CN106573897B - 作为mIDH1抑制剂的苯并咪唑-2-胺 - Google Patents
作为mIDH1抑制剂的苯并咪唑-2-胺 Download PDFInfo
- Publication number
- CN106573897B CN106573897B CN201580019265.9A CN201580019265A CN106573897B CN 106573897 B CN106573897 B CN 106573897B CN 201580019265 A CN201580019265 A CN 201580019265A CN 106573897 B CN106573897 B CN 106573897B
- Authority
- CN
- China
- Prior art keywords
- amino
- phenyl
- trimethylcyclohexyl
- alkyl
- propionic acid
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- 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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14154680.4 | 2014-02-11 | ||
| EP14154680 | 2014-02-11 | ||
| EP14182002 | 2014-08-22 | ||
| EP14182002.7 | 2014-08-22 | ||
| PCT/EP2015/052676 WO2015121210A1 (en) | 2014-02-11 | 2015-02-10 | Benzimidazol-2-amines as midh1 inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106573897A CN106573897A (zh) | 2017-04-19 |
| CN106573897B true CN106573897B (zh) | 2019-09-24 |
Family
ID=52462928
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201580019265.9A Expired - Fee Related CN106573897B (zh) | 2014-02-11 | 2015-02-10 | 作为mIDH1抑制剂的苯并咪唑-2-胺 |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US9957235B2 (enExample) |
| EP (1) | EP3105209B1 (enExample) |
| JP (1) | JP6534675B2 (enExample) |
| KR (1) | KR20160115991A (enExample) |
| CN (1) | CN106573897B (enExample) |
| AP (1) | AP2016009371A0 (enExample) |
| AU (1) | AU2015217788B2 (enExample) |
| BR (1) | BR112016018604A2 (enExample) |
| CA (1) | CA2939026A1 (enExample) |
| CL (1) | CL2016002033A1 (enExample) |
| CR (1) | CR20160361A (enExample) |
| CU (1) | CU24410B1 (enExample) |
| DO (1) | DOP2016000208A (enExample) |
| EA (1) | EA031655B1 (enExample) |
| IL (1) | IL246785A0 (enExample) |
| MX (1) | MX2016010474A (enExample) |
| PE (1) | PE20170143A1 (enExample) |
| PH (1) | PH12016501581A1 (enExample) |
| SG (1) | SG11201605810WA (enExample) |
| SV (1) | SV2016005257A (enExample) |
| TW (1) | TWI666202B (enExample) |
| UY (1) | UY35991A (enExample) |
| WO (1) | WO2015121210A1 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG11201605810WA (en) | 2014-02-11 | 2016-08-30 | Bayer Pharma AG | Benzimidazol-2-amines as midh1 inhibitors |
| US9951027B2 (en) | 2014-02-11 | 2018-04-24 | Bayer Pharma Aktiengesellschaft | Benzimidazol-2-amines as MIDH1 inhibitors |
| PT3733662T (pt) | 2014-09-19 | 2023-08-18 | Forma Therapeutics Inc | Derivados piridin-2(1h)-ona-quinolinona como inibidores de isocitrato desidrogenase mutante |
| ES2768694T3 (es) | 2014-09-19 | 2020-06-23 | Forma Therapeutics Inc | Composiciones de quinolinona pirimidinas como inhibidores de isocitrato dehidrogenasa mutante |
| CA2965201A1 (en) * | 2014-10-23 | 2016-04-28 | Bayer Pharma Aktiengesellschaft | Benzimidazol-2-amines as midh1 inhibitors |
| CN107108554B (zh) * | 2014-10-23 | 2020-11-06 | 德国癌症研究中心 | 作为midh1抑制剂用于治疗肿瘤的1-环己基-2-苯基氨基苯并咪唑 |
| JP6830909B2 (ja) * | 2015-06-08 | 2021-02-17 | ドイチェス クレープスフォルシュングスツェントルム シュティフトゥング デス エッフェントリッヒェン レヒツ | mIDH1阻害剤としてのN−メンチルベンズイミダゾール |
| ES2877424T3 (es) | 2015-07-07 | 2021-11-16 | Deutsches Krebsforschungszentrum Stiftung Des Oeffentlichen Rechts | 2-Aril- y 2-arilalquil-bencimidazoles como inhibidores de MIDH1 |
| CN108026052B (zh) * | 2015-07-16 | 2021-10-08 | 德国癌症研究公共权益基金会 | 作为mIDH1抑制剂的5-羟烷基苯并咪唑类 |
| EP3121166A1 (en) | 2015-07-21 | 2017-01-25 | Bayer Pharma Aktiengesellschaft | Fused imidazoles as midh1 inhibitors |
| TW201708193A (zh) * | 2015-07-27 | 2017-03-01 | 拜耳製藥公司 | 突變之異檸檬酸脫氫酶idh1 r132h之抑制劑 |
| TW201718513A (zh) * | 2015-07-27 | 2017-06-01 | 拜耳製藥公司 | 製備經取代之3-(2-苯胺-1-環己基-1h-苯并咪唑-5-基)丙酸衍生物之方法 |
| MX2018009633A (es) * | 2016-02-09 | 2018-12-17 | Inventisbio Inc | Inhibidor de indoleamina-2,3-dioxigenasa (ido). |
| WO2019015672A1 (zh) * | 2017-07-21 | 2019-01-24 | 南京明德新药研发股份有限公司 | 吡啶并咪唑类化合物及其应用 |
| US20210113598A1 (en) * | 2017-08-01 | 2021-04-22 | Deutsches Krebsforschungszentrum (DKFZ) Stiftung des öffentlichen Rechts | Combination of MIDH1 Inhibitors and DNA Hypomethylating Agents (HMA) |
| US11311527B2 (en) | 2018-05-16 | 2022-04-26 | Forma Therapeutics, Inc. | Inhibiting mutant isocitrate dehydrogenase 1 (mIDH-1) |
| EP3720442B1 (en) | 2018-05-16 | 2022-12-28 | Forma Therapeutics, Inc. | Inhibiting mutant idh-1 |
| US10532047B2 (en) | 2018-05-16 | 2020-01-14 | Forma Therapeutics, Inc. | Solid forms of ((S)-5-((1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl)amino)-1-methyl-6-oxo-1,6-dihydropyridine-2-carbonitrile |
| US11013733B2 (en) | 2018-05-16 | 2021-05-25 | Forma Therapeutics, Inc. | Inhibiting mutant isocitrate dehydrogenase 1 (mlDH-1) |
| US11013734B2 (en) | 2018-05-16 | 2021-05-25 | Forma Therapeutics, Inc. | Treating patients harboring an isocitrate dehydrogenase-1 (IDH-1) mutation |
| WO2020001474A1 (zh) * | 2018-06-26 | 2020-01-02 | 南京明德新药研发有限公司 | 苯并咪唑衍生物及其作为idh1抑制剂的应用 |
| TWI760017B (zh) * | 2019-12-23 | 2022-04-01 | 大陸商昆藥集團股份有限公司 | 一種idh1突變體抑制劑的鹽型、晶型及其製備方法 |
| US12014835B2 (en) | 2020-02-19 | 2024-06-18 | Vanderbilt University | Methods for evaluating therapeutic benefit of combination therapies |
| MX2023000902A (es) * | 2020-07-21 | 2023-02-22 | Daiichi Sankyo Co Ltd | Combinacion farmaceutica de temozolomida e inhibidor de la enzima mutante idh1. |
| CN112062687B (zh) * | 2020-09-02 | 2023-11-21 | 上海信谊万象药业股份有限公司 | 一种盐酸阿扎司琼中间体3-氨基-5-氯-2-羟基苯甲酸甲酯的合成方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008153701A1 (en) * | 2007-05-24 | 2008-12-18 | Schering Corporation | Compounds for inhibiting ksp kinesin activity |
| WO2010151441A1 (en) * | 2009-06-23 | 2010-12-29 | Translational Genomics Research Institute | Benzamide derivatives |
| CN103435554A (zh) * | 2013-09-06 | 2013-12-11 | 中国药科大学 | 2-苯氨基苯并咪唑类化合物及其用途 |
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| FR2643903A1 (fr) | 1989-03-03 | 1990-09-07 | Union Pharma Scient Appl | Nouveaux derives de benzimidazole, leurs procedes de preparation, intermediaires de synthese, compositions pharmaceutiques les contenant, utiles notamment pour le traitement des maladies cardiovasculaires, et des ulceres duodenaux |
| CN1161340C (zh) | 1998-11-30 | 2004-08-11 | 先灵公司 | 为玻连蛋白受体拮抗剂的苯并咪唑化合物 |
| US6340681B1 (en) | 1999-07-16 | 2002-01-22 | Pfizer Inc | 2-benzimidazolylamine compounds as ORL-1-receptor agonists |
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| JPWO2006038738A1 (ja) | 2004-10-08 | 2008-05-15 | 武田薬品工業株式会社 | 受容体機能調節剤 |
| US7893267B2 (en) | 2005-03-14 | 2011-02-22 | High Point Pharmaceuticals, Llc | Benzazole derivatives, compositions, and methods of use as β-secretase inhibitors |
| US8168800B2 (en) | 2007-11-02 | 2012-05-01 | The Regents Of The University Of California | Aβ-binding small molecules |
| WO2009116074A2 (en) | 2008-02-13 | 2009-09-24 | Cadila Healthcare Limited | Substituted benzimidazoles as cannabinoid modulator |
| UY32138A (es) | 2008-09-25 | 2010-04-30 | Boehringer Ingelheim Int | Amidas sustituidas del ácido 2-(2,6-dicloro-fenilamino)-6-fluoro-1-metil-1h-bencimidazol-5-carboxílico y sus sales farmacéuticamente aceptables |
| UY32470A (es) | 2009-03-05 | 2010-10-29 | Boehringer Ingelheim Int | Derivados de 2-{2-cloro-5-[(sustituido) metil]fenilamino} -1-metil]fenilamino}-1-metilbencimidazol-5-carboxamidas-n-(sustituidas) y sus sales fisiológicamente aceptables, composiciones conteniéndolos y aplicaciones |
| ES2642109T3 (es) | 2009-12-09 | 2017-11-15 | Agios Pharmaceuticals, Inc. | Compuestos terapéuticamente activos para su uso en el tratamiento de cáncer caracterizados por tener una mutación de IDH |
| WO2012172043A1 (en) * | 2011-06-15 | 2012-12-20 | Laboratoire Biodim | Purine derivatives and their use as pharmaceuticals for prevention or treatment of bacterial infections |
| CN102827170A (zh) | 2011-06-17 | 2012-12-19 | 安吉奥斯医药品有限公司 | 治疗活性组合物和它们的使用方法 |
| SG11201605810WA (en) | 2014-02-11 | 2016-08-30 | Bayer Pharma AG | Benzimidazol-2-amines as midh1 inhibitors |
| US9951027B2 (en) | 2014-02-11 | 2018-04-24 | Bayer Pharma Aktiengesellschaft | Benzimidazol-2-amines as MIDH1 inhibitors |
| CN107108554B (zh) | 2014-10-23 | 2020-11-06 | 德国癌症研究中心 | 作为midh1抑制剂用于治疗肿瘤的1-环己基-2-苯基氨基苯并咪唑 |
| CA2965201A1 (en) | 2014-10-23 | 2016-04-28 | Bayer Pharma Aktiengesellschaft | Benzimidazol-2-amines as midh1 inhibitors |
| JP2018515623A (ja) | 2015-05-18 | 2018-06-14 | トランスレイショナル・ドラッグ・ディベロップメント・エルエルシー | キナーゼ阻害剤としての複素環式化合物 |
| CA3025145A1 (en) | 2015-05-22 | 2016-12-01 | Translational Drug Development Llc | Benzamide and active compound compositions and methods of use |
| JP6830909B2 (ja) | 2015-06-08 | 2021-02-17 | ドイチェス クレープスフォルシュングスツェントルム シュティフトゥング デス エッフェントリッヒェン レヒツ | mIDH1阻害剤としてのN−メンチルベンズイミダゾール |
| ES2877424T3 (es) | 2015-07-07 | 2021-11-16 | Deutsches Krebsforschungszentrum Stiftung Des Oeffentlichen Rechts | 2-Aril- y 2-arilalquil-bencimidazoles como inhibidores de MIDH1 |
| CN108026052B (zh) | 2015-07-16 | 2021-10-08 | 德国癌症研究公共权益基金会 | 作为mIDH1抑制剂的5-羟烷基苯并咪唑类 |
| EP3121166A1 (en) | 2015-07-21 | 2017-01-25 | Bayer Pharma Aktiengesellschaft | Fused imidazoles as midh1 inhibitors |
| TW201718513A (zh) | 2015-07-27 | 2017-06-01 | 拜耳製藥公司 | 製備經取代之3-(2-苯胺-1-環己基-1h-苯并咪唑-5-基)丙酸衍生物之方法 |
| TW201708193A (zh) | 2015-07-27 | 2017-03-01 | 拜耳製藥公司 | 突變之異檸檬酸脫氫酶idh1 r132h之抑制劑 |
| CN109071460B (zh) | 2016-03-02 | 2022-08-09 | 转化药物开发有限责任公司 | 氨基苯并咪唑衍生物 |
-
2015
- 2015-02-10 SG SG11201605810WA patent/SG11201605810WA/en unknown
- 2015-02-10 AP AP2016009371A patent/AP2016009371A0/en unknown
- 2015-02-10 AU AU2015217788A patent/AU2015217788B2/en not_active Ceased
- 2015-02-10 US US15/118,154 patent/US9957235B2/en active Active
- 2015-02-10 CA CA2939026A patent/CA2939026A1/en not_active Abandoned
- 2015-02-10 WO PCT/EP2015/052676 patent/WO2015121210A1/en not_active Ceased
- 2015-02-10 EP EP15703288.9A patent/EP3105209B1/en active Active
- 2015-02-10 CU CU2016000120A patent/CU24410B1/es unknown
- 2015-02-10 EA EA201691590A patent/EA031655B1/ru not_active IP Right Cessation
- 2015-02-10 CN CN201580019265.9A patent/CN106573897B/zh not_active Expired - Fee Related
- 2015-02-10 PE PE2016001465A patent/PE20170143A1/es unknown
- 2015-02-10 CR CR20160361A patent/CR20160361A/es unknown
- 2015-02-10 BR BR112016018604A patent/BR112016018604A2/pt not_active Application Discontinuation
- 2015-02-10 KR KR1020167024825A patent/KR20160115991A/ko not_active Withdrawn
- 2015-02-10 MX MX2016010474A patent/MX2016010474A/es unknown
- 2015-02-10 JP JP2016551221A patent/JP6534675B2/ja not_active Expired - Fee Related
- 2015-02-11 TW TW104104623A patent/TWI666202B/zh not_active IP Right Cessation
- 2015-02-11 UY UY0001035991A patent/UY35991A/es not_active Application Discontinuation
-
2016
- 2016-07-14 IL IL246785A patent/IL246785A0/en unknown
- 2016-08-10 PH PH12016501581A patent/PH12016501581A1/en unknown
- 2016-08-11 SV SV2016005257A patent/SV2016005257A/es unknown
- 2016-08-11 CL CL2016002033A patent/CL2016002033A1/es unknown
- 2016-08-11 DO DO2016000208A patent/DOP2016000208A/es unknown
-
2018
- 2018-03-16 US US15/923,895 patent/US10442772B2/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008153701A1 (en) * | 2007-05-24 | 2008-12-18 | Schering Corporation | Compounds for inhibiting ksp kinesin activity |
| WO2010151441A1 (en) * | 2009-06-23 | 2010-12-29 | Translational Genomics Research Institute | Benzamide derivatives |
| CN103435554A (zh) * | 2013-09-06 | 2013-12-11 | 中国药科大学 | 2-苯氨基苯并咪唑类化合物及其用途 |
Non-Patent Citations (4)
| Title |
|---|
| An Inhibitor of Mutant IDH1 Delays Growth and Promotes Differentiation of Glioma Cells;Dan Rohle,et al.;《Science》;20130503;第340卷;第626-630页 * |
| Cancer-associated IDH1 mutations produce 2-hydroxyglutarate;Lenny Dang,et al.;《Nature》;20091210;第462卷;第739-744页 * |
| IDH1基因在人脑胶质瘤中突变及其功能意义研究;曾飞跃.;《中国博士学位论文全文数据库·医药卫生科技辑》;20101115(第11期);E072-182 * |
| IDH1基因突变与胶质瘤;王国良.;《中国微侵袭神经外科杂志》;20120820;第17卷(第8期);第379-381页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CL2016002033A1 (es) | 2017-03-31 |
| JP6534675B2 (ja) | 2019-06-26 |
| SV2016005257A (es) | 2018-10-02 |
| US20190062285A1 (en) | 2019-02-28 |
| AP2016009371A0 (en) | 2016-08-31 |
| EA201691590A1 (ru) | 2017-02-28 |
| CU24410B1 (es) | 2019-05-03 |
| UY35991A (es) | 2015-09-30 |
| PH12016501581A1 (en) | 2017-02-06 |
| CR20160361A (es) | 2016-10-03 |
| TWI666202B (zh) | 2019-07-21 |
| CN106573897A (zh) | 2017-04-19 |
| JP2017505790A (ja) | 2017-02-23 |
| CU20160120A7 (es) | 2016-12-23 |
| EP3105209A1 (en) | 2016-12-21 |
| WO2015121210A1 (en) | 2015-08-20 |
| IL246785A0 (en) | 2016-08-31 |
| DOP2016000208A (es) | 2016-09-15 |
| MX2016010474A (es) | 2016-10-31 |
| TW201613874A (en) | 2016-04-16 |
| CA2939026A1 (en) | 2015-08-20 |
| US9957235B2 (en) | 2018-05-01 |
| KR20160115991A (ko) | 2016-10-06 |
| BR112016018604A2 (pt) | 2017-08-08 |
| SG11201605810WA (en) | 2016-08-30 |
| EP3105209B1 (en) | 2019-08-21 |
| AU2015217788A1 (en) | 2016-08-04 |
| PE20170143A1 (es) | 2017-03-19 |
| US10442772B2 (en) | 2019-10-15 |
| EA031655B1 (ru) | 2019-02-28 |
| AU2015217788B2 (en) | 2019-06-27 |
| US20170197921A1 (en) | 2017-07-13 |
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