IL269210B2 - Indole derivatives as efflux pump inhibitors - Google Patents
Indole derivatives as efflux pump inhibitorsInfo
- Publication number
- IL269210B2 IL269210B2 IL269210A IL26921019A IL269210B2 IL 269210 B2 IL269210 B2 IL 269210B2 IL 269210 A IL269210 A IL 269210A IL 26921019 A IL26921019 A IL 26921019A IL 269210 B2 IL269210 B2 IL 269210B2
- Authority
- IL
- Israel
- Prior art keywords
- alkyl
- mmol
- compound
- carbocyclyl
- hydrogen
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762469987P | 2017-03-10 | 2017-03-10 | |
| US201762523154P | 2017-06-21 | 2017-06-21 | |
| PCT/US2018/021848 WO2018165611A1 (en) | 2017-03-10 | 2018-03-09 | Indole derivatives as efflux pump inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| IL269210A IL269210A (en) | 2019-11-28 |
| IL269210B1 IL269210B1 (en) | 2025-01-01 |
| IL269210B2 true IL269210B2 (en) | 2025-05-01 |
Family
ID=62044950
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL269210A IL269210B2 (en) | 2017-03-10 | 2018-03-09 | Indole derivatives as efflux pump inhibitors |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US11993571B2 (https=) |
| EP (1) | EP3592736A1 (https=) |
| JP (1) | JP7323179B2 (https=) |
| KR (1) | KR102697360B1 (https=) |
| CN (1) | CN110770224B (https=) |
| AU (1) | AU2018231120B2 (https=) |
| BR (1) | BR112019018691A2 (https=) |
| CA (1) | CA3061238A1 (https=) |
| IL (1) | IL269210B2 (https=) |
| MX (1) | MX2019010717A (https=) |
| SG (1) | SG11201908351TA (https=) |
| WO (1) | WO2018165611A1 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10836706B2 (en) | 2016-02-24 | 2020-11-17 | Rutgers, The State University Of New Jersey | Bacterial efflux pump inhibitors |
| US10556854B2 (en) | 2016-02-24 | 2020-02-11 | Rutgers, The State University Of New Jersey | Bacterial efflux pump inhibitors |
| US11938114B2 (en) | 2017-03-10 | 2024-03-26 | Rutgers, The State University Of New Jersey | Bacterial efflux pump inhibitors |
| WO2018165612A1 (en) | 2017-03-10 | 2018-09-13 | Rutgers, The State University Of New Jersey | Bacterial efflux pump inhibitors |
| CN110770224B (zh) | 2017-03-10 | 2022-11-18 | 罗格斯新泽西州立大学 | 作为外排泵抑制剂的吲哚衍生物 |
| EP3630109A4 (en) | 2017-05-26 | 2021-03-17 | Rutgers, the State University of New Jersey | BACTERIAL EFFLUX PUMP INHIBITORS |
| WO2019005841A1 (en) | 2017-06-26 | 2019-01-03 | Rutgers, The State University Of New Jersey | THERAPEUTIC COMPOUNDS AND METHODS FOR TREATING INFECTION |
| US11845742B2 (en) | 2017-11-14 | 2023-12-19 | Rutgers, The State University Of New Jersey | Therapeutic compounds and methods to treat infection |
| KR102704123B1 (ko) | 2019-11-01 | 2024-09-06 | 에스엘 주식회사 | 차량용 램프 |
| AU2024327693A1 (en) | 2023-08-23 | 2026-04-02 | Taxis Pharmaceuticals, Inc. | Bacterial efflux pump inhibitors |
| TW202525791A (zh) * | 2023-08-29 | 2025-07-01 | 美商梅斯治療股份有限公司 | 溶質載體家族6a成員19(slc6a19)之抑制劑及其使用方法 |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3465080A (en) * | 1968-10-07 | 1969-09-02 | American Cyanamid Co | Therapeutic compositions containing morpholinoalkylene - indoles and methods of administering such in the treatment of depression |
| WO2003028725A1 (en) * | 2001-09-28 | 2003-04-10 | Richter Gedeon Vegyészeti Gyár Rt. | 4-(1-piperidiny)-butylcarboxamide as d3 dopamine receptor subtype selective ligands |
| US6730684B1 (en) * | 1999-10-08 | 2004-05-04 | Affinium Pharmaceuticals, Inc. | Fab I inhibitors |
| US20090215828A1 (en) * | 2008-02-22 | 2009-08-27 | Grunenthal Gmbh | Substituted indole derivatives |
| WO2012084971A1 (fr) * | 2010-12-20 | 2012-06-28 | Centre National De La Recherche Scientifique (Cnrs) | Derives d'indoles en tant qu'agents contre des bacteries a gram negatif et positif |
| WO2014078294A1 (en) * | 2012-11-13 | 2014-05-22 | Memorial Sloan-Kettering Cancer Center | Indole compounds and their use as antimicrobials |
| WO2015164482A1 (en) * | 2014-04-22 | 2015-10-29 | The Johns Hopkins University | Inhibitors of drug-resistant mycobacterium tuberculosis |
| US20200155507A1 (en) * | 2017-06-26 | 2020-05-21 | Edmond Lavoie | Therapeutic compounds and methods to treat infection |
Family Cites Families (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3238215A (en) * | 1963-10-17 | 1966-03-01 | Sterling Drug Inc | 1-[(3-, 2-, and 1-indolyl)-lower-alkyl-, lower-alkenyl-, and lower-alkynyl]piperidines |
| US3978224A (en) | 1975-07-01 | 1976-08-31 | Schering Corporation | Antimicrobial halo-substituted-2-cyanoethylaminoalkyl-3-phenyl-indoles |
| US4910193A (en) * | 1985-12-16 | 1990-03-20 | Sandoz Ltd. | Treatment of gastrointestinal disorders |
| US4938949A (en) | 1988-09-12 | 1990-07-03 | University Of New York | Treatment of damaged bone marrow and dosage units therefor |
| WO1992004017A1 (en) | 1990-09-10 | 1992-03-19 | The Upjohn Company | Cis-n-(2-aminocyclohexyl)benzamide and their enantiomers as anticonvulsants |
| US5864039A (en) * | 1994-03-30 | 1999-01-26 | Yoshitomi Pharmaceutical Industries, Ltd. | Benzoic acid compounds and use thereof as medicaments |
| US5663152A (en) | 1995-01-19 | 1997-09-02 | Asahi Kasei Kogyo Kabushiki Kaisha | Potentiators for aminoglycosides |
| US6506339B1 (en) * | 1997-02-10 | 2003-01-14 | Biomedical Design, Inc. | Method of sterilization |
| AU2337599A (en) * | 1998-01-23 | 1999-08-09 | Microcide Pharmaceuticals, Inc. | Efflux pump inhibitors |
| US6204279B1 (en) | 1998-06-03 | 2001-03-20 | Microcide Pharmaceuticals, Inc. | Peptidomimetic efflux pump inhibitors |
| CA2353557A1 (en) | 1998-12-04 | 2000-06-08 | Influx, Inc. | Inhibitors of multidrug transporters |
| CO5251397A1 (es) | 1999-10-08 | 2003-02-28 | Smithkline Beecham Corp | Inhibidores de fab i |
| US6555569B2 (en) | 2000-03-07 | 2003-04-29 | Pfizer Inc. | Use of heteroaryl substituted N-(indole-2-carbonyl-) amides for treatment of infection |
| US7365205B2 (en) * | 2001-06-20 | 2008-04-29 | Daiichi Sankyo Company, Limited | Diamine derivatives |
| EP1314733A1 (en) * | 2001-11-22 | 2003-05-28 | Aventis Pharma Deutschland GmbH | Indole-2-carboxamides as factor Xa inhibitors |
| US7829543B2 (en) | 2003-01-07 | 2010-11-09 | Paratek Pharmaceuticals, Inc. | Substituted polyamines as inhibitors of bacterial efflux pumps |
| GB0403038D0 (en) * | 2004-02-11 | 2004-03-17 | Novartis Ag | Organic compounds |
| US7994225B2 (en) | 2004-03-17 | 2011-08-09 | Rempex Pharmaceuticals, Inc. | Bacterial efflux pump inhibitors for the treatment of ophthalmic and otic infections |
| WO2005113579A1 (en) | 2004-05-21 | 2005-12-01 | Mpex Pharmaceuticals, Inc. | Bacterial efflux pump inhibitors and methods of treating bacterial infections |
| US8143257B2 (en) | 2004-11-23 | 2012-03-27 | Ptc Therapeutics, Inc. | Substituted phenols as active agents inhibiting VEGF production |
| US7855228B2 (en) | 2005-02-10 | 2010-12-21 | The Board Of Trustees Of The Leland Stamford Junior University | Antibiotics targeting MreB |
| US7807704B2 (en) | 2006-03-30 | 2010-10-05 | Chemocentryx, Inc. | Bicyclic, nitrogen-containing compounds modulating CXCR4 and/or CCXCKR2 |
| FR2904317A1 (fr) * | 2006-07-27 | 2008-02-01 | Inst Nat Sante Rech Med | Analogues d'halogenobenzamides marques a titre de radiopharmaceutiques |
| EP3192788A1 (en) | 2006-10-03 | 2017-07-19 | Arbutus Biopharma Corporation | Lipid containing formulations |
| WO2009110002A1 (en) | 2008-03-05 | 2009-09-11 | Council Of Scientific & Industrial Research | Novel efflux pump inhibitors |
| CA2737038A1 (en) | 2008-09-18 | 2010-03-25 | Evotec Ag | Amide compounds, compositions and uses thereof |
| EA201101451A1 (ru) | 2009-04-03 | 2012-03-30 | Ачиллион Фармасьютикалз, Инк. | Гидрокситиенохинолоны и родственные соединения как противоинфекционные средства |
| EP2536408A1 (en) | 2010-02-16 | 2012-12-26 | Wockhardt Research Centre | Efflux pump inhibitors |
| EP2394653A1 (en) * | 2010-05-26 | 2011-12-14 | Almirall, S.A. | Topical pharmaceutical compositions comprising mometasone furoate |
| BR112015004666B1 (pt) | 2012-09-07 | 2022-04-26 | Novartis Ag | Derivados de indol carboxamida, seu uso, e composição farmacêutica |
| WO2016040505A1 (en) * | 2014-09-10 | 2016-03-17 | Epizyme, Inc. | Smyd inhibitors |
| US9926261B2 (en) | 2015-03-10 | 2018-03-27 | Rutgers, The State University Of New Jersey | Bacterial efflux pump inhibitors |
| US9950993B2 (en) | 2015-03-13 | 2018-04-24 | Rutgers, The State University Of New Jersey | Bacterial efflux pump inhibitors |
| KR20180011843A (ko) | 2015-06-11 | 2018-02-02 | 바실리어 파마슈티카 인터내셔널 리미티드 | 유출-펌프 억제제 및 이의 치료적 용도 |
| WO2017023894A1 (en) * | 2015-08-03 | 2017-02-09 | Raze Therapeutics, Inc. | Mthfd2 inhibitors and uses thereof |
| US10836706B2 (en) | 2016-02-24 | 2020-11-17 | Rutgers, The State University Of New Jersey | Bacterial efflux pump inhibitors |
| US10556854B2 (en) | 2016-02-24 | 2020-02-11 | Rutgers, The State University Of New Jersey | Bacterial efflux pump inhibitors |
| ES2968227T3 (es) * | 2016-12-23 | 2024-05-08 | Aquinnah Pharmaceuticals Inc | Compuestos, composiciones y procedimientos de uso |
| CN110770224B (zh) | 2017-03-10 | 2022-11-18 | 罗格斯新泽西州立大学 | 作为外排泵抑制剂的吲哚衍生物 |
| US11938114B2 (en) | 2017-03-10 | 2024-03-26 | Rutgers, The State University Of New Jersey | Bacterial efflux pump inhibitors |
| WO2018165612A1 (en) | 2017-03-10 | 2018-09-13 | Rutgers, The State University Of New Jersey | Bacterial efflux pump inhibitors |
| EP3630109A4 (en) | 2017-05-26 | 2021-03-17 | Rutgers, the State University of New Jersey | BACTERIAL EFFLUX PUMP INHIBITORS |
| US20190031624A1 (en) | 2017-07-28 | 2019-01-31 | Rutgers, The State University Of New Jersey | Therapeutic compounds and methods to treat infection |
| US11845742B2 (en) * | 2017-11-14 | 2023-12-19 | Rutgers, The State University Of New Jersey | Therapeutic compounds and methods to treat infection |
-
2018
- 2018-03-09 CN CN201880030845.1A patent/CN110770224B/zh active Active
- 2018-03-09 BR BR112019018691-3A patent/BR112019018691A2/pt active Search and Examination
- 2018-03-09 WO PCT/US2018/021848 patent/WO2018165611A1/en not_active Ceased
- 2018-03-09 AU AU2018231120A patent/AU2018231120B2/en active Active
- 2018-03-09 KR KR1020197029528A patent/KR102697360B1/ko active Active
- 2018-03-09 MX MX2019010717A patent/MX2019010717A/es unknown
- 2018-03-09 SG SG11201908351T patent/SG11201908351TA/en unknown
- 2018-03-09 EP EP18719686.0A patent/EP3592736A1/en active Pending
- 2018-03-09 US US16/492,901 patent/US11993571B2/en active Active
- 2018-03-09 JP JP2019549454A patent/JP7323179B2/ja active Active
- 2018-03-09 CA CA3061238A patent/CA3061238A1/en active Pending
- 2018-03-09 IL IL269210A patent/IL269210B2/en unknown
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3465080A (en) * | 1968-10-07 | 1969-09-02 | American Cyanamid Co | Therapeutic compositions containing morpholinoalkylene - indoles and methods of administering such in the treatment of depression |
| US6730684B1 (en) * | 1999-10-08 | 2004-05-04 | Affinium Pharmaceuticals, Inc. | Fab I inhibitors |
| WO2003028725A1 (en) * | 2001-09-28 | 2003-04-10 | Richter Gedeon Vegyészeti Gyár Rt. | 4-(1-piperidiny)-butylcarboxamide as d3 dopamine receptor subtype selective ligands |
| US20090215828A1 (en) * | 2008-02-22 | 2009-08-27 | Grunenthal Gmbh | Substituted indole derivatives |
| WO2012084971A1 (fr) * | 2010-12-20 | 2012-06-28 | Centre National De La Recherche Scientifique (Cnrs) | Derives d'indoles en tant qu'agents contre des bacteries a gram negatif et positif |
| WO2014078294A1 (en) * | 2012-11-13 | 2014-05-22 | Memorial Sloan-Kettering Cancer Center | Indole compounds and their use as antimicrobials |
| WO2015164482A1 (en) * | 2014-04-22 | 2015-10-29 | The Johns Hopkins University | Inhibitors of drug-resistant mycobacterium tuberculosis |
| US20200155507A1 (en) * | 2017-06-26 | 2020-05-21 | Edmond Lavoie | Therapeutic compounds and methods to treat infection |
Non-Patent Citations (1)
| Title |
|---|
| MEYER, BRIAN K., ET AL., ANTIMICROBIAL PRESERVATIVE USE IN PARENTERAL PRODUCTS: PAST AND PRESENT., 31 December 2007 (2007-12-31) * |
Also Published As
| Publication number | Publication date |
|---|---|
| IL269210A (en) | 2019-11-28 |
| US20210094912A1 (en) | 2021-04-01 |
| CA3061238A1 (en) | 2018-09-13 |
| EP3592736A1 (en) | 2020-01-15 |
| AU2018231120A1 (en) | 2019-10-31 |
| SG11201908351TA (en) | 2019-10-30 |
| IL269210B1 (en) | 2025-01-01 |
| JP7323179B2 (ja) | 2023-08-08 |
| JP2020510044A (ja) | 2020-04-02 |
| WO2018165611A1 (en) | 2018-09-13 |
| CN110770224A (zh) | 2020-02-07 |
| AU2018231120B2 (en) | 2022-06-23 |
| KR102697360B1 (ko) | 2024-08-20 |
| MX2019010717A (es) | 2019-12-05 |
| BR112019018691A2 (pt) | 2020-04-07 |
| KR20190138790A (ko) | 2019-12-16 |
| US11993571B2 (en) | 2024-05-28 |
| CN110770224B (zh) | 2022-11-18 |
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