JP6606508B2 - 抗真菌化合物の調製方法 - Google Patents

抗真菌化合物の調製方法 Download PDF

Info

Publication number
JP6606508B2
JP6606508B2 JP2016557965A JP2016557965A JP6606508B2 JP 6606508 B2 JP6606508 B2 JP 6606508B2 JP 2016557965 A JP2016557965 A JP 2016557965A JP 2016557965 A JP2016557965 A JP 2016557965A JP 6606508 B2 JP6606508 B2 JP 6606508B2
Authority
JP
Japan
Prior art keywords
aryl
alkyl
substituted
mixture
obtaining
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
JP2016557965A
Other languages
English (en)
Japanese (ja)
Other versions
JP2017507993A (ja
Inventor
フックストラ，ウィリアム，ジェー．
イェーツ，クリストファー，エム．
ベンケ，マーク
アリマーダノフ，アサフ
デイビッド，スコット，エー．
フライ，ダグラス，フランクリン
Original Assignee
マイコヴィア ファーマシューティカルズ，インコーポレイテッド
ザ ユナイテッド ステイツ オブ アメリカ， アズ リプレゼンテッド バイ ザ セクレタリー， デパートメント オブ ヘルス アンド ヒューマン サービシーズ
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 マイコヴィア ファーマシューティカルズ，インコーポレイテッド, ザ ユナイテッド ステイツ オブ アメリカ， アズ リプレゼンテッド バイ ザ セクレタリー， デパートメント オブ ヘルス アンド ヒューマン サービシーズ filed Critical マイコヴィア ファーマシューティカルズ，インコーポレイテッド
Publication of JP2017507993A publication Critical patent/JP2017507993A/ja
Application granted granted Critical
Publication of JP6606508B2 publication Critical patent/JP6606508B2/ja
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic 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
    • C07D401/02—Heterocyclic 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
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/56—Amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic 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
    • C07D405/02—Heterocyclic 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
    • C07D405/06—Heterocyclic 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 carbon chain containing only aliphatic carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Artificial Filaments (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
JP2016557965A 2014-03-19 2015-03-19 抗真菌化合物の調製方法 Expired - Fee Related JP6606508B2 (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201461955532P 2014-03-19 2014-03-19
US61/955,532 2014-03-19
PCT/US2015/021464 WO2015143154A1 (en) 2014-03-19 2015-03-19 Antifungal compound process

Publications (2)

Publication Number Publication Date
JP2017507993A JP2017507993A (ja) 2017-03-23
JP6606508B2 true JP6606508B2 (ja) 2019-11-13

Family

ID=54145313

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2016557965A Expired - Fee Related JP6606508B2 (ja) 2014-03-19 2015-03-19 抗真菌化合物の調製方法

Country Status (12)

Country Link
US (2) US10077250B2 (US07223432-20070529-C00017.png)
EP (1) EP3119771B1 (US07223432-20070529-C00017.png)
JP (1) JP6606508B2 (US07223432-20070529-C00017.png)
KR (1) KR20160138013A (US07223432-20070529-C00017.png)
CN (1) CN106459022B (US07223432-20070529-C00017.png)
AU (1) AU2015231208B2 (US07223432-20070529-C00017.png)
BR (1) BR112016021282A8 (US07223432-20070529-C00017.png)
CA (1) CA2942930A1 (US07223432-20070529-C00017.png)
EA (1) EA201691648A1 (US07223432-20070529-C00017.png)
ES (1) ES2800905T3 (US07223432-20070529-C00017.png)
MX (1) MX369357B (US07223432-20070529-C00017.png)
WO (1) WO2015143154A1 (US07223432-20070529-C00017.png)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015143172A1 (en) 2014-03-19 2015-09-24 Viamet Pharmaceuticals, Inc. Antifungal compound process
AU2015231208B2 (en) 2014-03-19 2019-04-04 Mycovia Pharmaceuticals, Inc. Antifungal compound process
EP3119754A4 (en) 2014-03-19 2017-12-13 Viamet Pharmaceuticals, Inc. Antifungal compound process
JP2017507991A (ja) 2014-03-19 2017-03-23 ヴィアメット ファーマスーティカルズ，インコーポレイテッド 抗真菌化合物の調製方法
JP6613391B2 (ja) 2014-03-19 2019-12-04 ブイピーエス‐３，インコーポレイテッド ２−（２，４−ジフルオロフェニル）−１，１−ジフルオロ−１−（５−置換ピリジン−２−イル）−３−（１ｈ−テトラゾール−１−イル）プロパン−２−オールおよびその調製工程
EP3119756B9 (en) 2014-03-19 2021-08-25 Dow AgroSciences LLC 2-(2,4-difluorophenyl)-1,1-difluoro-1-(5-substituted-pyridin-2-yl)-3-(1h-tetrazol-1-yl)propan-2-ols and processes for their preparation
EP3119764B1 (en) * 2014-03-19 2019-04-17 Viamet Pharmaceuticals (NC), Inc. Antifungal compound process
US10000465B2 (en) 2014-03-19 2018-06-19 Mycovia Pharmaceuticals, Inc. Antifungal compound process
WO2015143184A1 (en) 2014-03-19 2015-09-24 Viamet Pharmaceuticals, Inc. Antifungal compound process
EA036098B1 (ru) * 2015-09-18 2020-09-28 ВиПиЭс-3, ИНК. Способ получения противогрибковых соединений
BR112020009446A2 (pt) 2017-11-13 2020-11-03 Bayer Aktiengesellschaft derivados de tetrazólio propila e seu uso como fungicida
CN114573557B (zh) * 2022-03-28 2024-03-08 浙江天宇药业股份有限公司 一种奥特康唑的制备方法

Family Cites Families (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2854015B2 (de) 1978-12-14 1980-10-09 Dynamit Nobel Ag, 5210 Troisdorf Verfahren zur Herstellung von !H-TetrazoI-1-essigsauren und bestimmter Ester derselben
JP2000344744A (ja) 1999-06-04 2000-12-12 Ss Pharmaceut Co Ltd アセトフェノン誘導体およびその製法
US8198448B2 (en) 2006-07-14 2012-06-12 Amgen Inc. Fused heterocyclic derivatives and methods of use
KR100889937B1 (ko) 2007-08-06 2009-03-20 한미약품 주식회사 보리코나졸의 제조방법
KR101109215B1 (ko) 2009-06-17 2012-01-30 보령제약 주식회사 보리코나졸의 신규 중간체 및 이를 이용한 보리코나졸의 제조방법
US20120088664A1 (en) 2009-06-18 2012-04-12 Basf Se Antifungal 1,2,4-triazolyl derivatives having a 5-sulfur subtituent
EP2563771B1 (en) * 2010-04-24 2015-11-25 Viamet Pharmaceuticals, Inc. Metalloenzyme inhibitor compounds
EP3067350B1 (en) 2011-06-19 2018-06-13 Viamet Pharmaceuticals (NC), Inc. Metalloenzyme inhibitor compounds
JP6122846B2 (ja) 2011-06-19 2017-04-26 ヴィアメット ファーマスーティカルズ，インコーポレイテッド 金属酵素阻害剤化合物
EA201490052A1 (ru) 2011-06-23 2014-04-30 Вайамет Фармасьютикалс, Инк. Соединения, ингибирующие металлоферменты
CA2858681C (en) 2011-12-11 2021-07-06 Viamet Pharmaceuticals, Inc. Metalloenzyme inhibitor compounds
EA026209B1 (ru) 2012-01-20 2017-03-31 Ваймет Фармасьютикалс, Инк. Соединения, ингибирующие металлоферменты
CA2861341A1 (en) * 2012-01-20 2013-07-25 Viamet Pharmaceuticals, Inc. Metalloenzyme inhibitor compounds against fungal infection induced plant diseases and method of use thereof
US20150246898A1 (en) 2012-09-12 2015-09-03 Dow Agrosciences Llc Metalloenzyme inhibitor compounds
EP2948450A4 (en) 2013-01-28 2016-11-09 Viamet Pharmaceuticals Inc METALLOENZYMINHIBITORVERBINDUNGEN
WO2014165861A1 (en) 2013-04-05 2014-10-09 The Regents Of The University Of California Metal-catalyzed coupling of aryl and vinyl halides with alpha, alpha-difluorocarbonyl compounds
CA2913914C (en) * 2013-05-28 2018-03-20 Viamet Pharmaceuticals, Inc. Fungicidal compositions
EP3008051A4 (en) 2013-06-12 2017-03-01 Viamet Pharmaceuticals, Inc. Metalloenzyme inhibitor compounds
JP6613391B2 (ja) 2014-03-19 2019-12-04 ブイピーエス‐３，インコーポレイテッド ２−（２，４−ジフルオロフェニル）−１，１−ジフルオロ−１−（５−置換ピリジン−２−イル）−３−（１ｈ−テトラゾール−１−イル）プロパン−２−オールおよびその調製工程
AU2015231208B2 (en) 2014-03-19 2019-04-04 Mycovia Pharmaceuticals, Inc. Antifungal compound process
EP3119756B9 (en) 2014-03-19 2021-08-25 Dow AgroSciences LLC 2-(2,4-difluorophenyl)-1,1-difluoro-1-(5-substituted-pyridin-2-yl)-3-(1h-tetrazol-1-yl)propan-2-ols and processes for their preparation
WO2015143172A1 (en) 2014-03-19 2015-09-24 Viamet Pharmaceuticals, Inc. Antifungal compound process
WO2015143184A1 (en) 2014-03-19 2015-09-24 Viamet Pharmaceuticals, Inc. Antifungal compound process
JP2017512777A (ja) 2014-03-19 2017-05-25 ヴィアメット ファーマスーティカルズ，インコーポレイテッド 抗真菌化合物の調製方法
JP2017507991A (ja) 2014-03-19 2017-03-23 ヴィアメット ファーマスーティカルズ，インコーポレイテッド 抗真菌化合物の調製方法
EP3119764B1 (en) 2014-03-19 2019-04-17 Viamet Pharmaceuticals (NC), Inc. Antifungal compound process
EP3119754A4 (en) 2014-03-19 2017-12-13 Viamet Pharmaceuticals, Inc. Antifungal compound process
US10000465B2 (en) 2014-03-19 2018-06-19 Mycovia Pharmaceuticals, Inc. Antifungal compound process
DK3271347T3 (da) 2015-03-19 2022-07-18 Mycovia Pharmaceuticals Inc Antifungale forbindelser og fremstillingsfremgangsmåder
KR20180000731A (ko) 2015-05-18 2018-01-03 비아멧 파마슈티컬즈, 인코포레이티드 항진균성 화합물
EA036098B1 (ru) 2015-09-18 2020-09-28 ВиПиЭс-3, ИНК. Способ получения противогрибковых соединений
TWI637948B (zh) 2015-11-17 2018-10-11 維愛美製藥公司 製備４－（（６－（２－（２，４－二氟苯基）－１，１－二氟－２－羥基－３－（１ｈ－１，２，４－三唑－１－基）丙基）吡啶－３－基）氧基）苄腈之方法
CA3005738C (en) 2015-11-17 2023-10-31 Dow Agrosciences Llc 4-((6-(2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1h-1,2,4-triazol-1-yl)propyl)pyridin-3-yl)oxy)benzonitrile and processes of preparation
EP3377475A4 (en) 2015-11-17 2019-04-10 Dow Agrosciences Llc 4 - ((6-2- (2,4-difluorophenyl) -1,1-DIFLUORO-2-HYDROXY-3- (1H-1,2,4-TRIAZOL-1-YL) PROPYL) PYRIDIN-3-YL ) OXY) BENZONITRILE AND METHODS OF PREPARATION
US20180327359A1 (en) 2015-11-17 2018-11-15 Dow Agrosciences Llc 4-((6-(2-(2,4-difluorophenyl)-1,1-difluoro-2-oxoethyl)pyridin-3-yl)oxy)benzonitrile and processes of preparation
CA3006469C (en) 2015-12-30 2023-01-10 Vps-3, Inc. Metalloenzyme inhibitor compounds

Also Published As

Publication number Publication date
EP3119771A4 (en) 2017-11-22
EP3119771A1 (en) 2017-01-25
BR112016021282A2 (US07223432-20070529-C00017.png) 2017-08-15
CA2942930A1 (en) 2015-09-24
CN106459022B (zh) 2019-08-02
BR112016021282A8 (pt) 2021-07-20
US20190177298A1 (en) 2019-06-13
AU2015231208B2 (en) 2019-04-04
KR20160138013A (ko) 2016-12-02
CN106459022A (zh) 2017-02-22
US20170144990A1 (en) 2017-05-25
WO2015143154A1 (en) 2015-09-24
EP3119771B1 (en) 2020-05-06
JP2017507993A (ja) 2017-03-23
EA201691648A1 (ru) 2017-01-30
AU2015231208A1 (en) 2016-10-06
ES2800905T3 (es) 2021-01-05
MX2016012053A (es) 2017-04-27
MX369357B (es) 2019-11-06
US10077250B2 (en) 2018-09-18

Similar Documents

Publication Publication Date Title
JP6606508B2 (ja) 抗真菌化合物の調製方法
JP6572234B2 (ja) 抗真菌化合物の調製方法
US10836740B2 (en) Antifungal compound process
US10407392B2 (en) Antifungal compound process
JP2017509646A (ja) 抗真菌化合物の調製方法
JP6509897B2 (ja) 抗真菌化合物の調製方法
US10421741B2 (en) Antifungal compound process
JP2017509638A (ja) 抗真菌化合物の調製方法
JP2017512777A (ja) 抗真菌化合物の調製方法

Legal Events

Date Code Title Description
A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20180302

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20181122

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20181218

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20190214

A02 Decision of refusal

Free format text: JAPANESE INTERMEDIATE CODE: A02

Effective date: 20190326

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20190702

A911 Transfer to examiner for re-examination before appeal (zenchi)

Free format text: JAPANESE INTERMEDIATE CODE: A911

Effective date: 20190912

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20191001

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20191018

R150 Certificate of patent or registration of utility model

Ref document number: 6606508

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

LAPS Cancellation because of no payment of annual fees