JP5735986B2 - 新規抗マラリア剤 - Google Patents

新規抗マラリア剤 Download PDF

Info

Publication number
JP5735986B2
JP5735986B2 JP2012548527A JP2012548527A JP5735986B2 JP 5735986 B2 JP5735986 B2 JP 5735986B2 JP 2012548527 A JP2012548527 A JP 2012548527A JP 2012548527 A JP2012548527 A JP 2012548527A JP 5735986 B2 JP5735986 B2 JP 5735986B2
Authority
JP
Japan
Prior art keywords
pyridin
phenyl
amine
methylsulfonyl
amino
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
JP2012548527A
Other languages
English (en)
Japanese (ja)
Other versions
JP2013517264A (ja
JP2013517264A5 (enExample
Inventor
ジョン ウィッティ、マイケル
ジョン ウィッティ、マイケル
ハーディック、デイヴィッド
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
MMV Medicines for Malaria Venture
Original Assignee
MMV Medicines for Malaria Venture
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 MMV Medicines for Malaria Venture filed Critical MMV Medicines for Malaria Venture
Publication of JP2013517264A publication Critical patent/JP2013517264A/ja
Publication of JP2013517264A5 publication Critical patent/JP2013517264A5/ja
Application granted granted Critical
Publication of JP5735986B2 publication Critical patent/JP5735986B2/ja
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • C07D213/60—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 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
    • C07D213/72—Nitrogen atoms
    • C07D213/73—Unsubstituted amino or imino radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A61P33/06—Antimalarials
    • 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
    • C07D213/60—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 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
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D401/10—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 aromatic rings
    • 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
    • C07D401/14—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 three or more hetero rings
    • 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
    • C07D405/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D413/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D413/10—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 aromatic rings
    • 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
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic 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
    • C07D471/02—Heterocyclic 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
    • C07D471/04—Ortho-condensed systems
    • Y—GENERAL 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
JP2012548527A 2010-01-18 2011-01-17 新規抗マラリア剤 Expired - Fee Related JP5735986B2 (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US29582110P 2010-01-18 2010-01-18
US61/295,821 2010-01-18
PCT/IB2011/050192 WO2011086531A2 (en) 2010-01-18 2011-01-17 New anti-malarial agents

Publications (3)

Publication Number Publication Date
JP2013517264A JP2013517264A (ja) 2013-05-16
JP2013517264A5 JP2013517264A5 (enExample) 2014-02-13
JP5735986B2 true JP5735986B2 (ja) 2015-06-17

Family

ID=43759659

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2012548527A Expired - Fee Related JP5735986B2 (ja) 2010-01-18 2011-01-17 新規抗マラリア剤

Country Status (17)

Country Link
US (1) US9024033B2 (enExample)
EP (1) EP2526090B1 (enExample)
JP (1) JP5735986B2 (enExample)
CN (1) CN102812006B (enExample)
BR (1) BR112012017713A2 (enExample)
CA (1) CA2787121C (enExample)
DK (1) DK2526090T3 (enExample)
ES (1) ES2551875T3 (enExample)
HR (1) HRP20151143T1 (enExample)
HU (1) HUE027946T2 (enExample)
ME (1) ME02315B (enExample)
PL (1) PL2526090T3 (enExample)
PT (1) PT2526090E (enExample)
RS (1) RS54339B1 (enExample)
SI (1) SI2526090T1 (enExample)
SM (1) SMT201500291B (enExample)
WO (1) WO2011086531A2 (enExample)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ593969A (en) 2008-12-19 2013-11-29 Vertex Pharma Pyrazine derivatives useful as inhibitors of atr kinase
SG185524A1 (en) 2010-05-12 2012-12-28 Vertex Pharma Compounds useful as inhibitors of atr kinase
AU2011253021A1 (en) * 2010-05-12 2012-11-29 Vertex Pharmaceuticals Incorporated 2 -aminopyridine derivatives useful as inhibitors of ATR kinase
JP2013526540A (ja) 2010-05-12 2013-06-24 バーテックス ファーマシューティカルズ インコーポレイテッド Ａｔｒキナーゼ阻害剤として有用な化合物
MX2013009953A (es) * 2011-03-04 2013-09-26 Lexicon Pharmaceuticals Inc Inhibidores de cinasa de mst1 y metodos de su uso.
WO2013049859A1 (en) 2011-09-30 2013-04-04 Vertex Pharmaceuticals Incorporated Treating pancreatic cancer and non-small cell lung cancer with atr inhibitors
MX353461B (es) 2011-09-30 2018-01-15 Vertex Pharma PROCESOS PARA PREPARAR COMPUESTOS ÚTILES COMO INHIBIDORES DE CINASA ATAXIA TELANGIECTASIA MUTADA Y Rad3 RELACIONADOS (ATR).
BR112014020212B1 (pt) 2012-02-17 2021-11-23 University Of Cape Town Aminopirazina, formulação farmacêutica, método para prevenir ou tratar malária em um paciente, processo para a preparação de um derivado de aminopirazina, e, intermediário
PT2833973T (pt) 2012-04-05 2017-12-21 Vertex Pharma Compostos úteis como inibidores da cinase atr e terapias de combinação dos mesmos
DK2904406T3 (en) 2012-10-04 2018-06-18 Vertex Pharma METHOD OF DETERMINING THE ATR INHIBITION, INCREASED DNA DAMAGE
MY184855A (en) 2013-03-15 2021-04-27 Dow Agrosciences Llc 4-amino-6-(heterocyclic)picolinates and 6-amino-2-(heterocyclic)pyrimidine-4-carboxylates and their use as herbicides
US9006250B2 (en) * 2013-03-15 2015-04-14 Dow Agrosciences Llc 4-amino-6-(heterocyclic)picolinates and 6-amino-2-(heterocyclic)pyrimidine-4-carboxylates and their use as herbicides
US9862711B2 (en) 2014-04-24 2018-01-09 Novartis Ag Pyrazine derivatives as phosphatidylinositol 3-kinase inhibitors
US10112926B2 (en) * 2014-04-24 2018-10-30 Novartis Ag Amino pyridine derivatives as phosphatidylinositol 3-kinase inhibitors
WO2015162459A1 (en) 2014-04-24 2015-10-29 Novartis Ag Amino pyrazine derivatives as phosphatidylinositol 3-kinase inhibitors
CN107531683B (zh) * 2015-03-20 2022-05-13 豪夫迈·罗氏有限公司 Usp7抑制剂化合物及使用方法
EP3118198A1 (en) 2015-07-13 2017-01-18 MMV Medicines for Malaria Venture Anti-malarial agents
HK1258570A1 (zh) 2015-09-30 2019-11-15 Vertex Pharmaceuticals Inc. 使用dna损伤剂及atr抑制剂的组合治疗癌症的方法
WO2017067881A1 (en) * 2015-10-19 2017-04-27 Glaxosmithkline Intellectual Property Development Limited Pyrazine compounds for use in the treatment of parasitic protozoal infections
GB201603104D0 (en) * 2016-02-23 2016-04-06 Ucb Biopharma Sprl Therapeutic agents
EP3254679A1 (de) 2016-06-09 2017-12-13 Christian-Albrechts-Universität zu Kiel Wirkstoffe gegen protozoen und bakterien
US11919902B2 (en) * 2017-12-22 2024-03-05 Hibercell, Inc. Aryl-bipyridine amine derivatives as phosphatidylinositol phosphate kinase inhibitors
BR112020018094A2 (pt) 2018-03-08 2020-12-22 Incyte Corporation Compostos de aminopirazina diol como inibidores de pi3k-¿
WO2020010003A1 (en) 2018-07-02 2020-01-09 Incyte Corporation AMINOPYRAZINE DERIVATIVES AS PI3K-γ INHIBITORS
EP3842100A1 (en) * 2019-12-24 2021-06-30 The Board Of Regents Of The University Of Texas System Anti-malarial agents
CA3264304A1 (en) 2022-08-09 2024-02-15 Merck Patent Gmbh FURO-PYRIMIDINE DERIVATIVES
WO2024033280A1 (en) 2022-08-09 2024-02-15 Merck Patent Gmbh Furopyridin and furopyrimidin, inhibitors of pi4k, for use in the treatment of parasite infection and malaria
EP4574143A1 (en) 2023-12-21 2025-06-25 Universität Regensburg Inhibitors of plasmodia remodeling enzymes

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100574350B1 (ko) 2004-08-31 2006-04-27 한국화학연구원 2-아미노피리딘 유도체의 제조방법
JP2009507824A (ja) * 2005-09-12 2009-02-26 カウンシル・オブ・サイエンティフィック・アンド・インダストリアル・リサーチ 抗マラリアベイリス−ヒルマン付加物およびその調製方法
EP1900727A1 (en) * 2006-08-30 2008-03-19 Cellzome Ag Aminopyridine derivatives as kinase inhibitors
CN101555248B (zh) 2009-05-22 2011-06-22 北京欧凯纳斯科技有限公司 一种多取代1,5-萘啶化合物的制备方法

Also Published As

Publication number Publication date
JP2013517264A (ja) 2013-05-16
SMT201500291B (it) 2016-01-08
HK1175472A1 (zh) 2013-07-05
CA2787121A1 (en) 2011-07-21
ME02315B (me) 2016-06-20
HRP20151143T1 (hr) 2015-12-04
ES2551875T3 (es) 2015-11-24
WO2011086531A2 (en) 2011-07-21
RS54339B1 (sr) 2016-02-29
PL2526090T3 (pl) 2016-04-29
EP2526090B1 (en) 2015-08-19
HUE027946T2 (en) 2016-11-28
US9024033B2 (en) 2015-05-05
CA2787121C (en) 2018-07-17
CN102812006A (zh) 2012-12-05
WO2011086531A3 (en) 2011-09-29
CN102812006B (zh) 2016-01-20
US20120295905A1 (en) 2012-11-22
SI2526090T1 (sl) 2015-11-30
EP2526090A2 (en) 2012-11-28
DK2526090T3 (en) 2015-10-19
PT2526090E (pt) 2015-11-30
BR112012017713A2 (pt) 2020-06-23

Similar Documents

Publication Publication Date Title
JP5735986B2 (ja) 新規抗マラリア剤
US11555026B2 (en) AHR inhibitors and uses thereof
CN109810041B (zh) 卤代烯丙基胺类ssao/vap-1抑制剂及其应用
CN102459223B (zh) 5-吡啶-3-基-1，3-二氢-吲哚-2-酮衍生物及其作为醛固酮合成酶和/或cyp11b1调节剂的用途
KR102662215B1 (ko) 치환된 피라졸로(1,5-a)피리미딘 및 의학적 장애의 치료에서의 그의 용도
JP5617919B2 (ja) テトラヒドロベンゾチオフェン化合物
CA2853024C (en) 2-thiopyrimidinones
JP6226889B2 (ja) 新規抗マラリア薬
AU2017253937A1 (en) Compounds and compositions for treating conditions associated with NLRP activity
TW201217362A (en) Heteroaryls and uses thereof
TWI891227B (zh) 用於治療與apj受體活性相關的病狀的化合物及組成物
US20120101091A1 (en) Viral polymerase inhibitors
WO2014003124A1 (ja) 新規なアミド誘導体またはその塩
CN103261193A (zh) 抑制白三烯生成的*二唑抑制剂
HK1175472B (en) New anti-malarial agents
WO2025252235A1 (zh) 一种用于调节β2整联蛋白的化合物及其药物组合物
CN115380027A (zh) 新的抗疟疾剂
RS55201B1 (sr) Antimalarijski agensi
HK1202859B (en) Anti -malarial agents

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20131214

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20131214

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20141216

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20150311

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: 20150407

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20150417

R150 Certificate of patent or registration of utility model

Ref document number: 5735986

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

LAPS Cancellation because of no payment of annual fees