JP5357022B2 - 多機能生物活性化合物 - Google Patents

多機能生物活性化合物 Download PDF

Info

Publication number
JP5357022B2
JP5357022B2 JP2009522067A JP2009522067A JP5357022B2 JP 5357022 B2 JP5357022 B2 JP 5357022B2 JP 2009522067 A JP2009522067 A JP 2009522067A JP 2009522067 A JP2009522067 A JP 2009522067A JP 5357022 B2 JP5357022 B2 JP 5357022B2
Authority
JP
Japan
Prior art keywords
alkyl
group
compound
compound according
compounds
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
JP2009522067A
Other languages
English (en)
Japanese (ja)
Other versions
JP2009545534A (ja
JP2009545534A5 (enExample
Inventor
ウラディスラフ アイ． デイジン
Original Assignee
マヌス ファーマシューティカルズ （カナダ） リミテッド
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 マヌス ファーマシューティカルズ （カナダ） リミテッド filed Critical マヌス ファーマシューティカルズ （カナダ） リミテッド
Publication of JP2009545534A publication Critical patent/JP2009545534A/ja
Publication of JP2009545534A5 publication Critical patent/JP2009545534A5/ja
Application granted granted Critical
Publication of JP5357022B2 publication Critical patent/JP5357022B2/ja
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
    • C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
    • C07H5/06—Aminosugars
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/0215—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing natural amino acids, forming a peptide bond via their side chain functional group, e.g. epsilon-Lys, gamma-Glu
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/10—Tetrapeptides
    • C07K5/1002—Tetrapeptides with the first amino acid being neutral
    • C07K5/1016—Tetrapeptides with the first amino acid being neutral and aromatic or cycloaliphatic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/50—Cyclic peptides containing at least one abnormal peptide link
    • C07K7/52—Cyclic peptides containing at least one abnormal peptide link with only normal peptide links in the ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Biophysics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biotechnology (AREA)
  • Transplantation (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Pain & Pain Management (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Peptides Or Proteins (AREA)
  • Medicinal Preparation (AREA)
JP2009522067A 2006-08-04 2007-08-01 多機能生物活性化合物 Expired - Fee Related JP5357022B2 (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US83542806P 2006-08-04 2006-08-04
US60/835,428 2006-08-04
PCT/CA2007/001357 WO2008014613A1 (en) 2006-08-04 2007-08-01 Multifunctional bioactive compounds

Publications (3)

Publication Number Publication Date
JP2009545534A JP2009545534A (ja) 2009-12-24
JP2009545534A5 JP2009545534A5 (enExample) 2010-02-12
JP5357022B2 true JP5357022B2 (ja) 2013-12-04

Family

ID=38996830

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2009522067A Expired - Fee Related JP5357022B2 (ja) 2006-08-04 2007-08-01 多機能生物活性化合物

Country Status (10)

Country Link
US (2) US8637521B2 (enExample)
EP (1) EP2046778B1 (enExample)
JP (1) JP5357022B2 (enExample)
CN (1) CN101511823B (enExample)
AU (1) AU2007280995C1 (enExample)
BR (1) BRPI0714616A2 (enExample)
CA (1) CA2659875C (enExample)
EA (1) EA018548B1 (enExample)
MX (1) MX2009001351A (enExample)
WO (1) WO2008014613A1 (enExample)

Families Citing this family (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9006175B2 (en) 1999-06-29 2015-04-14 Mannkind Corporation Potentiation of glucose elimination
ATE385193T1 (de) 2002-03-20 2008-02-15 Mannkind Corp Inhalationsgerät
DK1786784T3 (da) 2004-08-20 2011-02-14 Mannkind Corp Katalyse af diketopiperazinsyntese
BRPI0514293B1 (pt) 2004-08-23 2022-07-19 Mannkind Corporation Sistema microparticulado para distribuição de droga
DK1928423T3 (en) 2005-09-14 2016-02-29 Mannkind Corp A method for drug formulation based on increasing the affinity of the active substances to the crystalline microparticle surfaces
CA2643464C (en) 2006-02-22 2018-09-04 Mannkind Corporation A method for improving the pharmaceutic properties of microparticles comprising diketopiperazine and an active agent
CA2571645A1 (en) * 2006-12-19 2008-06-19 Apotex Technologies Inc. Pharmaceutically acceptable salts of thymodepressin and processes for their manufacture
WO2011163272A1 (en) 2010-06-21 2011-12-29 Mannkind Corporation Dry powder drug delivery system and methods
US8485180B2 (en) 2008-06-13 2013-07-16 Mannkind Corporation Dry powder drug delivery system
CN106039494B (zh) 2008-06-13 2019-12-24 曼金德公司 干粉吸入器和用于药物输送的系统
BRPI0914308B8 (pt) 2008-06-20 2021-06-22 Mannkind Corp sistema de inalação
TWI614024B (zh) 2008-08-11 2018-02-11 曼凱公司 超快起作用胰島素之用途
US8314106B2 (en) 2008-12-29 2012-11-20 Mannkind Corporation Substituted diketopiperazine analogs for use as drug delivery agents
CA2748490C (en) * 2008-12-29 2016-10-04 Mannkind Corporation Substituted diketopiperazine analogs for use as drug delivery agents
CA2749163A1 (en) 2009-01-14 2010-07-22 The Salk Institute For Biological Studies Methods for screening and compounds that protect against amyloid diseases
WO2010105094A1 (en) 2009-03-11 2010-09-16 Mannkind Corporation Apparatus, system and method for measuring resistance of an inhaler
MY186975A (en) 2009-06-12 2021-08-26 Mannkind Corp Diketopiperazine microparticles with defined specific surface areas
AU2010282169A1 (en) 2009-08-10 2012-03-08 Immunotech Developments Inc. Vaccine having a peptide adjuvant for eliciting a specific immune response to treat viral infection and other conditions
EP2496295A1 (en) 2009-11-03 2012-09-12 MannKind Corporation An apparatus and method for simulating inhalation efforts
MY180552A (en) 2011-04-01 2020-12-02 Mannkind Corp Blister package for pharmaceutical cartridges
WO2012174472A1 (en) 2011-06-17 2012-12-20 Mannkind Corporation High capacity diketopiperazine microparticles
JP6018640B2 (ja) 2011-10-24 2016-11-02 マンカインド コーポレイション 疼痛を緩和するのに有効な鎮痛組成物並びに当該組成物を含む乾燥粉末及び乾燥粉末薬剤輸送システム
PL2812372T3 (pl) 2012-02-09 2018-12-31 Novus International Inc. Cykliczne dimery zawierające heteroatom
WO2013166110A1 (en) * 2012-05-02 2013-11-07 Yale University Tlr-agonist-conjugated antibody recruiting molecules (tlr_arms)
DK2872205T3 (en) 2012-07-12 2017-02-27 Mannkind Corp DRY POWDER FORMAL ADMINISTRATION SYSTEM
WO2014011857A1 (en) 2012-07-12 2014-01-16 Novus International Inc. Matrix and layer compositions for protection of bioactives
WO2014016787A2 (en) 2012-07-24 2014-01-30 Pharma Bio Llc Peptide-based compounds and uses thereof to treat beta-amyloid accumulation
WO2014066856A1 (en) 2012-10-26 2014-05-01 Mannkind Corporation Inhalable influenza vaccine compositions and methods
KR102391750B1 (ko) 2013-03-15 2022-04-28 맨카인드 코포레이션 미세결정성 디케토피페라진 조성물 및 방법
EP3021834A1 (en) 2013-07-18 2016-05-25 MannKind Corporation Heat-stable dry powder pharmaceutical compositions and methods
US11446127B2 (en) 2013-08-05 2022-09-20 Mannkind Corporation Insufflation apparatus and methods
WO2015148905A1 (en) 2014-03-28 2015-10-01 Mannkind Corporation Use of ultrarapid acting insulin
US10561806B2 (en) 2014-10-02 2020-02-18 Mannkind Corporation Mouthpiece cover for an inhaler
US10584306B2 (en) 2017-08-11 2020-03-10 Board Of Regents Of The University Of Oklahoma Surfactant microemulsions
CN110054619A (zh) * 2018-01-18 2019-07-26 西北农林科技大学 新型二酮哌嗪类组蛋白去乙酰化酶抑制剂
WO2020041965A1 (en) * 2018-08-28 2020-03-05 Lingdong Technology (Beijing) Co., Ltd Self-driving systems with inventory holder

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4006261A (en) * 1973-09-28 1977-02-01 Firmenich S.A. Flavoring with mixtures of theobromine and cyclic dipeptides
US4289759A (en) * 1980-06-23 1981-09-15 Ortho Pharmaceutical Corporation Immunoregulatory diketopiperazine compounds
US4331595A (en) * 1980-06-23 1982-05-25 Ortho Pharmaceutical Corporation Immunoregulatory diketopiperazine compounds
GB8427735D0 (en) * 1984-11-02 1984-12-12 Fujisawa Pharmaceutical Co Piperazine compound
DE3909379A1 (de) * 1989-03-22 1990-09-27 Cassella Ag Thienylpiperazine, verfahren zu ihrer herstellung, ihre verwendung sowie diese enthaltende arzneimittel und deren herstellung
US6331318B1 (en) 1994-09-30 2001-12-18 Emisphere Technologies Inc. Carbon-substituted diketopiperazine delivery systems
US5693338A (en) * 1994-09-29 1997-12-02 Emisphere Technologies, Inc. Diketopiperazine-based delivery systems
FR2677361A1 (fr) 1991-06-04 1992-12-11 Adir Nouveaux peptides et pseudopeptides, derives de tachykinines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
ATE188219T1 (de) * 1991-10-28 2000-01-15 Cytran Ltd Pharmazeutische dipeptid zusammensetzungen und verwendungsmethoden.
US5352461A (en) * 1992-03-11 1994-10-04 Pharmaceutical Discovery Corporation Self assembling diketopiperazine drug delivery system
FR2722787B1 (fr) * 1994-07-21 1996-10-11 Univ Claude Bernard Lyon Composes a activite anthelminthique: dicetopiperazines, precurseurs et analogues
US6103699A (en) 1996-06-07 2000-08-15 Immunotech Developments Inc. Peptide, a method for its preparation and a pharmaceutical composition containing the peptide
US6060452A (en) * 1996-03-13 2000-05-09 Cytran, Inc. Analogs of L-Glu-L-Trp having pharmacological activity
US5932579A (en) * 1996-06-18 1999-08-03 Affymax Technologies N.V. Collagenase-1 and stromelysin-1 inhibitors, pharmaceutical compositions comprising same and methods of their use
JPH10226615A (ja) * 1997-02-18 1998-08-25 Pola Chem Ind Inc アスパラギン酸フェニルアラニン環状ジペプタイド誘導体を含有する組成物
US7026322B2 (en) 1998-11-12 2006-04-11 Nereus Pharmaceuticals, Inc. Phenylahistin and the phenylahistin analogs, a new class of anti-tumor compounds
DE19937721A1 (de) * 1999-08-10 2001-02-15 Max Planck Gesellschaft Neue Diketopiperazine
US6974478B2 (en) 1999-10-22 2005-12-13 Archus Orthopedics, Inc. Prostheses, systems and methods for replacement of natural facet joints with artificial facet joint surfaces
JP2001247566A (ja) * 2000-03-03 2001-09-11 Marine Biotechnol Inst Co Ltd 新規抗カビ活性物質およびその製造法
PT1311269E (pt) * 2000-08-04 2012-05-10 Dmi Biosciences Inc Método de utilização de dicetopiperazinas e composição que contém as mesmas
US20030171379A1 (en) * 2001-12-28 2003-09-11 Jacobs Robert S. Methods of treating, preventing, or inhibiting inflammation with Mactanamide compounds
JP3846409B2 (ja) 2002-02-15 2006-11-15 株式会社村田製作所 弾性表面波装置、通信装置
KR20120101164A (ko) 2003-05-15 2012-09-12 디엠아이 바이오사이언시스, 인크 Ｔ-세포 매개성 질환의 치료 방법
BRPI0514293B1 (pt) * 2004-08-23 2022-07-19 Mannkind Corporation Sistema microparticulado para distribuição de droga

Also Published As

Publication number Publication date
EP2046778B1 (en) 2013-12-04
CN101511823A (zh) 2009-08-19
EA018548B1 (ru) 2013-08-30
JP2009545534A (ja) 2009-12-24
AU2007280995A1 (en) 2008-02-07
CA2659875C (en) 2015-01-27
WO2008014613A1 (en) 2008-02-07
US9108931B2 (en) 2015-08-18
CA2659875A1 (en) 2008-02-07
US20140179708A1 (en) 2014-06-26
EP2046778A1 (en) 2009-04-15
BRPI0714616A2 (pt) 2013-06-11
CN101511823B (zh) 2014-07-30
EA200970178A1 (ru) 2009-08-28
AU2007280995C1 (en) 2013-05-23
AU2007280995B2 (en) 2012-05-03
HK1124608A1 (en) 2009-07-17
EP2046778A4 (en) 2010-09-08
US8637521B2 (en) 2014-01-28
MX2009001351A (es) 2009-05-11
US20100048586A1 (en) 2010-02-25

Similar Documents

Publication Publication Date Title
JP5357022B2 (ja) 多機能生物活性化合物
US6232468B1 (en) Dipeptides with neurokinin-antagonistic activity
EP0148133B1 (en) Tripeptide compounds containing pyroglutamic acid and tryptophan, process for their production and therapeutic applications
EP3521301B1 (en) Polyamide compound and use thereof
JP2013523599A (ja) 新規なオピオイドのジカルボン酸結合アミノ酸及びペプチドプロドラッグ並びにその用途
JPH0229080B2 (enExample)
NZ251297A (en) Immunomodulating oligopeptides (2-5aa) possessing a long lipophilic alkyl chain and compositions thereof
JP2512482B2 (ja) １，４−ビス［（アミノアルキル及びヒドロキシアミノアルキル）アミノ］−５，８−ジヒドロキシアントラキノン類の抗腫瘍性アミノ酸及びペプチド誘導体
AU2008328485B2 (en) Novel immunoregulatory peptides, compositions and uses thereof
EP0755942A1 (en) Peptide derivative
US6228841B1 (en) Peptide derivatives
WO1997010262A1 (fr) Derives peptidiques
JPH0794424B2 (ja) 新スパガリン関連化合物およびその製造法
HK1124608B (en) Multifunctional bioactive compounds
KR20080091103A (ko) 세포자살 억제 화합물
JP3554399B2 (ja) ペプチド誘導体
Oiry et al. Synthesis and radioprotective activity of new N-(amino acid)-S-acetylcysteamine and cystamine derivatives
US20010007016A1 (en) Peptide derivatives
HU185978B (en) Process for preparing new tetrapeptide derivatives
JPH0656886A (ja) 新規なペプチド誘導体
JPWO1995024421A1 (ja) ペプチド誘導体
HK1128927A (en) Compounds for the inhibition of apoptosis
JPWO1997010261A1 (ja) ペプチド誘導体
JPH07252295A (ja) ６，７−ジヒドロキシ−４−チアヘプタン酸誘導体

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20091218

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20100730

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20110630

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20121128

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20130225

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20130509

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20130702

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: 20130805

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20130829

R150 Certificate of patent or registration of utility model

Ref document number: 5357022

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

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