Bryostatin analogues, synthetic methods and uses

Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...

Reexamination Certificate

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C549S267000

Reexamination Certificate

active

10366776

ABSTRACT:
Biologically active compounds related to the bryostatin family of compounds, having simplified spacer domains and/or improved recognition domains are disclosed, including methods of preparing and utilizing the same.

REFERENCES:
patent: 4560774 (1985-12-01), Pettit et al.
patent: 4611066 (1986-09-01), Pettit et al.
patent: 4833257 (1989-05-01), Pettit et al.
patent: 5072004 (1991-12-01), Pettit
patent: 5328929 (1994-07-01), Pettit et al.
patent: 5358711 (1994-10-01), May et al.
patent: 5891870 (1999-04-01), Dreidger et al.
patent: 6043270 (2000-03-01), Driedger et al.
patent: 6060505 (2000-05-01), Blumberg et al.
patent: 6624189 (2003-09-01), Wender et al.
patent: 2003/0199469 (2003-10-01), Schwartz et al.
patent: 2003/0233000 (2003-12-01), Lindquist et al.
patent: 0264173 (1988-04-01), None
patent: 0324574 (1993-11-01), None
patent: WO 01/11024 (2001-02-01), None
Wender et al., Selective Binding of Bryostatin Analogues to the Cysteine Rich Domains of Protein Kinase C Isozymes, Bioorganic & Medicinal Chemistry Letters, vol. 9, No. 12, pp. 1687-1690, Jun. 1999.
Wender et al., Synthesis and Biological Evaluation of a New Class of Bryostatin Analogues: the Role of the C20 Substituent in Protein Kinase C Binding, Tetrahedron Letters, vol. 41, No. 35, pp. 6725-6729, Aug. 2000.
Pettit, G.R., “The bryostatins,”Fortschritte der Chemie Organischer Naturstoffe—Progress in the Chemistry of Natural Products, 57:153-195 (1991).
Registry printout of Bryostatin 4, 5, 10 and 15, 2003.
Baryza, J.L.; Brenner, S.E.; Craske, M.L.; Meyer, T.; Wender, P.A., “Simplified Analogs of Bryostatin with Anticancer Activity Display Greater Potency for Translocation of PKCδ-GFP”,Chemistry&Biology, vol. 11; pp. 1261-1267 (2004).
Evans, D.A.; Carter, P.H.; Carreira, E.M.; Prunet, J.A.; Charette, A.B.; Lautens, M., “Asymmetric Synthesis of Bryostatin 2”,Angew. Chem. Int. Ed. Engl., vol. 37 (17); pp. 2354-2359 (1998).
Evans, D.A.; Carter, P.H.; Carreira, E.M.; Charette, A.B.; Prunet, J.A.; Lautens, M., “Total Synthesis of Bryostatin 2”,J. Am. Chem. Soc., vol. 121; pp. 7540-7552 (1999).
Hale, K.J.; Hummersone, M.G.; Bhatia, G.S., “Control of Olefin Geometry in the Bryostatin B-Ring through Exploitation of a C2-Symmetry Breaking Tactic and a Smith-Tietze Coupling Reaction”,Organic Letters, vol. 2; pp. 2189-2192 (2000).
Hale, K.J.; Frigerio, M.; Manaviazar, S.; Hummersone, M.G.; Fillingham, I.J.; Barsukov, I.G.; Damblon, C.F.; Gescher, A.; Roberts, G.C.K., “Synthesis of a Simplified Bryostatin C-Ring Analogue That Binds to the CRD2 of Human PKC-α and Construction of a Novel BC-Analogue by an Unusual Julia Olefination Process”,Organic Letters, vol. 5; pp. 499-502 (2003).
Hale, K.J.; Frigerio, M.; Manaviazar, S., “New, Abridged Pathway to Masamune's “Southern Hemisphere” Intermediate for the Total Synthesis of Bryostatin 7” ,Organic Letters, vol. 5; pp. 503-505 (2003).
Harada, T.; Inoue, A.; Wada, I.; Uchimura, J-J.; Tanaka, S.; Oku, A., “Stereoselective Acetilization of 1,3-Alkanediols Controlled by Intramolecular van der Waals Attractive Interactions and Its Application to an Enantiodifferentiating Transformation of σ-Symmetric 1,3,5-Pentanetriols”,J. Am. Chem. Soc., vol. 115; pp. 7665-7674 (1993).
Kageyama, M.; Tamura, T., “Synthesis of Bryostatin 7”,J. Am. Chem. Soc., vol. 112; pp. 7407-7408 (1990).
López-Pelegrin, J.A.; Wentworth, P.; Sieber, F.; Metz, W.A.; Janda, K.D., “Soluble Polymer-Supported Chemoenzymatic Synthesis of the C21-C27 Fragment of the Bryostatins”,J. Org. Chem., vol. 65; pp. 8527-8531 (2000).
Masamune, S., “Asymmetric Synthesis and Its Applications: Towards the Synthesis of Bryostatin 1”,Pure&Applied Chemistry, vol. 60; pp. 1587-1596 (1988).
Masamune, S., “Asymmetric Synthesis and Its Applications: Towards the Synthesis of Bryostatin 1”,Chimica, vol. 42: pp. 210-211 (1988).
O'Brian, M.; Taylor, N.H.; Thomas, E.J., “Synthesis of the C(1)-C(16) Fragment of Bryostatins”,Tetrahedron Letters, vol. 43: pp. 5491-5494 (2002).
Ohmori, K.; Ogawa, Y.; Obitsu, T.; Ishikawa, Y.; Nishiyama, S.; Yamamura, S., “Total Synthesis of Bryostatin 3”,Angew. Chem. Int. Ed. Engl., vol. 39: pp. 2290-2294 (2000).
Pettit, G.R.; Herald, C.L.; Doubek, D.L.; Herald, D.L., “Isolation and Structure of Bryostatin 1”,J. Am. Chem. Soc., vol. 104: pp. 6846-6848 (1982).
Pettit, G.R., “Progress in the Discovery of Biosynthetic Anticancer Drugs”,J. Natural Products, vol. 59: pp. 812-821 (1996).
Theisen, P.D.; Heathcock, C.H., “Improved Procedure for Preparation of Optically Active 3-Hydroxyglutarate Monoesters and 3-Hydroxy-5-oxoalkanoic Acids”,J. Org. Chem., Vol. 53: pp. 2374-2378 (1988).
Vakalopoulos, A.; Lampe, T.F.J.; Hoffmann, H.M.R., “Asymmetric Synthesis of the Northern Half C1-C16of the Bryostatins”,Organic Letters, vol.3: pp. 929-932 (2001).
Voight, E.A.; Roethle, P.A.; Burke, S.D., “Concise Formal Synthesis of the Bryostatin Southern Hemisphere (C17-C27)”,J. Org. Chem., vol. 69: pp. 4534-4537 (2004).
Voight, E.A.; Seradj, H.; Roethle, P.A.; Burke, S.D., “Synthesis of the Bryostatin 1 Northern Hemisphere (C1-C16) via Desymmetrization by Ketalization/Ring-Closing Metathesis”,Organic Letters, vol. 6: pp. 4045-4048 (2004).
Wender, P.A.; Cribbs, C.M.; Koehler, K.F.; Sharkey, N.A.; Herald, C.L.; Kamano, Y.; Pettit, G.R.; Blumberg, P.M., “Modeling of the Bryostatins to the Phorbol Ester Pharmacophore on Protein Kinase C”,Proc. Natl. Acad. Sci., USA, vol. 85: pp. 7197-7201 (1988).
Wender, P.A.; Irie, K.; Miller, B., “Identification, Activity, and Structural Studies of Peptides Incorporating the Phorbol Ester-Binding Domain of Protein Kinase C”,Proc. Natl. Acad. Sci., USA, vol. 92: pp. 239-243 (1995).
Wender, P.A.; Brabander, J.D.; Harran, P.G.; Jimenez, J-M.; Koehler, M.F.T.; Lippa, B.; Park, C.-M.; Shiozaki, M., “Synthesis of the First Members of a New Class of Biologically Active Bryostatin Analogues”, J. Am. Chem. Soc., vol. 120: pp. 4534-4535 (1998).
Wender, P.A.; DeBrabander, J.; Harran, P.G.; Jimenez, J.-M.; Koehler, M.F.T.; Lippa, B.; Park, C.-M.; Siedenbiedel, C.; Pettit, G.R., “The Design, Computer Modeling, Solution Structure, and Biological Evaluation of Synthetic Analogues of Bryostatin 1”,Proc. Natl. Acad. Sci., USA, vol. 95: pp. 6624-6629 (1998).
Wender, P.A.; DeBrabander, J.; Harran, P.G.; Hinkle, K.W.; Lippa, B.; Pettit, G.R., “Synthesis and Biological Evaluation of Fully Synthetic Bryostatin Analogues”,Tetrahedron Letters, vol. 39: pp. 8625-8628 (1998).
Wender, P.A.; Lippa, B., “Synthesis and Biological Evaluation of Bryostatin Analogues: The Role of the A-Ring”,Tetrahedron Letters, vol. 41: pp. 1007-1011 (2000).
Wender, P.A.; Baryza, J.L.; Bennett, C.E.; Bi, F.C.; Brenner, S.E.; Clarke, M.O.; Horan, J.C.; Kan, C.; Lacote, E.; Lippa, B.; Nell, P.G.; Turner, T.M., “The Practical Synthesis of a Novel and Highly Potent Analogue of Bryostatin”,J. Am. Chem. Soc., vol. 124: pp. 13648-13649 (2002).
Wender, P.A.; Maywey, A.V.W.; VanDeusen, C.L., “A Concise, Selective Synthesis of the Polyketide Spacer Domain of a Potent Bryostatin Analogue”,Organic Letters, vol. 5: pp. 277-279 (2003).
Wender, P.A.; Koehler, M.F.T.; Sendzik, M., “A New Synthetic Approach to the C Ring of Known as Well as Novel Bryostatin Analogues”,Organic Letters, vol. 5: pp. 4549-4552 (2003).

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