JP2017522357A5 - - Google Patents
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- JP2017522357A5 JP2017522357A5 JP2017505480A JP2017505480A JP2017522357A5 JP 2017522357 A5 JP2017522357 A5 JP 2017522357A5 JP 2017505480 A JP2017505480 A JP 2017505480A JP 2017505480 A JP2017505480 A JP 2017505480A JP 2017522357 A5 JP2017522357 A5 JP 2017522357A5
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- Prior art keywords
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- 150000001875 compounds Chemical class 0.000 claims 94
- 238000000034 method Methods 0.000 claims 37
- 238000004519 manufacturing process Methods 0.000 claims 20
- 239000000203 mixture Substances 0.000 claims 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 12
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 9
- 239000012442 inert solvent Substances 0.000 claims 8
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 5
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 5
- 230000003197 catalytic effect Effects 0.000 claims 5
- 238000005580 one pot reaction Methods 0.000 claims 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- 238000010992 reflux Methods 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 238000003756 stirring Methods 0.000 claims 4
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 claims 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 3
- 229960000583 acetic acid Drugs 0.000 claims 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 239000012362 glacial acetic acid Substances 0.000 claims 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 0 C*c1c(C=C(C(C)=O)C(OCCC#N)=O)ccc(C#N)c1 Chemical compound C*c1c(C=C(C(C)=O)C(OCCC#N)=O)ccc(C#N)c1 0.000 description 1
- RFJLQSVKIAMLCX-NTEUORMPSA-N CC(/C(/C(OCCC#N)=O)=C\c(ccc(C#N)c1)c1OC)=O Chemical compound CC(/C(/C(OCCC#N)=O)=C\c(ccc(C#N)c1)c1OC)=O RFJLQSVKIAMLCX-NTEUORMPSA-N 0.000 description 1
- WWAABAWXHRNWCT-UHFFFAOYSA-N CC(C(C(I)=O)C(OC)=C1)C=C1[Zn] Chemical compound CC(C(C(I)=O)C(OC)=C1)C=C1[Zn] WWAABAWXHRNWCT-UHFFFAOYSA-N 0.000 description 1
- SMWPNASNQIIBDW-UHFFFAOYSA-N CC(C1=C2C(c(ccc(N)c3)c3OC)C(C(OCCN)=O)=C(C)N1)=CNC2=O Chemical compound CC(C1=C2C(c(ccc(N)c3)c3OC)C(C(OCCN)=O)=C(C)N1)=CNC2=O SMWPNASNQIIBDW-UHFFFAOYSA-N 0.000 description 1
- WUPRJMHPZJWLHY-YYBBLCMGSA-N CCOc1ncc(C)c2c1[C@H](C(/C(/OC)=C\C(\C#N)=C/C)=C)C(C(N)=O)=C(C)N2 Chemical compound CCOc1ncc(C)c2c1[C@H](C(/C(/OC)=C\C(\C#N)=C/C)=C)C(C(N)=O)=C(C)N2 WUPRJMHPZJWLHY-YYBBLCMGSA-N 0.000 description 1
- ZXENVSJZOHXCKL-UHFFFAOYSA-N COc1c(C=O)ccc(C#N)c1 Chemical compound COc1c(C=O)ccc(C#N)c1 ZXENVSJZOHXCKL-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14179544.3 | 2014-08-01 | ||
| EP14179544 | 2014-08-01 | ||
| PCT/EP2015/067340 WO2016016287A1 (de) | 2014-08-01 | 2015-07-29 | Verfahren zur herstellung von (4s)- 4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridin-3-carbox-amid und dessen aufreinigung für die verwendung als pharmazeutischer wirkstoff |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017522357A JP2017522357A (ja) | 2017-08-10 |
| JP2017522357A5 true JP2017522357A5 (show.php) | 2018-09-06 |
| JP6818674B2 JP6818674B2 (ja) | 2021-01-20 |
Family
ID=51260727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017505480A Active JP6818674B2 (ja) | 2014-08-01 | 2015-07-29 | （４ｓ）−４−（４−シアノ−２−メトキシフェニル）−５−エトキシ−２，８−ジメチル−１，４−ジヒドロ−１，６−ナフチリジン−３−カルボキサミドを調製するための方法および医薬品有効成分としての使用のためのその精製 |
Country Status (31)
| Country | Link |
|---|---|
| US (4) | US10059707B2 (show.php) |
| EP (2) | EP3660015A1 (show.php) |
| JP (1) | JP6818674B2 (show.php) |
| KR (3) | KR102527893B1 (show.php) |
| CN (4) | CN116655627A (show.php) |
| AR (1) | AR101403A1 (show.php) |
| AU (1) | AU2015295376C1 (show.php) |
| BR (1) | BR112017001678B1 (show.php) |
| CA (2) | CA2956529A1 (show.php) |
| CL (1) | CL2017000263A1 (show.php) |
| CO (1) | CO2017000886A2 (show.php) |
| DK (1) | DK3174875T3 (show.php) |
| ES (1) | ES2828704T3 (show.php) |
| HR (1) | HRP20201800T1 (show.php) |
| HU (1) | HUE051350T2 (show.php) |
| IL (1) | IL250239B (show.php) |
| JO (1) | JO3648B1 (show.php) |
| LT (1) | LT3174875T (show.php) |
| MX (1) | MX369467B (show.php) |
| MY (1) | MY198066A (show.php) |
| PE (1) | PE20170141A1 (show.php) |
| PL (1) | PL3174875T3 (show.php) |
| PT (1) | PT3174875T (show.php) |
| RS (1) | RS60921B1 (show.php) |
| RU (1) | RU2729998C9 (show.php) |
| SG (1) | SG11201700785UA (show.php) |
| SI (1) | SI3174875T1 (show.php) |
| TW (1) | TWI684593B (show.php) |
| UA (1) | UA122773C2 (show.php) |
| UY (1) | UY36251A (show.php) |
| WO (1) | WO2016016287A1 (show.php) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RS60921B1 (sr) * | 2014-08-01 | 2020-11-30 | Bayer Pharma AG | Postupak za dobijanje (4s)-4-(4-cijano-2-metoksifenil)-5-etoksi-2,8-dimetil-1,4-dihidro-1-6-naftiridin-3-karboksamida i njegovo prečišćavanje za upotrebu kao aktivnog farmaceutskog sastojka |
| PT3337800T (pt) | 2015-08-21 | 2019-08-05 | Bayer Pharma AG | Método para a preparação de (4s)-4-(4-ciano-2-metoxi fenil)-5-etoxi-2,8-dimetil-1,4-di-hidro-1-6-naftiridina-3- carboxamida e purificação do mesmo para a utilização como ingrediente farmacêutico ativo |
| EP3560922A1 (de) | 2018-04-24 | 2019-10-30 | Bayer Aktiengesellschaft | Verfahren zur herstellung von (4s)- 4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridin-3-carbox-amid durch racemat-spaltung mittels diastereomerer weinsäureester |
| SG11202109546RA (en) | 2019-03-05 | 2021-09-29 | Bayer Ag | Synthesis of 4-amino-5-methyl-1h-pyridin-2(1h)-on (intermediate compound for the synthesis of the mr antagonist finerenone) from 2-chloro-5-methyl-4-nitro-pyridine-1-oxide using the intermediate compound 2-chloro-5-methyl-4-pyridinamine |
| US12152006B2 (en) | 2019-03-05 | 2024-11-26 | Bayer Aktiengesellschaft | Process for preparing 4-amino-5-methylpyridone |
| JP7757278B2 (ja) | 2019-10-17 | 2025-10-21 | バイエル アクチェンゲゼルシャフト | （４ｓ）－（４－シアノ－２－メトキシフェニル）－５－エトキシ－２，８－ジメチル－１，４－ジヒドロ－１，６－ナフチリジン－３－カルボン酸のアシルオキシメチルエステルの製造方法 |
| WO2021074072A1 (de) * | 2019-10-17 | 2021-04-22 | Bayer Aktiengesellschaft | Verfahren zur herstellung von 2-cyanoethyl (4s)-4-(4-cyano-2-methoxy-phenyl)-5-hydroxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridin-3-carboxylat durch racemat-spaltung mittels diastereomerer weinsäureester |
| AU2020367978A1 (en) * | 2019-10-17 | 2022-05-12 | Bayer Aktiengesellschaft | Process for the preparation of 2-cyanoethyl (4S)-4-(4-cyano-2-methoxy-phenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxylate by resolution of racemates by means of diastereomeric tartaric acid esters |
| CR20220158A (es) * | 2019-10-17 | 2022-06-15 | Bayer Ag | Procedimiento fotoquímico para la preparación de (4r,4s)–4–(4–ciano–2–metoxifenil)–5–etoxi–2,8–dimetil–1,4–dihidro–1,6–naftiridin–3–carboxamida |
| EP3900722A1 (en) | 2020-04-22 | 2021-10-27 | Bayer AG | Combination of finerenone and pecavaptan for the treatment and/or prevention of cardiovascular and/or renal diseases |
| EP4138826A1 (en) | 2020-04-22 | 2023-03-01 | Bayer Aktiengesellschaft | Combination of finerenone and a sglt2 inhibitor for the treatment and/or prevention of cardiovascular and/or renal diseases |
| TW202214624A (zh) | 2020-06-16 | 2022-04-16 | 德商拜耳廠股份有限公司 | 藉由催化不對稱漢斯（ｈａｎｔｚｓｃｈ）酯還原法進行之製備（４ｓ）－４－（４－氰基－２－甲氧基苯基）－５－乙氧基－２，８－二甲基－１，４－二氫－１，６－㖠啶－３－羧醯胺的方法 |
| CN112237573B (zh) * | 2020-10-29 | 2023-12-22 | 瑞阳制药股份有限公司 | 含finerenone的片剂及其制备方法 |
| WO2022214206A1 (en) | 2021-04-08 | 2022-10-13 | Bayer Aktiengesellschaft | Combination of finerenone and pecavaptan for the treatment and/or prevention of cardiovascular and/or renal diseases |
| CN114149427A (zh) * | 2021-12-18 | 2022-03-08 | 上海鼎雅药物化学科技有限公司 | 非奈利酮及其中间体的合成方法 |
| CN115340539B (zh) | 2022-01-19 | 2024-02-27 | 奥锐特药业股份有限公司 | 制备非奈利酮及其中间体的方法 |
| CN115340540A (zh) * | 2022-01-20 | 2022-11-15 | 奥锐特药业股份有限公司 | 制备非奈利酮及其中间体的方法 |
| CN114524812A (zh) * | 2022-03-18 | 2022-05-24 | 湖南凯铂生物药业有限公司 | 1,4-二氢-1,6-萘啶化合物的晶型制备以及合成方法 |
| WO2023205164A1 (en) | 2022-04-18 | 2023-10-26 | Teva Pharmaceuticals International Gmbh | Processes for the preparation of finerenone |
| EP4286368A1 (de) | 2022-05-31 | 2023-12-06 | Bayer Aktiengesellschaft | Verfahren zur herstellung von 4-formyl-3-methoxybenzonitril |
| WO2024075139A1 (en) * | 2022-10-06 | 2024-04-11 | Maithri Drugs Private Limited | A process for preparation of finerenone and intermediates thereof |
| CN117986250A (zh) | 2022-11-04 | 2024-05-07 | 南京威凯尔生物医药科技有限公司 | 通过非对映酒石酸酯拆分外消旋体制备非奈利酮的方法 |
| EP4622646A1 (en) | 2022-11-23 | 2025-10-01 | Bayer Aktiengesellschaft | Treatment of chronic kidney disease in type i diabetes mellitus |
| KR20250121106A (ko) | 2022-12-16 | 2025-08-11 | 바이엘 악티엔게젤샤프트 | 4-(4-시아노-2-메톡시페닐)-5-에톡시-2,8-디메틸-1,4-디히드로-1,6-나프티리딘-3-카르복스아미드의제조를 위한 순차적 원-포트 합성 |
| WO2024147053A1 (en) * | 2023-01-03 | 2024-07-11 | Optimus Drugs Pvt Ltd | Improved process for the preparation of finerenone |
| EP4682147A1 (en) * | 2023-03-17 | 2026-01-21 | Jiangsu Hengrui Pharmaceuticals Co., Ltd. | Pharmaceutically acceptable salt and crystal form of 1,4-dihydro-1,6-naphthyridine amide compound and preparation method therefor |
| WO2025104752A1 (en) * | 2023-11-18 | 2025-05-22 | Msn Laboratories Private Limited, R&D Center | Improved process for the preparation of (4s)4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide |
| CN120081840A (zh) * | 2023-12-01 | 2025-06-03 | 山东诚创蓝海医药科技有限公司 | 一种非奈利酮-马来酸共晶及其制备方法 |
| US20250313559A1 (en) | 2024-01-05 | 2025-10-09 | Bayer Aktiengesellschaft | Method of preventing or treating heart failure in a patient using (4s)-4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide |
| WO2025247801A1 (en) * | 2024-05-30 | 2025-12-04 | Bayer Aktiengesellschaft | Determination of a dosage of a nonsteroidal mineralocorticoid receptor antagonist |
| CN119462643A (zh) * | 2024-10-17 | 2025-02-18 | 河北国龙制药有限公司 | 一种非奈利酮单晶及其制备方法和应用 |
| CN119019395A (zh) * | 2024-10-29 | 2024-11-26 | 成都诺和晟欣生物医药有限公司 | 一种非奈利酮晶型ⅰ的制备方法 |
| CN119684289A (zh) * | 2024-12-18 | 2025-03-25 | 安徽先和医药研究有限公司 | 一种非奈利酮的制备方法 |
| CN119684288A (zh) * | 2024-12-18 | 2025-03-25 | 安徽先和医药研究有限公司 | 非奈利酮的制备方法 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL75987A (en) * | 1984-08-25 | 1991-07-18 | Goedecke Ag | Tri-and tetrasubstituted-1,4-dihydro-1,6-naphthyridine-3-carboxylic acid derivatives,their preparation and pharmaceutical compositions containing them |
| US4895860A (en) * | 1989-04-21 | 1990-01-23 | American Home Products Corporation | Novel substituted 3H-1,2,3,5-oxathiadiazole 2-oxides useful as anthihyperglycemic agents |
| DE19834047A1 (de) | 1998-07-29 | 2000-02-03 | Bayer Ag | Substituierte Pyrazolderivate |
| DE19834044A1 (de) | 1998-07-29 | 2000-02-03 | Bayer Ag | Neue substituierte Pyrazolderivate |
| GB9914825D0 (en) | 1999-06-24 | 1999-08-25 | Smithkline Beecham Spa | Novel compounds |
| DE19943635A1 (de) | 1999-09-13 | 2001-03-15 | Bayer Ag | Neuartige Aminodicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| DE19943634A1 (de) | 1999-09-13 | 2001-04-12 | Bayer Ag | Neuartige Dicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| DE19943636A1 (de) | 1999-09-13 | 2001-03-15 | Bayer Ag | Neuartige Dicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| DE19943639A1 (de) | 1999-09-13 | 2001-03-15 | Bayer Ag | Dicarbonsäurederivate mit neuartigen pharmazeutischen Eigenschaften |
| AR031176A1 (es) | 2000-11-22 | 2003-09-10 | Bayer Ag | Nuevos derivados de pirazolpiridina sustituidos con piridina |
| DE10110750A1 (de) | 2001-03-07 | 2002-09-12 | Bayer Ag | Neuartige Aminodicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| DE10110749A1 (de) | 2001-03-07 | 2002-09-12 | Bayer Ag | Substituierte Aminodicarbonsäurederivate |
| DE10220570A1 (de) | 2002-05-08 | 2003-11-20 | Bayer Ag | Carbamat-substituierte Pyrazolopyridine |
| WO2006044775A2 (en) * | 2004-10-15 | 2006-04-27 | Bayer Pharmaceuticals Corporation | Preparation and use of biphenyl-4-yl-carbonylamino acid derivatives for the treatment of obesity |
| WO2006060461A1 (en) * | 2004-12-03 | 2006-06-08 | Schering Corporation | Substituted piperazines as cb1 antagonists |
| AU2006201739A1 (en) * | 2005-05-05 | 2006-11-23 | The University Of North Carolina At Chapel Hill | Synthesis and antiprotozoal activity of dicationic 3,5-diphenylisoxazoles |
| EP1902022A1 (en) | 2005-07-12 | 2008-03-26 | Glaxo Group Limited | Piperazine heteroaryl derivates as gpr38 agonists |
| DE102006026583A1 (de) | 2006-06-07 | 2007-12-13 | Bayer Healthcare Aktiengesellschaft | Aryl-substituierte hetero-bicyclische Verbindungen und ihre Verwendung |
| DE102006044696A1 (de) | 2006-09-22 | 2008-03-27 | Bayer Healthcare Ag | 3-Cyano-5-thiazaheteroaryl-dihydropyridine und ihre Verwendung |
| DE102007009494A1 (de) | 2007-02-27 | 2008-08-28 | Bayer Healthcare Ag | Substituierte 4-Aryl-1, 4-dihydro-1,6-naphthyridinamide und ihre Verwendung |
| CN102020587A (zh) | 2010-11-25 | 2011-04-20 | 大连凯飞精细化工有限公司 | 2-甲氧基-4-氰基苯甲醛的合成方法 |
| RS60921B1 (sr) * | 2014-08-01 | 2020-11-30 | Bayer Pharma AG | Postupak za dobijanje (4s)-4-(4-cijano-2-metoksifenil)-5-etoksi-2,8-dimetil-1,4-dihidro-1-6-naftiridin-3-karboksamida i njegovo prečišćavanje za upotrebu kao aktivnog farmaceutskog sastojka |
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2015
- 2015-07-29 RS RS20201213A patent/RS60921B1/sr unknown
- 2015-07-29 KR KR1020177005278A patent/KR102527893B1/ko active Active
- 2015-07-29 PL PL15742306T patent/PL3174875T3/pl unknown
- 2015-07-29 UA UAA201701875A patent/UA122773C2/uk unknown
- 2015-07-29 EP EP19213735.4A patent/EP3660015A1/de not_active Withdrawn
- 2015-07-29 CA CA2956529A patent/CA2956529A1/en active Pending
- 2015-07-29 JP JP2017505480A patent/JP6818674B2/ja active Active
- 2015-07-29 CN CN202310616268.7A patent/CN116655627A/zh active Pending
- 2015-07-29 CN CN201580053456.7A patent/CN106795155B/zh active Active
- 2015-07-29 HU HUE15742306A patent/HUE051350T2/hu unknown
- 2015-07-29 RU RU2017106602A patent/RU2729998C9/ru active
- 2015-07-29 US US15/329,043 patent/US10059707B2/en not_active Ceased
- 2015-07-29 LT LTEP15742306.2T patent/LT3174875T/lt unknown
- 2015-07-29 CA CA3146285A patent/CA3146285C/en active Active
- 2015-07-29 BR BR112017001678-8A patent/BR112017001678B1/pt active IP Right Grant
- 2015-07-29 SG SG11201700785UA patent/SG11201700785UA/en unknown
- 2015-07-29 DK DK15742306.2T patent/DK3174875T3/da active
- 2015-07-29 MX MX2017001507A patent/MX369467B/es active IP Right Grant
- 2015-07-29 KR KR1020237014295A patent/KR102830206B1/ko active Active
- 2015-07-29 EP EP15742306.2A patent/EP3174875B1/de active Active
- 2015-07-29 HR HRP20201800TT patent/HRP20201800T1/hr unknown
- 2015-07-29 US US17/002,115 patent/USRE49575E1/en active Active
- 2015-07-29 KR KR1020257022052A patent/KR20250108757A/ko active Pending
- 2015-07-29 AU AU2015295376A patent/AU2015295376C1/en active Active
- 2015-07-29 ES ES15742306T patent/ES2828704T3/es active Active
- 2015-07-29 MY MYPI2017700334A patent/MY198066A/en unknown
- 2015-07-29 CN CN202310620718.XA patent/CN116655630B/zh active Active
- 2015-07-29 PE PE2017000143A patent/PE20170141A1/es unknown
- 2015-07-29 SI SI201531406T patent/SI3174875T1/sl unknown
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