EA201070149A1 - Новые формы метилового эфира 2-циано-3,12-диоксоолеан-1,9(11)-диен-28-овой кислоты (cddo-me) - Google Patents

Новые формы метилового эфира 2-циано-3,12-диоксоолеан-1,9(11)-диен-28-овой кислоты (cddo-me)

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Publication number
EA201070149A1
EA201070149A1 EA201070149A EA201070149A EA201070149A1 EA 201070149 A1 EA201070149 A1 EA 201070149A1 EA 201070149 A EA201070149 A EA 201070149A EA 201070149 A EA201070149 A EA 201070149A EA 201070149 A1 EA201070149 A1 EA 201070149A1
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EA
Eurasian Patent Office
Prior art keywords
cddo
dioxoolean
cyano
acid methyl
dien
Prior art date
Application number
EA201070149A
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English (en)
Other versions
EA018704B1 (ru
Inventor
Джон Уоллинг
Стивен Д. Пэрент
Дэвид Т. Джонаитис
Роберт М. Крэл
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Реата Фармасьютикалз, Инк.
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Application filed by Реата Фармасьютикалз, Инк. filed Critical Реата Фармасьютикалз, Инк.
Publication of EA201070149A1 publication Critical patent/EA201070149A1/ru
Publication of EA018704B1 publication Critical patent/EA018704B1/ru

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/70Carbohydrates; Sugars; Derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • 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
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16Anti-Parkinson drugs
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/28Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13Crystalline forms, e.g. polymorphs
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J63/00Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C07J63/008Expansion of ring D by one atom, e.g. D homo steroids

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Molecular Biology (AREA)
  • Epidemiology (AREA)
  • Immunology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Psychiatry (AREA)
  • Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Glass Compositions (AREA)

Abstract

Тритерпеноидное соединение - метиловый эфир 2-циано-3,12-диоксоолеан-1,9(11)-диен-28-овой кислоты (CDDO-Me ) - находится в некристаллической твердой стекловидной форме и в безводной кристаллической форме, приготовляемых, например, из насыщенного раствора в метаноле. Стекловидная форма отличается улучшенной биодоступностью в сравнении с безводной кристаллической формой. Каждая форма CDDO-Me является превосходным кандидатом для применения обычно в твердой лекарственной форме при лечении различных заболеваний, как правило, связанных с воспалением.
EA201070149A 2007-08-15 2008-08-14 НОВЫЕ ФОРМЫ МЕТИЛОВОГО ЭФИРА 2-ЦИАНО-3,12-ДИОКСООЛЕАН-1,9(11)-ДИЕН-28-ОВОЙ КИСЛОТЫ (CDDO-Me) EA018704B1 (ru)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US95593907P 2007-08-15 2007-08-15
PCT/US2008/009703 WO2009023232A1 (en) 2007-08-15 2008-08-14 Novel forms of cddo methyl ester

Publications (2)

Publication Number Publication Date
EA201070149A1 true EA201070149A1 (ru) 2010-08-30
EA018704B1 EA018704B1 (ru) 2013-10-30

Family

ID=40351005

Family Applications (2)

Application Number Title Priority Date Filing Date
EA201370109A EA023550B1 (ru) 2007-08-15 2008-08-14 НОВЫЕ ФОРМЫ МЕТИЛОВОГО ЭФИРА 2-ЦИАНО-3,12-ДИОКСООЛЕАН-1,9(11)-ДИЕН-28-ОВОЙ КИСЛОТЫ (CDDO-Me)
EA201070149A EA018704B1 (ru) 2007-08-15 2008-08-14 НОВЫЕ ФОРМЫ МЕТИЛОВОГО ЭФИРА 2-ЦИАНО-3,12-ДИОКСООЛЕАН-1,9(11)-ДИЕН-28-ОВОЙ КИСЛОТЫ (CDDO-Me)

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EA201370109A EA023550B1 (ru) 2007-08-15 2008-08-14 НОВЫЕ ФОРМЫ МЕТИЛОВОГО ЭФИРА 2-ЦИАНО-3,12-ДИОКСООЛЕАН-1,9(11)-ДИЕН-28-ОВОЙ КИСЛОТЫ (CDDO-Me)

Country Status (29)

Country Link
US (3) US8088824B2 (ru)
EP (2) EP2450057B1 (ru)
JP (4) JP5005812B2 (ru)
KR (2) KR101544766B1 (ru)
CN (2) CN101820758B (ru)
AR (2) AR073155A1 (ru)
AT (1) ATE549035T1 (ru)
AU (1) AU2008287388B2 (ru)
BR (1) BRPI0815540A8 (ru)
CA (2) CA2696330C (ru)
CL (1) CL2008002417A1 (ru)
CY (2) CY1112864T1 (ru)
DK (2) DK2450057T3 (ru)
EA (2) EA023550B1 (ru)
ES (2) ES2382571T3 (ru)
HK (1) HK1143537A1 (ru)
HR (2) HRP20120350T1 (ru)
HU (1) HUE031866T2 (ru)
IL (2) IL203824A (ru)
LT (1) LT2450057T (ru)
MX (1) MX2010001628A (ru)
NZ (1) NZ583269A (ru)
PL (2) PL2187741T3 (ru)
PT (2) PT2187741E (ru)
SG (2) SG10201504650VA (ru)
SI (2) SI2450057T1 (ru)
TW (2) TWI419899B (ru)
WO (1) WO2009023232A1 (ru)
ZA (1) ZA201001066B (ru)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9155721B2 (en) 2009-02-13 2015-10-13 Reata Pharmaceuticals, Inc. Delayed release, oral dosage compositions that contain amorphous CDDO-Me

Families Citing this family (53)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6326507B1 (en) 1998-06-19 2001-12-04 Trustees Of Dartmouth College Therapeutic compounds and methods of use
US7435755B2 (en) 2000-11-28 2008-10-14 The Trustees Of Dartmouth College CDDO-compounds and combination therapies thereof
CA2472581C (en) 2002-01-15 2012-06-26 Trustees Of Dartmouth College Tricyclic-bis-enone derivatives and methods of use thereof
CA2670099A1 (en) 2006-11-17 2008-05-29 Trustees Of Dartmouth College Synthesis and biological activities of new tricyclic-bis-enones (tbes)
WO2008064132A2 (en) 2006-11-17 2008-05-29 Trustees Of Dartmouth College Synthetic triterpenoids and tricyclic-bis-enones for use in stimulating bone and cartilage growth
US8921340B2 (en) 2006-11-17 2014-12-30 Trustees Of Dartmouth College Methods for using synthetic triterpenoids in the treatment of bone or cartilage diseases or conditions
US8088824B2 (en) * 2007-08-15 2012-01-03 Reata Pharmaceuticals Inc. Forms of CDDO methyl ester
TW200942231A (en) * 2008-01-11 2009-10-16 Reata Pharmaceuticals Inc Synthetic triterpenoids and methods of use in the treatment of disease
TW201004627A (en) 2008-04-18 2010-02-01 Reata Pharmaceuticals Inc Antioxidant inflammation modulators: novel derivatives of oleanolic acid
CN104250280A (zh) 2008-04-18 2014-12-31 里亚塔医药公司 抗氧化剂炎症调节剂:c-17同系化齐墩果酸衍生物
JP5564490B2 (ja) 2008-04-18 2014-07-30 リアタ ファーマシューティカルズ インコーポレイテッド 抗炎症性ファルマコアを含む化合物および使用法
NZ588710A (en) 2008-04-18 2012-12-21 Reata Pharmaceuticals Inc Antioxidant inflammation modulators: oleanolic acid derivatives with amino and other modifications at C-17
WO2009129545A1 (en) 2008-04-18 2009-10-22 Reata Pharmaceuticals, Inc. Antioxidant inflammation modulators: oleanolic acid derivatives with saturation in the c-ring
JP5758801B2 (ja) 2008-07-22 2015-08-05 トラスティーズ・オブ・ダートマス・カレッジTrustees of Dartmouth College 単環式シアノエノンおよびその使用方法説明
EP2536285B1 (en) 2010-02-18 2018-04-25 vTv Therapeutics LLC Substituted fused imidazole derivatives, pharmaceutical compositions, and methods of use thereof
US8759535B2 (en) 2010-02-18 2014-06-24 High Point Pharmaceuticals, Llc Substituted fused imidazole derivatives, pharmaceutical compositions, and methods of use thereof
CA2795320C (en) 2010-04-12 2019-01-22 Reata Pharmaceuticals, Inc. Method of treating obesity using antioxidant inflammation modulators
NZ612788A (en) 2010-12-17 2015-10-30 Reata Pharmaceuticals Inc Pyrazolyl and pyrimidinyl tricyclic enones as antioxidant inflammation modulators
LT2683731T (lt) 2011-03-11 2019-07-10 Reata Pharmaceuticals, Inc. C4-monometiltriterpenoido dariniai ir jų panaudojimo būdai
CN103156861B (zh) * 2011-12-08 2015-11-25 陈丽梅 齐敦果酸衍生物及其可药用盐在治疗糖尿病眼病中的应用
RS61544B1 (sr) * 2012-04-27 2021-04-29 Reata Pharmaceuticals Inc Derivat 2,2-difluoropropionamida metil bardoksolona, njegove farmaceutske supstance i polimorfi za upotrebu za lečenje izvesnih stanja
US8981144B2 (en) 2012-05-08 2015-03-17 Trustees Of Dartmouth College Method for synthesizing 2-cyano-3,12-dioxoolean-1, 9(11)-dien-28-oic acid methyl ester and derivatives thereof
US8921419B2 (en) 2012-05-08 2014-12-30 Trustees Of Dartmouth College Triterpenoids and compositions containing the same
WO2013188818A1 (en) 2012-06-15 2013-12-19 Reata Pharmaceuticals, Inc. A-ring epoxidized triterpenoid-based anti-inflammation modulators and methods of use thereof
US9512094B2 (en) 2012-09-10 2016-12-06 Reata Pharmaceuticals, Inc. C17-heteroaryl derivatives of oleanolic acid and methods of use thereof
EP2892910B1 (en) * 2012-09-10 2016-09-07 AbbVie Inc. Glycyrrhetinic acid derivatives with anti-inflammatory activity
TWI630212B (zh) 2012-09-10 2018-07-21 瑞塔醫藥有限責任公司 丁香油素(oleanolic acid)之c17-烷二基與烯二基衍生物及其使用方法
WO2014040073A1 (en) 2012-09-10 2014-03-13 Reata Pharmaceuticals, Inc. C13-hydroxy derivatives of oleanolic acid and methods of use thereof
EP2739639A4 (en) 2012-09-28 2014-11-05 Applied Pharmaceutical Science Inc POLYMORPHS OF CDDO ETHYL ESTER AND USES THEREOF
CN102887936A (zh) * 2012-10-24 2013-01-23 苏州晶云药物科技有限公司 2-氰基-3,12-二氧代齐墩果-1,9(11)-二烯-28-酸甲酯晶型
CN102875634B (zh) * 2012-10-24 2014-08-20 苏州晶云药物科技有限公司 2-氰基-3,12-二氧代齐墩果-1,9(11)-二烯-28-酸甲酯的几种晶型
WO2014148455A1 (ja) 2013-03-19 2014-09-25 第一三共株式会社 テルペノイド誘導体
UY35534A (es) 2013-04-24 2014-10-31 Abbvie Inc Derivados de 2,2-difluoropropanamida y metil bardoxolona, formas polimórficas y métodos de uso
AU2014308600B2 (en) 2013-08-23 2020-03-05 Reata Pharmaceuticals Holdings, LLC Methods of treating and preventing endothelial dysfunction using bardoxolone methyl or analogs thereof
US9896475B2 (en) 2014-08-26 2018-02-20 Trustees Of Dartmouth College Pyridyl analogs of 1-(2-cyano-3,12-dioxooleana-1,9(11)dien-28-oyl) imidazole
US10189791B2 (en) 2014-08-26 2019-01-29 Trustees Of Dartmouth College Pyridyl analogs of 1-(2-cyano-3,12-dioxooleana-1,9(11)dien-28-oyl) imidazole
WO2016039359A1 (ja) 2014-09-10 2016-03-17 第一三共株式会社 眼疾患治療用及び予防用徐放性医薬組成物
WO2016089648A1 (en) 2014-12-01 2016-06-09 Vtv Therapeutics Llc Bach 1 inhibitors in combination with nrf2 activators and pharmaceutical compositions thereof
EP3233813B1 (en) 2014-12-19 2022-02-02 Geistlich Pharma AG Processes for preparing oxathiazin-like compounds
US11591302B2 (en) 2014-12-19 2023-02-28 Geistlich Pharm A Ag Processes for preparing oxathiazin-like compounds
WO2016130927A1 (en) 2015-02-12 2016-08-18 Reata Pharmaceuticals, Inc. Imidazolyl tricyclic enones as antioxidant iflammation modulators
KR102688052B1 (ko) 2015-07-02 2024-07-25 아세르타 파마. 비.브이. (S)-4-(8-아미노-3-(1-(부트-2-이노일)피롤리딘-2-일)이미다조[1,5-a]피라진-1-일)-N-(피리딘-2-일)벤즈아마이드의 고체 형태 및 제제
CN108290922B (zh) 2015-09-23 2021-12-07 里亚塔医药公司 用于抑制il-17和其它用途的c4-改性的齐墩果酸衍生物
EP3538104A1 (en) * 2016-11-08 2019-09-18 Reata Pharmaceuticals, Inc. Methods of treating alport syndrome using bardoxolone methyl or analogs thereof
TWI831738B (zh) 2016-12-16 2024-02-11 美商瑞塔醫藥有限責任公司 用於抑制RORγ及其他用途的嘧啶三環烯酮衍生物
US11427533B2 (en) 2017-07-13 2022-08-30 Pliva Hrvatska D.O.O. Crystalline polymorphs of bardoxolone methyl
ES2967689T3 (es) 2018-04-06 2024-05-03 Capsugel Belgium Nv Proceso de secado por aspersión para partículas de baja relación de aspecto que comprenden poli[(metacrilato de metilo)-co-(ácido metacrílico)]
WO2019241796A1 (en) 2018-06-15 2019-12-19 Reata Pharmaceuticals, Inc. Pyrazole and imidazole compounds for inhibition of il-17 and rorgamma
US12060340B2 (en) 2018-06-20 2024-08-13 Reata Pharmaceuticals, Inc Cysteine-dependent inverse agonists of nuclear receptors ROR-gamma/ROR-gamma-t and methods of treating diseases or disorders therewith
JPWO2020111089A1 (ja) 2018-11-27 2021-10-14 協和キリン株式会社 医薬組成物
JP2023526567A (ja) 2020-05-09 2023-06-21 リアタ ファーマシューティカルズ ホールディングス リミテッド ライアビリティ カンパニー バルドキソロンメチルまたはそのアナログを用いてcovid-19を処置する方法
US12059419B2 (en) 2020-10-16 2024-08-13 Idience Co., Ltd. Pharmaceutical composition comprising phthalazinone derivatives
EP4259155A1 (en) 2020-12-11 2023-10-18 Reata Pharmaceuticals Holdings, LLC Synthetic triterpenoids for use in therapy

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1317599C (en) * 1986-03-26 1993-05-11 Yukio Nezu 1,2,6-triphenyl-4(1h)-pyridinone derivatives, production and uses thereof
JPH01273020A (ja) * 1988-04-26 1989-10-31 Toray Ind Inc 有機非線形光学材料
US5064823A (en) * 1988-08-24 1991-11-12 Research Triangle Institute Pentacyclic triterpenoid compounds as topoisomerase inhibitors or cell differentiation inducers
JP2876144B2 (ja) * 1990-03-23 1999-03-31 東洋フアルマー株式会社 3―フェニルクマリン―7―イルオキシ酢酸誘導体とその製法及び用途
GB9622173D0 (en) * 1996-10-24 1996-12-18 Glaxo Group Ltd Particulate Products
US20050276836A1 (en) * 1997-06-11 2005-12-15 Michelle Wilson Coated vaginal devices for vaginal delivery of therapeutically effective and/or health-promoting agents
US6326507B1 (en) 1998-06-19 2001-12-04 Trustees Of Dartmouth College Therapeutic compounds and methods of use
US6890946B2 (en) * 1999-12-23 2005-05-10 Indiana University Research And Technology Corporation Use of parthenolide to inhibit cancer
AU2002243246A1 (en) * 2000-11-28 2002-06-24 Board Of Regents, The University Of Texas System Cddo-compounds and combination therapies thereof
US7435755B2 (en) * 2000-11-28 2008-10-14 The Trustees Of Dartmouth College CDDO-compounds and combination therapies thereof
US6974801B2 (en) * 2002-05-13 2005-12-13 The Trustees Of Dartmounth College Inhibitors and methods of use thereof
JP3618341B2 (ja) * 2003-04-15 2005-02-09 山之内製薬株式会社 臭化物及びその結晶
FR2861299B1 (fr) * 2003-10-28 2006-01-27 Pf Medicament Compositions pharmaceutiques a base de derives d'idasoxan sous formes polymorphes
US7652654B2 (en) 2003-12-08 2010-01-26 Sony Corporation Liquid crystal display and backlight adjusting method
US20060167097A1 (en) * 2004-04-16 2006-07-27 Cheppail Ramachandran Compositions and uses of Amooranin compounds
CA2609353C (en) * 2005-05-23 2015-04-28 Novartis Ag Crystalline and other forms of 4-amino-5-fluoro-3-[6-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]-1h-quinolin-2-one lactic acid salts
DE102005041613A1 (de) 2005-09-01 2007-03-08 Ergonex Pharma Gmbh Pharmazeutische Zusammensetzungen zur Behandlung von Karzinoid-Syndrom
WO2007069895A1 (en) 2005-12-12 2007-06-21 Mosamedix B.V. Annexin derivatives suitable for pretargeting in therapy and diagnosis
US8088824B2 (en) * 2007-08-15 2012-01-03 Reata Pharmaceuticals Inc. Forms of CDDO methyl ester

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9155721B2 (en) 2009-02-13 2015-10-13 Reata Pharmaceuticals, Inc. Delayed release, oral dosage compositions that contain amorphous CDDO-Me

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AU2008287388B2 (en) 2014-11-06
SG10201504650VA (en) 2015-07-30
KR20140024063A (ko) 2014-02-27
HK1143537A1 (en) 2011-01-07
EP2187741A4 (en) 2010-08-25
PT2187741E (pt) 2012-06-21
US8088824B2 (en) 2012-01-03
CN101820758B (zh) 2013-03-06
EP2187741A1 (en) 2010-05-26
IL251419A0 (en) 2017-05-29
HRP20161503T1 (hr) 2017-01-13
KR20100056488A (ko) 2010-05-27
US20120330050A1 (en) 2012-12-27
CY1112864T1 (el) 2016-04-13
EP2187741B1 (en) 2012-03-14
JP2010536754A (ja) 2010-12-02
CA2696330A1 (en) 2009-02-19
PL2187741T3 (pl) 2012-08-31
HRP20120350T1 (hr) 2012-05-31
TW200916476A (en) 2009-04-16
AU2008287388A1 (en) 2009-02-19
US8633243B2 (en) 2014-01-21
CN101820758A (zh) 2010-09-01
TWI486357B (zh) 2015-06-01
JP2015164939A (ja) 2015-09-17
CA2871864A1 (en) 2009-02-19
JP2018009001A (ja) 2018-01-18
DK2450057T3 (en) 2016-12-19
US8309601B2 (en) 2012-11-13
EP2450057A1 (en) 2012-05-09
CL2008002417A1 (es) 2009-03-27
JP5005812B2 (ja) 2012-08-22
EA018704B1 (ru) 2013-10-30
CN103254267A (zh) 2013-08-21
LT2450057T (lt) 2016-12-27
JP2012188438A (ja) 2012-10-04
CY1118329T1 (el) 2017-06-28
SG177905A1 (en) 2012-02-28
ES2602978T3 (es) 2017-02-23
NZ583269A (en) 2012-03-30
EP2450057B1 (en) 2016-09-28
CA2696330C (en) 2015-03-24
ZA201001066B (en) 2010-10-27
PT2450057T (pt) 2016-12-15
MX2010001628A (es) 2010-06-02
SI2450057T1 (sl) 2017-01-31
AR119704A2 (es) 2022-01-05
TW201402597A (zh) 2014-01-16
HUE031866T2 (en) 2017-08-28
WO2009023232A1 (en) 2009-02-19
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CN103254267B (zh) 2016-03-16
PL2450057T3 (pl) 2017-02-28
DK2187741T3 (da) 2012-04-16
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TWI419899B (zh) 2013-12-21
EA023550B1 (ru) 2016-06-30
US20090048204A1 (en) 2009-02-19
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IL203824A (en) 2017-04-30
BRPI0815540A2 (pt) 2014-09-30
CA2871864C (en) 2016-05-17
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BRPI0815540A8 (pt) 2023-04-11
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