KR101837974B1 - 8-하이드록시-퀴놀린 유도체 - Google Patents

8-하이드록시-퀴놀린 유도체 Download PDF

Info

Publication number
KR101837974B1
KR101837974B1 KR1020127030702A KR20127030702A KR101837974B1 KR 101837974 B1 KR101837974 B1 KR 101837974B1 KR 1020127030702 A KR1020127030702 A KR 1020127030702A KR 20127030702 A KR20127030702 A KR 20127030702A KR 101837974 B1 KR101837974 B1 KR 101837974B1
Authority
KR
South Korea
Prior art keywords
group
methyl
compound
quinolin
trifluoromethyl
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.)
Active
Application number
KR1020127030702A
Other languages
English (en)
Korean (ko)
Other versions
KR20130029772A (ko
Inventor
라슬로 푸스카스
크사바 스자보
아이반 카니즈샤
마리오 가그리스
레모나 마닥시
벨라 오즈스바리
릴리아나 패헐
가볼 타마스
Original Assignee
"아비딘" 쿠타토, 페레즈토 에스 케레스켈데미 코라톨트 펠레로세구 타르사사그
우비켐 쿠타토 콜라톨트 페레로쎄구 탈사사그
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 "아비딘" 쿠타토, 페레즈토 에스 케레스켈데미 코라톨트 펠레로세구 타르사사그, 우비켐 쿠타토 콜라톨트 페레로쎄구 탈사사그 filed Critical "아비딘" 쿠타토, 페레즈토 에스 케레스켈데미 코라톨트 펠레로세구 타르사사그
Publication of KR20130029772A publication Critical patent/KR20130029772A/ko
Application granted granted Critical
Publication of KR101837974B1 publication Critical patent/KR101837974B1/ko
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A61K31/47Quinolines; Isoquinolines
    • A61K31/4709Non-condensed quinolines and containing further heterocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
    • A61P13/12Drugs for disorders of the urinary system of the kidneys
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/02Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/18Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/22Anxiolytics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/24Antidepressants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/28Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00General protective or antinoxious agents
    • A61P39/06Free radical scavengers or antioxidants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20Oxygen atoms
    • C07D215/24Oxygen atoms attached in position 8
    • C07D215/26Alcohols; Ethers thereof
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Psychiatry (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Urology & Nephrology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Vascular Medicine (AREA)
  • Dermatology (AREA)
  • Pulmonology (AREA)
  • Epidemiology (AREA)
  • Biochemistry (AREA)
  • Toxicology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pain & Pain Management (AREA)
  • Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Quinoline Compounds (AREA)
KR1020127030702A 2010-05-06 2011-05-06 8-하이드록시-퀴놀린 유도체 Active KR101837974B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
HU1000243A HUP1000243A2 (en) 2010-05-06 2010-05-06 8-hidroxy-quinoline derivatives
HUP1000243 2010-05-06
PCT/HU2011/000043 WO2011148208A1 (en) 2010-05-06 2011-05-06 8-hydroxy-quinoline derivatives

Publications (2)

Publication Number Publication Date
KR20130029772A KR20130029772A (ko) 2013-03-25
KR101837974B1 true KR101837974B1 (ko) 2018-03-13

Family

ID=89989711

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020127030702A Active KR101837974B1 (ko) 2010-05-06 2011-05-06 8-하이드록시-퀴놀린 유도체

Country Status (21)

Country Link
US (1) US8871937B2 (enExample)
EP (1) EP2566849B1 (enExample)
JP (1) JP5812541B2 (enExample)
KR (1) KR101837974B1 (enExample)
CN (1) CN102985407B (enExample)
AU (1) AU2011256989B2 (enExample)
CA (1) CA2798419C (enExample)
CY (1) CY1122426T1 (enExample)
DK (1) DK2566849T3 (enExample)
EA (1) EA021026B1 (enExample)
ES (1) ES2761832T3 (enExample)
HR (1) HRP20192278T1 (enExample)
HU (2) HUP1000243A2 (enExample)
MX (1) MX337999B (enExample)
NZ (1) NZ603967A (enExample)
PL (1) PL2566849T3 (enExample)
PT (1) PT2566849T (enExample)
RS (1) RS59678B1 (enExample)
SI (1) SI2566849T1 (enExample)
SM (1) SMT201900710T1 (enExample)
WO (1) WO2011148208A1 (enExample)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HUP1500098A2 (hu) * 2015-03-09 2016-09-28 Avidin Kft 8-hidroxikinolin származékok új enantiomerjei és szintézisük
CA3001817A1 (en) * 2015-10-12 2017-04-20 Health Research, Inc. Methods for inducing apoptosis in cancer cells
CN105367553A (zh) * 2015-12-04 2016-03-02 广东工业大学 一种他克林-8-羟(胺)基喹啉衍生物及其应用
HUP1600234A2 (en) 2016-04-05 2017-12-28 Mta Termeszettudomanyi Kutatokoezpont Mdr-reversing 8-hydroxy-quinoline derivatives
WO2024073624A2 (en) * 2022-09-28 2024-04-04 The Research Foundation For The State University Of New York Antiproliferative betti bases and prodrugs thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009151972A1 (en) * 2008-05-28 2009-12-17 , The United States Of America, As Represented By The Secretary Of The Army, On Behalf Of U.S. Army Medical Research And Materiel Command Small molecule inhibitors of botulinum neurotoxins

Family Cites Families (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999015179A1 (en) 1997-09-25 1999-04-01 Regents Of The University Of Minnesota Methods of limiting apoptosis of cells
US6184210B1 (en) 1997-10-10 2001-02-06 Cytovia, Inc. Dipeptide apoptosis inhibitors and the use thereof
EP1051165A2 (en) 1998-01-26 2000-11-15 Mitokor Mitochondria protecting agents for treating mitochondria associated diseases
US6737511B1 (en) 1999-08-16 2004-05-18 The United States Of America As Represented By The Department Of Health And Human Services Receptor-mediated uptake of an extracellular BCL-xL fusion protein inhibits apoptosis
CN1235875C (zh) 1999-08-27 2006-01-11 西托维亚公司 取代的α-羟基酸天冬氨酸特异性半胱氨酸蛋白酶抑制剂及其用途
US6890896B1 (en) 1999-11-18 2005-05-10 Ceremedix, Inc. Compositions and methods for counteracting effects of reactive oxygen species and free radicals
US6476048B1 (en) 1999-12-07 2002-11-05 Inotek Pharamaceuticals Corporation Substituted phenanthridinones and methods of use thereof
US6531464B1 (en) 1999-12-07 2003-03-11 Inotek Pharmaceutical Corporation Methods for the treatment of neurodegenerative disorders using substituted phenanthridinone derivatives
US6534651B2 (en) 2000-04-06 2003-03-18 Inotek Pharmaceuticals Corp. 7-Substituted isoindolinone inhibitors of inflammation and reperfusion injury and methods of use thereof
GB0011095D0 (en) 2000-05-08 2000-06-28 Black James Foundation astrin and cholecystokinin receptor ligands (III)
US6521617B2 (en) 2000-10-13 2003-02-18 The Johns Hopkins University Treatment of apoptotic cell death
AU2002239595A1 (en) 2000-12-15 2002-06-24 Mitokor Compounds for altering mitochondrial function and cellular responses
US7601846B2 (en) 2001-06-26 2009-10-13 The Regents Of The University Of California Compounds having activity as inhibitors of apoptosis
ATE443131T1 (de) 2001-07-10 2009-10-15 Biogen Idec Inc Hemmung des apoptoseprozesses und verbesserung der zelleistung
DE10144153A1 (de) 2001-09-07 2003-03-27 Newfrey Llc Halteclip mit versetzten Rastfingern
BRPI0307673A2 (pt) 2002-02-13 2016-11-08 Beth Israel Hospital métodos de tratar doença vascular.
WO2005072295A2 (en) 2004-01-23 2005-08-11 Cornell Research Foundation, Inc. Methods for reducing oxidative damage
AU2004258801A1 (en) 2003-02-28 2005-02-03 Inotek Pharmaceuticals Corporation Tetracyclic Benzamide Derivatives and methods of use thereof
US7449464B2 (en) 2003-03-12 2008-11-11 Kudos Pharmaceuticals Limited Phthalazinone derivatives
ES2396334T3 (es) 2003-05-28 2013-02-20 Eisai Inc. Compuestos, métodos y composiciones farmacéuticas para la inhibición de PARP
TWI375673B (en) 2005-04-11 2012-11-01 Abbott Lab 1h-benzimidazole-4-carboxamides substituted with a quaternary carbon at the 2-position are potent parp inhibitors
ATE461923T1 (de) 2005-11-15 2010-04-15 Abbott Lab Substituierte 1h-benzimidazol-4-carbonsäureamide sind wirksame parp-inhibitoren
US7528174B2 (en) 2006-01-06 2009-05-05 University Of Pittsburgh-Of The Commonwealth System Of Higher Education Selective targeting agents for mitochondria
RU2009106461A (ru) * 2006-07-25 2010-08-27 Энвиво Фармасьютикалз, Инк. (Us) Хинолиновые производные
EP2139460A4 (en) * 2007-03-20 2011-09-07 Univ Brandeis COMPOSITIONS AND METHODS FOR THE DIAGNOSIS, TREATMENT AND PREVENTION OF AMYOTROPHER LATERAL SCLEROSIS AND ASSOCIATED NEUROLOGICAL DISEASES
US8183236B2 (en) * 2007-04-12 2012-05-22 University Of Southern California Compounds with HIV-1 integrase inhibitory activity and use thereof as anti-HIV/AIDS therapeutics
EP2148944A1 (en) 2007-05-25 2010-02-03 Burnham Institute for Medical Research Inhibitors of thapsigargin-induced cell death
US8138356B2 (en) * 2007-10-16 2012-03-20 Angiogeney, Inc. Chemical inhibitors of inhibitors of differentiation
US8658170B2 (en) * 2010-01-06 2014-02-25 Joseph P. Errico Combination therapy with MDM2 and EFGR inhibitors
WO2011085129A2 (en) * 2010-01-06 2011-07-14 Errico Joseph P Methods and compositions of targeted drug development

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009151972A1 (en) * 2008-05-28 2009-12-17 , The United States Of America, As Represented By The Secretary Of The Army, On Behalf Of U.S. Army Medical Research And Materiel Command Small molecule inhibitors of botulinum neurotoxins

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
Journal f. prakt. Chemie., Vol. 327, No. 5, pp.871-877 (1985)*
Journal of Organic Chemistry, Vol. 19, No. 6, pp.907-909 (1954)*
Journal of the American Chemistry Society, Vol. 75, No. 17, pp. 4306-4307 (1953)*
Molecular and Cellular Endocronology, Vol. 301, pp. 245-250 (2009)*

Also Published As

Publication number Publication date
SMT201900710T1 (it) 2020-01-14
HUE050886T2 (hu) 2021-01-28
EA021026B1 (ru) 2015-03-31
JP5812541B2 (ja) 2015-11-17
CA2798419A1 (en) 2011-12-01
CN102985407B (zh) 2015-09-09
WO2011148208A1 (en) 2011-12-01
RS59678B1 (sr) 2020-01-31
SI2566849T1 (sl) 2020-02-28
CY1122426T1 (el) 2021-01-27
US8871937B2 (en) 2014-10-28
EP2566849B1 (en) 2019-09-18
DK2566849T3 (da) 2020-01-02
ES2761832T3 (es) 2020-05-21
HUP1000243A2 (en) 2012-01-30
CA2798419C (en) 2021-01-05
HU1000243D0 (en) 2010-06-28
HRP20192278T1 (hr) 2020-03-06
US20130131096A1 (en) 2013-05-23
PT2566849T (pt) 2020-01-06
NZ603967A (en) 2014-06-27
AU2011256989B2 (en) 2014-08-21
EA201270787A1 (ru) 2013-04-30
PL2566849T3 (pl) 2020-03-31
KR20130029772A (ko) 2013-03-25
JP2013525473A (ja) 2013-06-20
AU2011256989A1 (en) 2013-01-10
MX337999B (es) 2016-03-30
EP2566849A1 (en) 2013-03-13
CN102985407A (zh) 2013-03-20
MX2012012883A (es) 2013-03-20

Similar Documents

Publication Publication Date Title
JP5001650B2 (ja) ベンズイミダゾールカルボキサミド
JP5094398B2 (ja) 複素環式誘導体およびステアロイル−CoAデサチュラーゼのメディエータとしてのそれらの使用
KR100554988B1 (ko) 2-아미노-니코틴아미드 유도체 및 그의 vegf-수용체티로신 키나제 억제제로서의 용도
EP3206689B1 (en) Inhibitors of low molecular weight protein tyrosine phosphatase and uses thereof
KR101837974B1 (ko) 8-하이드록시-퀴놀린 유도체
CN115057855B (zh) 取代五元并六元杂环类化合物、其制备方法、药物组合及其用途
JP2008513505A5 (enExample)
KR20160132470A (ko) 피페리딘-다이온 유도체
KR20140014313A (ko) 단백질 키나제 및 히스톤 디아세틸라제의 억제제로서 나프탈렌 카르복스아미드 유도체, 그 제조 방법 및 용도
HUE029370T2 (hu) Rákellenes aktivitású vegyületek
JP4823903B2 (ja) ベンズイミダゾール誘導体
EA019110B1 (ru) Замещенные хиназолиновые соединения
El-Gamal et al. New triarylpyrazoles as broad-spectrum anticancer agents: Design, synthesis, and biological evaluation
Qi et al. Synthesis and antimicrobial activity evaluation of pyrazole derivatives containing the imidazo [2, 1‐b][1, 3, 4] thiadiazole moiety
EP2880034B1 (en) Amino-heteroaryl 7-hydroxy-spiropiperidine indolinyl antagonists of p2y1 receptor
CN115974847B (zh) 3-(1,2,3-三氮唑-4-基)四氢喹唑啉-2,4-二酮类衍生物及其制法和应用
US20110098304A1 (en) Small molecule inhibitors of PARP activity
US9381260B2 (en) Hypoxia inducible factor-1 pathway inhibitors and uses as anticancer and imaging agents
KR102789906B1 (ko) 신규 피리미딘 유도체
CN111138366B (zh) 吡唑氨基甲酰类衍生物、及其制备方法和用途
JP4431796B2 (ja) 新規な抗マラリア剤
CN121693502A (zh) 新型嘧啶衍生物
WO2016001452A1 (en) Compounds, in particular for use in the treatment of a disease or condition for which a bromodomain inhibitor is indicated
KR20240057820A (ko) 신규 피라졸로-옥소티아졸리딘 유도체 및 이를 포함하는 알칼리성 포스파타제 억제제

Legal Events

Date Code Title Description
PA0105 International application

Patent event date: 20121123

Patent event code: PA01051R01D

Comment text: International Patent Application

PG1501 Laying open of application
A201 Request for examination
PA0201 Request for examination

Patent event code: PA02012R01D

Patent event date: 20160418

Comment text: Request for Examination of Application

E902 Notification of reason for refusal
PE0902 Notice of grounds for rejection

Comment text: Notification of reason for refusal

Patent event date: 20170227

Patent event code: PE09021S01D

E701 Decision to grant or registration of patent right
PE0701 Decision of registration

Patent event code: PE07011S01D

Comment text: Decision to Grant Registration

Patent event date: 20180125

GRNT Written decision to grant
PR0701 Registration of establishment

Comment text: Registration of Establishment

Patent event date: 20180307

Patent event code: PR07011E01D

PR1002 Payment of registration fee

Payment date: 20180308

End annual number: 3

Start annual number: 1

PG1601 Publication of registration
PR1001 Payment of annual fee

Payment date: 20210413

Start annual number: 4

End annual number: 4

PR1001 Payment of annual fee

Payment date: 20220506

Start annual number: 5

End annual number: 5

PR1001 Payment of annual fee

Payment date: 20230508

Start annual number: 6

End annual number: 6

PR1001 Payment of annual fee

Payment date: 20240304

Start annual number: 7

End annual number: 7

PR1001 Payment of annual fee

Payment date: 20250304

Start annual number: 8

End annual number: 8