CN104053647B - 作为hno供体的经羟胺取代的米氏酸、巴比妥酸和吡唑啉酮衍生物 - Google Patents
作为hno供体的经羟胺取代的米氏酸、巴比妥酸和吡唑啉酮衍生物 Download PDFInfo
- Publication number
- CN104053647B CN104053647B CN201280051009.4A CN201280051009A CN104053647B CN 104053647 B CN104053647 B CN 104053647B CN 201280051009 A CN201280051009 A CN 201280051009A CN 104053647 B CN104053647 B CN 104053647B
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- Prior art keywords
- alkyl
- compound
- disease
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- aryl
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- 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
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- 0 CC(*)CCC(C(C)=*(C)OC)(C(*(C)C(*1C)=*)=O)C1=O Chemical compound CC(*)CCC(C(C)=*(C)OC)(C(*(C)C(*1C)=*)=O)C1=O 0.000 description 2
Classifications
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D231/08—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with oxygen or sulfur atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
- C07D239/62—Barbituric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810435608.5A CN108409662B (zh) | 2011-10-17 | 2012-10-16 | 作为hno供体的经羟胺取代的米氏酸、巴比妥酸和吡唑啉酮衍生物 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161548036P | 2011-10-17 | 2011-10-17 | |
| US61/548,036 | 2011-10-17 | ||
| PCT/US2012/060425 WO2013059194A1 (en) | 2011-10-17 | 2012-10-16 | Meldrum 's acid, barbituric acid and pyrazolone derivatives substituted with hydroxylamine as hno donors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810435608.5A Division CN108409662B (zh) | 2011-10-17 | 2012-10-16 | 作为hno供体的经羟胺取代的米氏酸、巴比妥酸和吡唑啉酮衍生物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104053647A CN104053647A (zh) | 2014-09-17 |
| CN104053647B true CN104053647B (zh) | 2018-06-01 |
Family
ID=47143299
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810435608.5A Expired - Fee Related CN108409662B (zh) | 2011-10-17 | 2012-10-16 | 作为hno供体的经羟胺取代的米氏酸、巴比妥酸和吡唑啉酮衍生物 |
| CN201280051009.4A Expired - Fee Related CN104053647B (zh) | 2011-10-17 | 2012-10-16 | 作为hno供体的经羟胺取代的米氏酸、巴比妥酸和吡唑啉酮衍生物 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810435608.5A Expired - Fee Related CN108409662B (zh) | 2011-10-17 | 2012-10-16 | 作为hno供体的经羟胺取代的米氏酸、巴比妥酸和吡唑啉酮衍生物 |
Country Status (13)
| Country | Link |
|---|---|
| US (3) | US9181213B2 (enExample) |
| EP (1) | EP2776402B1 (enExample) |
| JP (1) | JP6177246B2 (enExample) |
| KR (1) | KR102061537B1 (enExample) |
| CN (2) | CN108409662B (enExample) |
| AU (2) | AU2013201929B2 (enExample) |
| BR (1) | BR112014009282B1 (enExample) |
| CA (1) | CA2852914C (enExample) |
| HK (1) | HK1200168A1 (enExample) |
| IL (1) | IL232101A (enExample) |
| MX (1) | MX363306B (enExample) |
| SG (1) | SG11201401587QA (enExample) |
| WO (1) | WO2013059194A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9181213B2 (en) | 2011-10-17 | 2015-11-10 | The Johns Hopkins University | Meldrum's acid, barbituric acid and pyrazolone derivatives substituted with hydroxylamine as HNO donors |
| BR112015017251B1 (pt) | 2013-01-18 | 2021-10-26 | Cardioxyl Pharmaceuticals, Inc. | Composições farmacêuticas compreendendo doadores de nitroxil, misturas e usos das referidas composições farmacêuticas |
| EP3126329B1 (en) | 2014-01-17 | 2019-05-29 | Cardioxyl Pharmaceuticals Inc. | N-hydroxymethanesulfonamide nitroxyl donors |
| ES2749682T3 (es) * | 2014-05-27 | 2020-03-23 | Cardioxyl Pharmaceuticals Inc | Derivados de pirazolona como donadores de nitroxilo |
| US9464061B2 (en) * | 2014-05-27 | 2016-10-11 | The Johns Hopkins University | N-hydroxylamino-barbituric acid derivatives |
| WO2015183838A1 (en) | 2014-05-27 | 2015-12-03 | The Johns Hopkins University | N-hydroxylamino-barbituric acid derivatives as nitroxyl donors |
| ES2871079T3 (es) | 2015-06-26 | 2021-10-28 | Univ Johns Hopkins | Acidos hidroxámicos N-sustituidos con grupos salientes a base de carbono como donantes eficaces de HNO y usos de los mismos |
| WO2017070084A1 (en) | 2015-10-19 | 2017-04-27 | Cardioxyl Pharmaceuticals, Inc. | N-hydroxylsulfonamide derivatives as nitroxyl donors |
| EP3365328A1 (en) * | 2015-10-19 | 2018-08-29 | Cardioxyl Pharmaceuticals, Inc. | Pyrazolone derivatives as nitroxyl donors |
| EP3490975B1 (en) * | 2016-07-28 | 2021-05-05 | The Johns Hopkins University | O-substituted hydroxamic acids |
| EP3565544A1 (en) | 2017-01-03 | 2019-11-13 | Cardioxyl Pharmaceuticals Inc. | Method of administering nitroxyl donating compounds |
| RS63124B1 (sr) | 2018-03-08 | 2022-05-31 | Incyte Corp | Aminopirazin diol jedinjenja kao pi3k-y inhibitori |
| US11046658B2 (en) | 2018-07-02 | 2021-06-29 | Incyte Corporation | Aminopyrazine derivatives as PI3K-γ inhibitors |
| US11912647B2 (en) | 2020-05-22 | 2024-02-27 | University Of Georgia Research Foundation, Inc. | Diversity-oriented synthesis of N,N,O-trisubstituted hydroxylamines from alcohols and amines by N—O bond formation |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040038947A1 (en) * | 2002-06-14 | 2004-02-26 | The Gov. Of The U.S. Of America As Represented By The Sec. Of The Dept. Of Health & Human Services | Method of treating ischemia/reperfusion injury with nitroxyl donors |
| CN101472576A (zh) * | 2006-03-17 | 2009-07-01 | 约翰斯·霍普金斯大学医学院 | 作为新的有生理学价值的硝酰氧基供体的n-羟基磺酰胺衍生物 |
| CN102076342A (zh) * | 2008-05-07 | 2011-05-25 | 卡尔迪奥克斯尔制药公司 | 作为硝酰基供体的新亚硝基化合物及其使用方法 |
| US20110136827A1 (en) * | 2009-12-07 | 2011-06-09 | Toscano John P | Bis-Acylated Hydroxylamine Derivatives |
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| US3751255A (en) | 1972-03-24 | 1973-08-07 | Eastman Kodak Co | Photosensitive and thermosensitive element, composition and process |
| JPS567710A (en) | 1979-06-28 | 1981-01-27 | Sansho Seiyaku Kk | Whitening cosmetic |
| US4539321A (en) | 1981-10-26 | 1985-09-03 | William H. Rorer, Inc. | 5-Diaza-aryl-3-substituted pyridone compounds |
| DE3583799D1 (de) | 1985-01-11 | 1991-09-19 | Abbott Lab Ltd | Feste zubereitung mit langsamer freisetzung. |
| US4663351A (en) | 1985-08-23 | 1987-05-05 | Berlex Laboratories, Inc. | Dobutamine tri-isobutyric acid ester and the use thereof as a cardiotonic agent |
| US4798824A (en) | 1985-10-03 | 1989-01-17 | Wisconsin Alumni Research Foundation | Perfusate for the preservation of organs |
| JP2773959B2 (ja) | 1990-07-10 | 1998-07-09 | 信越化学工業株式会社 | 大腸内放出性固形製剤 |
| US6525081B1 (en) | 1997-10-24 | 2003-02-25 | Shionogi & Co., Ltd. | Antirheumatic |
| UA73092C2 (uk) | 1998-07-17 | 2005-06-15 | Брістол-Майерс Сквібб Компані | Таблетка з ентеросолюбільним покриттям і спосіб її приготування |
| WO2000006128A1 (fr) | 1998-07-28 | 2000-02-10 | Tanabe Seiyaku Co., Ltd. | Preparation capable de liberer un medicament au niveau d'un site cible dans l'intestin |
| GB9918684D0 (en) | 1999-08-09 | 1999-10-13 | Novartis Ag | Organic compounds |
| GB0114223D0 (en) | 2001-06-12 | 2001-08-01 | Ici Plc | Catalytic oxidation process |
| US6936639B2 (en) | 2002-08-21 | 2005-08-30 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Nitroxyl progenitors in the treatment of heart failure |
| JP2007514759A (ja) | 2003-12-19 | 2007-06-07 | タケダ サン ディエゴ インコーポレイテッド | キナーゼ阻害剤 |
| EP1718621A4 (en) | 2004-01-30 | 2009-08-19 | Univ Johns Hopkins | NITROXYL PREPARATION COMPOUNDS APPLICATION METHOD |
| US8168771B2 (en) | 2005-01-31 | 2012-05-01 | The Johns Hopkins University | Use of consensus sequence as vaccine antigen to enhance recognition of virulent viral variants |
| CA2613477C (en) | 2005-06-23 | 2013-12-03 | Johns Hopkins University | Thiol-sensitive positive inotropes |
| EP2010476A4 (en) | 2006-04-13 | 2011-01-26 | Univ Wake Forest Health Sciences | NITROXYL DISPENSERS FROM C-NITROSO COMPOUNDS |
| JP2011502105A (ja) | 2007-09-26 | 2011-01-20 | ジョンズ ホプキンス ユニバーシティ | 新規で生理学的に有用なニトロキシル供与体としてのn−ヒドロキシルスルホンアミド誘導体 |
| WO2011063339A1 (en) | 2009-11-23 | 2011-05-26 | Cardioxyl Pharmaceuticals, Inc. | Nitroxyl donors for the treatment of pulmonary hypertension |
| CN102753520B (zh) | 2009-12-07 | 2016-06-08 | 约翰斯霍普金斯大学 | N-酰氧基磺酰胺和n-羟基-n-酰基磺酰胺衍生物 |
| US9181213B2 (en) | 2011-10-17 | 2015-11-10 | The Johns Hopkins University | Meldrum's acid, barbituric acid and pyrazolone derivatives substituted with hydroxylamine as HNO donors |
| BR112015017251B1 (pt) | 2013-01-18 | 2021-10-26 | Cardioxyl Pharmaceuticals, Inc. | Composições farmacêuticas compreendendo doadores de nitroxil, misturas e usos das referidas composições farmacêuticas |
| US9464061B2 (en) | 2014-05-27 | 2016-10-11 | The Johns Hopkins University | N-hydroxylamino-barbituric acid derivatives |
| ES2749682T3 (es) | 2014-05-27 | 2020-03-23 | Cardioxyl Pharmaceuticals Inc | Derivados de pirazolona como donadores de nitroxilo |
| WO2015183838A1 (en) | 2014-05-27 | 2015-12-03 | The Johns Hopkins University | N-hydroxylamino-barbituric acid derivatives as nitroxyl donors |
-
2012
- 2012-10-16 US US14/352,399 patent/US9181213B2/en active Active
- 2012-10-16 BR BR112014009282-6A patent/BR112014009282B1/pt not_active IP Right Cessation
- 2012-10-16 WO PCT/US2012/060425 patent/WO2013059194A1/en not_active Ceased
- 2012-10-16 CN CN201810435608.5A patent/CN108409662B/zh not_active Expired - Fee Related
- 2012-10-16 CN CN201280051009.4A patent/CN104053647B/zh not_active Expired - Fee Related
- 2012-10-16 AU AU2013201929A patent/AU2013201929B2/en not_active Ceased
- 2012-10-16 SG SG11201401587QA patent/SG11201401587QA/en unknown
- 2012-10-16 JP JP2014537151A patent/JP6177246B2/ja not_active Expired - Fee Related
- 2012-10-16 KR KR1020147013269A patent/KR102061537B1/ko not_active Expired - Fee Related
- 2012-10-16 CA CA2852914A patent/CA2852914C/en active Active
- 2012-10-16 EP EP12781538.9A patent/EP2776402B1/en active Active
- 2012-10-16 HK HK15100597.0A patent/HK1200168A1/xx unknown
- 2012-10-16 MX MX2014004596A patent/MX363306B/es unknown
-
2014
- 2014-04-13 IL IL232101A patent/IL232101A/en active IP Right Grant
-
2015
- 2015-10-21 AU AU2015246114A patent/AU2015246114A1/en not_active Abandoned
- 2015-10-29 US US14/927,039 patent/US9499511B2/en active Active
-
2016
- 2016-10-11 US US15/290,872 patent/US9862699B2/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040038947A1 (en) * | 2002-06-14 | 2004-02-26 | The Gov. Of The U.S. Of America As Represented By The Sec. Of The Dept. Of Health & Human Services | Method of treating ischemia/reperfusion injury with nitroxyl donors |
| CN101472576A (zh) * | 2006-03-17 | 2009-07-01 | 约翰斯·霍普金斯大学医学院 | 作为新的有生理学价值的硝酰氧基供体的n-羟基磺酰胺衍生物 |
| CN102076342A (zh) * | 2008-05-07 | 2011-05-25 | 卡尔迪奥克斯尔制药公司 | 作为硝酰基供体的新亚硝基化合物及其使用方法 |
| US20110136827A1 (en) * | 2009-12-07 | 2011-06-09 | Toscano John P | Bis-Acylated Hydroxylamine Derivatives |
Non-Patent Citations (2)
| Title |
|---|
| Development of N-Substituted Hydroxylamines as Efficient Nitroxyl (HNO) Donors;Daryl A. Guthrie等;《Journal of American Chemistry Society》;20120201;第134卷(第4期);第1962-1965页 * |
| Production of nitroxyl(HNO) at biologically relevant temperatures from the retro-Diels-Alder reaction of N-hydroxyurea-derived acyl nitroso-9,10-dimethylanthracene cycloadducts;Yueping Xu等;《Tetrahedron Letters》;20000608;第41卷(第22期);第4265-4269页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2013059194A1 (en) | 2013-04-25 |
| US20160115148A1 (en) | 2016-04-28 |
| BR112014009282B1 (pt) | 2021-12-14 |
| US9862699B2 (en) | 2018-01-09 |
| SG11201401587QA (en) | 2014-07-30 |
| CA2852914C (en) | 2019-11-26 |
| US20170050947A1 (en) | 2017-02-23 |
| EP2776402A1 (en) | 2014-09-17 |
| MX363306B (es) | 2019-03-20 |
| HK1200168A1 (en) | 2015-07-31 |
| JP2015501308A (ja) | 2015-01-15 |
| EP2776402B1 (en) | 2017-07-26 |
| BR112014009282A8 (pt) | 2020-04-22 |
| AU2013201929A1 (en) | 2013-05-02 |
| AU2015246114A1 (en) | 2015-11-12 |
| MX2014004596A (es) | 2014-09-04 |
| CA2852914A1 (en) | 2013-04-25 |
| AU2013201929B2 (en) | 2015-07-23 |
| US9499511B2 (en) | 2016-11-22 |
| JP6177246B2 (ja) | 2017-08-09 |
| KR20140107197A (ko) | 2014-09-04 |
| CN108409662A (zh) | 2018-08-17 |
| IL232101A (en) | 2017-04-30 |
| KR102061537B1 (ko) | 2020-01-03 |
| CN108409662B (zh) | 2021-10-26 |
| BR112014009282A2 (pt) | 2017-06-13 |
| US9181213B2 (en) | 2015-11-10 |
| US20140275134A1 (en) | 2014-09-18 |
| CN104053647A (zh) | 2014-09-17 |
| IL232101A0 (en) | 2014-05-28 |
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