KR102404629B1 - 할리콘드린 마크롤리드 및 그의 유사체의 합성에 유용한 프린스 반응 및 중간체 - Google Patents

할리콘드린 마크롤리드 및 그의 유사체의 합성에 유용한 프린스 반응 및 중간체 Download PDF

Info

Publication number
KR102404629B1
KR102404629B1 KR1020197002930A KR20197002930A KR102404629B1 KR 102404629 B1 KR102404629 B1 KR 102404629B1 KR 1020197002930 A KR1020197002930 A KR 1020197002930A KR 20197002930 A KR20197002930 A KR 20197002930A KR 102404629 B1 KR102404629 B1 KR 102404629B1
Authority
KR
South Korea
Prior art keywords
alkyl
aryl
optionally substituted
heteroaryl
protecting group
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
KR1020197002930A
Other languages
English (en)
Korean (ko)
Other versions
KR20190039103A (ko
Inventor
찰스 이. 체이스
형욱 최
아츠시 엔도
프란시스 쥐. 팡
대식 김
Original Assignee
에자이 알앤드디 매니지먼트 가부시키가이샤
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 에자이 알앤드디 매니지먼트 가부시키가이샤 filed Critical 에자이 알앤드디 매니지먼트 가부시키가이샤
Publication of KR20190039103A publication Critical patent/KR20190039103A/ko
Application granted granted Critical
Publication of KR102404629B1 publication Critical patent/KR102404629B1/ko
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D407/00Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/04Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/335Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
    • C07D307/20Oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/28Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D321/00Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D407/00Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/06Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D407/00Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/14Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D493/00Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D493/00Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/12Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D493/00Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/12Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
    • C07D493/16Peri-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D493/00Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/12Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
    • C07D493/18Bridged systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D493/00Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/22Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D519/00Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/18Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804Compounds having Si-O-C linkages
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6561Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/55Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
KR1020197002930A 2016-06-30 2017-06-30 할리콘드린 마크롤리드 및 그의 유사체의 합성에 유용한 프린스 반응 및 중간체 Active KR102404629B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201662357031P 2016-06-30 2016-06-30
US62/357,031 2016-06-30
PCT/US2017/040401 WO2018006031A1 (en) 2016-06-30 2017-06-30 Prins reaction and intermediates useful in the synthesis of halichondrin macrolides and analogs thereof

Publications (2)

Publication Number Publication Date
KR20190039103A KR20190039103A (ko) 2019-04-10
KR102404629B1 true KR102404629B1 (ko) 2022-06-02

Family

ID=60786711

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020197002930A Active KR102404629B1 (ko) 2016-06-30 2017-06-30 할리콘드린 마크롤리드 및 그의 유사체의 합성에 유용한 프린스 반응 및 중간체

Country Status (9)

Country Link
US (1) US11136335B2 (enExample)
EP (1) EP3478691A4 (enExample)
JP (3) JP7068204B2 (enExample)
KR (1) KR102404629B1 (enExample)
CN (2) CN114805322B (enExample)
IL (2) IL263845B (enExample)
MX (1) MX390072B (enExample)
SG (1) SG11201811671XA (enExample)
WO (1) WO2018006031A1 (enExample)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL2522663T3 (pl) 2004-06-03 2015-08-31 Eisai R&D Man Co Ltd Produkty pośrednie do otrzymywania halichondryny B
CN108948039B (zh) 2007-10-03 2021-12-31 卫材R&D管理有限公司 用于合成软海绵素b类似物的中间体和方法
CN102803254B (zh) 2010-01-26 2016-09-14 卫材R&D管理有限公司 用于软海绵素b类似物合成的呋喃并[3,2-b]吡喃衍生物
CN105683198B (zh) 2013-11-04 2019-03-12 卫材R&D管理有限公司 软海绵素b的类似物合成中有用的大环化反应和中间体
HUE043088T2 (hu) 2013-12-06 2019-08-28 Eisai R&D Man Co Ltd Halikondrin B analógok szintézisében alkalmazható eljárások
RU2020141025A (ru) 2015-05-07 2020-12-28 Эйсай Ар Энд Ди Менеджмент Ко., Лтд. Реакции макроциклизации и промежуточные соединения и другие фрагменты, полезные в синтезе макролидов галихондринов
US10676481B2 (en) 2016-02-12 2020-06-09 Eisai R&D Management Co., Ltd. Intermediates in the synthesis of eribulin and related methods of synthesis
KR20250057138A (ko) 2018-01-03 2025-04-28 에자이 알앤드디 매니지먼트 가부시키가이샤 할리콘드린 마크롤리드 및 그의 유사체의 합성에 유용한 프린스 반응 및 화합물
US11396515B2 (en) 2018-03-02 2022-07-26 Beijing Tienyi Lufu Pharmatech Co. Ltd. Pyran fused ring compound, preparation method therefor and use thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015066729A1 (en) * 2013-11-04 2015-05-07 Eisai R&D Management Co., Ltd. Macrocyclization reactions and intermediates useful in the synthesis of analogs of halichondrin b

Family Cites Families (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU652180A1 (ru) 1975-12-16 1979-03-15 Краснодарский политехнический институт 1(Фурил-2,)-2-(2-,, формилфурил-5,, ) этилен или его метильное производное как промежуточный продукт дл синтеза фуран-2,5-дикарбоновой кислоты и способ его получени
US5436238A (en) 1992-03-12 1995-07-25 President And Fellows Of Harvard College Halichondrins and related compounds
US5338865A (en) 1992-03-12 1994-08-16 President And Fellows Of Harvard College Synthesis of halichondrin B and norhalichondrin B
GB9206244D0 (en) 1992-03-23 1992-05-06 Pharma Mar Sa Cytotoxic compound from a marine sponge
TW255880B (enExample) 1992-09-09 1995-09-01 Hoechst Ag
US6194586B1 (en) 1996-09-06 2001-02-27 Eli Lilly And Company Selective sulphonation of the primary alcohol of a diol containing both primary and secondary alcohols
US6870058B2 (en) 1996-12-03 2005-03-22 The Trustees Of The University Of Pennsylvania Compounds which mimic the chemical and biological properties of discodermolide
US6653341B1 (en) 1998-06-17 2003-11-25 Eisai Co., Ltd. Methods and compositions for use in treating cancer
HU227912B1 (en) 1998-06-17 2012-05-29 Eisai R & D Man Co Halichondrin analogs and methods of their use and preparation
US8097648B2 (en) 1998-06-17 2012-01-17 Eisai R&D Management Co., Ltd. Methods and compositions for use in treating cancer
DE10106647A1 (de) 2001-02-12 2002-08-22 Univ Hannover Ratjadon-Derivate zum Hemmen des Zellwachstums
PL2522663T3 (pl) 2004-06-03 2015-08-31 Eisai R&D Man Co Ltd Produkty pośrednie do otrzymywania halichondryny B
US20060045846A1 (en) 2004-08-30 2006-03-02 Horstmann Thomas E Reagents and methods for labeling terminal olefins
EP1831697A4 (en) 2004-12-09 2011-01-26 Eisai R&D Man Co Ltd SEARCH FOR TUBULINISOTYPES IN CANCER THERAPY USING HALICHONDRIN B ANALOG
JP2009510005A (ja) 2005-09-26 2009-03-12 シムライズ・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング・ウント・コンパニー・コマンジツト・ゲゼルシヤフト 分子内プリンス反応および該反応に適する触媒
WO2008010776A1 (en) 2006-07-21 2008-01-24 Agency For Science, Technology And Research Aigialomycin d and derivatives thereof and their use in treating cancer or malaria or a microbial infection
US8119839B2 (en) 2007-07-20 2012-02-21 Yamada Apiculture Center, Inc. Carboxylic acid and antidepressant composition containing the same as active ingredient
CN108948039B (zh) 2007-10-03 2021-12-31 卫材R&D管理有限公司 用于合成软海绵素b类似物的中间体和方法
US20090203771A1 (en) 2007-11-16 2009-08-13 Eisai R&D Management Co., Ltd. Novel intermediate for halichondrin b analog synthesis and novel desulfonylation reaction used for the intermediate
CN105801599A (zh) 2008-04-04 2016-07-27 卫材R&D管理有限公司 软海绵素b类似物
JP5371091B2 (ja) 2009-01-23 2013-12-18 三菱レイヨン株式会社 モノスルホン酸エステルの製造方法
CN102803254B (zh) 2010-01-26 2016-09-14 卫材R&D管理有限公司 用于软海绵素b类似物合成的呋喃并[3,2-b]吡喃衍生物
WO2012147900A1 (en) 2011-04-28 2012-11-01 Eisai R&D Management Co., Ltd. Microreactor process for halichondrin b analog synthesis
CA2857385A1 (en) 2011-11-30 2013-06-06 Alphora Research Inc. Process for preparation of (3r)-2,4-di-leaving group-3-methylbut-1-ene
US9278979B2 (en) 2012-03-30 2016-03-08 Alphora Research Inc. Synthetic process for preparation of macrocyclic C1-keto analogs of halichondrin B and intermediates useful therein
US9850254B2 (en) 2013-07-03 2017-12-26 Sandoz Ag Synthetic process for preparation of macrocyclic C1-keto analogs of Halichondrin B and intermediates useful therein including intermediates containing-SO2-(p-tolyl) groups
HUE043088T2 (hu) 2013-12-06 2019-08-28 Eisai R&D Man Co Ltd Halikondrin B analógok szintézisében alkalmazható eljárások
EP3191479B1 (en) 2014-09-09 2020-04-08 Cipla Limited "process for the preparation of macrocyclic ketone analogs of halichondrin b or pharmaceutically acceptable salts and intermediates thereof"
RU2020141025A (ru) 2015-05-07 2020-12-28 Эйсай Ар Энд Ди Менеджмент Ко., Лтд. Реакции макроциклизации и промежуточные соединения и другие фрагменты, полезные в синтезе макролидов галихондринов
US10676481B2 (en) 2016-02-12 2020-06-09 Eisai R&D Management Co., Ltd. Intermediates in the synthesis of eribulin and related methods of synthesis
WO2018217894A1 (en) 2017-05-24 2018-11-29 Eisai R&D Management Co., Ltd. Fluorine-labelled halichondrin derivatives and related methods of synthesis
KR20250057138A (ko) 2018-01-03 2025-04-28 에자이 알앤드디 매니지먼트 가부시키가이샤 할리콘드린 마크롤리드 및 그의 유사체의 합성에 유용한 프린스 반응 및 화합물

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015066729A1 (en) * 2013-11-04 2015-05-07 Eisai R&D Management Co., Ltd. Macrocyclization reactions and intermediates useful in the synthesis of analogs of halichondrin b

Also Published As

Publication number Publication date
RU2019102375A (ru) 2020-07-30
JP2019524674A (ja) 2019-09-05
MX390072B (es) 2025-03-20
JP7068204B2 (ja) 2022-05-16
EP3478691A4 (en) 2020-07-22
US11136335B2 (en) 2021-10-05
JP2024056892A (ja) 2024-04-23
IL288460B1 (en) 2023-04-01
CN109641917A (zh) 2019-04-16
CN114805322A (zh) 2022-07-29
MX2018016329A (es) 2019-09-18
WO2018006031A1 (en) 2018-01-04
IL263845B (en) 2022-01-01
IL288460A (en) 2022-01-01
IL288460B2 (en) 2023-08-01
CN109641917B (zh) 2022-06-14
EP3478691A1 (en) 2019-05-08
CN114805322B (zh) 2025-05-30
RU2019102375A3 (enExample) 2021-07-05
SG11201811671XA (en) 2019-01-30
JP2022105115A (ja) 2022-07-12
US20190161495A1 (en) 2019-05-30
IL263845A (en) 2019-01-31
KR20190039103A (ko) 2019-04-10
JP7440563B2 (ja) 2024-02-28

Similar Documents

Publication Publication Date Title
US11643418B2 (en) Macrocyclization reactions and intermediates and other fragments useful in the synthesis of analogs of halichondrin B
JP7440563B2 (ja) ハリコンドリンマクロライドおよびその類縁体の合成に有用なプリンス反応および中間体
KR102743950B1 (ko) 할리콘드린 마크롤라이드의 합성에 유용한 마크로고리화 반응 및 중간체 및 기타 단편
RU2777913C2 (ru) Реакция принса и промежуточные продукты, применимые при синтезе макролидов галихондринового ряда и их аналогов

Legal Events

Date Code Title Description
PA0105 International application

Patent event date: 20190129

Patent event code: PA01051R01D

Comment text: International Patent Application

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

Patent event code: PA02012R01D

Patent event date: 20200629

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: 20210813

Patent event code: PE09021S01D

AMND Amendment
E601 Decision to refuse application
PE0601 Decision on rejection of patent

Patent event date: 20220218

Comment text: Decision to Refuse Application

Patent event code: PE06012S01D

Patent event date: 20210813

Comment text: Notification of reason for refusal

Patent event code: PE06011S01I

X091 Application refused [patent]
AMND Amendment
PX0901 Re-examination

Patent event code: PX09011S01I

Patent event date: 20220218

Comment text: Decision to Refuse Application

Patent event code: PX09012R01I

Patent event date: 20211013

Comment text: Amendment to Specification, etc.

Patent event code: PX09012R01I

Patent event date: 20200629

Comment text: Amendment to Specification, etc.

PX0701 Decision of registration after re-examination

Patent event date: 20220408

Comment text: Decision to Grant Registration

Patent event code: PX07013S01D

Patent event date: 20220323

Comment text: Amendment to Specification, etc.

Patent event code: PX07012R01I

Patent event date: 20220218

Comment text: Decision to Refuse Application

Patent event code: PX07011S01I

Patent event date: 20211013

Comment text: Amendment to Specification, etc.

Patent event code: PX07012R01I

Patent event date: 20200629

Comment text: Amendment to Specification, etc.

Patent event code: PX07012R01I

X701 Decision to grant (after re-examination)
GRNT Written decision to grant
PR0701 Registration of establishment

Comment text: Registration of Establishment

Patent event date: 20220527

Patent event code: PR07011E01D

PR1002 Payment of registration fee

Payment date: 20220530

End annual number: 3

Start annual number: 1

PG1601 Publication of registration