Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Halogenated hydrocarbon doai
Reexamination Certificate
2007-05-22
2007-05-22
Jiang, Shaojia Anna (Department: 1623)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Halogenated hydrocarbon doai
C514S730000, C514S743000, C514S748000, C514S750000, C514S751000, C514S754000, C568S300000, C568S579000, C568S626000, C568S630000, C568S631000, C568S644000, C568S645000, C570S123000, C570S124000, C570S127000, C570S128000, C570S129000
Reexamination Certificate
active
10451213
ABSTRACT:
The present invention relates to stilbene and quinone compounds related to combretastatin A-4 and their use as anticancer compounds and prodrugs. The compounds include those with an alkyl group on the double bond of cis or trans-stilbenes, compounds with one or more (and preferably 2 or 3) alkyl group substituents on the stilbene A ring, compounds with an alkoxy group other than methoxy at position 3, 4, and/or 5 of the stilbene A ring, compounds (or prodrugs) in which BOC amino acid esters are formed with the phenolic hydroxyl at the 3-position of the B ring and compounds (or prodrugs) based on a benzoquinone B ring. The present invention further relates to the photochemical reactions of stilbene compounds, either the above compounds disclosed for the first time herein or compounds based on prior art stilbenes. These reactions include the photochemical release of an active form of the compound from a prodrug conjugate and the photochemical isomerisation of the compounds, especially from a trans to cis form of compounds. The reactions can be used alone or in combination to convert inactive or comparatively less active forms of the compounds to more active forms, thereby allowing the compounds to be selectively targeted, e.g. activating them at the site of a tumour.
REFERENCES:
patent: 4996237 (1991-02-01), Pettit et al.
patent: 5430062 (1995-07-01), Cushman et al.
patent: 5561122 (1996-10-01), Pettit
patent: 5569786 (1996-10-01), Pettit et al.
patent: 0 641 767 (1994-09-01), None
patent: WO 92/16486 (1992-10-01), None
patent: WO 99/35150 (1999-07-01), None
patent: WO 00/48590 (2000-08-01), None
Badjic et al., “Unexpected Interactions between Sol-Gel Silica Glass and Guest Molecules. Extraction of Aromatic Hydrocarbons into Polar Silica from Hydrophobic Solvents”, Journal of Physical Chemistry B, vol. 104, Nov. 1, 2000, pp. 11081-11087.
Pettit, G.R., et al., “Isolation and structure of the strong cell growth and tubulin inhibitor combretastatin A-4”, Experientia 45:209-211 (1989).
Lin, C.M., et al., “Interactions of Tubulin with Potent Natural and Synthetic Analogs of the Antimitotic Agent Combretastatin: a Structure-Activity Study”, Mol. Pharmacol., 34:200-208 (1988).
Grosios, K., et al., “In vivo and in vitro evaluation of combretastatin A-4 and its sodium phosphate prodrug”, British J. of Cancer, 81(8): 1318-1327 (1999).
Lin, C.M., et al., “Antimitotic Natural Products Combretastatin A-4 and Combretastatin A-2: Studies on the Mechanism of Their Inhibition of the Binding of Colchicine to Tubulin”, Biochemistry 28: 6984-6991 (1989).
Woods, J.A., et al., “The interaction with tubulin of a series of stilbenes based on combretastatin A-4”, British Journal of Cancer, 71: 705-711 (1995).
McGown, A.T., et al., “Differential cytotoxicity of Combretastatins A1 and A4 in two daunorubicin-resistant P388 cell lines”, Cancer Chemother. Pharmacol. 26: 79-81 (1990).
El-Zayat, A.A.E., et al., “In vitro evaluation of the antineoplastic activity of combretastatin A-4, a natural product from Combretum caffrum (arid shrub)”, Anti-Cancer Drugs 4: 19-25 (1993).
Dark, G.G., et al, “Combretastatin A-4, an Agent That Displays Potent and Selective Toxicity toward Tumor Vasculature”, Cancer Research, 57: 1829-1834, (1997).
Brown, R.T., et al., “Synthesis of Water-soluable Sugar Derivatives of Combretastatin A-4”, J. Chem. Soc. Prekin Trans., 1: 577-581 (1995).
Pettit, G.R., et al., “Antineoplastic agents 322. Synthesis of combretastatin A-4 prodrugs”, Anti-Cancer Drug Design, 10: 299-309 (1995).
Ducki, S., et al., “Potent Antimitotic and Cell Growth Inhibitory Properties of Substituted Chalcones”, Bioorganic & Medicinal Chemistry Letters, 8: 1051-1056 (1998).
Zhao, S., et al., “Positron emission tomography of murine liver metastases and the effects of treatment by combretastatin A-4”, European Journal of Nuclear Medicine, 26: 231-238 (1999).
Aleksandrzak, K., et al., “Antimitotic activity of diaryl compounds with structural features resembling combretastatin A-4”, Anti-Cancer Drugs 9: 545-550 (1998).
Holmes, C.P., “Model Studies for New o-Nitrobenzyl Photolabile Linkers: Substitutent Effects on the Rates of Photochemical Cleavage”, J. Org. Chem., 62: 2370-2380 (1997).
Pettit, G.R., et al., “Antineoplastic Agents. 291. Isolation and Synthesis of Combretastatins A-4, A-5, and A-6”, J. Med. Chem., 38: 1666-1672 (1995).
Irngartinger, H., et al., “Synthesis, Structures and Topochemistry of 2-Monovinyl-Substituted 1,4-Bezoquinones”, Eur. J. Org. Chem., p. 605-626, (1998).
Sisido, K., et al., “The Preparation of Synthetic Estrogens. IV. Condensation of Biacetyl with Phenois”, J. American Chemical Society, 71: 2037-2041 (1949).
Pinney, K.G., et al., “Synthesis and Biological Evaluation of Aryl Azide Derivatives of Combretastatin A-4 as Molecular Probes for Tubulin”, Bioorganic & Medicinal Chemistry vol 8: 2417-2425 (2000).
Pettit, G.R., et al., “Antineoplastic agents 429. Syntheses of the combretastatin A-1 and combretastatin B-1 prodrugs”, Anti-Cancer Drug Design, vol. 15: 203-216 (2000).
Ward, W.J., et al., “Metal Ion Effects in Wittig Reactions: A General Hypothesis for the Mechanism of the Wittig Reaction”, J. Org. Chem., 55: 493-500 (1990).
Letcher, R.M., et al., “Chemical Consitutents of the Combretaceae, Part II. Substituted Phenanthrenes and 9,10-Dihydrophenanthrenes and a Substituted Bibenzyl from the Heartwood of Combretum molle”, Journal of the Chemical Society, Perkin Transactions I, p. 206-210, Lechtworth GB (1972).
Letcher, R.M., et al., “Chemical Constituents of the Combretaceae. Part III. Substituted Phenanthrenes, 9,10-Dihydrophenanthrenes, and Bibenzyls from the Heartwood of Combretum psidioides”, Journal of Chemical Society Perkin Transaction I, p. 2941-2946, Lechworth GB (1972).
Battersby, A.R., et al., “cis- and trans-3,3′,4,4′-Tetramethoxystilbenes”, J. Chem. Soc. P. 2592-2593 (1961).
Walker, G.N., “Hypotensive Methoxyisoquinolines”, J. Am. Chem. Soc., vol. 76: p. 3999-4003 (1954).
Butler John
Gaukroger Keira
Hadfield John Anthony
Hamblett Ian
Hepworth Lucy Annette
Dann Dorfman Herrell and Skillman, P.C.
Hagan, Esq. Patrick J.
Jiang Shaojia Anna
McIntosh Traviss
LandOfFree
Substituted stilbenes and their reactions does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Substituted stilbenes and their reactions, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Substituted stilbenes and their reactions will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3809218