Radiopharmaceutical and methods of synthesis and use thereof

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C424S001370, C424S009100, C546S048000, C514S284000

Reexamination Certificate

active

11110279

ABSTRACT:
A novel group of apomorphine derivatives are provided that are well suited as radioimaging agents upon incorporation of radionuclides. Through reaction of D ring sites, the less reactive sites of the apomorphine A ring is modified in ways previously unattainable.

REFERENCES:
Simon, C. et al.: Synthesis of C-3 halogen-substituted apocodeines and apomorphines. Synthetic Commun. vol. 21, pp. 2309-2316, 1991.
Hussain, S.F. et al.: A new pentasubstituted aporphine: (+)-N-methyldanguyelline. J. of Natural Products, vol. 52, pp. 428-429, 1989.
Sheppard, H. et al.: The dopamine-sensitive adenylate cyclase of the rat caudate nucleus. Biochemical Pharmacol. vol. 27, pp. 1113-1116, 1978.
Vasdev et al., Selectivity of [F]F2 towards L—Methyltyrosine and L-Tyrosine: A Radiochemical and NMR Spectroscopic Study; J. Labelled Cpd. Radiopharm 44, Suppl.1 2001 S863-S865.
2004 American Chemical Society; pp. 1-29; Absolute Chemistry.
Ajao et al., The Preparation and Oxidative Dimerisation of 2-Acetyl-7-hydroxy-1,2,3,4-tetrahydroisoquinoline Synthesis; Dept. of Chem, Queen Elizabeth College, London,EnglandMar.-Apr. 1984; pp. 329-331.
Langer et al.,Preparation of 4- and 6- [Br]Bromometaraminol, Two Pet Tracers for the Adrenergic Nerve Sysem, J. Labelled Cpd. Radiopharm 40, (1997) 117-119.
DeVos et al., Synthesis of Iodoaminoglutethimide, a Possible Radioligand for the Visualisation of the Aromatase Enzyme in Breast Carcinoma by Spect, J. Labelled Cpd. Radiopharm 40, (1997) 375-376.
C Loc'h et al, Preparation and Preliminary Evaluation of 3-threo Bromomethylphenidate Enantiomers; Potential Tracers for PET Study of Dopamine Reuptake Sites, J. Labelled Cpd. Radiopharm 42, (1999) S42-S44.
Pacer et al., Synthesis of 1-(3-[F]Fluorobenzly)-4-[2(N-Phthalimid-1-yl)Ethyl] Piperidine, J. Labelled Cpd. Radiopharm 44, Suppl.1 (2001); S920-921.
Constantinou et al., Improved Preparation of [F] Xenon Difluoride from [F] Fluoride for Labelling Reactions; J. Labelled Cpd. Radiopharm 42, Suppl 1 (1999), S530-532.
Filer et al., Preparation of (−)-[8,9-H]Apomorphine at High Specific Activity, Journal of Organic Chemistry 1980, 45, 3918-3919.
Cramer et al., Gas Phase Fluorination of Benzene, Fluorobenzene, m-Difluorobenzene and Trifluoromethylbenzene by Reactions of Thermal Fluorine-18 Atoms, Dept of Chemistry, University of CA, Irvine, CA Mar. 12, 1974, 6579-6584.
Berenyi et al.,A New Efficient Method for the Preparation of 2-Fluoro-N-propylnorapomorphine, J.Chem. Soc. Perkin Trans, Jan. 1992, 2693-2694.
Fuchtner et al., 3-O-Methyl-6-[F]Fluoro-L-Dopa-A Promising Substance for Tumour Imaging, J. Labelled Cpd. Radiopharm 42, Suppl. 1 (1999), S267-269.
John et al., Synthesis, Characterization and Initial Clinical Evaluation of 3-[123I]Iodo-N-[2-(1-Piperidinyl) Ethyl]4-Methozybenzamide, [123I] Pimba in Breast Cancer Patients,J. Labelled Cpd. Radiopharm. 42, Suppl. 1 (1999) S261-263.
Nagasawa et al., Synthesis and Dopamine Receptor Affinity of (R)-(−)-2Fluro-N-n-propylnorapomorphine: A Highly Potent and Selective Dopamine D Agonist, J. Med. Chem. 1990, 33, 3122-3124.
Baldessarini et al., R(−) Fluoro-N-Propylnorapomorphine a very Potent and D2-Selective Dopamine Agonist, Neuropharmacology, vol. 30, No. 1, 97-99, 1991.
Vasdev, Synthesis of Fluorine-18 Labeled 5—Fluoro-L-Dopa by Direct Fluorination of L-Dopa, J Labelled Cpd. Radiopharm, 42, Suppl 1(1999), S486-488.
Windhorst et al., Radiosynthesis and Biodistribution of I Labeled Antagonists as Potential Spect Ligands for the Histamine H3 Receptor, J. Labelled Cpd. Radiopharm, 42, Suppl. 1 (1999), S282-283.
Gillings et al., An Improved Synthesis and Evaluation in Pig Brain of the Dopamine Agonist Ligand: R-[N-Methyl-C] Apmorphine, J. Labelled Cpd. Radiopharm, 44, Suppl. 1(2001), S210-212.
Ramsby et al., 2-Haloaporphines as Potent Dopamine Agonists, J. Med. Chem 1989, 32, 1198-1201.
Morin et al., N-Monofluoroalkylnoraporphines Synthesis and Binding Dopamine Receptor Studies, Med. Chem Res (1992) 2:354-360 1992.
Tierling et al., A New Nucleophilic Asymmetric Synthesis of 6-[F] Fluoro-Dopa, J. Labelled Cpd. Radiopharm. 44, Suppl. 1 (2001), S146-147.
Weisbach et al., Studies in the Synthesis and Pharmacology of Aporphines, Journal of Medicinal Chemistry, vol. 6, No. 2, Mar. 6, 1963, 91-97.
Zijlstra et al., Synthesis and In Vivo Distribution in the Rat of Several Fluorine-18 Labeled N-Fluoroalkylaporphines, Appl. Radiat. Isot. vol. 44, No. 4, 651-658, 1993.
Cumming et al., Kinetics of the uptake and distribution of the dopamine D2,3 agonist (R)-N-[1-11C]n-propylnorapomorphine in brain of healthy and MPTP-treated Bottingen miniature pigs, Nuclear Med and Bio 30 (2003) 547-553.
Filer et al., Isoquinolines.7.Reaction of Ethylene Oxide with Ioquinolines. Novel Isoquinolone and Oxazolidine Formation, J. of Organic Chemistry 43, 672 (1978), 673-678.
Filer et al, Aporphines. 28.Preparation of (−)-N-n[3H-and-2H] Propylnorapomorphine, J. Org. Chem. 1980, 45, 3465-3467.
Koziorowski et al., Rapid Preparation of 5-[I]iodo-2-Deoxyuridine by iododestannylation, J. Labelled Cpd. Radiopharm 40, 128 (1997).
Argiolas et al., N-n-Propyl-Norapomorphine: An Extremely Potent Stimulant of Dopamine Autoreceptors, Brain Research, 231 (1982) 109-116.
Hwang et al., (−)-N[C] Propyl-Norapomorphine: A Positron-Labeled Dopamine Agonist for PET Imaging of D2 Receptors, Nuclear Medicine & Biology, vol. 27, pp. 553-539, 2000.
Halldin et al., PET Studies with Carbon-11 Radioligands in Neuropsychopharmacological Drug Developement, Current Pharmaceutical Design, 2001, 7, 1907-1929.

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