JP6059342B2 - ｃ−ＭＥＴチロシンキナーゼ阻害剤として有用な新規な縮合ピリジン誘導体 - Google Patents
ｃ−ＭＥＴチロシンキナーゼ阻害剤として有用な新規な縮合ピリジン誘導体 Download PDFInfo
- Publication number
- JP6059342B2 JP6059342B2 JP2015518816A JP2015518816A JP6059342B2 JP 6059342 B2 JP6059342 B2 JP 6059342B2 JP 2015518816 A JP2015518816 A JP 2015518816A JP 2015518816 A JP2015518816 A JP 2015518816A JP 6059342 B2 JP6059342 B2 JP 6059342B2
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- fluoro
- dihydro
- yloxy
- substituted
- 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.)
- Expired - Fee Related
Links
- 0 C*NC(N1*)=NC=C(C)C1=O Chemical compound C*NC(N1*)=NC=C(C)C1=O 0.000 description 4
- OAGRDBWHMDVOQR-UHFFFAOYSA-N Nc(cc1)cc(F)c1Oc1ccnc2c1CCN2 Chemical compound Nc(cc1)cc(F)c1Oc1ccnc2c1CCN2 OAGRDBWHMDVOQR-UHFFFAOYSA-N 0.000 description 1
- QMNDOMWPEWZEJN-UHFFFAOYSA-N Nc(cc1)cc(F)c1Oc1ccnc2c1OCCN2 Chemical compound Nc(cc1)cc(F)c1Oc1ccnc2c1OCCN2 QMNDOMWPEWZEJN-UHFFFAOYSA-N 0.000 description 1
- DNXINZHZZFEIAH-UHFFFAOYSA-N Nc(cc1)ccc1Oc1c2OCCNc2ncc1 Chemical compound Nc(cc1)ccc1Oc1c2OCCNc2ncc1 DNXINZHZZFEIAH-UHFFFAOYSA-N 0.000 description 1
- KZLUVOZMCBNEOV-UHFFFAOYSA-N O=C(C1=CC=CN(c(cc2)ccc2F)C1=O)Nc(cc1)cc(F)c1Oc1ccnc2c1CCN2 Chemical compound O=C(C1=CC=CN(c(cc2)ccc2F)C1=O)Nc(cc1)cc(F)c1Oc1ccnc2c1CCN2 KZLUVOZMCBNEOV-UHFFFAOYSA-N 0.000 description 1
- SDJRRBSJTIGZJT-UHFFFAOYSA-N O=C(C1=CC=CN(c(cc2)ccc2F)C1=O)Nc(cc1)cc(F)c1Oc1ccnc2c1OCCN2 Chemical compound O=C(C1=CC=CN(c(cc2)ccc2F)C1=O)Nc(cc1)cc(F)c1Oc1ccnc2c1OCCN2 SDJRRBSJTIGZJT-UHFFFAOYSA-N 0.000 description 1
- WPJGHIVGAOVUAT-UHFFFAOYSA-N OC(C1=CC=CN(c(cc2)ccc2F)C1=O)=O Chemical compound OC(C1=CC=CN(c(cc2)ccc2F)C1=O)=O WPJGHIVGAOVUAT-UHFFFAOYSA-N 0.000 description 1
- IZTVDTIADHKZNM-UHFFFAOYSA-N OC(C1=CNC=C(c(cc2)ccc2F)C1=O)=O Chemical compound OC(C1=CNC=C(c(cc2)ccc2F)C1=O)=O IZTVDTIADHKZNM-UHFFFAOYSA-N 0.000 description 1
- WQSJGRLFXQMBDF-UHFFFAOYSA-N Oc1c2OCCNc2ncc1 Chemical compound Oc1c2OCCNc2ncc1 WQSJGRLFXQMBDF-UHFFFAOYSA-N 0.000 description 1
- WFQDTOYDVUWQMS-UHFFFAOYSA-N [O-][N+](c(cc1)ccc1F)=O Chemical compound [O-][N+](c(cc1)ccc1F)=O WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
-
- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs 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
-
- 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
- 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
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- 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
-
- 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
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Oncology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Ophthalmology & Optometry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNPCT/CN2012/077924 | 2012-06-29 | ||
| CN2012077924 | 2012-06-29 | ||
| PCT/CN2013/078592 WO2014000713A1 (en) | 2012-06-29 | 2013-07-01 | NOVEL FUSED PYRIDINE DERIVATIVES USEFUL AS c-MET TYROSINE KINASE INHIBITORS |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015521634A JP2015521634A (ja) | 2015-07-30 |
| JP2015521634A5 JP2015521634A5 (forum.php) | 2015-10-08 |
| JP6059342B2 true JP6059342B2 (ja) | 2017-01-11 |
Family
ID=49782283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015518816A Expired - Fee Related JP6059342B2 (ja) | 2012-06-29 | 2013-07-01 | ｃ−ＭＥＴチロシンキナーゼ阻害剤として有用な新規な縮合ピリジン誘導体 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US9617257B2 (forum.php) |
| EP (1) | EP2867223B1 (forum.php) |
| JP (1) | JP6059342B2 (forum.php) |
| KR (3) | KR101726522B1 (forum.php) |
| AU (1) | AU2013283993B2 (forum.php) |
| BR (1) | BR112014032745B1 (forum.php) |
| CA (1) | CA2878049C (forum.php) |
| ES (1) | ES2698511T3 (forum.php) |
| IN (1) | IN2015DN00372A (forum.php) |
| RU (1) | RU2619130C2 (forum.php) |
| SG (1) | SG11201408750VA (forum.php) |
| TW (1) | TWI520962B (forum.php) |
| WO (1) | WO2014000713A1 (forum.php) |
| ZA (1) | ZA201500344B (forum.php) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106279147A (zh) * | 2015-05-21 | 2017-01-04 | 中国科学院上海药物研究所 | 一种吡啶并氮杂环化合物及其制备方法和用途 |
| ES2769124T3 (es) * | 2015-07-20 | 2020-06-24 | Betta Pharmaceuticals Co Ltd | Forma cristalina de maleato de derivados de piridina condensados y usos de la misma |
| CN106924260B (zh) * | 2015-12-31 | 2018-05-25 | 北京浦润奥生物科技有限责任公司 | 化合物在制备用于治疗脑胶质瘤的药物中的用途 |
| SG11201806302RA (en) | 2016-02-05 | 2018-08-30 | Denali Therapeutics Inc | Inhibitors of receptor-interacting protein kinase 1 |
| PL3552017T3 (pl) | 2016-12-09 | 2022-08-08 | Denali Therapeutics Inc. | Związki użyteczne jako inhibitory RIPK1 |
| KR20200011965A (ko) * | 2017-05-26 | 2020-02-04 | 아이크노스 사이언스 에스. 아. | Map4k1의 신규한 억제제 |
| JP7131837B2 (ja) * | 2017-06-19 | 2022-09-06 | アビスコ セラピューティクス カンパニー リミテッド | Ｃｓｆ－１ｒ阻害活性を有するアザアリール誘導体、その製造方法および応用 |
| CN109988108B (zh) * | 2017-12-29 | 2022-04-29 | 江苏豪森药业集团有限公司 | 一种卡博替尼的制备方法 |
| EA202191541A1 (ru) * | 2018-12-14 | 2022-01-21 | Бета Фарма, Инк. | ЗАМЕЩЕННЫЕ ФОСФОРОРГАНИЧЕСКИМИ ГРУППАМИ СОЕДИНЕНИЯ В КАЧЕСТВЕ ИНГИБИТОРОВ c-MET И ИХ ТЕРАПЕВТИЧЕСКИЕ ПРИМЕНЕНИЯ |
| MX2021009863A (es) | 2019-03-21 | 2021-11-12 | Onxeo | Una molecula dbait en combinacion con inhibidor de quinasa para el tratamiento del cancer. |
| KR20220098759A (ko) | 2019-11-08 | 2022-07-12 | 인쎄름 (엥스띠뛰 나씨오날 드 라 쌍떼 에 드 라 흐쉐르슈 메디깔) | 키나제 억제제에 대해 내성을 획득한 암의 치료 방법 |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| TWI812301B (zh) * | 2021-06-24 | 2023-08-11 | 南韓商Ｌｇ化學股份有限公司 | 作為ｒｏｎ抑制劑之新穎尿素衍生物化合物 |
| AU2023206890A1 (en) | 2022-01-12 | 2024-08-22 | Denali Therapeutics Inc. | Crystalline forms of (s)-5-benzyl-n-(5-methyl-4-oxo-2, 3,4,5- tetrahydropyrido [3,2-b] [l,4]oxazepin-3-yl)-4h-l,2,4-triazole-3-carboxamide |
| EP4289427A1 (en) * | 2022-06-10 | 2023-12-13 | Anagenesis Biotechnologies | Dihydro[1,8]naphthyridin-7-one and pyrido[3,2-b][1,4]oxazin-3-one for use in treating cancer, and metastases in particular. |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070213374A1 (en) | 2003-07-07 | 2007-09-13 | Merck Patent Gmbh | Malonamide Derivatives |
| DE10357510A1 (de) | 2003-12-09 | 2005-07-07 | Bayer Healthcare Ag | Heteroarylsubstituierte Benzole |
| US20050288290A1 (en) * | 2004-06-28 | 2005-12-29 | Borzilleri Robert M | Fused heterocyclic kinase inhibitors |
| EP1773826A4 (en) * | 2004-07-02 | 2009-06-03 | Exelixis Inc | MODULATORS OF C-MET AND THEIR METHOD OF USE |
| MX2007001216A (es) * | 2004-07-30 | 2007-03-23 | Methylgene Inc | Inhibidores de la senalizacion del receptor del factor de crecimiento endotelial vascular y del receptor del factor de crecimiento del hepatocito. |
| JP2008521900A (ja) | 2004-11-30 | 2008-06-26 | アムジエン・インコーポレーテツド | キノリン及びキナゾリン類似体並びにがん治療のための医薬としてのその使用 |
| JO2787B1 (en) * | 2005-04-27 | 2014-03-15 | امجين إنك, | Alternative amide derivatives and methods of use |
| NZ563774A (en) | 2005-05-20 | 2010-04-30 | Methylgene Inc | Inhibitors of VEGF receptor and HGF receptor signaling |
| JP2010507618A (ja) * | 2006-10-27 | 2010-03-11 | グラクソ グループ リミテッド | ｃ−Ｍｅｔキナーゼ阻害薬としての７−アザインドール誘導体 |
| US7960567B2 (en) | 2007-05-02 | 2011-06-14 | Amgen Inc. | Compounds and methods useful for treating asthma and allergic inflammation |
| MX2011004018A (es) * | 2008-10-14 | 2011-06-24 | Ning Xi | Compuestos y metodos de uso. |
| KR100961410B1 (ko) * | 2008-10-14 | 2010-06-09 | (주)네오팜 | 단백질 키나제 억제제로서 헤테로사이클릭 화합물 |
| CN102086211B (zh) * | 2009-12-08 | 2013-09-11 | 广东东阳光药业有限公司 | 作为蛋白激酶抑制剂的芳杂环化合物 |
| ES2598530T3 (es) * | 2010-07-14 | 2017-01-27 | Betta Pharmaceuticals Co., Ltd. | Nuevos derivados heterocíclicos condensados útiles como inhibidores de la tirosina quinasa c-Met |
-
2013
- 2013-06-29 TW TW102123415A patent/TWI520962B/zh not_active IP Right Cessation
- 2013-07-01 EP EP13809182.2A patent/EP2867223B1/en not_active Not-in-force
- 2013-07-01 JP JP2015518816A patent/JP6059342B2/ja not_active Expired - Fee Related
- 2013-07-01 KR KR1020157002238A patent/KR101726522B1/ko not_active Expired - Fee Related
- 2013-07-01 KR KR1020177003335A patent/KR101726555B1/ko not_active Expired - Fee Related
- 2013-07-01 SG SG11201408750VA patent/SG11201408750VA/en unknown
- 2013-07-01 AU AU2013283993A patent/AU2013283993B2/en not_active Ceased
- 2013-07-01 US US14/411,515 patent/US9617257B2/en not_active Expired - Fee Related
- 2013-07-01 KR KR1020177003331A patent/KR101770545B1/ko not_active Expired - Fee Related
- 2013-07-01 IN IN372DEN2015 patent/IN2015DN00372A/en unknown
- 2013-07-01 CA CA2878049A patent/CA2878049C/en not_active Expired - Fee Related
- 2013-07-01 RU RU2015102057A patent/RU2619130C2/ru active
- 2013-07-01 ES ES13809182T patent/ES2698511T3/es active Active
- 2013-07-01 WO PCT/CN2013/078592 patent/WO2014000713A1/en active Application Filing
- 2013-07-01 BR BR112014032745-9A patent/BR112014032745B1/pt not_active IP Right Cessation
-
2015
- 2015-01-16 ZA ZA2015/00344A patent/ZA201500344B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR112014032745B1 (pt) | 2022-01-04 |
| KR101726522B1 (ko) | 2017-04-12 |
| SG11201408750VA (en) | 2015-01-29 |
| EP2867223B1 (en) | 2018-09-05 |
| ES2698511T3 (es) | 2019-02-05 |
| CA2878049A1 (en) | 2014-01-03 |
| WO2014000713A1 (en) | 2014-01-03 |
| KR101770545B1 (ko) | 2017-08-22 |
| IN2015DN00372A (forum.php) | 2015-06-12 |
| AU2013283993B2 (en) | 2016-07-07 |
| AU2013283993A1 (en) | 2015-02-05 |
| JP2015521634A (ja) | 2015-07-30 |
| KR101726555B1 (ko) | 2017-04-12 |
| KR20170017015A (ko) | 2017-02-14 |
| KR20150031320A (ko) | 2015-03-23 |
| EP2867223A1 (en) | 2015-05-06 |
| HK1207642A1 (en) | 2016-02-05 |
| TW201418254A (zh) | 2014-05-16 |
| TWI520962B (zh) | 2016-02-11 |
| EP2867223A4 (en) | 2016-01-06 |
| US9617257B2 (en) | 2017-04-11 |
| CA2878049C (en) | 2016-12-13 |
| RU2619130C2 (ru) | 2017-05-12 |
| KR20170017014A (ko) | 2017-02-14 |
| RU2015102057A (ru) | 2016-08-20 |
| BR112014032745A2 (pt) | 2017-06-27 |
| ZA201500344B (en) | 2016-08-31 |
| US20150315210A1 (en) | 2015-11-05 |
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