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

Info

Publication number
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
Authority
CN
China
Prior art keywords
methyl
indol
hydroxybenzamide
ylsulfanyl
tetrahydropyrazino
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CN201280058930.1A
Other languages
English (en)
Chinese (zh)
Other versions
CN103974956A (zh
Inventor
王召印
李连海
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
NANJING AOZHAO BIOTECHNOLOGY Co Ltd
Original Assignee
NANJING AOZHAO BIOTECHNOLOGY Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by NANJING AOZHAO BIOTECHNOLOGY Co Ltd filed Critical NANJING AOZHAO BIOTECHNOLOGY Co Ltd
Publication of CN103974956A publication Critical patent/CN103974956A/zh
Application granted granted Critical
Publication of CN103974956B publication Critical patent/CN103974956B/zh
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61N—ELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY
    • A61N5/00—Radiation therapy
    • A61N5/10—X-ray therapy; Gamma-ray therapy; Particle-irradiation therapy
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic 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
    • A61K31/403—Heterocyclic 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic 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
    • A61K31/407—Heterocyclic 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic 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
    • A61K31/4353—Heterocyclic 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
    • A61K31/437—Heterocyclic 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic 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
    • A61K31/498—Pyrazines or piperazines ortho- and peri-condensed with carbocyclic ring systems, e.g. quinoxaline, phenazine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic 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
    • A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic 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
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic 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
    • C07D471/02—Heterocyclic 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
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic 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
    • C07D471/12—Heterocyclic 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
    • C07D471/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic 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
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/12—Heterocyclic 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
    • C07D495/14—Ortho-condensed systems

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Immunology (AREA)
  • Radiology & Medical Imaging (AREA)
  • Pathology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Tropical Medicine & Parasitology (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

Publications (2)

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

Family

ID=48534555

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201280058930.1A Expired - Fee Related CN103974956B (zh) 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

Country Status (6)

Country Link
US (1) US9345905B2 (enExample)
EP (1) EP2785720B1 (enExample)
JP (1) JP6272773B2 (enExample)
CN (1) CN103974956B (enExample)
CA (1) CA2857193A1 (enExample)
WO (1) WO2013078544A1 (enExample)

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
TR201900057T4 (tr) * 2013-12-12 2019-01-21 Chong Kun Dang Pharmaceutical Corp Selektif histon deasetilaz (HDAC) inhibitörleri olarak yeni azaindol deriveleri ve bunları içeren farmasötik bileşimler.
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
WO2016020369A1 (en) * 2014-08-04 2016-02-11 Universität Regensburg Novel hdac6 inhibitors and their uses
MY197262A (en) 2015-07-27 2023-06-08 Chong Kun Dang Pharmaceutical Corp 1,3,4-oxadiazole sulfonamide derivative compounds as histone deacetylase 6 inhibitor, and the pharmaceutical composition comprising the same
US10584117B2 (en) 2015-07-27 2020-03-10 Chong Kun Dang Pharmaceutical Corp. 1,3,4-oxadiazole amide derivative compound as histone deacetylase 6 inhibitor, and pharmaceutical composition containing same
CN107980040B (zh) 2015-07-27 2021-11-26 株式会社钟根堂 作为组蛋白去乙酰酶6抑制剂的1,3,4-噁二唑磺酰胺衍生物及含其的医药组合物
HRP20220003T1 (hr) * 2015-08-04 2022-04-01 Chong Kun Dang Pharmaceutical Corp. Spojevi derivata 1,3,4-oksadiazola kao inhibitori histonske deacetilaze 6, i farmaceutski pripravak koji ih sadrži
HUE061967T2 (hu) 2015-10-12 2023-09-28 Chong Kun Dang Pharmaceutical Corp Hiszton deacetiláz-6 inhibitor oxadiazol-amin származékok és az azokat tartalmazó gyógyászati készítmény
CN109153643B (zh) * 2016-03-04 2022-06-21 范德比尔特大学 取代的吲哚mcl-1抑制剂
JP7542947B2 (ja) * 2016-10-28 2024-09-02 アセチロン ファーマシューティカルズ インコーポレイテッド ヒストン脱アセチル化酵素阻害剤及びエポチロンを含む医薬品組み合わせならびにその使用方法
US11535598B2 (en) 2017-05-16 2022-12-27 Annji Pharmaceutical Co., Ltd. Histone deacetylases (HDACs) inhibitors
JOP20180094A1 (ar) 2017-10-18 2019-04-18 Hk Inno N Corp مركب حلقي غير متجانس كمثبط بروتين كيناز
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
CA3136223C (en) 2019-05-31 2023-09-12 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
IL307883A (en) 2021-04-23 2023-12-01 Tenaya Therapeutics Inc HDAC6 inhibitors for use in the treatment of dilated myocardial disease
EP4333841A1 (en) 2021-05-04 2024-03-13 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
US20080194681A1 (en) * 2004-12-09 2008-08-14 Kalypsys, Inc. Novel Inhibitors of Histone Deacetylase for the Treatment of Disease
EP2190845A2 (en) * 2007-08-21 2010-06-02 ArQule, Inc. Hdac inhibitors
EP2217588A4 (en) * 2007-11-02 2013-12-04 Methylgene Inc INHIBITORS OF HISTONE DEACETYLASE
CA2932121A1 (en) * 2007-11-30 2009-06-11 Newlink Genetics Corporation Ido inhibitors
US8207165B2 (en) * 2008-03-28 2012-06-26 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.
CA2846066A1 (en) * 2011-10-28 2013-05-02 Chong Kun Dang Pharmaceutical Corp. Hydroxamate derivatives for hdac inhibitor, and the pharmaceutical composition comprising thereof

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

Also Published As

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

Similar Documents

Publication Publication Date Title
CN103974956B (zh) 作为hdac6抑制剂和用作抗肿瘤剂的杂环酰胺化合物
CA2863239C (en) Cyclic molecules as bruton's tyrosine kinase inhibitors
US8633204B2 (en) 4-methylpyridopyrimidinone compounds
WO2013185202A1 (en) Apoptosis inducers
CN107849012B (zh) 一类激酶抑制剂
US9226923B2 (en) Spirocyclic molecules as protein kinase inhibitors
CN113710671B (zh) 作为布鲁顿酪氨酸激酶抑制剂的环状分子
US8946445B2 (en) Heterocyclic molecules as apoptosis inducers
JP2016504394A (ja) 抗がん剤としてのゲム−ジふっ化ｃ−グリコシド化合物
HK40056349A (en) Cyclic molecules as bruton's tyrosine kinase inhibitor

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20160706

Termination date: 20211129

CF01 Termination of patent right due to non-payment of annual fee