Patent 7384977 Issued on June 10, 2008. Estimated Expiration Date: August 31, 2026. Estimated Expiration Date is calculated based on simple USPTO term provisions. It does not account for terminal disclaimers, term adjustments, failure to pay maintenance fees, or other factors which might affect the term of a patent.
514/511, Two of the cyclos share at least three ring members (i.e., bridged)424/1.11, RADIONUCLIDE OR INTENDED RADIONUCLIDE CONTAINING; ADJUVANT OR CARRIER COMPOSITIONS; INTERMEDIATE OR PREPARATORY COMPOSITIONS424/1.65, In an organic compound424/9.1, IN VIVO DIAGNOSIS OR IN VIVO TESTING424/1.69, Attached to peptide or protein of 2+ amino acid units (e.g., dipeptide, folate, fibrinogen, transferrin, sp. enzymes); derivative thereof514/510, Polycyclo ring system514/449Oxygen containing hetero ring
Disclosed are water soluble compositions of paclitaxel and docetaxel formed by conjugating the paclitaxel or docetaxel to a water soluble polymer such as poly-glutamic acid, poly-aspartic acid or poly-lysine. Also disclosed are methods of using the compositions for treatment of tumors, auto-immune disorders such as rheumatoid arthritis. Other embodiments include the coating of implantable stents for prevention of restenosis.
Other References
Zunino et al., “Anti-Tumor Activity of Daunorubicin Linked to Poly-L-Aspartic Acid,” Int. J. Cancer, vol. 30, 1982, pp. 465-470.
Yu, “Effect of polymer structure on antitumor activity of polyaminio acid-paclitaxel conjugates,” Proc. Amer. Assoc. Cancer Research, vol. 39, 1998, p. 167, Abstract No. 1144.
Yang et al., “Application of surface-modified microcapsules to target estrogen receptors,” Pharm. Res., vol. 9, 1992, p. S73, Abstract No. Biotec 2027.
Wen et al., “Potentiation of Antitumor Activity of PG-TXL with Anti-EGFR Monoclonal Antibody C225 in MDA-MB-468 Human Breast Cancer Xenograft,” Proc Am Assoc Cancer Res, vol. 41, 2000, Abstract No. 2052.
Wadkins et al., “Water Soluble 20(S)-Glycinate Esters of 10,11-Methylenedioxycamptothecins Are Highly Active Against Human Breast Cancer Xenografts” Cancer Research, vol. 59, 1999, pp. 3424-3428.
Todd et al., “Phase I and pharmacological Study of CT-2103, a poly (L-glutamic Acid)-paclitaxel conjugate,” Journal of Clinical Oncology, vol. 439, 2001.
Singer et al., “Poly-L-Glutamic Acid Paclitaxel Conjugate (PG-TXL): A water-soluble biodegradable conjugate with decreased toxicity and enhanced efficacy,” 4th International Symposium on Polymer Therapeutics, 2000.
Shi, “Poly (L-glutamic acid)-paclitaxel and paclitaxel have different pharmacological properties,” Proc. Amer. Assoc. for Cancer Research, vol. 39, 1998, p. 189, Abstract No. 1294.
Shaffer et al., “In vivo identification of monoglutamyl paclitaxel metabolite from poly-L-glutamic acid-paclitaxel (CT-2103) in tumor bearing mice,” Proceedings of the 49th ASMA Conference on Mass Spectrometry and Allied Topics, A010970, 2001.
Scudiero et al., “Evaluation of a soluble tetrazolium/formazan assay for cell growth and drug sensitivity in culture using human and other tumor cell lines,” Cancer Research, vol. 48, 1988, pp. 4827-4833.
Pesenti et al., “Synthesis and biological activity of water soluble polymer-bound taxol derivatives,” Proc. Amer. Assoc. Cancer Res., vol. 36, 1995, p. 307, Abstract No. 1824.
Morimoto et al., “Antitumor agent poly (amino acid) conjugates as a drug carrier in cancer chemotherapy,” J. Pharm. Dyn., vol. 7, 1984, pp. 688-698.
Multani et al., “Paclitaxel and water-soluble poly (L-gluatmic acid)-paclitaxel, induce direct chromosomal Abnormalities and cell death in a murine metastatic melanoma cell line,” Anticancer Res, vol. 17, 1997, pp. 4269-4274.
Mason et al., “Poly (L-glutamic Acid)-paclitaxel dramatically enhances the anti-tumor efficacy of radiotherapy,” AACR—NCI—EORTC, vol. 397, 2001, Miami Beach, Florida.
Li et al., “Tumor irradiation enhances the tumor-specific distribution of poly(L-glutamic acid)-conjugated paclitaxel and its antitumor efficacy,” Clin Cancer Res, vol. 6, 2000, pp. 2829-2834.
Li et al., “Antitumor activity of Poly(L-glutamic acid)-Paclitaxel on syngeneic and xenografted tumors,” Clin Cancer Res, vol. 5, 1999, pp. 891-897.
Li et al., “Enhancement of tumor radioresponse of a murine ovarian carcinoma by poly(L-glutamic acid)-paclitaxel conjugate,” Ninth International Symposium on Recent Advances in Drug Delivery Systems, 1999, Salt Lake City, UT.
Li et al., “Antitumor activity of Poly(L-glutamic acid)-Paclitaxel on syngeneic and xenografted tumors,” Proc Am Assoc Cancer Res, vol. 40, 1999, Abstract No. 1909.
Li et al., “Synthesis and evaluation of water-soluble polyethylene glycol-paclitaxel conjugate as a paciitaxei prodrug,” Anticancer Drugs, vol. 7, 1996, pp. 642-618.
Li et al., “Water-soluble polyglutamic acid paclitaxel conjugate (PGA-paclitaxel): antitumor regression in rats braeing 13762 mammary carcinoma,” American Association Pharmaceutical Scientists Meeting, vol. 13, 1996, p. S368.
Li et al., “Synthesis, biodistribution and imaging properties of indium-111-DTPA-paclitaxel in mice bearing mammary tumors,” J. Nucl. Med., vol. 38, 1997, pp. 1042-1047.
Li et al., “Formation and characterization of CDDP loaded poly(benzyl L-glutamate) and poly (di-tactic acid) microcarpsules for chemoembolzation,” Proc. Amer. Assoc. Cancer Res., vol. 35, 1994, p. 336, Abstract No. 2003.
Li et al., “Cytotoxic and antitumor activity of water-soluble paclitaxel prodrug,” Proc. Amer. Assoc. Cancer Res, vol. 37, 1996, pp. 376-377, Abstract No. 2570.
Li et al., “Synthesis and evaluation of PEG-paclitaxel conjugate as a water-soluble paclitaxel prodrug,” Proc. Amer. Assoc. Cancer Res, vol. 37, 1996, p. 376, Abstract No. 2569.
Li et al., “Complete Regression of Well-Established Tumors Using a Novel Water-Soluble Poly-(L-Glutamic Acid)-Paclitaxel Conjugate,” Cancer Research, vol. 58, 1998, pp. 2404-2409.
Ke et al., “Schedule-independent radiosensitization of a murine ovarian OCa-1 tumor by PG-TXL,” Proc Am Assoc Cancer Res, vol. 40, 1999, Abstract No. 4223.
Ke et al., “Elevated serum VEGF as a prognosis marker in combined radiation and PG-TXL (CT-2103) therapy in mice with murine ovarian OCa-1 tumor,” Proc Amer Assoc Cancer Res, vol. 42, 2001, Abstract No. 3873.
Kato et al., “Antitumor activity of 1-βD-arabinofuranosylcytosine conjugated with polyglutamic acid and its derivative,” Cancer Res., vol. 44, 1984, pp. 25-30
Horwitz et al., “Taxol, mechanisms of action and resistance,” J. Natl. Cancer Inst. Monographs, vol. 15, 1993, pp. 15-61.
Gilbert et al., “Novel water soluble paclitaxel derivatives: Evaluation of PEG-paclitaxel's in vitro and in vivo effects,” Proc. Amer. Assoc. Cancer Res., vol. 38, 1997, p. 225, Abstract #1512.
De Vries et al., “Pharmacokinetcis (PK) and biodistribution of poly-(L)-glutamic acid (PG) paclitaxesl (TXL) (CT-2103) in mice with subcutaneous B-16 melanomas,” Proceedings of the 11th AACR-NCI-EORTC Symposium, 2000 Amsterdam, Netherlands.
De Vries et al., “Optimization of the anti-tumor activity of water-soluble poly L-glutamic acid (PG)- paclitaxel (TXL) conjugates,” AACR-NCI-EORTC 92, 1999, pp. 22, Abstract No. 451, Washington, DC.
De Vries et al., “CT-2103: A water soluble poly-L-glutamic acid (PG)-Paclitaxesl (TXL) conjugate has enhanced efficacy on MDR-1+human colon carcinoma cell line xenografts compared to free TXL,” AACR, 2001, Abstract No. 462.
De Vries et al., “Conjugation of Docetaxel (DTXL) to Poly L-Glutamic Acid (PG) Increases Anti-Tumor Efficacy,” Proceedings of the American Association for Cancer Research, vol. 41, 2000, p. 323, Abstract No. 2051.
De Bono et al., “Phase I Pharmacokinetic (PK) Study of Mag-CPT-(PNO 166148) A Polymer Derivative of Camptothecin (CPT),” Pharmicia, date not available.
Conover et al., “Camptothecin Delivery Systems: The Antitumor Activity of a Camptothecin-20-0-Polyethylene Glycol Ester Transport Form,” Anticancer Research, vol. 17, 1997, pp. 3361-3368.
Conover et al., “Camptothecin Delivery Systems: The Utility of Amino Acid Spacers for the Conjugation of Camptothecin with Polyethylene Glycol to Create Prodrugs,” Anti-Cancer Drug Design, vol. 14, 1999, pp. 499-506, ® Oxford University Press.