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    • 1. 发明授权
    • Treatment of breast cancer
    • 乳腺癌的治疗
    • US06703426B1
    • 2004-03-09
    • US10309536
    • 2002-12-04
    • D. Howard MilesSolodnikov Sergey YurjevichKrasnykh Olga PetrovnaPimenova Elena ValentinovnaElena A. Goun
    • D. Howard MilesSolodnikov Sergey YurjevichKrasnykh Olga PetrovnaPimenova Elena ValentinovnaElena A. Goun
    • A61K3116
    • C07D231/28C07C59/90C07C251/84C07C251/86C07D207/38
    • Compounds of the class of 4-oxo-butenoic acid derivatives are disclosed along with the surprising use property of these compounds as a anti-tumor agents in humans against breast carcinoma, which include: 2-(N′-Fluoren-9-ylidene-hydrazino)5,5-dimethyl-4-oxo-hex-2-enoic acid methyl ester (OF-06), 1-(2,4-Dimethyl-phenyl)-2,4-dihydroxy-3-(4-methyl-benzoyl)-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylic acid methyl ester (1F-07), 4-(4-Methoxy-phenyl)-2,4-dioxo-3-(phenyl-hydrazono)-butyric acid (3F-10), 4-(4-Chloro-phenyl)-2,4-dioxo-3-(phenyl-hydrazono)-butyric acid ethyl ester (3F-11), 2-Hydroxy-4-oxo-4-(2,3,5,6-tetrafluoro-4-methoxy-phenyl)-but-2-enoic acid (3F-15), and 4,4-Dihydroxy-5-(4-methyl-benzoyl)-2-phenyl-2,4-dihydro-pyrazol-3-one (3F-16) as well as some novel derivatives of these compounds claimed (see Table 2). The invention also encompasses a class of the compounds with the novel property of anti-tumor activity against human breast cancer, which includes the following compounds 4-(4-Ethoxy-phenyl)-2-(N′-fluoren-9-ylidene-hydrazino)-2-hydroxy-4-oxo-butyric acid methyl ester (OF-13); 2-{N′-[1-(4-Chloro-phenyl)-ethylidene]-hydrazino}-4-oxo-4-phenyl-but-2-enoic acid methyl ester (OF-20); 2-(N′-Fluoren-9-ylidene-hydrazino)-4-oxo-4-phenyl-but-2-enoic acid methyl ester (1F-04); and 4-Chloro-4-(4-ethoxy-phenyl)-2-(fluoren-9-ylidene-hydrazono)-but-3-enoic acid methyl ester (3F-19).
    • 公开了4-氧代 - 丁烯酸衍生物类的化合物以及这些化合物作为抗人肿瘤药物在乳腺癌中的惊人使用性质,其包括:2-(N'-芴-9-亚基 - 肼基)5,5-二甲基-4-氧代 - 己-2-烯酸甲酯(OF-06),1-(2,4-二甲基 - 苯基)-2,4-二羟基-3-(4-甲基 - 苯甲酰基)-5-氧代-2,5-二氢-1H-吡咯-2-甲酸甲酯(1F-07),4-(4-甲氧基 - 苯基)-2,4-二氧代-3-(苯基 - 亚肼基) - 丁酸(3F-10),4-(4-氯 - 苯基)-2,4-二氧代-3-(苯基 - 亚氨基) - 丁酸乙酯(3F-11),2-羟基 - 4-氧代-4-(2,3,5,6-四氟-4-甲氧基 - 苯基) - 丁-2-烯酸(3F-15)和4,4-二羟基-5-(4-甲基 - 苯甲酰基)-2-苯基-2,4-二氢 - 吡唑-3-酮(3F-16)以及这些化合物的一些新型衍生物(见表2)。 本发明还包括一类具有抗人乳腺癌抗肿瘤活性的新性质的化合物,其包括以下化合物4-(4-乙氧基 - 苯基)-2-(N'-芴-9-亚基 - 肼基)-2-羟基-4-氧代 - 丁酸甲酯(OF-13); 2- {N' - [1-(4-氯 - 苯基) - 亚乙基] - 肼基} -4-氧代-4-苯基 - 丁-2-烯酸甲酯(OF-20); 2-(N'-芴-9-亚基 - 肼基)-4-氧代-4-苯基 - 丁-2-烯酸甲酯(1F-04); 和4-氯-4-(4-乙氧基 - 苯基)-2-(芴-9-亚基 - 亚氨基) - 丁-3-烯酸甲酯(3F-19)。
    • 2. 发明授权
    • Treatment of breast cancer
    • 乳腺癌的治疗
    • US06602907B1
    • 2003-08-05
    • US10164541
    • 2002-06-07
    • Howard MilesSolodnikov Sergey YurjevichKrasnykh Olga PetrovnaPimenova Elena ValentinovnaElena A. Goun
    • Howard MilesSolodnikov Sergey YurjevichKrasnykh Olga PetrovnaPimenova Elena ValentinovnaElena A. Goun
    • A61K31277
    • C07D231/28C07C59/90C07C251/84C07C251/86C07D207/38
    • Compounds of the class of 4-oxo-butenoic acid derivatives are disclosed along with the surprising use property of these compounds as a anti-tumor agents in humans against breast carcinoma, which include: 2-(N′-Fluoren-9-ylidene-hydrazino)-5,5-dimethyl-4-oxo-hex-2-enoic acid methyl ester (0F-06), 1-(2,4-Dimethyl-phenyl)-2,4-dihydroxy-3-(4-methyl-benzoyl)-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylic acid methyl ester (1F-07), 4-(4-Methoxy-phenyl)-2,4-dioxo-3-(phenyl-hydrazono)-butyric acid (3F-10), 4-(4-Chloro-phenyl)-2,4-dioxo-3-(phenyl-hydrazono)-butyric acid ethyl ester (3F-11), 2-Hydroxy-4-oxo-4-(2,3,5,6-tetrafluoro-4-methoxy-phenyl)-but-2-enoic acid (3F-15), and 4,4-Dihydroxy-5-(4-methyl-benzoyl)-2-phenyl-2,4-dihydro-pyrazol-3-one (3F-16) as well as some novel derivatives of these compounds claimed (see Table 2). The invention also encompasses a class of the compounds with the novel property of anti-tumor activity against human breast cancer, which includes the following compounds 4-(4-Ethoxy-phenyl)-2-(N′-fluoren-9-ylidene-hydrazino)-2-hydroxy-4-oxo-butyric acid methyl ester (0F-13); 2-{N′-[1-(4-Chloro-phenyl)-ethylidene]-hydrazino}-4-oxo-4-phenyl-but-2-enoic acid methyl ester (0F-20); 2-(N′-Fluoren-9-ylidene-hydrazino)-4-oxo-4-phenyl-but-2-enoic acid methyl ester (1F-04); and 4-Chloro-4-(4-ethoxy-phenyl)-2-(fluoren-9-ylidene-hydrazono)-but-3-enoic acid methyl ester (3F-19).
    • 公开了4-氧代 - 丁烯酸衍生物类的化合物以及这些化合物作为抗人肿瘤药物在乳腺癌中的惊人使用性质,其包括:2-(N'-芴-9-亚基 - 肼基)-5,5-二甲基-4-氧代 - 己-2-烯酸甲酯(0F-06),1-(2,4-二甲基 - 苯基)-2,4-二羟基-3-(4- 甲基 - 苯甲酰基)-5-氧代-2,5-二氢-1H-吡咯-2-甲酸甲酯(1F-07),4-(4-甲氧基 - 苯基)-2,4-二氧代-3-( 苯基 - 亚肼基) - 丁酸(3F-10),4-(4-氯 - 苯基)-2,4-二氧代-3-(苯基 - 亚氨基) - 丁酸乙酯(3F-11),2-羟基 -4-氧代-4-(2,3,5,6-四氟-4-甲氧基 - 苯基) - 丁-2-烯酸(3F-15)和4,4-二羟基-5-(4-甲基 - 苯甲酰基)-2-苯基-2,4-二氢 - 吡唑-3-酮(3F-16)以及这些化合物的一些新型衍生物(参见表2)。 本发明还包括一类具有抗人乳腺癌抗肿瘤活性的新性质的化合物,其包括以下化合物4-(4-乙氧基 - 苯基)-2-(N'-芴-9-亚基 - 肼基)-2-羟基-4-氧代 - 丁酸甲酯(0F-13); 2- {N' - [1-(4-氯 - 苯基) - 亚乙基] - 肼基} -4-氧代-4-苯基 - 丁-2-烯酸甲酯(0F-20); 2-(N'-芴-9-亚基 - 肼基)-4-氧代-4-苯基 - 丁-2-烯酸甲酯(1F-04); 和4-氯-4-(4-乙氧基 - 苯基)-2-(芴-9-亚基 - 亚氨基) - 丁-3-烯酸甲酯(3F-19)。
    • 5. 发明授权
    • Treatment of myeloma
    • 治疗骨髓瘤
    • US06686496B1
    • 2004-02-03
    • US10165027
    • 2002-06-07
    • D. Howard MilesSolodnikov Sergey YurjevichKrasnykh Olga PetrovnaKorotkova Tatiana AlexandrovnaElena A. Goun
    • D. Howard MilesSolodnikov Sergey YurjevichKrasnykh Olga PetrovnaKorotkova Tatiana AlexandrovnaElena A. Goun
    • C07C20500
    • C07C251/84
    • The compounds of the invention which encompasses a class of compounds having the property of anti-carcinogenic activity against human myeloma r comprising 4-oxo-2-butenoic acid compounds and 3-hydrazino-2,4-dioxobutanoic acid compounds and more specifically those novel derivatives: 4-(4-Chloro-phenyl)-2-(N′-fluoren-9-ylidene-hydrazino)-4-oxo-but-2-enoic acid methyl ester (OF-07); 2-{N′-[(2-Bromo-phenyl)-phenyl-methylene]-hydrazino}-4-oxo-4-phenyl-but-2-enoic acid methyl ester (OF-09); 2-{N′-[(4-Dimethylamino-phenyl)-phenyl-methylene]-hydrazino}-4-oxo-4-phenyl-but-2-enoic acid methyl ester (OF-10) and 2-{N′-[1-(4-Chloro-phenyl)-ethylidene]-hydrazino}-4-oxo-4-phenyl-but-2-enoic acid methyl ester (OF-20) and the use of 2-(N′-Fluoren-9-ylidene-hydrazino)-5,5-dimethyl-4-oxo-hex-2-enoic acid methyl ester (OF-06); 4-(4-Ethoxy-phenyl)-2-(N′-fluoren-9-ylidene-hydrazino)-2-hydroxy-4-oxo-butyric acid methyl ester (OF-13); 4-benzoyl-3 -benzoyloxy-2-(2-oxo-2H-1,4-benzoxazin-3-yl)pyrido[2,1-c][1,4]benzoxazin-1,5-dione (1F-18), 4-Chloro-4-(4-ethoxy-phenyl)-2-(fluoren-9-ylidene-hydrazono)-but-3-enoic acid methyl ester (3F-19); and 2-(N′-Fluoren-9-ylidene-hydrazino)-4-oxo-4-phenyl-but-2-enoic acid methyl ester (1F-04) which are unique in humans as therapeutic means for the eradication human myeloma.
    • 本发明的化合物包括一类具有抗人类骨髓瘤抗癌活性的化合物,其包含4-氧代-2-丁烯酸化合物和3-肼基-2,4-二氧代丁酸化合物,更具体地说是那些新颖的 衍生物:4-(4-氯 - 苯基)-2-(N'-芴-9-亚基 - 肼基)-4-氧代 - 丁-2-烯酸甲酯(OF-07); 2- {N' - [(2-溴 - 苯基) - 苯基 - 亚甲基] - 肼基} -4-氧代-4-苯基 - 丁-2-烯酸甲酯(OF-09); 2- {N' - [(4-二甲基氨基 - 苯基) - 苯基 - 亚甲基] - 肼基} -4-氧代-4-苯基 - 丁-2-烯酸甲酯(OF-10)和2- { - [1-(4-氯 - 苯基) - 亚乙基] - 肼基} -4-氧代-4-苯基 - 丁-2-烯酸甲酯(OF-20)和使用2-(N'-Fluoren -9-亚基 - 肼基)-5,5-二甲基-4-氧代 - 己-2-烯酸甲酯(OF-06); 4-(4-乙氧基 - 苯基)-2-(N'-芴-9-亚基 - 肼基)-2-羟基-4-氧代 - 丁酸甲酯(OF-13); 4-苯甲酰基-3-苯甲酰氧基-2-(2-氧代-2H-1,4-苯并恶嗪-3-基)吡啶并[2,1-c] [1,4]苯并恶嗪-1,5-二酮(1F- 18),4-氯-4-(4-乙氧基 - 苯基)-2-(芴-9-亚基 - 亚氨基) - 丁-3-烯酸甲酯(3F-19); 和2-(N'-芴-9-亚基 - 肼基)-4-氧代-4-苯基 - 丁-2-烯酸甲酯(1F-04),其在人中是独特的,作为根除人骨髓瘤的治疗手段 。
    • 6. 发明授权
    • Treatment of breast cancer
    • 乳腺癌的治疗
    • US06638975B1
    • 2003-10-28
    • US10309619
    • 2002-12-04
    • D. Howard MilesSolodnikov Sergey YurjevichKrasnykh Olga PetrovnaPimenova Elena ValentinovnaElena A. Goun
    • D. Howard MilesSolodnikov Sergey YurjevichKrasnykh Olga PetrovnaPimenova Elena ValentinovnaElena A. Goun
    • A61K31216
    • C07D231/28C07C59/90C07C251/84C07C251/86C07D207/38
    • Compounds of the class of 4-oxo-butenoic acid derivatives are disclosed along with the surprising use property of these compounds as a anti-tumor agents in humans against breast carcinoma, which include: 2-(N′-Fluoren-9-ylidene-hydrazino)-5,5-dimethyl-4-oxo-hex-2-enoic acid methyl ester (OF-06), 1-(2,4-Dimethyl-phenyl)-2,4-dihydroxy-3-(4-methyl-benzoyl)-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylic acid methyl ester (1F-07), 4-(4-Methoxy-phenyl)-2,4-dioxo-3-(phenyl-hydrazono)-butyric acid (3F-10), 4-(4-Chloro-phenyl)-2,4-dioxo-3-(phenyl-hydrazono)-butyric acid ethyl ester (3F-11), 2-Hydroxy-4-oxo-4-(2,3,5,6-tetrafluoro-4-methoxy-phenyl)-but-2-enoic acid (3F-15), and 4,4-Dihydroxy-5-(4-methyl-benzoyl)-2-phenyl-2,4-dihydro-pyrazol-3-one (3F-16) as well as some novel derivatives of these compounds claimed (see Table 2). The invention also encompasses a class of the compounds with the novel property of anti-tumor activity against human breast cancer, which includes the following compounds 4-(4-Ethoxy-phenyl)-2-(N′-fluoren-9-ylidene-hydrazino)-2-hydroxy-4-oxo-butyric acid methyl ester (OF-13); 2-{N′-[1-(4-Chloro-phenyl)-ethylidene]-hydrazino}-4-oxo-4-phenyl-but-2-enoic acid methyl ester (OF-20); 2-(N′-Fluoren-9-ylidene-hydrazino)-4-oxo-4-phenyl-but-2-enoic acid methyl ester (1F-04); and 4-Chloro-4-(4-ethoxy-phenyl)-2-(fluoren-9-ylidene-hydrazono)-but-3-enoic acid methyl ester (3F-19).
    • 公开了4-氧代 - 丁烯酸衍生物类的化合物以及这些化合物作为抗人肿瘤药物在乳腺癌中的惊人使用性质,其包括:2-(N'-芴-9-亚基 - 肼基)-5,5-二甲基-4-氧代 - 己-2-烯酸甲酯(OF-06),1-(2,4-二甲基 - 苯基)-2,4-二羟基-3-(4- 甲基 - 苯甲酰基)-5-氧代-2,5-二氢-1H-吡咯-2-甲酸甲酯(1F-07),4-(4-甲氧基 - 苯基)-2,4-二氧代-3-( 苯基 - 亚肼基) - 丁酸(3F-10),4-(4-氯 - 苯基)-2,4-二氧代-3-(苯基 - 亚氨基) - 丁酸乙酯(3F-11),2-羟基 -4-氧代-4-(2,3,5,6-四氟-4-甲氧基 - 苯基) - 丁-2-烯酸(3F-15)和4,4-二羟基-5-(4-甲基 - 苯甲酰基)-2-苯基-2,4-二氢 - 吡唑-3-酮(3F-16)以及这些化合物的一些新型衍生物(参见表2)。 本发明还包括一类具有抗人乳腺癌抗肿瘤活性的新性质的化合物,其包括以下化合物4-(4-乙氧基 - 苯基)-2-(N'-芴-9-亚基 - 肼基)-2-羟基-4-氧代 - 丁酸甲酯(OF-13); 2- {N' - [1-(4-氯 - 苯基) - 亚乙基] - 肼基} -4-氧代-4-苯基 - 丁-2-烯酸甲酯(OF-20); 2-(N'-芴-9-亚基 - 肼基)-4-氧代-4-苯基 - 丁-2-烯酸甲酯(1F-04); 和4-氯-4-(4-乙氧基 - 苯基)-2-(芴-9-亚基 - 亚氨基) - 丁-3-烯酸甲酯(3F-19)。
    • 9. 发明授权
    • Treatment of breast cancer
    • 乳腺癌的治疗
    • US06713503B1
    • 2004-03-30
    • US10309718
    • 2002-12-04
    • D. Howard MilesSolodnikov Sergey YurjevichKrasnykh Olga PetrovnaPimenova Elena ValentinovnaElena A. Goun
    • D. Howard MilesSolodnikov Sergey YurjevichKrasnykh Olga PetrovnaPimenova Elena ValentinovnaElena A. Goun
    • A61K3140
    • C07D231/28C07C59/90C07C251/84C07C251/86C07D207/38
    • Compounds of the class of 4-oxo-butenoic acid derivatives are disclosed along with the surprising use property of these compounds as a anti-tumor agents in humans against breast carcinoma, which include: 2-(N′-Fluoren-9-ylidene-hydrazino)-5,5-dimethyl-4-oxo-hex-2-enoic acid methyl ester (OF-06), 1-(2,4-Dimethyl-phenyl)-2,4-dihydroxy-3-4-methyl-benzoyl)-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylic acid methyl ester (1F-07), 4-(4-Methoxy-phenyl)-2,4-dioxo-3-(phenyl-hydrazono)-butyric acid (3F-10), 4-(4-Chloro-phenyl)-2,4-dioxo-3-(phenyl-hydrazono)-butyric acid ethyl ester (3F-11), 2-Hydroxy-4-oxo-4-(2,3,5,6-tetrafluoro-4-methoxy-phenyl)-but-2-enoic acid (3F-15), and 4,4-Dihydroxy-5-4-methyl-benzoyl)-2-phenyl-2,4-dihydro-pyrazol-3-one (3F-16) as well as some novel derivatives of these compounds claimed (see Table 2). The invention also encompasses a class of the compounds with the novel property of anti-tumor activity against human breast cancer, which includes the following compounds 4-(4-Ethoxy-phenyl)-2-(N′-fluoren-9-ylidene-hydrazino)-2-hydroxy-4-oxo-butyric acid methyl ester (OF-13); 2-{N′-[1-(4-Chloro-phenyl)-ethylidene]-hydrazino}-4-oxo-4-phenyl-but-2-enoic acid methyl ester (OF-20); 2-(N′-Fluoren-9-ylidene-hydrazino)-4-oxo-4-phenyl-but-2-enoic acid methyl ester (1F-04); and 4-Chloro-4-(4-ethoxy-phenyl)-2-(fluoren-9-ylidene-hydrazono)-but-3-enoic acid methyl ester (3F-19).
    • 公开了4-氧代 - 丁烯酸衍生物类的化合物以及这些化合物作为抗人肿瘤药物在乳腺癌中的惊人使用性质,其包括:2-(N'-芴-9-亚基 - 肼基)-5,5-二甲基-4-氧代 - 己-2-烯酸甲酯(OF-06),1-(2,4-二甲基 - 苯基)-2,4-二羟基-3,4-甲基 - 苯甲酰基)-5-氧代-2,5-二氢-1H-吡咯-2-甲酸甲酯(1F-07),4-(4-甲氧基 - 苯基)-2,4-二氧代-3-(苯基 - 亚肼基) - 丁酸(3F-10),4-(4-氯 - 苯基)-2,4-二氧代-3-(苯基 - 亚氨基) - 丁酸乙酯(3F-11),2-羟基 - 4-氧代-4-(2,3,5,6-四氟-4-甲氧基 - 苯基) - 丁-2-烯酸(3F-15)和4,4-二羟基-5-4-甲基 - 苯甲酰基 )-2-苯基-2,4-二氢 - 吡唑-3-酮(3F-16)以及这些化合物的一些新型衍生物(参见表2)。 本发明还包括一类具有抗人乳腺癌抗肿瘤活性的新性质的化合物,其包括以下化合物4-(4-乙氧基 - 苯基)-2-(N'-芴-9-亚基 - 肼基)-2-羟基-4-氧代 - 丁酸甲酯(OF-13); 2- {N' - [1-(4-氯 - 苯基) - 亚乙基] - 肼基} -4-氧代-4-苯基 - 丁-2-烯酸甲酯(OF-20); 2-(N'-芴-9-亚基 - 肼基)-4-氧代-4-苯基 - 丁-2-烯酸甲酯(1F-04); 和4-氯-4-(4-乙氧基 - 苯基)-2-(芴-9-亚基 - 亚氨基) - 丁-3-烯酸甲酯(3F-19)。