JP2017517567A5 - - Google Patents
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- Publication number
- JP2017517567A5 JP2017517567A5 JP2017513597A JP2017513597A JP2017517567A5 JP 2017517567 A5 JP2017517567 A5 JP 2017517567A5 JP 2017513597 A JP2017513597 A JP 2017513597A JP 2017513597 A JP2017513597 A JP 2017513597A JP 2017517567 A5 JP2017517567 A5 JP 2017517567A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- independently
- optionally substituted
- aryl
- cycloalkyl
- 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.)
- Granted
Links
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 39
- 125000001072 heteroaryl group Chemical group 0.000 claims 26
- 150000001875 compounds Chemical class 0.000 claims 21
- 125000000217 alkyl group Chemical group 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 239000001257 hydrogen Substances 0.000 claims 20
- 125000000623 heterocyclic group Chemical group 0.000 claims 19
- 125000003118 aryl group Chemical group 0.000 claims 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 16
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 125000001475 halogen functional group Chemical group 0.000 claims 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 6
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 208000035143 Bacterial infection Diseases 0.000 claims 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims 3
- 208000015181 infectious disease Diseases 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
- 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 claims 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- 241000606125 Bacteroides Species 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 229910052796 boron Inorganic materials 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 125000003051 glycosyloxy group Chemical group 0.000 claims 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 230000004962 physiological condition Effects 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 229940002612 prodrug Drugs 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 claims 1
- 241000588626 Acinetobacter baumannii Species 0.000 claims 1
- 241001148231 Acinetobacter haemolyticus Species 0.000 claims 1
- 241000607528 Aeromonas hydrophila Species 0.000 claims 1
- 241000894006 Bacteria Species 0.000 claims 1
- 241001135322 Bacteroides eggerthii Species 0.000 claims 1
- 241000606124 Bacteroides fragilis Species 0.000 claims 1
- 241000606123 Bacteroides thetaiotaomicron Species 0.000 claims 1
- 241000606219 Bacteroides uniformis Species 0.000 claims 1
- 241000606215 Bacteroides vulgatus Species 0.000 claims 1
- 241000588779 Bordetella bronchiseptica Species 0.000 claims 1
- 241000588780 Bordetella parapertussis Species 0.000 claims 1
- 241000588832 Bordetella pertussis Species 0.000 claims 1
- 241000589969 Borreliella burgdorferi Species 0.000 claims 1
- 241000589513 Burkholderia cepacia Species 0.000 claims 1
- 241000589877 Campylobacter coli Species 0.000 claims 1
- 241000589874 Campylobacter fetus Species 0.000 claims 1
- 241000589875 Campylobacter jejuni Species 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- 241000588919 Citrobacter freundii Species 0.000 claims 1
- 241000193163 Clostridioides difficile Species 0.000 claims 1
- 241000186227 Corynebacterium diphtheriae Species 0.000 claims 1
- 241000918600 Corynebacterium ulcerans Species 0.000 claims 1
- 241001600125 Delftia acidovorans Species 0.000 claims 1
- 241000588697 Enterobacter cloacae Species 0.000 claims 1
- 241000194032 Enterococcus faecalis Species 0.000 claims 1
- 241000194031 Enterococcus faecium Species 0.000 claims 1
- 241000588724 Escherichia coli Species 0.000 claims 1
- 241000589602 Francisella tularensis Species 0.000 claims 1
- 241000606788 Haemophilus haemolyticus Species 0.000 claims 1
- 241000606768 Haemophilus influenzae Species 0.000 claims 1
- 241000606822 Haemophilus parahaemolyticus Species 0.000 claims 1
- 241000606766 Haemophilus parainfluenzae Species 0.000 claims 1
- 241000590002 Helicobacter pylori Species 0.000 claims 1
- 241001454354 Kingella Species 0.000 claims 1
- 241000588915 Klebsiella aerogenes Species 0.000 claims 1
- 241000588749 Klebsiella oxytoca Species 0.000 claims 1
- 241000588747 Klebsiella pneumoniae Species 0.000 claims 1
- 241000589242 Legionella pneumophila Species 0.000 claims 1
- 241000186779 Listeria monocytogenes Species 0.000 claims 1
- 241001293418 Mannheimia haemolytica Species 0.000 claims 1
- 241000588621 Moraxella Species 0.000 claims 1
- 241000588655 Moraxella catarrhalis Species 0.000 claims 1
- 241000588772 Morganella morganii Species 0.000 claims 1
- 241000186367 Mycobacterium avium Species 0.000 claims 1
- 241000186364 Mycobacterium intracellulare Species 0.000 claims 1
- 241000186362 Mycobacterium leprae Species 0.000 claims 1
- 241000187479 Mycobacterium tuberculosis Species 0.000 claims 1
- 241000588652 Neisseria gonorrhoeae Species 0.000 claims 1
- 241000588650 Neisseria meningitidis Species 0.000 claims 1
- 241001135232 Odoribacter splanchnicus Species 0.000 claims 1
- 241000606210 Parabacteroides distasonis Species 0.000 claims 1
- 241000588770 Proteus mirabilis Species 0.000 claims 1
- 241000588767 Proteus vulgaris Species 0.000 claims 1
- 241000576783 Providencia alcalifaciens Species 0.000 claims 1
- 241000588777 Providencia rettgeri Species 0.000 claims 1
- 241000588778 Providencia stuartii Species 0.000 claims 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 claims 1
- 241000168225 Pseudomonas alcaligenes Species 0.000 claims 1
- 241000589540 Pseudomonas fluorescens Species 0.000 claims 1
- 241000589776 Pseudomonas putida Species 0.000 claims 1
- 241001354013 Salmonella enterica subsp. enterica serovar Enteritidis Species 0.000 claims 1
- 241000531795 Salmonella enterica subsp. enterica serovar Paratyphi A Species 0.000 claims 1
- 241000293871 Salmonella enterica subsp. enterica serovar Typhi Species 0.000 claims 1
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 claims 1
- 241000607715 Serratia marcescens Species 0.000 claims 1
- 241000607764 Shigella dysenteriae Species 0.000 claims 1
- 241000607762 Shigella flexneri Species 0.000 claims 1
- 241000607760 Shigella sonnei Species 0.000 claims 1
- 241000191967 Staphylococcus aureus Species 0.000 claims 1
- 241000191963 Staphylococcus epidermidis Species 0.000 claims 1
- 241000191984 Staphylococcus haemolyticus Species 0.000 claims 1
- 241000192087 Staphylococcus hominis Species 0.000 claims 1
- 241000191982 Staphylococcus hyicus Species 0.000 claims 1
- 241000191980 Staphylococcus intermedius Species 0.000 claims 1
- 241001464905 Staphylococcus saccharolyticus Species 0.000 claims 1
- 241001147691 Staphylococcus saprophyticus Species 0.000 claims 1
- 241000122973 Stenotrophomonas maltophilia Species 0.000 claims 1
- 241000193985 Streptococcus agalactiae Species 0.000 claims 1
- 241000193998 Streptococcus pneumoniae Species 0.000 claims 1
- 241000193996 Streptococcus pyogenes Species 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 241000607626 Vibrio cholerae Species 0.000 claims 1
- 241000607272 Vibrio parahaemolyticus Species 0.000 claims 1
- 241000607447 Yersinia enterocolitica Species 0.000 claims 1
- 241000607481 Yersinia intermedia Species 0.000 claims 1
- 241000607479 Yersinia pestis Species 0.000 claims 1
- 241000607477 Yersinia pseudotuberculosis Species 0.000 claims 1
- 241000606834 [Haemophilus] ducreyi Species 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical group [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940092559 enterobacter aerogenes Drugs 0.000 claims 1
- 229940032049 enterococcus faecalis Drugs 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229940118764 francisella tularensis Drugs 0.000 claims 1
- 229940047650 haemophilus influenzae Drugs 0.000 claims 1
- 229940037467 helicobacter pylori Drugs 0.000 claims 1
- 229940115932 legionella pneumophila Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229940076266 morganella morganii Drugs 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940007042 proteus vulgaris Drugs 0.000 claims 1
- 229940007046 shigella dysenteriae Drugs 0.000 claims 1
- 229940115939 shigella sonnei Drugs 0.000 claims 1
- 229940037649 staphylococcus haemolyticus Drugs 0.000 claims 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 125000005309 thioalkoxy group Chemical group 0.000 claims 1
- 238000011200 topical administration Methods 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 229940118696 vibrio cholerae Drugs 0.000 claims 1
- 229940098232 yersinia enterocolitica Drugs 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462000980P | 2014-05-20 | 2014-05-20 | |
| US62/000,980 | 2014-05-20 | ||
| US201562142404P | 2015-04-02 | 2015-04-02 | |
| US62/142,404 | 2015-04-02 | ||
| PCT/US2015/031631 WO2015179441A2 (en) | 2014-05-20 | 2015-05-19 | Macrocyclic broad spectrum antibiotics |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021002243A Division JP7148652B2 (ja) | 2014-05-20 | 2021-01-08 | 大環状広域スペクトル抗生物質 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017517567A JP2017517567A (ja) | 2017-06-29 |
| JP2017517567A5 true JP2017517567A5 (https=) | 2018-07-12 |
| JP6823588B2 JP6823588B2 (ja) | 2021-02-03 |
Family
ID=54554959
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017513597A Active JP6823588B2 (ja) | 2014-05-20 | 2015-05-19 | 大環状広域スペクトル抗生物質 |
| JP2021002243A Active JP7148652B2 (ja) | 2014-05-20 | 2021-01-08 | 大環状広域スペクトル抗生物質 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021002243A Active JP7148652B2 (ja) | 2014-05-20 | 2021-01-08 | 大環状広域スペクトル抗生物質 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US10392422B2 (https=) |
| EP (1) | EP3145944B1 (https=) |
| JP (2) | JP6823588B2 (https=) |
| KR (1) | KR20170027721A (https=) |
| CN (1) | CN106661084B (https=) |
| BR (1) | BR112016027232A2 (https=) |
| CA (1) | CA2949681A1 (https=) |
| MX (1) | MX2016015218A (https=) |
| RU (1) | RU2016146581A (https=) |
| WO (1) | WO2015179441A2 (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10501493B2 (en) | 2011-05-27 | 2019-12-10 | Rqx Pharmaceuticals, Inc. | Broad spectrum antibiotics |
| WO2015179441A2 (en) | 2014-05-20 | 2015-11-26 | Rqx Pharmaceuticals, Inc. | Macrocyclic broad spectrum antibiotics |
| US11072635B2 (en) | 2015-11-20 | 2021-07-27 | Rqx Pharmaceuticals, Inc. | Macrocyclic broad spectrum antibiotics |
| TWI725075B (zh) * | 2015-11-20 | 2021-04-21 | 美商Ｒｑｘ製藥公司 | 巨環廣效抗生素 |
| KR20180100570A (ko) * | 2016-01-13 | 2018-09-11 | 제이에스알 가부시끼가이샤 | 감방사선성 수지 조성물, 레지스트 패턴 형성 방법, 산 확산 제어제 및 화합물 |
| WO2017156074A1 (en) * | 2016-03-09 | 2017-09-14 | Blade Therapeutics, Inc. | Calpain modulators and methods of production and use thereof |
| EP3426674A4 (en) | 2016-03-09 | 2019-08-14 | Blade Therapeutics, Inc. | CYCLIC KETO AMID COMPOUNDS AS CALPAIN MODULATORS AND METHOD FOR THE PRODUCTION AND USE THEREOF |
| AU2017292646A1 (en) | 2016-07-05 | 2019-02-07 | Blade Therapeutics, Inc. | Calpain modulators and therapeutic uses thereof |
| WO2018064119A1 (en) | 2016-09-28 | 2018-04-05 | Blade Therapeutics, Inc. | Calpain modulators and therapeutic uses thereof |
| EP3330260A1 (en) | 2016-12-01 | 2018-06-06 | Enantia, S.L. | Process for the preparation of an intermediate for the synthesis of i.a. carfilzomib |
| AU2018222093B2 (en) * | 2017-02-15 | 2022-03-31 | Genentech, Inc. | Macrocyclic broad spectrum antibiotics |
| EP3600333A4 (en) | 2017-03-21 | 2020-11-25 | The Scripps Research Institute | CU AND NI-CATALYZED DECARBOXYLATIVE BORYLATION REACTIONS |
| CN106966947B (zh) * | 2017-03-30 | 2019-09-03 | 河北医科大学 | 一种维格列汀的制备方法 |
| KR20250086794A (ko) * | 2017-12-15 | 2025-06-13 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 치환된 방향족 아민 |
| CN108806787B (zh) * | 2018-07-06 | 2022-04-05 | 上海长海医院 | 面向临床手术的医用耗材智能监控系统 |
| CN109355404B (zh) * | 2018-08-30 | 2022-03-29 | 华南理工大学 | 基于聚合酶螺旋反应恒温检测单增李斯特菌的引物、试剂盒及检测方法 |
| EP3852786A4 (en) * | 2018-09-19 | 2022-09-28 | Georgia Tech Research Corporation | SELF-TITRATEING BACTERIAL PROTEASE-ACTIVATED PRODRUG |
| JP7078807B2 (ja) | 2019-05-28 | 2022-05-31 | エフ．ホフマン－ラ ロシュ アーゲー | 大環状広域スペクトル抗生物質 |
| CN118063337B (zh) * | 2024-02-19 | 2025-01-28 | 绵阳师范学院 | 一种(s)-3-氨基-2-戊酮盐酸盐的制备方法 |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3128280A (en) | 1959-10-23 | 1964-04-07 | Searle & Co | 1-(alkoxylated/halogenated phenyl)-3-pyridylmethylureas |
| US5204328A (en) | 1990-06-26 | 1993-04-20 | Merck & Co., Inc. | Peptides having atrial natriuretic factor activity |
| EP0895999A1 (en) | 1997-08-06 | 1999-02-10 | Pfizer Products Inc. | C-4" substituted macrolide antibiotics |
| GB9902399D0 (en) | 1999-02-03 | 1999-03-24 | Smithkline Beecham Plc | Compounds |
| US6660832B1 (en) | 1999-08-20 | 2003-12-09 | Isis Pharmaceuticals, Inc. | Macrocyclic compounds and preparation methods thereof |
| US6951840B2 (en) | 2001-08-31 | 2005-10-04 | Eli Lilly And Company | Lipoglycopeptide antibiotics |
| DE10226921A1 (de) | 2002-06-17 | 2003-12-24 | Bayer Ag | Antibakterielle Amid-Makrozyklen |
| CN1839150A (zh) | 2003-07-17 | 2006-09-27 | 麦根克斯有限公司 | 脂肽抗菌衍生物组合物及其应用方法 |
| DE10358824A1 (de) * | 2003-12-16 | 2005-07-21 | Bayer Healthcare Ag | Antibakterielle Makrozyklen mit substituiertem Biphenyl |
| DE102005014247A1 (de) | 2005-03-30 | 2006-10-05 | Aicuris Gmbh & Co. Kg | Antibakterielle Amid-Makrozyklen VI |
| DE102005014245A1 (de) | 2005-03-30 | 2006-10-05 | Aicuris Gmbh & Co. Kg | Antibakterielle Amid-Makrozyklen V |
| AU2011223790A1 (en) | 2010-03-01 | 2012-08-30 | Myrexis, Inc. | Compounds and therapeutic uses thereof |
| CN102939095A (zh) * | 2010-03-09 | 2013-02-20 | 默沙东公司 | 增强β-内酰胺抗菌药物的活性的桥联脂糖肽类 |
| WO2011120071A1 (en) | 2010-04-01 | 2011-10-06 | The University Of Queensland | Oxytocin peptide analogues |
| BR112013006265A2 (pt) | 2010-09-15 | 2016-06-07 | Scripps Research Inst | espectros antibióticos gerais análogos a arilomicina |
| US10501493B2 (en) | 2011-05-27 | 2019-12-10 | Rqx Pharmaceuticals, Inc. | Broad spectrum antibiotics |
| TWI642684B (zh) | 2011-05-27 | 2018-12-01 | Ｒｑｘ製藥股份有限公司 | 廣效性抗生素 |
| CA2867448A1 (en) | 2012-03-14 | 2013-09-19 | Floyd E. Romesberg | Broad spectrum antibiotic arylomycin analogs |
| CN103788176A (zh) | 2012-10-31 | 2014-05-14 | 上海来益生物药物研究开发中心有限责任公司 | 一种arylomycin类化合物及其制备方法和应用 |
| KR20150088292A (ko) | 2012-11-21 | 2015-07-31 | 알큐엑스 파마슈티컬스, 인크. | 광범위한 마크로사이클릭 항생제 |
| WO2015179441A2 (en) | 2014-05-20 | 2015-11-26 | Rqx Pharmaceuticals, Inc. | Macrocyclic broad spectrum antibiotics |
| ITUB20154591A1 (it) | 2015-10-12 | 2017-04-12 | Crestoptics S R L | Apparato di microscopia confocale e relativo procedimento di acquisizione ed elaborazione di immagini |
| US11072635B2 (en) | 2015-11-20 | 2021-07-27 | Rqx Pharmaceuticals, Inc. | Macrocyclic broad spectrum antibiotics |
| TWI725075B (zh) | 2015-11-20 | 2021-04-21 | 美商Ｒｑｘ製藥公司 | 巨環廣效抗生素 |
-
2015
- 2015-05-19 WO PCT/US2015/031631 patent/WO2015179441A2/en not_active Ceased
- 2015-05-19 RU RU2016146581A patent/RU2016146581A/ru not_active Application Discontinuation
- 2015-05-19 JP JP2017513597A patent/JP6823588B2/ja active Active
- 2015-05-19 EP EP15795762.2A patent/EP3145944B1/en active Active
- 2015-05-19 MX MX2016015218A patent/MX2016015218A/es unknown
- 2015-05-19 CN CN201580039532.9A patent/CN106661084B/zh active Active
- 2015-05-19 US US15/312,614 patent/US10392422B2/en active Active
- 2015-05-19 KR KR1020167035448A patent/KR20170027721A/ko not_active Withdrawn
- 2015-05-19 CA CA2949681A patent/CA2949681A1/en not_active Abandoned
- 2015-05-19 BR BR112016027232A patent/BR112016027232A2/pt not_active Application Discontinuation
-
2021
- 2021-01-08 JP JP2021002243A patent/JP7148652B2/ja active Active
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