Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1995-06-05
1998-03-10
Cook, Rebecca
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514423, A01N 4342, A61K 3144
Patent
active
057261814
ABSTRACT:
A- and/or B-ring substituted camptothecin derivatives, which are poorly water soluble (less than 5 micrograms per milliliter of water), are highly lipophilic camptothecin derivatives (HLCD) and are very active against a variety of human cancers. Because of their very poor water solubility, HLCD have not been used to treat human patients with cancer due to the inability to administer sufficient quantities of the HLCD dissolved in a pharmaceutical formulation. This invention overcomes these limitations by teaching novel pharmaceutically acceptable HLCD formulations for the direct administration of HLCD to human patients with cancer. The claimed invention also describes the methods to create solutions of HLCD and antitumor compositions of HLCD to allow the administration of HLCD in sufficient amounts to treat human patients with various types of cancer. This invention is also directed to injectable sterile solutions, antitumor compositions, solutions and suspensions comprising N-methyl-2-pyrrolidinone and a highly lipophilic camptothecin derivative.
REFERENCES:
patent: 4473692 (1984-09-01), Miyasaka et al.
patent: 4545880 (1985-10-01), Miyasaka et al.
patent: 4772589 (1988-09-01), Kaplan et al.
patent: 4778891 (1988-10-01), Tagawa et al.
patent: 5034397 (1991-07-01), Kaplan et al.
patent: 5061800 (1991-10-01), Yaegashi et al.
patent: 5573781 (1996-11-01), Brown et al.
Barilero, et al., Simultaneous determination of the camptothecin analogue CPT-11 and its active metabolite SN -38 by high performance liquid chromatography: application to plasma pharmacokinetic studies in cancer patients, Journal of Chromatography, 575 (1992) 275-280.
Bates, T. et al., Solubilizing Properties of Bile Salt Solutions I. Effect of Temperature and Bile Salt Concentration on Solubilization of Glutethimide, Griseofulvin, and Hexestrol. Journal of Pharmaceutical Sciences 55:191-199 (1966).
Bates, T. et al., Rate of Dissolution of Griseofulvin and Hexestrol in Bile Salt Solutions, Chemical Abstracts, 65:8680b, 1966.
Bates, T. et al., Solubilizing Properties of Bile Salt Solutions II. Effect of inorganic electrolyte, lipids and a mixed bile salt system on solubilization of glutethimide, griseofulvin, and hexestrol., Chem. Abstracts 64: 9517e 1966; Journal of Pharm. Sci. 55(9), 901-6 (1966)(Eng.).
Clavel, M. et al., Phase I Study of the Camptothecin Analogue CPT-11 administered as a daily infusion for 3 consecutive days; Proceedings of the American Association for Cancer Research 33:262 1568 (1992).
Creaven, P.J. et al., Plasma Camptothecin (NSC-100880) Levels During a 5-Day Course of Treatment: Relation to Dose and Toxicity; Cancer Chemotherapy Reports Part 1 56:573-578 (1972).
Culine S. et al., Phase I Study of the Camptothecin Analog CPT-11, Using a Weekly Schedule (Meeting Abstract) Proc. of Amer. Soc. Clin. Onc.; 11:110 (1992).
Emerson, D.L., In Vivo Antitumor Activity of Two New Seven-substituted Water-soluble Camptothecin Analogues; Cancer Research; 55:603-609 (1995).
Fukuoka M. et al., A Phase II Study of CPT-11, a New Derivative of Camptothecin, for Previously Untreated Non-Small-Cell Lung Cancer; Journal of Clinical Oncology, 10(1):16-20, (1992).
Giovanella, B. et al., DNA Topoisomerase I-Targeted Chemotherapy of Human Colon Cancer in Xenografts; Science 246:1046-1048 (1989).
Gottleib, J. et al., Preliminary Pharmacologic and Clinical Evaluation of Camptothecin Sodium (NSC-100880); Cancer Chemotherapy Reports Part 1 54:461-470, (1970).
Gottlieb, J. et al., Treatment of Malignant Melanoma With Camptothecin (NSC-100880); Cancer Chemotherapy Reports Part 1 56:103-105, (1972).
Hsiang, et al., Arrest of Replication Forks by Drug-stabilized Topoisomerase I-DNA Cleavable Complexes as a Mechanism of Cell Killing by Camptothecin; Cancer Research 49:5077-2082, (1989).
Houghton, P. et al., Therapeutic Efficacy of the Topoisomerase I Inhibitor against Human Tumor Xenografts: Lack of Cross-Resistance in Vivo in Tumors with Acquired Resistance to the Topoisomerase I Inhibitor 9-Dimethylaminomethyl-10-hydroxycamptothecin; Cancer Research 53:2823-2829, (1993).
Jaxel, C. et al., Structure-Activity Study of the Actions of Camptothecin Derivatives on Mammalian Topoisomerase I: Evidence for a Specific Receptor Site and a Relation to Antitumor Activity; Cancer Research 49:1465-1469, (1989).
Kaneda, N. et al., Metabolism and Pharmacokinetics of the Camptothecin Analogue CPT-11 in the Mouse; Cancer Research 50:1715-1720, (1990).
Kano, Y. et al., Effects of CPT-11 in Combination with Other Anti-Cancer Agents in Culture; Int. J. Cancer, 50:604-610 (1992).
Kanzawa, F. et al., Role of Carboxylesterase on Metabolism of Campthothecin Analog (CPT-11) in Non-Small Cell Lung Cancer Cell Line PC-7 Cells; Proceedings of the American Association for Cancer Research, 33:A2552, (1992).
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).
Kunimoto, T. et al., Antitumor Activity of against Murine Tumors; Cancer Research 47:5944-5947, (1987).
Luzzio, M.J. et al., Synthesis and Antitumor Activity of Novel Water Soluble Derivatives of Camptothecin as Specific Inhibitors of Topoisomerase I. J. Med. Chem. 38:395-401, (1995).
Malone, M. et al., Desoxycholic Acid Enhancement of Orally Administered Reserpine; Journal of Pharmaceutical Sciences, 55:972-974, (1966).
Masuda, N. et al., CPT-11: A New Derivative of Camptothecin for the Treatment of Refractory or Relapsed Small-Cell Lung Cancer; Journal of Clinical Oncology, 10(8):1225-1229, (1992).
Moertel, C., et al., Phase II Study of Camptothecin (NSC-100880) in the Treatment of Advanced Gastrointestinal Cancer; Cancer Chemotherapy Reports part I, 56(1):95-101 (1972).
Muggia, F., et al., Phase I Clinical Trial of Weekly and Daily Treatment With Camptothecin (NSC-100880): Correlation With Preclinical Studies; Cancer Chemotherapy Reports Part 1, 56(4):515-521, (1972).
Negoro, S., et al., Phase I Study of Weekly Intravenous Infusions of CPT-11, a New Derivative of Camptothecin in the Treatment of Advanced Non-Small-Cell Lung Cancer; Journal of the National Cancer Institute, 83(16): 1164-1168, (1991).
Negoro, S., et al., Phase II Study of CPT-11, New Camptothecin Derivative, In Small Cell Lung Cancer (SCLC) (Meeting Abstract); Proc. Annu. Meet. Am. Soc. Clin. Oncol. 10:A822, (1991).
Niimi, S., et al., Mechanism of Cross-Resistance to a Camptothecin Analogue (CPT-11) in a Human Ovarian Cancer Cell Line Selected by Cisplatin; Cancer Research 52:328-333, (1992).
Ohe, Y., et al., Phase I Study and Pharmacokinetics of CPT-11 With a 5-Day Continous Infusion; Journal of the National Cancer Institute; 84(12):972-974, (1992).
Ohno, R., et al., An Early Phase II Study of CPT-II: A New Derivative of Camptothecin, for the Treatment of Leukemia and Lymphoma; Journal of Clinical Oncology; 8(11):1907-1912, (1990).
Pantazis, P., et al., Cytotoxic Efficacy of 9-Nitrocamptothecin in the Treatment of Human Malignant Melanoma Cells in Vitro; Cancer Research; 54:771-776, (1994).
Pommier, Y., et al., Camptothecins: Mechanisms of Action and Resistance; Cancer Investigation, Presented at the "Chemotherapy Foundation Symposium X Innovative Cancer Chemotherapy for Tommorrow," p. 3, 1992.
Potmesil, M., et al., Preclinical and Clinical Development of DNA Topoisomerase I Inhibitors in the United States. in Andoh, T., Ikeda, H. Oguro, M. (eds) : Molecular Biology of DNA Topoisomerases and Its Application to Chemotherapy. Boca Raton, FL., CRC Press, Inc. 301-311, (1993).
Rivory, L.P., et al., Kinetics of the in Vivo Interconversion of the Carboxylate and Lactone Forms of Irinotecan (CPT-11) and of Its Metabolite SN-38 in patients; Cancer Research; 54:6330-6333, (1994).
Rothenberg, M.L., et al., A Phase I and Pharmacokinetic Trial of CPT-11 in Patients With Refractory Solid Tumors (Meeting Astract); Amer. Soc. Clin. Onc.; 11:113, (1992).
Rothenberg, M.L. et al., Phase I and Parmacokinetic Trial of Weekly CPT-11; 11:2194-2204, (1993).
Rowinsky, E. et al., Phase I and Pharmacologic Study of CPT-11, A Semisynthetic
Haridas Kochat
Hausheer Frederick H.
Murali Dhanabalan
Reddy Dasharatha Gauravaram
BioNumerik Pharmaceuticals, Inc.
Cook Rebecca
Dodd Thomas J.
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