Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2007-02-09
2008-12-09
Aulakh, Charanjit S (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C546S048000
Reexamination Certificate
active
07462627
ABSTRACT:
A four arm-polyethylene glycol-7-ethyl-10-hydroxycamptothecin conjugate, such as,is disclosed. Methods of making the conjugates and methods of treating mammals using the same are also disclosed.
REFERENCES:
patent: 4473692 (1984-09-01), Miyasaka et al.
patent: 5614549 (1997-03-01), Greenwald et al.
patent: 5648506 (1997-07-01), Desai et al.
patent: 5681567 (1997-10-01), Martinez et al.
patent: 5840900 (1998-11-01), Greenwald et al.
patent: 5840973 (1998-11-01), Yasukohchi et al.
patent: 5859022 (1999-01-01), Hausheer et al.
patent: 5880131 (1999-03-01), Greenwald et al.
patent: 5902588 (1999-05-01), Greenwald et al.
patent: 5948155 (1999-09-01), Yui et al.
patent: 5965566 (1999-10-01), Greenwald et al.
patent: 6011042 (2000-01-01), Greenwald et al.
patent: 6111107 (2000-08-01), Greenwald et al.
patent: 6121451 (2000-09-01), Henegar et al.
patent: 6127355 (2000-10-01), Greenwald et al.
patent: 6153655 (2000-11-01), Martinez et al.
patent: 6177087 (2001-01-01), Greenwald et al.
patent: 6194580 (2001-02-01), Greenwald et al.
patent: 6395266 (2002-05-01), Martinez et al.
patent: 6403569 (2002-06-01), Achterrath
patent: 6608076 (2003-08-01), Greenwald et al.
patent: 6638499 (2003-10-01), Martinez et al.
patent: 6649778 (2003-11-01), Zhao et al.
patent: 6756037 (2004-06-01), Greenwald et al.
patent: 6875841 (2005-04-01), Sakanoue et al.
patent: 2001/0041172 (2001-11-01), Bentley et al.
patent: 2002/0182172 (2002-12-01), Bentley et al.
patent: 2003/0105275 (2003-06-01), Bentley et al.
patent: 2004/0009229 (2004-01-01), Unger et al.
patent: 2004/0058981 (2004-03-01), Lai et al.
patent: 2004/0077595 (2004-04-01), Cheng et al.
patent: 2004/0247624 (2004-12-01), Unger et al.
patent: 2005/0112088 (2005-05-01), Zhao et al.
patent: 2005/0226843 (2005-10-01), Bentley et al.
patent: 2008/0058364 (2008-03-01), Sapra
patent: 2008/0193408 (2008-08-01), Zhao et al.
patent: 0757049 (1999-03-01), None
patent: 9841562 (1998-09-01), None
patent: 0064486 (2000-11-01), None
patent: 0168066 (2001-09-01), None
patent: 0174402 (2001-10-01), None
patent: 02089789 (2002-11-01), None
patent: 03031467 (2003-04-01), None
patent: 03037384 (2003-05-01), None
patent: 03037385 (2003-05-01), None
patent: 2004060967 (2004-07-01), None
Greenwald, R. B., et al., Camptothecin-20-PEG ester Transport Forms: the Effect of . . . , Bioorganic & Medicinal Chemistry, 6: 551-562, 1998.
Conover, C. D., et al., Camptothecin delivery systems: the utility of amino acid spacers for . . . , Anticancer Drug Design, 14: 499-506, 1999.
Carpino, L. A., et al., New family of base- and nucleophile-sensitive amino-protecting groups. A Michael-acceptor-based deblocking process. Practical utilization of the 1,1-dioxobenzo[b]thiophene-2-ylmethylcarbonyl (Bsmoc) group, Journal of the American Chemical Society, 119: 9915-9916, 1997.
Chabot, G. G., Clinical pharmacokinetics or irinotecan, Clinical Pharmacokinet, 33: 245-259, 1997.
Choe, Y. H., et al., Anticancer drug delivery systems: N4-acyl-poly(ethyleneglycol) prodrugs of ara-C. I. Efficacy in solid tumors, Journal of Controlled Release, 79: 41-53, 2002.
Conover, C. D., et al., Campothecin delivery systems: enhanced efficacy and tumor accumulation of campotothecin following its conjugation to polyethylene glycol via a glycine linker, Cancer Chemotherapy Pharmacology, 407-414, 1998.
Duncan, R., Polymer conjugates as anticancer nanomedicines, Nature Reviews: Cancer, 6: 688-701, 2006.
Garcia-Carbonero, R., et al., Current perspectives on the clinical experience, pharmacology, and continued development of the camptothecins, Clinical Cancer Research, 8:641-661, 2002.
Gottlieb, J. A., et al., Preliminary pharmacologic and clinical evaluation of camptothecin sodium (NSC-100880), Cancer Chemotherapy Reports, 54: 461-470, 1970.
Greenwald, R. B., et al., Synthesis, isolation, and characterization of 2'-paclitaxel glycinate: an application of the Bsmoc protecting group, Journal of Organic Chemistry, 68: 4894-6, 2003.
Greenwald, R. B. et al., Drug delivery systems. 2. Camptothecin 20-O-poly(ethylene glycol) ester transport forms, Journal of Medicinal Chemistr, 39: 1938-1940, 1996.
Greenwald, R. B., et al., Drug delivery systems: water soluble taxol 2'-poly(ethylene glycol) ester prodrugs-Design and in vivo effectiveness, Journal of Medicinal Chemistry, 39: 424-431, 1996.
Greenwald, R. B., et al., Effective drug delivery by PEGylated drug conjugates, Advanced Drug Delivery Reviews, 55: 217-250, 2003.
Kaneda, N., Metabolism and pharmacokinetics of the camptothecin analogue CPT-11 in the mouse, Cancer Research, 50: 1715-1720, 1990.
Kawato, Y., et al., Intracellular roles of SN-38, a metabolite of the camptothecin derivative CPT-11, in the antitumor effect of CPT-11, Cancer Research, 51: 4187-4191, 1991.
Liu, X., et al., Degradation of camptothecin-20(S)-glycinate ester prodrug under physiological conditions, Journal of Pharmaceutical and Biomedical Analysis, 35: 1113-1125, 2004.
Maeda, H., et al., Tumor vascular permeability and the EPR effect in macromolecular therapeutics: a review, Journal of Controlled Release, 65: 271-284, 2000.
Mathijssen, R. H. J., et al., Clinical pharmacokinetics and metabolism of irinotecan (CPT-11), Clinical Cancer Research, 7: 2182-2194, 2001.
NOF Corp. Drug Delivery System catalog, ver. 8.
Pommier, Y., Topoisomerase I inhibitors: camptothecins and beyond, Nature Reviews: Cancer, 6: 789-802, 2006.
Rowinsky, E. K., et al., A Phase I and pharmacokinetic study of pegylated camptothecin as a 1-hour infusion every 3 weeks in patients with advanced solid malignancies, Journal of Clinical Oncology, 148-157, 2003.
Senter, P. D., et al., Identifcation and activites of human carboxylesterases for the activation of CPT-11, a clinically approved anticancer drug, Bioconjugate Chemistry, 12: 1074-1080, 2001.
Slatter, J. G., et al., Bioactivation of the anticancer agent CPT-11 to SN 38 human hepatic microsomal carboxylesterases and the in virto assessment of potential drug interactions, Drug Metabolism and Disposition, 25: 1157-1164, 1997.
Slatter, J. G., et al., Pharmacokinetics, metabolism, and excretion of irinotecan (CPT-11) following i.v. infusion of [14C]CPT-11 in cancer patients, Drug Metabolism and Disposition, 28: 423-433, 2000.
Smith, N. F., et al., Pharmacogenetics of irinotecan metabolism and transport: an update, Toxicology in Vitro, 20:163-175, 2006.
Ulukan, H., et al., Camptothecins: a review of their chemotherapeutic potential, Drugs, 62: 2039-57, 2002.
Zhang, J. A., et al., Development and characterization of a novel liposome-based formulation of SN-38, International Journal of Pharmaceutics, 270: 93-107, 2004.
Zhao, H., et al., 20-O-acylcamptothecin derivatives: evidence for lactone stabilization, Journal of Organic Chemistry, 65: 4601-4606, 2000.
International Search Report and Written Opinion dated Aug. 13, 2008 issued in PCT/US07/03808.
Zalipsky et al., Attachment Of Drugs to Polyethylene Glycols, European Polymer Journal, 1983, 19(12): 1177-1183.
Greenwald et al., Poly(ethylene glycol) Conjugated Drugs and Prodrugs: A Comprehensive Review, Critical Review in Therapeutic Drug Carrier Systems, 2000, 17(2): 101-161.
Rubio Maria Belen
Sapra Puja
Wu Dechun
Zhao Hong
Aulakh Charanjit S
Enzon Pharmaceuticals, Inc.
Lucas & Mercanti LLP
LandOfFree
Multi-arm polymeric conjugates of... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Multi-arm polymeric conjugates of..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Multi-arm polymeric conjugates of... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-4041944