CN103974956B - 作为hdac6抑制剂和用作抗肿瘤剂的杂环酰胺化合物 - Google Patents

作为hdac6抑制剂和用作抗肿瘤剂的杂环酰胺化合物 Download PDF

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CN103974956B
CN103974956B CN201280058930.1A CN201280058930A CN103974956B CN 103974956 B CN103974956 B CN 103974956B CN 201280058930 A CN201280058930 A CN 201280058930A CN 103974956 B CN103974956 B CN 103974956B
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methyl
indol
hydroxybenzamide
ylsulfanyl
tetrahydropyrazino
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CN103974956A (zh
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王召印
李连海
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NANJING AOZHAO BIOTECHNOLOGY Co Ltd
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NANJING AOZHAO BIOTECHNOLOGY Co Ltd
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61NELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY
    • A61N5/00Radiation therapy
    • A61N5/10X-ray therapy; Gamma-ray therapy; Particle-irradiation therapy
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/407Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • AHUMAN NECESSITIES
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    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/498Pyrazines or piperazines ortho- and peri-condensed with carbocyclic ring systems, e.g. quinoxaline, phenazine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4985Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
    • AHUMAN NECESSITIES
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    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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    • C07D471/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04Ortho-condensed systems
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/12Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
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    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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    • C07DHETEROCYCLIC COMPOUNDS
    • C07D495/00Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/12Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D495/14Ortho-condensed systems

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  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Pain & Pain Management (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CN201280058930.1A 2011-11-29 2012-11-29 作为hdac6抑制剂和用作抗肿瘤剂的杂环酰胺化合物 Expired - Fee Related CN103974956B (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201161629827P 2011-11-29 2011-11-29
US61/629,827 2011-11-29
PCT/CA2012/001101 WO2013078544A1 (en) 2011-11-29 2012-11-29 Heterocyclic amides compounds which are hdac6 inhibitors and used as anti-tumoral agents

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CN103974956A CN103974956A (zh) 2014-08-06
CN103974956B true CN103974956B (zh) 2016-07-06

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US (1) US9345905B2 (https=)
EP (1) EP2785720B1 (https=)
JP (1) JP6272773B2 (https=)
CN (1) CN103974956B (https=)
CA (1) CA2857193A1 (https=)
WO (1) WO2013078544A1 (https=)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2451686C1 (ru) * 2010-12-27 2012-05-27 Александр Васильевич Иващенко ЗАМЕЩЕННЫЕ ГИДРИРОВАННЫЕ ТИЕНО-ПИРРОЛО [3,2-c] ПИРИДИНЫ, ЛИГАНДЫ, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ И СПОСОБ ИХ ПРИМЕНЕНИЯ
ES2704704T3 (es) * 2013-12-12 2019-03-19 Chong Kun Dang Pharmaceutical Corp Nuevos derivados de azaindol como inhibidores selectivos de la histona desacetilasa (HDAC) y composiciones farmacéuticas que los comprenden
KR101685639B1 (ko) * 2014-01-03 2016-12-12 주식회사 종근당 신규한 인돌 유도체 화합물 및 이를 포함하는 약제학적 조성물
WO2015148854A1 (en) 2014-03-27 2015-10-01 Vanderbilt University Substituted indole mcl-1 inhibitors
US10106540B2 (en) 2014-08-04 2018-10-23 Universität Regensburg HDAC6 inhibitors and their uses
FI3328843T3 (fi) 2015-07-27 2023-01-31 1,3,4-oksadiatsolisulfonamidijohdannaisyhdisteitä histonideasetylaasi-6:n inhibiittoreina ja samaa käsittävä farmaseuttinen koostumus
DK3330259T3 (da) 2015-07-27 2020-08-10 Chong Kun Dang Pharmaceutical Corp 1,3,4-oxadiazolamidderivativ-forbindelse som histondeacetylase-6-inhibitor og farmaceutisk sammensætning indeholdende denne
ES2774510T3 (es) 2015-07-27 2020-07-21 Chong Kun Dang Pharmaceutical Corp Derivados de 1,3,4-oxadiazol sulfamida como inhibidores de histona desacetilasa 6 y composición farmacéutica que comprende los mismos
RU2709207C2 (ru) * 2015-08-04 2019-12-17 Чонг Кун Данг Фармасьютикал Корп. 1,3,4-оксадиазольные производные соединения в качестве ингибитора гистондеацетилазы 6 и фармацевтическая композиция, содержащая их
HRP20230201T1 (hr) 2015-10-12 2023-03-31 Chong Kun Dang Pharmaceutical Corp. Oksadiazol aminski spojevi derivati kao inhibitor histonske deacetilaze 6 i farmaceutska kompozicija koja sadrži iste
BR112018067775B1 (pt) * 2016-03-04 2024-02-15 Vanderbilt University Compostos inibidores de mcl-1 indol substituídos, composição farmacêutica compreendendo ditos compostos e usos terapêuticos dos mesmos
US11998546B2 (en) 2016-10-28 2024-06-04 Acetylon Pharmaceuticals, Inc. Pharmaceutical combinations comprising a histone deacetylase inhibitor and epothilone and methods of use thereof
CN110621317B (zh) 2017-05-16 2023-05-12 安基生技新药股份有限公司 组蛋白去乙酰化酶(hdacs)抑制剂
KR20190043437A (ko) 2017-10-18 2019-04-26 씨제이헬스케어 주식회사 단백질 키나제 억제제로서의 헤테로고리 화합물
KR102316234B1 (ko) 2018-07-26 2021-10-22 주식회사 종근당 히스톤 탈아세틸화효소 6 억제제로서의 1,3,4-옥사다이아졸 유도체 화합물 및 이를 포함하는 약제학적 조성물
KR102195348B1 (ko) 2018-11-15 2020-12-24 에이치케이이노엔 주식회사 단백질 키나제 억제제로서의 신규 화합물 및 이를 포함하는 약제학적 조성물
AU2020284606B2 (en) 2019-05-31 2023-01-19 Chong Kun Dang Pharmaceutical Corp. 1,3,4-oxadiazole homophthalimide derivative compounds as histone deacetylase 6 inhibitor, and the pharmaceutical composition comprising the same
AU2020407664A1 (en) 2019-12-20 2022-08-18 Tenaya Therapeutics, Inc. Fluoroalkyl-oxadiazoles and uses thereof
EP4326263A1 (en) 2021-04-23 2024-02-28 Tenaya Therapeutics, Inc. Hdac6 inhibitors for use in the treatment of dilated cardiomyopathy
AU2022270657A1 (en) 2021-05-04 2023-11-16 Tenaya Therapeutics, Inc. 2-fluoroalkyl-1,3,4-oxadiazol-5-yl-thiazol, hdac6 inhibitors for use in the treatment of metabolic disease and hfpef
CN113861193A (zh) * 2021-11-04 2021-12-31 西南大学 一种光引发自由基串联反应制备吲哚并四氢吡啶二酮及其衍生物的方法和产品
WO2025215092A1 (en) 2024-04-10 2025-10-16 Institut National de la Santé et de la Recherche Médicale Selective hdac6 inhibitors for use in the treatment of myotonic dystrophy type 1

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2597193A1 (en) * 2007-08-13 2009-02-13 De Montfort University Compounds and uses
CA2760541A1 (en) * 2009-04-29 2010-11-04 Medivation Technologies, Inc. Pyrido[4,3-b] indoles and methods of use
CA2768466A1 (en) * 2009-07-22 2011-01-27 The Board Of Trustees Of The University Of Illinois Hdac inhibitors and therapeutic methods using the same
CA2760516A1 (en) * 2009-04-29 2011-02-17 Medivation Technologies, Inc. Pyrido[4,3-b]indoles and methods of use

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006063294A2 (en) * 2004-12-09 2006-06-15 Kalypsys, Inc. Novel inhibitors of histone deacetylase for the treatment of disease
US20100261710A1 (en) * 2007-08-21 2010-10-14 Arqule, Inc. HDAC Inhibitors
BRPI0817897A2 (pt) * 2007-11-02 2019-09-24 Methylgene Inc composto, composição, e, métodos de inibição da atividade hdac, e de tratamento de uma doença responsiva a um inibidor de atividade hdac
JP5583592B2 (ja) * 2007-11-30 2014-09-03 ニューリンク ジェネティクス コーポレイション Ido阻害剤
EP2254886B1 (en) * 2008-03-28 2016-05-25 Nerviano Medical Sciences S.r.l. 3,4-dihydro-2h-pyrazino[1,2-a]indol-1-one derivatives active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them
US20110053925A1 (en) * 2009-08-28 2011-03-03 Novartis Ag Hydroxamate-Based Inhibitors of Deacetylases
IT1396915B1 (it) * 2009-10-23 2012-12-20 Italfarmaco Spa Dietil-[6-(4-idrossicarbamoil-fenil-carbamoilossimetil)-naftalen-2-il-metil]-ammonio cloruro ed altri derivati della n-idrossi-benzammide per l'uso nel trattamento di infezioni da hiv.
JP5771750B2 (ja) * 2011-10-28 2015-09-02 チョン クン ダン ファーマシューティカル コーポレーション Hdac阻害剤用のヒドロキサメート誘導体およびこれを含む薬学的組成物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2597193A1 (en) * 2007-08-13 2009-02-13 De Montfort University Compounds and uses
CA2760541A1 (en) * 2009-04-29 2010-11-04 Medivation Technologies, Inc. Pyrido[4,3-b] indoles and methods of use
CA2760516A1 (en) * 2009-04-29 2011-02-17 Medivation Technologies, Inc. Pyrido[4,3-b]indoles and methods of use
CA2768466A1 (en) * 2009-07-22 2011-01-27 The Board Of Trustees Of The University Of Illinois Hdac inhibitors and therapeutic methods using the same

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EP2785720A4 (en) 2015-11-11
WO2013078544A1 (en) 2013-06-06
EP2785720A1 (en) 2014-10-08
CN103974956A (zh) 2014-08-06
US9345905B2 (en) 2016-05-24
JP2014533734A (ja) 2014-12-15
US20140322229A1 (en) 2014-10-30
EP2785720B1 (en) 2017-08-09
CA2857193A1 (en) 2013-06-06
JP6272773B2 (ja) 2018-01-31

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