Chemistry: natural resins or derivatives; peptides or proteins; – Proteins – i.e. – more than 100 amino acid residues – Chemical modification or the reaction product thereof – e.g.,...
Reexamination Certificate
2003-07-18
2011-10-04
Chu, Yong (Department: 1626)
Chemistry: natural resins or derivatives; peptides or proteins;
Proteins, i.e., more than 100 amino acid residues
Chemical modification or the reaction product thereof, e.g.,...
C536S017400, C536S025310, C548S518000, C548S544000
Reexamination Certificate
active
08030459
ABSTRACT:
The present invention relates to biodegradable biocompatible polyketals, methods for their preparation, and methods for creating animals by administration of biodegradable biocompatible polyketals. In one aspect, a method for forming the biodegradable biocompatible polyketals comprises combining a glycol-specific oxidizing agent with a polysaccharide to form an aldehyde intermediate, which is combined with a reducing agent to form the biodegradable biocompatible polyketal. The resultant biodegradable biocompatible polyketals can be chemically modified to incorporate additional hydrophilic moieties. A method for treating animals includes the administration of the biodegradable biocompatible polyketal in which biologically active compounds or diagnostic labels can be disposed. The present invention also relates to chiral polyketals, methods for their preparation, and methods for use in chromatographic applications, specifically in chiral separations. A method for forming the chiral polyketals comprises combining a glycol-specific oxidizing agent with a polysaccharide to form an aldehyde intermediate, which is combined with a suitable reagent to form the chiral polyketal. A method for use in chiral separations includes the incorporation of the chiral polyketals in the mobile phase during a chromatographic separation, or into chiral stationary phases such as gels. The present invention further relates to chiral polyketals as a source for chiral compounds, and methods for generating such chiral compounds.
REFERENCES:
patent: 5075222 (1991-12-01), Hannum et al.
patent: 5342770 (1994-08-01), Yamasaki
patent: 5582172 (1996-12-01), Papisov et al.
patent: 5591710 (1997-01-01), Hsia
patent: 5605791 (1997-02-01), Ashkenazi et al.
patent: 5612037 (1997-03-01), Huebner et al.
patent: 5624803 (1997-04-01), Noonberg et al.
patent: 5780243 (1998-07-01), Thacker
patent: 5811510 (1998-09-01), Papisov
patent: 5817343 (1998-10-01), Burke
patent: 5824784 (1998-10-01), Kinstler et al.
patent: 5863990 (1999-01-01), Papisov
patent: 5945293 (1999-08-01), Siiman et al.
patent: 5958398 (1999-09-01), Papisov
patent: 6048837 (2000-04-01), Friedman et al.
patent: 6057431 (2000-05-01), Ishihara et al.
patent: 6294170 (2001-09-01), Boone et al.
patent: 6514500 (2003-02-01), Bridon et al.
patent: 6822086 (2004-11-01), Papisov
patent: 7160924 (2007-01-01), Kinstler et al.
patent: 7270808 (2007-09-01), Cheng et al.
patent: 2002/0082362 (2002-06-01), Brocchini et al.
patent: 2002/0172689 (2002-11-01), Scott
patent: 2004/0105840 (2004-06-01), Kinstler et al.
patent: 2005/0169968 (2005-08-01), Elmaleh et al.
patent: 2006/0019911 (2006-01-01), Papisov
patent: 2006/0069230 (2006-03-01), Papisov
patent: 2007/0190018 (2007-08-01), Papisov
patent: 2008/0019940 (2008-01-01), Papisov
patent: 0280474 (1988-08-01), None
patent: 0325270 (1989-07-01), None
patent: WO 94/02068 (1994-02-01), None
patent: WO-9605309 (1996-02-01), None
patent: WO 96/32419 (1996-10-01), None
patent: WO-9640912 (1996-12-01), None
patent: WO 98/05363 (1998-02-01), None
patent: WO-98/05363 (1998-02-01), None
patent: WO-9930561 (1999-06-01), None
patent: WO-99/64595 (1999-12-01), None
patent: WO-0078355 (2000-12-01), None
patent: WO-0107486 (2001-02-01), None
patent: WO-0110468 (2001-02-01), None
patent: WO 02/067995 (2002-09-01), None
patent: WO 02/087498 (2002-11-01), None
patent: WO-03059988 (2003-07-01), None
Cervigni et al., Angew. Chem. Chem. Int. Engl., (1996), 35(11), pp. 1230-1232.
G. Hermanson, Bioconjugate Techniques, pp. 552-569.
K. Rose, J. Am. Chem. Soc. 1994, 116, 30-33.
G. Hermanson, Bioconjugate Techniques, pp. 552-569, (1996). (provided before).
International Search Report for PCT/US03/022584.
Bieniarz, et al., “Extended Length Heterobifunctional Coupling Agents for Protein Conjugations”,Bioconjugate Chem.; 7: 88-95, 1996.
Boeckler, et al., “Immunogenicity of New Heterobifunctional Cross-linking Reagents used in the Conjugation of Synthetic Peptides to liposomes”,Jour. of Immunological Methods191: 1-10, 1996.
Dubowchik, et al., “Monomethoxytrityl (MMT) as a Versatile Amino Protecting Group for Complex Prodrugs of Anticancer Compounds Sensitive to Strong Acids, Bases and Nucleophiles,”Tetrahedron Letters, 38(30): 5257-5260, 1997.
Herrmann, et al., “Peptide-functionalized Polyphenylene Dendrimers,”Tetrahedron, 59: 3925-3935, 2003.
Holtsberg, et al., “Poly(ethylene glycol) (PEG) conjugated arginine deiminase: effects of PEG formulations on its pharmacological properties,”Journal of Controlled Release, 80: 259-271, 2002.
Liu et al., “Strategies for the synthesis of fluorescently labeled PNA,”Tetrahedron Letters, 41: 6153-6156, 2000.
Pierce, “NHS-Esters-Maleimide Crosslinkers,” www.piercenet.com/files/0438sm4.pdf, 2002.
Sharma, et al., “Maleimide-Assisted On-resin Macrocyclization,”Tetrahedron Letters, 37(32): 5665-5668, 1996.
U.S. Appl. No. 12/620,855, Papisov et al.
Bendele et al., Short Communication: Renal Tubular Vacuolation in Animals Treated with Polyethylene-Glycol-Conjugated Proteins, Toxicological Sciences, 42: 152-157 (1997).
Bruneel D. et al. “Chemical modification of pullulan: 3. Succinoylation” Polymer, Elsevier Science Publishers B.V, GB, vol. 35, No. 12, Jun. 1, 1994, pp. 2656-2658.
Cervigni S. et al. “Synthesis of Glycopeptides and Lipopeptides by Chemoselective Ligation” Angew. Chem. Int. Ed. Egl. 1996, 35, No. 11, pp. 1230-1232.
Conover, C. et al. Physiological Effect of Polyethylene Glycol Conjugation on Stroma-Free Bovine Hemoglobin in the Conscious Dog After Partial Exchange Transfusion, Artificial Organs, vol. 21, No. 5, 1997, pp. 369-378.
Duncan, R. Polymer-Drug Conjugates. In: Handbook of Anticancer Drug Development, D. Budman, H. Calvert, and E. Rowinsky (Eds.), Lippincott, Williams & Wilkins Philadelphia (2003) pp. 239-260.
Endo et al. Nature of Linkage and Mode of Action of Methotrexate Conjugated with Antitumor Antibodies: Implications for Future Preparation of Conjugates. Cancer Research 48, 3330-3335, Jun. 15, 1988.
Feng et al. Synthesis and Evaluation of Water-Soluble Paclitaxel Prodrugs. Bioorganic & Medicinal Chemistry Letters 12 (2002) 3301-3303.
Gao Q. et al. “Drug-induced DNA repair: X-ray structure of a DNA-ditercalinium complex” Proc. Natl. Acad. Sci. USA vol. 88, pp. 2422-2426, Mar. 1991.
Hermanson G. Bioconjugate Techniques pp. 548-569 (1996).
Jordan, Craig V. Tamoxifen: A Most Unlikely Pioneering Medicine. Nature Reviews. vol. 2, Mar. 2003, 205-213.
Matysiak S. “Acetal Oligonucleotide Conjugates in Antisense Strategy” Nucleosides & Nucleotides, 16(5&6), pp. 855-861 (1997).
Papisov M.I. et al. “Semisynthetic Hydrophilic Polyals” Biomacromolecules 2005, vol. 6, pp. 2659-2670.
Pierce, NHS-Esters-Maleimide Crosslinkers, Jun. 27, 2002, pp. 1-8.
Tomlinson et al. Polyacetal-Doxorubicin Conjugates Designed for pH-Dependent Degradation. Bioconjugate Chem. 2003, 14, 1096-1106.
Zalipsky et al. Attachment of Drugs to Polyethylene Glycols. Eur. Polym. J. vol. 19, No. 12, pp. 1177-1183, 1983.
Conover, C. et al. Physiological Effect of Polyethylene Glycol Conjugation on Stroma-Free Bovine Hemoglobin in the Conscious Dog After Partial Exchange Transfusion, Artificial Organs, vol. 21, No. 5, 1997, pp. 369-378.
Endo et al. Nature of Linkage and Mode of Action of Methotrexate Conjugated with Antitumor Antibodies: Implications for Future Preparation of Conjugates. Cancer Research. (1988), 48, p. 3330-3335.
Feng et al. Bioorg. Med. Chem. Lett. (2002) 12, pp. 3301-3303.
Gao Q. et al. Drug-induced DNA repair: X-ray structure of a DNA-ditercalinium complex Proc. Natl. Acad. Sci. USA vol. 88, pp. 2422-2426, Mar. 1991 Biochemistry.
Jordan, V. C. Nature Reviews: Drug Discovery, Feb. 2003, p. 205-213.
Maeda, H et al. Conjugates of anticancer agents and polymers: advantages of macromolecular therapeutics in vivo. Bioconj. Chem. 1992, 3:351-362.
Matysiak S. Acetal Oligonucleotide Conjugates in Antisense Strategy Nucleosides &#x
Papisov Mikhail I.
Yurkovetskiy Alexander
Choate Hall & Stewart LLP
Chu Yong
Herschbach Jarrell Brenda
Rearick John P.
The General Hospital Corporation
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