KR101862891B1 - C-아릴 글루코시드 유도체, 그 제조 방법 및 약제학적 용도 - Google Patents

C-아릴 글루코시드 유도체, 그 제조 방법 및 약제학적 용도 Download PDF

Info

Publication number
KR101862891B1
KR101862891B1 KR1020137005058A KR20137005058A KR101862891B1 KR 101862891 B1 KR101862891 B1 KR 101862891B1 KR 1020137005058 A KR1020137005058 A KR 1020137005058A KR 20137005058 A KR20137005058 A KR 20137005058A KR 101862891 B1 KR101862891 B1 KR 101862891B1
Authority
KR
South Korea
Prior art keywords
phenyl
mmol
methoxy
methyl
reaction mixture
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
KR1020137005058A
Other languages
English (en)
Korean (ko)
Other versions
KR20130095741A (ko
Inventor
팡롱 양
펭 초 탕
큉 동
왕양 투
지앙 판
동리앙 구안
구앙유안 셴
양 왕
지준 유안
리민 장
Original Assignee
샹하이 헨그루이 파마수티컬 컴퍼니 리미티드
지앙수 헨그루이 메디슨 컴퍼니 리미티드
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 샹하이 헨그루이 파마수티컬 컴퍼니 리미티드, 지앙수 헨그루이 메디슨 컴퍼니 리미티드 filed Critical 샹하이 헨그루이 파마수티컬 컴퍼니 리미티드
Publication of KR20130095741A publication Critical patent/KR20130095741A/ko
Application granted granted Critical
Publication of KR101862891B1 publication Critical patent/KR101862891B1/ko
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/08—Bridged systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • 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
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • 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
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
    • A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
    • 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
    • A61P9/10—Drugs 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
    • 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
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/18—Acyclic radicals, substituted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
    • C07H7/04—Carbocyclic radicals
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Diabetes (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Urology & Nephrology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Endocrinology (AREA)
  • Cardiology (AREA)
  • Vascular Medicine (AREA)
  • Ophthalmology & Optometry (AREA)
  • Child & Adolescent Psychology (AREA)
  • Emergency Medicine (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
KR1020137005058A 2010-08-10 2011-06-30 C-아릴 글루코시드 유도체, 그 제조 방법 및 약제학적 용도 Expired - Fee Related KR101862891B1 (ko)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
CN201010249618 2010-08-10
CN201010249618.3 2010-08-10
CN201010589606.5 2010-12-06
CN2010105896065A CN102372722A (zh) 2010-08-10 2010-12-06 C-芳基葡萄糖苷衍生物、其制备方法及其在医药上的应用
PCT/CN2011/076680 WO2012019496A1 (zh) 2010-08-10 2011-06-30 C-芳基葡萄糖苷衍生物、其制备方法及其在医药上的应用

Publications (2)

Publication Number Publication Date
KR20130095741A KR20130095741A (ko) 2013-08-28
KR101862891B1 true KR101862891B1 (ko) 2018-05-30

Family

ID=45567352

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020137005058A Expired - Fee Related KR101862891B1 (ko) 2010-08-10 2011-06-30 C-아릴 글루코시드 유도체, 그 제조 방법 및 약제학적 용도

Country Status (11)

Country Link
US (1) US8609622B2 (https=)
EP (1) EP2604612B1 (https=)
JP (1) JP5984808B2 (https=)
KR (1) KR101862891B1 (https=)
CN (2) CN102372722A (https=)
BR (1) BR112013002125A2 (https=)
CA (1) CA2807034C (https=)
ES (1) ES2581728T3 (https=)
MX (1) MX2013001098A (https=)
RU (1) RU2606501C2 (https=)
WO (1) WO2012019496A1 (https=)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101609859B1 (ko) * 2011-04-25 2016-04-07 베이징 프릴루드 팜. 에스씨아이. & 테크. 씨오., 엘티디. 소듐-의존적 포도당 운반 단백질의 억제제 및 이의 제조방법 및 용도
US9018249B2 (en) 2011-09-13 2015-04-28 Panacea Biotec Limited SGLT inhibitors
CN102627535A (zh) * 2012-03-31 2012-08-08 天津药物研究院 含1,1-二苯基环丙基结构的化合物的制备方法
WO2013178064A1 (zh) * 2012-05-29 2013-12-05 广东东阳光药业有限公司 吡喃葡萄糖基衍生物、其制备方法及其在医药上的应用
EP2968375B1 (en) 2013-03-14 2019-06-12 MSD International GmbH Methods for preparing sglt2 inhibitors
CN104151306A (zh) * 2013-05-13 2014-11-19 北京新天宇科技开发有限公司 一种坎格列净的新的制备方法
CN104619713B (zh) * 2013-05-24 2017-06-16 四川海思科制药有限公司 氧杂双环衍生物、制备方法及其应用
WO2014206349A1 (zh) * 2013-06-28 2014-12-31 四川海思科制药有限公司 氧杂-硫杂-双环[3.2.1]辛烷衍生物、制备方法及其用途
CN107311992B (zh) * 2013-09-09 2020-08-18 上海研健新药研发有限公司 C-芳基葡糖苷衍生物、其制备方法及其在医药上的应用
CN104447893B (zh) * 2013-09-25 2018-01-23 广东东阳光药业有限公司 吡喃葡萄糖基衍生物及其在医药上的应用
WO2015043511A1 (en) * 2013-09-27 2015-04-02 Sunshine Lake Pharma Co., Ltd. Glucopyranosyl derivatives and their uses in medicine
EP3089969A2 (en) * 2014-01-03 2016-11-09 Elexopharm GmbH Inhibitors of 17beta-hydroxysteroid dehydrogenases type 1 and type 2
KR102149572B1 (ko) 2014-05-19 2020-08-28 화이자 인코포레이티드 아시알로당단백질 수용체의 표적화제로서 치환된-6,8-다이옥사바이사이클로[3.2.1]옥탄-2,3-다이올 화합물
CN104017031A (zh) * 2014-06-21 2014-09-03 李友香 降血糖药物和组合物
CN104031098A (zh) * 2014-06-21 2014-09-10 李友香 降糖药物
CN105294785A (zh) * 2014-07-02 2016-02-03 上海阳帆医药科技有限公司 C-苯并五元杂芳环类芳基葡萄糖苷衍生物及其制备方法与用途
US20160002275A1 (en) * 2014-07-03 2016-01-07 Cadila Healthcare Limited Process for preparation and purification of canagliflozin
CN104119324B (zh) * 2014-07-23 2016-03-30 齐鲁天和惠世制药有限公司 一种卡格列净的制备方法
CN105461762B (zh) * 2014-09-27 2018-12-04 广东东阳光药业有限公司 吡喃葡萄糖基衍生物及其在医药上的应用
KR20170060035A (ko) * 2014-09-30 2017-05-31 지앙수 헨그루이 메디슨 컴퍼니 리미티드 나트륨 글루코스 공동운반체 2 억제제의 ｌ- 프롤린 화합물, 및 ｌ- 프롤린 화합물의 모노하이드레이트 및 결정
US20170342100A1 (en) * 2014-12-03 2017-11-30 Sun Pharmaceutical Industries Limited Processes for the preparation of ertugliflozin
WO2016189463A1 (en) * 2015-05-25 2016-12-01 Sun Pharmaceutical Industries Limited Ertugliflozin co-crystals and process for their preparation
DK3404033T3 (da) 2016-01-04 2020-11-02 Jeil Pharmaceutical Co Ltd C-glukosidderivat med kondenseret phenylring eller farmaceutisk acceptabelt salt deraf, fremgangsmåde til fremstilling deraf og farmaceutisk sammensætning indeholdende dette
CN106955273B (zh) * 2016-01-11 2020-10-20 江苏恒瑞医药股份有限公司 一种含有钠-葡萄糖协同转运蛋白2抑制剂的药物组合物
CN107686496B (zh) * 2016-08-05 2021-01-19 江苏恒瑞医药股份有限公司 一种钠-葡萄糖协同转运蛋白2抑制剂的制备方法
CN106674245B (zh) * 2017-01-10 2019-07-26 北京中海康医药科技发展有限公司 吡喃葡萄糖基衍生物的制备及医药上的应用
CN109549939A (zh) * 2017-09-26 2019-04-02 江苏恒瑞医药股份有限公司 Sglt2抑制剂和dpp-4抑制剂联合在制备治疗糖尿病的药物中的用途
CN109806397A (zh) * 2017-11-20 2019-05-28 江苏恒瑞医药股份有限公司 Sglt2抑制剂与arb联合在制备治疗高血压等疾病的药物中的用途
WO2020039394A1 (en) 2018-08-24 2020-02-27 Novartis Ag New drug combinations
CN113004349A (zh) * 2019-12-19 2021-06-22 上海研健新药研发有限公司 一种SGLTs抑制剂的制备方法及其关键中间体
WO2021121270A1 (zh) * 2019-12-19 2021-06-24 上海研健新药研发有限公司 一种SGLTs抑制剂的纯化方法及其应用
EP4114365A1 (en) 2020-03-05 2023-01-11 KRKA, d.d., Novo mesto Pharmaceutical composition comprising sglt2 inhibitor
EP4161912A1 (en) 2020-06-05 2023-04-12 KRKA, d.d., Novo mesto Preparation of highly pure amorphous dapagliflozin
CN114195748B (zh) * 2020-09-17 2023-11-14 上海森辉医药有限公司 一种钠-葡萄糖协同转运蛋白2抑制剂的制备方法
CN112375087A (zh) * 2020-11-27 2021-02-19 浙江天宇药业股份有限公司 一种脯氨酸恒格列净的合成方法
CN113880701A (zh) * 2021-10-10 2022-01-04 浙江司太立制药股份有限公司 一种抗糖尿病药物中间体及其制备方法
CN116785268A (zh) * 2022-03-14 2023-09-22 江苏万邦生化医药集团有限责任公司 一种sglt-2抑制剂的药物组合物

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010023594A1 (en) * 2008-08-28 2010-03-04 Pfizer Inc. Dioxa-bicyclo[3.2.1.]octane-2,3,4-triol derivatives

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1020944C (zh) 1990-01-30 1993-05-26 阿图尔-费希尔股份公司费希尔厂 紧固件
WO2002083066A2 (en) * 2001-04-11 2002-10-24 Bristol-Myers Squibb Company Amino acid complexes of c-aryl glucosides for treatment of diabetes and method
TWI254635B (en) 2002-08-05 2006-05-11 Yamanouchi Pharma Co Ltd Azulene derivative and salt thereof
ES2567571T3 (es) * 2003-03-14 2016-04-25 Astellas Pharma Inc. Derivados de C-glucósido y sales de los mismos
LT2896397T (lt) * 2003-08-01 2017-11-27 Mitsubishi Tanabe Pharma Corporation Nauji junginiai, turintys inhibitorinį aktyvumą prieš nuo natrio priklausomą gliukozės transporterį
CA2664095A1 (en) * 2006-09-21 2008-03-27 Boehringer Ingelheim International Gmbh Glucopyranosyl-substituted difluorobenzyl-benzene derivatives, medicaments containing such compounds, their use and process for their manufacture
MX2010002027A (es) 2007-08-23 2010-03-15 Theracos Inc Derivados de bencilbenceno y metodos de uso.
AU2009270936B2 (en) * 2008-07-15 2014-12-18 Theracos, Inc. Deuterated benzylbenzene derivatives and methods of use
MX2011001855A (es) 2008-08-22 2011-03-24 Theracos Inc Procesos para la preparacion de inhibidores de sglt2.
US20100167988A1 (en) 2008-10-22 2010-07-01 Auspex Pharmaceuticals, Inc. Ethoxyphenylmethyl inhibitors of sglt2
WO2010074219A1 (ja) * 2008-12-26 2010-07-01 アステラス製薬株式会社 ベンゾチオフェン化合物
EA021983B1 (ru) * 2009-11-02 2015-10-30 Пфайзер Инк. Производные диоксабицикло[3.2.1]октан-2,3,4-триола
WO2012172566A2 (en) * 2011-06-13 2012-12-20 Panacea Biotec Ltd. Novel sglt inhibitors

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010023594A1 (en) * 2008-08-28 2010-03-04 Pfizer Inc. Dioxa-bicyclo[3.2.1.]octane-2,3,4-triol derivatives

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Organic Letters 12(13):2940-2943(2010.06.08.)

Also Published As

Publication number Publication date
EP2604612B1 (en) 2016-04-20
US20130130997A1 (en) 2013-05-23
HK1167395A1 (en) 2012-11-30
WO2012019496A1 (zh) 2012-02-16
CN102482290A (zh) 2012-05-30
US8609622B2 (en) 2013-12-17
ES2581728T3 (es) 2016-09-07
CA2807034A1 (en) 2012-02-16
KR20130095741A (ko) 2013-08-28
CN102482290B (zh) 2014-01-15
EP2604612A1 (en) 2013-06-19
CN102372722A (zh) 2012-03-14
BR112013002125A2 (pt) 2016-05-24
RU2606501C2 (ru) 2017-01-10
JP5984808B2 (ja) 2016-09-06
MX2013001098A (es) 2013-06-05
JP2013533291A (ja) 2013-08-22
EP2604612A4 (en) 2013-07-24
RU2013107748A (ru) 2014-09-20
CA2807034C (en) 2019-05-07

Similar Documents

Publication Publication Date Title
KR101862891B1 (ko) C-아릴 글루코시드 유도체, 그 제조 방법 및 약제학적 용도
AU2014317663B2 (en) C-aryl glucoside derivative, preparation method for same, and medical applications thereof
KR101719758B1 (ko) 씨 글루코사이드 유도체
EP2968258B1 (en) Dual sglt1/sglt2 inhibitors
JP6667008B2 (ja) 融合フェニル環が含まれたｃ−グルコシド誘導体またはその薬学的に許容可能な塩、その製造方法、およびそれを含む薬学的組成物
WO2019215633A1 (en) 5,5-difluoro- and 5-fluoro-5-methyl-c-glycoside derivatives useful as dual sglt1 / sglt2 modulators
TWI510491B (zh) Ｃ－芳基葡萄糖苷衍生物、其製備方法及其在醫藥上的應用
HK1227881B (en) C-aryl glucoside derivative, preparation method for same, and medical applications thereof
HK1227881A1 (en) C-aryl glucoside derivative, preparation method for same, and medical applications thereof
US20200291004A1 (en) 5-fluoro-c-(aryl or heterocyclyl)-glycoside derivatives useful as dual sglt1 / sglt2 modulators
HK1167395B (en) C-aryl glucoside derivatives, preparation process and pharmaceutical use thereof
HK1259905B (zh) 具有稠合苯环的c-葡糖苷衍生物或其药物学可接受的盐、其制备方法以及包含其的药物组合物
HK1259905A1 (en) C-glycoside derivatives having fused phenyl ring or pharmaceutically acceptable salts thereof, method for preparing the same and pharmaceutical composition comprising the same

Legal Events

Date Code Title Description
PA0105 International application

St.27 status event code: A-0-1-A10-A15-nap-PA0105

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

PG1501 Laying open of application

St.27 status event code: A-1-1-Q10-Q12-nap-PG1501

PE0801 Dismissal of amendment

St.27 status event code: A-2-2-P10-P12-nap-PE0801

A201 Request for examination
P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

PA0201 Request for examination

St.27 status event code: A-1-2-D10-D11-exm-PA0201

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

St.27 status event code: A-1-2-D10-D21-exm-PE0902

T11-X000 Administrative time limit extension requested

St.27 status event code: U-3-3-T10-T11-oth-X000

E13-X000 Pre-grant limitation requested

St.27 status event code: A-2-3-E10-E13-lim-X000

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

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

St.27 status event code: A-1-2-D10-D22-exm-PE0701

GRNT Written decision to grant
PR0701 Registration of establishment

St.27 status event code: A-2-4-F10-F11-exm-PR0701

PR1002 Payment of registration fee

St.27 status event code: A-2-2-U10-U12-oth-PR1002

Fee payment year number: 1

PG1601 Publication of registration

St.27 status event code: A-4-4-Q10-Q13-nap-PG1601

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 4

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 5

PN2301 Change of applicant

St.27 status event code: A-5-5-R10-R13-asn-PN2301

St.27 status event code: A-5-5-R10-R11-asn-PN2301

PC1903 Unpaid annual fee

St.27 status event code: A-4-4-U10-U13-oth-PC1903

Not in force date: 20230525

Payment event data comment text: Termination Category : DEFAULT_OF_REGISTRATION_FEE

PC1903 Unpaid annual fee

St.27 status event code: N-4-6-H10-H13-oth-PC1903

Ip right cessation event data comment text: Termination Category : DEFAULT_OF_REGISTRATION_FEE

Not in force date: 20230525