Organic compounds -- part of the class 532-570 series – Organic compounds – Cyclopentanohydrophenanthrene ring system containing
Reexamination Certificate
2005-05-03
2005-05-03
Qazi, Sabiha (Department: 1616)
Organic compounds -- part of the class 532-570 series
Organic compounds
Cyclopentanohydrophenanthrene ring system containing
C552S540000, C536S005000, C514S169000, C514S171000, C514S180000
Reexamination Certificate
active
06888014
ABSTRACT:
This invention relates to a group of novel sapogenins, their use in anti-cancer applications, and to a process for their production. More particularly, this invention pertains to a novel group of dammarane sapogenins, PAM-120, PBM-110 and PBM-100 (the dammarance sapogenine structure is specifically clean of any sugar moieties (glycons) at any position and hydroxyl at C-20) and PAN-20 and PAN-30 (the dammarance sapogenin structure has sugar moieties but is free of hydroxyl at C-20), obtained by chemical cleavage of dammarane saponins. The invention also includes a novel application of the said sapogenins for anti-cancer treatment by using them separately or together, and/or jointly with other drugs, as well as to the process of producing these novel sapogenins. Said novel dammarane sapogenins show surprising anti-cancer effect when applied, particularly against multi-drug resistant cancers.
REFERENCES:
patent: 4157894 (1979-06-01), Bombardelli
patent: 4621137 (1986-11-01), Miyake et al.
patent: 4966893 (1990-10-01), Pang et al.
patent: 5850032 (1998-12-01), Wann
patent: 5919770 (1999-07-01), Hideo et al.
patent: 8-208688 (1996-08-01), None
patent: 11-295310 (1999-10-01), None
patent: WO97/31933 (1997-09-01), None
Shibata, Shoji et al.; Chemical and Pharmaceutical Bulletin (1966), 14(6), 595-600.*
Jianbiao et al. (DN 120:279955, abstract of Lizi Jiaohuan Yu Xifu (1993), 9(2), 97-101).*
Y.S. Kim, et al., Ginsenoside Rh2 and Rh3 induce differentiation of HL-60 cells into granulo-cytes: modulation of protein kinase C isoforms during differentiation by ginseoside Rh2,The International Journal of Biochemistry&Cell Biology30 (1998) 327-338.
A.S. Attele, et al., Ginseng Pharmacology: Multiple Constituents and Multiple Actions,Biochemical Pharmacology,vol. 58, pp. 1685-1693, 1999.
H. Hasegawa, et al., Reversal of Daunomycin and Vinblastine Resistance in Multidrug-Resistant P388 Leukemia in vitro through Enhanced Cytotoxicity by Triterpenoids,Planta Med.61 (1995) 409-413.
www.herbmed.org/herbs/panax.htm, Alternative Medicine Foundation—information regarding ginseng.
Abstract—Y.N. Lee, et al., In vitro induction of differentiation by ginsenoides in F9 tetratocarcinoma cells,Eur. J. CancerJul. 1996; 32A(8):1420-8.
Abstract—S. Odashima, et al., Control of phenotypic expression of cultured B16 melanoma cells by plant glycosides,Cancer Res.Jun. 1985; 45(6):2781-4.
Abstract—L.J. Xin & R. Han, [Differentiation of B16 melanoma cells induced by ginsenoside RH2],Yao Hsueh Hsueh Pao1996;31(10):742-5.
Abstract—Y. Kikuchi, et al., Inhibitors of human ovarian cancer cell proliferation in vitro by ginsenoside Rh2 and adjuvant effects to cisplatin in vivo,Anticancer DrugsFeb. 1991; 2(1):63-7.
Abstract—K.Y. Lee, et al., Ginsenoside-Rh2 blocks the cell cycle of SK-HEP-1 cells at the G1/S boundary by selectively inducing the protein expression of p27kip1,Cancer Lett.Dec. 20, 1996; 110(1-2):193-200.
Abstract—M. Oh, et al., Anti-proliferating effects of ginsenoside Rh2 on MCF-7 human breast cancer cells,Int. J. Oncol.May 1999; 14(5):869-75.
Abstract—T. Ota, et al., G1 phase-specific suppression of the Cdk2 activity by ginsenoside Rh2 in cultured murine cells,Life Sci.1997; 60(2):PL39-44.
Abstract—H. Nakata, et al., Inhibitory effects of ginsenoside Rh2 on tumor growth in nude mice bearing human ovarian cancer cells,Jpn. J. Cancer Res.Jul. 1998; 89(7):733-40.
Abstract—H.E. Kim, et al., Ginsenoside RH-2 induces apoptotic cell death in rat C6 glioma via a reactive oxygen- and caspase-dependent but Bcl-X(L)-independent pathway,Life Sci.1999; 65(3):PL33-40.
Abstract—J.A. Park, et al., Activation of caspase-3 protease via a Bcl-2-insensitive pathway during the process of ginsenoside Rh2-induced apoptosis,Canc. Lett.Dec. 16, 1997: 121(1):73-81.
Abstract—K. Shinkai, et al., Inhibition of in vitro tumor cell invasion by ginsensoside Rg3,Jpn. J. Cancer Res.Apr. 1996 87(4):357-62.
Abstract—H. Iishi, et al., Inhibition by ginsenoside Rg3 of bombesin-enhanced peritoneal metastasis on intestinal adenocarcinomas induced by azoxymethane in Wistar rats,Clin. Exp. MetastasisNov. 1997; 15(6):603-11.
Abstract—M. Mochizuki et a., Inhibitory effect of tumor metastasis in mice by saponins, ginsenoside-Rb2, 20(R)-and 20(S)-ginsenoside-Rg3, of red ginseng,Biol. Pharm. Bull.Sep. 1995; 18(9):1197-202.
Abstract—Lee, S.J., et al., Antitumor activity of a novel ginseng saponin metabolite in human pulmonary adenocarcinoma cells resistant to cisplatin,Cancer Lett.Sep. 20, 1999; 144(1):39-43.
Abstract—M. Yoshikawa, et al., Bioactive saponins and glycosides. XI. Structures of new dammarane-type triterpene oligoglycosides, quinquenosides I, II, III, IV, and V, from American ginseng, the roots of Panax quinquefolium L.,Chem. Phamr. Bull.(Tokyo) Apr. 1998; 46(4):647-54.
Abstract—A.M. Popov, et al., [Comparative study of anti-tumor activity of the monoglucosides protopanaxadiol and betulafolientriol],Antibiot. KhimioterJul. 1994; 39(7):24-9.
Abstract—T. Kaku et al., Chemico-pharmacological studies on saponins of Panax ginseng C.A. Meyer. II. Pharmacological Part,ArzneimittleforschungApr. 1975; 25(4):539-47.
Abstract—Y.S. Kim, et al., Ginsenoside Rh2 and Rh3 induce differentiation of HL-60 cells into granulocytes:modulation of protein kinase C isoforms during differentiation by ginsenoside Rh2,Int. J. Biochem. Cell BiologyMar. 1998;30(3):327-38.
Abstract—Y. Takino, [Studies on the pharmacodynamics of ginsenoside-Rg1, -Rb1 and -RB2 in rats],Yakugaku ZasshiAug. 1994; 114(8):550-64. (Also list of titles of related articles.).
Abstract—N.M. Duc, et al., Saponins from Vietnamese ginseng, Panax vietnamensis Ha et Grushv. collected in central Vietnam. III.Chem. Pharm. Bull.(Tokyo) Mar. 1994;42(3):634-40.
Abstract—N.I. Baek, et a., Ginsenoside Rh4, a genuine dammarane glycoside from Korean red ginseng.Planta Med.Feb. 1996; 62(1):86-7.
Abstract—M. Yoshikawa, et al., Bioactive saponins and glycosides. VIII. Notoginseng (1): new dammarane-type triterpene oligoglycosides, notoginsensosides-A, -B, -C and -D, from the dried root of Panax notoginseng (Burk.) F.H. Chen.Chem. Pharm. Bull.(Tokyo) Jun. 1997;45(6):1039-45.
Abstract—D. Hou, et al., Separation and determination of chemical constituents in the volatile oil of three traditional Chinese crude drugs,J. Pharm. Biomed. Anal.Sep. 1998;17(8):1423-6.
Abstract—J.P. Hou, The chemical constituents of ginseng plants,Comp. Med. East West1977 Summer;5(2):123-45.
Absract—J.F. Cui, et al., Gas chromatographic-mass spectrometric determination of 20(S)-protopanaxadiol and 20(S)-protopanaxatriol for study on human urinary excretion of ginsenosides after ingestion of ginseng preparations,J. Chromatogr. B. Biomed. Sci. App.Feb. 21, 1997;689(2):349-55.
Abstract—J.F. Cui, et al., Analysis of ginsenosides by chromatography and mass spectrometry: release of 20 S-protopanaxadiol and 20 S-protopanaxatriol for quantitation,Anal. Biochem.May 1, 1993;210(2):411-7.
Absract—T. Ota, et al., Mechanism of action of ginsenoside Rh2: uptake and metabolism of ginsenoside Rh2 by cultured B16 melanoma cells,J. Pharm. Sci.Dec. 1991; 80(12):1141-6.
Abstract—C. Wakabayashi, et al., An intestinal bacerial metabolite of ginseng protopanaxadiol saponins has the ability to induce apoptosis in tumor cells,Biochem. Biophys. Res. Commun.May 29, 1998; 246(3):725-30.
Abstract—C. Wakabayashi, et al., In vivo antimetastic action of ginseng protopanaxadiol saponins is based on their intestinal bacterial metabolites after oral administration.Oncol. Res.1997;9(8):411-7.
Abstract—S.J. Lee, et al., Antitumor activity of a novel ginseng saponin metabolite in human pulmonary adenocarcinoma cells resistant to cisplatin,Cancer Lett.Sep. 20, 1999; 144(1):39-43.
Abstract—H. Hasegawa & M. Uchiyama, Antimetastatic efficacy of orally administered ginsenoside Rb1 in dependence on intestinal bacterial hydrolyzing potential and signific
Huang Dong
Qi Dong Feng
PanaGin Pharmaceuticals Inc.
Qazi Sabiha
Synnestvedt & Lechner LLP
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