Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2005-03-22
2005-03-22
Aulakh, Charanjit S. (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C549S416000, C549S294000, C549S293000, C549S273000, C568S579000, C568S626000
Reexamination Certificate
active
06870058
ABSTRACT:
Compounds which mimic the chemical and/or biological activity of discodermolide are provided and intermediates useful in their preparation.
REFERENCES:
patent: 5010099 (1991-04-01), Gunasekera et al.
patent: 5681847 (1997-10-01), Longley et al.
patent: 5789605 (1998-08-01), Smith, III et al.
patent: 6242616 (2001-06-01), Smith et al.
patent: 6495594 (2002-12-01), Gunasekera et al.
patent: 2280677 (1995-02-01), None
Clark, D.L. et al., “Studies on the Alkylation of Chiral Enolates: Application toward the Total Synthesis of Discodermolide”,J. Org. Chem., 1993, 58, 5878-5879.
Evans, P.L. et al., “The Synthesis of a C9-C17Lactone Fragment of Discodermolide”,Tetra. Lett., 1993, 34(50), 8163-8166.
Golec, J.M.C. et al., “The Synthesis of a C1-C8Lactone Fragment of Discodermolide”,Tetra. Lett., 1993, 34(50), 8159-8162.
Golec, J.M.C. et al., “An Approach to the Synthesis of a C9-C15Fragment of Discodermolide”,Tetra. Lett., 34(50), 8167-8168.
Golec, J.M.C. et al., “Total synthesis of discodermolide”,Chemical Abstracts, 1995, 123, 831, Abstract No. 32864j.
Greene and Wuts, Protective Groups in Organic Synthesis, 2d Edition, John Wiley & Sons, New York, 1991.
Gunasekera et al., “Discodermolide: A New Bioactive Polyhydroxylated Lactone from the Marine SpongeDiscodermia dissoluta”,J. Org. Chem., 1990, 55, 4912-4915.
Gunasekera et al., “Discodermolide: A New Bioactive Polyhydroxylated Lactone from the Marine SpongeDiscodermia dissoluta: Additions and Corrections”,J. Org. Chem., 1991, 56(3), 1346.
Hodges et al., “Reactions to Lithiooxazole”,J. Org. Chem., 1991, 56, 449-452.
Hung et al., “Distinct binding and cellular properties of synthetic (+)- and (−)-discodermolides”,Chem.&Biol., 1994, 1(1), 67-71.
Hung et al., “(+)-Discodermolide binds to microtubules in stoichiometric ratio to tubulin dimers, blocks taxol binding and results in mitotic arrest”,Chem.&Biol., 1996, 3(4), 287-293.
Hung, D.T. et al., “Syntheses of Discodermolides Useful for Investigating Microtubule Binding and Stabilization”,J. Am. Chem. Soc., 1996, 118, 11054-11080.
Jacquesy et al., “Metabromation Du Dimethyl-2,6 Phenol Et De Son Ether Methylique En Milieu Superacide”,Tetrahedron, 1981, 37, 747-751.
Kim et al., “Conversion of Acetals into Monothioacetals, α-Alkoxyazides and α-Alkoxyalkyl Thioacetates with Magnesium Bromide”,Tetra. lett., 1989, 30(48), 6697-6700.
Longley et al., “Discodermolide—A New, Marine-Derived Immunosuppressive Compound”,Transplantation, 1991, 52(4), 650-656.
Longley et al.,“Discodermolide—A New, Marine-Derived Immunosuppressive Compound”,Transplantation, 1991, 52(4), 657-661.
Longley et al., “Immunosuppression by Discodermolide”,Ann. N.Y. Acad. Sci., 1993, 696, 94-107.
Nerenberg et al., “Total Synthesis of the Immunosuppressive Agent (=)-Discodermolide”,J. Am. Chem. Soc., 1993, 115, 12621-12622.
Paterson, I. et al., “Studies Towards the Total Synthesis of the Marine-derived Immunosuppressant Discodermolide; Asymmetric Synthesis of a C1-C8δ-lactone Subunit”,J. Chem. Soc. Chem. Commun., 1993, 1790-1792.
Paterson, I. et al., “Studies Towards the Total Synthesis of the Marine-derived Immunosuppressant Discodermolide; Asymmetric Synthesis of a C9-C24Subunit”,Synlett, 1995, 498-500.
Remington's Pharmaceutical Sciences, Mack Publishing Company, Easton, PA, 1980.
Roush et al., “Acyclic Diastereoselective Synthesis Using Tartrate Ester Modified Crotylboronates. Double Asymmetric Reactions with α-Methyl Chiral Aldehydes and Synthesis of the C(19)-C(29) Segment of Rifamycin S”,J. Am. Chem. Soc., 1990, 112, 6348-6359.
Smith et al., “Total Synthesis of (−)-Discodermolide”,J. Am. Chem. Soc., 1995, 117, 12011-12012.
Smith, A. B. et al., “Total Synthesis of (−)-Discodermolide Exploiting a Common Precursor”,J. Am. Chem. Soc., (Submission Copy), 1-60.
Solladie et al., “Asymmetric Synthesis of Polyhydroxylated Natural Products II. The C-1/C-12 Unit of Amphotericin B”,Tetra. Lett., 1987, 28(7), 797-800.
ter Haar et al., “Discodermolide, A Cytotoxic Marine Agent that Stabilizes Microtubules More Potently than Taxol”,Biochem., 1996, 35, 243-250.
Yang, G. et al., “The Synthsis of the C-9 to C-21 Sector of Discodermolide: An Efficient Route to the C12-14 Z-Trisubstituted Alkene”,Tetra. Lett., 1994, 35(16), 2503-2504.
Yang, G. et al., “An Alkylative Strategy to the C-13 to C-21 Sector of Discodermolide”,Tetra. Lett., 1994, 35(9), 1313-1316.
Evans, D.A. et al., “Enantioselective Synthesis of Altohyrtin C (Spongistatin 2): Synthesis of the AB- and CD-Spiroketal Subunits”,Angew. Chem. Int. Ed. Engl., 1997, 36(24), 2738-2740.
Evans, D.A. et al., “Enantioselective Synthesis of Altohyrtin C (Spongistatin 2): Synthesis of the EF-Bis(pryan) Subunit”,Angew. Chem. Int. Ed. Engl., 1997, 36(24), 2741-2743.
Evans, D.A. et al., “Enantioselective Synthesis of Altohyrtin C (Spongistatin 2): Fragment Assembly and Revision of the Spongistatin 2 Stereochemical Assignment”,Angew. Chem. Int. Ed. Engl., 1997, 36(24), 2744-2747.
Guo, J. et al., “Total Synthesis of Altohyrtin A (Spongistatin 1): Part 1”,Angew. Chem. Int. Ed. Engl., 1998, 37(1/2), 157-191.
Hayward, M.M. et al., “Total Synthesis of Altohyrtin A (Spongistatin 1): Part 2”,Angew. Chem. Int. Ed. Engl., 1998, 37(1/2), 192-196.
Paterson, I. et al., “Studies in Marine Macrolide Synthesis: Synthesis of the C1-C15Subunit of Spongistatin 1 (Altohyrtin A) and 15,16-Anti Aldol Coupling Reactions”,Tetra. Lett., 1997, 38(47), 8241-8244.
Paterson, I. et al., “Studies in Marine Macrolide Synthesis: Synthesis: Synthesis of a C16-C28Subunit of Spongistatin 1 (Altohyrtin A) Incorporating the CD-Spiroacetal Moiety”,Tetra. Lett., 1997, 38(51), 8911-8914.
Balachandran, R. et al., “The potent microtubule-stabilizing agent (+)-discodermolide induces apoptosis in human breast carcinoma cells—preliminary comparisons to paclitaxel”,Anti-Cancer Drugs, 1998, 9, 67-76.
Gunasekera et al., “Discodermolide: A New Bioactive Polyhydroxylated Lactone from the Marine SpongeDiscodermia dissoluta”,J. Org. Chem., 1991, 56(3), 1346 (Additions and Corrections to p. 4912 of article found inJ. Org. Chem., 1990, 55, 4912-4915.
Harried, S.S. et al., “Total Synthesis of (−)-Discodermolide: An Application of a Chelation-COntrolled Alkylation Reaction”,J. Org. Chem., 1997, 62, 6098-6099.
Kowalski, R.J. et al., “The Microtubule-Stabilizing Agent Discodermolide Competitively Inhibits the Binding of Paclitaxel (Taxol) to Tubulin Polymers, Enhances Tubulin Nucleation Reactions More Potently than Paclitaxel, and Inhibits the Growth of Paclitaxel-Resistant Cells”,Mol. Pharmacology, 1997, 52, 613-622.
Marshall, J.A. et al., “Synthesis of Discodermolide Subunites by SE2' Addition of Nonracemic Allenylstannanes to Aldehydes”,J. Org. Chem., 1998, 63, 817-823.
Miyazawa, M. et al., “Stereoselective of the C1-C7Segment of (+)-Discodermolide”,Chem. Letts., 1997, 1191-1192.
Miyazawa, M. et al., “Synthesis of the C8-C15Segment of (+)-Discodermolide”,Chem. Letts., 1997, 1193-1194.
Smith, III et al., “Synthesis and in Vitro Cancer Cell Growth Inhibitory Activity of Monocyclic Model Compounds Containing Spongistatin Triene Side-Chains”,Bioorg. Med. Chem. Letts., 1998, 8, 567-568.
Walkup, R.D. et al., “Expeditious Synthesis of a Key C9-C21Subunit of the Aplysiatoxins and Oscillatoxins”,Tetra. Lett., 1990, 31(52), 7587-7590.
Beauchamp Thomas J.
LaMarche Matthew J.
Smith, III Amos B.
Aulakh Charanjit S.
The Trustees of the University of Pennsylvania
Woodcock & Washburn LLP
LandOfFree
Compounds which mimic the chemical and biological properties... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Compounds which mimic the chemical and biological properties..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Compounds which mimic the chemical and biological properties... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3429029