Dehydrophenylahistins and analogs thereof and the synthesis...

Details Dehydrophenylahistins and analogs thereof and the synthesis... Dehydrophenylahistins and analogs thereof and the synthesis...

2011-05-03

2011-05-03

Wilson, James O (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C514S253090, C514S254050

Reexamination Certificate

active

07935704

ABSTRACT:
Compounds represented by the following structure (I) are disclosed:as are methods for making such compounds, wherein said methods comprise reacting a diacyldiketopiperazine with a first aldehyde to produce an intermediate compound; and reacting the intermediate compound with a second aldehyde to produce the class of compounds with the generic structure, where the first aldehyde and the second aldehydes are selected from the group consisting of an oxazolecarboxaldeyhyde, imidazolecarboxaldehyde, a benzaldehyde, imidazolecarboxaldehyde derivatives, and benzaldehyde derivatives, thereby forming the above compound wherein R1, R1′, R1″, R2, R3, R4, R5, and R6, X1and X2, Y, Z, Z1, Z2, Z3, and Z4may each be separately defined in a manner consistent with the accompanying description. Compositions and methods for treating vascular proliferation are also disclosed.

REFERENCES:
patent: 5607934 (1997-03-01), Tone et al.
patent: 5733888 (1998-03-01), Carver et al.
patent: 5852018 (1998-12-01), Bryans et al.
patent: 5874443 (1999-02-01), Kiely et al.
patent: 5886210 (1999-03-01), Rayle et al.
patent: 5891877 (1999-04-01), Brocchini et al.
patent: 5922683 (1999-07-01), Or et al.
patent: 6069146 (2000-05-01), Fenical et al.
patent: 6350759 (2002-02-01), Casara et al.
patent: 6358957 (2002-03-01), Fukumoto et al.
patent: 6500825 (2002-12-01), Lan et al.
patent: 6506787 (2003-01-01), Fujishita et al.
patent: 6509331 (2003-01-01), Audia et al.
patent: 6583143 (2003-06-01), Haddach
patent: 6713480 (2004-03-01), Fukumoto et al.
patent: 6972289 (2005-12-01), Kanzaki et al.
patent: 7026322 (2006-04-01), Hayashi et al.
patent: 7064201 (2006-06-01), Hayashi et al.
patent: 7674903 (2010-03-01), Hayashi et al.
patent: 2002/0028819 (2002-03-01), Teng et al.
patent: 2002/0143021 (2002-10-01), Fukumoto et al.
patent: 2004/0102454 (2004-05-01), Hayashi et al.
patent: 2005/0090667 (2005-04-01), Hayashi et al.
patent: 2005/0197344 (2005-09-01), Palladino et al.
patent: 2006/0079953 (2006-04-01), Kanzaki et al.
patent: 2006/0167010 (2006-07-01), Hayashi et al.
patent: 2006/0217553 (2006-09-01), Hayashi et al.
patent: 2006/0223822 (2006-10-01), Hayashi et al.
patent: 2006/0223823 (2006-10-01), Hayashi et al.
patent: 2007/0078138 (2007-04-01), Palladino et al.
patent: 2008/0221122 (2008-09-01), Palladino et al.
patent: 2403790 (2001-07-01), None
patent: 0655060 (1998-01-01), None
patent: 1 264 831 (2002-11-01), None
patent: 2143823 (1985-02-01), None
patent: 5009164 (1993-01-01), None
patent: 10-130266 (1998-05-01), None
patent: WO 95/21832 (1995-08-01), None
patent: WO 96/20190 (1996-07-01), None
patent: WO 99/38844 (1999-08-01), None
patent: WO 99/48889 (1999-09-01), None
patent: WO 01/53290 (2001-07-01), None
patent: WO2004054498 (2004-01-01), None
patent: WO 2004/054498 (2004-07-01), None
patent: WO 2005/077940 (2005-08-01), None
Dorwald F. A. Side Reactions in Organic Synthesis, 2005, Wiley: VCH, Weinheim p. IX of Preface.
Cecil Textbook of Medicine, 21st Edition (2000), Goldman & Bennett (Editors), W.B. Saunders Company (Publisher), Chapter 198, pp. 1060-1074.
Internal Medicine, 4th Edition, Editor-in-Chief Jay Stein, Chapters 71-72, pp. 699-715.
http://scienceandresearch.homeoffice.gov.uk/animal-research/publications-and-reference/001-abstracts/abstracts2-2006/02november-2006/457?view=Html; “Abstract #457, Animals in Scientific Procedures (2006).” (accessed on Nov. 19, 2008.).
Mahindroo, et. al., Expert Opin. Ther. Patents (2006) 16(5), 647-691.
Abstracts of The 1999 Joint Chubu and Kansai Branch Conference and Symposium of Japan Society for Bioscience, Biotechnology, and Agrochemistry, p. 48 (1999) (in Japanese).
Abstracts of The 1999 Joint Chubu and Kansai Branch Conference and Symposium of Japan Society for Bioscience, Biotechnology, and Agrochemistry, p. 48 (1999) (translated to English).
Akerlund et al., “Diketopiperazine-Based Polymers from Common Amino Acids,” Journal of Applied Polymer Science (2000), 78 (12), 2213-2218.
Amendment and Response to Written Opinion submitted in International Application No. PCT/US03/024232 on Jan. 20, 2005.
Augustin, M. “Die Umsetzung des 2,5-Diketopiperazins mit Aldehyden und Nitrosoverbindungen” Journal für Praktische Chemie, vol. 32(4) pp. 158-166 (1966).
European Supplementary Search Report dated Oct. 11, 2005 for Application No. 00963011.2-2117 PCT/JP0006807.
Fukushima et al., “Biological Activities of Albonoursin,” J. Antibiotics, 26: 175 (1973).
Goldfarb et al., “Synthesis of β-2-thienylalanine” Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, pp. 98-100 (1958), as abstracted by CAPLUS.
Hayashi, et al., “Total Synthesis of Anti-microtubule Diketopiperazine Derivatives: Phenylahistin and Aurantiamine,”J. Org. Chem. 2000, 65: 8402-8405.
Hyun, et al., “Valine dehydrogenase fromStreptomyces albus: gene cloning, heterologous expression and identification of active site by site-directed mutagenesis,”FEMS Microbiology Letters182 (2000) 29-34.
International Search Report, International Application No. PCT/US03/24232, Sep. 27, 2004.
Kanoh et al., “(−)-Phenylahistin: A New Mammalian Cell Cycle Inhibitor Produced by Aspergillus USTUS,” Bioorganic & Medicinal Chemistry Letters, 7: 2847-2852 (1997).
Kanoh et al., “Synthesis and Biological Activities of Phenylahistin Derivatives,” Bioorganic & Medicinal Chemistry, 7: 1451-1457 (1999).
Kanoh et al., “Antitumor Activity of Phenylahistin in Vitro and in Vivo,” Bioscience Biotechnology Biochemistry, 63: 1130-1133 (1999).
Kanoh et al., “(−)-Phenylahistin Arrests Cells in Mitosis by Inhibiting Tubulin Polymerization”,The Journal of Antibiotics, 52: 134-141 (1999).
Kanzaki et al., A Novel Potent Cell Cycle Inhibitor Dehydrophenylahistin-Enzymatic Synthesis and Inhibitory Activity toward Sea Urchin Embryo,The Journal of Antibiotics, 55: 1042-1047 (Dec. 2002).
Kanzaki et al., “Effective Production of Dehydro Cyclic Dipeptide Albonoursin Exhibiting Pronuclear Fusion Inhibitory Activity, I. Taxonomy and Fermentation”The Journal of Antibiotics, 52: 1017-1022 (1999).
Kanzaki et al., “Effective Production of Dehydro Cyclic Dipeptide Albonoursin Exhibiting Pronuclear Fusion Inhibitory Activity, II. Biosynthetic and Bioconversion Studies”The Journal of Antibiotics, 53: 58-62 (2000).
Kanzaki, et al., “Novel Cyclic Dipeptide Dehydrogenase and Assay Method for Its Activity,” Scientific Reports of the Faculty of Agriculture, Okayama University, 88:7-11 (1999). (in Japanese).
Kanzaki, et al., “Novel Cyclic Dipeptide Dehydrogenase and Assay Method for Its Activity,” Scientific Reports of the Faculty of Agriculture, Okayama University, 88:7-11 (1999). (translated into English).
Kanzaki et al., “Enzymatic Synthesis of Physiologicall Actve Substances Utilizing a Novel System for the Synthesis of Diketopiperazines Comprising Dehydroamino Acids as Constituents”Abstracts of Papers Presented at the 1999 Meeting of the Society for ActinomycetesJapan, p. 42 (1999).
Kanzaki et al., “Enzymatic dehydrogenation of cyclo(L-Phe-L-Leu) to a bioactive derivative, albonoursin,”Journal of Molecular Catalysis B: Enzymatic6 (1999) 265-270.
Kobayashi et al., “Microtubule Assembly Regulators of Microbial Origin”Abstract of Paper Read at the 1989 Symposium on the Chemistry of Natural Products, p. 51 (1989).
Kopple et al., “A Convenient Synthesis of 2,5-Piperazinediones1a,”The Journal of Organic Chemistry, 33: 862-864 (1967).
Küster and Köppenhofer, “Über eininge Pyrrolderivate” Z. Physiol, Chem., vol. 172, pp. 126-137 (1927).
Lastly, Asahina, T. Bulletin of the Chemical Society of Japan, vol. 5, pp. 354-365 (1930).
Niemann et al, “The Synthesis of the Three Isomeric dl-β-Pyridylalanines” Journal of the American Chemical Society, vol. 64(7), pp. 1678-1682 (1942).
Nitecki et al., “A Simple Route to

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