KR102276348B1 - Ｎ­（４­〔［６,７­비스（메틸옥시）퀴놀린­４­일］옥시〕페닐）­ｎ′­（４­플루오로페닐）시클로프로판­１,１­디카복사미드의 대사물 - Google Patents

Ｎ­（４­〔［６,７­비스（메틸옥시）퀴놀린­４­일］옥시〕페닐）­ｎ′­（４­플루오로페닐）시클로프로판­１,１­디카복사미드의 대사물 Download PDF

Info

Publication number
KR102276348B1
KR102276348B1 KR1020157027712A KR20157027712A KR102276348B1 KR 102276348 B1 KR102276348 B1 KR 102276348B1 KR 1020157027712 A KR1020157027712 A KR 1020157027712A KR 20157027712 A KR20157027712 A KR 20157027712A KR 102276348 B1 KR102276348 B1 KR 102276348B1
Authority
KR
South Korea
Prior art keywords
metabolite
compound
pharmaceutically acceptable
acceptable salt
caboxantinib
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
KR1020157027712A
Other languages
English (en)
Korean (ko)
Other versions
KR20150130376A (ko
Inventor
다나 티. 아프탭
스리람 나가나탄
웨이 수
스티븐 레이시
린 뉴엔
Original Assignee
엑셀리시스, 인코포레이티드
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 엑셀리시스, 인코포레이티드 filed Critical 엑셀리시스, 인코포레이티드
Publication of KR20150130376A publication Critical patent/KR20150130376A/ko
Application granted granted Critical
Publication of KR102276348B1 publication Critical patent/KR102276348B1/ko
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic 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
    • C07D215/16—Heterocyclic 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
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
    • 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
    • A61K31/47—Quinolines; Isoquinolines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C233/60—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C305/00—Esters of sulfuric acids
    • C07C305/22—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to carbon atoms of six-membered aromatic rings
    • C07C305/24—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to carbon atoms of six-membered aromatic rings of non-condensed six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/58—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems with hetero atoms directly attached to the ring nitrogen atom
    • C07D215/60—N-oxides
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/483—Physical analysis of biological material
    • G01N33/487—Physical analysis of biological material of liquid biological material
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N2570/00—Omics, e.g. proteomics, glycomics or lipidomics; Methods of analysis focusing on the entire complement of classes of biological molecules or subsets thereof, i.e. focusing on proteomes, glycomes or lipidomes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Physics & Mathematics (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Biophysics (AREA)
  • Pathology (AREA)
  • Immunology (AREA)
  • General Physics & Mathematics (AREA)
  • Biochemistry (AREA)
  • Analytical Chemistry (AREA)
  • Food Science & Technology (AREA)
  • Urology & Nephrology (AREA)
  • Hematology (AREA)
  • Molecular Biology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Epidemiology (AREA)
  • Saccharide Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Pain & Pain Management (AREA)
KR1020157027712A 2013-03-15 2014-03-17 Ｎ­（４­〔［６,７­비스（메틸옥시）퀴놀린­４­일］옥시〕페닐）­ｎ′­（４­플루오로페닐）시클로프로판­１,１­디카복사미드의 대사물 Active KR102276348B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201361792413P 2013-03-15 2013-03-15
US61/792,413 2013-03-15
PCT/US2014/030524 WO2014145715A1 (en) 2013-03-15 2014-03-17 Metabolites of n-(4-{[6,7-bis(methyloxy)quinolin-4-yl]oxy}phenyl)-n'-(4-fluorophenyl) cyclopropane-1,1-dicarboxamide

Publications (2)

Publication Number Publication Date
KR20150130376A KR20150130376A (ko) 2015-11-23
KR102276348B1 true KR102276348B1 (ko) 2021-07-12

Family

ID=50631091

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020157027712A Active KR102276348B1 (ko) 2013-03-15 2014-03-17 Ｎ­（４­〔［６,７­비스（메틸옥시）퀴놀린­４­일］옥시〕페닐）­ｎ′­（４­플루오로페닐）시클로프로판­１,１­디카복사미드의 대사물

Country Status (17)

Country Link
US (4) US10273211B2 (https=)
EP (1) EP2970126B1 (https=)
JP (1) JP6389238B2 (https=)
KR (1) KR102276348B1 (https=)
CN (1) CN105121412B (https=)
AU (2) AU2014232714B2 (https=)
BR (1) BR112015023109A2 (https=)
CA (1) CA2907334C (https=)
EA (1) EA033786B1 (https=)
ES (1) ES2729626T3 (https=)
GE (2) GEAP201913960A (https=)
IL (1) IL241577B (https=)
MX (1) MX366003B (https=)
NZ (1) NZ712330A (https=)
UA (1) UA119321C2 (https=)
WO (1) WO2014145715A1 (https=)
ZA (1) ZA201506842B (https=)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX352926B (es) 2010-09-27 2017-12-14 Exelixis Inc Inhibidores dobles de met y factor de crecimiento endotelial vascular (vegf) para el tratamiento de cancer de prostata resistente a la castracion y metastasis osteoblasticas en los huesos.
BR112013020362A2 (pt) 2011-02-10 2018-05-29 Exelixis Inc processos para a preparação de compostos de quinolina, compostos e combinações farmacêuticas que os contem
WO2013166296A1 (en) 2012-05-02 2013-11-07 Exelixis, Inc. A dual met - vegf modulator for treating osteolytic bone metastases
CA2907334C (en) 2013-03-15 2021-12-07 Exelixis, Inc. Metabolites of n-(4-{[6,7-bis(methyloxy)quinolin-4-yl]oxy}phenyl)-n'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide
US11564915B2 (en) 2013-04-04 2023-01-31 Exelixis, Inc. Cabozantinib dosage form and use in the treatment of cancer
BR112016018450A2 (pt) 2014-02-14 2018-09-18 Exelixis Inc formas sólidas cristalinas de n-{4-[(6,7-dimetoxiquinolin-4-il)oxi]fenil}-n'-(4-fluorofenil)ciclopropano-1,1-dicarboxamida, processos de preparo e métodos de uso
EP3119476A1 (en) * 2014-03-17 2017-01-25 Exelixis, Inc. Dosing of cabozantinib formulations
EP3174854B1 (en) * 2014-07-31 2022-08-24 Exelixis, Inc. Method of preparing fluorine-18 labeled cabozantinib and its analogs
MX382904B (es) 2014-08-05 2025-03-13 Exelixis Inc Combinaciones de fármacos para tratar mieloma múltiple.
EP3442531A1 (en) 2016-04-15 2019-02-20 Exelixis, Inc. Method of treating renal cell carcinoma using n-(4-(6,7-dimethoxyquinolin-4-yloxy) phenyl)-n'-(4-fluoropheny)cyclopropane-1,1-dicarboxamide, (2s)-hydroxybutanedioate
CN107556238A (zh) * 2016-06-30 2018-01-09 深圳万乐药业有限公司 一种卡博替尼的合成方法
CN117402114A (zh) 2018-01-26 2024-01-16 埃克塞里艾克西斯公司 用于治疗激酶依赖性病症的化合物
TWI831259B (zh) 2018-06-15 2024-02-01 漢達生技醫藥股份有限公司 包含達沙替尼十二烷基硫酸鹽組合物的膠囊
CN110423218A (zh) * 2019-08-09 2019-11-08 新乡双鹭药业有限公司 一种苹果酸卡博替尼合成中杂质的制备方法
CN120239695A (zh) * 2022-12-01 2025-07-01 江苏奥赛康药业有限公司 一种制备卡博替尼及其中间体的方法
WO2024163400A1 (en) 2023-01-31 2024-08-08 Handa Oncology, Llc Improved cabozantinib compositions and methods of use

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005030140A2 (en) * 2003-09-26 2005-04-07 Exelixis, Inc. C-met modulators and methods of use

Family Cites Families (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7977345B2 (en) 2004-07-02 2011-07-12 Exelixis, Inc. c-MET modulators and method of use
EP1874759A4 (en) 2005-04-06 2009-07-15 Exelixis Inc C-MET MODULATORS MODULATORS AND METHODS OF USE
UY30183A1 (es) 2006-03-02 2007-10-31 Astrazeneca Ab Derivados de quinolina
PL2101759T3 (pl) 2006-12-14 2019-05-31 Exelixis Inc Sposoby stosowania inhibitorów MEK
UY31800A (es) 2008-05-05 2009-11-10 Smithkline Beckman Corp Metodo de tratamiento de cancer usando un inhibidor de cmet y axl y un inhibidor de erbb
AR075084A1 (es) 2008-09-26 2011-03-09 Smithkline Beecham Corp Metodo de preparacion de quinolinil -oxidifenil - ciclopropanodicarboxamidas e intermediarios correspondientes
JP5486606B2 (ja) 2008-11-13 2014-05-07 エクセリクシス， インク． キノリン誘導体の調製方法
US20130030172A1 (en) 2008-12-04 2013-01-31 Exelixis, Inc. Methods of Preparing Quinoline Derivatives
NZ779754A (en) 2009-01-16 2023-04-28 Exelixis Inc Malate salt of n-(4-{ [6,7-bis(methyloxy)quinolin-4-yl] oxy} phenyl)-n’-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide, and crystalline forms thereof for the treatment of cancer
CN102510855B (zh) 2009-07-17 2015-11-25 埃克塞里艾克西斯公司 N-[3-氟-4-({6-(甲基氧基)-7-[(3-吗啉-4-基丙基)氧基]-喹啉-4-基}氧基)苯基]-n′-(4-氟苯基)环丙烷-1，1-二甲酰胺的晶形
UA108618C2 (uk) 2009-08-07 2015-05-25 Застосування c-met-модуляторів в комбінації з темозоломідом та/або променевою терапією для лікування раку
AU2011224203A1 (en) 2010-03-12 2012-10-04 Exelixis, Inc Hydrated crystalline forms of N-[3-fluoro-4-({6-(methyloxy)-7-[(3-morpholin -4-ylpropyl)oxy]-quinolin-4-yl}oxy)phenyl] -N'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide
US20120070368A1 (en) 2010-04-16 2012-03-22 Exelixis, Inc. Methods of Using C-Met Modulators
EA030435B1 (ru) 2010-07-16 2018-08-31 Экселиксис, Инк. ТАБЛЕТКА, СОДЕРЖАЩАЯ МОДУЛЯТОР c-MET В ФОРМЕ КРИСТАЛЛИЧЕСКОЙ L-МАЛАТНОЙ СОЛИ (ВАРИАНТЫ), СПОСОБ ЕЕ ПРОИЗВОДСТВА И СПОСОБ ЛЕЧЕНИЯ ОНКОЛОГИЧЕСКОГО ЗАБОЛЕВАНИЯ С ЕЕ ИСПОЛЬЗОВАНИЕМ
US20140186407A9 (en) 2010-07-16 2014-07-03 Exelixis Inc. C-Met Modulator Pharmaceutical Compositions
US20140057908A1 (en) 2010-09-27 2014-02-27 Exelixis, Inc. Method of Treating Cancer
JP2013540759A (ja) 2010-09-27 2013-11-07 エクセリクシス， インク． 去勢抵抗性前立腺癌および造骨性転移の治療のためのｍｅｔおよびｖｅｇｆの二元阻害薬
MX352926B (es) 2010-09-27 2017-12-14 Exelixis Inc Inhibidores dobles de met y factor de crecimiento endotelial vascular (vegf) para el tratamiento de cancer de prostata resistente a la castracion y metastasis osteoblasticas en los huesos.
WO2012071321A1 (en) 2010-11-22 2012-05-31 Glaxosmithkline Llc Method of treating cancer
SG191230A1 (en) 2010-12-23 2013-07-31 Nestec Sa Drug selection for malignant cancer therapy using antibody-based arrays
CN102093421B (zh) 2011-01-28 2014-07-02 北京康辰药业有限公司 一种含磷取代基的喹啉类化合物及其制备方法、以及含有该化合物的药物组合物及其应用
BR112013020362A2 (pt) 2011-02-10 2018-05-29 Exelixis Inc processos para a preparação de compostos de quinolina, compostos e combinações farmacêuticas que os contem
US20120252840A1 (en) 2011-04-04 2012-10-04 Exelixis, Inc. Method of Treating Cancer
MX2013012695A (es) 2011-05-02 2014-03-27 Exelixis Inc Metodo para el tratamiento del cancer y el dolor por cancer de hueso.
TW201306842A (zh) 2011-06-15 2013-02-16 Exelixis Inc 使用ｐｉ３ｋ／ｍｔｏｒ吡啶並嘧啶酮抑制劑及苯達莫司汀及／或利妥昔單抗治療惡性血液疾病之組合療法
EP2758057B1 (en) 2011-09-22 2017-05-31 Exelixis, Inc. Method for treating osteoporosis
CN104395284A (zh) 2011-10-20 2015-03-04 埃克塞里艾克西斯公司 制备喹啉衍生物的方法
IN2014CN04067A (https=) 2011-11-08 2015-10-23 Exelixis Inc
WO2013166296A1 (en) 2012-05-02 2013-11-07 Exelixis, Inc. A dual met - vegf modulator for treating osteolytic bone metastases
JP6513567B2 (ja) 2012-09-07 2019-05-15 エクセリクシス， インク． 肺腺癌の治療で使用するためのｍｅｔ、ｖｅｇｆｒ、およびｒｅｔの阻害剤
CN103664776B (zh) * 2012-09-26 2016-05-04 正大天晴药业集团股份有限公司 一种酪氨酸激酶抑制剂及其中间体的制备方法
US20140221372A1 (en) 2013-02-06 2014-08-07 GlaxoSmithKline Intellectual Property (NO 2.) Limited Method of administration and treatment
CA2907334C (en) 2013-03-15 2021-12-07 Exelixis, Inc. Metabolites of n-(4-{[6,7-bis(methyloxy)quinolin-4-yl]oxy}phenyl)-n'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide
WO2014145693A1 (en) * 2013-03-15 2014-09-18 Exelixis, Inc. Metabolites of n-[3-fluoro-4-({ 6-(methyloxy)-7-[(3-morpholin-4-ylpropyl)oxy]quinolin-4-yl}oxy)phenyl]-n'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide
WO2014165779A1 (en) 2013-04-04 2014-10-09 Exelixis, Inc. Drug combinations to treat cancer
US11564915B2 (en) 2013-04-04 2023-01-31 Exelixis, Inc. Cabozantinib dosage form and use in the treatment of cancer
BR112016018450A2 (pt) 2014-02-14 2018-09-18 Exelixis Inc formas sólidas cristalinas de n-{4-[(6,7-dimetoxiquinolin-4-il)oxi]fenil}-n'-(4-fluorofenil)ciclopropano-1,1-dicarboxamida, processos de preparo e métodos de uso
EP3119476A1 (en) * 2014-03-17 2017-01-25 Exelixis, Inc. Dosing of cabozantinib formulations
EP3174854B1 (en) * 2014-07-31 2022-08-24 Exelixis, Inc. Method of preparing fluorine-18 labeled cabozantinib and its analogs

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005030140A2 (en) * 2003-09-26 2005-04-07 Exelixis, Inc. C-met modulators and methods of use

Also Published As

Publication number Publication date
CA2907334A1 (en) 2014-09-18
WO2014145715A1 (en) 2014-09-18
EA201591756A1 (ru) 2016-02-29
NZ712330A (en) 2020-04-24
ES2729626T3 (es) 2019-11-05
MX2015012490A (es) 2016-05-24
US20160031818A1 (en) 2016-02-04
AU2014232714B2 (en) 2018-07-19
AU2014232714A1 (en) 2015-10-08
BR112015023109A2 (en) 2018-05-15
US20210002228A1 (en) 2021-01-07
ZA201506842B (en) 2017-08-30
AU2018204666A1 (en) 2018-07-19
MX366003B (es) 2019-06-24
CN105121412B (zh) 2019-07-12
US10273211B2 (en) 2019-04-30
GEP20196995B (en) 2019-07-25
US20240287002A1 (en) 2024-08-29
JP2016516074A (ja) 2016-06-02
EP2970126A1 (en) 2016-01-20
HK1220447A1 (en) 2017-05-05
UA119321C2 (uk) 2019-06-10
CA2907334C (en) 2021-12-07
CN105121412A (zh) 2015-12-02
IL241577B (en) 2019-11-28
EP2970126B1 (en) 2019-03-06
KR20150130376A (ko) 2015-11-23
JP6389238B2 (ja) 2018-09-12
EA033786B1 (ru) 2019-11-26
US20190218182A1 (en) 2019-07-18
GEAP201913960A (en) 2019-04-10

Similar Documents

Publication Publication Date Title
KR102276348B1 (ko) Ｎ­（４­〔［６,７­비스（메틸옥시）퀴놀린­４­일］옥시〕페닐）­ｎ′­（４­플루오로페닐）시클로프로판­１,１­디카복사미드의 대사물
JP6666849B2 (ja) カボザンチニブ製剤の投与
EP2252605B1 (en) Labelled analogues of halobenzamides as multimodal radiopharmaceuticals and their precursors
KR101761380B1 (ko) Ｃ－ｍｅｔ 조절제를 사용하는 방법
CN110573186A (zh) 发射α的放射性核素的大环配合物及其在癌症的靶向放射治疗中的应用
CN106674202A (zh) 化合物a的二甲磺酸盐及其晶型和含有该盐的药物组合物
WO2014145693A1 (en) Metabolites of n-[3-fluoro-4-({ 6-(methyloxy)-7-[(3-morpholin-4-ylpropyl)oxy]quinolin-4-yl}oxy)phenyl]-n'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide
WO2023208174A1 (zh) 去泛素化酶抑制剂及其应用
HK1220447B (en) Metabolites of n-(4-{[6,7-bis(methyloxy)quinolin-4-yl]oxy}phenyl)-n'-(4-fluorophenyl) cyclopropane-1,1-dicarboxamide
CN111362871B (zh) 取代的吡啶-2-甲酰胺类化合物及其用途
TWI419894B (zh) ４-苯胺基呋喃［２，３－ｂ］喹啉衍生物，其製備方法以及包含有此等衍生物的藥學組成物
CN119143669B (zh) 一种新型7-甲氧基-4-苯氧基喹啉-6-甲酰胺类化合物及其应用
CN117865880A (zh) 一种kx2-361-d4苯磺酸盐的合成工艺
CZ82099A3 (cs) Způsob zjištění čistoty a stálosti vzorku lanotriginu

Legal Events

Date Code Title Description
PA0105 International application

Patent event date: 20151006

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: 20190314

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: 20201023

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: 20210407

GRNT Written decision to grant
PR0701 Registration of establishment

Comment text: Registration of Establishment

Patent event date: 20210706

Patent event code: PR07011E01D

PR1002 Payment of registration fee

Payment date: 20210706

End annual number: 3

Start annual number: 1

PG1601 Publication of registration
PR1001 Payment of annual fee

Payment date: 20240617

Start annual number: 4

End annual number: 4

PR1001 Payment of annual fee

Payment date: 20250616

Start annual number: 5

End annual number: 5