RU2000129508A - SULPHONAMIDE-CONTAINING INDOL COMPOUNDS - Google Patents
SULPHONAMIDE-CONTAINING INDOL COMPOUNDSInfo
- Publication number
- RU2000129508A RU2000129508A RU2000129508/04A RU2000129508A RU2000129508A RU 2000129508 A RU2000129508 A RU 2000129508A RU 2000129508/04 A RU2000129508/04 A RU 2000129508/04A RU 2000129508 A RU2000129508 A RU 2000129508A RU 2000129508 A RU2000129508 A RU 2000129508A
- Authority
- RU
- Russia
- Prior art keywords
- indole
- hydrates
- acceptable salt
- pharmacologically acceptable
- group
- Prior art date
Links
- SIKJAQJRHWYJAI-UHFFFAOYSA-N indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title claims 37
- 201000011510 cancer Diseases 0.000 claims 28
- 150000004677 hydrates Chemical class 0.000 claims 26
- 150000003839 salts Chemical class 0.000 claims 26
- 239000011780 sodium chloride Substances 0.000 claims 26
- -1 indole compound Chemical class 0.000 claims 25
- 239000003814 drug Substances 0.000 claims 20
- 229940079593 drugs Drugs 0.000 claims 20
- 239000004615 ingredient Substances 0.000 claims 13
- 206010039073 Rheumatoid arthritis Diseases 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 11
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 9
- 206010027476 Metastasis Diseases 0.000 claims 8
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 7
- 125000004802 cyanophenyl group Chemical group 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 210000001072 Colon Anatomy 0.000 claims 3
- 210000004072 Lung Anatomy 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- DLVDWXFCCXIVPA-UHFFFAOYSA-N 2-amino-N-(4-bromo-3-chloro-1H-indol-7-yl)pyrimidine-5-sulfonamide Chemical compound C1=NC(N)=NC=C1S(=O)(=O)NC1=CC=C(Br)C2=C1NC=C2Cl DLVDWXFCCXIVPA-UHFFFAOYSA-N 0.000 claims 2
- KYLVSIKHMMRCSQ-UHFFFAOYSA-N 4-N-(3-bromo-5-methyl-1H-indol-7-yl)benzene-1,4-disulfonamide Chemical compound C=12NC=C(Br)C2=CC(C)=CC=1NS(=O)(=O)C1=CC=C(S(N)(=O)=O)C=C1 KYLVSIKHMMRCSQ-UHFFFAOYSA-N 0.000 claims 2
- ITCMHMKNTZGBIG-UHFFFAOYSA-N 6-amino-N-(3-bromo-4-chloro-1H-indol-7-yl)pyridine-3-sulfonamide Chemical compound C1=NC(N)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C2=C1NC=C2Br ITCMHMKNTZGBIG-UHFFFAOYSA-N 0.000 claims 2
- HAVIQLLUANGVOL-UHFFFAOYSA-N 6-amino-N-(5-bromo-3-chloro-1H-indol-7-yl)pyridine-3-sulfonamide Chemical compound C1=NC(N)=CC=C1S(=O)(=O)NC1=CC(Br)=CC2=C1NC=C2Cl HAVIQLLUANGVOL-UHFFFAOYSA-N 0.000 claims 2
- YPSROFYZMXLNMS-UHFFFAOYSA-N 6-chloro-N-(3-cyano-4-methyl-1H-indol-7-yl)pyridine-3-sulfonamide Chemical compound C1=2NC=C(C#N)C=2C(C)=CC=C1NS(=O)(=O)C1=CC=C(Cl)N=C1 YPSROFYZMXLNMS-UHFFFAOYSA-N 0.000 claims 2
- RDEPSYHIJAQFIZ-UHFFFAOYSA-N N-(3-bromo-5-methyl-1H-indol-7-yl)-3-cyanobenzenesulfonamide Chemical compound C=12NC=C(Br)C2=CC(C)=CC=1NS(=O)(=O)C1=CC=CC(C#N)=C1 RDEPSYHIJAQFIZ-UHFFFAOYSA-N 0.000 claims 2
- BRBOULQMFKYIEZ-UHFFFAOYSA-N N-(3-bromo-5-methyl-1H-indol-7-yl)-5-cyanothiophene-2-sulfonamide Chemical compound C=12NC=C(Br)C2=CC(C)=CC=1NS(=O)(=O)C1=CC=C(C#N)S1 BRBOULQMFKYIEZ-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 210000001672 Ovary Anatomy 0.000 claims 2
- 210000002307 Prostate Anatomy 0.000 claims 2
- 210000002784 Stomach Anatomy 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 239000004037 angiogenesis inhibitor Substances 0.000 claims 2
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- SCPZNFHIYLYDTJ-UHFFFAOYSA-N 6-amino-N-(4-chloro-1H-indol-7-yl)pyridine-3-sulfonamide Chemical compound C1=NC(N)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C2=C1NC=C2 SCPZNFHIYLYDTJ-UHFFFAOYSA-N 0.000 claims 1
- 206010003246 Arthritis Diseases 0.000 claims 1
- 210000000481 Breast Anatomy 0.000 claims 1
- 206010018852 Haematoma Diseases 0.000 claims 1
- 210000002264 Mammary Glands, Animal Anatomy 0.000 claims 1
- 210000004293 Mammary Glands, Human Anatomy 0.000 claims 1
- DADBBXMQNCKWAA-UHFFFAOYSA-N N-(4-bromo-1H-indol-7-yl)-4-cyanobenzenesulfonamide Chemical compound C1=2NC=CC=2C(Br)=CC=C1NS(=O)(=O)C1=CC=C(C#N)C=C1 DADBBXMQNCKWAA-UHFFFAOYSA-N 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 210000000496 Pancreas Anatomy 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 206010038932 Retinopathy Diseases 0.000 claims 1
- 206010038923 Retinopathy Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 230000003178 anti-diabetic Effects 0.000 claims 1
- 230000003356 anti-rheumatic Effects 0.000 claims 1
- 239000003472 antidiabetic agent Substances 0.000 claims 1
- 239000003560 cancer drug Substances 0.000 claims 1
- 230000002496 gastric Effects 0.000 claims 1
- 125000006377 halopyridyl group Chemical group 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 230000002611 ovarian Effects 0.000 claims 1
- 230000001629 suppression Effects 0.000 claims 1
Claims (27)
где R1 представляет собой атом водорода, атом галогена или цианогруппу; R2 и R3 являются одинаковыми или отличными, и каждый представляет собой атом водорода, C1-C4 низшую алкильную группу или атом галогена; R4 представляет собой атом водорода или C1-C4 низшую алкильную группу; и кольцо А представляет собой цианофенильную группу, аминосульфонилфенильную группу, аминопиридильную группу, аминопиримидильную группу, галогенпиридильную группу или цианотиофенильную группу, при условии, что случаи, когда и R1, и R2, и R3 представляют собой атомы водорода, когда оба R2 и R3 представляют собой атомы водорода, или когда кольцо А представляет собой аминосульфонильную группу, и оба R1 и R2 представляют собой атомы галогена, исключены; и кроме того, когда кольцо А представляет собой цианофенильную группу, 2-амино-5-пиридильную группу или 2-галоген-5-пиридильную группу, и R1 представляет собой цианогруппу или галогеновую группу, и, по крайней мере, один из R2 и R3 не должен быть атомом водорода.1. The indole compound represented by the following formula I, its pharmacologically acceptable salt or its hydrates
where R 1 represents a hydrogen atom, a halogen atom or a cyano group; R 2 and R 3 are the same or different, and each represents a hydrogen atom, a C 1 -C 4 lower alkyl group or a halogen atom; R 4 represents a hydrogen atom or a C 1 -C 4 lower alkyl group; and ring A is a cyanophenyl group, an aminosulfonylphenyl group, an aminopyridyl group, an aminopyrimidyl group, a halopyridyl group or a cyanothiophenyl group, provided that the cases when both R 1 and R 2 and R 3 are hydrogen atoms when both R 2 and R 3 are hydrogen atoms, or when ring A is an aminosulfonyl group, and both R 1 and R 2 are halogen atoms are excluded; and furthermore, when ring A is a cyanophenyl group, a 2-amino-5-pyridyl group or a 2-halogen-5-pyridyl group, and R 1 is a cyano group or halogen group, and at least one of R 2 and R 3 must not be a hydrogen atom.
3-циано-N-(3-циано-4-метил-1Н-индол-7-ил)бензолсульфонамид,
6-хлор-N-(3-циано-4-метил-1Н-индол-7-ил)-3-пиридин-сульфонамид,
N-(3-бром-5-метил-1Н-индол-7-ил)-4-сульфамоилбензолсульфонамид,
6-амино-N-(5-бром-3-хлор-1Н-индол-7-ил)-3-пиридинсульфонамид,
N-(3-бром-5-метил-1Н-индол-7-ил)-3-цианобензолсульфонамид,
N-(4-бром-1Н-индол-7-ил)-4-цианобензолсульфонамид,
6-амино-N-(4-хлор-1Н-индол-7-ил)-3-пиридинсульфонамид,
6-амино-N-(3-бром-4-хлор-1Н-индол-7-ил)-3-пиридинсульфонамид,
N-(3-бром-5-метил-1Н-индол-7-ил)-5-циано-2-тиофенсульфонамид и
2-амино-N-(4-бром-3-хлор-1Н-индол-7-ил)-5-пиримидинсульфонамид.9. The indole compound according to claim 1, selected from the following compounds, its pharmacologically acceptable salt or its hydrates:
3-cyano-N- (3-cyano-4-methyl-1H-indole-7-yl) benzenesulfonamide,
6-chloro-N- (3-cyano-4-methyl-1H-indole-7-yl) -3-pyridine sulfonamide,
N- (3-bromo-5-methyl-1H-indol-7-yl) -4-sulfamoylbenzene sulfonamide,
6-amino-N- (5-bromo-3-chloro-1H-indole-7-yl) -3-pyridinesulfonamide,
N- (3-bromo-5-methyl-1H-indol-7-yl) -3-cyanobenzenesulfonamide,
N- (4-bromo-1H-indole-7-yl) -4-cyanobenzenesulfonamide,
6-amino-N- (4-chloro-1H-indol-7-yl) -3-pyridinesulfonamide,
6-amino-N- (3-bromo-4-chloro-1H-indole-7-yl) -3-pyridinesulfonamide,
N- (3-bromo-5-methyl-1H-indol-7-yl) -5-cyano-2-thiophenesulfonamide and
2-amino-N- (4-bromo-3-chloro-1H-indole-7-yl) -5-pyrimidine sulfonamide.
3-циано-N-(3-циано-4-метил-1Н-индол-7-ил)бензолсульфонамид,
6-хлор-N-(3-циано-4-метил-1Н-индол-7-ил)-3-пиридинсульфонамид,
N-(3-бром-5-метил-1Н-индол-7-ил)-4-сульфамоилбензолсульфонамид,
6-амино-N-(5-бром-3-хлор-1Н-индол-7-ил)-3-пиридинсульфонамид,
N-(3-бром-5-метил-1Н-индол-7-ил)-3-цианобензолсульфонамид,
6-амино-N-(3-бром-4-хлор-1Н-индол-7-ил)-3-пиридинсульфонамид,
N-(3-бром-5-метил-1Н-индол-7-ил)-5-циано-2-тиофенсульфонамид и
2-амино-N-(4-бром-3-хлор-1Н-индол-7-ил)-5-пиримидинсульфонамид.10. The indole compound according to claim 1, selected from the following compounds, its pharmacologically acceptable salt or its hydrates:
3-cyano-N- (3-cyano-4-methyl-1H-indole-7-yl) benzenesulfonamide,
6-chloro-N- (3-cyano-4-methyl-1H-indole-7-yl) -3-pyridinesulfonamide,
N- (3-bromo-5-methyl-1H-indol-7-yl) -4-sulfamoylbenzene sulfonamide,
6-amino-N- (5-bromo-3-chloro-1H-indole-7-yl) -3-pyridinesulfonamide,
N- (3-bromo-5-methyl-1H-indol-7-yl) -3-cyanobenzenesulfonamide,
6-amino-N- (3-bromo-4-chloro-1H-indole-7-yl) -3-pyridinesulfonamide,
N- (3-bromo-5-methyl-1H-indol-7-yl) -5-cyano-2-thiophenesulfonamide and
2-amino-N- (4-bromo-3-chloro-1H-indole-7-yl) -5-pyrimidine sulfonamide.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11049870A JP2000247949A (en) | 1999-02-26 | 1999-02-26 | Indole compound containing sulfonamide |
JP11/49870 | 1999-02-26 |
Publications (2)
Publication Number | Publication Date |
---|---|
RU2000129508A true RU2000129508A (en) | 2002-10-27 |
RU2208607C2 RU2208607C2 (en) | 2003-07-20 |
Family
ID=12843091
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU2000129508/04A RU2208607C2 (en) | 1999-02-26 | 2000-02-24 | Sulfonamide-containing indole compounds |
Country Status (17)
Country | Link |
---|---|
US (3) | US6469043B1 (en) |
EP (1) | EP1074542B1 (en) |
JP (3) | JP2000247949A (en) |
KR (1) | KR100627611B1 (en) |
CN (1) | CN1132814C (en) |
AT (1) | ATE325094T1 (en) |
AU (1) | AU766936B2 (en) |
CA (1) | CA2327253C (en) |
DE (1) | DE60027648T2 (en) |
DK (1) | DK1074542T3 (en) |
ES (1) | ES2259997T3 (en) |
HU (1) | HU228787B1 (en) |
NO (1) | NO317299B1 (en) |
NZ (1) | NZ507464A (en) |
PT (1) | PT1074542E (en) |
RU (1) | RU2208607C2 (en) |
WO (1) | WO2000050395A1 (en) |
Families Citing this family (34)
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DE60141889D1 (en) * | 2000-02-03 | 2010-06-02 | Eisai R&D Man Co Ltd | INHIBITORS OF INTEGRINEXPRESSION |
AU2001288518A1 (en) * | 2000-08-30 | 2002-03-13 | Primecyte, Inc. | Methods for treating tumors using sulfonyl compounds |
TWI283575B (en) * | 2000-10-31 | 2007-07-11 | Eisai Co Ltd | Medicinal compositions for concomitant use as anticancer agent |
DE60217300T2 (en) * | 2001-02-21 | 2007-10-04 | Eisai Co., Ltd. | METHOD OF INVESTIGATING THE EFFECT OF AN ANGIONEGESIS HEMMER THROUGH INHIBITION BY INFRINGEMENT OF INTEGRIN EXPRESSION |
ATE380028T1 (en) * | 2001-09-05 | 2007-12-15 | Eisai R&D Man Co Ltd | AGENTS FOR STIMULATING APPETITE AND AGENTS FOR TREATING ANOREXIA |
JPWO2003022271A1 (en) * | 2001-09-05 | 2004-12-24 | エーザイ株式会社 | Lymphocyte activation inhibitor and therapeutic agent for autoimmune diseases |
EP1481678A4 (en) * | 2002-03-05 | 2009-12-30 | Eisai R&D Man Co Ltd | Antitumor agent comprising combination of sulfonamide-containing heterocyclic compound with angiogenesis inhibitor |
CA2520732C (en) | 2003-03-28 | 2012-12-04 | Sloan-Kettering Institute For Cancer Research | Migrastatin analogs and uses thereof |
WO2004091664A1 (en) * | 2003-04-18 | 2004-10-28 | Eisai Co., Ltd. | Cytoplasmic malate dehydrogenase inhibitor |
EP1666463B1 (en) | 2003-09-10 | 2010-11-03 | Eisai R&D Management Co., Ltd. | Crystal of sulfonamide-containing indole compound and process for producing the same |
JP4418430B2 (en) * | 2003-09-10 | 2010-02-17 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | Method for producing sulfonamide-containing indole compound |
WO2005048938A2 (en) * | 2003-11-13 | 2005-06-02 | California Pacific Medical Center | Anti-pecam therapy for metastasis suppression |
JP5149001B2 (en) * | 2004-05-25 | 2013-02-20 | スローン−ケッタリング・インスティテュート・フォー・キャンサー・リサーチ | Migrastatin analogues in the treatment of cancer |
US8772269B2 (en) | 2004-09-13 | 2014-07-08 | Eisai R&D Management Co., Ltd. | Use of sulfonamide-including compounds in combination with angiogenesis inhibitors |
WO2006030947A1 (en) | 2004-09-13 | 2006-03-23 | Eisai R & D Management Co., Ltd. | Joint use of sulfonamide based compound with angiogenesis inhibitor |
CA2582766C (en) * | 2004-09-23 | 2014-07-22 | Sloan-Kettering Institute For Cancer Research | Isomigrastatin analogs in the treatment of cancer |
AU2006217692A1 (en) | 2005-02-28 | 2006-08-31 | Eisai R & D Management Co., Ltd. | Novel combinational use of sulfonamide compound |
US8957070B2 (en) | 2005-04-20 | 2015-02-17 | Takeda Pharmaceutical Company Limited | Glucokinase activator compounds, methods of activating glucokinase and methods of treating diabetes and obesity |
CN101360422B (en) * | 2005-11-23 | 2013-10-23 | 得克萨斯大学体系董事会 | Oncogenic Ras-specific cytotoxic compound and methods of usethereof |
US7625896B2 (en) * | 2005-11-25 | 2009-12-01 | Hoffman-La Roche Inc. | Pyridylsulfonamide derivatives |
WO2007086605A1 (en) * | 2006-01-27 | 2007-08-02 | Eisai R & D Management Co., Ltd. | Method for prediction of the effect of sulfonamide compound |
EP2015070A4 (en) | 2006-04-20 | 2010-04-21 | Eisai R&D Man Co Ltd | Novel marker for sensitivity against sulfonamide compound |
DE102007012284A1 (en) * | 2007-03-16 | 2008-09-18 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Novel substituted arylsulfonylglycines, their preparation and their use as pharmaceuticals |
DE102007035333A1 (en) | 2007-07-27 | 2009-01-29 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Novel substituted arylsulfonylglycines, their preparation and their use as pharmaceuticals |
DE102007035334A1 (en) | 2007-07-27 | 2009-01-29 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Novel substituted arylsulfonylglycines, their preparation and their use as pharmaceuticals |
DE102007042154A1 (en) | 2007-09-05 | 2009-03-12 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Arylsulfonylaminomethyphosphonsäure derivatives, their preparation and their use as medicaments |
US20090142832A1 (en) * | 2007-11-29 | 2009-06-04 | James Dalton | Indoles, Derivatives, and Analogs Thereof and Uses Therefor |
JP2012136435A (en) * | 2009-03-30 | 2012-07-19 | Eisai R & D Management Co Ltd | Method for examining sensitivity of tumor tissue |
BR112014020773A2 (en) | 2012-02-22 | 2020-10-27 | Sanford-Burnham Medical Research Institute | sulfonamide compounds and their uses as tnap inhibitors |
CN104098498A (en) * | 2014-07-30 | 2014-10-15 | 天津市斯芬克司药物研发有限公司 | Indazole-type compound and preparation method thereof |
US11072583B2 (en) | 2017-11-27 | 2021-07-27 | Council Of Scientific & Industrial Research | Indole (sulfomyl) n-hydroxy benzamide derivatives as selective HDAC inhibitors |
WO2019147783A1 (en) * | 2018-01-25 | 2019-08-01 | Dana-Farber Cancer Institute, Inc. | Sulfonamide derivatives for protein degradation |
US20220162193A1 (en) * | 2019-04-10 | 2022-05-26 | Peloton Therapeutics, Inc. | Pyrazolesulfonamides as antitumor agents |
WO2024039689A1 (en) * | 2022-08-15 | 2024-02-22 | Recursion Pharmaceuticals, Inc. | Heterocycle rbm39 modulators |
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GB9115160D0 (en) * | 1991-07-12 | 1991-08-28 | Erba Carlo Spa | Methylen-oxindole derivatives and process for their preparation |
CN1221533C (en) * | 1993-09-10 | 2005-10-05 | 卫材株式会社 | Heterobicyclic sulfonamide derivative and sulfonic ester derivative |
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JP3690831B2 (en) * | 1995-02-27 | 2005-08-31 | エーザイ株式会社 | Indole-containing sulfonamide derivatives |
US6060498A (en) * | 1996-02-26 | 2000-05-09 | Eisai Co., Ltd. | Composition containing antitumor agent |
JP3868534B2 (en) * | 1996-05-24 | 2007-01-17 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | Process for producing sulfonamide derivatives and intermediates |
DE60141889D1 (en) | 2000-02-03 | 2010-06-02 | Eisai R&D Man Co Ltd | INHIBITORS OF INTEGRINEXPRESSION |
-
1999
- 1999-02-26 JP JP11049870A patent/JP2000247949A/en active Pending
-
2000
- 2000-02-24 DE DE60027648T patent/DE60027648T2/en not_active Expired - Lifetime
- 2000-02-24 CN CN008002290A patent/CN1132814C/en not_active Expired - Fee Related
- 2000-02-24 CA CA002327253A patent/CA2327253C/en not_active Expired - Fee Related
- 2000-02-24 ES ES00905321T patent/ES2259997T3/en not_active Expired - Lifetime
- 2000-02-24 KR KR1020007011026A patent/KR100627611B1/en not_active IP Right Cessation
- 2000-02-24 RU RU2000129508/04A patent/RU2208607C2/en not_active IP Right Cessation
- 2000-02-24 HU HU0101434A patent/HU228787B1/en not_active IP Right Cessation
- 2000-02-24 DK DK00905321T patent/DK1074542T3/en active
- 2000-02-24 NZ NZ507464A patent/NZ507464A/en not_active IP Right Cessation
- 2000-02-24 WO PCT/JP2000/001071 patent/WO2000050395A1/en active IP Right Grant
- 2000-02-24 JP JP2000600978A patent/JP3866041B2/en not_active Expired - Fee Related
- 2000-02-24 AT AT00905321T patent/ATE325094T1/en active
- 2000-02-24 EP EP00905321A patent/EP1074542B1/en not_active Expired - Lifetime
- 2000-02-24 AU AU26916/00A patent/AU766936B2/en not_active Ceased
- 2000-02-24 US US09/647,215 patent/US6469043B1/en not_active Expired - Lifetime
- 2000-02-24 PT PT00905321T patent/PT1074542E/en unknown
- 2000-10-24 NO NO20005357A patent/NO317299B1/en not_active IP Right Cessation
-
2002
- 2002-03-18 US US10/098,420 patent/US6673787B2/en not_active Expired - Lifetime
- 2002-03-18 US US10/098,421 patent/US6638964B2/en not_active Expired - Lifetime
-
2010
- 2010-04-02 JP JP2010085696A patent/JP2010180229A/en active Pending
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