validation through PET-MR imaging. Appl Radiat Isot. 2021;168:109486.
   PubMed Web of Science ®Google Scholar
• Kealey S, Gee A, Miller PW. Transition metal mediated [11 C]carbonylation reactions: recent advances and applications. J Label Compd Radiopharm. 2014;57(4):195–201.
   PubMed Web of Science ®Google Scholar
• Pretze M, Große-Gehling P, Mamat C. Cross-coupling reactions as valuable tool for the preparation of PET radiotracers. Molecules. 2011;16(2):1129–1165.
   PubMed Web of Science ®Google Scholar
• Goud NS, Bhattacharya A, Joshi RK, et al. Carbon-11: radiochemistry and target-based PET molecular imaging applications in oncology, cardiology, and neurology. J Med Chem. 2021;64(3):1223–1259.
   PubMed Web of Science ®Google Scholar
• Tu Z, Mach RH. C-11 radiochemistry in cancer imaging applications. Ctmc. 2010;10(11):1060–1095.
   Google Scholar
• Brooks AF, Drake LR, Stewart MN, et al. Fluorine-18 patents (2009–2015). Part 1: novel radiotracers. Pharm Pat Anal. 2016;5(1):17–47.
   PubMedGoogle Scholar
• Mossine AV, Thompson S, Brooks AF, et al. Fluorine-18 patents (2009-2015). Part 2: new radiochemistry. Pharm Pat Anal. 2016;5(5):319–349.
   PubMedGoogle Scholar
• Tanzey SS, Thompson S, Scott PJ, et al. Gallium-68: methodology and novel radiotracers for positron emission tomography (2012–2017). Pharm Pat Anal. 2018;7(5):193–227.
   PubMed Web of Science ®Google Scholar
• Doi H, Kida T. Method for [11C]methylation of aromatic compound. WO2017090354A1. 2017.
   Google Scholar
• Bengt L, Oleksiy I. Method for the use of [11C]carbon monoxide in labeling synthesis of 11c-labelled acids by photo-induced free radical carbonylation under mild conditions using sulfoxides. US8232424 B2. 2012.
   Google Scholar
• Turton DR. Preparation of 11C-methyl iodide. US8188324B2. 2012.
   Google Scholar
• Tor K, Bengt L. Miniaturized liquid surface reactions using nanomolar amounts of concentrated [11C]carbondioxide in a stationary gas-phase. US8679452B2. 2014.
   Google Scholar
• Tor K, Tommy F, Bengt L. Method and apparatus for synthesis of [11C] phosgene using concentrated [11C]carbon monoxide with UV light. US8137656B2. 2012.
   Google Scholar
• Tiberiu MS, Peter AZ. Production of carbon-11 using a liquid target. US2016/0035448Al. 2016.
   Google Scholar
• Doi H, Kedashiro M. [2-11C]acetic acid, [2-11C]acetic acid imidyl ester, and methods for the preparation thereof. WO2015156131A1. 2015.
   Google Scholar
• Bengt L, Julien B, Hisashi D, et al. Methods for carbon isotope labeling synthesis by transition metal-promoted carbonylation via isocyanate using azides and carbon-isotope monoxide. US8741261B2. 2014.
   Google Scholar
• Wu X, Zeng H. Method for preparing [11C]-ω-mercaptomethyl fatty acid and its application in preparing myocardial metabolic imaging agent. CN105523977A;. 2016
   Google Scholar
• Audisio D, Cantat T, Destro G. A process for the synthesis of carbon labeled organic compounds. WO2019/193068; 2019.
   Google Scholar
• Hesse R, Fasel A, Bugdaahn N, et al. Use of precursors for the production of carbon-11 labelled amino acids and derivatives thereof. WO2018/206728Al; 2018.
   Google Scholar
• Lee SY, Lee HJ, Lee JH, et al. Rapid synthesis method through solid phase extraction of carbon-11 labeled compounds. IO-2O2O-OO59528; 2020.
   Google Scholar
• Xin JG, Qiyong CL. Preparation of 11C-N-methyl-3-amino-propan-1,2-diol as positron tracer. CN107827754A, 2018.
   Google Scholar
• Tian H. Method and system for preparing 11C-α-methyl-L-tryptophan. CN110790696A; 2020.
   Google Scholar
• Tatebe H, Kasai T, Ohmichi T, et al. Quantification of plasma phosphorylated tau to use as a biomarker for brain alzheimer pathology: pilot case-control studies including patients with alzheimer’s disease and down syndrome. Mol Neurodegeneration. 2017;12(1):63.
   PubMedGoogle Scholar
• Suzuki M, Ito K, Kato T, et al. 11C-labelled catechol derivative, positron emission tomography (pet) probe for phosphorylated tau aggregation inhibitor using same, and production methods therefor. WO2018/008552Al; 2018.
   Google Scholar
• Yu W, Zhang L, Wei Q, et al. O6-Methylguanine-DNA methyltransferase (MGMT): challenges and new opportunities in glioma chemotherapy. Front Oncol. 2020;9:1547.
   PubMed Web of Science ®Google Scholar
• Suzuki M, Ito K, Natsume A, et al. Method for producing a 11 C-labelled o6-benzylguanine. WO2018/008311; 2020
   Google Scholar
• Beurel E, Grieco SF, Jope RS. Glycogen Synthase Kinase-3 (GSK3): regulation, actions, and diseases. Pharmacol Ther. 2015;148:114–131.
   PubMed Web of Science ®Google Scholar
• Farhad K, Bengt L. 11C/18F-labeled inhibitors of glycogen synthase kinase-3. US8226927 B2. 2012.
   Google Scholar
• Marie Y, Carpentier AF, Omuro AMP, et al. EGFR tyrosine kinase domain mutations in human gliomas. Neurology. 2005;64(8):1444–1445.
   PubMed Web of Science ®Google Scholar
• Yexing G, Manquan WX. 11C-labeled EGFR positron tracer, its preparation method and application in drug AZD9291 therapeutic evaluation, treatment monitoring and mechanism research. CN109942550A. 2019.
   Google Scholar
• Tang G. Positron isotope labeled dansyl acylamino diphenylethylene compound, synthetic method and application thereof. CN106581701A. 2017
   Google Scholar
• Du Q, Liao Q, Chen C, et al. The role of transient receptor potential vanilloid 1 in common diseases of the digestive tract and the cardiovascular and respiratory system. Front Physiol. 2019;10:1064.
   PubMed Web of Science ®Google Scholar
• Doi H, Watanabe Y, Tateishi U, et al. Preparation of (2E)-3-(4-Chlorophenyl)-N-(3-hydroxyphenyl)-2-propenamide derivatives labeled with fluorine-18 or carbon-11 as positron emission tomography imaging agents for intracerebral TRPV1 receptor. WO2020/017557. 2020.
   Google Scholar
• de Oliveira, GAP and Silva JL. Alpha-synuclein stepwise aggregation reveals features of an early onset mutation in parkinson’s disease. Commun Biol. 2019;2(1):374.
   PubMedGoogle Scholar
• Giese A, Schmidt F, Weckbecker D, et al. Novel compounds for the diagnosis, treatment and prevention of diseases associated with the aggregation of alpha-synuclein. WO2021/099518. 2021.
   Google Scholar
• Swanson GT, Sakai R. Ligands for ionotropic glutamate receptors. In: Marine toxins as research tools book. Vol. 46. USA: Springer; 2009. p. 123–157.
   Google Scholar
• Kew JNC, Kemp JA. Ionotropic and metabotropic glutamate receptor structure and pharmacology. Psychopharmacology (Berlin). 2005;179(1):4–29.
   PubMed Web of Science ®Google Scholar
• Andres G, Jose I, Alcazar V, et al. Radiolabelled mglur2 pet ligands. WO2012/062752Al. 2012.
   Google Scholar
• Oi N, Yamamoto N, Suzuki M, et al. Carbon-11 and fluorine-18 labeled l,3-diphenyl-5-(pyrimidin-2-yl)-pyridin-2(l H)-one derivatives for PET imaging of the AMPA receptors. WO2014/163210Al. 2014
   Google Scholar
• Kojima Y, Nakagami Y. Preparation of 1-11C-fumaric acid for positron emission tomography (PET). JP2016050176A. 2016.
   Google Scholar
• Chandra KM, Goud NS, Arifuddin M, et al. Synthesis and biological evaluation of novel 4,7-disubstituted coumarins as selective tumor-associated carbonic anhydrase IX and XII inhibitors. Bioorg Med Chem Lett. 2021;39:127877.
   PubMed Web of Science ®Google Scholar
• Narella SG, Shaik MG, Mohammed A, et al. Synthesis and biological evaluation of coumarin-1,3,4-oxadiazole hybrids as selective carbonic anhydrase IX and XII inhibitors. Bioorg Chem. 2019;87:765–772.
   PubMed Web of Science ®Google Scholar
• Guo Q, Xin J. Fully automatic synthesis method for positron tracer of 11C-labeled acetazolamide-type water channel protein inhibitor. CN103641796A. 2014.
   Google Scholar
• Watanabe Y, Suzuki M, Doi H. 11C-labeled thiamine and its derivatives, 11C-labeled fursultiamine, thiamine precursors, PET probes, and their use for imaging method. JP2013213027A. 2013.
   Google Scholar
• Gandhi PN, Chen SG, Wilson-Delfosse AL. Leucine-Rich Repeat Kinase 2 (LRRK2): a key player in the pathogenesis of parkinson’s disease. J Neurosci Res. 2009;87(6):1283–1295.
   PubMed Web of Science ®Google Scholar
• Greggio E, Cookson MR. Leucine-rich repeat kinase 2 mutations and parkinson’s disease: three questions. ASN Neuro. 2009;1(1):AN20090007.
   Web of Science ®Google Scholar
• Chan BK, Estrada A, Marik J. Fluorine-18 and carbon-11 (PET) imaging for lrrk2 labeled radioligands for positron emission tomography. WO2013/079496Al; 2013.
   Google Scholar
• Dong M, Yan BP, Liao JK, et al. Rho-kinase inhibition: a novel therapeutic target for the treatment of cardiovascular diseases. Drug Discov Today. 2010;15(15–16):622–629.
   PubMed Web of Science ®Google Scholar
• Breitenlechner C, Gaßel M, Hidaka H, et al. Protein kinase a in complex with rho-kinase inhibitors Y-27632, fasudil, and H-1152P. Structure. 2003;11(12):1595–1607.
   PubMed Web of Science ®Google Scholar
• Suzuki M, Hidaka H. 11C-labeled isoquinolines, their preparation, precursors, and their use for PET probes and tissue imaging. JP201304011A. 2013.
   Google Scholar
• Kruger U, Lade O, Steckenborn A, et al. 11C-labelled peptide for detecting neurons which express an acetylcholine receptor. WO2012/000784Al. 2012.
   Google Scholar
• Kolb HC, Kruger C, Lade O, et al. 11C-labelled peptide for detecting a tumour which expresses a somatostatin receptor. WO2012/000781A2. 2012.
   Google Scholar
• Lade O, Hiss JA, Kolb HC, et al. 11C-labelled peptide for detecting a diseased tissue. WO2012/000866Al. 2012.
   Google Scholar
• Herberg F, Kolb KC, Kruger U, et al. 11C-marked peptide for detecting a tumor that expresses an HER2/NEU receptor. WO2012/000865Al. 2012.
   Google Scholar
• Gobbi L, Knust H, Koerner M, et al. 2-phenylimidazo [1,2-a] pyrimidines as imaging agents. DK2999701T3. 2014.
   Google Scholar