JP2007537147A - メチオニンアミノペプチダーゼ−2のインヒビターおよびその使用 - Google Patents

メチオニンアミノペプチダーゼ−2のインヒビターおよびその使用 Download PDF

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Publication number
JP2007537147A
JP2007537147A JP2006547452A JP2006547452A JP2007537147A JP 2007537147 A JP2007537147 A JP 2007537147A JP 2006547452 A JP2006547452 A JP 2006547452A JP 2006547452 A JP2006547452 A JP 2006547452A JP 2007537147 A JP2007537147 A JP 2007537147A
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alkyl
substituted
compound
unsubstituted
group
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JP2007537147A5 (https=
Inventor
チャールズ トムプソン,
クリストファー シー. アリコ−ミュエンデル,
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Praecis Pharmaceuticals Inc
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Praecis Pharmaceuticals Inc
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D407/00Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/06Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06Esters of carbamic acids
    • C07C271/32Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C271/34Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/06Antipsoriatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/02Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • 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
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00Antiparasitic agents
    • A61P33/02Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00Antiparasitic agents
    • A61P33/02Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A61P33/06Antimalarials
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D303/00Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02Compounds containing oxirane rings
    • C07D303/12Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/14Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D303/00Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02Compounds containing oxirane rings
    • C07D303/12Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/16Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D303/00Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02Compounds containing oxirane rings
    • C07D303/12Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/22Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D407/00Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/08Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing alicyclic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14The ring being saturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (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)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Immunology (AREA)
  • Rheumatology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pain & Pain Management (AREA)
  • Cardiology (AREA)
  • Dermatology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Epoxy Compounds (AREA)
JP2006547452A 2003-12-29 2004-12-29 メチオニンアミノペプチダーゼ−2のインヒビターおよびその使用 Pending JP2007537147A (ja)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US53343103P 2003-12-29 2003-12-29
PCT/US2004/043586 WO2005066197A2 (en) 2003-12-29 2004-12-29 Inhibitors of methionine aminopeptidase-2 and uses thereof

Publications (2)

Publication Number Publication Date
JP2007537147A true JP2007537147A (ja) 2007-12-20
JP2007537147A5 JP2007537147A5 (https=) 2008-02-07

Family

ID=34748901

Family Applications (1)

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JP2006547452A Pending JP2007537147A (ja) 2003-12-29 2004-12-29 メチオニンアミノペプチダーゼ−2のインヒビターおよびその使用

Country Status (9)

Country Link
US (1) US20050239878A1 (https=)
EP (1) EP1699812A2 (https=)
JP (1) JP2007537147A (https=)
KR (1) KR20060130077A (https=)
CN (1) CN1902215A (https=)
AU (1) AU2004312512A1 (https=)
CA (1) CA2550873A1 (https=)
NO (1) NO20062812L (https=)
WO (1) WO2005066197A2 (https=)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2003230852B2 (en) * 2002-04-11 2008-07-10 Children's Medical Center Corporation TNP-470 polymer conjugates and use thereof
AU2003226349B2 (en) * 2002-04-11 2008-01-31 Children's Medical Center Corporation Methods for inhibiting vascular hyperpermeability
US20070254843A1 (en) * 2006-04-18 2007-11-01 Praecis Pharmaceuticals Incorporated Methods for treating bone associated diseases by the use of methionine aminopeptidase-2 inhibitors
WO2008066641A2 (en) * 2006-11-06 2008-06-05 Praecis Pharmaceuticals Incorporated Methods for treating mitf associated diseases by the use of methionine aminopeptidase-2 inhibitors
EP2170402B1 (en) * 2007-06-26 2015-03-25 Children's Medical Center Corporation Metap-2 inhibitor polymersomes for therapeutic administration
US8865746B2 (en) 2008-07-18 2014-10-21 Zafgen, Inc. Methods of treating an overweight or obese subject
US8642650B2 (en) 2008-12-04 2014-02-04 Zafgen, Inc. Methods of treating an overweight or obese subject
WO2013055385A2 (en) 2011-10-03 2013-04-18 Zafgen Corporation Methods of treating age related disorders
WO2010065877A2 (en) 2008-12-04 2010-06-10 Zafgen Corporation Methods of treating an overweight or obese subject
CA2777108A1 (en) 2009-10-09 2011-04-14 Zafgen Corporation Sulphone compounds and methods of making and using same
BR112012016793A2 (pt) 2010-01-08 2018-07-31 Zafgen Corp compostos tipo fumagilol e métodos de fazer e usar os mesmos
US8815309B2 (en) 2010-01-08 2014-08-26 Zafgen, Inc. Methods of treating a subject with benign prostate hyperplasia
WO2011088055A2 (en) 2010-01-12 2011-07-21 Zafgen Corporation Methods and compositions for treating cardiovascular disorders
WO2011127304A2 (en) 2010-04-07 2011-10-13 Zafgen Corporation Methods of treating an overweight subject
CN103249735B (zh) 2010-07-22 2016-04-06 扎夫根股份有限公司 三环化合物及其制备和使用方法
PH12013500934A1 (en) 2010-11-09 2022-10-24 Zafgen Inc Crystalline solids of a metap-2 inhibitor and methods of making and using same
WO2012064928A1 (en) 2010-11-10 2012-05-18 Zafgen Corporation Methods and compositions for treating thyroid hormone related disorders
WO2012074968A1 (en) 2010-11-29 2012-06-07 Zafgen Corporation Methods of reducing risk of hepatobiliary dysfunction during rapid weight loss with metap-2 inhibitors
US9173865B2 (en) 2010-11-29 2015-11-03 Zafgen, Inc. Treatment of obesity using non-daily administration of 6-O-(4-dimethylaminoethoxy) cinnamoyl fumagillol
US9189078B2 (en) 2010-12-20 2015-11-17 Apple Inc. Enhancing keycap legend visibility with optical components
MX344238B (es) 2011-01-26 2016-12-07 Zafgen Inc Compuestos de tetrazol y métodos para preparar y usar los mismos.
EP2683706B1 (en) 2011-03-08 2018-02-21 Zafgen, Inc. Oxaspiro [2.5]octane derivatives and analogs
EP2705036B1 (en) 2011-05-06 2015-08-12 Zafgen Inc. Tricyclic sulfonamide compounds and methods of making and using same
CN103764641B (zh) 2011-05-06 2016-10-26 扎夫根股份有限公司 部分饱和的三环化合物及其制备和使用方法
BR112013028666A2 (pt) 2011-05-06 2017-08-08 Zafgen Inc compostos de pirazolo sulfonamida tricícilos e métodos para fazer e usar o mesmo
MX2014008706A (es) 2012-01-18 2015-03-05 Zafgen Inc Compuestos tricíclicos de sulfonamida y métodos para elaborarlos y usarlos.
JP2015509102A (ja) 2012-01-18 2015-03-26 ザフゲン,インコーポレイテッド 三環式スルホン化合物並びにその作製および使用方法
BR112014027808A2 (pt) 2012-05-07 2017-06-27 Zafgen Inc sal polimórfico do sal de oxalato de 6-o-(4-dimetilaminoetoxi) cinaroil fumagilol e métodos de produção e utilização do mesmo
MX2014013599A (es) 2012-05-08 2015-05-11 Zafgen Inc Tratamiento de la obesidad hipotalamica con inhibidores de metap2.
BR112014027981A2 (pt) 2012-05-09 2017-06-27 Zafgen Inc compostos do tipo fumagilol e métodos de produção e utilização dos mesmos
MX2015005733A (es) 2012-11-05 2016-02-10 Zafgen Inc Compuestos triciclicos para usarse en el tratamiento y/o control de obesidad.
AU2013337282A1 (en) 2012-11-05 2015-05-21 Zafgen, Inc. Tricyclic compounds and methods of making and using same
NZ707773A (en) 2012-11-05 2019-05-31 Zafgen Inc Methods of treating liver diseases
CN105228610A (zh) 2013-03-14 2016-01-06 扎夫根股份有限公司 治疗肾疾病和其它病症的方法
CN106432255A (zh) 2015-08-11 2017-02-22 扎夫根公司 烟曲霉素醇螺环化合物和制备和使用其的方法
AR105671A1 (es) 2015-08-11 2017-10-25 Zafgen Inc Compuestos heterocíclicos de fumagillol y sus métodos de elaboración y uso
WO2018148638A1 (en) * 2017-02-10 2018-08-16 Zafgen, Inc. Pharmaceutical compositions of metap-2 inhibitors

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0415294A2 (en) * 1989-08-31 1991-03-06 Takeda Chemical Industries, Ltd. Cyclohexanol derivatives, production and use thereof
WO1998056372A1 (en) * 1997-06-09 1998-12-17 Massachusetts Institute Of Technology TYPE 2 METHIONINE AMINOPEPTIDASE (MetAP2) INHIBITORS AND USES THEROF
US20020193298A1 (en) * 2000-11-01 2002-12-19 Praecis Pharmaceuticals Inc. Therapeutic agents and methods of use thereof for the modulation of angiogenesis
WO2003092608A2 (en) * 2002-05-02 2003-11-13 Praecis Pharmaceuticals, Inc. Methionine aminopeptidase-2 inhibitors and methods of use thereof

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2546163B1 (fr) * 1983-05-16 1987-10-09 Centre Nat Rech Scient Nouveaux derives acyles hydrosolubles de peptides ou d'amino-acides, leur preparation et leur application
US5135919A (en) * 1988-01-19 1992-08-04 Children's Medical Center Corporation Method and a pharmaceutical composition for the inhibition of angiogenesis
PH26256A (en) * 1988-08-12 1992-04-01 Fujisawa Pharmaceutical Co Oxaspiro [2,5] octane derivative
KR0138530B1 (ko) * 1988-09-01 1998-05-15 우메모또 요시마사 푸마길롤 유도체
US5180738A (en) * 1988-09-01 1993-01-19 Takeda Chemical Industries Fumagillol derivatives and pharmaceutical compositions thereof
US6017954A (en) * 1989-08-10 2000-01-25 Children's Medical Center Corp. Method of treating tumors using O-substituted fumagillol derivatives
US5290807A (en) * 1989-08-10 1994-03-01 Children's Medical Center Corporation Method for regressing angiogenesis using o-substituted fumagillol derivatives
JPH06157344A (ja) * 1992-02-07 1994-06-03 Childrens Medical Center Corp:The 血管新生阻害のための医薬製剤及び血管新生阻害方法
EP0602586B1 (en) * 1992-12-16 1997-06-04 Takeda Chemical Industries, Ltd. Stable pharmaceutical composition of fumagillol derivatives
FR2733498B1 (fr) * 1995-04-27 1997-05-30 Adir Nouveaux composes cyclohexaniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0415294A2 (en) * 1989-08-31 1991-03-06 Takeda Chemical Industries, Ltd. Cyclohexanol derivatives, production and use thereof
WO1998056372A1 (en) * 1997-06-09 1998-12-17 Massachusetts Institute Of Technology TYPE 2 METHIONINE AMINOPEPTIDASE (MetAP2) INHIBITORS AND USES THEROF
US20020193298A1 (en) * 2000-11-01 2002-12-19 Praecis Pharmaceuticals Inc. Therapeutic agents and methods of use thereof for the modulation of angiogenesis
WO2003092608A2 (en) * 2002-05-02 2003-11-13 Praecis Pharmaceuticals, Inc. Methionine aminopeptidase-2 inhibitors and methods of use thereof

Also Published As

Publication number Publication date
EP1699812A2 (en) 2006-09-13
AU2004312512A1 (en) 2005-07-21
CN1902215A (zh) 2007-01-24
NO20062812L (no) 2006-07-21
CA2550873A1 (en) 2005-07-21
WO2005066197A2 (en) 2005-07-21
US20050239878A1 (en) 2005-10-27
KR20060130077A (ko) 2006-12-18
WO2005066197A3 (en) 2006-01-26

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