KR101218213B1 - 카스파제의 활성인자 및 세포자멸사의 유도인자로서의4-아릴아미노-퀴나졸린 - Google Patents

카스파제의 활성인자 및 세포자멸사의 유도인자로서의4-아릴아미노-퀴나졸린 Download PDF

Info

Publication number
KR101218213B1
KR101218213B1 KR1020067000187A KR20067000187A KR101218213B1 KR 101218213 B1 KR101218213 B1 KR 101218213B1 KR 1020067000187 A KR1020067000187 A KR 1020067000187A KR 20067000187 A KR20067000187 A KR 20067000187A KR 101218213 B1 KR101218213 B1 KR 101218213B1
Authority
KR
South Korea
Prior art keywords
alkyl
methyl
halo
independently
alkoxy
Prior art date
Application number
KR1020067000187A
Other languages
English (en)
Korean (ko)
Other versions
KR20060052775A (ko
Inventor
쑤이 슝 차이
닐란타 수다쓰 시리소마
아즈라 퍼빈
존 에이 드루
사일라자 카시바틀라
쑹춘 장
훙 장
크리스 플레이맨
비제이 베이치월
존 만프레디
리나 보이트
Original Assignee
시토비아 인크.
미리어드 제네틱스, 인크.
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 시토비아 인크., 미리어드 제네틱스, 인크. filed Critical 시토비아 인크.
Publication of KR20060052775A publication Critical patent/KR20060052775A/ko
Application granted granted Critical
Publication of KR101218213B1 publication Critical patent/KR101218213B1/ko

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72Quinazolines; Hydrogenated quinazolines
    • C07D239/86Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
    • C07D239/94Nitrogen atoms
    • 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
    • A61K31/495Heterocyclic 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
    • A61K31/517Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10Antimycotics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • A61P37/06Immunosuppressants, e.g. drugs for graft rejection
    • 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72Quinazolines; Hydrogenated quinazolines
    • C07D239/95Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
    • 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
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • 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
    • C07D471/02Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D473/00Heterocyclic compounds containing purine ring systems
    • C07D473/26Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
    • C07D473/32Nitrogen atom
    • C07D473/34Nitrogen atom attached in position 6, e.g. adenine
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • 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
    • C07D487/04Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Immunology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Virology (AREA)
  • Transplantation (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Quinoline Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Cephalosporin Compounds (AREA)
KR1020067000187A 2003-07-03 2004-07-06 카스파제의 활성인자 및 세포자멸사의 유도인자로서의4-아릴아미노-퀴나졸린 KR101218213B1 (ko)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
US48432503P 2003-07-03 2003-07-03
US60/484,325 2003-07-03
US49300603P 2003-08-07 2003-08-07
US60/493,006 2003-08-07
US55755604P 2004-03-29 2004-03-29
US60/557,556 2004-03-29
US57128804P 2004-05-14 2004-05-14
US60/571,288 2004-05-14

Publications (2)

Publication Number Publication Date
KR20060052775A KR20060052775A (ko) 2006-05-19
KR101218213B1 true KR101218213B1 (ko) 2013-01-04

Family

ID=33568832

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020067000187A KR101218213B1 (ko) 2003-07-03 2004-07-06 카스파제의 활성인자 및 세포자멸사의 유도인자로서의4-아릴아미노-퀴나졸린

Country Status (9)

Country Link
US (7) US7618975B2 (US20070244113A1-20071018-C00138.png)
EP (1) EP1660092A2 (US20070244113A1-20071018-C00138.png)
JP (2) JP5129957B2 (US20070244113A1-20071018-C00138.png)
KR (1) KR101218213B1 (US20070244113A1-20071018-C00138.png)
CN (1) CN1984660B (US20070244113A1-20071018-C00138.png)
AU (1) AU2004253967B2 (US20070244113A1-20071018-C00138.png)
CA (1) CA2531327A1 (US20070244113A1-20071018-C00138.png)
NZ (1) NZ544472A (US20070244113A1-20071018-C00138.png)
WO (1) WO2005003100A2 (US20070244113A1-20071018-C00138.png)

Families Citing this family (82)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7344702B2 (en) * 2004-02-13 2008-03-18 Bristol-Myers Squibb Pharma Company Contrast agents for myocardial perfusion imaging
US8309562B2 (en) * 2003-07-03 2012-11-13 Myrexis, Inc. Compounds and therapeutical use thereof
US7618975B2 (en) * 2003-07-03 2009-11-17 Myriad Pharmaceuticals, Inc. 4-arylamino-quinazolines and analogs as activators of caspases and inducers of apoptosis and the use thereof
WO2005048953A2 (en) 2003-11-13 2005-06-02 Ambit Biosciences Corporation Amide derivatives as kinase modulators
US20060128696A1 (en) 2004-05-15 2006-06-15 Annamaria Vezzani Treating seizures using ice inhibitors
US7531570B2 (en) 2004-05-27 2009-05-12 Vertex Pharmaceuticals Incorporated Treatment of diseases using ICE inhibitors
US20070244114A1 (en) * 2004-07-06 2007-10-18 Myriad Genetics, Incorporated Compounds and therapeutical use thereof
KR20060079121A (ko) * 2004-12-31 2006-07-05 에스케이케미칼주식회사 당뇨 및 비만 치료예방에 유효한 퀴나졸린 유도체
WO2006074187A2 (en) * 2005-01-03 2006-07-13 Myriad Genetics, Inc. Method of treating brain cancer
US8258145B2 (en) * 2005-01-03 2012-09-04 Myrexis, Inc. Method of treating brain cancer
CA2592900A1 (en) * 2005-01-03 2006-07-13 Myriad Genetics Inc. Nitrogen containing bicyclic compounds and therapeutical use thereof
CA2611712C (en) * 2005-06-14 2014-05-13 Baylor University Combretastatin analogs with tubulin binding activity
AU2006259261B2 (en) * 2005-06-16 2013-06-13 Myrexis, Inc. Pharmaceutical compositions and use thereof
WO2007011618A1 (en) * 2005-07-15 2007-01-25 Schering Corporation Quinazoline derivatives useful in cancer treatment
WO2007028162A2 (en) * 2005-09-02 2007-03-08 The University Of Toledo Methods and compositions for identifying biomarkers useful in diagnosis and/or treatment of biological states
ES2395386T3 (es) 2005-12-21 2013-02-12 Abbott Laboratories Compuestos antivirales
ATE541844T1 (de) * 2005-12-21 2012-02-15 Abbott Lab Antivirale verbindungen
JP2009521460A (ja) * 2005-12-21 2009-06-04 アボット・ラボラトリーズ 抗ウイルス化合物
PL2010496T3 (pl) * 2006-04-14 2011-01-31 Astrazeneca Ab 4-Anilinochinolino-3-karboksyamidy jako inhibitory kinazy CSF-1R
CN101547922B (zh) * 2006-10-04 2012-06-20 辉瑞产品公司 作为钙受体拮抗剂的吡啶并[4,3-d]嘧啶-4(3H)-酮衍生物
CA2672737A1 (en) 2006-12-20 2008-11-06 Abbott Laboratories Anti-viral compounds
EP2144888A4 (en) * 2007-04-10 2012-10-03 Myrexis Inc METHODS OF TREATING CANCER
WO2008124828A1 (en) * 2007-04-10 2008-10-16 Myriad Genetics, Inc. Methods for treating vascular disruption disorders
EP2144887A4 (en) * 2007-04-10 2012-10-03 Myrexis Inc PHARMACEUTICAL FORMS AND METHOD FOR THE TREATMENT OF CANCER
WO2008124822A1 (en) * 2007-04-10 2008-10-16 Myriad Genetics, Inc. Method of treating brain cancer
EP2144886A4 (en) * 2007-04-10 2012-10-03 Myrexis Inc METHOD OF TREATING MELANOMA
WO2008157500A1 (en) * 2007-06-17 2008-12-24 Kalypsys, Inc. Aminoquinazoline cannabinoid receptor modulators for treatment of disease
KR20100023862A (ko) * 2007-06-22 2010-03-04 싸이도우스 엘엘씨. 트윈 80을 함유하지 않은 도세탁셀의 용해 제제
US20100068197A1 (en) * 2008-07-11 2010-03-18 Myriad Pharmaceuticals, Inc. Pharmaceutical compounds as inhibitors of cell proliferation and the use thereof
NZ590913A (en) * 2008-07-11 2012-09-28 Myrexis Inc (2-aminomethylquinazolin-4-yl)-(4-methoxyphenyl)methylamine for treating or ameliorating neoplasm or cancer
CN101463014B (zh) * 2008-12-26 2013-07-10 复旦大学 二芳基苯并嘧啶类衍生物及其药物组合物和用途
JP5779172B2 (ja) 2009-04-02 2015-09-16 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung オートタキシン阻害剤
LT3575288T (lt) 2009-09-03 2021-12-10 Bristol-Myers Squibb Company Chinazolinai kaip kalio jonų kanalų inhibitoriai
US7772274B1 (en) 2009-10-19 2010-08-10 Scidose, Llc Docetaxel formulations with lipoic acid
US20110092579A1 (en) * 2009-10-19 2011-04-21 Scidose Llc Solubilized formulation of docetaxel
US8541465B2 (en) * 2009-10-19 2013-09-24 Scidose, Llc Docetaxel formulations with lipoic acid and/or dihydrolipoic acid
US8912228B2 (en) 2009-10-19 2014-12-16 Scidose Llc Docetaxel formulations with lipoic acid
CN101716351B (zh) * 2009-12-08 2012-04-11 中国人民解放军军事医学科学院野战输血研究所 一类吡啶化合物在制备rna干涉增强剂中的应用
US20110224240A1 (en) * 2010-01-11 2011-09-15 Myrexis, Inc. Methods of treating cancer and related diseases
JP6092628B2 (ja) 2010-02-08 2017-03-08 ランセウス メディカル イメージング, インコーポレイテッド 造影剤およびその中間体を合成するための方法および装置
CA2799653A1 (en) 2010-06-04 2011-12-08 Bertrand Leblond Substituted isoquinolines and their use as tubulin polymerization inhibitors
WO2012061786A1 (en) 2010-11-05 2012-05-10 Brandeis University Ice cleaved alpha-synuclein a biomarker
US8754114B2 (en) 2010-12-22 2014-06-17 Incyte Corporation Substituted imidazopyridazines and benzimidazoles as inhibitors of FGFR3
US9139590B2 (en) * 2011-02-04 2015-09-22 Duquesne University Of The Holy Spirit Bicyclic and tricyclic pyrimidine tyrosine kinase inhibitors with antitubulin activity and methods of treating a patient
CA2829131C (en) * 2011-03-04 2018-11-20 Glaxosmithkline Intellectual Property (No.2) Limited Amino-quinolines as kinase inhibitors
TWI547494B (zh) 2011-08-18 2016-09-01 葛蘭素史克智慧財產發展有限公司 作為激酶抑制劑之胺基喹唑啉類
PT3176170T (pt) 2012-06-13 2019-02-05 Incyte Holdings Corp Compostos tricíclicos substituídos como inibidores de fgfr
AU2013203000B9 (en) 2012-08-10 2017-02-02 Lantheus Medical Imaging, Inc. Compositions, methods, and systems for the synthesis and use of imaging agents
TWI592417B (zh) 2012-09-13 2017-07-21 葛蘭素史克智慧財產發展有限公司 胺基喹唑啉激酶抑制劑之前藥
TW201425307A (zh) 2012-09-13 2014-07-01 Glaxosmithkline Llc 作為激酶抑制劑之胺基-喹啉類
CN105143208B (zh) 2013-02-21 2017-09-26 葛兰素史密斯克莱知识产权发展有限公司 作为激酶抑制剂的喹唑啉
EP2769723A1 (en) 2013-02-22 2014-08-27 Ruprecht-Karls-Universität Heidelberg Compounds for use in inhibiting HIV capsid assembly
EP2769722A1 (en) 2013-02-22 2014-08-27 Ruprecht-Karls-Universität Heidelberg Compounds for use in inhibiting HIV capsid assembly
SG10201708520YA (en) 2013-04-19 2017-12-28 Incyte Corp Bicyclic heterocycles as fgfr inhibitors
CN104130200B (zh) * 2014-07-01 2016-04-20 中山大学 一种2-取代苯基-4-芳胺基喹唑啉衍生物及其制备方法和应用
US10851105B2 (en) 2014-10-22 2020-12-01 Incyte Corporation Bicyclic heterocycles as FGFR4 inhibitors
TWI712601B (zh) 2015-02-20 2020-12-11 美商英塞特公司 作為fgfr抑制劑之雙環雜環
MA41551A (fr) 2015-02-20 2017-12-26 Incyte Corp Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4
WO2016168704A1 (en) * 2015-04-16 2016-10-20 Icahn School Of Medicine At Mount Sinai Ksr antagonists
JP2019527725A (ja) * 2016-08-15 2019-10-03 パデュー リサーチ ファウンデイション 4位置換アミノイソキノリン誘導体
CN106380465B (zh) * 2016-09-05 2019-03-12 郑州大学 含1,2,3-三氮唑结构单元的2,4-二取代喹唑啉类化合物及其制备方法和用途
CN108239071B (zh) * 2016-12-27 2020-12-04 沈阳药科大学 酰胺及硫代酰胺类衍生物及其制备方法和应用
AR111960A1 (es) 2017-05-26 2019-09-04 Incyte Corp Formas cristalinas de un inhibidor de fgfr y procesos para su preparación
JP2020526495A (ja) * 2017-06-30 2020-08-31 ザ ユニバーシティ オブ ノース カロライナ アット チャペル ヒル ヘテロクロマチン遺伝子抑制阻害薬
MA52493A (fr) 2018-05-04 2021-03-10 Incyte Corp Sels d'un inhibiteur de fgfr
US11466004B2 (en) 2018-05-04 2022-10-11 Incyte Corporation Solid forms of an FGFR inhibitor and processes for preparing the same
US11628162B2 (en) 2019-03-08 2023-04-18 Incyte Corporation Methods of treating cancer with an FGFR inhibitor
US11591329B2 (en) 2019-07-09 2023-02-28 Incyte Corporation Bicyclic heterocycles as FGFR inhibitors
CA3157361A1 (en) 2019-10-14 2021-04-22 Incyte Corporation Bicyclic heterocycles as fgfr inhibitors
US11566028B2 (en) 2019-10-16 2023-01-31 Incyte Corporation Bicyclic heterocycles as FGFR inhibitors
JP2023505258A (ja) 2019-12-04 2023-02-08 インサイト・コーポレイション Fgfr阻害剤としての三環式複素環
BR112022010664A2 (pt) 2019-12-04 2022-08-16 Incyte Corp Derivados de um inibidor de fgfr
US11753413B2 (en) 2020-06-19 2023-09-12 Incyte Corporation Substituted pyrrolo[2,1-f][1,2,4]triazine compounds as JAK2 V617F inhibitors
WO2021257857A1 (en) 2020-06-19 2021-12-23 Incyte Corporation Naphthyridinone compounds as jak2 v617f inhibitors
WO2022006456A1 (en) 2020-07-02 2022-01-06 Incyte Corporation Tricyclic pyridone compounds as jak2 v617f inhibitors
AU2021300429A1 (en) 2020-07-02 2023-02-16 Incyte Corporation Tricyclic urea compounds as JAK2 V617F inhibitors
US11661422B2 (en) 2020-08-27 2023-05-30 Incyte Corporation Tricyclic urea compounds as JAK2 V617F inhibitors
US11919908B2 (en) 2020-12-21 2024-03-05 Incyte Corporation Substituted pyrrolo[2,3-d]pyrimidine compounds as JAK2 V617F inhibitors
TW202302589A (zh) 2021-02-25 2023-01-16 美商英塞特公司 作為jak2 v617f抑制劑之螺環內醯胺
EP4352059A1 (en) 2021-06-09 2024-04-17 Incyte Corporation Tricyclic heterocycles as fgfr inhibitors
CN115772130A (zh) * 2021-09-08 2023-03-10 四川大学华西医院 一种微管解聚剂及其制备方法和用途
CN114436975B (zh) * 2022-01-26 2023-10-31 贵州省中国科学院天然产物化学重点实验室(贵州医科大学天然产物化学重点实验室) 2-三氟甲基-4-氨基喹唑啉类化合物及其应用

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992014716A1 (en) * 1991-02-20 1992-09-03 Pfizer Inc. 2,4-diaminoquinazolines derivatives for enhancing antitumor activity
WO1995015758A1 (en) * 1993-12-10 1995-06-15 Rhone-Poulenc Rorer Pharmaceuticals Inc. Aryl and heteroaryl quinazoline compounds which inhibit csf-1r receptor tyrosine kinase

Family Cites Families (109)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2883382A (en) 1957-08-29 1959-04-21 Parke Davis & Co Benzo-quinolylamino-2-[di(beta-chloroethyl)aminomethyl]-phenols
US3031450A (en) 1959-04-30 1962-04-24 Thomae Gmbh Dr K Substituted pyrimido-[5, 4-d]-pyrimidines
CH423785A (de) 1960-02-02 1966-11-15 Thomae Gmbh Dr K Verfahren zur Herstellung von substituierten Pyrimidincarbonsäuren-(4)
US3502681A (en) 1968-04-10 1970-03-24 Roussel Uclaf 7- or 8-chloro-4-phenylamino-chloroquinolines
FR8491M (US20070244113A1-20071018-C00138.png) 1968-12-31 1973-07-27
BE754586A (fr) 1969-08-08 1971-02-08 Upjohn Co Preparations pharmaceutiques a base de p-(4-quinolylamino) benzamide etleur utilisation
US3971783A (en) 1973-03-07 1976-07-27 Pfizer Inc. 4-Aminoquinazoline derivatives as cardiac stimulants
US4025629A (en) 1974-01-07 1977-05-24 The Upjohn Company P-(trifluoromethylquinolylamino)benzamides, pharmaceutical dosage forms and method of treatment
JPS5538325A (en) * 1978-09-11 1980-03-17 Sankyo Co Ltd 4-anilinoquinazoline derivative and its preparation
DE2918591A1 (de) * 1979-05-09 1980-11-20 Hoechst Ag Neue 4-substituierte 5,6,7,8-tetrahydrochinoline, ihre herstellung und verwendung
FI70036C (fi) 1980-01-31 1986-09-12 Ciba Geigy Ag Kromogena kinazolinfoereningar
NZ197420A (en) 1980-07-01 1984-04-27 Ici Australia Ltd -(quinazolin-(2-or 4-)(oxy,ylthio or amino)phen(oxy or ylthio)alkanoic acid derivatives
US4510307A (en) 1980-08-20 1985-04-09 Asahi Kasei Kogyo Kabushiki Kaisha 6-Quinazolinesulfonyl derivatives and process for preparation thereof
DE3049207A1 (de) 1980-12-27 1982-07-29 Dr. Karl Thomae Gmbh, 7950 Biberach Neue trisubstituierte pyrimido (5,4-d) pyrimidine, ihre herstellung und ihre verwendung als arzneimittel
FR2498187A1 (fr) 1981-01-16 1982-07-23 Rhone Poulenc Sante Procede de preparation d'amino-4 chloro-7 quinoleines
DE3423092A1 (de) 1984-06-22 1986-01-02 Dr. Karl Thomae Gmbh, 7950 Biberach Neue 8-alkylthio-2-piperazino-pyrimido(5,4-d) pyrimidine, ihre herstellung und diese verbindungen enthaltende arzneimittel
IL88507A (en) * 1987-12-03 1993-02-21 Smithkline Beckman Intercredit 2,4-diaminoquinazolines, process for their preparation and pharmaceutical compositions comprising them
IL89029A (en) 1988-01-29 1993-01-31 Lilly Co Eli Fungicidal quinoline and cinnoline derivatives, compositions containing them, and fungicidal methods of using them
US5294622A (en) 1988-01-29 1994-03-15 Dowelanco Substituted quinolines and cinnolines
US5114939A (en) 1988-01-29 1992-05-19 Dowelanco Substituted quinolines and cinnolines as fungicides
IE63502B1 (en) 1989-04-21 1995-05-03 Zeneca Ltd Aminopyrimidine derivatives useful for treating cardiovascular disorders
GB8910722D0 (en) * 1989-05-10 1989-06-28 Smithkline Beckman Intercredit Compounds
CA2015981A1 (en) * 1989-05-10 1990-11-10 Thomas H. Brown Compounds
GB9008818D0 (en) 1990-04-19 1990-06-13 Ici Plc Amine derivatives
DE4029648A1 (de) * 1990-09-19 1992-03-26 Hoechst Ag 4-anilino-pyrimidine, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung als fungizide
US5480883A (en) 1991-05-10 1996-01-02 Rhone-Poulenc Rorer Pharmaceuticals Inc. Bis mono- and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase
US6645969B1 (en) * 1991-05-10 2003-11-11 Aventis Pharmaceuticals Inc. Aryl and heteroaryl quinazoline compounds which inhibit CSF-1R receptor tyrosine kinase
DE69222637T2 (de) 1991-05-10 1998-02-26 Rhone Poulenc Rorer Int Bis mono- und bicyclische aryl- und heteroarylderivate mit inhibierender wirkung auf die egf und/oder pdgf-rezeptor tyrosinkinase
USRE37650E1 (en) 1991-05-10 2002-04-09 Aventis Pharmacetical Products, Inc. Aryl and heteroaryl quinazoline compounds which inhibit CSF-1R receptor tyrosine kinase
US5714493A (en) 1991-05-10 1998-02-03 Rhone-Poulenc Rorer Pharmaceuticals, Inc. Aryl and heteroaryl quinazoline compounds which inhibit CSF-1R receptor tyrosine kinase
US5721237A (en) 1991-05-10 1998-02-24 Rhone-Poulenc Rorer Pharmaceuticals Inc. Protein tyrosine kinase aryl and heteroaryl quinazoline compounds having selective inhibition of HER-2 autophosphorylation properties
DE4116785A1 (de) 1991-05-23 1992-11-26 Basf Ag Phenylazo- oder naphthylazobenzole mit mehreren reaktiven ankern
US5236925A (en) 1991-10-24 1993-08-17 American Home Products Corporation Fused pyrimidines as angiotensin II antagonists
US5187168A (en) 1991-10-24 1993-02-16 American Home Products Corporation Substituted quinazolines as angiotensin II antagonists
US5256781A (en) 1991-10-24 1993-10-26 American Home Products Corporation Substituted quinazolines as angiotensin II antagonists
US5330989A (en) 1991-10-24 1994-07-19 American Home Products Corporation Heterocycles substituted with biphenyl-3-cyclobutene-1,2-dione derivatives
GB9127252D0 (en) 1991-12-23 1992-02-19 Boots Co Plc Therapeutic agents
TW215434B (US20070244113A1-20071018-C00138.png) 1992-03-07 1993-11-01 Hoechst Ag
US5270466A (en) 1992-06-11 1993-12-14 American Cyanamid Company Substituted quinazoline fungicidal agents
JP2657760B2 (ja) 1992-07-15 1997-09-24 小野薬品工業株式会社 4−アミノキナゾリン誘導体およびそれを含有する医薬品
US5565472A (en) 1992-12-21 1996-10-15 Pfizer Inc. 4-aryl-3-(heteroarylureido)-1,2-dihydro-2-oxo-quinoline derivatives as antihypercholesterolemic and antiatherosclerotic agents
US5618829A (en) 1993-01-28 1997-04-08 Mitsubishi Chemical Corporation Tyrosine kinase inhibitors and benzoylacrylamide derivatives
DK60593D0 (da) 1993-05-26 1993-05-26 Novo Nordisk As Kemiske forbindelser, deres fremstilling og anvendelse
US6087160A (en) 1993-06-24 2000-07-11 The General Hospital Corporation Programmed cell death genes and proteins
DE4325900A1 (de) * 1993-08-02 1995-02-09 Thomae Gmbh Dr K Trisubstituierte Pyrimido [5,4-d] pyrimidine zur Modulation der Multidrugresistenz, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
US5656643A (en) 1993-11-08 1997-08-12 Rhone-Poulenc Rorer Pharmaceuticals Inc. Bis mono-and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase
IL112249A (en) 1994-01-25 2001-11-25 Warner Lambert Co Pharmaceutical compositions containing di and tricyclic pyrimidine derivatives for inhibiting tyrosine kinases of the epidermal growth factor receptor family and some new such compounds
US5679683A (en) 1994-01-25 1997-10-21 Warner-Lambert Company Tricyclic compounds capable of inhibiting tyrosine kinases of the epidermal growth factor receptor family
EP0754672B1 (en) 1994-04-06 2000-10-11 Shionogi & Co., Ltd. Gamma-substituted phenylacetic acid derivative, process for producing the same, and agricultural bactericide containing the same
US6313150B1 (en) 1994-04-06 2001-11-06 Shionogi & Co., Ltd. α-substituted phenylacetic acid derivative, its production and agricultural fungicide containing it
TW414798B (en) 1994-09-07 2000-12-11 Thomae Gmbh Dr K Pyrimido (5,4-d) pyrimidines, medicaments comprising these compounds, their use and processes for their preparation
ATE225351T1 (de) 1994-11-08 2002-10-15 Takeda Chemical Industries Ltd Thienopyridin und thienopyrimidinderivate und ihre verwendung als entzündungshemmende mittel
US5747498A (en) 1996-05-28 1998-05-05 Pfizer Inc. Alkynyl and azido-substituted 4-anilinoquinazolines
US6232312B1 (en) 1995-06-07 2001-05-15 Cell Pathways, Inc. Method for treating patient having precancerous lesions with a combination of pyrimidopyrimidine derivatives and esters and amides of substituted indenyl acetic acides
US5965740A (en) 1995-09-29 1999-10-12 Shionogi & Co., Ltd. Alpha-substituted benzyl heterocyclic derivatives, intermediates for producing the same and pesticides containing the same as active ingredient
SI0892789T2 (sl) * 1996-04-12 2010-03-31 Warner Lambert Co Ireverzibilni inhibitorji tirozin kinaz
DE69717627T2 (de) 1996-06-27 2003-09-18 Janssen Pharmaceutica Nv N-4-(heteroarylmethyl)phenyl-heteroarylaminderivate
ID19609A (id) 1996-07-13 1998-07-23 Glaxo Group Ltd Senyawa-senyawa heterosiklik
US5874738A (en) * 1996-07-16 1999-02-23 Saint-Gobain Industrial Ceramics, Inc. Scintillation crystal modules and methods of making the same
ATE232863T1 (de) 1996-08-06 2003-03-15 Pfizer Substituierte pyrido- oder pyrimidogruppen enthaltende 6,6- oder 6,7-bicyclische derivate
US5874438A (en) 1996-10-11 1999-02-23 Bayer Aktiengesellschaft 2,2'-bridged bis-2,4-diaminoquinazolines
US5760230A (en) 1996-10-11 1998-06-02 Bayer Aktiengesellschaft 4, 4'-bridged bis-2, 4-diaminoquinazolines
PT835659E (pt) 1996-10-14 2005-03-31 Aventis Pharma Gmbh Utilizacao de antagonistas nao petidicos da bradiquinina para a preparacao de medicamentos para o tratamento e prevencao da doenca de alzheimer
US5739127A (en) 1996-11-08 1998-04-14 Bayer Aktiengesellschaft 2,4'-bridged bis-2,4-diaminoquinazolines
US6552055B2 (en) * 1996-12-11 2003-04-22 Dana-Farber Cancer Institute Methods and pharmaceutical compositions for inhibiting tumor cell growth
DE69739828D1 (de) * 1996-12-11 2010-05-12 Dana Farber Cancer Inst Inc Methoden und pharmazeutische Zusammensetzungen zur Inhibition des Tumorwachstums
US6002008A (en) 1997-04-03 1999-12-14 American Cyanamid Company Substituted 3-cyano quinolines
AR012634A1 (es) 1997-05-02 2000-11-08 Sugen Inc Compuesto basado en quinazolina, composicion famaceutica que lo comprende, metodo para sintetizarlo, su uso, metodos de modulacion de la funcion deserina/treonina proteinaquinasa con dicho compuesto y metodo in vitro para identificar compuestos que modulan dicha funcion
ZA986732B (en) 1997-07-29 1999-02-02 Warner Lambert Co Irreversible inhibitiors of tyrosine kinases
US6251912B1 (en) 1997-08-01 2001-06-26 American Cyanamid Company Substituted quinazoline derivatives
WO1999009986A1 (fr) * 1997-08-22 1999-03-04 Kyowa Hakko Kogyo Co., Ltd. Derives de 4-aminoquinazoline
IL135365A0 (en) 1997-10-10 2001-05-20 Cytovia Inc Fluorescent reporter compounds and methods utilizing the same
US6242196B1 (en) 1997-12-11 2001-06-05 Dana-Farber Cancer Institute Methods and pharmaceutical compositions for inhibiting tumor cell growth
PT1037629E (pt) 1997-12-19 2005-03-31 Janssen Pharmaceutica Nv Combinacao de um ramba e um tocoferol
US20020025968A1 (en) * 1998-04-15 2002-02-28 Rifat Pamukcu Method for inhibiting neoplastic cells and related conditions by exposure to 4-aminoquinazoline derivatives
WO1999061428A1 (en) 1998-05-28 1999-12-02 Parker Hughes Institute Quinazolines for treating brain tumor
US6800649B1 (en) * 1998-06-30 2004-10-05 Parker Hughes Institute Method for inhibiting c-jun expression using JAK-3 inhibitors
US6313129B1 (en) 1998-08-21 2001-11-06 Hughes Institute Therapeutic compounds
US6184226B1 (en) 1998-08-28 2001-02-06 Scios Inc. Quinazoline derivatives as inhibitors of P-38 α
US6297258B1 (en) 1998-09-29 2001-10-02 American Cyanamid Company Substituted 3-cyanoquinolines
KR20010086073A (ko) * 1998-12-02 2001-09-07 데이비드 존 우드 p53계 단백질의 배좌 안정성을 회복하기 위한 방법 및조성물
UA71945C2 (en) 1999-01-27 2005-01-17 Pfizer Prod Inc Substituted bicyclic derivatives being used as anticancer agents
US6080747A (en) 1999-03-05 2000-06-27 Hughes Institute JAK-3 inhibitors for treating allergic disorders
RS49836B (sr) 1999-03-31 2008-08-07 Pfizer Products Inc., Postupci i intermedijeri za dobijanje anti-kancernih jedinjenja
US6518283B1 (en) 1999-05-28 2003-02-11 Celltech R&D Limited Squaric acid derivatives
US6432979B1 (en) 1999-08-12 2002-08-13 American Cyanamid Company Method of treating or inhibiting colonic polyps and colorectal cancer
US20030149045A1 (en) * 1999-08-20 2003-08-07 Fatih M Uckun Therapeutic compounds
US7087613B2 (en) * 1999-11-11 2006-08-08 Osi Pharmaceuticals, Inc. Treating abnormal cell growth with a stable polymorph of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine hydrochloride
US6384051B1 (en) 2000-03-13 2002-05-07 American Cyanamid Company Method of treating or inhibiting colonic polyps
GEP20063831B (en) * 2000-06-22 2006-05-25 Pfizer Prod Inc Substituted bicyclic derivatives for treatment of abnormal cell growth
US6740651B2 (en) * 2000-08-26 2004-05-25 Boehringer Ingelheim Pharma Kg Aminoquinazolines which inhibit signal transduction mediated by tyrosine kinases
US20020082270A1 (en) * 2000-08-26 2002-06-27 Frank Himmelsbach Aminoquinazolines which inhibit signal transduction mediated by tyrosine kinases
AU2002212697A1 (en) * 2000-11-02 2002-05-15 Nippon Shinyaku Co. Ltd. Quinazoline derivatives and drugs
US20040034045A1 (en) * 2000-11-29 2004-02-19 Parker Hughes Institute Inhibitors of thrombin induced platelet aggregation
AU2002228922A1 (en) * 2000-12-12 2002-06-24 Cytovia, Inc. Substituted 2-aryl-4-arylaminopyrimidines and analogs as activators of caspases and inducers of apoptosis and the use thereof
KR100947185B1 (ko) * 2000-12-21 2010-03-15 버텍스 파마슈티칼스 인코포레이티드 단백질 키나제 억제제로서 유용한 피라졸 화합물 및 이를 포함하는 조성물
US20030134836A1 (en) * 2001-01-12 2003-07-17 Amgen Inc. Substituted arylamine derivatives and methods of use
WO2002070662A2 (en) * 2001-03-02 2002-09-12 Gpc Biotech Ag Three hybrid assay system
US6562319B2 (en) * 2001-03-12 2003-05-13 Yissum Research Development Company Of The Hebrew University Of Jerusalem Radiolabeled irreversible inhibitors of epidermal growth factor receptor tyrosine kinase and their use in radioimaging and radiotherapy
US6887873B2 (en) * 2001-03-23 2005-05-03 Aventis Pharma S.A. Triazine derivatives and their application as antitelomerase agents
US6864255B2 (en) * 2001-04-11 2005-03-08 Amgen Inc. Substituted triazinyl amide derivatives and methods of use
US6883375B2 (en) * 2001-06-29 2005-04-26 Harold L. Dunegan Detection of movement of termites in wood by acoustic emission techniques
ATE377009T1 (de) * 2001-11-30 2007-11-15 Osi Pharm Inc Verfahren für die herstellung substituierter bicyclischer derivate zur behandlung von anomalem zellwachstum
DE10204462A1 (de) * 2002-02-05 2003-08-07 Boehringer Ingelheim Pharma Verwendung von Tyrosinkinase-Inhibitoren zur Behandlung inflammatorischer Prozesse
WO2003097615A1 (en) * 2002-05-17 2003-11-27 Scios, Inc. TREATMENT OF FIBROPROLIFERATIVE DISORDERS USING TGF-β INHIBITORS
AU2004218456A1 (en) * 2003-02-28 2004-09-16 Encysive Pharmaceuticals Inc. Pyridine, pyrimidine, quinoline, quinazoline, and naphthalene urotensin-II receptor antagonists.
US7618975B2 (en) * 2003-07-03 2009-11-17 Myriad Pharmaceuticals, Inc. 4-arylamino-quinazolines and analogs as activators of caspases and inducers of apoptosis and the use thereof
SI1678166T1 (sl) * 2003-10-14 2009-10-31 Univ Arizona State Inhibitorji proteinske kinaze
CA2592900A1 (en) * 2005-01-03 2006-07-13 Myriad Genetics Inc. Nitrogen containing bicyclic compounds and therapeutical use thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992014716A1 (en) * 1991-02-20 1992-09-03 Pfizer Inc. 2,4-diaminoquinazolines derivatives for enhancing antitumor activity
WO1995015758A1 (en) * 1993-12-10 1995-06-15 Rhone-Poulenc Rorer Pharmaceuticals Inc. Aryl and heteroaryl quinazoline compounds which inhibit csf-1r receptor tyrosine kinase

Also Published As

Publication number Publication date
US20070208044A1 (en) 2007-09-06
KR20060052775A (ko) 2006-05-19
CN1984660A (zh) 2007-06-20
US20080032974A1 (en) 2008-02-07
JP2012207044A (ja) 2012-10-25
WO2005003100A2 (en) 2005-01-13
AU2004253967B2 (en) 2010-02-18
EP1660092A2 (en) 2006-05-31
CA2531327A1 (en) 2005-01-13
US20070249601A1 (en) 2007-10-25
US20070244113A1 (en) 2007-10-18
US20170050937A1 (en) 2017-02-23
US7618975B2 (en) 2009-11-17
US20080039479A1 (en) 2008-02-14
JP2007524637A (ja) 2007-08-30
WO2005003100A3 (en) 2005-05-12
NZ544472A (en) 2009-04-30
AU2004253967A1 (en) 2005-01-13
US20050137213A1 (en) 2005-06-23
AU2004253967A8 (en) 2010-02-04
JP5129957B2 (ja) 2013-01-30
CN1984660B (zh) 2010-12-15

Similar Documents

Publication Publication Date Title
KR101218213B1 (ko) 카스파제의 활성인자 및 세포자멸사의 유도인자로서의4-아릴아미노-퀴나졸린
US8309562B2 (en) Compounds and therapeutical use thereof
US7989462B2 (en) 4-arylamin-or-4-heteroarylamino-quinazolines and analogs as activators of caspases and inducers of apoptosis and the use thereof
EP0823901B1 (en) Quinazoline derivative
US6015814A (en) Quinazoline derivative
KR100622323B1 (ko) 질소-함유헤테로고리화합물
EP1107959B1 (en) Quinazoline derivatives as medicaments
US8258145B2 (en) Method of treating brain cancer
HU223313B1 (hu) Kinazolinszármazékok, ezeket tartalmazó gyógyszerkészítmények és eljárás előállításukra
CA2592971A1 (en) Method of treating brain cancer
CA2593005A1 (en) Pharmaceutical compounds as activators of caspases and inducers of apoptosis and the use thereof
US20070244114A1 (en) Compounds and therapeutical use thereof
Jain et al. An explicative review on the progress of quinazoline scaffold as bioactive agents in the past decade
Yilmaz Synthesis and biological studies of some 3-substituted-2, 4 (1H, 3H)-quinazolinedione derivatives

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
E902 Notification of reason for refusal
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 20151217

Year of fee payment: 4

FPAY Annual fee payment

Payment date: 20161129

Year of fee payment: 5

LAPS Lapse due to unpaid annual fee