Title:
SULFUR-CONTAINING NAPHTHOYLIMIDE DERIVATIVES
Document Type and Number:
WIPO Patent Application WO/2004/101570
Kind Code:
A1
Abstract:
The present invention relates to sulfur-containing naphthoylimide derivatives, the preparation and the use thereof. By expanding the conjugate plane of the naphthoylimide with condensed 5- or 6-member aromatic heterocyclic ring and / or introducing a sulfur atom, the antineoplastic activity of the compounds is improved. For inhibition of the proliferation of tumor-cells from different origins, such as lung cancer, carcinoma ventriculi, liver cancer and leucaemia in human beings, the compounds show remarkable effects with clear quantity-effect relationships.
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Inventors:
QIAN XUHONG (CN)
LI YONGGANG (CN)
XU YUFANG (CN)
DING JIAN (CN)
LIN LIPING (CN)
MIAO ZEHONG (CN)
ZHU HONG (CN)
QU BAOYUAN (CN)
LI YONGGANG (CN)
XU YUFANG (CN)
DING JIAN (CN)
LIN LIPING (CN)
MIAO ZEHONG (CN)
ZHU HONG (CN)
QU BAOYUAN (CN)
Application Number:
PCT/CN2004/000442
Publication Date:
November 25, 2004
Filing Date:
April 30, 2004
Export Citation:
Assignee:
UNIV EAST CHINA SCIENCE & TECH (CN)
SHANGHAI INST MATERIA MEDICA (CN)
UNIV DALIAN TECH (CN)
QIAN XUHONG (CN)
LI YONGGANG (CN)
XU YUFANG (CN)
DING JIAN (CN)
LIN LIPING (CN)
MIAO ZEHONG (CN)
ZHU HONG (CN)
QU BAOYUAN (CN)
SHANGHAI INST MATERIA MEDICA (CN)
UNIV DALIAN TECH (CN)
QIAN XUHONG (CN)
LI YONGGANG (CN)
XU YUFANG (CN)
DING JIAN (CN)
LIN LIPING (CN)
MIAO ZEHONG (CN)
ZHU HONG (CN)
QU BAOYUAN (CN)
International Classes:
A61K31/473; A61K31/4743; A61K31/4745; A61P35/00; C07D221/06; C07D221/14; C07D405/12; C07D495/06; C07D513/06; (IPC1-7): C07D495/06; C07D513/06; C07D221/06; A61K31/473; A61K31/4743; A61K31/4745; A61P35/00
Foreign References:
| JPS60221403A | 1985-11-06 | |||
| US3888863A | 1975-06-10 | |||
| US4254109A | 1981-03-03 |
Other References:
QIAN X., YAO W. ET AL.: "N-(Aroyloxy)naphthalimides as novel higly efficient...", TETRAHEDRON LETTERS, vol. 42, no. 35, 2001, pages 6175 - 6178, XP004293284
YAO W. ET AL.: "Novel and highly efficient DNA photocleavers:...", TETRAHEDRON LETTERS, vol. 41, no. 40, 2000, pages 7711 - 7715, XP004217734
HUANG TIAN-BAO ET AL.: "General synthesis of thioxo-1,8-naphthalimides via thioxo-1,8-naphthalenic anhydrides", SYNTHESIS, no. 7, 1999, pages 1109 - 1111, XP008095051
ZHANG JIANFENG ET AL.: "Synthesis and characterization of thiono-1,8-naphthalimidesthiono-1,8-naphthalimides", HUADONG LIGONG DAXUE XUEBAO, vol. 25, no. 2, 1999, pages 215 - 216,201, XP009093640
QIAN XUHONG, MAO PING ET AL.: "Synthesis and properties of benzothioxanthene dicarboximide hydroperoxide:...", TETRAHEDRON LETTERS, vol. 43, no. 16, 2002, pages 2995 - 2998, XP004345947
XU YUFANG, QIAN XUHONG ET AL.: "Novel naphthalimide hydroperoxide photonucleases:...", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 111, no. 24, 2003, pages 5427 - 5433, XP008092142
MAO PING, QIAN XUHONG ET AL.: "Benzothioxanthene dyes as fluorescent label...", DYES AND PIGMENTS, vol. 60, no. 1, 2003, pages 9 - 16, XP004462942
TONG JIAND-DONG ET AL.: "Use of a dye-labeled ethylene-butene copolymer as a tracer in laser...", JOURNAL OF POLYMER SCIENCE, PART A: POLYMER CHEMISTRY, vol. 39, no. 1, 2000, pages 239 - 252, XP008092328
LI YONGGANG ET AL.: "Naphthalimide-thiazoles as novel photonucleases: molecular design,...", TETRAHEDRON LETTERS, vol. 45, no. 6, 2004, pages 1247 - 1251, XP004484824
BRANA MIGUEL F. ET AL.: "New analogues of amonafide and alinafide, containing aromatic...", JOURNAL OF MEDICINAL CHEMISTRY, vol. 47, no. 6, 2004, pages 1391 - 1399, XP002435350
LI YONGGANG ET AL.: "Thiadizole: A new family of inetrcalative photonuclease with...", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 13, no. 20, 2003, pages 3513 - 3515, XP008092143
PETERS A.T., BIDE M.J.: "Intermediates and dyes for synthetic-polymer fibers...", DYES AND PIGMENTS, vol. 6, no. 4, 1985, pages 267 - 275, XP008092651
PATSENKER LEONID D. ET AL.: "Molecular strucutre and spectral properties of thionaphthalimides", JOURNAL OF MOLECULAR STRUCTURE, vol. 655, no. 2, 2003, pages 311 - 320, XP008092213
ORZESZKO A. ET AL.: "Investigation of the thionation reaction of cyclic imides", ZEITSCHRIFT FUER NATURFORSCHUNG, B: CHEMICAL SCIENCES, vol. 56, no. 10, 2001, pages 1035 - 1040, XP008095113
TETRAHEDRON, vol. 43, 2002, pages 2995 - 2998
J.SOC. DYERS COLOURISTS, vol. 90, 1974, pages 153
See also references of EP 1626050A4
YAO W. ET AL.: "Novel and highly efficient DNA photocleavers:...", TETRAHEDRON LETTERS, vol. 41, no. 40, 2000, pages 7711 - 7715, XP004217734
HUANG TIAN-BAO ET AL.: "General synthesis of thioxo-1,8-naphthalimides via thioxo-1,8-naphthalenic anhydrides", SYNTHESIS, no. 7, 1999, pages 1109 - 1111, XP008095051
ZHANG JIANFENG ET AL.: "Synthesis and characterization of thiono-1,8-naphthalimidesthiono-1,8-naphthalimides", HUADONG LIGONG DAXUE XUEBAO, vol. 25, no. 2, 1999, pages 215 - 216,201, XP009093640
QIAN XUHONG, MAO PING ET AL.: "Synthesis and properties of benzothioxanthene dicarboximide hydroperoxide:...", TETRAHEDRON LETTERS, vol. 43, no. 16, 2002, pages 2995 - 2998, XP004345947
XU YUFANG, QIAN XUHONG ET AL.: "Novel naphthalimide hydroperoxide photonucleases:...", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 111, no. 24, 2003, pages 5427 - 5433, XP008092142
MAO PING, QIAN XUHONG ET AL.: "Benzothioxanthene dyes as fluorescent label...", DYES AND PIGMENTS, vol. 60, no. 1, 2003, pages 9 - 16, XP004462942
TONG JIAND-DONG ET AL.: "Use of a dye-labeled ethylene-butene copolymer as a tracer in laser...", JOURNAL OF POLYMER SCIENCE, PART A: POLYMER CHEMISTRY, vol. 39, no. 1, 2000, pages 239 - 252, XP008092328
LI YONGGANG ET AL.: "Naphthalimide-thiazoles as novel photonucleases: molecular design,...", TETRAHEDRON LETTERS, vol. 45, no. 6, 2004, pages 1247 - 1251, XP004484824
BRANA MIGUEL F. ET AL.: "New analogues of amonafide and alinafide, containing aromatic...", JOURNAL OF MEDICINAL CHEMISTRY, vol. 47, no. 6, 2004, pages 1391 - 1399, XP002435350
LI YONGGANG ET AL.: "Thiadizole: A new family of inetrcalative photonuclease with...", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 13, no. 20, 2003, pages 3513 - 3515, XP008092143
PETERS A.T., BIDE M.J.: "Intermediates and dyes for synthetic-polymer fibers...", DYES AND PIGMENTS, vol. 6, no. 4, 1985, pages 267 - 275, XP008092651
PATSENKER LEONID D. ET AL.: "Molecular strucutre and spectral properties of thionaphthalimides", JOURNAL OF MOLECULAR STRUCTURE, vol. 655, no. 2, 2003, pages 311 - 320, XP008092213
ORZESZKO A. ET AL.: "Investigation of the thionation reaction of cyclic imides", ZEITSCHRIFT FUER NATURFORSCHUNG, B: CHEMICAL SCIENCES, vol. 56, no. 10, 2001, pages 1035 - 1040, XP008095113
TETRAHEDRON, vol. 43, 2002, pages 2995 - 2998
J.SOC. DYERS COLOURISTS, vol. 90, 1974, pages 153
See also references of EP 1626050A4
Attorney, Agent or Firm:
SHANGHAI PATENT & TRADEMARK LAW OFFICE (435 Guiping Road, Shanghai 3, CN)
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