Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2011-07-19
2011-07-19
Solola, Taofiq A (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
active
07982060
ABSTRACT:
The present invention provides macrocyclic compounds, synthesis of the same and intermediates thereto. Such compounds, and compositions thereof, are useful for treating or preventing proliferative disorders Formula (F-4).
REFERENCES:
patent: 5338865 (1994-08-01), Kishi et al.
patent: 5436238 (1995-07-01), Kishi et al.
patent: 6214865 (2001-04-01), Littlefield et al.
patent: 6365759 (2002-04-01), Littlefield et al.
patent: 6469182 (2002-10-01), Littlefield et al.
patent: 6653341 (2003-11-01), Littlefield et al.
patent: 7470720 (2008-12-01), Littlefield et al.
patent: 2007/0244187 (2007-10-01), Austad et al.
patent: 2009/0198074 (2009-08-01), Chase et al.
patent: 2009/0203771 (2009-08-01), Inanaga et al.
patent: 0 572 109 (1993-12-01), None
patent: 0572109 (1993-12-01), None
patent: WO 93/17690 (1993-09-01), None
patent: WO 99/65894 (1999-12-01), None
patent: WO 2005/118565 (2005-12-01), None
patent: WO 2005/118565 (2005-12-01), None
patent: WO 2009/046308 (2009-04-01), None
patent: WO 2009/046308 (2009-04-01), None
patent: WO 2009/064029 (2009-05-01), None
patent: WO 2009/064029 (2009-05-01), None
patent: WO 2009/124237 (2009-10-01), None
Choi et al., “Synthetic Studies on the Marine Natural Product Halichondrins,” Pure Appl. Chem. 75:1-17, 2003.
Hirata et al., “Halichondrins—Antitumor Polyether Macrolides from a Marine Sponge,” Pure Appl. Chem. 58:701-710, 1986.
Horita et al., “Synthetic Studies of Halichondrin B, an Antitumor Polyether Macrolide Isolated from a Marine Sponge. 8. Synthesis of the Lactone Part (C1-C36) via Horner-Emmons Coupling Between C1-C15 and C16-C36 Fragments and Yamaguchi Lactonization,” Tetrahedron Lett. 38:8965-8968, 1997.
International Preliminary Report on Patentability from International Application No. PCT/US2005/019669, issued Dec. 4, 2006.
International Search Report from International Application No. PCT/US2005/019669 dated Aug. 29, 2005 (date of completion of search) and Sep. 7, 2005 (date of mailing of report).
Written Opinion from International Application No. PCT/US2005/019669, mailed Sep. 7, 2005.
Aicher et al., “Total Synthesis of Halichondrin B and Norhalichondrin B,”J. Am. Chem. Soc. 114(8): 3162-3164 (1992).
Aicher, T.D., et al., “Synthetic Studies Towards Halichondrins: Synthesis of the C.27-C.38 Segment,”Tetrahedron Lett. 33(12): 1549-1552 (1992).
Anderson, “Developing Processes for Crystallization-Induced Asymmetric Transformation,”Org. Process. Res. Dev. 9: 800-813 (2005).
Bai et al., “Halichondrin B and Homohalichondrin B, Marine Natural Products Binding in the Vinca Domain of Tubulin. Discovery of Tubulin-based Mechanism of Action by Analysis of Differential Cytotoxicity Data,”J. Biol. Chem. 266(24): 15882-15889 (1991).
Bernet et al., “Carbocyclische Verbindungen aus Monosacchariden. Umsetzungen in der Glucosereihe,”Helv. Chim. Acta. 62: 1990-2016 (1979).
Blanchette et al., “Horner-Wadsworth-Emmons Reaction: Use of Lithium Chloride and an Amine for Base-Sensitive Compounds,”Tetrahedron Lett. 25(21): 2183-2186 (1984).
Burke, S.D., et al., “Enantioselective Synthesis of a Halichondrin B C(20)→C(36) Precursor,”Tetrahedron Lett., 36(39): 7023-7026 (1995).
Burke, S.D., et al., “Synthesis of a C(22)→C(34) Halichondrin Precursor via a Double Dioxanone-to-Dihydropyran Rearrangement,”Tetrahedron Lett., 32(32): 3961-3964 (1991).
Burke, S.D., et al., “Synthesis of a C(22)-C(34) Halichondrin B Precursor via Ring Opening—Double Ring Closing Metathesis,”J. Org. Chem., 63: 8626-8627 (1998).
Burke, S.D., et al., “Synthetic Studies Toward Complex Polyether Macrolides of Marine Origin,”Spec. Publ. R. Soc. Chem., 198: (Anti-Infectives), 73-85 (1997).
Chen C., et al., “Ni(II)/Cr(II)-Mediated Coupling Reaction: An Asymmetric Process,”J. Org. Chem., 60: 5386-5387 (1995).
Choi et al., “Assymmetric Ni(II)/Cr(II)-Mediated Coupling Reaction: Catalytic Process,”Org. Lett. 4(25): 4435-4438 (2002).
Choi et al., “Synthetic Studies on the Marine Natural Product Halichondrins,”Pure Appl. Chem. 75(1): 1-17 (2003).
Cooper, A.J., et al., “Total Synthesis of Halichondrin B from Common Sugars: An F-Ring Intermediate from D-Glucose and Efficient Construction of the C1 to C21 Segment,”Tetrahedron Lett., 34(51): 8193-8196 (1993).
Dong, C. et al. “New Syntheses of E7389 C14-C35 and Halichondrin C14-C38 Building Blocks: Reductive Cyclization and Oxy-Michael Cyclization Approaches” J. Am. Chem. Soc. 131: 15642-15646 (2009).
Flemming et al., “Nitrile Anion Cyclizations,”Tetrahedron58:1-23 (2002).
Hirata et al., “Halichondrins—Antitumor Polyether Macrolides from a Marine Sponge,”Pure Appl. Chem. 58(5): 701-710 (1986).
Hori et al., “Efficient Synthesis of 2,3-trans-Tetrahydropyrans and Oxepanes: Rearrangement-Ring Expansion of Cyclic Ethers Having a Chloromethanesulfonate,”Tetrahedron Lett. 40: 2145-2148 (1999).
Horita et al., “Synthetic Studies of Halichondrin B, an Antitumor Polyether Macrolide Isolated from a Marine Sponge. 8. Synthesis of the Lactone Part (C1-C36) via Horner-Emmons Coupling Between C1-C15 and C16-C36 Fragments and Yamaguchi Lactonization,”Tetrahedron Lett. 38(52): 8965-8968 (1997).
Horita, K., et al., “Synthetic Studies of Halichondrin B, an Antitumor Polyether Macrolide Isolated From a Marine Sponge. 2. Efficient Synthesis of C16-C26 Fragments via Construction of the D Ring by a Highly Stereocontrolled lodoetherification,”Synlett, 40-43 (1994).
Horita, K., et al., “Synthetic Studies of Halichondrin B, an Antitumor Polyether Macrolide Isolated from a Marine Sponge. 3. Synthesis of C27-C36 Subunit via Completely Stereoselective C-Glycosylation to the F ring,”Synlett, 43-45 (1994).
Horita, K., et al., “Research on Anti-Tumor Active Site of Marine Source Natural Product, Halichondrin B.,”International Congress Series, 1157 (Towards Natural Medicine Research in the 21stCentury), 327-336 (1998).
Horita, K., et al., “Synthetic Studies of Halichondrin B, an Antitumor Polyether Macrolide Isolated from a Marine Sponge. 7. Synthesis of Two C27-C36 Units via Construction of the F ring and Completely Stereoselective C-Glycosylation Using Mixed Lewis Acids,”Chem. Pharm. Bull., 45(10): 1558-1572 (1997).
Horita, K., et al., “Synthetic Studies on Halichondrin B, an Antitumor Polyether Macrolide Isolated from a Marine Sponge. 9. Synthesis of the C16-C36 unit via Stereoselective Construction of the D and E Rings,”Chem. Pharm. Bull., 46(8): 1199-1216 (1998).
Horita, K., et al., “Synthetic Study of a Highly Antitumorigenic Marine Phytochemical, Halichondrin B,”Phytochemicals and Phytopharmaceuticals, Shahihi, F. and Ho, C.-T., Eds., AOCS Press, Champaign, IL, 2000, 386-397.
Jackson et al., “A Total Synthesis of Norhalichondrin B”Angew. Chem. Int. Ed. 48: 2346-2350 (2009).
Jackson et al., “The Halichondrins and E7389,”Chem. Rev. 109: 3044-3079 (2009).
Jiang, L., et al., “A Novel Route to the F-Ring of Halichondrin B. Diastereoselection in Pd(0)-Mediatedmesoand C2Diol Desymmetrization,”Org. Lett., 4(20): 3411-3414 (2002).
Jiang, L., et al., “A Practical Synthesis of the F-Ring of Halichondrin B via Ozonolytic Desymmetrization of a C2-Symmetric Dihydroxycyclohexene,”J. Org. Chem., 68: 1150-1153 (2003).
Kim, D. et al. “New Syntheses of E7389 C14-C35 and Halichondrin C14-C38 Building Blocks: Double-Inversion Approach”J. Am. Chem. Soc. 131: 15636-15641 (2009).
Kurosu et al., “Fe/Cr- and Co/Cr-Mediated Catalytic Asymmetric 2-Haloallylations of Aldehydes,”J. Am. Chem. Soc. 126: 12248-12249 (2004).
Mattocks, “Novel Reactions of Some α-Acyloxy Acid Chlorides,”J. Chem. Soc. 371: 1918-1930 (1964).
Mattocks, “Novel Reactions of Some α-Acyloxy-acid Halid
Austad Brian
Chase Charles E.
Fang Francis G.
Clark & Elbing LLP
EISAI R&D Management Co., Ltd.
Solola Taofiq A
LandOfFree
Intermediates for the preparation of analogs of Halichondrin B does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Intermediates for the preparation of analogs of Halichondrin B, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Intermediates for the preparation of analogs of Halichondrin B will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2726368