JP5911484B2 - トール様受容体9のアンタゴニストとしての(+)−モルフィナンおよびその治療的使用 - Google Patents

トール様受容体9のアンタゴニストとしての(+)−モルフィナンおよびその治療的使用 Download PDF

Info

Publication number
JP5911484B2
JP5911484B2 JP2013519642A JP2013519642A JP5911484B2 JP 5911484 B2 JP5911484 B2 JP 5911484B2 JP 2013519642 A JP2013519642 A JP 2013519642A JP 2013519642 A JP2013519642 A JP 2013519642A JP 5911484 B2 JP5911484 B2 JP 5911484B2
Authority
JP
Japan
Prior art keywords
hydrogen
hydroxy
methyl
alkyl
alkoxy
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
JP2013519642A
Other languages
English (en)
Japanese (ja)
Other versions
JP2013534208A5 (enExample
JP2013534208A (ja
Inventor
ボビー エヌ. トラウィック,
ボビー エヌ. トラウィック,
デイビッド ダブリュー. バーベリッチ,
デイビッド ダブリュー. バーベリッチ,
クリストファー ダブリュー. グロート,
クリストファー ダブリュー. グロート,
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.)
Mallinckrodt Inc
Original Assignee
Mallinckrodt Inc
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
Priority claimed from US12/837,545 external-priority patent/US20110015219A1/en
Application filed by Mallinckrodt Inc filed Critical Mallinckrodt Inc
Publication of JP2013534208A publication Critical patent/JP2013534208A/ja
Publication of JP2013534208A5 publication Critical patent/JP2013534208A5/ja
Application granted granted Critical
Publication of JP5911484B2 publication Critical patent/JP5911484B2/ja
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D217/00Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
    • C07D217/18Aralkyl radicals
    • C07D217/20Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/16Amides, e.g. hydroxamic acids
    • A61K31/165Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A61K31/167Amides, 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/47Quinolines; Isoquinolines
    • A61K31/472Non-condensed isoquinolines, e.g. papaverine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/47Quinolines; Isoquinolines
    • A61K31/485Morphinan derivatives, e.g. morphine, codeine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/04Centrally acting analgesics, e.g. opioids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D221/00Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/22Bridged ring systems
    • C07D221/28Morphinans
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D489/00Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D489/00Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
    • C07D489/02Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with oxygen atoms attached in positions 3 and 6, e.g. morphine, morphinone
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D489/00Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
    • C07D489/06Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with a hetero atom directly attached in position 14
    • C07D489/08Oxygen atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D489/00Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
    • C07D489/09Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: containing 4aH-8, 9 c-Iminoethano- phenanthro [4, 5-b, c, d] furan ring systems condensed with carbocyclic rings or ring systems
    • C07D489/10Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: containing 4aH-8, 9 c-Iminoethano- phenanthro [4, 5-b, c, d] furan ring systems condensed with carbocyclic rings or ring systems with a bridge between positions 6 and 14

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Pain & Pain Management (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Emergency Medicine (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
JP2013519642A 2010-07-16 2010-12-22 トール様受容体9のアンタゴニストとしての(+)−モルフィナンおよびその治療的使用 Expired - Fee Related JP5911484B2 (ja)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US12/837,545 2010-07-16
US12/837,545 US20110015219A1 (en) 2009-07-16 2010-07-16 (+)-Morphinans as Antagonists of Toll-Like Receptor 9 and Therapeutic Uses Thereof
US12/975,407 2010-12-22
PCT/US2010/061699 WO2012008984A1 (en) 2010-07-16 2010-12-22 (+)-morphinans as antagonists of toll-like receptor 9 and therapeutic uses thereof
US12/975,407 US9562014B2 (en) 2009-07-16 2010-12-22 (+)-morphinans as antagonists of toll-like receptor 9 and therapeutic uses thereof

Publications (3)

Publication Number Publication Date
JP2013534208A JP2013534208A (ja) 2013-09-02
JP2013534208A5 JP2013534208A5 (enExample) 2014-01-30
JP5911484B2 true JP5911484B2 (ja) 2016-04-27

Family

ID=43754707

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2013519642A Expired - Fee Related JP5911484B2 (ja) 2010-07-16 2010-12-22 トール様受容体9のアンタゴニストとしての(+)−モルフィナンおよびその治療的使用

Country Status (8)

Country Link
US (3) US9562014B2 (enExample)
EP (1) EP2593095B1 (enExample)
JP (1) JP5911484B2 (enExample)
AU (1) AU2010357625B2 (enExample)
CA (1) CA2768199C (enExample)
ES (1) ES2728701T3 (enExample)
PL (1) PL2593095T3 (enExample)
WO (1) WO2012008984A1 (enExample)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011009020A2 (en) 2009-07-16 2011-01-20 Mallinckrodt Inc. Compounds and compositions for use in phototherapy and in treatment of ocular neovascular disease and cancers
TR201809739T4 (tr) * 2009-07-16 2018-07-23 Mallinckrodt Llc Toll benzeri reseptör 9 antagonistleri olarak (+)-morfinanlar ve bunların terapötik amaçlı kullanımları.
US10363251B2 (en) 2009-07-16 2019-07-30 Mallinckrodt Llc (+)-morphinans as antagonists of toll-like receptor 9 and therapeutic uses thereof
ES2728701T3 (es) 2010-07-16 2019-10-28 Mallinckrodt Llc (+)-Morfinanos como antagonistas del receptor 9 de tipo Toll y aplicaciones terapéuticas de los mismos
HK1197191A1 (en) 2011-10-26 2015-01-09 Kempharm, Inc. Benzoic acid, benzoic acid derivatives and heteroaryl carboxylic acid conjugates of hydromorphone, prodrugs, methods of making and use thereof
CN102579444A (zh) * 2012-01-21 2012-07-18 张有成 青藤碱在制备抑制肿瘤侵袭转移的药物中的应用
GB201308440D0 (en) * 2013-05-10 2013-06-19 Dalgleish Angus Therapeutic
ES2784690T3 (es) 2013-12-05 2020-09-29 Univ Bath Nuevos compuestos opioides y sus usos
KR20170094251A (ko) 2014-12-02 2017-08-17 켐팜 인코포레이티드 옥시모르폰의 벤조산, 벤조산 유도체 및 헤테로아릴 카르복실산 콘쥬게이트, 이의 전구 약물, 제조 방법 및 용도
WO2016152965A1 (ja) * 2015-03-24 2016-09-29 東レ株式会社 低アルブミン血症の改善剤
US9757372B2 (en) * 2015-03-25 2017-09-12 Taiwanj Pharmaceuticals Co., Ltd. Toll-like receptor 4 antagonists and use in autoimmune liver diseases
EP3377095B1 (en) 2015-11-18 2020-01-01 INSERM - Institut National de la Santé et de la Recherche Médicale Methods and pharmaceutical compositions for treating rhabdomyolysis
JP2020504127A (ja) * 2017-01-05 2020-02-06 タイワンジェ ファーマシューティカルズ カンパニー リミテッドTaiwanj Pharmaceuticals Co., Ltd. モルフィナン誘導体と自己免疫、炎症または感染に関連する障害の治療に用いるモルフィナン誘導体含有組成物
WO2019018354A1 (en) * 2017-07-18 2019-01-24 Merck Patent Gmbh ANTAGONISTS OF TLR7 / 8 AND USES THEREOF
AU2019224127B2 (en) * 2018-02-23 2021-12-09 Rhodes Technologies Novel opioid compounds and uses thereof
CN109288840A (zh) * 2018-11-23 2019-02-01 中国科学院长春应用化学研究所 二元纳曲酮衍生物的应用
EP4125990A4 (en) * 2020-03-24 2024-07-03 University of Padova MORPHINE ISOMERS AND THEIR STRUCTURAL MODIFICATIONS AS NMDAR ANTAGONISTS AND NEUROPLASTIGENS
CN115260098B (zh) * 2022-06-09 2024-06-04 澳门科技大学 Abcb5抑制剂在制备多耐药性类风湿性关节炎治疗药物中的应用
WO2024204554A1 (ja) * 2023-03-29 2024-10-03 日本ケミファ株式会社 スピロ環状モルヒナン誘導体

Family Cites Families (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS55133360A (en) * 1979-04-03 1980-10-17 Tatsuya Shono Preparation of cyclic amine
US4521601A (en) * 1981-05-20 1985-06-04 The United States Of America As Represented By The Department Of Health & Human Services Practical total synthesis unnatural enantiomers of opium-derived morphinans
HU197750B (en) * 1984-07-17 1989-05-29 Alkaloida Vegyeszeti Gyar Process for n-demethylation of morphine alkaloids
US5668285A (en) * 1986-10-31 1997-09-16 The United States Of America As Represented By The Department Of Health And Human Services Total synthesis of northebaine, normophine, noroxymorphone enantiomers and derivatives via N-Nor intermediates
PT95069B (pt) 1989-08-24 1997-10-31 Searle & Co Processo para a preparacao de (+)-isomeros de derivados de endoetano/endoetanoepoximofinano, uteis como agentes anti-tussicos
JPH04273880A (ja) * 1991-02-28 1992-09-30 Ono Pharmaceut Co Ltd ジヒドロモルヒネ誘導体
US6323212B1 (en) 1992-01-23 2001-11-27 Toray Industries, Inc. Morphinan derivative and its pharmaceutical applications
EP0663401B1 (en) * 1993-07-23 2000-06-07 Toray Industries, Inc. Morphinan derivative and medicinal use
US5919826A (en) * 1996-10-24 1999-07-06 Algos Pharmaceutical Corporation Method of alleviating pain
EP1359146B1 (en) 2000-10-31 2008-04-09 Rensselaer Polytechnic Institute 4-aryl piperidines as opioid receptor binding agents
WO2002080918A1 (en) * 2001-04-02 2002-10-17 Toray Industries, Inc. Remedial or prophylactic agent for frequent urination or urinary incontinence
US20040033253A1 (en) * 2002-02-19 2004-02-19 Ihor Shevchuk Acyl opioid antagonists
GB2392670A (en) 2002-09-03 2004-03-10 Stylacats Ltd (+)-Morphine production
US7238791B1 (en) * 2005-12-16 2007-07-03 Roche Diagnostics Operations, Inc. 6-monoacetylmorphine derivatives useful in immunoassay
WO2007127624A1 (en) 2006-04-26 2007-11-08 The Uab Research Foundation Reducing cancer cell invasion using an inhibitor of toll like receptor signaling
CN101066948B (zh) 2007-05-30 2012-01-04 广东工业大学 青藤碱催化氢化还原制备氢化青藤碱的方法
WO2009012005A1 (en) 2007-07-17 2009-01-22 Mallinckrodt Inc. Preparation of n-alkylated opiates by reductive amination
MX2010001785A (es) 2007-08-15 2010-03-10 Idera Pharmaceuticals Inc Moduladores de receptores tipo larga distancia.
US8883817B2 (en) * 2007-10-18 2014-11-11 Aiko Biotechnology Combination analgesic employing opioid and neutral antagonist
US20110251229A1 (en) * 2007-10-30 2011-10-13 The Regents Of The University Of Colorado (+)-opioids and methods of use
CN101896489A (zh) * 2007-12-17 2010-11-24 马林克罗特公司 制备丁丙诺啡和丁丙诺啡的衍生物的方法
EP2222642B1 (en) * 2007-12-17 2014-02-12 Mallinckrodt LLC Process and compounds for the production of (+) opiates
CN101265266B (zh) 2008-04-23 2011-12-14 南京大学 青藤碱衍生物及其制备方法和应用
AU2009260303A1 (en) * 2008-06-17 2009-12-23 Mallinckrodt Inc. Processes for the preparation of 6- beta-hydroxy morphinan compounds
CA2730111C (en) 2008-07-10 2017-02-28 Human Biomolecular Research Institute Synthesis of metabolically stable agents for alcohol and drug abuse
EP2328899B1 (en) * 2008-09-16 2018-01-24 Mallinckrodt LLC Processes for the synthesis of five and six membered heterocyclic rings
EP2344506B1 (en) 2008-09-30 2016-02-10 Mallinckrodt LLC Processes for the alkylation of secondary amine groups of morphinan derivatives
ES2758831T3 (es) * 2008-10-30 2020-05-06 Gruenenthal Gmbh Nuevas y potentes formas de dosificación de tapentadol
KR20100090155A (ko) * 2009-02-05 2010-08-13 엘지전자 주식회사 이동 단말기 및 그의 프레즌스 정보 처리방법
WO2010096790A1 (en) 2009-02-23 2010-08-26 Mallinckrodt Inc. (+)-morphinananium n-oxides and processes for their production
JP2012518652A (ja) * 2009-02-23 2012-08-16 マリンクロッド インコーポレイテッド (+)−6−ヒドロキシ−モルフィナンまたは(+)−6−アミノ−モルフィナン誘導体
US8946419B2 (en) 2009-02-23 2015-02-03 Mallinckrodt Llc (+)-6-hydroxy-morphinan or (+)-6-amino-morphinan derivatives
CN102803267A (zh) 2009-06-11 2012-11-28 马林克罗特有限公司 通过催化氢转移的6-α-氨基N-取代的吗啡喃的制备
TR201809739T4 (tr) * 2009-07-16 2018-07-23 Mallinckrodt Llc Toll benzeri reseptör 9 antagonistleri olarak (+)-morfinanlar ve bunların terapötik amaçlı kullanımları.
ES2728701T3 (es) 2010-07-16 2019-10-28 Mallinckrodt Llc (+)-Morfinanos como antagonistas del receptor 9 de tipo Toll y aplicaciones terapéuticas de los mismos

Also Published As

Publication number Publication date
WO2012008984A1 (en) 2012-01-19
US9562014B2 (en) 2017-02-07
CA2768199A1 (en) 2012-01-19
CA2768199C (en) 2018-08-28
US20110136845A1 (en) 2011-06-09
AU2010357625A1 (en) 2012-03-01
US20170029432A1 (en) 2017-02-02
PL2593095T3 (pl) 2019-12-31
AU2010357625B2 (en) 2015-04-23
US20200172488A1 (en) 2020-06-04
US10604488B2 (en) 2020-03-31
ES2728701T3 (es) 2019-10-28
US11142502B2 (en) 2021-10-12
EP2593095A1 (en) 2013-05-22
JP2013534208A (ja) 2013-09-02
EP2593095B1 (en) 2019-03-27

Similar Documents

Publication Publication Date Title
JP2013534208A (ja) トール様受容体9のアンタゴニストとしての(+)−モルフィナンおよびその治療的使用
JP5864417B2 (ja) トール様受容体9のアンタゴニストとしての(+)−モルフィナンおよびその治療的使用
US5256669A (en) Methods and compositions for treating acute or chronic pain and drug addiction
BR112020001666A2 (pt) compostos orgânicos
US9597316B2 (en) Indole compounds for use in treating inflammation and cancer
US10363251B2 (en) (+)-morphinans as antagonists of toll-like receptor 9 and therapeutic uses thereof
CN107531670B (zh) 二芳基亚甲基哌啶衍生物及其作为δ阿片受体激动剂的用途
WO2025038406A1 (en) Design, synthesis, and biological evaluation of nitrogen-walk derivatives of nan as mu opioid receptor selective modulators
JP2021514971A (ja) 新規オピオイド化合物及びその使用
JP2003518492A (ja) オピオイド鎮痛剤とトリメブチンとの組合わせ
HK1098679A (en) Anti-itching agent
JPWO2001014382A1 (ja) モルヒナン4級アンモニウム塩誘導体を有効成分とする鎮痛薬

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20131203

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20131203

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20141030

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20141107

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20150205

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20150630

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20150929

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: 20160303

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20160329

R150 Certificate of patent or registration of utility model

Ref document number: 5911484

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

LAPS Cancellation because of no payment of annual fees