JP5596680B2 - 経口抗がん製剤 - Google Patents
経口抗がん製剤 Download PDFInfo
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- JP5596680B2 JP5596680B2 JP2011517646A JP2011517646A JP5596680B2 JP 5596680 B2 JP5596680 B2 JP 5596680B2 JP 2011517646 A JP2011517646 A JP 2011517646A JP 2011517646 A JP2011517646 A JP 2011517646A JP 5596680 B2 JP5596680 B2 JP 5596680B2
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- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/59—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
- A61K47/60—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes the organic macromolecular compound being a polyoxyalkylene oligomer, polymer or dendrimer, e.g. PEG, PPG, PEO or polyglycerol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/08—Solutions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Description
本出願は、2008年7月11日に出願された米国特許出願第12/171515号に基づく優先権を主張するものである。前記先願の内容は、その全体の内容が参照により本明細書に組み込まれる。
がんは、先進国において死亡原因となっている。診断および治療計画が日々進歩しているにもかかわらず、ほとんどの現行の治療方法は望ましくない副作用があり、限られた有効性しかない。腫瘍の構造および腫瘍の転移が関与するメカニズムが多様であることから、がんの治療は、複雑である。これらの多くは未だよく分かっていない。化学療法は、主に白血病などのがんにおいて第1選択であり、不応性固形癌などのがんにおいて第2選択である。
本発明は、一部では、N−(3−メチルイソチアゾール−5−イル)−2−[1−(3−メチルイソキサゾール−5−イルメチル)−1H−インドール−3−イル]−2−オキソアセトアミドを含む経口製剤が、予想外に、経口によるバイオアベイラビリティを高めるという発見に基づくものである。
インドール(1.17 g, 10 mmol)の10mLテトラヒドロフラン溶液に、カリウムtert−ブトキシド(1.34 g, 12 mmol)の10mLテトラヒドロフラン懸濁液を滴下した。反応混合物を室温で2時間撹拌し、次いで5−(クロロメチル)−3−メチルイソキサゾール(1.32 g, 10mmol)の5mLテトラヒドロフラン溶液を滴下した。前記溶液を4時間放置し、次いで、10mL飽和塩化アンモニウムを撹拌しながら添加した。前記混合物を合計60mLのエーテルで3回抽出し、有機層を無水硫酸マグネシウムで乾燥した後、ろ過した。得られたろ液を真空下で濃縮し、シリカゲルのフラッシュクロマトグラフィで精製した。用いた展開溶媒はn−ヘキサンおよび酢酸エチル8:1(w/w)の混合液であった。収率:1.61g、76%。
NMR:10.33 (s, 1H), 9.15 (s, 1H), 8.44 (d, J = 6.3 Hz, 1H), 7.45-7.38 (m, 3H), 6.82 (s, 1H), 5.96 (s, 1H), 5.48 (s, 2H), 2.49 (s, 3H), 2.52 (s, 3H).
MS (M+1): 381.1.
実施例2:TPGS、トランスクトール、およびPEGを含むBPR0C261製剤の調製
はじめに、BRCOC261(5 mg)をトランスクトール(99 mg)に溶解した。次いで、前記溶液にPEG400(300 mg)を添加した。TPGS(105 mg)を融解するまで60〜70℃で加熱した。融解したTPGSをトランスクトール/PEG溶液に撹拌しながら添加して均一の溶液とした。前記溶液を透明な溶液となるまでさらに40℃で撹拌した。
実施例3:異なるキャリアにおけるBPR0C261の溶解度
異なる薬剤キャリアまたは混合キャリアにおけるBRCOC261の溶解度を評価した。前記溶解度を、室温におけるキャリアまたは混合キャリア中に溶解する化合物の最大量と定義する。結果を下記表1に示す。
BPR0C261の経口バイオアベイラビリティは、本明細書中に記載された様々な経口製剤におけるBPR0C261の経口投与(「po」)によって得られた薬物動態学的(「PK」)特性と、BPR0C261の静脈内投与(「IV」)によって得られたPKとを比較することによって評価した。
本発明の詳細な説明に開示されたすべての特徴は、いかなる組み合わせによっても結合されうる。同一、等価、または類似の目的で得られるその他の特徴は、本発明の詳細な説明に開示されたそれぞれの特徴と置換されうる。したがって、明示に他の記載がない限り、開示されるそれぞれの特徴は、等価または類似する特徴を包括する系列の例である。
Claims (11)
- d−アルファ−トコフェリルポリエチレングリコール1000コハク酸エステル(「TPGS」);
2−(2−エトキシエトキシ)エタノール(「トランスクトール」);および
N−(3−メチルイソチアゾール−5−イル)−2−[1−(3−メチルイソキサゾール−5−イルメチル)−1H−インドール−3−イル]−2−オキソアセトアミドの有効量;
を含み、前記TPGSが10〜80重量%であり、前記トランスクトールが10〜60重量%である、経口投与される、医薬製剤。 - 前記TPGSがキャリアの20〜75重量%であり、前記トランスクトールがキャリアの20〜25重量%である、請求項1に記載の製剤。
- 300〜6000の範囲の分子量を有するポリエチレングリコール(「PEG」)をさらに含む、請求項1または2に記載の製剤。
- 前記PEGが、400〜1000の範囲の分子量を有する、請求項3に記載の製剤。
- 前記PEGが10〜70重量%である、請求項3または4に記載の製剤。
- 前記PEGが30〜70重量%であり、前記TPGSが10〜50重量%であり、および前記トランスクトールが10〜30重量%である、請求項5に記載の製剤。
- 前記PEGが40〜65重量%であり、前記TPGSが15〜40重量%であり、および前記トランスクトールが15〜25重量%である、請求項6に記載の製剤。
- カプセルに封入された、請求項1〜7のいずれか1項に記載の製剤。
- 前記カプセルが、ブタコラーゲン物質、ウシコラーゲン物質、ゼラチン、アラビアゴム、ペクチン、ポリ(エチレン−co−無水マレイン酸)、ポリ(ビニルメチルエーテル−co−無水マレイン酸)、カラギナン、および寒天からなる群から選択される少なくとも1つのポリマーから形成される、請求項8に記載の製剤。
- 前記製剤が、グリセリド、脂肪酸、および脂肪酸エステルを含まない、請求項1〜9のいずれか1項に記載の製剤。
- がんの治療に用いられる、請求項1〜10のいずれか1項に記載の製剤。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/171,515 US8026271B2 (en) | 2008-07-11 | 2008-07-11 | Formulations of indol-3-yl-2-oxoacetamide compounds |
US12/171,515 | 2008-07-11 | ||
PCT/US2009/050210 WO2010006234A2 (en) | 2008-07-11 | 2009-07-10 | Anticancer oral formulation |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2011527704A JP2011527704A (ja) | 2011-11-04 |
JP2011527704A5 JP2011527704A5 (ja) | 2012-08-16 |
JP5596680B2 true JP5596680B2 (ja) | 2014-09-24 |
Family
ID=41505721
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011517646A Expired - Fee Related JP5596680B2 (ja) | 2008-07-11 | 2009-07-10 | 経口抗がん製剤 |
Country Status (8)
Country | Link |
---|---|
US (1) | US8026271B2 (ja) |
EP (1) | EP2310363B1 (ja) |
JP (1) | JP5596680B2 (ja) |
KR (1) | KR101627382B1 (ja) |
CN (1) | CN102159541B (ja) |
ES (1) | ES2426599T3 (ja) |
TW (1) | TWI384984B (ja) |
WO (1) | WO2010006234A2 (ja) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8026271B2 (en) * | 2008-07-11 | 2011-09-27 | National Health Research Institutes | Formulations of indol-3-yl-2-oxoacetamide compounds |
AU2010273816B2 (en) | 2009-06-29 | 2015-07-09 | Incyte Holdings Corporation | Pyrimidinones as PI3K inhibitors |
WO2011075643A1 (en) | 2009-12-18 | 2011-06-23 | Incyte Corporation | Substituted heteroaryl fused derivatives as pi3k inhibitors |
WO2011075630A1 (en) * | 2009-12-18 | 2011-06-23 | Incyte Corporation | Substituted fused aryl and heteroaryl derivatives as pi3k inhibitors |
WO2011130342A1 (en) | 2010-04-14 | 2011-10-20 | Incyte Corporation | FUSED DERIVATIVES AS ΡI3Κδ INHIBITORS |
US9062055B2 (en) | 2010-06-21 | 2015-06-23 | Incyte Corporation | Fused pyrrole derivatives as PI3K inhibitors |
EP2655374B1 (en) | 2010-12-20 | 2019-10-23 | Incyte Holdings Corporation | N-(1-(substituted-phenyl)ethyl)-9h-purin-6-amines as pi3k inhibitors |
WO2012125629A1 (en) | 2011-03-14 | 2012-09-20 | Incyte Corporation | Substituted diamino-pyrimidine and diamino-pyridine derivatives as pi3k inhibitors |
US9126948B2 (en) | 2011-03-25 | 2015-09-08 | Incyte Holdings Corporation | Pyrimidine-4,6-diamine derivatives as PI3K inhibitors |
EP3552664A1 (en) | 2011-05-12 | 2019-10-16 | Proteostasis Therapeutics, Inc. | Proteostasis regulators |
AR087760A1 (es) | 2011-09-02 | 2014-04-16 | Incyte Corp | Heterociclilaminas como inhibidores de pi3k |
AR090548A1 (es) | 2012-04-02 | 2014-11-19 | Incyte Corp | Azaheterociclobencilaminas biciclicas como inhibidores de pi3k |
WO2015073528A1 (en) | 2013-11-12 | 2015-05-21 | Proteostasis Therapeutics, Inc. | Proteasome activity enhancing compounds |
US10077277B2 (en) | 2014-06-11 | 2018-09-18 | Incyte Corporation | Bicyclic heteroarylaminoalkyl phenyl derivatives as PI3K inhibitors |
PT3262046T (pt) | 2015-02-27 | 2020-12-24 | Incyte Corp | Sais de inibidor de pi3k e processos para a sua preparação |
US9732097B2 (en) | 2015-05-11 | 2017-08-15 | Incyte Corporation | Process for the synthesis of a phosphoinositide 3-kinase inhibitor |
US9988401B2 (en) | 2015-05-11 | 2018-06-05 | Incyte Corporation | Crystalline forms of a PI3K inhibitor |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6979456B1 (en) | 1998-04-01 | 2005-12-27 | Jagotec Ag | Anticancer compositions |
US6372251B2 (en) * | 1999-06-11 | 2002-04-16 | Abbott Laboratories | Formulations comprising lipid-regulating agents |
AU2002357012A1 (en) * | 2001-11-27 | 2003-06-10 | Transform Pharmaceuticals, Inc. | Oral pharmaceutical formulations comprising paclitaxel, derivatives and methods of administration thereof |
US6903104B2 (en) | 2001-12-06 | 2005-06-07 | National Health Research Institutes | Indol-3-YL-2-oxoacetamide compounds and methods of use thereof |
CN101065115A (zh) * | 2004-11-24 | 2007-10-31 | 默克公司 | 取代酰胺的液体和半固体口服药物制剂 |
US20060134204A1 (en) * | 2004-12-21 | 2006-06-22 | Wong Patrick S | Complexes made using low solubility drugs |
TWI376239B (en) | 2006-02-01 | 2012-11-11 | Andrew Xian Chen | Vitamin e succinate stabilized pharmaceutical compositions, methods for the preparation and the use thereof |
BRPI0717721A2 (pt) * | 2006-11-28 | 2013-10-29 | Marinus Pharmaceuticals | "partículas complexadas de drogas, composição farmacêutica, uso de uma composição farmacêutica, partículas complexadas de droga estabilizadas no tamanho, método para a preparação de partículas estabilizadas da droga, composição farmacêutica sólida, comprimido oral ingerível e composição líquida em nanopartículas estabilizadas no tamanho" |
UA100852C2 (ru) * | 2007-01-16 | 2013-02-11 | Байпар Сайенсиз, Инк. | Композиции для лечения рака |
US8026271B2 (en) * | 2008-07-11 | 2011-09-27 | National Health Research Institutes | Formulations of indol-3-yl-2-oxoacetamide compounds |
-
2008
- 2008-07-11 US US12/171,515 patent/US8026271B2/en not_active Expired - Fee Related
-
2009
- 2009-07-09 TW TW098123197A patent/TWI384984B/zh not_active IP Right Cessation
- 2009-07-10 ES ES09795224T patent/ES2426599T3/es active Active
- 2009-07-10 EP EP09795224.6A patent/EP2310363B1/en not_active Not-in-force
- 2009-07-10 CN CN200980126979.4A patent/CN102159541B/zh not_active Expired - Fee Related
- 2009-07-10 JP JP2011517646A patent/JP5596680B2/ja not_active Expired - Fee Related
- 2009-07-10 KR KR1020117003208A patent/KR101627382B1/ko not_active IP Right Cessation
- 2009-07-10 WO PCT/US2009/050210 patent/WO2010006234A2/en active Application Filing
Also Published As
Publication number | Publication date |
---|---|
CN102159541A (zh) | 2011-08-17 |
EP2310363A4 (en) | 2012-03-28 |
KR20110038135A (ko) | 2011-04-13 |
TW201002319A (en) | 2010-01-16 |
KR101627382B1 (ko) | 2016-06-03 |
TWI384984B (zh) | 2013-02-11 |
EP2310363A2 (en) | 2011-04-20 |
JP2011527704A (ja) | 2011-11-04 |
EP2310363B1 (en) | 2013-06-05 |
CN102159541B (zh) | 2014-06-04 |
US20100010059A1 (en) | 2010-01-14 |
ES2426599T3 (es) | 2013-10-24 |
US8026271B2 (en) | 2011-09-27 |
WO2010006234A2 (en) | 2010-01-14 |
WO2010006234A3 (en) | 2010-04-08 |
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