p -amidobenzylethers in drug delivery agents

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Peptide containing doai

Reexamination Certificate

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C530S330000, C530S331000

Reexamination Certificate

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07553816

ABSTRACT:
Compounds of the formulasin-line-formulae description="In-line Formulae" end="lead"?LAn-Z-X—WwD and BZ-X—WwDin-line-formulae description="In-line Formulae" end="tail"?wherein: D is a drug moiety; L is a ligand; B is a blocking group; A is an optional acyl unit; Z is an amino acid or a peptide; X is an aminobenzyl ether self-immolative spacer group; W is an optional second self-immolative group; n is an integer of 0 or 1; and w is an integer of 0 or 1, and compositions of said compounds with pharmaceutically acceptable carrier, diluent and/or excipient, and methods of delivery the drug D via the compounds.

REFERENCES:
patent: 6413507 (2002-07-01), Bentley et al.
patent: 0624377 (1994-11-01), None
Ghosh et al. ‘Nature of Linkage Between Cationic Headgroups and Cholesteryl Skeleton Controls Gene Transfection Efficiency,’ FEBS Letters. vol. 473, pp. 341-344. 2000.
Rudinger, J. (1976). Peptide Hormones (ed. J.A. Parsons). University Park Press. Baltimore. pp. 1-7.
Dermer, Gerald. “Another Anniversary for the War on Cancer.” Bio/Technology, vol. 12. Mar. 1994.
Gura, Trisha. “Systems for Identifying New Drugs are Often Faulty.” Science, vol. 278, pp. 1041-1042. Nov. 1997.
Golden, Fredrick. “Of Mice and Men: Don't Blame the Rodents” Time, pp. 44. May 18, 1998.
Bradely et al. “Limits of Cooperativeity in a Structurally Modular Protein: Response of the Notch Ankyrin Domain to Analogus Alanine Substitutions in Each Repeat.” J. Mol. Biol. vol. 324, 202, pp. 373-386.
de Groot et al., 2002, “Design, Synthesis, and Biological Evaluation of a Dual Tumor-Specific Motive Containing Integrin-targeted Plasmin-cleavable Doxorubicin Prodrug,”Molecular Cancer Therapeutics1:901-911.
de Groot et al., 2001, “Elongated Multiple Electronic Cascade and Cyclization Spacer Systems in Activatible Anticancer Prodrugs for Enhanced Drug Release,”J. Org. Chem.66(26):8815-8830.
Dubowchik et al., 1997, “Monomethoxytrityl (MMT) as a Versatile Amino Acid Protecting Group for Complex Prodrugs of Anticancer Compounds Sensitive to Strong Acids, Bases and Nucleophiles”,Tetrahedron Letters38(30):5257-5260.
Dubowchik et al., 2002, “Cathepsin B-Labile Dipeptide Linkers for Lysosomal Release of Doxorubicin from Internalizing Immunoconjugates: Model Studies of Enzymatic Drug Release and Antigen-Specific In Vitro Anticancer Activity”,Bioconjugate Chem.13:855-869.
International Search Report issued in connection with International application No. PCT/US02/30282, filed Jun. 27, 2004.
Carl et al., 1981, “A novel connector linkage applicable in prodrug design”, J. Med. Chem. 24:479-480.
Carl et al., 1980, “Protease-activated ‘prodrugs’ for cancer chemotherapy”, Proc. Natl. Acad. Sci. USA 77:2224-2228.
Chakravarty et al., 1983, “Plasmin-activated prodrugs for cancer chemotherapy. 1. Synthesis and biological activity of peptidylacivicin and peptidylphenylenediamine mustard”, J. Med. Chem. 26:633-638.
Chakravarty et al., 1983, “Plasmin-activated prodrugs for cancer chemotherapy. 2. Synthesis and biological activity of peptidyl derivatives of doxorubicin”, J. Med. Chem. 26:638-644.
Davidson et al., 1997, “The inhibition of matrix metalloproteinase enzymes”, Chemistry & Industry, Apr. 7, 1997, p. 258-261.
de Groot et al., 2000, “Synthesis and biological evaluation of 2′-carbamate-linked and 2′-carbonate-linked prodrugs of paclitaxel: selective activation by the tumor-associated protease plasmin”, J. Med. Chem. 43:3093-3102.
de Groot et al., 1999, “Synthesis and biological evaluation of novel prodrugs of anthracyclines for selective activation by the tumor-associated protease plasmin”, J. Med. Chem. 42:5277-5283.
Demchik and Sloane, 1999, “Cell-surface proteases in cancer”, in:Proteases : New Perspectives, Turk, ed., Birkhäuser Verlag, Basel, Switzerland, pp. 109-124.
Denmeade et al., 1998, “Enzymatic activation of a doxorubicin-peptide prodrug by prostate-specific antigen”, Cancer Res. 58:2537-2540.
Dubowchik and Walker, 1999, “Receptor-mediated and enzyme-dependent targeting of cytotoxic anticancer drugs”, Pharmacol. Therapeut. 83:67-123.
Dubowchik and Firestone, 1998, “Cathepsin B-sensitive dipeptide prodrugs. 1. A model study of structural requirements for efficient release of doxorubicin”, Bioorg. Med. Chem. Lett. 8:3341-3346.
Dubowchik et al., 1998, “Cathepsin B-sensitive dipeptide prodrugs. 2. Models of anticancer drugs paclitaxel (Taxol®), mitomycin C and doxorubicin”, Bioorg. Med. Chem. Lett. 8:3347-3352.
Greenwald et al., 1999, “Drug delivery systems employing 1,4- or 1,6-elimination: poly(ethylene glycol) prodrugs of amine-containing compounds”, J. Med. Chem. 42:3657-3667.
Harada et al., 2000, “Determinants for the drug release from T-0128, camptothecin analogue-carboxymethyl dextran conjugate”, J. Controlled Release 69:399-412.
Loadman et al., 1999, “Pharmacokinetics of PK1 and doxorubicin in experimental colon tumor models with differing responses to PK1”, Clin. Cancer Res. 5:3682-3688.
Mai et al., 2000, “Cell surface complex of cathepsin B/annexin II tetramer in malignant progression”, Biochim. Biophys. Acta 1477:215-230.
Niculescu-Duvaz et al., 1999, “Self-immolative anthracycline prodrugs for suicide gene therapy”, J. Med. Chem. 42:2485-2489.
Putnam et al., 1996, “Intracellularly biorecognizable derivatives of 5-fluorouracil”, Biochem. Pharmacol. 52:957-962.
Senter et al., 1996, “The role of rat serum carboxylesterase in the activation of paclitaxel and camptothecin prodrugs”, Cancer Res. 56:1471-1474.
Teicher and Sartorelli, 1980, “Nitrobenzyl halides and carbamates as prototype bioreductive alkylating agents”, J. Med. Chem. 23:955-960.
Ueda et al., 1995, “Novel, water-soluble phosphate derivatives of 2′-ethoxycarbonylpaclitaxel as potential prodrugs of paclitaxel: synthesis and antitumor evaluation”, Bioorg. Med. Chem. Lett. 5:247-252.
Wakselman, 1983, “1,4- and 1,6-eliminations from hydroxy- and amino-substituted benzyl systems: chemical and biochemical applications”, Noveau J. de Chimie 7:439-447.
Kumar et al., “Structural and Dynamic Aspects of Non-Intercalative (1:1) Binding of a Thiazole-Lexitropsin to the Decadeoxyribonucleotide d-[CGCAATTGCC]2; An1H-NMR and Molecular Modeling Study,”Journal of Biomolecular Structure&Dynamics 9(1):001-021 (1991).
Matsuba et al., “A novel synthetic DNA mino grovve binder, MS-247: antitumor activity and cytotoxic mechanism,”Cancer Chemother. Pharmacol. 46:1-9 (2000).
White et al., “On the pairing rules for recognition in the minor groove of DNA by pyrrole-imidazole polyamides,”Chemistry&Biology 4(8):569-578 (1997).
Marchini et al., “α-Bromoacryloyl derivative of distamycin A (PNU 151807): a new non-covalent minor groove DNA binder with antineoplastic activity,”British Journal of Cancer 80(7):991-997 (1999).
Toki et al., Protease-mediated Fragmentation of p-Amidobenzyl Ethers: A New Strategy for the Activation of Anticancer Prodrugs, J. Org. Chem. 2002 67:1866-1872.

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