Didemnin analogs and fragments and methods of making and...

Details Didemnin analogs and fragments and methods of making and... Didemnin analogs and fragments and methods of making and...

2006-10-17

2006-10-17

Weber, Jon (Department: 1654)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Peptide containing doai

C514S011400, C530S317000, C530S322000, C530S323000, C530S324000, C530S402000

Reexamination Certificate

active

07122519

ABSTRACT:
The present invention relates to macrocyclic depsipeptides, including didemnin analogs and fragments thereof, which are useful as anti-cancer agents and for other purposes. The invention includes numerous didemnin analogs and fragments and methods of making them. Methods of using these compounds as inhibitors of protein synthesis, cell growth, and tumorigenesis and as enhancers of apoptosis are also provided.

REFERENCES:
patent: 4160452 (1979-07-01), Theeuwes
patent: 4256108 (1981-03-01), Theeuwes
patent: 4265874 (1981-05-01), Bonsen et al.
patent: 4493796 (1985-01-01), Rinehart, Jr.
patent: 4782135 (1988-11-01), Rinehart, Jr.
patent: 5137870 (1992-08-01), Rinehart
patent: 5504189 (1996-04-01), Emling et al.
patent: 2003/0104991 (2003-06-01), Joullie et al.
patent: WO 98/17275 (1998-04-01), None
patent: WO 98/17302 (1998-04-01), None
patent: WO 02/02596 (2002-01-01), None
Liang et al., J. Am. Chem. Soc., vol. 123, pp. 4469-4474, 2001.
Vervoort et al., J. Org. Chem., vol. 65, pp. 782-792, 2000 (Published on Web Dec. 19 1999).
Abdel-Magid et al., Synlett 537-539 (1990).
Abdel-Magid et al., Tetrahedron Lett. 31:5595-5598 (1990).
Campbell et al., Brit. J. Cancer 77(5):739-744 (1998).
Depenbrock et al., Brit. J. Cancer 78(6)::739-744 (1998).
Ewing et al., Tetrahedron 42:5863-5868 (1986).
Ewing et al., Tetrahedron Lett. 30(29):3757-3760 (1989).
Grubb et al., Biochem. Biophys. Res. Comm. 215:1130-1136 (1995).
Harris et al., Tetrahedron Lett. 28:2837-2840 (1987).
Harris et al., Tetrahedron 44:3489-3500 (1988).
Johnson et al., FEBS Lett. 383:1-5 (1996).
Johnson et al., Immunol. Cell Biol. 77:242-248 (1999).
Johnson et al., J. Cell Biochem. 72:269-278 (1999).
Li et al., J. Am. Chem. Soc. 112:7659-7672 (1990).
Li et al., Studies in Natural Products Chem. 10:241-302 (1992).
Liang et al., Org. Lett. 1:1319-1322 (1999).
Mayer et al., J. Org. Chem. 59:5192-5205 (1994).
Mayer et al., Tetrahedron, Asymmetry 5:519-522 (1994).
Pfizenmayer et al., Bioorg. Med. Chem. Lett. 8:3653-3656 (1998).
Sakai et al., J. Med. Chem. 39:2819-2834 (1996).
Schumacher et al., Tetrahedron, Asymmetry 9:47-53 (1997).
Wipf, Chem. Rev. 95:2115-2134 (1995).
STNEasy/CAplus English language abstract of document FP1, ES2102322A1, Accession No. 1998:169709.
Gemma Jou, et al., “Total Synthesis of Dehydrodidemnin B. Use of Uronium and Phosphonium Salt Coupling Reagents in Peptide Synthesis in Solution, ”J. Org. Chem. 62:354-366 (Am. Chem. Society 1997).
Copy of Communication pursuant to Article 96(2) EPC for European Patent Application No. 01 924 886.3, European Patent Office, Netherlands (Aug. 2004).
Ahuja, D., et al., “Inhibition of Protein Synthesis by Didemnins: Cell Potency and SAR,”J. Med. Chem. 43:4212-4218, American Chemical Society (Nov. 2000).
Ahuja, D., et al., “Inhibition of Protein Synthesis by Didemnin B: How EF-1α Mediates Inhibition of Translocation,”Biochemistry 39:4339-4346, American Chemical Society (Apr. 2000).
Crews, C. M., et al., “Didemnin Binds to the Protein Palmitoyl Thioesterase Responsible for Infantile Neuronal Ceroid Lipofuscinosis,”Proc. Natl. Acad. Sci. USA 93:4316-4319, National Academy of Sciences (1996).
Ding, X., et al., “Structure-Activity Relationships of Side-Chain Modified Didemnins,”Bioorg. Med. Chem. Lett. 11:231-234, Pergamon Press (Jan. 2001).
Joullié, M. M., et al., “Total Synthesis of (−)-Tamandarin B,”Tetrahedron Letters 41:9373-9376 Elsevier Science Ltd. (2000).
Joullié, M.M., et al., “Chemical Defense in Ascidians of theDidemnidaeFamily,”Bioconjugate Chem. 14:30-37, American Chemical Society (Jan.-Feb. 2003).
Liang, B., et al., “Total Synthesis of [(2S)-Hiv2] Didemnin M,”J. Org. Chem. 65:4762-4765, American Chemical Society (Jul. 2000).
Mayer, S., et al., “Synthetic Routes to a Constrained Ring Analog of Didemnin B,”J. Org. Chem. 61:1655-1664, American Chemical Society (1996).
Mayer, S., et al., “The Cyclic Depsipeptide Backbone of the Didemnins,”Acta Cryst. C51:1609-1614, Blackwell Publishing (1995).
Pfizenmayer, A.J., et al., “Synthesis and Biological Activities of [N-MeLeu5] Didemnin B,”Biog. Med. Chem. Lett. 6:2713-2716, Pergamon Press (1996).
Pfizenmayer, A.J., et al., “Synthesis and Biological Activites of [N-MeLeu5]- and [N-MePhe5]- Didemnin B,”Tetrahedron 55:313-334, Pergamon Press (Jan. 1999).
Portonovo, P., et al., “First Total Synthesis of a Fluorescent Didemnin,”Tetrahedron 56:3687-3690, Pergamon Press (Jun. 2000).
Ramanjulu, J.M., et al., “Synthetic Studies of a Didemnin B Analog Based on a 2,3-Diamino Sugar Scaffolding,”Journal of the Chinese Chemical Society 48:1-4, The Chemical Society (Taipei) (2001).
Ramanjulu, J.M., et al., “Syntheses of Acyclic Analogs of Didemnin B,”Synthetic Communications 27:3259-3272, Marcel Dekker, Inc. (1997).
Ramanjulu, J.M., et al., “Synthesis of a Reduced Ring Analog of Didemnin B,”J. Org. Chem. 62:4961-4969, American Chemical Society (1997).
Ramanjulu, J.M., et al., “Analogs of the β-Turn of the Cyclodepsipeptide Didemnin B,”Tetrahedron Letters 37:311-314, Pergamon Press (1996).
Ramanjulu, J.M., et al., “A Facile Synthesis of Benzyl 2-Amino-3-Azido-4-O-p-Methoxybenzyl-6-O-Benzyl-2,3-Dideoxy-α-D-Glucopyranoside: A Key Intermediate in the Formation of a Didemnin B Analog,”J. Carbohydrate Chemistry 15:371-381, Marcel Dekker, Inc. (1996).
Tarver, J.E., et al., “Total Syntheses of Conformationally Constrained Didemnin B Analogues. Replacements ofN, O-Dimethyltyrosine with L-1,2,3-4-Tetrahydroisoquinoline and L-1,2,3,4-Tetrahydro-7-methoxyisoquinoline,”J. Org. Chem. 66:7575-7587, American Chemical Society (Nov. 2001).
Vera, M.D., et al., “Synthesis and Biological Evaluation of Didemnin Photoaffinity Analogues,”Biorg. Med. Chem. Lett. 11:1871-1874, Pergamon Press (Jul. 2001).
Vera, M.D., et al., “Natural Products as Probes of Cell Biology: 20 Years of Didemnin Research,”Medicinal Research Reviews 22:102-145, John Wiley & Sons, Inc. (Mar. 2002).
Vera, M.D., et al., “[Lys3] Didemnins as Potential Affinity Ligands,”Biorg. Med. Chem. Lett.11:13-16, Pergamon Press (Jan. 2001).
Xiao, D., et al., “Total Synthesis of a Conformationally Constrained Didemnin B,”J. Org. Chem. 66:2734-2742, American Chemical Society (Apr. 2001).

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