JP2013502441A - 新規コルヒチン誘導体、方法、およびその使用 - Google Patents

新規コルヒチン誘導体、方法、およびその使用 Download PDF

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Publication number
JP2013502441A
JP2013502441A JP2012525826A JP2012525826A JP2013502441A JP 2013502441 A JP2013502441 A JP 2013502441A JP 2012525826 A JP2012525826 A JP 2012525826A JP 2012525826 A JP2012525826 A JP 2012525826A JP 2013502441 A JP2013502441 A JP 2013502441A
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substituted
unsubstituted
cancer
compound
carcinoma
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JP2013502441A5 (enExample
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トゥスジンスキー，ジャック
マネ，ジョナサン・ワイ
ハズィル，ジョン・トリン
トマネック，ボーガスロー
バルチュシーク，ドロタ
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Alberta Health Services
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Alberta Health Services
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/40—Y being a hydrogen or a carbon atom
    • C07C323/41—Y being a hydrogen or an acyclic carbon atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/30—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
    • C07C233/32—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/61—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/5005—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells
    • G01N33/5008—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics
    • G01N33/5082—Supracellular entities, e.g. tissue, organisms
    • G01N33/5088—Supracellular entities, e.g. tissue, organisms of vertebrates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/30—Ortho- or ortho- and peri-condensed systems containing three rings containing seven-membered rings
    • C07C2603/34—Benzoheptalenes; Hydrogenated benzoheptalenes
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N2500/00—Screening for compounds of potential therapeutic value
    • G01N2500/10—Screening for compounds of potential therapeutic value involving cells

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Immunology (AREA)
  • Hematology (AREA)
  • Urology & Nephrology (AREA)
  • Cell Biology (AREA)
  • Molecular Biology (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Biochemistry (AREA)
  • Pathology (AREA)
  • General Physics & Mathematics (AREA)
  • Analytical Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Toxicology (AREA)
  • Food Science & Technology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Pyridine Compounds (AREA)
JP2012525826A 2009-08-26 2010-07-30 新規コルヒチン誘導体、方法、およびその使用 Pending JP2013502441A (ja)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US23714209P 2009-08-26 2009-08-26
US61/237,142 2009-08-26
US24013209P 2009-09-04 2009-09-04
US61/240,132 2009-09-04
PCT/CA2010/001199 WO2011022805A1 (en) 2009-08-26 2010-07-30 Novel colchicine derivatives, methods and uses thereof

Publications (2)

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JP2013502441A true JP2013502441A (ja) 2013-01-24
JP2013502441A5 JP2013502441A5 (enExample) 2013-09-19

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US (1) US9458101B2 (enExample)
EP (1) EP2470499B1 (enExample)
JP (1) JP2013502441A (enExample)
CA (1) CA2808277C (enExample)
DK (1) DK2470499T3 (enExample)
ES (1) ES2745255T3 (enExample)
PL (1) PL2470499T3 (enExample)
WO (1) WO2011022805A1 (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2022511214A (ja) * 2018-06-29 2022-01-31 アルバータ ヘルス サービシズ コルヒチン誘導体の方法と使用

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2500670C1 (ru) * 2012-08-07 2013-12-10 Федеральное Государственное Бюджетное Образовательное Учреждение Высшего Профессионального Образования "Нижегородский Государственный Университет Им. Н.И. Лобачевского" ПРОИЗВОДНОЕ 1',2',3'-ТРИМЕТОКСИБЕНЗО[4',5':4,5]-6,7-ДИГИДРОЦИКЛОГЕПТА-[2,3-e]-1H-1-МЕТИЛИНДОЛА И ЕГО ПРИМЕНЕНИЕ
RU2500671C1 (ru) * 2012-08-07 2013-12-10 Федеральное Государственное Бюджетное Образовательное Учреждение Высшего Профессионального Образования "Нижегородский Государственный Университет Им. Н.И. Лобачевского" ПРОИЗВОДНОЕ 1',2',3'-ТРИМЕТОКСИБЕНЗО[4',5':4,5]-6,7-ДИГИДРОЦИКЛОГЕПТА-[3,2-f]-1H-1-МЕТИЛИНДОЛА И ЕГО ПРИМЕНЕНИЕ
SG11201503440UA (en) 2012-11-02 2015-06-29 Heart Care Western Australia Pty Ltd Treatment or prevention of cardiovascular events via the administration of a colchicine derivative
RU2538982C1 (ru) * 2013-11-19 2015-01-10 Федеральное Государственное Бюджетное Образовательное Учреждение Высшего Профессионального Образования "Нижегородский Государственный Университет Им. Н.И. Лобачевского" Производное n-(1s)-1',2',3'-триметокси-6,7-дигидро-1н-бензо[5',6':5,4]циклогепта-[3,2-f]бензофуран-1-ил)ацетамида и его применение
US9868695B2 (en) 2014-10-14 2018-01-16 Council Of Scientific & Industrial Research 10-substituted colchicinoids as potent anticancer agents
RU2593998C1 (ru) * 2015-06-23 2016-08-10 федеральное государственное автономное образовательное учреждение высшего образования "Нижегородский государственный университет им. Н.И. Лобачевского" ПРОИЗВОДНОЕ 1', 2', 3'-ТРИМЕТОКСИБЕНЗО[5', 6:5, 4]-1H-6, 7-ДИГИДРОЦИКЛОГЕПТА[3, 2-f]БЕНЗОФУРАНА И ЕГО ПРИМЕНЕНИЕ
RU2630303C1 (ru) * 2016-11-30 2017-09-08 Федеральное государственное автономное образовательное учреждение высшего образования "Национальный исследовательский Нижегородский государственный университет им. Н.И. Лобачевского" Производное 1'-бромо-2',3',4'-триметоксибензо[5',6':4,5]-(aR, 1S)-1-ацетамидо-6,7-дигидроциклогепта-[3,4-f]-1Н-индола и его применение
WO2018236879A1 (en) 2017-06-19 2018-12-27 University Of Maryland, Baltimore INHIBITORS OF MICROTUBULAR POLYMERIZATION PRODRUGS AND METHODS OF USE
RU2678440C1 (ru) * 2018-07-23 2019-01-29 Федеральное государственное автономное образовательное учреждение высшего образования "Национальный исследовательский Нижегородский государственный университет им. Н.И. Лобачевского" ПРОИЗВОДНОЕ 1",2",3"-ТРИМЕТОКСИБЕНЗО[5",6":5',4']1H-(aR,1S)-1-АЦЕТАМИДО-6',7'-ДИГИДРОЦИКЛОГЕПТА[2',3'-f]-2,3-ДИГИДРОФУРАНА И ЕГО ПРИМЕНЕНИЕ
WO2021089715A1 (en) * 2019-11-06 2021-05-14 Murray And Poole Enterprises, Ltd. Use of colchicine in the treatment and prevention of lung cancer
CN116082182A (zh) * 2021-11-08 2023-05-09 天津市昕晨投资发展有限公司 秋水仙碱衍生物的制备方法及其用途

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB763217A (en) * 1954-02-10 1956-12-12 Roussel Uclaf Colchiceine derivatives
JPH0967326A (ja) * 1995-03-03 1997-03-11 Roussel Uclaf 新規な三環式誘導体、それらの製造法、光学活性又はラセミ形のコルヒチン及びチオコルヒチン並びにそれらの類似体又は誘導体の製造への使用並びに中間体
JPH10507169A (ja) * 1994-10-05 1998-07-14 インデナ・ソチエタ・ペル・アチオニ コルヒチン誘導体及びその治療的利用
JP2012531407A (ja) * 2009-07-08 2012-12-10 ジェ イル ファーマシューティカル カンパニー リミテッド トリサイクリック誘導体の製造方法

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FR1344474A (fr) 1962-10-18 1963-11-29 Roussel Uclaf Dérivés de la colchicine et de la thiocolchicine et procédé de préparation
US4533675A (en) * 1984-04-17 1985-08-06 The United States Of America As Represented By The Department Of Health And Human Services Carbamates of colchicine for treatment of gout
US5175342A (en) 1988-08-24 1992-12-29 The United States Of America As Represented By The Department Of Health And Human Services Esters of 3-demethylthiocolchicine and n-acyl analogs
US5747469A (en) 1991-03-06 1998-05-05 Board Of Regents, The University Of Texas System Methods and compositions comprising DNA damaging agents and p53
IT1276996B1 (it) 1995-06-27 1997-11-04 Indena Spa Derivati della colchicina, loro uso e formulazioni che li contengono
GB9904387D0 (en) 1999-02-25 1999-04-21 Pharmacia & Upjohn Spa Antitumour synergistic composition
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US6825236B2 (en) * 2003-04-14 2004-11-30 California Pacific Medical Center Colchicine derivatives
ES2358801T3 (es) 2003-06-25 2011-05-13 Je Il Pharmaceutical Co., Ltd. Derivados tricíclicos o sales farmacéuticamente aceptables de los mismos, sus preparaciones y composiciones farmacéuticas que los contienen.
JP5829520B2 (ja) 2009-08-20 2015-12-09 国立大学法人 千葉大学 コルヒチン誘導体

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB763217A (en) * 1954-02-10 1956-12-12 Roussel Uclaf Colchiceine derivatives
JPH10507169A (ja) * 1994-10-05 1998-07-14 インデナ・ソチエタ・ペル・アチオニ コルヒチン誘導体及びその治療的利用
JPH0967326A (ja) * 1995-03-03 1997-03-11 Roussel Uclaf 新規な三環式誘導体、それらの製造法、光学活性又はラセミ形のコルヒチン及びチオコルヒチン並びにそれらの類似体又は誘導体の製造への使用並びに中間体
JP2012531407A (ja) * 2009-07-08 2012-12-10 ジェ イル ファーマシューティカル カンパニー リミテッド トリサイクリック誘導体の製造方法

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JPN6014035447; ＭＵＺＡＦＦＡＲ，Ａ．　ｅｔ　ａｌ．: 'Ａｎｔｉｔｕｂｕｌｉｎ　ｅｆｆｅｃｔｓ　ｏｆ　ｄｅｒｉｖａｔｉｖｅｓ　ｏｆ　３-ｄｅｍｅｔｈｙｌｔｈｉｏｃｏｌｃｈｉｃｉｎｅ，　ｍｅｔｈｙｌｔｈｉｏ　ｅｔｈｅｒｓ　ｏｆ　ｎａｔｕｒａｌ　ｃｏｌｃｈｉｃ' Ｊｏｕｒｎａｌ　ｏｆ　Ｍｅｄｉｃｉｎａｌ　Ｃｈｅｍｉｓｔｒｙ Ｖｏｌ．３３, 1990, ｐ．５６７-５７１ *
JPN6014035448; ＫＥＲＫＥＳ，Ｐ．　ｅｔ　ａｌ．: 'Ｓｙｎｔｈｅｓｉｓ　ａｎｄ　ｂｉｏｌｏｇｉｃａｌ　ｅｆｆｅｃｔｓ　ｏｆ　ｎｏｖｅｌ　ｔｈｉｏｃｏｌｃｈｉｃｉｎｅｓ．　３．　ｅｖａｌｕａｔｉｏｎ　ｏｆ　Ｎ-ａｃｙｌｄｅａｃｅｔｙｌｔｈｉｏｃｏｌｃｈｉ' Ｊｏｕｒｎａｌ　ｏｆ　Ｍｅｄｉｃｉｎａｌ　Ｃｈｅｍｉｓｔｒｙ Ｖｏｌ．２８, 1985, ｐ．１２０４-１２０８ *
JPN6014035449; ＷＡＬＴＥＲＯＶＡ，Ｄ．　ｅｔ　ａｌ．: 'Ｃｉｒｃｕｌａｒ　ｄｉｃｈｒｏｉｃ　ｓｐｅｃｔｒａ　ａｎｄ　ｉｏｎｉｚａｔｉｏｎ　ｐｒｏｃｅｓｓｅｓ　ｏｆ　ｓｏｍｅ　ｔｒｏｐｏｌｏｎｉｃ　ａｌｋａｌｏｉｄｓ' Ｈｅｔｅｒｏｃｙｃｌｅｓ Ｖｏｌ．２５, 1987, ｐ．８９-９６ *
JPN6014035450; ＣＡＮＯＮＩＣＡ，Ｌ．　ｅｔ　ａｌ．: 'Ｎｅｗ　ａｌｋａｌｏｉｄｓ　ｆｒｏｍ　ｇｌｏｒｉｏｓａ　ｓｕｐｅｒｂａ' Ｃｈｉｍｉｃａ　ｅ　ｌ'Ｉｎｄｕｓｔｒｉａ Ｖｏｌ．４９，　Ｎｏ．１２, 1967, ｐ．１３０４-１３１２ *
JPN6014035451; ＶＩＬＡＲ，Ｓ．　ｅｔ　ａｌ．: 'Ｐｒｏｂａｂｉｌｉｓｔｉｃ　Ｎｅｕｒａｌ　Ｎｅｔｗｏｒｋ　Ｍｏｄｅｌ　ｆｏｒ　ｔｈｅ　Ｉｎ　Ｓｉｌｉｃｏ　Ｅｖａｌｕａｔｉｏｎ　ｏｆ　Ａｎｔｉ-ＨＩＶ　Ａｃｔｉｖｉｔｙ　ａｎｄ　Ｍｅｃｈａｎｉｓｍ　ｏ' Ｊｏｕｒｎａｌ　ｏｆ　Ｍｅｄｉｃｉｎａｌ　Ｃｈｅｍｉｓｔｒｙ Ｖｏｌ．４９, 2006, ｐ．１１１８-２４，　Ｓｕｐｐｏｒｔｉｎｇ　Ｉｎｆｏｒｍａｔｉｏｎ　Ｓ１-１０１ *
JPN6014035452; ＤＡＮＩＥＬＩ，Ｂ．　ｅｔ　ａｌ．: 'Ａｔｔｅｍｐｔｅｄ　Ｏｘｉｄａｔｉｖｅ　Ｄｅａｍｉｎａｔｉｏｎ　ｏｆ　Ｎ-Ｄｅａｃｅｔｙｌｃｏｌｃｈｉｃｉｎｏｉｄｓ　ｗｉｔｈ　３，５-Ｄｉ（ｔｅｒｔ-ｂｕｔｙｌ）-１，２-ｂｅｎｚｏｑｕｉｎｏｎｅ：' Ｈｅｌｖｅｔｉｃａ　Ｃｈｉｍｉｃａ　Ａｃｔａ Ｖｏｌ．８２, 1999, ｐ．１５０２-１５０８ *
JPN7014002511; ＳＡＤＹＫＯＶ，Ａ．　ａｎｄ　ＹＵＳＵＰＯＶ，Ｍ．Ｋ．: 'Ｔｈｅ　ａｌｋａｌｏｉｄｓ　ｏｆ　ｃｏｌｃｈｉｃｕｍ　ｋｅｓｓｅｌｒｉｎｇｉｉ' Ｕｚｂｅｋｓｋｉｉ　Ｋｈｉｍｉｃｈｅｓｋｉｉ　Ｚｈｕｒｎａｌ Ｎｏ．２, 1960, ｐ．３８-４４ *
JPN7014002512; ＢＡＲＴＵＳＩＫ，Ｄ．　ｅｔ　ａｌ．: 'Ｔｈｅ　ｅｆｆｉｃａｃｙ　ｏｆ　ｎｅｗ　ｃｏｌｃｈｉｃｉｎｅ　ｄｅｒｉｖａｔｉｖｅｓ　ａｎｄ　ｖｉａｂｉｌｉｔｙ　ｏｆ　ｔｈｅ　Ｔ-Ｌｙｍｐｈｏｂｌａｓｔｏｉｄ　ｃｅｌｌｓ　ｉｎ　ｔｈｒｅｅ-ｄｉｍｅ' Ｂｉｏｏｒｇａｎｉｃ　Ｃｈｅｍｉｓｔｒｙ Ｖｏｌ．３７, 2009, ｐ．１９３-２０１ *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2022511214A (ja) * 2018-06-29 2022-01-31 アルバータ ヘルス サービシズ コルヒチン誘導体の方法と使用
US12324799B2 (en) 2018-06-29 2025-06-10 Alberta Health Services Methods and uses of colchicine derivatives

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CA2808277A1 (en) 2011-03-03
EP2470499A4 (en) 2013-03-27
US20120225912A1 (en) 2012-09-06
EP2470499A1 (en) 2012-07-04
US9458101B2 (en) 2016-10-04
CA2808277C (en) 2018-01-16
WO2011022805A1 (en) 2011-03-03

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