Vitamin-targeted imaging agents

Details Vitamin-targeted imaging agents Vitamin-targeted imaging agents

2011-01-04

2011-01-04

Jones, D L (Department: 1618)

Drug, bio-affecting and body treating compositions

In vivo diagnosis or in vivo testing

C424S001110, C424S001650, C424S001730

Reexamination Certificate

active

07862798

ABSTRACT:
The invention relates to compounds and methods for targeting radionuclide-based imaging agents to cells having receptors for a vitamin, or vitamin receptor binding derivative or analog thereof, by using such a vitamin as the targeting ligand for the imaging agent. The invention provides a compound of the formulafor use in such methods. In the compound, V is a vitamin that is a substrate for receptor-mediated transmembrane transport in vivo, or a vitamin receptor binding derivative or analog thereof, L is a divalent linker, R is a side chain of an amino acid of the formula H2NCHRCOOH, M is a cation of a radionuclide, n is 1 or 0, K is 1 or 0, and the compound can be in a pharmaceutically acceptable carrier therefor. The vitamin-based compounds can be used to target radionuclides to cells, such as a variety of tumor cell types, for use in diagnostic imaging of the targeted cells.

REFERENCES:
patent: 2816110 (1957-12-01), Sletzinger et al.
patent: 5140104 (1992-08-01), Coughlin et al.
patent: 5552545 (1996-09-01), Pearce et al.
patent: 5688488 (1997-11-01), Low et al.
patent: 6221334 (2001-04-01), Wedeking et al.
patent: 6335434 (2002-01-01), Guzaev et al.
patent: 7128893 (2006-10-01), Leamon et al.
patent: 2002/0192157 (2002-12-01), Low et al.
patent: 2004/0033195 (2004-02-01), Leamon et al.
patent: 0273085 (1987-04-01), None
patent: 0220030 (1988-07-01), None
patent: 2774378 (1998-04-01), None
patent: 92/13572 (1992-08-01), None
patent: WO 98/49196 (1998-11-01), None
patent: WO-9849196 (1998-11-01), None
patent: WO 00/73332 (2000-12-01), None
patent: WO 01/91807 (2001-12-01), None
patent: WO 02/087424 (2002-11-01), None
patent: WO 2004/069159 (2004-08-01), None
patent: WO 2004/100983 (2004-11-01), None
Leamon C.P. et al., “Synthesis and Biological Evaluation of EC20: A New Folate-Derived, 99mTc-Based Radiopharmaceutical.”,Bioconjugate Chem., 2002, vol. 13, No. 6, November-December, pp. 1200-1210.
Yang, D. J. et al., “Imaging-Tumor Folate Receptors Using Radiolabeled Folate and Methotrexate.”Journal of Labelled Compounds and Radiopharmaceuticals, 1999, Sussex, GB, vol. Supp. 1, No. 42, June, pp. S696-S697.
Ilgan et al., “Imaging tumor folate receptors using 111IN-DTPA-methotrexate.”Cancer Biother. Radiopharm., 1998, 13(3) pp. 177-184.
Akihiro H. et al., “Affinity for a-tocopherol transfer protein as a determinant of the biological activities of vitamin E analogs.”Federation of European Biochemical Societies, 1997, vol. 409, pp. 105-108.
Kazui S. et al., “Novel vitamin D3 antipsoriatic antedrugs: 16-En-22-oxa-1a,25-(OH)2D3 analogs,”Bioorganic&Medicinal Chemistry, 2006, vol. 14, pp. 1838-1850.
Hisashi T. et al., “c-Fos protein as a target of anti-osteoclastogenic action of vitamin D, and synthesis of new analogs,” journal article,The Journal of Clinical Investigation, 2006, vol. 116, No. 2, February, pp. 528-535.
Masato S. et al., “Synthesis and biological activities of new 1a,25-dihydroxy-19-norvitamin D3 analogs with modifications in both the A-ring and the side chain,” journal article,Bioorganic&Medicinal Chemistry, 2006, 14(12) pp. 4277-4294.
Agoston E.S. et al., “Vitamin D Analogs as Anti-Carcinogenic Agents”Anti-Cancer Agents in Medicinal Chemistry 2006, 6(1), pp. 53-71.
Westerhof G.R. et al. “Carrier-and Receptor-Mediated Transport of Folate Antagonists Targeting Folate-Dependent Enzymes: Correlates of Molecular-Structure and Biological Activity,”Molecular Pharmacology, 1995, vol. No. 48, pp. 459-471.
Roberts, E.C. et al., “Folic Acid Analogs. Modification in the Benzene-Ring Region. 3. Neohomofolic and Neobishomofolic Acids. An Improved Synthesis of Folic Acid and Its Analogs,”J. Med. Chem., 1973, vol. 16, No. 6, pp. 697-699.
Roberts, E.C. et al., “Folic Acid Analogs. Modifications in the Benzene-Ring Region. 2. Thiazole Analogs,”J. Med. Chem., 1972, vol. 15, No. 12, pp. 1310-1312.
Roberts, E.C. et al., “Folic Acid Analogs. Modifications in the Benzene-Ring Region. 1. 2′- and 3′-Azafolic Acids,”J. Med. Chem., 1971, vol. 14, No. 2, pp. 125-130.
Weinstock, L.T. et al., “Folic Acid Analogs. II. p{[2,-6-Diamino-8-purinyl)methyl]amino}-benzoyl-L-glutamic Acid and Related Compounds,”J. Med. Chem., 1970, vol. 13, No. 5, pp. 995-997.
Bock, L. et al., “Sulfonamide Structure-Activity Relationships in a Cell-Free System. 2. Proof for the Formation of a Sulfonamide-Containing Folate Analog,”J. Med. Chem., 1974, vol. 17, No. 1, pp. 23-28.
Roberts, E.C. et al., “Folic Acid Analogs. Modifications in the Benzene-Ring Region. 4. 3′-Ethyl- and 3′Isopropylfolic Acids,”J. Med. Chem., 1974, vol. 17, No. 2, pp. 219-222.
Lee, W.W. et al., “Folic Acid Antagonists. Methotrexate Analogs Containing Spurious Amino Acids. Dichlorohomofolic Acid,”J. Med. Chem., 1974, vol. 17, No. 3, pp. 326-330.
Kim, Y.H. et al., “Synthesis and Biological Activity of 10-Thia-1-deaza Analogs of Folic Acid, Pteroic Acid, and Related Compounds,”J. Med. Chem., 1975, vol. 18, No. 8, pp. 776-780.
Nair, M.G. et al., “Folate Analogues Altered in the C9-N10 Bridge Region. 10-Oxafolic-Acid and 10-Oxaaminopterin,”J. Med. Chem., 1976, vol. 19, No. 6, pp. 825-829.
Plante, L.T. et al., “Polyglutamyl and Polylysyl Derivatives of the Lysine Analogies of Folic Acid and Homofolic Acid,”J. Med. Chem., 1976, vol. 19, No. 11, pp. 1295-1299.
Hynes, J.B., et al., “Quinazolines as Inhibitors of Dihydrofolate Reductase. 4. Classical Analogues of Folic and Isofolic Acids.”J. Med. Chem., 1977, vol. 20, No. 4, pp. 588-591.
Oatis, J.E., et al., “Synthesis of Quinazoline Analogues of Folic Acid Modified at Position 10.”J. Med. Chem., 1977, vol. 20, No. 11, pp. 1393-1396.
Nair, M.G. et al., “Folate Analogues Altered in the C9-N10 Bridge Region: N10-tosylisohomofolic Acid and N10-Tosylisohomoaminopterin.”J. Med. Chem., 1978, vol. 21, No. 7, pp. 673-677.
Nair, M.G. et al., “Folate Analogues Altered in the C9-N10 Bridge Region: 11-Thiohomofolic Acid.”J. Med. Chem., 1979, vol. 22, No. 7, pp. 850-855.
Nair, M.G. et al., “Folate Analogues Altered in the C9-N10 Bridge Region: 14. 11-Oxahomofolic Acid, a Potential Antitumor Agent.”J. Med. Chem., 1980, vol. 23, pp. 59-65.
Nair, M.G. et al., “Folate Analogues Altered in the C9-N10 Bridge Region: 18. Synthesis and Antitumor Evaluation of 11-Oxahomoaminopterin and Related Compounds,”J. Med. Chem., 1981, v ol. 24, pp. 1068-1073.
Temple Jr., C.I et al., “Synthesis of Pseudo Cofactor Analogues as Potential Inhibitors of the Folate Enzymes.”J. Med. Chem., 1983, vol. 25, pp. 161-166.
Nair, M.G. et al., “Folate Analogues. 20. Synthesis and Antifolate Activity of 1, 2, 3, 4, 5, 6-Hexahydrohomofolic Acid.”J. Med. Chem., 1983, vol. 26, pp. 135-140.
Nair, M.G. et al., “Folate Analogues. 21. Synthesis and Antifolate and Antitumor Activities of N10-(Cyanomethyl)-5,8-dideazafolic Acid.”J. Med. Chem., 1983, vol. 26, pp. 605-607.
Nair, M.G. et al., “Folate Analogues. 22. Evaluation of Two Analogues of Dihydrofolic Acid Processing a 7,8-Dihydro-8-oxapterin Ring System.”J. Med. Chem., 1983, vol. 26, pp. 1164-1168.
Lonsdale, D., “A Review of the Biochemistry, Metabolism and Clinical Benefits of Thiamin(e) and Its Derivatives.”Evidence-Based Complementary&Alternative Medicine:e CAM. Advance Access Publication, vol. 3, Feb. 2006, pp. 49-59.
Nosaka, K. et al., “Separate Determination of Anticoccidial Thiamine Analogs by High-Performance Liquid Chromatography.”ActaA Vitaminol. Et Enzymol., 1984, vol. 6 92), pp. 137-142.
Kandiko, C.T. et al., “Inhibition of Rat Brain Pyruvate Dehydrogenase by Thiamine Analogs.”Biochem. Pharmacology, vol. 37, No. 22, (1988) pp. 4375-4380.
Spry, C. et al., “A Class of Pantothenic Acid Analogs Inhibits Plasmodium

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