Title:
NOVEL TYLOINDICINES AND RELATED PROCESSES, PHARMACEUTICAL COMPOSITIONS AND METHODS
Document Type and Number:
WIPO Patent Application WO2003070166
Kind Code:
A3
Abstract:
The invention provides novel tyloindicines analogues and related processes, pharmaceutical compositions, and methods. The novel tyloindicines are useful in a wide variety of antiviral, antineoplastic, antibacterial, and anti-inflammatory applications. Preferred embodiments of the instant invention include the novel tyloindicine designated herein as compound IT-3 (NSC-716802). Compounds of the instant invention have exhibited potent antiviral and anticancer activity in vitro. The invention further provides novel methods of treating neoplastic, bacterial, viral, and anti-inflammatory disorders using tyloindicines including the novel tyloindicine analogues of the instant invention. The invention also provides novel syntheses of tyloindicines including the novel tyloindicines analogues of the instant invention.
Inventors:
BAKER DAVID C (US)
CHENG YUNG-CHI (US)
ZHONG SANBAO (US)
CHENG YUNG-CHI (US)
ZHONG SANBAO (US)
Application Number:
PCT/US2003/004072
Publication Date:
January 08, 2004
Filing Date:
February 12, 2003
Export Citation:
Assignee:
UNIV YALE (US)
UNIV TENNESSEE RES CORP (US)
BAKER DAVID C (US)
CHENG YUNG-CHI (US)
ZHONG SANBAO (US)
UNIV TENNESSEE RES CORP (US)
BAKER DAVID C (US)
CHENG YUNG-CHI (US)
ZHONG SANBAO (US)
International Classes:
A61K31/437; A61K31/4745; A61P1/04; A61P3/10; A61P7/02; A61P9/10; A61P9/14; A61P11/00; A61P11/06; A61P11/16; A61P13/12; A61P17/00; A61P17/02; A61P17/06; A61P19/02; A61P25/28; A61P29/00; A61P31/04; A61P31/18; A61P31/20; A61P35/00; A61P35/02; A61P37/00; A61P37/06; A61P37/08; A61P43/00; C07B61/00; C07D455/02; C07D455/03; C07D471/04; C07F7/02; C07F7/18; (IPC1-7): A61K31/437; A61K31/4375; A61K31/4745; A61K31/55; A61P29/00; A61P35/00; A61P37/00; C07D455/03; C07D471/04
Other References:
TRIGO ET AL.: "Contribution to the synthesis of cryptopleurine and related phenanthroquinolizidines", J. HETEROCYCLIC CHEM., vol. 17, January 1980 (1980-01-01), pages 69 - 72, XP002969139
PATON ET AL.: "Cryptopleurine, a synthesis based on biogenetic considerations", J. CHEM. SOC. (C), vol. 10, 1969, pages 1309 - 1314, XP002969140
PETTIT ET AL.: "Antineoplastic agents, 103. The isolation and structure of hypoestestatins 1 and 2 from the East African hyposets verticillaris", J. NATURAL PRODUCTS, vol. 47, no. 6, November 1984 (1984-11-01) - December 1984 (1984-12-01), pages 913 - 919, XP002969141
LIEPA ET AL.: "An improved phenanthrene synthesis: a simple route to tylophorine", J.C.S. CHEM. COMM., vol. 22, 1977, pages 826 - 827, XP002106485
OHYAMA ET AL.: "Cytotoxic phenanthroinolizidine alkaloids in tylophora tanakae against human gastric carcinoma cells", PROC. JAPAN ACAD. SER. B., vol. 76B, no. 10, 2000, pages 161 - 165, XP002969142
SAIFAH ET AL.: "Constituents of the leaves of cissus rheifolia", J. NATURAL PRODUCTS, vol. 46, no. 3, May 1983 (1983-05-01) - June 1983 (1983-06-01), pages 353 - 358, XP002969143
KRMPOTIC ET AL.: "Cryptopleurine, an active antiviral alkaloid from boehmeria cylindrica (L.)Sw.(urticaceae)", JOURNAL OF PHARMACEUTICAL SCIENCES, vol. 61, no. 9, September 1972 (1972-09-01), pages 1508 - 1509, XP002969144
See also references of EP 1482937A4
PATON ET AL.: "Cryptopleurine, a synthesis based on biogenetic considerations", J. CHEM. SOC. (C), vol. 10, 1969, pages 1309 - 1314, XP002969140
PETTIT ET AL.: "Antineoplastic agents, 103. The isolation and structure of hypoestestatins 1 and 2 from the East African hyposets verticillaris", J. NATURAL PRODUCTS, vol. 47, no. 6, November 1984 (1984-11-01) - December 1984 (1984-12-01), pages 913 - 919, XP002969141
LIEPA ET AL.: "An improved phenanthrene synthesis: a simple route to tylophorine", J.C.S. CHEM. COMM., vol. 22, 1977, pages 826 - 827, XP002106485
OHYAMA ET AL.: "Cytotoxic phenanthroinolizidine alkaloids in tylophora tanakae against human gastric carcinoma cells", PROC. JAPAN ACAD. SER. B., vol. 76B, no. 10, 2000, pages 161 - 165, XP002969142
SAIFAH ET AL.: "Constituents of the leaves of cissus rheifolia", J. NATURAL PRODUCTS, vol. 46, no. 3, May 1983 (1983-05-01) - June 1983 (1983-06-01), pages 353 - 358, XP002969143
KRMPOTIC ET AL.: "Cryptopleurine, an active antiviral alkaloid from boehmeria cylindrica (L.)Sw.(urticaceae)", JOURNAL OF PHARMACEUTICAL SCIENCES, vol. 61, no. 9, September 1972 (1972-09-01), pages 1508 - 1509, XP002969144
See also references of EP 1482937A4
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