RU2011152113A - DERIVATIVES OF NAPHTHALINE CARBOXAMIDE AS PROTEINKINASE AND HISTONDEACETHYLASE INHIBITORS, METHODS FOR THEIR PRODUCTION AND APPLICATION - Google Patents

DERIVATIVES OF NAPHTHALINE CARBOXAMIDE AS PROTEINKINASE AND HISTONDEACETHYLASE INHIBITORS, METHODS FOR THEIR PRODUCTION AND APPLICATION Download PDF

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RU2011152113A
RU2011152113A RU2011152113/04A RU2011152113A RU2011152113A RU 2011152113 A RU2011152113 A RU 2011152113A RU 2011152113/04 A RU2011152113/04 A RU 2011152113/04A RU 2011152113 A RU2011152113 A RU 2011152113A RU 2011152113 A RU2011152113 A RU 2011152113A
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diseases
hydrogen
alkoxy
trifluoromethyl
halogen
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RU2011152113/04A
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RU2497809C2 (en
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Сяньпин ЛУ
Чжибинь ЛИ
Сун ШАНЬ
Цзиньди ЮЙ
Чжицян НИН
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Шэньчжэнь Чипскрин Байосайенсиз, Лтд.
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Priority claimed from PCT/CN2010/000272 external-priority patent/WO2010139180A1/en
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1. Соединение формулы I1. The compound of formula I
Figure 00000001
Figure 00000001
 включая его свободную форму, солевую форму, стереоизомер, энантиомер, диастереомер или гидрат,including its free form, salt form, stereoisomer, enantiomer, diastereomer or hydrate, гдеWhere Z представляет CH или N;Z represents CH or N; каждая из групп R1, R2 и R3 представляет водород, галоген, алкил, алкокси или трифторметил;each of the groups R 1 , R 2 and R 3 represents hydrogen, halogen, alkyl, alkoxy or trifluoromethyl; R4 представляетR 4 represents
Figure 00000002
или
Figure 00000003
Figure 00000002
or
Figure 00000003
 X представляет бензольное кольцо или пиридиновое кольцо;X represents a benzene ring or a pyridine ring; R5 представляет один или более заместителей, выбранных из группы, состоящей из водорода, галогена, алкила, алкокси и трифторметила.R 5 represents one or more substituents selected from the group consisting of hydrogen, halogen, alkyl, alkoxy and trifluoromethyl. 2. Соединение по п.1, где2. The compound according to claim 1, where Z представляет CH;Z represents CH; каждая из групп R1, R2 и R3 представляет водород, галоген, алкил, алкокси или трифторметил;each of the groups R 1 , R 2 and R 3 represents hydrogen, halogen, alkyl, alkoxy or trifluoromethyl; R4 представляетR 4 represents
Figure 00000002
или
Figure 00000003
Figure 00000002
or
Figure 00000003
 X представляет бензольное кольцо или пиридиновое кольцо;X represents a benzene ring or a pyridine ring; R5 представляет один или более заместителей, выбранных из группы, состоящей из водорода, галогена, алкила, алкокси и трифторметила.R 5 represents one or more substituents selected from the group consisting of hydrogen, halogen, alkyl, alkoxy and trifluoromethyl. 3. Соединение по п.1, где3. The compound according to claim 1, where Z представляет CH;Z represents CH; каждая из групп R1, R2 и R3 представляет водород или алкокси;each of the groups R 1 , R 2 and R 3 represents hydrogen or alkoxy; R4 представляетR 4 represents
Figure 00000002
или
Figure 00000003
Figure 00000002
or
Figure 00000003
 X представляет бензольное кольцо или пиридиновое кольцо;X represents a benzene ring or a pyridine ring; R5 представляет один или более заместителей, выбранных из группы, состоящей из водорода, галогена, алкила, алкокси и трифторметила.R 5 represents one or more substituents selected from the group consisting of hydrogen, halogen, alkyl, alkoxy and trifluoromethyl. 4. Соединение по п.1, где4. The compound according to claim 1, where Z представляет CH;Z represents CH; каждая из групп R1 и R2 представляет водород или метокси;each of the groups R 1 and R 2 represents hydrogen or methoxy; R3 представляет H;R 3 represents H; R4 представляетR 4 represents
Figure 00000002
или
Figure 00000003
Figure 00000002
or
Figure 00000003
 X представляет бензольное кольцо или пиридиновое кольцо;X represents a benzene ring or a pyridine ring; R5 представляет один или более заместителей, выбранных из группы, состоящей из водорода, галогена, алкила, алкокси и трифторметила.R 5 represents one or more substituents selected from the group consisting of hydrogen, halogen, alkyl, alkoxy and trifluoromethyl. 5. Соединение по п.1, где5. The compound according to claim 1, where Z представляет CH;Z represents CH; каждая из групп R1 и R2 представляет водород или метокси;each of the groups R 1 and R 2 represents hydrogen or methoxy; R3 представляет H;R 3 represents H; R4 представляетR 4 represents
Figure 00000002
или
Figure 00000003
Figure 00000002
or
Figure 00000003
 X представляет бензольное кольцо или пиридиновое кольцо;X represents a benzene ring or a pyridine ring; R5 представляет H или F.R 5 represents H or F. 6. Способ получения соединения формулы I6. A method of obtaining a compound of formula I
Figure 00000001
Figure 00000001
 гдеWhere Z представляет CH или N;Z represents CH or N; каждая из групп R1, R2 и R3 представляет водород, галоген, алкил, алкокси или трифторметил;each of the groups R 1 , R 2 and R 3 represents hydrogen, halogen, alkyl, alkoxy or trifluoromethyl; R4 представляетR 4 represents
Figure 00000002
или
Figure 00000003
Figure 00000002
or
Figure 00000003
 X представляет бензольное кольцо или пиридиновое кольцо;X represents a benzene ring or a pyridine ring; R5 представляет один или более заместителей, выбранных из группы, состоящей из водорода, галогена, алкила, алкокси и трифторметила;R 5 represents one or more substituents selected from the group consisting of hydrogen, halogen, alkyl, alkoxy and trifluoromethyl; включающий взаимодействиеinvolving interaction соединения формулы (II)compounds of formula (II)
Figure 00000004
Figure 00000004
 с соединением формулы (III)with a compound of formula (III)
Figure 00000005
Figure 00000005
 в присутствии органического растворителя и пептидного конденсирующего агента, для образования соединения формулы (I).in the presence of an organic solvent and a peptide condensing agent, to form a compound of formula (I). 7. Способ по п.6, где указанный пептидный конденсирующий агент выбран из группы, состоящей из 1-этил-3-(3-диметиламинопропил)карбодиимида (EDC), N,N'-дициклогексилкарбодиимида (DCC) и N,N'-карбонилдиимидазола (CDI).7. The method according to claim 6, where the specified peptide condensing agent is selected from the group consisting of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide (EDC), N, N'-dicyclohexylcarbodiimide (DCC) and N, N'- carbonyldiimidazole (CDI). 8. Способ по п.6, где указанный органический растворитель выбран из группы, состоящей из бензола, толуола, тетрагидрофурана, 1,4-диоксана, дихлорметана, хлороформа и N,N-диметилформамида.8. The method according to claim 6, where the specified organic solvent is selected from the group consisting of benzene, toluene, tetrahydrofuran, 1,4-dioxane, dichloromethane, chloroform and N, N-dimethylformamide. 9. Фармацевтический препарат для лечения заболеваний, связанных с аномальной активностью протеинкиназы или аномальной активностью гистондеацетилазы, включающий соединение формулы (I) по п.1 и фармацевтически приемлемый носитель, эксципиент или разбавитель.9. A pharmaceutical preparation for treating diseases associated with abnormal protein kinase activity or abnormal histone deacetylase activity, comprising a compound of formula (I) according to claim 1 and a pharmaceutically acceptable carrier, excipient or diluent. 10. Фармацевтический препарат по п.9 в форме таблетки, капсулы, порошка, сиропа, раствора, суспензии, инъекции или мази.10. The pharmaceutical preparation according to claim 9 in the form of a tablet, capsule, powder, syrup, solution, suspension, injection or ointment. 11. Применение соединения по п.1 при получении лекарственного средства для лечения воспалительных заболеваний, аутоиммунных заболеваний, онкологических заболеваний, заболеваний нервной системы и нейродегенеративных заболеваний, аллергий, астмы, сердечнососудистых заболеваний и метаболических заболевания или заболеваний, связанных с гормональными расстройствами.11. The use of the compound according to claim 1 in the manufacture of a medicament for the treatment of inflammatory diseases, autoimmune diseases, oncological diseases, diseases of the nervous system and neurodegenerative diseases, allergies, asthma, cardiovascular diseases and metabolic diseases or diseases associated with hormonal disorders. 12. Применение фармацевтического препарата по п.9 при получении лекарственного средства для лечения воспалительных заболеваний, аутоиммунных заболеваний, онкологических заболеваний, заболеваний нервной системы и нейродегенеративных заболеваний, аллергий, астмы, сердечнососудистых заболеваний и метаболических заболевания или заболеваний, связанных с гормональными расстройствами.12. The use of the pharmaceutical preparation according to claim 9 in the preparation of a medicament for the treatment of inflammatory diseases, autoimmune diseases, cancer, nervous system diseases and neurodegenerative diseases, allergies, asthma, cardiovascular diseases and metabolic diseases or diseases associated with hormonal disorders. 13. Фармацевтический препарат по п.9, содержащий указанное соединение формулы (I) в количестве в диапазоне от 0,001 до 200 мг. 13. The pharmaceutical preparation according to claim 9, containing the specified compound of formula (I) in an amount in the range from 0.001 to 200 mg.
RU2011152113/04A 2009-06-04 2010-03-05 Naphthalene carboxamide derivatives as protein kinase and histone deacetylase inhibitors, methods for preparing and using them RU2497809C2 (en)

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Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011057661A (en) * 2009-08-14 2011-03-24 Bayer Cropscience Ag Pesticidal carboxamides
CN102260210B (en) * 2011-05-30 2012-06-27 王立强 Preparation method of naphthoyl amine derivatives of protein kinase inhibitor and histone deacetylase inhibitor
CN102603627B (en) * 2011-05-31 2013-02-06 王立强 Naphthlamide derivative used as protein kinase inhibitor and histone deacetylase inhibitor and preparation method of naphthlamide derivative
CN102850236B (en) * 2011-06-27 2016-05-18 国药一心制药有限公司 New benzamides histone deacetylases inhibitor and application thereof
CN103420923B (en) * 2012-05-18 2015-08-19 国药一心制药有限公司 4-amido quinazoline hydroxamic acid compound and applying as antitumor drug
CN103288728A (en) * 2013-05-17 2013-09-11 华侨大学 Naphthoyl amine derivative, and preparation method and application thereof
CN103351336A (en) * 2013-06-28 2013-10-16 华侨大学 Naphthalenecarboxamide derivative as inhibitors of protein kinase and histone deacetylase and preparation method thereof
CN103432077A (en) * 2013-08-21 2013-12-11 北京淦航医药科技有限公司 Chidamide solid dispersion preparation
CN104418867B (en) * 2013-08-26 2016-12-28 上海汇伦生命科技有限公司 As the compound of PI3K/mTOR inhibitor, Preparation Method And The Use
CN103724260A (en) * 2013-12-18 2014-04-16 华侨大学 Benzamide derivative and preparation method and application thereof
CN104860885B (en) * 2014-02-24 2017-11-17 中国科学院上海药物研究所 Naphthoyl aminated compounds, preparation method and use
CN103896836A (en) * 2014-03-20 2014-07-02 华侨大学 N-benzyl-6-[(7-chloroquinoline-4-oxo) phenolic ether]-2-naphthamide and preparation method thereof
CN103923004A (en) * 2014-04-04 2014-07-16 华侨大学 Naphthalene formamide derivative and preparation and application thereof
CN104030980A (en) * 2014-06-10 2014-09-10 华侨大学 N-(3-methoxyl-4-chlorphenyl)-4-[(7-chloro-4-quinoline) amino] benzamide, preparation and application thereof
CN105399685B (en) * 2014-09-16 2018-05-22 深圳微芯生物科技有限责任公司 The alternatively preparation method and applications of the heteroaromatic compounds of property JAK3 and/or JAK1 kinase inhibitors
CN104447534A (en) * 2014-12-04 2015-03-25 厦门大学 6-[(7-chloroquinoline-4-oxyl) phenolic ether]-2-naphthamide derivative as well as preparation method and application thereof
CN107868044B (en) 2016-09-27 2020-10-16 深圳微芯生物科技股份有限公司 Non-solvation crystal and preparation method and application thereof
CN109803645B (en) * 2017-04-10 2022-03-25 师健友 A medicine for treating tumor and having antibacterial, antiviral and antiinflammatory effects
CN109985039A (en) * 2017-12-29 2019-07-09 深圳微芯生物科技股份有限公司 For treating the combination medicine of leukaemia and its preparing the purposes in the drug for treating acute myeloid leukaemia
CN114681455A (en) * 2018-08-17 2022-07-01 深圳微芯生物科技股份有限公司 Combination of histone deacetylase inhibitor and protein kinase inhibitor and pharmaceutical application thereof
CN109908143B (en) * 2018-12-18 2021-11-19 厦门大学附属第一医院 New application of seolonide in preparation of medicine for treating acute myeloid leukemia
TW202332445A (en) * 2019-03-25 2023-08-16 大陸商深圳微芯生物科技股份有限公司 Use of chiauranib in treating small cell lung cancer
CN113440615A (en) * 2020-03-24 2021-09-28 深圳微芯生物科技股份有限公司 Pharmaceutical composition comprising a protein kinase inhibitor and a chemotherapeutic drug and uses thereof
CN114246864A (en) * 2020-09-23 2022-03-29 上海润石医药科技有限公司 CSF1R kinase inhibitors and uses thereof
WO2022247844A1 (en) * 2021-05-26 2022-12-01 深圳微芯生物科技股份有限公司 Pharmaceutical composition containing protein kinase inhibitor and medical use thereof

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6174905B1 (en) 1996-09-30 2001-01-16 Mitsui Chemicals, Inc. Cell differentiation inducer
US6316429B1 (en) 1997-05-07 2001-11-13 Sugen, Inc. Bicyclic protein kinase inhibitors
JP4405602B2 (en) * 1998-04-16 2010-01-27 バイエル・シエーリング・ファーマ アクチエンゲゼルシャフト Histone deacetylase inhibitor
WO2001018171A2 (en) 1999-09-08 2001-03-15 Sloan-Kettering Institute For Cancer Research Novel class of cytodifferentiating agents and histone deacetylase inhibitors, and methods of use thereof
WO2001060814A2 (en) 2000-02-15 2001-08-23 Sugen, Inc. Pyrrole substituted 2-indolinone protein kinase inhibitors
CA2404002A1 (en) 2000-03-24 2001-09-27 Methylgene, Inc. Inhibitors of histone deacetylase
CA2407799A1 (en) 2000-05-02 2001-11-08 Sugen, Inc. (2-oxindol-3-ylidenyl)acetic acid derivatives and their use as protein kinase inhibitors
PE20020506A1 (en) 2000-08-22 2002-07-09 Glaxo Group Ltd PIRAZOLE DERIVATIVES FUSED AS PROTEIN KINASE INHIBITORS
CA2422371C (en) 2000-09-15 2010-05-18 Vertex Pharmaceuticals Incorporated Pyrazole compounds useful as protein kinase inhibitors
DE60138658D1 (en) 2000-09-29 2009-06-18 Topotarget Uk Ltd Carbamic acid derivatives containing an amide group for the treatment of malaria
US20020103192A1 (en) 2000-10-26 2002-08-01 Curtin Michael L. Inhibitors of histone deacetylase
AR042586A1 (en) 2001-02-15 2005-06-29 Sugen Inc 3- (4-AMIDOPIRROL-2-ILMETILIDEN) -2-INDOLINONE AS INHIBITORS OF PROTEIN KINASE; YOUR PHARMACEUTICAL COMPOSITIONS; A METHOD FOR THE MODULATION OF THE CATALYTIC ACTIVITY OF PROTEINQUINASE; A METHOD TO TREAT OR PREVENT AN AFFECTION RELATED TO PROTEINQUINASE
EP1429765A2 (en) * 2001-09-14 2004-06-23 Methylgene, Inc. Inhibitors of histone deacetylase
TW200306819A (en) 2002-01-25 2003-12-01 Vertex Pharma Indazole compounds useful as protein kinase inhibitors
TWI319387B (en) * 2002-04-05 2010-01-11 Astrazeneca Ab Benzamide derivatives
ATE404564T1 (en) 2003-01-09 2008-08-15 Pfizer DIAZEPINOINDOL DERIVATIVES AS KINASE INHIBITORS
WO2004078682A2 (en) 2003-03-05 2004-09-16 Irm Llc Cyclic compounds and compositions as protein kinase inhibitors
CA2536253A1 (en) 2003-08-20 2005-03-03 Vertex Pharmaceuticals Incorporated Aminofurazan compounds useful as protein kinase inhibitors
BRPI0414011A (en) * 2003-08-29 2006-10-24 Pfizer naphthalencarboxamides and their derivatives useful as new antiangiogenic agents
BRPI0507373A (en) * 2004-01-23 2007-07-10 Amgen Inc compounds and method of use
EP2060565A1 (en) * 2007-11-16 2009-05-20 4Sc Ag Novel bifunctional compounds which inhibit protein kinases and histone deacetylases

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