JP6196551B2 - ビロキサジン塩を製造する方法及びその新規な多形 - Google Patents

ビロキサジン塩を製造する方法及びその新規な多形 Download PDF

Info

Publication number
JP6196551B2
JP6196551B2 JP2013505028A JP2013505028A JP6196551B2 JP 6196551 B2 JP6196551 B2 JP 6196551B2 JP 2013505028 A JP2013505028 A JP 2013505028A JP 2013505028 A JP2013505028 A JP 2013505028A JP 6196551 B2 JP6196551 B2 JP 6196551B2
Authority
JP
Japan
Prior art keywords
viloxazine
group
base
reaction
epichlorohydrin
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
JP2013505028A
Other languages
English (en)
Japanese (ja)
Other versions
JP2013530129A (ja
Inventor
リカン リャン
リカン リャン
パドマナブフ ピー. バット
パドマナブフ ピー. バット
デヴィッド デイン
デヴィッド デイン
ジャン−フィリップ タケ
ジャン−フィリップ タケ
アレクサンドル ペチェノフ
アレクサンドル ペチェノフ
アレクセイ トチェスノコフ
アレクセイ トチェスノコフ
レイノルド マリオー
レイノルド マリオー
Original Assignee
スパーナス ファーマシューティカルズ インコーポレイテッド
スパーナス ファーマシューティカルズ インコーポレイテッド
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 スパーナス ファーマシューティカルズ インコーポレイテッド, スパーナス ファーマシューティカルズ インコーポレイテッド filed Critical スパーナス ファーマシューティカルズ インコーポレイテッド
Publication of JP2013530129A publication Critical patent/JP2013530129A/ja
Application granted granted Critical
Publication of JP6196551B2 publication Critical patent/JP6196551B2/ja
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D265/00Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/281,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/301,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/20Hypnotics; Sedatives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/24Antidepressants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/26Psychostimulants, e.g. nicotine, cocaine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/30Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/32Alcohol-abuse
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00Drugs for disorders of the blood or the extracellular fluid
    • A61P7/12Antidiuretics, e.g. drugs for diabetes insipidus
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/04Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
    • C07C215/06Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
    • C07C215/08Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with only one hydroxy group and one amino group bound to the carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/28Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
    • C07C217/30Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
    • C07C217/32Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
    • C07C217/34Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by halogen atoms, by trihalomethyl, nitro or nitroso groups, or by singly-bound oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D265/00Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/281,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/301,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • C07D265/321,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings with oxygen atoms directly attached to ring carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Psychiatry (AREA)
  • Diabetes (AREA)
  • Addiction (AREA)
  • Anesthesiology (AREA)
  • Pain & Pain Management (AREA)
  • Urology & Nephrology (AREA)
  • Hematology (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
JP2013505028A 2010-04-12 2011-04-12 ビロキサジン塩を製造する方法及びその新規な多形 Active JP6196551B2 (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US32315110P 2010-04-12 2010-04-12
US61/323,151 2010-04-12
PCT/US2011/032013 WO2011130194A2 (en) 2010-04-12 2011-04-12 Methods for producing viloxazine salts and novel polymorphs thereof

Related Child Applications (1)

Application Number Title Priority Date Filing Date
JP2015141683A Division JP2016006062A (ja) 2010-04-12 2015-07-15 ビロキサジン塩を製造する方法及びその新規な多形

Publications (2)

Publication Number Publication Date
JP2013530129A JP2013530129A (ja) 2013-07-25
JP6196551B2 true JP6196551B2 (ja) 2017-09-13

Family

ID=44065289

Family Applications (5)

Application Number Title Priority Date Filing Date
JP2013505028A Active JP6196551B2 (ja) 2010-04-12 2011-04-12 ビロキサジン塩を製造する方法及びその新規な多形
JP2015141683A Pending JP2016006062A (ja) 2010-04-12 2015-07-15 ビロキサジン塩を製造する方法及びその新規な多形
JP2016199937A Pending JP2017039754A (ja) 2010-04-12 2016-10-11 ビロキサジン塩を製造する方法及びその新規な多形
JP2017227668A Active JP6663413B2 (ja) 2010-04-12 2017-11-28 ビロキサジン又はその薬学的に許容される塩を製造する方法
JP2019103598A Pending JP2019194191A (ja) 2010-04-12 2019-06-03 ビロキサジン塩を製造する方法及びその新規な多形

Family Applications After (4)

Application Number Title Priority Date Filing Date
JP2015141683A Pending JP2016006062A (ja) 2010-04-12 2015-07-15 ビロキサジン塩を製造する方法及びその新規な多形
JP2016199937A Pending JP2017039754A (ja) 2010-04-12 2016-10-11 ビロキサジン塩を製造する方法及びその新規な多形
JP2017227668A Active JP6663413B2 (ja) 2010-04-12 2017-11-28 ビロキサジン又はその薬学的に許容される塩を製造する方法
JP2019103598A Pending JP2019194191A (ja) 2010-04-12 2019-06-03 ビロキサジン塩を製造する方法及びその新規な多形

Country Status (8)

Country Link
US (7) US9403783B2 (https=)
EP (1) EP2558437B1 (https=)
JP (5) JP6196551B2 (https=)
AU (1) AU2011240773C1 (https=)
CA (4) CA3215310A1 (https=)
ES (1) ES2552166T3 (https=)
MX (5) MX347218B (https=)
WO (1) WO2011130194A2 (https=)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX347218B (es) * 2010-04-12 2017-04-20 Supernus Pharmaceuticals Inc Metodos para producir sales de viloxazina y polimorfos novedosos de las mismas.
CN110799191B (zh) 2017-06-16 2023-05-26 贝塔制药有限公司 N-(2-(2-(二甲氨基)乙氧基)-4-甲氧基-5-((4-(1-甲基-1h-吲哚-3-基)嘧啶-2-基)氨基)苯基)丙烯酰胺及其盐的药物制剂
CN108760719A (zh) * 2018-08-17 2018-11-06 北京理工大学 一种利用拉曼光谱分析cl-20的晶型纯度的方法
KR20260023103A (ko) 2021-03-18 2026-02-20 슈퍼너스 파마슈티컬스, 인크. 치환된 몰폴린의 유도체 및 이의 용도
KR20250134715A (ko) * 2022-03-18 2025-09-11 슈퍼너스 파마슈티컬스, 인크. 치환된 몰폴린의 유도체의 제조 방법
WO2023248154A1 (en) * 2022-06-22 2023-12-28 Glenmark Life Sciences Limited Process for the preparation of viloxazine hydrochloride
EP4317141A1 (en) 2022-08-04 2024-02-07 Curia Spain S.A.U. Process and intermediates for the preparation of viloxazine and other 2-substituted morpholine derivatives
CN119707868A (zh) * 2023-09-27 2025-03-28 西安远大科创医药科技有限公司 一种盐酸维洛沙嗪产品杂质及其合成方法与应用
CN119707851A (zh) * 2023-09-27 2025-03-28 西安远大科创医药科技有限公司 一种盐酸维洛沙嗪产品杂质及其合成方法与应用
KR20250094621A (ko) * 2023-12-18 2025-06-25 주식회사 아스트로젠 (s)-빌록사진 또는 이의 염의 개선된 제조 방법
WO2025219523A1 (en) 2024-04-19 2025-10-23 Cambrex Profarmaco Milano S.R.L. "intermediates and processes for the preparation of viloxazine"

Family Cites Families (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1138405A (en) 1966-12-28 1969-01-01 Ici Ltd Morpholine derivatives
US3712890A (en) * 1969-06-20 1973-01-23 Ici Ltd Process for making 2-aryloxymethyl morpholines
US3857839A (en) * 1969-06-20 1974-12-31 Ici Ltd For cyclising 1-aryloxy-3 beta-substituted ethylamino-2-propanols
ES411826A1 (es) * 1973-02-20 1976-01-01 Liade Sa Lab Procedimiento de obtencion de 1-ariloxi - 2 - propanolami- nas farmacologicamente activos.
JPS5188972A (en) 1975-01-29 1976-08-04 22*77 indeniruokishimechiru **4 chikanmoruhorinjudotainoseiho
JPS5283677A (en) 1976-01-01 1977-07-12 Yamanouchi Pharmaceut Co Ltd Derivative of 2-(7-indenyloxymethyl)-4-substituted morpholine
US4711887A (en) * 1982-04-23 1987-12-08 Imperial Chemical Industries Plc Hydrazinopyridazine compounds
JPH06306025A (ja) * 1992-11-30 1994-11-01 Sankyo Co Ltd ジアリールアルカン誘導体
US5760069A (en) * 1995-02-08 1998-06-02 Boehringer Mannheim Pharmaceuticals Corporation-Smithkline Beecham Corporation Limited Partnership #1 Method of treatment for decreasing mortality resulting from congestive heart failure
CA2214034A1 (en) * 1995-03-10 1996-09-19 University Of Iowa Research Foundation Preparation of n-arylmethyl aziridine derivatives, 1,4,7,10-tetraazacyclododecane derivatives obtained therefrom and n-arylmethyl-ethanol-amine sulphonate esters as intermediates
AUPO565997A0 (en) * 1997-03-17 1997-04-10 Fujisawa Pharmaceutical Co., Ltd. Propanolamine derivatives
US6953855B2 (en) * 1998-12-11 2005-10-11 Targacept, Inc. 3-substituted-2(arylalkyl)-1-azabicycloalkanes and methods of use thereof
DE19919153A1 (de) * 1999-04-27 2000-11-02 Consortium Elektrochem Ind Herstellung von acrylierten flüssigkristallinen Verbindungen
FR2796069B3 (fr) * 1999-07-09 2001-08-24 Sanofi Synthelabo Nouveaux procedes de preparation de derives de 2-(2- arylmorpholin-2-yl)ethanol substitues, enantiomeriquement purs, et composes intermediaires utiles dans ces procedes
PT1257277E (pt) * 2000-02-24 2005-09-30 Pharmacia & Upjohn Co Llc Novas combinacoes de farmacos
US20030040436A1 (en) * 2000-10-23 2003-02-27 Emerson Ralph W. Use of benzyl ester compositions for controlling non-arthropod pest populations
TWI329105B (en) * 2002-02-01 2010-08-21 Rigel Pharmaceuticals Inc 2,4-pyrimidinediamine compounds and their uses
US7326790B2 (en) * 2003-05-02 2008-02-05 Rigel Pharmaceuticals, Inc. Diphenylisoxazole compounds and hydro isomers thereof
JP4210573B2 (ja) * 2003-10-10 2009-01-21 花王株式会社 置換フェノキシプロパノールアミン類
CA2567935C (en) * 2004-05-27 2009-10-27 Pfizer Limited Aminopyridine derivatives as selective dopamine d3 agonists
US20060118002A1 (en) * 2004-12-03 2006-06-08 Sud-Chemie Inc. Organoclay composition containing quat mixtures
KR20080045266A (ko) * 2005-09-06 2008-05-22 스미스클라인 비참 코포레이션 벤즈이미다졸 티오펜을 제조하기 위한 위치선택적인 방법
PE20070855A1 (es) * 2005-12-02 2007-10-14 Bayer Pharmaceuticals Corp Derivados de 4-amino-pirrolotriazina sustituida como inhibidores de quinasas
CN100415709C (zh) * 2006-05-15 2008-09-03 西北大学 β-(3,4-二羟基苯基)-α-羟基丙酸冰片酯、其合成方法和用途
WO2008047388A2 (en) 2006-10-20 2008-04-24 Ind-Swift Laboratories Limited Improved process for the preparation of ranolazine
ES2539947T3 (es) * 2008-06-02 2015-07-07 Cipla Limited Procedimiento para la síntesis de arformoterol
EP2341912B1 (en) * 2008-09-05 2014-01-22 Supernus Pharmaceuticals, Inc. Method of treatment of attention deficit/hyperactivity disorder (adhd)
US9296940B2 (en) * 2009-12-21 2016-03-29 Baker Hughes Incorporated Dithiazine derivatives
MX347218B (es) * 2010-04-12 2017-04-20 Supernus Pharmaceuticals Inc Metodos para producir sales de viloxazina y polimorfos novedosos de las mismas.
TWI596088B (zh) * 2011-01-25 2017-08-21 陶氏農業科學公司 4-胺基-6-(經取代的苯基)吡啶甲酸酯及6-胺基-2-(經取代的苯基)-4-嘧啶羧酸酯之芳烷酯以及其等作為除草劑之用途
EP2922849B1 (en) * 2012-11-21 2017-07-12 RaQualia Pharma Inc. Polymorphs of 4-{[4-({[4-(2,2,2-trifluoroethoxy)-1,2-benzisoxazol-3-yl]oxy}methyl)piperidin-1-yl]methyl}-tetrahydro-2h-pyran-4-carboxylic acid as 5-hydroxytryptamine-4 (5-ht4) receptor agonists for the treatment of gastrointestinal diseases

Also Published As

Publication number Publication date
MX357613B (es) 2018-07-17
WO2011130194A2 (en) 2011-10-20
CA2795408C (en) 2018-03-13
CA2992219A1 (en) 2011-10-20
JP2016006062A (ja) 2016-01-14
ES2552166T3 (es) 2015-11-26
US20110251198A1 (en) 2011-10-13
WO2011130194A3 (en) 2012-01-05
US20260008759A1 (en) 2026-01-08
US20190300492A1 (en) 2019-10-03
AU2011240773B2 (en) 2015-04-02
US9434703B2 (en) 2016-09-06
EP2558437A2 (en) 2013-02-20
US10005743B2 (en) 2018-06-26
MX2012011821A (es) 2012-11-30
US9403783B2 (en) 2016-08-02
US20180265482A1 (en) 2018-09-20
EP2558437B1 (en) 2015-08-05
CA3126096C (en) 2023-11-21
JP2017039754A (ja) 2017-02-23
US20220024885A1 (en) 2022-01-27
MX347218B (es) 2017-04-20
AU2011240773A1 (en) 2012-11-01
MX357614B (es) 2018-07-17
AU2011240773C1 (en) 2015-08-27
JP2013530129A (ja) 2013-07-25
CA2795408A1 (en) 2011-10-20
US10160733B2 (en) 2018-12-25
MX355697B (es) 2018-04-27
CA3126096A1 (en) 2011-10-20
US20150126735A1 (en) 2015-05-07
US20160304475A1 (en) 2016-10-20
CA3215310A1 (en) 2011-10-20
JP6663413B2 (ja) 2020-03-11
JP2019194191A (ja) 2019-11-07
JP2018076325A (ja) 2018-05-17

Similar Documents

Publication Publication Date Title
JP6196551B2 (ja) ビロキサジン塩を製造する方法及びその新規な多形
EP2705028B1 (en) Process for the preparation of a rivaroxaban and intermediates formed in said process
CN110590757A (zh) 一种泊沙康唑的制备方法
JP2004530638A (ja) 結晶性ベンラファクシン塩基、及び新規なベンラファクシン塩酸塩多型形状、ならびにその調製方法
RU2137769C1 (ru) Способ получения эпоксида
WO2015124764A1 (en) Synthesis process of dabigatran etexilate mesylate, intermediates of the process and novel polymorph of dabigatran etexilate
US6117999A (en) Methods of making HIV-protease inhibitors and intermediates for making HIV-protease inhibitors
CN107406386A (zh) 用于生产1‑(4‑羟基苯基)‑4‑(4‑三氟甲氧基苯氧基)哌啶或其盐的方法
EP1948625A1 (en) Process for the preparation of betamimetic benzoxazinone derivatives
US6084107A (en) Intermediates for making HIV-protease inhibitors
JP2003055375A (ja) 光学活性ヒドラジン化合物の製造法
JP2005047808A (ja) メチル化合物の製造方法
JP2006036641A (ja) メチル化合物の製造法

Legal Events

Date Code Title Description
A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20140328

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20150317

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20150612

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20150715

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20150915

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20151215

A02 Decision of refusal

Free format text: JAPANESE INTERMEDIATE CODE: A02

Effective date: 20160301

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20160630

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

Free format text: JAPANESE INTERMEDIATE CODE: A911

Effective date: 20160707

A912 Re-examination (zenchi) completed and case transferred to appeal board

Free format text: JAPANESE INTERMEDIATE CODE: A912

Effective date: 20160805

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20170605

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20170818

R150 Certificate of patent or registration of utility model

Ref document number: 6196551

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