Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1995-06-07
1997-10-07
Goldberg, Jerome D.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
A61K 3144
Patent
active
056748736
ABSTRACT:
10-hydroxy 7-ethyl camptothecin (HECPT), an active metabolite of the camptothecin analog CPT-11, is poorly soluble in water. Because of its poor water solubility, HECPT has not been directly administered by parenteral or oral routes in human patients for the purpose of inhibiting the growth of cancer cells. There is also unpredictable interpatient variability in the metabolic production of HECPT from CPT-11 which limits the utility of CPT-11. This invention overcomes these limitations by teaching novel pharmaceutically acceptable lactone stable HECPT formulations for the direct administration of HECPT. The claimed invention also describes novel dosages, schedules, and routes of administration of the lactone stable HECPT formulations to patients with various forms of cancer.
REFERENCES:
patent: 4339276 (1982-07-01), Miyasaka et al.
patent: 4399276 (1983-08-01), Miyasaka et al.
patent: 4399282 (1983-08-01), Miyasaka et al.
patent: 4473692 (1984-09-01), Miyasaka et al.
patent: 4545880 (1985-10-01), Miyasaka et al.
patent: 4684630 (1987-08-01), Repta et al.
patent: 4734284 (1988-03-01), Terada et al.
patent: 4778891 (1988-10-01), Tagawa et al.
patent: 5061800 (1991-10-01), Miyasaka et al.
patent: 5180722 (1993-01-01), Wall et al.
patent: 5225404 (1993-07-01), Giovannella et al.
patent: 5227380 (1993-07-01), Wall et al.
Akimoto, K., et al., Selective and Sensitive Determination of Lactone and Hydroxy Acid Forms of Camptothecin and Two Derivatives (CPT-11 and SN-38) by High Performance Liquid Chromatography with Fluorescence Detection. Journal of Chromatography, 588:165-170, 1991.
Taxotere, Topotecan, and CPT-11: Clinical Trials Confirm Early Promise. Oncology Times, written by O. Baer, pp. 8-10, May 1993.
Bates, T.R., et al., Solubilizing Properties of Bile Salt Solutions I--Effect of Temperature and Bile Salt Concentration On Solubilization of Gluthethimide, Griseofulvin and Hexestrol. Journal of Pharmaceutical Sciences, 55:191-199, 1966.
Bates, T.R., et al., Rates of Dissolution of Grisofulvin and Hexestrol in Bile Salt Solutions. Chem. Abstracts 65:8680b, 1966.
Bates, T.R., et al., Solubilizing Properties of Bile Salt Solutions on Glutethimide, Griseofulvin, and Hexestrol. Chem. Abstracts 65:15165a, 1966.
Clavel, M., et al., Phase I Study of the Camptothecin Analogue CPT-11, Administered Daily for 3 Consecutive Days. Proc. Amer. Assoc. Cancer Res. 3:83, 1992.
Creavan, P.J., et al., Plasma Camptothecin (NSC 100880) Levels During a 3-Day Course of Treatment: Relation to Dose and Toxicity. Cancer Chemotherapy Rep. 56:573-578, 1972.
Culine, S., et al., Phase I Study of the Camptothecin Analogue CPT-11, Using a Weekly Schedule. Proc. of Amer. Soc. Clin. Onc. 11:110, 1992.
Eckardt, J., et al., Topoisomerase I Inhibitors: Promising Novel Compounds. Contemporary Oncology, pp. 47-60, 1993.
Fukuoka, M., et al., A Phase II Study of CPT-11, A New Derivative of Camptothecin, for Previously Untreated Non Small-Cell Lung Cancer. J. Clin. Onc. 10(1):16-20, Jan. 1992.
Gionvanella, B.C., et al., DNA Topoisomerase I--Targeted Chemotherapy of Human Colon Cancer in Xenografts. Science 246:1046-1048, Nov. 1989.
Gottlieb, J.A., et al., Preliminary Pharmacologic and Clinical Evaluation of Camptothecin Sodium (NSC-100880). Cancer Chemotherapy Reports 54(6):461-470, Dec., 1970.
Gottlieb, J.A., et al, Treatment of Malignant Melanoma with Camptothecin, (NSC100880). Cancer Chemotherapy Reports 56(1):103-105, Feb., 1972.
Hsiang, Y.H., et al., Arrest of Replication Forks by Drug-stabilized Topoisomerase I-DNA Cleavable Complexes as a Mechanism of Cell Killing by Camptothecin Analogues. Cancer Res. 49:5077-5082, Sep., 1989.
Jaxel, C., et al., Structure Activity of Study of the Actions of Camptothecin Derivatives on Mammalian Topoisomerase I: Evidence for a Specific Receptor Site and A Relation to Antitumor Activity. Cancer Res. 49:1465-1469, Mar., 1989.
Kaneda, N., et al, Metabolism and Pharmacokinetics of the Camptothecin Analogue CPT-11 in the Mouse. Cancer Research 50:1715-1720, Mar., 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 Camptothecin Analog (CPT-11) in Non-Small Cell Lung Cancer Cell Line PC-7 Cells (Meeting Abstract). Proc. Annual Meet. Am. Assoc. Cancer Res. 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 Res. 51:4187-4191, Aug., 1991.
Kingsbury, W.D., et al., Synthesis of Water-Soluble (Aminoalkyl) Camptothecin Analogues: Inhibition of Topoisomerase I and Antitumor Activity. J. Med. Chem. 34:98-107, 1991. Piperidino! Cabronyloxy-Camptothecin Against Murine Tumors. Cancer Res. 47:5944-5947, Nov., 1987.
Malone, M.H., et al., Desoxycholic Acid Enhancement of Orally Administered Reserpine. Journal of Pharmaceutical Sciences, 55(9):972-974, Sep., 1966.
Masuda, N., et al., CPT-11: A New Derivative of Camptothecin for the Treatment of Refractory or Relapsed Small-Cell Lung Cancer. J. Clin. Onc. 10(8):1225-1229, Aug., 1992.
Moertel, C.G., et al., Phase II Study of Camptothecin (NSC-100880) in the Treatment of Advanced Gastrointestinal Cancer. Cancer Chemotherapy Rep. 56(1):95-101, Feb., 1972.
Muggia, F.M., et al., Phase I Clinical Trial of Weekly and Daily Treatment With Camptothecin (NSC-100880): Correlation With Preclinical Studies. Cancer Chemotherapy Rep. 56(4):515-521, Aug., 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. JNCI 83(16):1164-1168, Aug., 1991.
Negoro, S., et al., Phase II Study of CPT-11, a New Camptothecin Derivative, in Small Cell Lung Cancer. Proc. Annu. Meet. of Amer. Soc. Clin. Onc. 10:241, Aug., 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 Res. 52:328-333, Jan., 1992.
Ohe, Y., et al., Phase I Study and Pharmacokinetics of CPT-11 With 5-Day Continuous Infusion. JNCI 84(12): 972-974, Jun., 1992.
Ohne, R., et al., An Early Phase II Study of CPT-11: A New Derivative of Camptothecin, for the Treatment of Leukemia and Lymphoma. J. Clin. Onc. 8(11):1907-1912, Nov., 1990.
Pommier, Y., et al., Camptothecins: Mechanism of Action and Resistance (Meeting Abstract). Cancer Investigation, Presented at the "Chemotherapy Foundation Symposium X Innovative Cancer Chemotherapy for Tomorrow", pp. 3-6, 1992.
Rothenberg, M.L., et al., A Phase I and Pharmacokinetic Trial of CPT-11 in Patients With Refractory Solid Tumors. Proceedings of Amer. Soc. Clin. Onc. 11:113, 1992.
Rotherberg, M.L., et al., Phase I and Pharmacokinetic Trial of Weekly CPT-11. Journal of Clinical Oncology. 11(11):2194-2204, Nov., 1993.
Rowinsky, E., et al., Phase I and Pharmacologic Study of CPT-11, A Semisynthetic Topoisomerase I-Targeting Agent, on a Single-Dose Schedule (Meeting Abstract). Proc. Annu. Meet. of Amer. Soc. Clin. Onc. 11:115,1992.
Sawada, S., et al., Synthesis and Antitumor Activity of 20 (S)-Camptothecin Derivatives: Carbonate-Linked, Water-Soluble, Derivatives of 7-Ethyl-10-Hydroxycamptothecin. Chem. Pharm. Bull. 39(6):1446-1454, 1991.
Shimada, Y., et al., Phase II Study of CPT-11, New Camptothecin Derivative, in the Patients with Metastatic Colorectal Cancer. Proc. of Amer. Soc. Clin. Onc. 10:135, Mar., 1991.
Takeuchi, S., et al., Late Phase II Study of CPT-11, A Topoisomerase I Inhibitor, in Advanced Cervical Carcinoma (CC) (Meeting Abstract). Proc. Annu. Meet. of Amer. Soc. Clin. Onc. 11:224, 1992.
Wall, M.E., et al., Plant Anti-Tumor Agents I--The Isolation and Structure of Camptothecin, a Novel Alkaloidal Leulemia and Tumor Inhibitor from Camptothecin Acuminata. J.Amer.Chem.Soc. 88(16):3888-3890, Aug., 1966.
Westergaard, H., et al., The Mechanism Whereby Bile Acid Mycelles Increase the Rate of Fatty Acid and Cholesterol Uptake Into the Intestinal Mucosal Cell. Journal of Clinical Investigation, 58:97-108 Jul. 1976 Va
Haridas Kochat
Hausheer Frederick H.
BioNumerik Pharmaceuticals, Inc.
Dodd Thomas J.
Goldberg Jerome D.
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