AU2014255608B2 - Stable, protracted GLP-1/glucagon receptor co-agonists for medical use - Google Patents
Stable, protracted GLP-1/glucagon receptor co-agonists for medical use Download PDFInfo
- Publication number
- AU2014255608B2 AU2014255608B2 AU2014255608A AU2014255608A AU2014255608B2 AU 2014255608 B2 AU2014255608 B2 AU 2014255608B2 AU 2014255608 A AU2014255608 A AU 2014255608A AU 2014255608 A AU2014255608 A AU 2014255608A AU 2014255608 B2 AU2014255608 B2 AU 2014255608B2
- Authority
- AU
- Australia
- Prior art keywords
- amino
- carboxy
- butanoyl
- ethoxy
- leu27
- 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.)
- Ceased
Links
- 0 CC(C)(C(*)=O)NC([C@](Cc1cnc[n]1)N)=O Chemical compound CC(C)(C(*)=O)NC([C@](Cc1cnc[n]1)N)=O 0.000 description 15
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- SCTFAMICVNGRHM-WEDXCCLWSA-N C[C@H]([C@@H](C(N)=O)NC([C@H](CCCCNC(CNS)=O)NI)=O)O Chemical compound C[C@H]([C@@H](C(N)=O)NC([C@H](CCCCNC(CNS)=O)NI)=O)O SCTFAMICVNGRHM-WEDXCCLWSA-N 0.000 description 2
- OKLUTIDHARRSIC-UHFFFAOYSA-N CC(C)(C=O)N Chemical compound CC(C)(C=O)N OKLUTIDHARRSIC-UHFFFAOYSA-N 0.000 description 1
- ZNVDFDYJCFSOKJ-UHFFFAOYSA-N CC(C)(C=O)NN Chemical compound CC(C)(C=O)NN ZNVDFDYJCFSOKJ-UHFFFAOYSA-N 0.000 description 1
- SWZGPUUUGJYYDN-BBACVFHCSA-N CC(CCCCCCCCCCCCCCCCC(N[C@@H](CCC(N[C@@H](CCC(NCCOCCOCC(N[C@@H](CCC(N[C@@H](CCC(N)=O)C(O)=O)=O)C(O)=O)=O)=O)C(O)=O)=O)C(O)=O)=O)=O Chemical compound CC(CCCCCCCCCCCCCCCCC(N[C@@H](CCC(N[C@@H](CCC(NCCOCCOCC(N[C@@H](CCC(N[C@@H](CCC(N)=O)C(O)=O)=O)C(O)=O)=O)=O)C(O)=O)=O)C(O)=O)=O)=O SWZGPUUUGJYYDN-BBACVFHCSA-N 0.000 description 1
- SMAMCTDOGLXGJJ-FSEITFBQSA-N CC(COCCOCCNC(COCCOCCNC(CC[C@@H](C(O)=O)NC(CC[C@@H](C(O)=O)NC(CC[C@@H](C(O)=O)NC(CCCCCCCCCCCCCCCCC(O)=O)=O)=O)=O)=O)=O)=O Chemical compound CC(COCCOCCNC(COCCOCCNC(CC[C@@H](C(O)=O)NC(CC[C@@H](C(O)=O)NC(CC[C@@H](C(O)=O)NC(CCCCCCCCCCCCCCCCC(O)=O)=O)=O)=O)=O)=O)=O SMAMCTDOGLXGJJ-FSEITFBQSA-N 0.000 description 1
- CWUXDDSSIKCDHK-IGMOWHQGSA-N CCCCNC(CC[C@@H](C(O)=O)NC(CC[C@@H](C(O)=O)NC(COCCOCCNC(COCCOCCNC(CC[C@@H](C(O)=O)NC(CCCCCCCCCCCCCCCCC(O)=O)=O)=O)=O)=O)=O)=O Chemical compound CCCCNC(CC[C@@H](C(O)=O)NC(CC[C@@H](C(O)=O)NC(COCCOCCNC(COCCOCCNC(CC[C@@H](C(O)=O)NC(CCCCCCCCCCCCCCCCC(O)=O)=O)=O)=O)=O)=O)=O CWUXDDSSIKCDHK-IGMOWHQGSA-N 0.000 description 1
- PTRBRHFURJAXOM-ZBIPGQCISA-N C[C@H]([C@@H](C(C)=O)NC(C(CCCCNC(CNS)=O)NI)=O)O Chemical compound C[C@H]([C@@H](C(C)=O)NC(C(CCCCNC(CNS)=O)NI)=O)O PTRBRHFURJAXOM-ZBIPGQCISA-N 0.000 description 1
- NNZBXTCWFOMVKN-FZYNNEITSA-N C[C@H]([C@@H](C(C)=O)NC([C@H](CCCCNC(CC[C@@H](C(O)=O)NC(CC[C@@H](C(O)=O)NC(COCCOCCNC(COCCOCCNC(CC[C@@H](C(O)=O)NC(CCCCCCCCCCCCCCCCC(O)=O)=O)=O)=O)=O)=O)=O)NI)=O)O Chemical compound C[C@H]([C@@H](C(C)=O)NC([C@H](CCCCNC(CC[C@@H](C(O)=O)NC(CC[C@@H](C(O)=O)NC(COCCOCCNC(COCCOCCNC(CC[C@@H](C(O)=O)NC(CCCCCCCCCCCCCCCCC(O)=O)=O)=O)=O)=O)=O)=O)NI)=O)O NNZBXTCWFOMVKN-FZYNNEITSA-N 0.000 description 1
- NHCZOEAQHOURAP-YKKXUYLKSA-N NC([C@H](CCCCNC(CC[C@@H](C(O)=O)NC(CC[C@@H](C(O)=O)NC(COCCOCCNC(COCCOCCNC(CC[C@@H](C(O)=O)NC(CCCCCCCCCCCCCCCCC(O)=O)=O)=O)=O)=O)=O)=O)NN)=O Chemical compound NC([C@H](CCCCNC(CC[C@@H](C(O)=O)NC(CC[C@@H](C(O)=O)NC(COCCOCCNC(COCCOCCNC(CC[C@@H](C(O)=O)NC(CCCCCCCCCCCCCCCCC(O)=O)=O)=O)=O)=O)=O)=O)NN)=O NHCZOEAQHOURAP-YKKXUYLKSA-N 0.000 description 1
- LETGJOKXNWDKQV-YKKXUYLKSA-N NC([C@H](CCCCNC(CC[C@@H](C(O)=O)NC(CC[C@@H](C(O)=O)NC(COCCOCCNC(COCCOCCNC(CC[C@@H](C(O)=O)NC(CCCCCCCCCCCCCCCCC(O)=O)=O)=O)=O)=O)=O)=O)NS)=O Chemical compound NC([C@H](CCCCNC(CC[C@@H](C(O)=O)NC(CC[C@@H](C(O)=O)NC(COCCOCCNC(COCCOCCNC(CC[C@@H](C(O)=O)NC(CCCCCCCCCCCCCCCCC(O)=O)=O)=O)=O)=O)=O)=O)NS)=O LETGJOKXNWDKQV-YKKXUYLKSA-N 0.000 description 1
- IAMZLROTAPOMFR-UHFFFAOYSA-N NNC1(CCC1)C=O Chemical compound NNC1(CCC1)C=O IAMZLROTAPOMFR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/575—Hormones
- C07K14/605—Glucagons
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/22—Hormones
- A61K38/26—Glucagons
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/22—Hormones
- A61K38/28—Insulins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Endocrinology (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Gastroenterology & Hepatology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Zoology (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biophysics (AREA)
- Toxicology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13164272.0 | 2013-04-18 | ||
| EP13164272 | 2013-04-18 | ||
| US201361814969P | 2013-04-23 | 2013-04-23 | |
| US61/814,969 | 2013-04-23 | ||
| EP13196656 | 2013-12-11 | ||
| EP13196656.6 | 2013-12-11 | ||
| PCT/EP2014/058084 WO2014170496A1 (en) | 2013-04-18 | 2014-04-22 | Stable, protracted glp-1/glucagon receptor co-agonists for medical use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2014255608A1 AU2014255608A1 (en) | 2015-10-08 |
| AU2014255608B2 true AU2014255608B2 (en) | 2018-01-25 |
Family
ID=51730843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2014255608A Ceased AU2014255608B2 (en) | 2013-04-18 | 2014-04-22 | Stable, protracted GLP-1/glucagon receptor co-agonists for medical use |
Country Status (16)
| Country | Link |
|---|---|
| US (3) | US9474790B2 (enExample) |
| EP (1) | EP2986313B1 (enExample) |
| JP (1) | JP6594856B2 (enExample) |
| KR (1) | KR20160021758A (enExample) |
| CN (1) | CN105307672B (enExample) |
| AU (1) | AU2014255608B2 (enExample) |
| BR (1) | BR112015025464A2 (enExample) |
| CA (1) | CA2909581A1 (enExample) |
| MX (1) | MX362275B (enExample) |
| MY (1) | MY174727A (enExample) |
| PL (1) | PL2986313T3 (enExample) |
| RS (1) | RS59124B1 (enExample) |
| RU (1) | RU2683039C2 (enExample) |
| SI (1) | SI2986313T1 (enExample) |
| WO (1) | WO2014170496A1 (enExample) |
| ZA (1) | ZA201507010B (enExample) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX354705B (es) | 2011-09-23 | 2018-03-16 | Novo Nordisk As | Analogos de glucagon novedosos. |
| UA116217C2 (uk) | 2012-10-09 | 2018-02-26 | Санофі | Пептидна сполука як подвійний агоніст рецепторів glp1-1 та глюкагону |
| HUE035803T2 (en) | 2012-12-21 | 2018-05-28 | Sanofi Sa | Dual GLP1 / GIP or trigonal GLP1 / GIP / glucagon agonists |
| BR112015025464A2 (pt) | 2013-04-18 | 2017-10-10 | Novo Nordisk As | coagonistas do receptor de glp-1/glucagon estáveis, prolongados para uso médico |
| HUE045573T2 (hu) * | 2013-04-18 | 2020-01-28 | Novo Nordisk As | Stabil, hosszú hatóidejû GLP-1/glükagon receptor ko-agonisták, gyógyászati alkalmazásra |
| TW201609797A (zh) | 2013-12-13 | 2016-03-16 | 賽諾菲公司 | 雙重ｇｌｐ－１／升糖素受體促效劑 |
| EP3080154B1 (en) | 2013-12-13 | 2018-02-07 | Sanofi | Dual glp-1/gip receptor agonists |
| WO2015086730A1 (en) | 2013-12-13 | 2015-06-18 | Sanofi | Non-acylated exendin-4 peptide analogues |
| WO2015086728A1 (en) | 2013-12-13 | 2015-06-18 | Sanofi | Exendin-4 peptide analogues as dual glp-1/gip receptor agonists |
| TW201625668A (zh) | 2014-04-07 | 2016-07-16 | 賽諾菲公司 | 作為胜肽性雙重ｇｌｐ－１／昇糖素受體激動劑之艾塞那肽－４衍生物 |
| TW201625669A (zh) | 2014-04-07 | 2016-07-16 | 賽諾菲公司 | 衍生自艾塞那肽－４（Ｅｘｅｎｄｉｎ－４）之肽類雙重ＧＬＰ－１／升糖素受體促效劑 |
| TW201625670A (zh) | 2014-04-07 | 2016-07-16 | 賽諾菲公司 | 衍生自ｅｘｅｎｄｉｎ－４之雙重ｇｌｐ－１／升糖素受體促效劑 |
| CN117582516A (zh) * | 2014-05-28 | 2024-02-23 | 梅德瑞斯糖尿病有限责任公司 | 针对胰岛素抵抗的改良肽药物 |
| JP2017525656A (ja) | 2014-06-04 | 2017-09-07 | ノヴォ ノルディスク アー／エス | 医療用のｇｌｐ−１／グルカゴン受容体コアゴニスト |
| US9932381B2 (en) | 2014-06-18 | 2018-04-03 | Sanofi | Exendin-4 derivatives as selective glucagon receptor agonists |
| KR102291020B1 (ko) * | 2014-12-30 | 2021-08-20 | 한미약품 주식회사 | 안정성이 증가된 글루카곤 유도체 |
| KR102418477B1 (ko) * | 2014-12-30 | 2022-07-08 | 한미약품 주식회사 | 글루카곤 유도체 |
| AR105319A1 (es) | 2015-06-05 | 2017-09-27 | Sanofi Sa | Profármacos que comprenden un conjugado agonista dual de glp-1 / glucagón conector ácido hialurónico |
| WO2016198624A1 (en) | 2015-06-12 | 2016-12-15 | Sanofi | Exendin-4 derivatives as trigonal glp-1/glucagon/gip receptor agonists |
| WO2016198628A1 (en) | 2015-06-12 | 2016-12-15 | Sanofi | Non-acylated exendin-4 derivatives as dual glp-1/glucagon receptor agonists |
| FI3322437T3 (fi) | 2015-06-30 | 2024-02-20 | Hanmi Pharmaceutical Co Ltd | Glukagonijohdannainen ja sen pitkävaikutteisen konjugaatin käsittävä koostumus |
| TW201706291A (zh) | 2015-07-10 | 2017-02-16 | 賽諾菲公司 | 作為選擇性肽雙重ｇｌｐ－１／升糖素受體促效劑之新毒蜥外泌肽（ｅｘｅｎｄｉｎ－４）衍生物 |
| TWI622596B (zh) | 2015-10-26 | 2018-05-01 | 美國禮來大藥廠 | 升糖素受體促效劑 |
| JP6712323B2 (ja) | 2015-12-31 | 2020-06-17 | ハンミ ファーマシューティカル カンパニー リミテッド | グルカゴン、ｇｌｐ−１及びｇｉｐ受容体のすべてに活性を有する三重活性体 |
| RU2747877C2 (ru) * | 2016-01-13 | 2021-05-17 | Ново Нордиск А/С | Аналоги эфр(а) с заместителями - жирными кислотами |
| FR3050112B1 (fr) | 2016-04-15 | 2020-09-04 | Soc Civ Immobiliere Gecinq | Utilisation de l'acide fenofibrique dans le traitement des maladies hepatiques |
| CN122440793A (zh) | 2016-06-29 | 2026-07-24 | 韩美药品株式会社 | 胰高血糖素衍生物、其缀合物、包含其的组合物、和其治疗用途 |
| CN110945017B (zh) | 2017-07-19 | 2024-07-16 | 诺和诺德股份有限公司 | 双功能化合物 |
| GB201720187D0 (en) | 2017-12-04 | 2018-01-17 | Imperial Innovations Ltd | Novel Compounds |
| AU2019205905B2 (en) | 2018-01-03 | 2024-12-12 | Mederis Diabetes, Llc | Improved peptide pharmaceuticals for treatment of NASH and other disorders |
| PE20210473A1 (es) | 2018-05-04 | 2021-03-08 | Novo Nordisk As | Derivados de gip y usos de estos |
| US20200268835A1 (en) | 2019-02-27 | 2020-08-27 | Novo Nordisk A/S | Compounds For Use in NASH |
| GB201908424D0 (en) | 2019-06-12 | 2019-07-24 | Imp College Innovations Ltd | Novel compounds |
| CA3168001A1 (en) * | 2020-02-21 | 2021-08-26 | Spitfire Pharma Llc | Glp-1r and gcgr agonists, formulations, and methods of use |
| CN117202924A (zh) | 2020-12-07 | 2023-12-08 | 斯皮特弗尔制药有限责任公司 | 使用glp-1r和gcgr平衡激动剂降低血糖和/或体重的治疗方案和方法 |
| KR20240118914A (ko) | 2021-01-20 | 2024-08-05 | 바이킹 테라퓨틱스 인코포레이티드 | 대사 및 간 질환 치료를 위한 조성물 및 방법 |
| CA3231953A1 (en) | 2021-09-15 | 2023-03-23 | Brian Lian | Compositions and methods for the treatment of metabolic and liver disorders |
| TW202346323A (zh) | 2022-02-07 | 2023-12-01 | 英商梅迪繆思有限公司 | 具有改善的生物穩定性的ｇｌｐ—１及升糖素雙重激動肽 |
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| WO2011117415A1 (en) * | 2010-03-26 | 2011-09-29 | Novo Nordisk A/S | Novel glucagon analogues |
| WO2011119657A1 (en) * | 2010-03-26 | 2011-09-29 | Eli Lilly And Company | Novel peptides and methods for their preparation and use |
| WO2012088116A2 (en) * | 2010-12-22 | 2012-06-28 | Indiana University Research And Technology Corporation | Glucagon analogs exhibiting gip receptor activity |
| WO2012177444A2 (en) * | 2011-06-22 | 2012-12-27 | Indiana University Research And Technology Corporation | Glucagon/glp-1 receptor co-agonists |
| WO2013041678A1 (en) * | 2011-09-23 | 2013-03-28 | Novo Nordisk A/S | Novel glucagon analogues |
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| US4356170A (en) | 1981-05-27 | 1982-10-26 | Canadian Patents & Development Ltd. | Immunogenic polysaccharide-protein conjugates |
| IL93173A0 (en) | 1989-02-01 | 1990-11-05 | Shionogi & Co | Production of glucagon |
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| US5869602A (en) | 1995-03-17 | 1999-02-09 | Novo Nordisk A/S | Peptide derivatives |
| CZ120398A3 (cs) | 1995-09-08 | 1998-12-16 | Novo Nordisk A/S | Použití 2-alkylpyrrolidinových derivátů pro přípravu léčiva pro léčbu diabetu, 2-alkylpyrrolidiné deriváty |
| CZ220498A3 (cs) | 1996-01-17 | 1998-11-11 | Novo Nordisk A/S | Deriváty 1,2,4-thiadiazinu a 1,4-thiazinu, příprava a použití |
| WO1997041097A2 (en) | 1996-12-31 | 1997-11-06 | Dr. Reddy's Research Foundation | Novel heterocyclic compounds process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases |
| JP2000514041A (ja) | 1996-07-26 | 2000-10-24 | ドクター・レディーズ・リサーチ・ファウンデーション | 抗糖尿病、低脂血、抗高血圧特性を有するチアゾリジンジオン化合物、それらの調製法、及びその薬学的組成物 |
| DE122009000079I2 (de) | 1996-08-30 | 2011-06-16 | Novo Nordisk As Novo Alle | Glp-1 derivate |
| EP0981526B1 (en) | 1997-05-02 | 2004-02-25 | Dr. Reddy's Laboratories Ltd. | Novel antidiabetic compounds having hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them |
| WO1999001423A1 (en) | 1997-07-01 | 1999-01-14 | Novo Nordisk A/S | Glucagon antagonists/inverse agonists |
| US6613942B1 (en) | 1997-07-01 | 2003-09-02 | Novo Nordisk A/S | Glucagon antagonists/inverse agonists |
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Also Published As
| Publication number | Publication date |
|---|---|
| JP2016526012A (ja) | 2016-09-01 |
| AU2014255608A1 (en) | 2015-10-08 |
| PL2986313T3 (pl) | 2019-12-31 |
| MX362275B (es) | 2019-01-10 |
| RU2015146600A (ru) | 2017-05-24 |
| CN105307672B (zh) | 2021-01-05 |
| RU2015146600A3 (enExample) | 2018-03-29 |
| SI2986313T1 (sl) | 2019-09-30 |
| MX2015014408A (es) | 2017-07-28 |
| US9474790B2 (en) | 2016-10-25 |
| US20160355562A1 (en) | 2016-12-08 |
| MY174727A (en) | 2020-05-11 |
| CA2909581A1 (en) | 2014-10-23 |
| WO2014170496A1 (en) | 2014-10-23 |
| EP2986313A1 (en) | 2016-02-24 |
| JP6594856B2 (ja) | 2019-10-23 |
| ZA201507010B (en) | 2017-08-30 |
| KR20160021758A (ko) | 2016-02-26 |
| EP2986313B1 (en) | 2019-06-12 |
| US9751927B2 (en) | 2017-09-05 |
| BR112015025464A2 (pt) | 2017-10-10 |
| US20150374794A1 (en) | 2015-12-31 |
| RU2683039C2 (ru) | 2019-03-26 |
| US20180044394A1 (en) | 2018-02-15 |
| CN105307672A (zh) | 2016-02-03 |
| RS59124B1 (sr) | 2019-09-30 |
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