JP6290781B2 - ［（３−ヒドロキシピリジン−２−カルボニル）アミノ］アルカン酸、エステル及びアミドの製造方法 - Google Patents

［（３−ヒドロキシピリジン−２−カルボニル）アミノ］アルカン酸、エステル及びアミドの製造方法 Download PDF

Info

Publication number
JP6290781B2
JP6290781B2 JP2014514536A JP2014514536A JP6290781B2 JP 6290781 B2 JP6290781 B2 JP 6290781B2 JP 2014514536 A JP2014514536 A JP 2014514536A JP 2014514536 A JP2014514536 A JP 2014514536A JP 6290781 B2 JP6290781 B2 JP 6290781B2
Authority
JP
Japan
Prior art keywords
acid
heteroaryl
branched
aryl
linear
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
JP2014514536A
Other languages
English (en)
Japanese (ja)
Other versions
JP2014522409A (ja
Inventor
エム．ランシエル クリストファー
エム．ランシエル クリストファー
ゴリン ボリス
ゴリン ボリス
オウデネス ジャン
オウデネス ジャン
エドワード ディクソン クレイグ
エドワード ディクソン クレイグ
クイグボ ル アラン
クイグボ ル アラン
デンスモア コップ ジェームス
デンスモア コップ ジェームス
マイケル ジャヌスズ ジョン
マイケル ジャヌスズ ジョン
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Akebia Therapeutics Inc
Original Assignee
Akebia Therapeutics Inc
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 Akebia Therapeutics Inc filed Critical Akebia Therapeutics Inc
Publication of JP2014522409A publication Critical patent/JP2014522409A/ja
Application granted granted Critical
Publication of JP6290781B2 publication Critical patent/JP6290781B2/ja
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • 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
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/803—Processes of preparation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/824—Palladium

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Inorganic Chemistry (AREA)
  • Epidemiology (AREA)
  • Materials Engineering (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Ophthalmology & Optometry (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Curing Cements, Concrete, And Artificial Stone (AREA)
JP2014514536A 2011-06-06 2012-06-05 ［（３−ヒドロキシピリジン−２−カルボニル）アミノ］アルカン酸、エステル及びアミドの製造方法 Active JP6290781B2 (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201161493536P 2011-06-06 2011-06-06
US61/493,536 2011-06-06
PCT/US2012/040833 WO2012170377A1 (en) 2011-06-06 2012-06-05 Process for preparing [(3-hydroxypyridine-2-carbonyl)amino]alkanoic acids, esters and amides

Related Child Applications (1)

Application Number Title Priority Date Filing Date
JP2018020595A Division JP6510094B2 (ja) 2011-06-06 2018-02-08 ［（３−ヒドロキシピリジン−２−カルボニル）アミノ］アルカン酸、エステル及びアミドの製造方法

Publications (2)

Publication Number Publication Date
JP2014522409A JP2014522409A (ja) 2014-09-04
JP6290781B2 true JP6290781B2 (ja) 2018-03-07

Family

ID=47262177

Family Applications (6)

Application Number Title Priority Date Filing Date
JP2014514536A Active JP6290781B2 (ja) 2011-06-06 2012-06-05 ［（３−ヒドロキシピリジン−２−カルボニル）アミノ］アルカン酸、エステル及びアミドの製造方法
JP2018020595A Active JP6510094B2 (ja) 2011-06-06 2018-02-08 ［（３−ヒドロキシピリジン−２−カルボニル）アミノ］アルカン酸、エステル及びアミドの製造方法
JP2019070979A Active JP6816195B2 (ja) 2011-06-06 2019-04-03 ［（５−（ハロフェニル）−３−ヒドロキシピリジン−２−カルボニル）−アミノ］アルカン酸誘導体の調製における中間体としての５−（（ハロフェニル）−３−ハロ−ピリジン−２−イル）−ニトリル誘導体
JP2020213442A Active JP7039682B2 (ja) 2011-06-06 2020-12-23 ［（５－（ハロフェニル）－３－ヒドロキシピリジン－２－カルボニル）－アミノ］アルカン酸誘導体の調製における中間体としての５－（（ハロフェニル）－３－ハロ－ピリジン－２－イル）－ニトリル誘導体
JP2022035813A Active JP7284309B2 (ja) 2011-06-06 2022-03-09 ［（５－（ハロフェニル）－３－ヒドロキシピリジン－２－カルボニル）－アミノ］アルカン酸誘導体の調製における中間体としての５－（（ハロフェニル）－３－ハロ－ピリジン－２－イル）－ニトリル誘導体
JP2023081959A Active JP7685552B2 (ja) 2011-06-06 2023-05-18 ［（５－（ハロフェニル）－３－ヒドロキシピリジン－２－カルボニル）－アミノ］アルカン酸誘導体の調製における中間体としての５－（（ハロフェニル）－３－ハロ－ピリジン－２－イル）－ニトリル誘導体

Family Applications After (5)

Application Number Title Priority Date Filing Date
JP2018020595A Active JP6510094B2 (ja) 2011-06-06 2018-02-08 ［（３−ヒドロキシピリジン−２−カルボニル）アミノ］アルカン酸、エステル及びアミドの製造方法
JP2019070979A Active JP6816195B2 (ja) 2011-06-06 2019-04-03 ［（５−（ハロフェニル）−３−ヒドロキシピリジン−２−カルボニル）−アミノ］アルカン酸誘導体の調製における中間体としての５−（（ハロフェニル）−３−ハロ−ピリジン−２−イル）−ニトリル誘導体
JP2020213442A Active JP7039682B2 (ja) 2011-06-06 2020-12-23 ［（５－（ハロフェニル）－３－ヒドロキシピリジン－２－カルボニル）－アミノ］アルカン酸誘導体の調製における中間体としての５－（（ハロフェニル）－３－ハロ－ピリジン－２－イル）－ニトリル誘導体
JP2022035813A Active JP7284309B2 (ja) 2011-06-06 2022-03-09 ［（５－（ハロフェニル）－３－ヒドロキシピリジン－２－カルボニル）－アミノ］アルカン酸誘導体の調製における中間体としての５－（（ハロフェニル）－３－ハロ－ピリジン－２－イル）－ニトリル誘導体
JP2023081959A Active JP7685552B2 (ja) 2011-06-06 2023-05-18 ［（５－（ハロフェニル）－３－ヒドロキシピリジン－２－カルボニル）－アミノ］アルカン酸誘導体の調製における中間体としての５－（（ハロフェニル）－３－ハロ－ピリジン－２－イル）－ニトリル誘導体

Country Status (23)

Country Link
US (6) US9145366B2 (enExample)
EP (5) EP3290404B1 (enExample)
JP (6) JP6290781B2 (enExample)
KR (5) KR102293016B1 (enExample)
CN (1) CN106518759B (enExample)
AU (4) AU2012268426B2 (enExample)
CA (2) CA3135440A1 (enExample)
CY (4) CY1117177T1 (enExample)
DK (4) DK3683209T3 (enExample)
ES (4) ES2900572T3 (enExample)
HR (4) HRP20211916T1 (enExample)
HU (4) HUE034975T2 (enExample)
IL (1) IL229775A (enExample)
LT (3) LT3683209T (enExample)
MX (2) MX347709B (enExample)
NO (1) NO2686520T3 (enExample)
PL (4) PL3290404T3 (enExample)
PT (4) PT3290404T (enExample)
RS (3) RS56580B1 (enExample)
RU (2) RU2602083C2 (enExample)
SI (4) SI2718265T1 (enExample)
SM (3) SMT201700534T1 (enExample)
WO (1) WO2012170377A1 (enExample)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX2009000286A (es) 2006-06-26 2009-03-20 Procter & Gamble Inhibidores de prolil hidroxilasa y metodos de uso.
NO2686520T3 (enExample) 2011-06-06 2018-03-17
CN114404414A (zh) 2013-06-13 2022-04-29 阿克比治疗有限公司 用于治疗贫血症的组合物和方法
KR102495018B1 (ko) 2013-11-15 2023-02-06 아케비아 테라퓨틱스 인코포레이티드 ｛[5-(3-클로로페닐)-3-하이드록시피리딘-2-카보닐]아미노｝아세트산의 고체형, 이의 조성물 및 용도
WO2016034108A1 (zh) 2014-09-02 2016-03-10 广东东阳光药业有限公司 喹啉酮类化合物及其应用
EP3247355A4 (en) 2015-01-23 2018-06-13 Akebia Therapeutics, Inc. Solid forms of 2-(5-(3-fluorophenyl)-3-hydroxypicolinamido)acetic acid, compositions, and uses thereof
CA2979985A1 (en) * 2015-03-20 2016-09-29 Akebia Therapeutics, Inc. Deuterium-enriched hypoxia-inducible factor prolyl hydroxylase enzyme inhibitors
CN106146395B (zh) * 2015-03-27 2019-01-01 沈阳三生制药有限责任公司 3-羟基吡啶化合物、其制备方法及其制药用途
EA036920B1 (ru) 2015-04-01 2021-01-15 Экебиа Терапьютикс, Инк. Композиции и способы для лечения анемии
WO2018108101A1 (zh) * 2016-12-13 2018-06-21 苏州科睿思制药有限公司 {[5-(3-氯苯基)-3-羟基吡啶-2-羰基]氨基}乙酸的新晶型及其制备方法
IL269623B2 (en) * 2017-03-29 2025-05-01 Emerald Health Pharmaceuticals Inc Cannabidiol derivatives as inhibitors of the hif prolyl hydroxylases activity
WO2019028150A1 (en) 2017-08-01 2019-02-07 Akebia Therapeutics, Inc. COMPOSITIONS FOR USE IN METHODS OF TREATING HEMOGLOBINOPATHIES
TW202406895A (zh) * 2018-05-09 2024-02-16 美商阿克比治療有限公司 用於製備2-[[5-(3-氯苯基)-3-羥基吡啶-2-羰基]胺基]乙酸之方法
WO2020075199A1 (en) 2018-10-12 2020-04-16 Mylan Laboratories Limited Polymorphic forms of vadadustat
US11970450B2 (en) 2018-11-28 2024-04-30 Sandoz Ag Multi-component crystals of an orally available HIF prolyl hydroxylase inhibitor
WO2020217733A1 (ja) * 2019-04-26 2020-10-29 株式会社カネカ Ｖａｄａｄｕｓｔａｔ中間体の製造方法
US11524939B2 (en) 2019-11-13 2022-12-13 Akebia Therapeutics, Inc. Solid forms of {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino} acetic acid
CN111087343B (zh) * 2019-11-29 2022-02-18 万华化学集团股份有限公司 一种羟基吡啶配体及其制备方法和催化应用
JP7594546B2 (ja) * 2019-12-10 2024-12-04 田辺三菱製薬株式会社 含窒素ヘテロアリールカルボキサミド酢酸誘導体の製造方法
EP4094832A4 (en) 2020-01-24 2024-04-17 APS Japan Co., Ltd. Photocatalyst unit and mask provided with photocatalyst unit
WO2022006427A1 (en) 2020-07-02 2022-01-06 Akebia Therapeutics, Inc. Manufacturing process for 3,5-dichloropicolinonitrile for synthesis of vadadustat
GB202011431D0 (en) * 2020-07-23 2020-09-09 Johnson Matthey Plc Polymorphs of vadadustat and methods for preparing the polymorphs
EP4447963A1 (en) 2021-12-17 2024-10-23 Akebia Therapeutics Inc. Selective phd1 inhibitor compounds, compositions, and methods of use
WO2024165507A1 (en) 2023-02-06 2024-08-15 Institut National de la Santé et de la Recherche Médicale Use of hif-1α stabilizing agents for the treatment of type i interferonopathies

Family Cites Families (111)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3655679A (en) * 1969-06-25 1972-04-11 Merck & Co Inc Certain aryl pyridine carboxylic acid derivatives
US3703582A (en) * 1970-04-20 1972-11-21 Merck & Co Inc Aryl pyridine carboxylic acids in the treatment of inflammation
US3894920A (en) 1971-12-21 1975-07-15 Sagami Chem Res Process for preparing alkyl-substituted 3,6-dihydro-o-dioxin derivatives
US4016287A (en) 1972-07-17 1977-04-05 Boehringer Ingelheim Gmbh Dermatological compositions containing an acylamino-carboxylic acid or an alkyl ester thereof
TW219933B (enExample) 1990-02-26 1994-02-01 Lilly Co Eli
US5405613A (en) 1991-12-11 1995-04-11 Creative Nutrition Canada Corp. Vitamin/mineral composition
TW352384B (en) 1992-03-24 1999-02-11 Hoechst Ag Sulfonamido- or sulfonamidocarbonylpyridine-2-carboxamides, process for their preparation and their use as pharmaceuticals
DE4219158A1 (de) 1992-06-11 1993-12-16 Thomae Gmbh Dr K Biphenylderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
ES2101421T3 (es) 1993-11-02 1997-07-01 Hoechst Ag Amidas de acidos carboxilicos heterociclicos sustituidos, su preparacion y su utilizacion como medicamentos.
EP0650960B1 (de) 1993-11-02 1997-03-05 Hoechst Aktiengesellschaft Substituierte heterocyclische Carbonsäureamidester, ihre Herstellung und ihre Verwendung als Arzneimittel
TW406076B (en) 1993-12-30 2000-09-21 Hoechst Ag Substituted heterocyclic carboxamides, their preparation and their use as pharmaceuticals
DE4410423A1 (de) 1994-03-25 1995-09-28 Hoechst Ag Sulfonamidocarbonylpyridin-2-carbonsäureamide sowie ihre Pyridin-N-oxide, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
DE4410480A1 (de) 1994-03-25 1995-09-28 Hoechst Ag Sulfonamidocarbonylpyridin-2-carbonsäureesteramide sowie ihre Pyridin-N-oxide, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
US5789426A (en) 1995-01-20 1998-08-04 Cornell Research Foundation, Inc. Method for the treatment of fibroproliferative disorders by application of inhibitors of protein hydroxylation
IL135495A (en) 1995-09-28 2002-12-01 Hoechst Ag Intermediate compounds for the preparation of quinoline-converted amines - 2 - carboxylic acid
JPH09221476A (ja) 1995-12-15 1997-08-26 Otsuka Pharmaceut Co Ltd 医薬組成物
CA2253282A1 (en) 1996-04-30 1997-11-06 Hoechst Aktiengesellschaft 3-alkoxypyridine-2-carboxylic acid amide esters, their preparation and their use as drugs
DE19620041A1 (de) 1996-05-17 1998-01-29 Merck Patent Gmbh Adhäsionsrezeptor-Antagonisten
DE19650215A1 (de) 1996-12-04 1998-06-10 Hoechst Ag 3-Hydroxypyridin-2-carbonsäureamidester, ihre Herstellung und ihre Verwendung als Arzneimittel
US6420427B1 (en) 1997-10-09 2002-07-16 Ono Pharmaceutical Co., Ltd. Aminobutyric acid derivatives
DE19746287A1 (de) 1997-10-20 1999-04-22 Hoechst Marion Roussel De Gmbh Substituierte Isochinolin-2-Carbonsäureamide, ihre Herstellung und ihre Verwendung als Arzneimittel
ES2224620T3 (es) 1998-03-23 2005-03-01 Aventis Pharmaceuticals Inc. Derivados de piperidinilo y n-aminopiperidinilo.
US6159379A (en) 1999-05-04 2000-12-12 Baker Hughes Incorporated Organic ammonium salts for the removal of water soluble organics in produced water
JP2001048786A (ja) 1999-08-05 2001-02-20 Yamanouchi Pharmaceut Co Ltd 三環式ヘテロアリール誘導体
US6589758B1 (en) 2000-05-19 2003-07-08 Amgen Inc. Crystal of a kinase-ligand complex and methods of use
US6849718B2 (en) 2001-03-20 2005-02-01 Dana Farber Cancer Institute, Inc. Muteins of hypoxia inducible factor alpha and methods of use thereof
US6855510B2 (en) 2001-03-20 2005-02-15 Dana Farber Cancer Institute, Inc. Pharmaceuticals and methods for treating hypoxia and screening methods therefor
US20040146964A1 (en) 2001-03-21 2004-07-29 Maxwell Patrick Henry Assays, methods and means
SE0101327D0 (sv) 2001-04-12 2001-04-12 Astrazeneca Ab New crystalline forms
US6566088B1 (en) 2001-10-04 2003-05-20 Board Of Regents, The University Of Texas System Prolyl-4-hydroxylases
GB0124941D0 (en) 2001-10-17 2001-12-05 Glaxo Group Ltd Chemical compounds
CN102526044A (zh) 2001-12-06 2012-07-04 法布罗根股份有限公司 提高内源性红细胞生成素(epo)的方法
US8263637B2 (en) 2002-05-17 2012-09-11 Celgene Corporation Methods for treatment of multiple myeloma using cyclopropane carboxylic acid {2-[(is)-1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-3-oxo-2,3-dihydro-1 h-isoindol-4-yl}-amide
WO2004019868A2 (en) * 2002-08-29 2004-03-11 Merck & Co., Inc. N-biarylmethyl aminocycloalkanecarboxamide derivatives
CA2502541A1 (en) 2002-10-16 2004-04-29 Isis Innovation Limited Asparaginyl hydroxylases and modulators thereof
EP1567528A1 (en) 2002-11-21 2005-08-31 Eli Lilly And Company Mixed lineage kinase modulators
US7618940B2 (en) 2002-12-06 2009-11-17 Fibrogen, Inc. Fat regulation
US8124582B2 (en) 2002-12-06 2012-02-28 Fibrogen, Inc. Treatment of diabetes
US7183287B2 (en) 2003-04-03 2007-02-27 Pharmacia Corporation Substituted pyrimidinones
EP2357175A1 (en) 2003-06-06 2011-08-17 Fibrogen, Inc. isoquinoline derivatives AND THEIR USE IN INCREASING ENDOGENEOUS ERYTHROPOIETIN
WO2005007192A2 (en) 2003-06-06 2005-01-27 Fibrogen, Inc. Cytoprotection through the use of hif hydroxylase inhibitors
US8614204B2 (en) 2003-06-06 2013-12-24 Fibrogen, Inc. Enhanced erythropoiesis and iron metabolism
GB0314129D0 (en) 2003-06-18 2003-07-23 Astrazeneca Ab Therapeutic agents
WO2005108370A1 (ja) 2004-04-16 2005-11-17 Ajinomoto Co., Inc. ベンゼン化合物
NZ551632A (en) 2004-05-28 2009-09-25 Fibrogen Inc HIF prolyl hydroxylase activity assay
US20070185116A1 (en) 2004-05-31 2007-08-09 Tanabe Seiyaku Co., Ltd. Bicyclic compounds
JP2008506702A (ja) 2004-07-14 2008-03-06 ピーティーシー セラピューティクス，インコーポレーテッド Ｃ型肝炎を治療するための方法
TW200616969A (en) 2004-09-17 2006-06-01 Tanabe Seiyaku Co Imidazole compound
WO2006084210A2 (en) 2005-02-04 2006-08-10 Regents Of The University Of California, San Diego Hif modulating compounds and methods of use thereof
DE102005019712A1 (de) 2005-04-28 2006-11-09 Bayer Healthcare Ag Dipyridyl-dihydropyrazolone und ihre Verwendung
AU2006254897A1 (en) 2005-06-06 2006-12-14 Fibrogen, Inc. Improved treatment for anemia using a HIF-alpha stabilising agent
MX2007016160A (es) 2005-06-15 2008-03-07 Fibrogen Inc Uso de moduladoers de hif-1 alfa para el tratamiento contra el cancer.
WO2007033216A2 (en) 2005-09-12 2007-03-22 Beth Israel Deaconess Medical Center Methods and compositions for the treatment and diagnosis of diseases characterized by vascular leak, hypotension, or a procoagulant state
WO2007038571A2 (en) 2005-09-26 2007-04-05 Smithkline Beecham Corporation Prolyl hydroxylase antagonists
WO2007047194A2 (en) 2005-10-11 2007-04-26 Dana-Farber Cancer Institute, Inc. Methods for treating mitf-related disorders
US7728130B2 (en) 2005-12-09 2010-06-01 Amgen Inc. Quinolone based compounds exhibiting prolyl hydroxylase inhibitory activity
CA2635370A1 (en) 2006-01-09 2007-07-09 Btg International Limited Modulators of hypoxia inducible factor-1 and related uses
EP1983823A1 (en) 2006-01-17 2008-10-29 VIB vzw Inhibitors of prolyl-hydroxylase 1 for the treatment of skeletal muscle degeneration
JP4801451B2 (ja) 2006-01-19 2011-10-26 株式会社日立ハイテクノロジーズ 走査電子顕微鏡等に用いる電子銃の制御装置及び制御方法
US20070208053A1 (en) 2006-01-19 2007-09-06 Arnold Lee D Fused heterobicyclic kinase inhibitors
ITMI20060179A1 (it) 2006-02-02 2007-08-03 Abiogen Pharma Spa Procedimento per la risoluzione di miscele racemiche e complesso diastereoisomerico di un agente risolvente e di unantiomero di interesse
WO2007101204A1 (en) 2006-02-27 2007-09-07 Alcon Research, Ltd. Method of treating glaucoma
US7588924B2 (en) 2006-03-07 2009-09-15 Procter & Gamble Company Crystal of hypoxia inducible factor 1 alpha prolyl hydroxylase
TW200808793A (en) 2006-03-07 2008-02-16 Smithkline Beecham Corp Prolyl hydroxylase inhibitors
WO2007136990A2 (en) 2006-05-16 2007-11-29 Smithkline Beecham Corporation Prolyl hydroxylase inhibitors
AR061570A1 (es) 2006-06-23 2008-09-03 Smithkline Beecham Corp Compuesto de glicina sustituido en el n heteroaromatico composicion farmaceutica que lo comprende, su uso para preparar un medicamento, procedimientos para preparar dicha composicion farmaceutica y para preparar el compuesto
MX2009000286A (es) 2006-06-26 2009-03-20 Procter & Gamble Inhibidores de prolil hidroxilasa y metodos de uso.
TW200845991A (en) 2007-01-12 2008-12-01 Smithkline Beecham Corp N-substituted glycine derivatives: hydroxylase inhibitors
CL2008000065A1 (es) 2007-01-12 2008-09-22 Smithkline Beecham Corp Compuestos derivados de glicina n-sustituida, inhibidores de hif prolil hidroxilasas; su proceso de preparacion; composicion farmaceutica que comprende a dichos compuestos; y su uso en el tratamiento de la anemia.
CA2683758A1 (en) 2007-04-18 2008-10-30 Merck & Co., Inc. Novel 1,8-naphthyridine compounds
AU2008241577B2 (en) 2007-04-18 2011-04-07 Amgen Inc. Indanone derivatives that inhibit prolyl hydroxylase
AU2008248234B2 (en) 2007-05-04 2011-02-03 Amgen Inc. Thienopyridine and thiazolopyridine derivatives that inhibit prolyl hydroxylase activity
CA2685942A1 (en) 2007-05-16 2008-11-27 Merck & Co., Inc. Spiroindalones
AU2008253311A1 (en) 2007-05-18 2008-11-27 Bayer Schering Pharma Aktiengesellshaft Inhibitors of hypoxia inducible factor (HIF) useful for treating hyper-proliferative disorders and diseases associated with angiogenesis
ES2462416T3 (es) 2007-08-06 2014-05-22 Senju Pharmaceutical Co., Ltd. Producto farmacéutico que contiene un inhibidor de la expresión de HIF-1 alfa y HIF-2 alfa
TW200908984A (en) 2007-08-07 2009-03-01 Piramal Life Sciences Ltd Pyridyl derivatives, their preparation and use
EP2188295A4 (en) 2007-08-10 2011-11-16 Crystalgenomics Inc PYRIDINE DERIVATIVES AND METHODS OF USE
WO2009035534A2 (en) 2007-09-07 2009-03-19 The Cleveland Clinic Foundation Treatment of ischemic eye disease by the systematic pharmaceutical activation of hypoxia inducible factor (hif)
WO2009039323A1 (en) 2007-09-19 2009-03-26 Smithkline Beecham Corporation Prolyl hydroxylase inhibitors
WO2009039321A1 (en) 2007-09-19 2009-03-26 Smithkline Beecham Corporation Prolyl hydroxylase inhibitors
WO2009043093A1 (en) 2007-10-04 2009-04-09 Newsouth Innovations Pty Limited Hif inhibition
WO2009049112A1 (en) 2007-10-10 2009-04-16 Smithkline Beecham Corporation Prolyl hydroxylase inhibitors
WO2009067790A1 (en) 2007-11-26 2009-06-04 Uti Limited Partnership STIMULATION OF HYPOXIA INDUCIBLE FACTOR -1 ALPHA (HIF-1α) FOR THE TREATMENT OF CLOSTRIDIUM DIFFICILE ASSOCIATED DISEASE (CDAD), FOR INTESTINAL MOTILITY AND FOR DETECTING INFECTION
AU2008329746A1 (en) 2007-11-30 2009-06-04 Glaxosmithkline Llc Prolyl hydroxylase inhibitors
JP2011508725A (ja) 2007-11-30 2011-03-17 グラクソスミスクライン・リミテッド・ライアビリティ・カンパニー プロリルヒドロキシラーゼ阻害剤
EP2227475B1 (en) 2007-12-03 2014-02-19 Fibrogen, Inc. Isoxazolopyridine derivatives for use in the treatment of hif-mediated conditions
US20100298324A1 (en) 2007-12-19 2010-11-25 Smith Kline Beecham Corporation Prolyl Hydroxylase Inhibitors
US20110003013A1 (en) 2008-01-04 2011-01-06 Garvan Institute Of Medical Research Method of increasing metabolism
US8952160B2 (en) 2008-01-11 2015-02-10 Fibrogen, Inc. Isothiazole-pyridine derivatives as modulators of HIF (hypoxia inducible factor) activity
EA018068B1 (ru) * 2008-03-03 2013-05-30 Айрм Ллк Соединения и композиции в качестве модуляторов активности tlr
US20090228298A1 (en) * 2008-03-04 2009-09-10 The General Electric Company System and method of morphology feature analysis of physiological data
MX2010010241A (es) * 2008-03-20 2010-12-06 Forest Lab Holdings Ltd Derivados de piperidina novedosos como inhibidores de estearoil-coa desaturasa.
AR071997A1 (es) 2008-06-04 2010-07-28 Bristol Myers Squibb Co Forma cristalina de 6-((4s)-2-metil-4-(2-naftil)-1,2,3,4-tetrahidroisoquinolin-7-il)piridazin-3-amina
WO2010010017A1 (en) * 2008-07-23 2010-01-28 F. Hoffmann-La Roche Ag Heterocyclic antiviral compounds
WO2010029577A2 (en) 2008-09-15 2010-03-18 Ganga Raju Gokaraju Anti-cancer drugs and uses relating thereto for metastatic malignant melanoma and other cancers
CN102272117B (zh) 2008-11-14 2015-06-17 菲布罗根有限公司 作为hif羟化酶抑制剂的苯并噻喃衍生物
HRP20130846T1 (hr) * 2009-03-31 2013-11-22 Kissei Pharmaceutical Co., Ltd. Derivati indolizina i njihova uporaba u medicinske svrhe
MY160066A (en) 2009-11-06 2017-02-15 Aerpio Therapeutics Inc Methods for increasing the stabilization of hypoxia inducible factor-1 alpha
NO2686520T3 (enExample) 2011-06-06 2018-03-17
MX2013014310A (es) * 2011-06-06 2014-01-23 Akebia Therapeutics Inc Compuestos y composiciones para estabilizar el factor-2 alfa inducible por hipoxia como un metodo para tratar el cancer.
WO2012174256A2 (en) 2011-06-17 2012-12-20 The Regents Of The University Of Michigan Dna methylation profiles in cancer
CN104024227B8 (zh) 2011-07-22 2025-07-29 北京贝美拓新药研发有限公司 抑制脯氨酸羟化酶活性的化合物的晶型及其应用
CN105492011A (zh) 2013-04-08 2016-04-13 丹尼斯·M·布朗 不理想给药化学化合物的治疗增效
CN114404414A (zh) 2013-06-13 2022-04-29 阿克比治疗有限公司 用于治疗贫血症的组合物和方法
AU2014306496A1 (en) 2013-08-16 2016-03-03 Ohio State Innovation Foundation Compositions and methods for modulating DNA methylation
KR102495018B1 (ko) 2013-11-15 2023-02-06 아케비아 테라퓨틱스 인코포레이티드 ｛[5-(3-클로로페닐)-3-하이드록시피리딘-2-카보닐]아미노｝아세트산의 고체형, 이의 조성물 및 용도
WO2015112831A1 (en) 2014-01-23 2015-07-30 Akebia Therapeutics, Inc. Compositions and methods for treating ocular diseases
EP3247355A4 (en) 2015-01-23 2018-06-13 Akebia Therapeutics, Inc. Solid forms of 2-(5-(3-fluorophenyl)-3-hydroxypicolinamido)acetic acid, compositions, and uses thereof
CA2979985A1 (en) 2015-03-20 2016-09-29 Akebia Therapeutics, Inc. Deuterium-enriched hypoxia-inducible factor prolyl hydroxylase enzyme inhibitors
EA036920B1 (ru) 2015-04-01 2021-01-15 Экебиа Терапьютикс, Инк. Композиции и способы для лечения анемии
TW202406895A (zh) 2018-05-09 2024-02-16 美商阿克比治療有限公司 用於製備2-[[5-(3-氯苯基)-3-羥基吡啶-2-羰基]胺基]乙酸之方法

Also Published As

Publication number Publication date
KR20140037192A (ko) 2014-03-26
PL3000808T3 (pl) 2018-03-30
SMT201700534T1 (it) 2018-01-11
HRP20211916T1 (hr) 2022-03-18
KR20190032617A (ko) 2019-03-27
LT3683209T (lt) 2022-01-10
US9776969B2 (en) 2017-10-03
HUE048044T2 (hu) 2020-05-28
SI3683209T1 (sl) 2022-03-31
EP2718265A4 (en) 2014-11-19
NZ618570A (en) 2015-07-31
HUE034975T2 (en) 2018-05-02
JP7039682B2 (ja) 2022-03-22
JP7284309B2 (ja) 2023-05-30
KR102059366B1 (ko) 2019-12-26
PL3290404T3 (pl) 2020-06-01
JP7685552B2 (ja) 2025-05-29
AU2018250355A1 (en) 2018-11-08
PT2718265E (pt) 2016-02-15
DK3290404T3 (da) 2020-02-17
EP2718265A1 (en) 2014-04-16
HUE057571T2 (hu) 2022-05-28
HK1196616A1 (zh) 2014-12-19
US10246416B2 (en) 2019-04-02
KR20190141805A (ko) 2019-12-24
PT3683209T (pt) 2021-12-15
DK2718265T3 (en) 2016-01-25
KR102293016B1 (ko) 2021-08-26
CY1122639T1 (el) 2021-03-12
EP3290404B1 (en) 2019-12-11
SI2718265T1 (sl) 2016-03-31
KR20200121911A (ko) 2020-10-26
CY1124874T1 (el) 2022-11-25
SMT202000061T1 (it) 2020-03-13
MX2013014228A (es) 2014-03-26
PL2718265T3 (pl) 2016-04-29
HK1252109A1 (en) 2019-05-17
PT3290404T (pt) 2020-02-19
SMT201600013B (it) 2016-02-25
SI3290404T1 (sl) 2020-03-31
DK3683209T3 (da) 2021-12-06
RU2016139352A (ru) 2018-12-13
EP2718265B1 (en) 2015-12-16
RU2013158640A (ru) 2015-07-20
AU2018250355B2 (en) 2020-04-09
RU2016139352A3 (enExample) 2020-01-27
AU2017202414A1 (en) 2017-05-04
EP3290404A1 (en) 2018-03-07
CA2838194C (en) 2022-01-11
EP3683209A1 (en) 2020-07-22
EP4026829A1 (en) 2022-07-13
RS56580B1 (sr) 2018-02-28
DK3000808T3 (da) 2017-11-27
JP2022081597A (ja) 2022-05-31
NO2686520T3 (enExample) 2018-03-17
HRP20200197T1 (hr) 2020-05-15
HRP20171740T1 (hr) 2018-03-09
ES2647602T3 (es) 2017-12-22
AU2020204528B2 (en) 2022-07-14
CA2838194A1 (en) 2012-12-13
PT3000808T (pt) 2017-11-23
WO2012170377A1 (en) 2012-12-13
HUE026096T2 (en) 2016-05-30
JP6816195B2 (ja) 2021-01-20
KR20190031593A (ko) 2019-03-26
CN106518759B (zh) 2019-07-30
US20190375713A1 (en) 2019-12-12
MX347709B (es) 2017-05-10
RS54517B1 (sr) 2016-06-30
ES2559850T3 (es) 2016-02-16
ES2771232T3 (es) 2020-07-06
KR102032864B1 (ko) 2019-10-16
RU2602083C2 (ru) 2016-11-10
CY1117177T1 (el) 2017-04-05
EP3000808B1 (en) 2017-09-27
IL229775A (en) 2016-06-30
EP3683209B1 (en) 2021-11-10
JP2018111697A (ja) 2018-07-19
US20170362178A1 (en) 2017-12-21
HRP20151416T1 (hr) 2016-03-25
CA3135440A1 (en) 2012-12-13
RU2764667C2 (ru) 2022-01-19
US20230002323A1 (en) 2023-01-05
JP2023103414A (ja) 2023-07-26
AU2017202414B2 (en) 2018-07-19
US10738010B2 (en) 2020-08-11
MX337216B (es) 2016-02-18
JP2021059573A (ja) 2021-04-15
US11267785B2 (en) 2022-03-08
CN103717575A (zh) 2014-04-09
HK1216173A1 (en) 2016-10-21
ES2900572T3 (es) 2022-03-17
US20210122715A1 (en) 2021-04-29
AU2012268426B2 (en) 2017-02-16
KR102171315B1 (ko) 2020-10-28
JP2014522409A (ja) 2014-09-04
LT3000808T (lt) 2018-01-25
RS59902B1 (sr) 2020-03-31
US9145366B2 (en) 2015-09-29
EP3000808A1 (en) 2016-03-30
LT3290404T (lt) 2020-02-25
PL3683209T3 (pl) 2022-02-21
AU2012268426A1 (en) 2014-01-09
SI3000808T1 (en) 2018-02-28
KR102000485B1 (ko) 2019-07-16
US20120309977A1 (en) 2012-12-06
JP6510094B2 (ja) 2019-05-08
CY1119605T1 (el) 2018-04-04
CN106518759A (zh) 2017-03-22
JP2019123741A (ja) 2019-07-25
AU2020204528A1 (en) 2020-07-30
US20150361043A1 (en) 2015-12-17

Similar Documents

Publication Publication Date Title
JP6290781B2 (ja) ［（３−ヒドロキシピリジン−２−カルボニル）アミノ］アルカン酸、エステル及びアミドの製造方法
HK40078298A (en) Process for preparing n-[[5-(3-chlorophenyl)-3-hydroxy-2-pyridinyl]carbonyl]-glycine from 5-(3-chlorophenyl)-3-hydroxy-2-pyridine carboxylic acid
CN103717575B (zh) 用于制备[(3-羟基吡啶-2-羰基)氨基]链烷酸、酯和酰胺的方法
HK40033676B (en) Process for preparing [(5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl)-amino]acetic acid from 5-((3-chlorophenyl)-3-chloro-pyridin-2-yl)-nitrile, and process for preparing 5-((halophenyl)-3-halo-pyridin-2-yl)-nitrile derivatives
HK40033676A (en) Process for preparing [(5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl)-amino]acetic acid from 5-((3-chlorophenyl)-3-chloro-pyridin-2-yl)-nitrile, and process for preparing 5-((halophenyl)-3-halo-pyridin-2-yl)-nitrile derivatives
HK1252109B (en) 5-((halophenyl)-3-halo-pyridin-2-yl)-nitrile derivatives as intermediates in the preparation of [(5-(halophenyl)-3-hydroxypyridine-2-carbonyl)-amino]alkanoic acid derivatives
HK1216173B (en) 5-((halophenyl)-3-hydroxy-pyridin-2-yl)-carboxylic acid derivatives as intermediates for the preparation of carbonylamino alkanoic acids, esters and amides thereof
HK1196616B (en) Process for preparing [(3-hydroxypyridine-2-carbonyl)amino]alkanoic acids, esters and amides

Legal Events

Date Code Title Description
A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20150522

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20160128

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20160308

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20160603

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20160809

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20161213

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20170308

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20170502

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20170627

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20170922

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20171222

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: 20180109

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20180208

R150 Certificate of patent or registration of utility model

Ref document number: 6290781

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R153 Grant of patent term extension

Free format text: JAPANESE INTERMEDIATE CODE: R153

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