JP5354775B2 - チューブリン結合活性を有するコンブレタスタチンアナログ - Google Patents

チューブリン結合活性を有するコンブレタスタチンアナログ Download PDF

Info

Publication number
JP5354775B2
JP5354775B2 JP2008517095A JP2008517095A JP5354775B2 JP 5354775 B2 JP5354775 B2 JP 5354775B2 JP 2008517095 A JP2008517095 A JP 2008517095A JP 2008517095 A JP2008517095 A JP 2008517095A JP 5354775 B2 JP5354775 B2 JP 5354775B2
Authority
JP
Japan
Prior art keywords
trimethoxy
methoxy
dihydro
phenyl
group
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
JP2008517095A
Other languages
English (en)
Japanese (ja)
Other versions
JP2008546706A (ja
JP2008546706A5 (cg-RX-API-DMAC10.html
Inventor
ケビン ジー． ピニー，
マダビ スリラム，
Original Assignee
ベイラー ユニバーシティ
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 ベイラー ユニバーシティ filed Critical ベイラー ユニバーシティ
Publication of JP2008546706A publication Critical patent/JP2008546706A/ja
Publication of JP2008546706A5 publication Critical patent/JP2008546706A5/ja
Application granted granted Critical
Publication of JP5354775B2 publication Critical patent/JP5354775B2/ja
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • 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
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • 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
    • 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
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/12—One of the condensed rings being a six-membered aromatic ring the other ring being at least seven-membered

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Ophthalmology & Optometry (AREA)
  • Diabetes (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hematology (AREA)
  • Cardiology (AREA)
  • Emergency Medicine (AREA)
  • Vascular Medicine (AREA)
  • Oncology (AREA)
  • Endocrinology (AREA)
  • Obesity (AREA)
  • Urology & Nephrology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Dermatology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
JP2008517095A 2005-06-14 2006-06-14 チューブリン結合活性を有するコンブレタスタチンアナログ Expired - Fee Related JP5354775B2 (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US69068905P 2005-06-14 2005-06-14
US60/690,689 2005-06-14
PCT/US2006/023251 WO2006138427A2 (en) 2005-06-14 2006-06-14 Combretastatin analogs with tubulin binding activity

Publications (3)

Publication Number Publication Date
JP2008546706A JP2008546706A (ja) 2008-12-25
JP2008546706A5 JP2008546706A5 (cg-RX-API-DMAC10.html) 2009-11-26
JP5354775B2 true JP5354775B2 (ja) 2013-11-27

Family

ID=37076178

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2008517095A Expired - Fee Related JP5354775B2 (ja) 2005-06-14 2006-06-14 チューブリン結合活性を有するコンブレタスタチンアナログ

Country Status (6)

Country Link
US (2) US7429681B2 (cg-RX-API-DMAC10.html)
EP (1) EP1896391B1 (cg-RX-API-DMAC10.html)
JP (1) JP5354775B2 (cg-RX-API-DMAC10.html)
CA (1) CA2611712C (cg-RX-API-DMAC10.html)
ES (1) ES2551086T3 (cg-RX-API-DMAC10.html)
WO (1) WO2006138427A2 (cg-RX-API-DMAC10.html)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2048126A1 (de) * 2007-10-11 2009-04-15 Bayer Schering Pharma AG Benzocycloheptanderivate als selektiv wirksame Estrogene
JP5302328B2 (ja) 2007-11-21 2013-10-02 オキシジーン， インコーポレイテッド 造血性新生物を治療するための方法
WO2010132498A1 (en) * 2009-05-11 2010-11-18 Oxigene, Inc. Vascular disrupting agents for treatment of polypoidal choroidal vasculopathy
CN106822083A (zh) 2009-08-27 2017-06-13 生物学特性有限公司 用于治疗增生性疾病的联合疗法
US20150018566A1 (en) 2011-08-25 2015-01-15 The Provost, Fellows, Foundation Scholars, & the Other Members of Board, of The College of the Holy Tubulin binding agents
AU2013204313C1 (en) 2012-06-01 2016-04-07 Bionomics Limited Combination Therapy
CN104817519B (zh) * 2015-05-11 2016-11-16 中国药科大学 一类ca-4的衍生物、其制法及其医药用途
JP2018523712A (ja) 2015-08-18 2018-08-23 マテオン セラピューティクス, インク.Mateon Therapeutics, Inc. 腫瘍に対する免疫調節療法を向上させる為のｖｄａｓの使用
WO2017066668A1 (en) * 2015-10-15 2017-04-20 Baylor University Drug-linker conjugate pharmaceutical compositions
SG11201806829TA (en) * 2016-02-15 2018-09-27 Sanofi Sa 6,7-dihydro-5h-benzo[7]annulene derivatives as estrogen receptor modulators
US20180002355A1 (en) * 2016-07-01 2018-01-04 Baylor University Benzocyclooctene-based and indene-based anticancer agents
EP3541809B1 (en) 2016-11-17 2025-06-25 Sanofi Novel substituted n-(3-fluoropropyl)-pyrrolidine compounds, processes for their preparation and therapeutic uses thereof
EP3434272A1 (en) 2017-07-25 2019-01-30 Sanofi Combination comprising palbociclib and 6-(2,4-dichlorophenyl)-5-[4-[(3s)-1-(3-fluoropropyl)pyrrolidin-3-yl]oxyphenyl]-8,9-dihydro-7h-benzo[7]annulene-2-carboxylic acid
WO2020037209A1 (en) * 2018-08-17 2020-02-20 Baylor University Benzosuberene analogues and related compounds with activity as anticancer agents
DK3847157T3 (da) 2018-09-07 2022-08-08 Sanofi Sa Fremgangsmåde til fremstilling af methyl-[6-(2,4-dichlorphenyl)-5-[4-[(3s)-1-(3-fluorpropyl)pyrrolidin-3-yl]oxyphenyl]-8,9-dihydro-7h-benzo[7]annulen-2-carboxylat] og salt deraf
WO2021063967A1 (en) 2019-10-01 2021-04-08 Sanofi Novel substituted 6,7-dihydro-5h-benzo[7]annulene compounds, processes for their preparation and therapeutic uses thereof
CA3160897A1 (en) 2019-12-09 2021-06-17 Sanofi Crystalline form of a 7h-benzo[7]annulene-2-carboxylic acid derivative
TW202146007A (zh) 2020-02-27 2021-12-16 法商賽諾菲公司 包含阿培利司（ａｌｐｅｌｉｓｉｂ）與６－（２，４－二氯苯基）－５－［４－［（３ｓ）－１－（３－氟丙基）吡咯啶－３－基］氧苯基］－８，９－二氫－７ｈ－苯并［７］輪烯－２－羧酸之組合
IL302152B1 (en) 2020-10-19 2026-07-01 Sanofi Sa 6,7-DIHYDRO-5H-BENZO[7]ANNULENE COMPOUNDS AND THEIR DERIVATIVES, PROCESSES FOR THEIR PREPARATION AND THEIR THERAPEUTIC USES
IL302153B1 (en) 2020-10-19 2026-07-01 Sanofi Sa 6,7-DIHYDRO-5H-BENZO[7]ANNULENE COMPOUNDS AND THEIR DERIVATIVES, PROCESSES FOR THEIR PREPARATION AND THEIR THERAPEUTIC USES

Family Cites Families (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2447099A (en) * 1944-08-23 1948-08-17 Hoffmann La Roche 2-phenylindene derivatives and process for the manufacture of same
US2493730A (en) * 1946-10-23 1950-01-03 Hoffmann La Roche 2-(p-oxyphenyl)-3-isopropyl-6-oxyindanes
US3859358A (en) * 1967-12-20 1975-01-07 Standard Oil Co Ohio Process for the oxidation of olefins to unsaturated aldehydes
US3813430A (en) * 1970-10-26 1974-05-28 Sterling Drug Inc 1-aryl-2-alkyl or-alkenyl-3,4-dihydronaphthalenes
US3859356A (en) * 1972-07-24 1975-01-07 Sandoz Ag Benzylidene substituted bicyclic and tricyclic compounds
FR2320734A1 (fr) 1975-08-14 1977-03-11 Roussel Uclaf Nouveaux derives de l'aminomethyl benzocycloheptene et leurs sels, procede de preparation et application a titre de medicaments de ces produits
NZ225307A (en) * 1987-07-10 1991-06-25 Hoffmann La Roche Heterocyclic containing alkene derivatives and pharmaceutical compositions
US4927838A (en) 1987-07-10 1990-05-22 Hoffman-La Roche Inc. Pyridine compounds which are useful in treating a disease state characterized by an excess of platelet activating factors
JP3487598B2 (ja) * 1991-11-29 2004-01-19 オキシス・アイル・オブ・マン・リミテッド 自動酸化可能な化合物を用いることによるｓｏｄ活性のアッセイ法，自動酸化可能な化合物およびその製造
JPH06256244A (ja) * 1993-03-01 1994-09-13 Sankyo Co Ltd インデンストロール誘導体
US5561122A (en) 1994-12-22 1996-10-01 Arizona Board Of Regents Acting On Behalf Of Arizona State University Combretastatin A-4 prodrug
US5811421A (en) 1995-07-31 1998-09-22 Eli Lilly And Company Naphthyl and dihydronaphthyl intermediates, compounds, compositions, and methods
US5886025A (en) * 1997-03-06 1999-03-23 Baylor University Anti-mitotic agents which inhibit tubulin polymerization
US6162930A (en) 1998-03-06 2000-12-19 Baylor University Anti-mitotic agents which inhibit tubulin polymerization
US7001926B2 (en) * 2000-03-10 2006-02-21 Oxigene, Inc. Tubulin binding agents and corresponding prodrug constructs
WO2000048606A1 (en) * 1999-02-18 2000-08-24 Oxigene, Inc. Compositions and methods for use in targeting vascular destruction
JP4187441B2 (ja) * 1999-09-17 2008-11-26 ベイラー・ユニバーシテイ インドール含有およびコンブレタスタチン関連の抗有糸分裂および抗チューブリン重合薬剤
US7091240B2 (en) * 2000-03-10 2006-08-15 Oxigene, Inc. Tubulin binding ligands and corresponding prodrug constructs
AU4352701A (en) 2000-03-10 2001-09-24 Univ Baylor Tubulin binding ligands and corresponding prodrug constructs
US6670344B2 (en) 2000-09-14 2003-12-30 Bristol-Myers Squibb Company Combretastatin A-4 phosphate prodrug mono- and di-organic amine salts, mono- and di- amino acid salts, and mono- and di-amino acid ester salts
AUPR283801A0 (en) * 2001-02-01 2001-03-01 Australian National University, The Chemical compounds and methods
US6838584B2 (en) * 2001-05-10 2005-01-04 Merck & Co., Inc. Estrogen receptor modulators
US7011926B2 (en) * 2001-10-11 2006-03-14 Taiwan Semiconductor Manufacturing Co., Ltd. Gap forming pattern fracturing method for forming optical proximity corrected masking layer
US6919324B2 (en) * 2001-10-26 2005-07-19 Oxigene, Inc. Functionalized stilbene derivatives as improved vascular targeting agents
CA2512000C (en) * 2002-12-26 2011-08-09 Eisai Co., Ltd. Selective estrogen receptor modulator
CA2531327A1 (en) * 2003-07-03 2005-01-13 Myriad Genetics, Inc. Compounds and therapeutical use thereof

Also Published As

Publication number Publication date
US7429681B2 (en) 2008-09-30
US20090075943A1 (en) 2009-03-19
JP2008546706A (ja) 2008-12-25
CA2611712C (en) 2014-05-13
US20060293394A1 (en) 2006-12-28
ES2551086T3 (es) 2015-11-16
EP1896391A2 (en) 2008-03-12
EP1896391B1 (en) 2015-08-12
US8394859B2 (en) 2013-03-12
WO2006138427A2 (en) 2006-12-28
WO2006138427A3 (en) 2007-06-28
CA2611712A1 (en) 2006-12-28

Similar Documents

Publication Publication Date Title
US8394859B2 (en) Combretastatin analogs with tubulin binding activity
US20070082872A1 (en) Indole-containing compounds with anti-tubulin and vascular targeting activity
US7384925B2 (en) Functionalized stilbene derivatives as improved vascular targeting agents
JP2004505888A (ja) チューブリン結合リガンドおよび対応するプロドラッグ構造
CN103459361A (zh) 1，5-二苯基-戊-1，4-二烯-3-酮化合物
US7456214B2 (en) Chromene-containing compounds with anti-tubulin and vascular targeting activity
NZ517069A (en) New stilbenes with vascular damaging activity
US7091240B2 (en) Tubulin binding ligands and corresponding prodrug constructs
Kaffy et al. Synthesis and biological evaluation of vinylogous combretastatin A-4 derivatives
US7001926B2 (en) Tubulin binding agents and corresponding prodrug constructs
WO2004099139A1 (en) Indole-containing compounds with anti-tubulin and vascular targeting activity
EP3129368B1 (fr) Composés cytotoxiques inhibiteurs de la polymérisation de la tubuline
JP2013507327A (ja) 癌治療用のジ（フェニルプロパノイド）・グリセロール誘導体
US20050245489A1 (en) Chromene-containing compounds with anti-tubulin and vascular targeting activity
JP2007530428A (ja) フルオロコンブレタスタチンおよびその誘導体
CN101880222B (zh) 方酸衍生物及其制备方法
CN106061948A (zh) 水溶性的4‑氮杂鬼臼毒素类似物
CN101153024B (zh) 芳基取代咪唑啉-2-酮类衍生物及其制备方法和用途
JP2022551727A (ja) 白血病の治療または予防

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20090604

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20090604

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20100527

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20120229

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20120322

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20120615

A602 Written permission of extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A602

Effective date: 20120622

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20120719

A602 Written permission of extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A602

Effective date: 20120726

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20120820

A602 Written permission of extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A602

Effective date: 20120827

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20120919

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A821

Effective date: 20120919

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20130422

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20130722

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: 20130823

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20130826

R150 Certificate of patent or registration of utility model

Ref document number: 5354775

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

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

LAPS Cancellation because of no payment of annual fees