JP5671040B2 - ４，５，６，７−テトラクロロ−３’，６’−ジヒドロキシ−２’，４’，５’，７’−テトラヨード−３ｈ−スピロ［イソベンゾフラン−１，９’−キサンテン］−３−オン（ローズベンガル）及び関連するキサンテンを合成するプロセス - Google Patents

４，５，６，７−テトラクロロ−３’，６’−ジヒドロキシ−２’，４’，５’，７’−テトラヨード−３ｈ−スピロ［イソベンゾフラン−１，９’−キサンテン］−３−オン（ローズベンガル）及び関連するキサンテンを合成するプロセス Download PDF

Info

Publication number
JP5671040B2
JP5671040B2 JP2012529937A JP2012529937A JP5671040B2 JP 5671040 B2 JP5671040 B2 JP 5671040B2 JP 2012529937 A JP2012529937 A JP 2012529937A JP 2012529937 A JP2012529937 A JP 2012529937A JP 5671040 B2 JP5671040 B2 JP 5671040B2
Authority
JP
Japan
Prior art keywords
formula
compound
iodine
solution
acid
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
JP2012529937A
Other languages
English (en)
Japanese (ja)
Other versions
JP2013505261A (ja
JP2013505261A5 (en:Method
Inventor
シンガー ジェイミー
シンガー ジェイミー
エー． ワクター エリック
エー． ワクター エリック
シー． スコット ティモシー
シー． スコット ティモシー
ラッツ マーロン
ラッツ マーロン
バビアック ケビン
バビアック ケビン
Original Assignee
プロヴェクタス ファーマスーティカルズ，インク．
プロヴェクタス ファーマスーティカルズ，インク．
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 プロヴェクタス ファーマスーティカルズ，インク．, プロヴェクタス ファーマスーティカルズ，インク． filed Critical プロヴェクタス ファーマスーティカルズ，インク．
Publication of JP2013505261A publication Critical patent/JP2013505261A/ja
Publication of JP2013505261A5 publication Critical patent/JP2013505261A5/ja
Application granted granted Critical
Publication of JP5671040B2 publication Critical patent/JP5671040B2/ja
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C07D311/82—Xanthenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • 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
    • 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
    • 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
    • A61P31/10—Antimycotics
    • 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
    • A61P31/12—Antivirals
    • 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
    • A61P5/00—Drugs for disorders of the endocrine system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/10—Spiro-condensed systems

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Endocrinology (AREA)
  • Cardiology (AREA)
  • Dermatology (AREA)
  • Diabetes (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Reproductive Health (AREA)
  • Urology & Nephrology (AREA)
  • Virology (AREA)
  • Pulmonology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pyrane Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Medicinal Preparation (AREA)
JP2012529937A 2009-09-18 2010-09-17 ４，５，６，７−テトラクロロ−３’，６’−ジヒドロキシ−２’，４’，５’，７’−テトラヨード−３ｈ−スピロ［イソベンゾフラン−１，９’−キサンテン］−３−オン（ローズベンガル）及び関連するキサンテンを合成するプロセス Active JP5671040B2 (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US24370109P 2009-09-18 2009-09-18
US61/243,701 2009-09-18
PCT/US2010/049341 WO2011035161A1 (en) 2009-09-18 2010-09-17 Process for the synthesis of 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5'7'-tetraiodo-3h-spiro[isobenzofuran-1,9'-xanthen]-3-one (rose bengal) and related xanthenes

Publications (3)

Publication Number Publication Date
JP2013505261A JP2013505261A (ja) 2013-02-14
JP2013505261A5 JP2013505261A5 (en:Method) 2013-08-01
JP5671040B2 true JP5671040B2 (ja) 2015-02-18

Family

ID=43757167

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2012529937A Active JP5671040B2 (ja) 2009-09-18 2010-09-17 ４，５，６，７−テトラクロロ−３’，６’−ジヒドロキシ−２’，４’，５’，７’−テトラヨード−３ｈ−スピロ［イソベンゾフラン−１，９’−キサンテン］−３−オン（ローズベンガル）及び関連するキサンテンを合成するプロセス

Country Status (9)

Country Link
US (2) US8530675B2 (en:Method)
EP (1) EP2464225B8 (en:Method)
JP (1) JP5671040B2 (en:Method)
KR (1) KR101494055B1 (en:Method)
CN (1) CN102548406B (en:Method)
CA (1) CA2771988C (en:Method)
ES (1) ES2548575T3 (en:Method)
MX (1) MX2012003063A (en:Method)
WO (1) WO2011035161A1 (en:Method)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2828940C (en) 2011-03-10 2024-04-16 Provectus Pharmaceuticals, Inc. Combination of local and systemic immunomodulative therapies for enhanced treatment of cancer
US9470610B2 (en) * 2013-10-22 2016-10-18 The United States Of America As Represented By The Secretary Of The Air Force Methods for using rose bengal for detection of oxidative decomposition of contaminants
JP7015232B2 (ja) * 2018-11-21 2022-02-02 東レ・ファインケミカル株式会社 高純度のフルオレセイン類化合物の製造方法
WO2020173891A1 (en) * 2019-02-26 2020-09-03 F. Hoffmann-La Roche Ag Process for the preparation of (6s)-3-[(4s)-4-cyano-2-oxo-pyrrolidin-1-yl]-6-methyl-n-(3,4,5-trifluorophenyl)-6,7-dihydro-4h-pyrazolo[1,5-a]pyrazine-5-carboxamide
JP7512409B6 (ja) 2020-03-26 2024-07-23 プロヴェクタス ファーマテック，インク． 腫瘍学及びウイルス学におけるハロゲン化キサンテンの新規の使用
US11938182B2 (en) 2020-03-26 2024-03-26 Provectus Pharmatech, Inc. Halogenated xanthenes as vaccine adjuvants
US20240325341A1 (en) * 2023-03-29 2024-10-03 Provectus Pharmatech, Inc. Anti-bacterial effect of halogenated fluoresceins against colistin-resistant gram-negative bacteria

Family Cites Families (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE108838C (en:Method)
US1965842A (en) * 1931-11-21 1934-07-10 Nat Aniline & Chem Co Inc Production of hydroxybenzenephthaleins
US1931049A (en) * 1931-11-21 1933-10-17 Nat Aniline & Chem Co Inc Process of making dihydroxyfluoranes
US3829440A (en) * 1972-12-21 1974-08-13 Richardson Merrell Inc Xanthene derivatives
SU517222A1 (ru) 1974-10-25 1977-06-25 Институт Биофизики Министерства Здравохранения Ссср Способ получени препарата бенгальска роза, меченного радиоизотопами йода
SU792878A1 (ru) 1978-08-29 1982-02-07 Ленинградский институт ядерной физики им. Б.П.Константинова Способ получени галогенированных производных флуоресцеина,меченных радиоизотопом йода
EP0050684B1 (en) 1980-10-27 1986-01-22 Syva Company Novel ether substituted fluorescein compounds as fluorescers and quenchers
SU992516A1 (ru) 1981-06-11 1983-01-30 Ленинградский Институт Ядерной Физики Им.Б.П.Константинова Способ получени галогенированных производных флуоресцеина,меченных радиоизотопом иода -123
ES8606451A1 (es) 1985-10-28 1986-04-16 Zoster Sa Procedimiento para la obtencion de la eritrosina sodica
IN168346B (en:Method) 1987-09-07 1991-03-16 Council Scient Ind Res
US5637733A (en) * 1995-09-27 1997-06-10 Warner-Jenkinson Company, Inc. Syntheses of fluorescein compounds with excess resorcinol as a solvent
US6252024B1 (en) * 1995-10-23 2001-06-26 Novartis Ag Fluorescent N-alkylated acrylamide copolymers and optical pH sensors
US6162931A (en) * 1996-04-12 2000-12-19 Molecular Probes, Inc. Fluorinated xanthene derivatives
US5945526A (en) * 1996-05-03 1999-08-31 Perkin-Elmer Corporation Energy transfer dyes with enhanced fluorescence
US6331286B1 (en) 1998-12-21 2001-12-18 Photogen, Inc. Methods for high energy phototherapeutics
US7648695B2 (en) 1998-08-06 2010-01-19 Provectus Pharmatech, Inc. Medicaments for chemotherapeutic treatment of disease
US6372907B1 (en) * 1999-11-03 2002-04-16 Apptera Corporation Water-soluble rhodamine dye peptide conjugates
US6448407B1 (en) 2000-11-01 2002-09-10 Pe Corporation (Ny) Atropisomers of asymmetric xanthene fluorescent dyes and methods of DNA sequencing and fragment analysis
WO2002062333A1 (en) 2001-02-05 2002-08-15 The Government Of The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Use of 9h-xanthenes in a method of inhibiting viral replication targeting the nucleocapsid protein
US6800765B2 (en) * 2001-08-02 2004-10-05 Molecular Devices Corporation Fluorescent pH indicators for intracellular assays
CA2490961A1 (en) * 2002-07-01 2004-01-08 Guava Technologies, Inc. Fluorescent dyes, energy transfer couples and methods
FR2846331B1 (fr) * 2002-10-29 2006-11-17 Synth Innove Lab Phtaleines de purete elevee et leur procede de preparation
KR100853969B1 (ko) * 2003-02-28 2008-08-25 징크 이메징, 엘엘씨 이미징 시스템
EP1753467B1 (en) * 2004-06-10 2013-01-09 Provectus Pharmatech, Inc. Diagnostic agents for positron emission imaging using radiolabeled halogenated xanthenes and methods for positron emission imaging with radiolabeled halogenated xanthene diagnostic agents
CA2657691A1 (en) * 2006-06-19 2007-12-27 Vanderbilt University Methods and compositions for diagnostic and therapeutic targeting of cox-2
GB0613287D0 (en) * 2006-07-05 2006-08-16 Ge Healthcare Ltd Dye imaging agents
ITMI20061713A1 (it) * 2006-09-08 2008-03-09 St Microelectronics Srl Procedimento per la sintesi di derivati alogenati della fluoresceina utili nella produzione di dispositivi di memoria non volatile

Also Published As

Publication number Publication date
WO2011035161A1 (en) 2011-03-24
CA2771988A1 (en) 2011-03-24
HK1172212A1 (zh) 2013-04-19
EP2464225A1 (en) 2012-06-20
KR101494055B1 (ko) 2015-02-16
US9422260B2 (en) 2016-08-23
HK1172501A1 (en) 2013-04-26
JP2013505261A (ja) 2013-02-14
US20130274322A1 (en) 2013-10-17
US8530675B2 (en) 2013-09-10
CN102548406A (zh) 2012-07-04
EP2464225B1 (en) 2015-09-16
MX2012003063A (es) 2012-07-25
US20110071217A1 (en) 2011-03-24
KR20120091088A (ko) 2012-08-17
EP2464225A4 (en) 2013-03-27
ES2548575T3 (es) 2015-10-19
EP2464225B8 (en) 2017-08-23
CN102548406B (zh) 2015-04-08
CA2771988C (en) 2016-07-05

Similar Documents

Publication Publication Date Title
JP5671040B2 (ja) ４，５，６，７−テトラクロロ−３’，６’−ジヒドロキシ−２’，４’，５’，７’−テトラヨード−３ｈ−スピロ［イソベンゾフラン−１，９’−キサンテン］−３−オン（ローズベンガル）及び関連するキサンテンを合成するプロセス
CA2736097C (en) Carbazole compounds for inhibition of nf-kb activity
JP2024505735A (ja) 置換されたピリダジンフェノール系誘導体
JPWO2020004537A1 (ja) 複素環化合物およびその用途
JP2009545594A (ja) 改善された効能、安定性および安全性を有する疑似塩基ベンゾ［ｃ］フェナントリジン
US11905276B2 (en) Bicyclic compound that acts as CRBN protein regulator
EP3630759B1 (fr) Composés inhibiteurs des canaux ioniques pour le traitement du cancer
WO2001064664A1 (fr) Reactifs destines au dosage de l'oxygene actif
EP3418273B1 (fr) Dérivés de flavaglines
JPH04503513A (ja) ヒュペルジンａおよびその類似体の合成法およびその中で有用な化合物
BR112021006843A2 (pt) benzoxazol e compostos relacionados úteis como moduladores de autofagia mediada por chaperona
TW201130515A (en) Prostate specific membrane antigen inhibitors
US9273022B2 (en) Process for the synthesis of 4,5,6,7-tetrachloro-3′,6′-dihydroxy-2′, 4′, 5′7′-tetraiodo-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one (Rose Bengal) and related xanthenes
EP3943919A1 (en) Reagent for fluorescence imaging of lipid droplets in cell and tissue
BR112021003660A2 (pt) compostos úteis como moduladores de autofagia mediada por chaperonas
JP2013512216A (ja) 置換ピラゾロピリミジン類の結晶形
JP2018527387A (ja) ２，３，４，５−テトラヒドロピリジン−６−アミン誘導体
WO2019189717A1 (ja) テトラヒドロナフチルウレア誘導体の製造方法
Jiang et al. An expedient route for the practical preparation of optically active (−)-gossypol
EP0866692A1 (fr) Utilisation de derives de bicycles mono- ou dicetoniques, composes obtenus et leur application comme medicament destine au traitement des inflammations, de la migraine et des etats de chocs
CA2868508A1 (en) Schweinfurthin analogues
WO2021219135A1 (zh) 一种肌醇衍生物及其用途
HK1172501B (en) Process for the synthesis of 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodo-3h-spiro[isobenzofuran-1,9'-xanthen]-3-one (rose bengal) and related xanthenes
TW202510874A (zh) 一種大環化合物及其用途
CH618977A5 (en:Method)

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20130614

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20130614

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20140701

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20140703

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20140930

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: 20141125

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20141218

R150 Certificate of patent or registration of utility model

Ref document number: 5671040

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

S111 Request for change of ownership or part of ownership

Free format text: JAPANESE INTERMEDIATE CODE: R313113

R350 Written notification of registration of transfer

Free format text: JAPANESE INTERMEDIATE CODE: R350

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

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250