ZA201507750B - Quinazolines and azaquinazolines as dual inhibitors of ras/raf/mek/erk and pi3k/akt/pten/mtor pathways - Google Patents
Quinazolines and azaquinazolines as dual inhibitors of ras/raf/mek/erk and pi3k/akt/pten/mtor pathwaysInfo
- Publication number
- ZA201507750B ZA201507750B ZA2015/07750A ZA201507750A ZA201507750B ZA 201507750 B ZA201507750 B ZA 201507750B ZA 2015/07750 A ZA2015/07750 A ZA 2015/07750A ZA 201507750 A ZA201507750 A ZA 201507750A ZA 201507750 B ZA201507750 B ZA 201507750B
- Authority
- ZA
- South Africa
- Prior art keywords
- azaquinazolines
- quinazolines
- pten
- erk
- pi3k
- Prior art date
Links
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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/5005—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells
- G01N33/5008—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics
- G01N33/5011—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics for testing antineoplastic activity
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/575—Immunoassay; Biospecific binding assay; Materials therefor for cancer
- G01N33/5758—Immunoassay; Biospecific binding assay; Materials therefor for cancer involving compounds serving as markers for tumours, cancers or neoplasias, e.g. cellular determinants, receptors, heat shock/stress proteins, A-protein, oligosaccharides or metabolites
- G01N33/57595—Immunoassay; Biospecific binding assay; Materials therefor for cancer involving compounds serving as markers for tumours, cancers or neoplasias, e.g. cellular determinants, receptors, heat shock/stress proteins, A-protein, oligosaccharides or metabolites involving intracellular compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cell Biology (AREA)
- General Physics & Mathematics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- Food Science & Technology (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Pathology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Toxicology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Dermatology (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361811408P | 2013-04-12 | 2013-04-12 | |
| PCT/US2014/033727 WO2014169167A1 (en) | 2013-04-12 | 2014-04-11 | Quinazolines and azaquinazolines as dual inhibitors of ras/raf/mek/erk and pi3k/akt/pten/mtor pathways |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA201507750B true ZA201507750B (en) | 2017-08-30 |
Family
ID=50771612
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA2015/07750A ZA201507750B (en) | 2013-04-12 | 2015-10-16 | Quinazolines and azaquinazolines as dual inhibitors of ras/raf/mek/erk and pi3k/akt/pten/mtor pathways |
Country Status (13)
| Country | Link |
|---|---|
| US (5) | US9499495B2 (enExample) |
| EP (1) | EP2984088B1 (enExample) |
| JP (1) | JP6496301B2 (enExample) |
| KR (1) | KR20150143672A (enExample) |
| CN (1) | CN105283454B (enExample) |
| AU (1) | AU2014250836C1 (enExample) |
| BR (1) | BR112015025901A8 (enExample) |
| CA (1) | CA2909310A1 (enExample) |
| IL (2) | IL242020B (enExample) |
| MX (1) | MX2015014387A (enExample) |
| RU (1) | RU2015148359A (enExample) |
| WO (1) | WO2014169167A1 (enExample) |
| ZA (1) | ZA201507750B (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017112777A1 (en) | 2015-12-22 | 2017-06-29 | SHY Therapeutics LLC | Compounds for the treatment of cancer and inflammatory disease |
| JP2019519593A (ja) * | 2016-07-06 | 2019-07-11 | ザ・リージェンツ・オブ・ザ・ユニバーシティ・オブ・ミシガンＴｈｅ Ｒｅｇｅｎｔｓ Ｏｆ Ｔｈｅ Ｕｎｉｖｅｒｓｉｔｙ Ｏｆ Ｍｉｃｈｉｇａｎ | ＭＥＫ／ＰＩ３Ｋ及びｍＴＯＲ／ＭＥＫ／ＰＩ３Ｋ生物学的経路の多官能性阻害剤、並びに同多官能性阻害剤を用いた治療方法 |
| EP4169918B8 (en) | 2016-12-26 | 2025-09-24 | Institute of Materia Medica, Chinese Academy of Medical Sciences | Quinazoline derivatives as inhibitors of pi3k for the treatment of cancer |
| CN108239076B (zh) * | 2016-12-26 | 2021-07-06 | 中国医学科学院药物研究所 | 喹唑啉类化合物及其制备方法、用途和药物组合物 |
| CN108239074B (zh) * | 2016-12-26 | 2021-07-06 | 中国医学科学院药物研究所 | 喹唑啉类化合物及其制备方法、用途和药物组合物 |
| CN108239075B (zh) * | 2016-12-26 | 2021-07-02 | 中国医学科学院药物研究所 | 喹唑啉类化合物及其制备方法、用途和药物组合物 |
| US11318137B2 (en) | 2017-05-17 | 2022-05-03 | Vanderbilt University | Quinazoline compounds as modulators of Ras signaling |
| KR102736865B1 (ko) * | 2017-06-21 | 2024-12-03 | 샤이 테라퓨틱스 엘엘씨 | 암, 염증성 질환, 신경발달질환 및 섬유증 질환의 치료를 위하여 Ras 수퍼패밀리와 상호작용하는 화합물 |
| US10695296B2 (en) * | 2017-07-14 | 2020-06-30 | Asana Biosciences, Llc | Formulations, methods, kit, and dosage forms for improved stability of an active pharmaceutical ingredient |
| CN108623582A (zh) * | 2017-10-10 | 2018-10-09 | 河南省锐达医药科技有限公司 | 一类新型含取代基吡啶并嘧啶化合物的制备方法 |
| MX2020011991A (es) | 2018-05-10 | 2021-04-12 | Univ Louisville Res Found Inc | Inhibidores de la oncoproteina ras, metodos de produccion y metodos de uso de los mismos. |
| JP7407461B2 (ja) | 2018-12-19 | 2024-01-04 | シャイ・セラピューティクス・エルエルシー | がん、炎症性疾患、ｒａｓ病、及び線維性疾患の処置のためのｒａｓスーパーファミリーと相互作用する化合物 |
| CN111499634B (zh) * | 2019-01-31 | 2023-05-12 | 贝达药业股份有限公司 | 一种喹唑啉化合物及其在医药上的应用 |
| CN112341434B (zh) * | 2019-08-08 | 2021-11-26 | 恩瑞生物医药科技（上海）有限公司 | PI3K/mTOR蛋白降解靶向嵌合体类化合物及其制备方法和医药用途 |
| MX2022005229A (es) | 2019-11-01 | 2022-06-08 | Fmc Corp | Un nuevo proceso eficaz para la sintesis de 2-amino-5-cloro-n,3-di metilbenzamida. |
| MX2022005359A (es) | 2019-11-04 | 2022-06-02 | Revolution Medicines Inc | Inhibidores de ras. |
| IL301298A (en) | 2020-09-15 | 2023-05-01 | Revolution Medicines Inc | Indole derivatives as RAS inhibitors in cancer therapy |
| PE20231311A1 (es) * | 2020-11-18 | 2023-08-24 | Deciphera Pharmaceuticals Llc | Inhibidores de gcn2 y perk quinasas y metodos de uso de los mismos |
| IL308195A (en) | 2021-05-05 | 2024-01-01 | Revolution Medicines Inc | RAS inhibitors for cancer treatment |
| CN113416181B (zh) * | 2021-08-02 | 2022-05-03 | 四川大学 | 喹唑啉类衍生物及其用途 |
| IL310931A (en) * | 2021-09-10 | 2024-04-01 | Black Diamond Therapeutics Inc | 6-aza-quinoline derivatives and related uses |
| AR127308A1 (es) | 2021-10-08 | 2024-01-10 | Revolution Medicines Inc | Inhibidores ras |
| US20250084078A1 (en) * | 2022-01-04 | 2025-03-13 | Genfleft Therapeutics (Shanghai) Inc. | Fused ring-substituted six-membered heterocyclic compound, and preparation method therefor and use thereof |
| CN115894211A (zh) * | 2022-11-10 | 2023-04-04 | 山东龙立恒医药有限公司 | 一种3-羟基-4-甲基苯甲酸的制备方法 |
| GB202415232D0 (en) | 2024-10-16 | 2024-11-27 | Nacamed As | Composition |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0428475D0 (en) | 2004-12-30 | 2005-02-02 | 4 Aza Bioscience Nv | Pyrido(3,2-D)pyrimidine derivatives and pharmaceutical compositions useful as medicines for the treatment of autoimmune disorders |
| GB0503506D0 (en) | 2005-02-21 | 2005-03-30 | 4 Aza Bioscience Nv | Substituted pyrido(2,3-d) pyrimidine derivatives and pharmaceutical compositions useful as medicines for the treatment of autoimmune disorders |
| AU2007243466B2 (en) | 2006-04-26 | 2012-01-19 | F. Hoffmann-La Roche Ag | Phosphoinositide 3-kinase inhibitor compounds and pharmaceutical compositions containing them |
| UY31137A1 (es) * | 2007-06-14 | 2009-01-05 | Smithkline Beecham Corp | Derivados de quinazolina como inhibidores de la pi3 quinasa |
| JP2010539239A (ja) * | 2007-09-17 | 2010-12-16 | 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 | Ｐｉ３キナーゼ阻害剤としてのピリドピリミジン誘導体 |
| ES2553390T3 (es) | 2008-02-25 | 2015-12-09 | Nestec S.A. | Método para la detección de receptores truncados intracelulares |
| WO2010037765A2 (en) * | 2008-10-03 | 2010-04-08 | Merck Serono S.A. | 4-morpholino-pyrido[3,2-d]pyrimidines |
| WO2011097526A1 (en) * | 2010-02-05 | 2011-08-11 | Irm Llc | Compounds and compositions as protein kinase inhibitors |
| MX2012009059A (es) | 2010-02-22 | 2012-09-07 | Hoffmann La Roche | Compuestos inhibidores de fosfoinositida 3-cinasa delta (pi3k) pirido [3,2-d]pirimidina y metodos de uso. |
| WO2012118492A1 (en) * | 2011-03-01 | 2012-09-07 | Array Biopharma Inc. | Heterocyclic sulfonamides as raf inhibitors |
-
2014
- 2014-04-11 CN CN201480033247.1A patent/CN105283454B/zh not_active Expired - Fee Related
- 2014-04-11 MX MX2015014387A patent/MX2015014387A/es unknown
- 2014-04-11 JP JP2016507671A patent/JP6496301B2/ja not_active Expired - Fee Related
- 2014-04-11 EP EP14725852.9A patent/EP2984088B1/en not_active Not-in-force
- 2014-04-11 KR KR1020157032374A patent/KR20150143672A/ko not_active Abandoned
- 2014-04-11 RU RU2015148359A patent/RU2015148359A/ru not_active Application Discontinuation
- 2014-04-11 US US14/783,903 patent/US9499495B2/en not_active Expired - Fee Related
- 2014-04-11 AU AU2014250836A patent/AU2014250836C1/en not_active Ceased
- 2014-04-11 BR BR112015025901A patent/BR112015025901A8/pt not_active Application Discontinuation
- 2014-04-11 CA CA2909310A patent/CA2909310A1/en not_active Abandoned
- 2014-04-11 WO PCT/US2014/033727 patent/WO2014169167A1/en not_active Ceased
-
2015
- 2015-10-11 IL IL242020A patent/IL242020B/en not_active IP Right Cessation
- 2015-10-16 ZA ZA2015/07750A patent/ZA201507750B/en unknown
-
2016
- 2016-10-11 US US15/290,788 patent/US9757382B2/en not_active Expired - Fee Related
-
2017
- 2017-04-28 US US15/581,330 patent/US10226468B2/en not_active Expired - Fee Related
-
2018
- 2018-10-11 IL IL262314A patent/IL262314A/en unknown
-
2019
- 2019-01-24 US US16/256,365 patent/US10912779B2/en not_active Expired - Fee Related
-
2020
- 2020-11-05 US US17/090,513 patent/US20210113578A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| KR20150143672A (ko) | 2015-12-23 |
| WO2014169167A1 (en) | 2014-10-16 |
| EP2984088B1 (en) | 2019-03-20 |
| IL262314A (en) | 2018-11-29 |
| AU2014250836B2 (en) | 2018-07-12 |
| CN105283454A (zh) | 2016-01-27 |
| JP2016519685A (ja) | 2016-07-07 |
| US10226468B2 (en) | 2019-03-12 |
| MX2015014387A (es) | 2017-04-10 |
| HK1215810A1 (en) | 2016-09-15 |
| US10912779B2 (en) | 2021-02-09 |
| AU2014250836C1 (en) | 2019-01-17 |
| CA2909310A1 (en) | 2014-10-16 |
| RU2015148359A (ru) | 2017-05-15 |
| US9499495B2 (en) | 2016-11-22 |
| US20190151327A1 (en) | 2019-05-23 |
| BR112015025901A8 (pt) | 2020-01-14 |
| US9757382B2 (en) | 2017-09-12 |
| IL242020B (en) | 2019-08-29 |
| US20160068496A1 (en) | 2016-03-10 |
| US20170290838A1 (en) | 2017-10-12 |
| JP6496301B2 (ja) | 2019-04-03 |
| EP2984088A1 (en) | 2016-02-17 |
| CN105283454B (zh) | 2019-10-29 |
| US20170027953A1 (en) | 2017-02-02 |
| US20210113578A1 (en) | 2021-04-22 |
| BR112015025901A2 (pt) | 2017-07-25 |
| AU2014250836A1 (en) | 2015-11-26 |
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