Method of manufacturing of 7-ethyl-10-hydroxycamptothecin

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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Reexamination Certificate

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07544801

ABSTRACT:
The method of manufacturing of 7-ethyl-10-hydroxycamptothecin of formula I characterized in that 7-ethyl-1,2,6,7-tetrahydrocampotothecin of formula IV is oxidized with an oxidizing agent selected from the group comprising iodosobenzene, an ester of iodosobenzene, sodium periodate, potassium periodate, potassium peroxodisulfate and ammonium peroxodisulfate, in a solvent formed by a saturated aliphatic monocarboxylic acid containing 1 to 3 carbon atoms, and in the presence of water.

REFERENCES:
patent: 3894029 (1975-07-01), Winterfeldt et al.
patent: 4031098 (1977-06-01), Sugasawa
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: 4604463 (1986-08-01), Miyasaka et al.
patent: 4914205 (1990-04-01), Sawada et al.
patent: 5061800 (1991-10-01), Yaegashi et al.
patent: 5491237 (1996-02-01), Fang et al.
patent: 5602141 (1997-02-01), Bedeschi et al.
patent: 5734056 (1998-03-01), Burk et al.
patent: 5843954 (1998-12-01), Yaegashi et al.
patent: 6235907 (2001-05-01), Henegar et al.
patent: 6310210 (2001-10-01), Ogawa et al.
patent: 6403569 (2002-06-01), Achterrath
patent: 6444820 (2002-09-01), Henegar et al.
patent: 6743918 (2004-06-01), Yaegashi et al.
patent: 6794370 (2004-09-01), Achterrath
patent: 7126000 (2006-10-01), Ogawa et al.
patent: 7151179 (2006-12-01), Lin et al.
patent: 2004/0235878 (2004-11-01), Lin et al.
patent: 2005/0272757 (2005-12-01), Naidu
patent: 2006/0199961 (2006-09-01), Dobrovolny
patent: 74770 (1983-03-01), None
patent: 88642 (1983-09-01), None
patent: 51289 (1986-04-01), None
patent: 74256 (1986-11-01), None
patent: 154584 (1988-02-01), None
patent: 154583 (1988-09-01), None
patent: WO96/31513 (1996-10-01), None
patent: WO2004/100897 (2004-11-01), None
patent: WO2005/019223 (2005-03-01), None
patent: WO2005/058910 (2005-06-01), None
“Combination of Irinotecan (CPT-11) and 5-Fluorouracil with an analysis of cellular determinants of drug activity,” Pavillard et al., Biochemical Pharmacology, vol. 56: 1315-1322, 1998.
“Clinical advances with topoisomerase I inhibitors in gastrointestinal malignancies,” Armand, Jean-Pierre et al., Anti-Cancer Drugs 10 (Suppl. 1): S5-S12 (1999).
“Phase I/II study of escalating dose of CPT-11 in combination with LV5FU2 (“De Gramont” regimen) every 2 weeks in the treatment of colorectal cancer (CRC) after 5-FU failure,” Ducreux, M. et al., Abstract 823, Proc. of Amer. Soc. Clin. Oncol. 16:234a (1997).
“Phase I study of a weekly schedule of irinotecan (CPT-11), high-dose folinic acid (FA) and 5-fluorouracil (5-FU) as first line chemotherapy (CT) in metastatic colorectal cancer: Final results,” Vanhoeffer, U. et al., Abstract 779, Proc. of Amer. Soc. Clin. Oncol. 17:202a (1998).
“Irinotecan (CPT-11) in the treatment of gastrointestinal cancers,” Nishiyama, M., Japanese J. Chemotherapy 46(8):292-296 (1998).
“CPT-11 (Irinotecan) and 5-Fluorouracil: a Promising Combination for Therapy of Colorectal Cancer,” Saltz, L. et al., European J. Cancer 32A(Suppl. 3):S24-S31 (1996).
“Phase I/II study of CPT-11 in combination with LV5FU2 (De Gramont-Regimen) every 2 weeks for the treatment of colorectal cancer (CRC) after 5-FU failure,” Seitz, J.F. et al., Abstract 261, Annals of Oncology 9 (Suppl. 2):68 (1998).
“Phase I study of a weekly schedule of irinotecan (CPT-11) in combination with high-dose folinic acid and 5-fluorouracil as first line chemotherapy in patients with advanced colorectal cancer,” Vanhoefer, U. et al., Abstract 967, Proc. of Amer. Soc. Clin. Oncol. 16:272a (1997).
“Synthesis and Antitumor Activity of 20(S)-Camptothecin Derivatives. A-Ring-Substituted 7-Ethylcamptothecins and their E-Ring-Modified Water-Soluble Derivatives,” Yaegashi et al., Chemical & Pharmaceutical Bulletin. vol. 42. No. 12: 2518-2525 (1994).
“Chemical Modification of an Antitumor Camptothecin: Synthesis and Antitumor Activity of 7-C-Substituted Camptothecins,” Sawada et al., Chemical & Pharmaceutical Bulletin. vol. 39. No. 10: 2574-2580 (1991).
“Synthesis and Antitumor Activity of A-Ring or E-Lactone Modified Water-Soluble Prodrugs of 20(S)-Camptothecin, Including Development of Irinotecan Hydrochloride Trihydrate,” Sawada et al., Current Pharmaceutical Design, vol. 1 No. 1: 113-132 (1995).
Photodegradation reactions of CPT-II, a derivative of camptothecin. I: chemical structure of main degradation products in an aqueous solution, Akimoto et al., Drug Stability. vol. 1 No. 2.: 118-122.
“An Efficient Conversion of Camptothecin to 10-Hydroxycamptothecin, ” Wood et al., The Journal of Organic Chemistry, vol. 60. No. 17: 5739-5740 (1995).
“Synthesis and Antitumor Activity of 20(S)-Camptothecin Derivatives: Carbamate-Linked, Water-Soluble Derivatives of 7-Ethyl-10-hydroxycamptothecin,” Sawada et al., Chemical & Pharmaceutical Bulletin, vol. 39. No. 6 1446-1454 (1991).
“Synthesis and Antitumor Activity of 20(S)-Camptothecin Derivatives: A-Ring Modified and 7, 10-Disubstituted Camptothecins,” Sawada et al., Chemical & Pharmaceutical Bulletin, vol. 39. No. 12: 3183-3188 (1991).

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