KR102643275B1 - 카바모일 페닐알라니놀 유사체 및 이의 용도 - Google Patents
카바모일 페닐알라니놀 유사체 및 이의 용도 Download PDFInfo
- Publication number
- KR102643275B1 KR102643275B1 KR1020207005652A KR20207005652A KR102643275B1 KR 102643275 B1 KR102643275 B1 KR 102643275B1 KR 1020207005652 A KR1020207005652 A KR 1020207005652A KR 20207005652 A KR20207005652 A KR 20207005652A KR 102643275 B1 KR102643275 B1 KR 102643275B1
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- KR
- South Korea
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- pharmaceutically acceptable
- acceptable salt
- disorder
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/18—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of a saturated carbon skeleton containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/255—Esters, e.g. nitroglycerine, selenocyanates of sulfoxy acids or sulfur analogues thereof
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
-
- 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
- A61K31/325—Carbamic acids; Thiocarbamic acids; Anhydrides or salts thereof
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/11—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/20—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C275/24—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C307/02—Monoamides of sulfuric acids or esters thereof, e.g. sulfamic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/02—Monothiocarbamic acids; Derivatives thereof
- C07C333/04—Monothiocarbamic acids; Derivatives thereof having nitrogen atoms of thiocarbamic groups bound to hydrogen atoms or to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762539088P | 2017-07-31 | 2017-07-31 | |
| US62/539,088 | 2017-07-31 | ||
| PCT/US2018/044465 WO2019027941A1 (en) | 2017-07-31 | 2018-07-31 | CARBAMOYL PHENYLALANINOL ANALOGUES AND USES THEREOF |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20200045489A KR20200045489A (ko) | 2020-05-04 |
| KR102643275B1 true KR102643275B1 (ko) | 2024-03-04 |
Family
ID=65233074
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020207005652A Active KR102643275B1 (ko) | 2017-07-31 | 2018-07-31 | 카바모일 페닐알라니놀 유사체 및 이의 용도 |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US11413264B2 (https=) |
| EP (1) | EP3661911A4 (https=) |
| JP (2) | JP7366002B2 (https=) |
| KR (1) | KR102643275B1 (https=) |
| CN (1) | CN111094238B (https=) |
| AU (1) | AU2018312328B2 (https=) |
| CA (1) | CA3071779A1 (https=) |
| MX (2) | MX2020001146A (https=) |
| RU (1) | RU2020108634A (https=) |
| SA (1) | SA520411187B1 (https=) |
| SG (1) | SG11202000817SA (https=) |
| WO (1) | WO2019027941A1 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11602512B1 (en) | 2016-07-22 | 2023-03-14 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US12478604B1 (en) | 2016-07-22 | 2025-11-25 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11504347B1 (en) | 2016-07-22 | 2022-11-22 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11602513B1 (en) | 2016-07-22 | 2023-03-14 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US12186296B1 (en) | 2016-07-22 | 2025-01-07 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| UY37341A (es) | 2016-07-22 | 2017-11-30 | Flamel Ireland Ltd | Formulaciones de gamma-hidroxibutirato de liberación modificada con farmacocinética mejorada |
| US11986451B1 (en) | 2016-07-22 | 2024-05-21 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| JP7366002B2 (ja) * | 2017-07-31 | 2023-10-20 | ジャズ ファーマシューティカルズ アイルランド リミテッド | カルバモイルフェニルアラニノール類縁体およびその使用 |
| CN113473980A (zh) | 2019-03-01 | 2021-10-01 | 弗拉梅尔爱尔兰有限公司 | 在进食状态下具有改善的药代动力学的γ-羟基丁酸酯组合物 |
| US11779557B1 (en) | 2022-02-07 | 2023-10-10 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11583510B1 (en) | 2022-02-07 | 2023-02-21 | Flamel Ireland Limited | Methods of administering gamma hydroxybutyrate formulations after a high-fat meal |
| WO2023235844A2 (en) * | 2022-06-03 | 2023-12-07 | Axsome Therapeutics | Carbamoyl phenylalaninol compounds as taar1 agonists |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998017636A1 (en) * | 1996-10-22 | 1998-04-30 | Ortho Pharmaceutical Corporation | Phenylalaninol derivatives for the treatment of central nervous system disorders |
| CN101823987A (zh) * | 2009-03-06 | 2010-09-08 | 中国科学院上海药物研究所 | 一类新的dpp-ⅳ抑制剂及其制备方法和用途 |
| CN102249833A (zh) * | 2011-05-27 | 2011-11-23 | 中国科学院化学研究所 | 一种制备手性γ-氨基酸及其衍生物的方法 |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2604434B1 (fr) | 1986-09-29 | 1989-05-19 | Inst Nat Sante Rech Med | Derives d'amino-2 ethanethiol, leur preparation et leur application en therapeutique |
| KR100197892B1 (ko) | 1994-09-09 | 1999-06-15 | 남창우 | 신규한 페닐알킬아미노 카바메이트 화합물과 그의 제조방법 |
| US5756817C1 (en) | 1995-02-11 | 2001-04-17 | Sk Corp | O-carbamoyl-phenylananinol compounds their pharmaceutically useful salts and process for preparing the same |
| KR0173862B1 (ko) | 1995-02-11 | 1999-04-01 | 조규향 | O-카바모일-(d)-페닐알라닌올 화합물과 그의 약제학적으로 유용한 염 및 이들의 제조방법 |
| KR0173863B1 (ko) | 1995-04-10 | 1999-04-01 | 조규향 | 페닐에 치환체가 있는 o-카바모일-페닐알라닌올 화합물과 그의 약제학적으로 유용한 염 및 이들의 제조방법 |
| DK0873308T3 (da) * | 1996-10-10 | 2002-04-22 | Sk Corp | O-Carbamoyl-phenylalaninol-forbindelser og deres farmaceutisk anvendelige salte |
| US5935997A (en) * | 1998-01-13 | 1999-08-10 | Yukong Limited | O-thiocarbamoyl-aminoalkanol compounds, their pharmaceutically useful salts and process for preparing the same |
| DK1140061T3 (da) | 1998-12-23 | 2003-08-25 | Orphan Medical Inc | Mikrobiologisk sunde og stabile opløsninger af gamma-hydroxybutyratsalt til behandling af narcolepsi |
| KR100440643B1 (ko) * | 1999-01-28 | 2004-07-21 | 쥬가이 세이야쿠 가부시키가이샤 | 치환 페네틸아민 유도체 |
| ES2209384T3 (es) * | 1999-02-05 | 2004-06-16 | Sk Corporation | Compuestos de o-tiocarbamoilaminoalcanol, sus sales farmaceuticamente aceptables y proceso para preparar los mismos. |
| WO2000064865A1 (en) * | 1999-04-23 | 2000-11-02 | Solvay Pharmaceuticals B.V. | Monomers and oligourea peptidomimetics and process for the prepa ration thereof |
| US6680322B2 (en) | 1999-12-02 | 2004-01-20 | Osi Pharmaceuticals, Inc. | Compounds specific to adenosine A1 receptors and uses thereof |
| US6680324B2 (en) | 2000-12-01 | 2004-01-20 | Osi Pharmaceuticals, Inc. | Compounds specific to adenosine A1 receptors and uses thereof |
| EP1264814A1 (en) * | 2001-06-08 | 2002-12-11 | Avantium International B.V. | Resolving agents based on amines |
| US6680299B2 (en) | 2001-07-27 | 2004-01-20 | Enanta Pharmaceuticals, Inc. | 4'-substituted leucomycins |
| KR100576372B1 (ko) * | 2001-08-03 | 2006-05-03 | 에스케이 주식회사 | Ｏ-티오카바모일-아미노알카놀 화합물, 이의 약학적 허용염 및 제조방법 |
| ITFI20030113A1 (it) * | 2003-04-24 | 2004-10-25 | Menarini Ricerche Spa | Composti lineari nk-2 antagonisti con caratteristiche basiche e formulazioni che li contengono. |
| RU2007119648A (ru) | 2004-10-28 | 2008-12-10 | СК Холдингз Ко. | Способ лечения депрессии |
| EP1890684B1 (en) * | 2005-06-08 | 2013-08-14 | SK Biopharmaceuticals Co., Ltd. | Treatment of sleep-wake disorders |
| ES2344469T3 (es) | 2005-06-22 | 2010-08-27 | Sk Holdings Co., Ltd. | Tratamiento de disfuncion sexual. |
| KR20120098578A (ko) | 2009-06-22 | 2012-09-05 | 에스케이바이오팜 주식회사 | 피로의 치료 또는 예방 방법 |
| US8232315B2 (en) | 2009-06-26 | 2012-07-31 | Sk Biopharmaceuticals Co., Ltd. | Methods for treating drug addiction and improving addiction-related behavior |
| EP2496227B1 (en) | 2009-11-06 | 2019-05-22 | SK Biopharmaceuticals Co., Ltd. | Methods for treating fibromyalgia syndrome |
| BR112012010670A2 (pt) | 2009-11-06 | 2016-04-12 | Sk Biopharmaceuticals Co Ltd | métodos para tratamento de distúrbio de défict de atenção/hiperatividade |
| US8623913B2 (en) | 2010-06-30 | 2014-01-07 | Sk Biopharmaceuticals Co., Ltd. | Methods for treating restless legs syndrome |
| US9610274B2 (en) | 2010-06-30 | 2017-04-04 | Sk Biopharmaceuticals Co., Ltd. | Methods for treating bipolar disorder |
| US9050302B2 (en) | 2013-03-01 | 2015-06-09 | Jazz Pharmaceuticals Ireland Limited | Method of administration of gamma hydroxybutyrate with monocarboxylate transporters |
| CA2905457A1 (en) | 2013-03-13 | 2014-10-09 | Aerial Biopharma, Llc | Treatment of cataplexy |
| JP2016530240A (ja) | 2013-07-12 | 2016-09-29 | ジャズ ファーマスティカルズ インターナショナル スリー リミテッドＪａｚｚ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｉｉｉ Ｌｉｍｉｔｅｄ | 禁煙の促進 |
| CA2917702A1 (en) | 2013-07-18 | 2015-01-22 | Jazz Pharmaceuticals International Iii Limited | Treatment for obesity |
| US10702498B2 (en) * | 2015-07-09 | 2020-07-07 | The Regents Of The University Of California | MU opioid receptor modulators |
| US10195151B2 (en) | 2016-09-06 | 2019-02-05 | Jazz Pharmaceuticals International Iii Limited | Formulations of (R)-2-amino-3-phenylpropyl carbamate |
| ES2964943T3 (es) | 2016-10-06 | 2024-04-10 | Axsome Malta Ltd | Compuestos de carbamoilfenilalaninol para uso médico |
| JP7366002B2 (ja) * | 2017-07-31 | 2023-10-20 | ジャズ ファーマシューティカルズ アイルランド リミテッド | カルバモイルフェニルアラニノール類縁体およびその使用 |
-
2018
- 2018-07-31 JP JP2020505344A patent/JP7366002B2/ja active Active
- 2018-07-31 US US16/634,935 patent/US11413264B2/en active Active
- 2018-07-31 KR KR1020207005652A patent/KR102643275B1/ko active Active
- 2018-07-31 MX MX2020001146A patent/MX2020001146A/es unknown
- 2018-07-31 WO PCT/US2018/044465 patent/WO2019027941A1/en not_active Ceased
- 2018-07-31 CA CA3071779A patent/CA3071779A1/en active Pending
- 2018-07-31 CN CN201880059970.5A patent/CN111094238B/zh active Active
- 2018-07-31 RU RU2020108634A patent/RU2020108634A/ru unknown
- 2018-07-31 EP EP18840981.7A patent/EP3661911A4/en active Pending
- 2018-07-31 SG SG11202000817SA patent/SG11202000817SA/en unknown
- 2018-07-31 AU AU2018312328A patent/AU2018312328B2/en active Active
-
2020
- 2020-01-29 SA SA520411187A patent/SA520411187B1/ar unknown
- 2020-01-29 MX MX2023005484A patent/MX2023005484A/es unknown
-
2022
- 2022-06-16 US US17/841,976 patent/US20220401401A1/en not_active Abandoned
-
2023
- 2023-04-26 JP JP2023072520A patent/JP7642707B2/ja active Active
-
2024
- 2024-09-30 US US18/901,040 patent/US20250017890A1/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998017636A1 (en) * | 1996-10-22 | 1998-04-30 | Ortho Pharmaceutical Corporation | Phenylalaninol derivatives for the treatment of central nervous system disorders |
| CN101823987A (zh) * | 2009-03-06 | 2010-09-08 | 中国科学院上海药物研究所 | 一类新的dpp-ⅳ抑制剂及其制备方法和用途 |
| CN102249833A (zh) * | 2011-05-27 | 2011-11-23 | 中国科学院化学研究所 | 一种制备手性γ-氨基酸及其衍生物的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| NZ762140A (en) | 2024-11-29 |
| SG11202000817SA (en) | 2020-02-27 |
| AU2018312328A1 (en) | 2020-03-19 |
| JP2023100758A (ja) | 2023-07-19 |
| CA3071779A1 (en) | 2019-02-07 |
| JP7642707B2 (ja) | 2025-03-10 |
| EP3661911A4 (en) | 2021-04-14 |
| US20210093603A1 (en) | 2021-04-01 |
| EP3661911A1 (en) | 2020-06-10 |
| JP2020530837A (ja) | 2020-10-29 |
| JP7366002B2 (ja) | 2023-10-20 |
| US20220401401A1 (en) | 2022-12-22 |
| WO2019027941A1 (en) | 2019-02-07 |
| KR20200045489A (ko) | 2020-05-04 |
| AU2018312328B2 (en) | 2022-12-15 |
| US11413264B2 (en) | 2022-08-16 |
| RU2020108634A3 (https=) | 2021-11-30 |
| SA520411187B1 (ar) | 2024-10-17 |
| CN111094238A (zh) | 2020-05-01 |
| CN111094238B (zh) | 2023-06-09 |
| RU2020108634A (ru) | 2021-09-02 |
| MX2023005484A (es) | 2023-05-18 |
| MX2020001146A (es) | 2020-08-20 |
| US20250017890A1 (en) | 2025-01-16 |
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