Synthesis of combretastatin A-4 prodrugs and trans-isomers...

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Phosphorus containing other than solely as part of an...

Reexamination Certificate

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C558S197000

Reexamination Certificate

active

11364733

ABSTRACT:
Combretastatin A-4 has been previously selected for pre-clinical development as antineoplastic agent. However, it is essentially insoluble in water. New water soluble derivatives of combretastatin A-4 and its qualified analogs have been discovered and synthesized through a multistage process using other derivatives of combretastatin A-4 as intermediates. These water soluble derivatives are herein denominated as “Combretastatin A-4 Prodrugs”.

REFERENCES:
patent: 5484799 (1996-01-01), Hochlowski et al.
Petit et al, Anti-Cancer Drug Design, Antineoplastic agents. 322. Synthesis of combretastatin A-4 prodrugs, 1995, 10(4), pp. 299-309.
CA:123:227731 abs of Anti Cancer Drug Design by Pettit et al. 10(4) pp. 200-309 (1995).
Atherton et al., “Studies on Phosphorylation. Part III. Further Observations on the Reaction of Phosphites with Polyhalogen Compounds in Presence of Bases and its Application to the Phosphorylation of Alcohols”,Journal of the Chemical Society, pp. 674-678, (1947).
Brown, R.T.; Fox, B.W.; Hadfield, J.A.; McGown, A.T.; Mayalarp, S.P.; Pettit, G.R.; and Woods, J.A., “Synthesis of Water-Soluble Sugar Derivatives of Combretastatin A-4”,Journal of the Chemical Society, Perkin Transactions I, vol.—(1995), pp. 577-.
Bedford, S.B.; Quarterman, C.P.; Rathbone, D.L.; Slack, J.A.; Griffin, R.J.; and Stevens, M.F.G., “Synthesis of Water-Soluble Prodrugs of the Cytotoxic Agent Combretastatin A-4”Bioorganic&Medicinal Chemistry Letters, vol. 6, No. 2, pp. 157-160, (1996).
Silverberg, L.J.; Dillon, J.L.; Vemishetti, P., “A Simple, Rapid and Efficient Protocol for the Selective Phosphorylation of Phenols with Dibenzyl Phosphite”,Tetrahedron Letters, vol. 37, No. 6, pp. 771-774 (1996).
Dorr, R.T.; Dvorakova, K.; Snead, K.; Alberts, D.S.; Salmon, S.E.; Pettit, G.R., “Antitumor activity of combretastatin A-4 Phosphate, A Natural Product Tubulin Inhibitor”,Investigational New Drugs, vol. 14, pp. 131-137 (1996).
Pettit, G.R.; Rhodes, M.R., “Antineoplastic Agents 389. New Syntheses of the Combretastatin A-4 Prodrug”,Anti-Cancer Drug Design, vol. 13, No. 3, pp. 183-191 (1998).
Pettit, G.R.; Rhodes, M.R., “Antineoplastic Agents 393. Synthesis of thetrans-isomer of Combretastatin A-4 Prodrug”,Anti-Cancer Drug Design, vol. 13, No. 8, pp. 981-993 (1998).
Pettit, G.R.; Toki, B.; Herald, D.L.; Verdier-Pinard, P.; Boyd, M.R.; Hamel, E.; and Pettit, R.K., “Antineoplastic Agents. 379. Synthesis of Phenstatin Phosphate”,Journal of Medicinal Chemistry, vol. 41, No. 10, pp. 1688-1695 (1998).
Ohsumi, K.; Hatanaka T.; Nakagawa, R.; Fukuda, Y.; Morinaga, Y.; Suga, Y.; ;Nihei, Y.; Ohishi, K.; Akiyama, Y.; and Tsuji, T., “Synthesis and Antitumor Activities of Amino Acid Prodrugs of Amino-Combretastatins”,Anti-Cancer Drug Design, vol. 14, pp. 539-548 (1999).
Pettit, G.R.; Lippert III, J.W., “Antineoplastic Agents 429. Syntheses of the Combretastatin A-1 and Combretastatin B-1 Prodrugs”,Anti-Cancer Drug Design, vol. 15, No. 3, pp. 203-216 (2000).
Pettit, G.R.; Lippert III, J.W.; Boyd, M.R.; Verdier-Pinard, P.; and Hamel, E., “Antineoplastic Agents 442. Synthesis and Biological Activities of Dioxostatin”,Anti-Cancer Drug Design, vol. 15, No. 4, pp. 361-371 (2000).
Pettit, G.R.; Minardi, M.D.; Boyd, M.R.; and Pettit, R.K., “Antineoplastic Agents 463. Synthesis of Combretastatin A-3 Diphosphate Prodrugs”,Anti-Cancer Drug Design, vol. 15, No. 4, pp. 397-403 (2000).
Pettit, G.R.; Graelish, M.P.; Jung, M. K.; Hamel, E.; Pettit, R.K.; Chapuis, J.-C.; and Schmidt, J.M., “Antineoplastic Agents. 465. Structural Modification of Resveratrol: Sodium Resverastatin Phosphate”,Journal of Medicinal Chemistry, vol. 45, No. 12, pp. 2534-2542 (2002).
Hill, S.A.; Chaplin, D.J.; Lewis, G.; Tozer, G.M., “Schedule Dependence of Combretastatin A-4 Phosphate in Transplanted and Spontaneous Tumour Models”,International Journal of Cancer, vol. 102, No. 1, pp. 70-74 (2002).
Dowlati, A.; Robertson, K.; Cooney, M.; Petros, W.P.; Stratford, M.; Jesberger, J., et al., “A Phase I Pharmacokinetic and Translational Study of the Novel Vascular Targeting Agent Combretastatin A-4 Phosphate on a Single-Dose Intravenous Schedule in Patients with Advanced Cancer”,Cancer Research, vol. 62, pp. 3408-3416 (Jun. 15, 2002).
Nabha, S.M.; Mohammad, R.M.; Dandashi, M.H.; Coupaye-Gerard, B.; Aboukameel, A.; Pettit, G.R.; and Al-Katib, A.M., “Combretastatin A-4 Prodrug Induces Mitotic Catastrophe in Chronic Lymphocytic Leukemia Cell Line Independent of Caspase Activation and Poly(ADP-ribose) Polymerase Cleavage”,Clinical Cancer Research, vol. 8, pp. 2735-2741 (Aug. 2002).
Hadiman, M.B., et al., “Synthesis, In Vitro, and In Vivo Evaluation of Phosphate Ester Derivatives of Combretastatin A-4”,Bioorganic&Medicinal Chemistry Letters, vol. 13, No. 9, pp. 1505-1508 (2003).
Ahmed, B.; Van Euk, L.I., et al., “Vascular Targeting Effect of Combretastatin A-4 Phosphate Dominates the Inherent Angiogenesis Inhibitory Activity”,International Journal of Cancer, vol. 105, No. 1, pp. 20-25 (2003).

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