RU2020108634A - Аналоги карбамоилфенилаланинола и способы их применения - Google Patents
Аналоги карбамоилфенилаланинола и способы их применения Download PDFInfo
- Publication number
- RU2020108634A RU2020108634A RU2020108634A RU2020108634A RU2020108634A RU 2020108634 A RU2020108634 A RU 2020108634A RU 2020108634 A RU2020108634 A RU 2020108634A RU 2020108634 A RU2020108634 A RU 2020108634A RU 2020108634 A RU2020108634 A RU 2020108634A
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- Russia
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- optionally substituted
- compound
- pharmaceutically acceptable
- compound according
- acceptable salt
- Prior art date
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- NJVZDURTFWBXAM-VIFPVBQESA-N [(2S)-1-hydroxy-3-phenylpropan-2-yl]urea Chemical class C(N)(=O)N[C@@H](CC1=CC=CC=C1)CO NJVZDURTFWBXAM-VIFPVBQESA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 23
- 150000003839 salts Chemical class 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 5
- 206010041349 Somnolence Diseases 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 4
- 208000007590 Disorders of Excessive Somnolence Diseases 0.000 claims 3
- 208000016588 Idiopathic hypersomnia Diseases 0.000 claims 3
- 208000001797 obstructive sleep apnea Diseases 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- 208000001573 Cataplexy Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 208000025748 atypical depressive disease Diseases 0.000 claims 2
- 239000002775 capsule Substances 0.000 claims 2
- -1 cyano, hydroxy Chemical group 0.000 claims 2
- 150000001923 cyclic compounds Chemical class 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 239000002552 dosage form Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 239000012729 immediate-release (IR) formulation Substances 0.000 claims 2
- 201000003631 narcolepsy Diseases 0.000 claims 2
- 239000006186 oral dosage form Substances 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 125000005309 thioalkoxy group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical group N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 208000001640 Fibromyalgia Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000005793 Restless legs syndrome Diseases 0.000 claims 1
- 201000001880 Sexual dysfunction Diseases 0.000 claims 1
- 208000032140 Sleepiness Diseases 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- 208000014679 binge eating disease Diseases 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229940125904 compound 1 Drugs 0.000 claims 1
- 229940125782 compound 2 Drugs 0.000 claims 1
- 229940126214 compound 3 Drugs 0.000 claims 1
- 229940125898 compound 5 Drugs 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 206010013663 drug dependence Diseases 0.000 claims 1
- 206010016256 fatigue Diseases 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 231100000872 sexual dysfunction Toxicity 0.000 claims 1
- 230000037321 sleepiness Effects 0.000 claims 1
- 230000005586 smoking cessation Effects 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
Classifications
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- 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
-
- 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
- A61K31/325—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
- C07C275/18—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
- 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 |
|---|---|
| RU2020108634A true RU2020108634A (ru) | 2021-09-02 |
| RU2020108634A3 RU2020108634A3 (https=) | 2021-11-30 |
Family
ID=65233074
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2020108634A RU2020108634A (ru) | 2017-07-31 | 2018-07-31 | Аналоги карбамоилфенилаланинола и способы их применения |
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 |
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| 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 |
| AU4674797A (en) * | 1996-10-22 | 1998-05-15 | Ortho Pharmaceutical Corporation | Phenylalaninol derivatives for the treatment of central nervous system disorders |
| 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 |
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| 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. |
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| 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 |
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| 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 |
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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
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| 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 |
| KR102643275B1 (ko) | 2024-03-04 |
| CN111094238B (zh) | 2023-06-09 |
| MX2023005484A (es) | 2023-05-18 |
| MX2020001146A (es) | 2020-08-20 |
| US20250017890A1 (en) | 2025-01-16 |
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