JP7702654B2 - トリプタミンプロドラッグ - Google Patents
トリプタミンプロドラッグ Download PDFInfo
- Publication number
- JP7702654B2 JP7702654B2 JP2022580938A JP2022580938A JP7702654B2 JP 7702654 B2 JP7702654 B2 JP 7702654B2 JP 2022580938 A JP2022580938 A JP 2022580938A JP 2022580938 A JP2022580938 A JP 2022580938A JP 7702654 B2 JP7702654 B2 JP 7702654B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- compounds
- compound
- depression
- drug
- 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.)
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Classifications
-
- 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
- A61K31/4045—Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/02—Inorganic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/08—Solutions
-
- 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
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Dermatology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Nutrition Science (AREA)
- Physiology (AREA)
- Hospice & Palliative Care (AREA)
- Inorganic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2025094025A JP2025143280A (ja) | 2020-06-30 | 2025-06-05 | トリプタミンプロドラッグ |
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US202063045901P | 2020-06-30 | 2020-06-30 | |
| US63/045,901 | 2020-06-30 | ||
| US202063109095P | 2020-11-03 | 2020-11-03 | |
| US63/109,095 | 2020-11-03 | ||
| US17/364,047 US11292765B2 (en) | 2020-06-30 | 2021-06-30 | Tryptamine prodrugs |
| US17/364,047 | 2021-06-30 | ||
| PCT/CA2021/050907 WO2022000091A1 (en) | 2020-06-30 | 2021-06-30 | Tryptamine prodrugs |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2025094025A Division JP2025143280A (ja) | 2020-06-30 | 2025-06-05 | トリプタミンプロドラッグ |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| JP2023531311A JP2023531311A (ja) | 2023-07-21 |
| JP2023531311A5 JP2023531311A5 (https=) | 2024-07-09 |
| JPWO2022000091A5 JPWO2022000091A5 (https=) | 2024-07-09 |
| JP7702654B2 true JP7702654B2 (ja) | 2025-07-04 |
Family
ID=79032374
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022580938A Active JP7702654B2 (ja) | 2020-06-30 | 2021-06-30 | トリプタミンプロドラッグ |
| JP2025094025A Pending JP2025143280A (ja) | 2020-06-30 | 2025-06-05 | トリプタミンプロドラッグ |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2025094025A Pending JP2025143280A (ja) | 2020-06-30 | 2025-06-05 | トリプタミンプロドラッグ |
Country Status (10)
| Country | Link |
|---|---|
| US (4) | US11292765B2 (https=) |
| EP (1) | EP4172145A4 (https=) |
| JP (2) | JP7702654B2 (https=) |
| KR (2) | KR20250103811A (https=) |
| CN (3) | CN115867533B (https=) |
| AU (1) | AU2021302692A1 (https=) |
| CA (1) | CA3181092A1 (https=) |
| IL (2) | IL299506B2 (https=) |
| MX (1) | MX2022016212A (https=) |
| WO (1) | WO2022000091A1 (https=) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114787363A (zh) | 2019-10-01 | 2022-07-22 | 恩派瑞安神经科学公司 | 对真菌进行遗传工程化以调节色胺表达 |
| MX2022009528A (es) | 2020-02-04 | 2022-11-14 | Mindset Pharma Inc | Derivados de 3-pirrolidina-indol como agentes psicodélicos serotoninérgicos para el tratamiento de trastornos del snc. |
| PH12022551981A1 (en) | 2020-02-04 | 2023-10-16 | Mindset Pharma Inc | Psilocin derivatives as serotonergic psychedelic agents for the treatment of cns disorders |
| AU2021268204A1 (en) | 2020-05-08 | 2022-12-08 | Psilera Inc. | Novel compositions of matter and pharmaceutical compositions |
| CN115867533B (zh) * | 2020-06-30 | 2024-07-23 | 加拿大瑞安神经科学公司 | 色胺前药 |
| WO2022040802A1 (en) * | 2020-08-26 | 2022-03-03 | Magicmed Industries Inc. | Glycosylated psilocybin derivatives and methods of using |
| WO2022120181A1 (en) * | 2020-12-03 | 2022-06-09 | Mydecine Innovations Group Inc. | Novel psilocin analog compositions and methods of synthesizing the same |
| EP4263504A4 (en) * | 2020-12-18 | 2025-05-14 | COMPASS Pathfinder Limited | Modified indole alkaloids for therapeutic uses |
| US12534441B2 (en) | 2021-01-15 | 2026-01-27 | Beckley Psytech Limited | Tryptamine analogues |
| EP4126857A1 (en) | 2021-01-15 | 2023-02-08 | Beckley Psytech Limited | Ergoline analogues |
| US11312684B1 (en) | 2021-02-10 | 2022-04-26 | Eleusis Therapeutics Us, Inc. | Pharmaceutically acceptable salts of psilocin and uses thereof |
| BR112023025599A2 (pt) | 2021-06-08 | 2024-02-20 | Entheogenix Biosciences Inc | Ativadores de dimetoxifenilalquilamina de receptores de serotonina. |
| CA3225133A1 (en) | 2021-07-07 | 2023-01-12 | Matthew Alexander James Duncton | N,n-dimethyltryptamine and related psychedlics and uses thereof |
| WO2023018864A1 (en) | 2021-08-12 | 2023-02-16 | Psilosterics, Llc | Hallucinogenic and non-hallucinogenic serotonin receptor agonists and methods of making and using the same |
| WO2023023347A1 (en) * | 2021-08-20 | 2023-02-23 | Terran Biosciences Inc. | Prodrugs and derivatives of psilocin and uses thereof |
| EP4429672A4 (en) | 2021-11-12 | 2025-04-30 | Terran Biosciences Inc. | PSILOCYBIN AND O-ACETYLPSILOCIN, SALTS AND SOLID FORMS THEREOF |
| US12404238B2 (en) | 2021-12-10 | 2025-09-02 | Caamtech, Inc. | Psilocybin derivatives |
| JP2024546138A (ja) * | 2021-12-14 | 2024-12-17 | レユニオン ニューロサイエンス,インコーポレイテッド | トリプタミンプロドラッグ |
| EP4457203A4 (en) | 2021-12-27 | 2025-12-17 | Atai Therapeutics Inc | AMINOTETRALINE ACTIVATORS OF SEROTONIN RECEPTORS |
| JP2024545787A (ja) | 2021-12-30 | 2024-12-11 | アタイ セラピューティクス, インコーポレイテッド | 一酸化窒素送達剤としてのジメチルトリプタミン類似体 |
| EP4457336A4 (en) | 2021-12-31 | 2026-01-14 | Empyrean Neuroscience Inc | ORGANISMS GENETICALLY MODIFIED TO PRODUCE PSYCHOTROPIC ALKALOIDS |
| WO2023133477A1 (en) * | 2022-01-06 | 2023-07-13 | Terran Biosciences, Inc. | Salts and solid forms of 4-hydroxy-n,n-diisopropyltryptamine hemi-glutarate and hemi-succinate |
| WO2023147423A1 (en) * | 2022-01-28 | 2023-08-03 | Miralogx Llc | Anxiolytic compounds, pharmaceutical compositions, and methods of treating anxiety and other disorders |
| WO2023168023A1 (en) | 2022-03-04 | 2023-09-07 | Reset Pharmaceuticals, Inc. | Co-crystals or salts comprising psilocin |
| US20250186369A1 (en) * | 2022-03-07 | 2025-06-12 | Drexel University | Compounds, compositions, and methods for treating, ameliorating, and/or prventing cocaine use disorder |
| US12065404B2 (en) | 2022-03-18 | 2024-08-20 | Enveric Biosciences Canada Inc. | C4-carboxylic acid-substituted tryptamine derivatives and methods of using |
| EP4493542A4 (en) * | 2022-03-18 | 2026-03-04 | Enveric Biosciences Canada Inc | C4-CARBONOTHIOATE SUBSTITUTED TRYPTAMINE DERIVATIVES AND METHODS OF USE |
| AU2022446955A1 (en) * | 2022-03-18 | 2024-11-07 | Enveric Biosciences Canada Inc. | C4-carboxylic acid-substituted tryptamine derivatives and methods of using |
| EP4493544A4 (en) * | 2022-03-18 | 2026-03-04 | Enveric Biosciences Canada Inc | TRYPTAMINE DERIVATIVE SALTS SUBSTITUTED WITH C4-CARBOXYLIC ACID AND C4-CARBONOTHIOATE AND METHODS OF USE |
| WO2023201293A2 (en) * | 2022-04-13 | 2023-10-19 | Caamtech, Inc. | Tryptamine derivatives |
| CN115521240B (zh) * | 2022-06-01 | 2024-05-28 | 杭州奥泰生物技术股份有限公司 | 一种二甲基色胺半抗原和人工抗原及其制备方法与应用 |
| EP4561527A2 (en) * | 2022-07-27 | 2025-06-04 | Reconnect Labs AG | Highly soluble formulations of harmine |
| US12264131B2 (en) | 2022-08-19 | 2025-04-01 | Beckley Psytech Limited | Pharmaceutically acceptable salts and compositions thereof |
| CN116283885B (zh) * | 2022-12-01 | 2025-02-14 | 杭州奥泰生物技术股份有限公司 | 一种帕罗西汀半抗原和人工抗原及其制备方法与应用 |
| JP2026501775A (ja) * | 2023-01-05 | 2026-01-16 | リユニオン・ニューロサイエンス、インコーポレイテッド | トリプタミンプロドラッグの薬物動態の改善 |
| WO2024178051A2 (en) * | 2023-02-22 | 2024-08-29 | Caamtech, Inc. | Tryptamine derivatives |
| EP4704822A1 (en) | 2023-05-01 | 2026-03-11 | ATAI Therapeutics, Inc. | Compositions and methods for treatment of diseases and disorders |
| US12246005B2 (en) | 2023-06-13 | 2025-03-11 | Beckley Psytech Limited | 5-methoxy-n,n-dimethyltryptamine (5-MeO-DMT) formulations |
| WO2025099725A1 (en) * | 2023-11-09 | 2025-05-15 | Hadasit Medical Research Services And Development Ltd. | Conjugates and uses thereof |
| WO2025238416A1 (en) * | 2024-05-16 | 2025-11-20 | Mindset Pharma Inc. | Indole derivatives, uses and compositions thereof |
| WO2025250900A1 (en) * | 2024-05-30 | 2025-12-04 | Caamtech, Inc. | 4-hydroxy-n,n-diisopropyltryptaminium hydroglutarate |
| WO2026024591A1 (en) * | 2024-07-22 | 2026-01-29 | Reunion Neuroscience, Inc. | Tryptamine prodrug solid forms |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3075992A (en) | 1958-09-12 | 1963-01-29 | Sandoz Ltd | Esters of indoles |
| WO1995006638A1 (en) | 1993-09-01 | 1995-03-09 | Allelix Biopharmaceuticals Inc. | Tryptamine analogs with 5-ht1d selectivity |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL243249A (https=) | 1958-09-12 | |||
| CH373381A (de) | 1959-07-13 | 1963-11-30 | Sandoz Ag | Verfahren zur Herstellung neuer basischer Indol-Derivate |
| CH386422A (de) | 1960-03-30 | 1965-01-15 | Sandoz Ag | Verfahren zur Herstellung neuer Ester der Indol-Reihe |
| KR0166088B1 (ko) | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
| US5376645A (en) | 1990-01-23 | 1994-12-27 | University Of Kansas | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof |
| GB9711643D0 (en) | 1997-06-05 | 1997-07-30 | Janssen Pharmaceutica Nv | Glass thermoplastic systems |
| AU2005300045A1 (en) * | 2004-09-27 | 2006-05-04 | Organix, Inc. | Indole compounds useful as serotonin selective agents |
| PL2352497T3 (pl) | 2008-10-31 | 2017-08-31 | University Of Mississippi | Proces przygotowania estrów aminokwasowych delta-9-thc |
| US20180021326A1 (en) | 2016-07-23 | 2018-01-25 | Paul Edward Stamets | Compositions and methods for enhancing neuroregeneration and cognition by combining mushroom extracts containing active ingredients psilocin or psilocybin with erinacines or hericenones enhanced with niacin |
| EP4219498A1 (en) * | 2019-03-07 | 2023-08-02 | Arbormentis LLC | Compositions and methods of use comprising substances with neural plasticity actions administered at non-psychedelic / psychotomimetic dosages and formulations |
| PH12022551981A1 (en) | 2020-02-04 | 2023-10-16 | Mindset Pharma Inc | Psilocin derivatives as serotonergic psychedelic agents for the treatment of cns disorders |
| CN115867533B (zh) * | 2020-06-30 | 2024-07-23 | 加拿大瑞安神经科学公司 | 色胺前药 |
| EP4263504A4 (en) * | 2020-12-18 | 2025-05-14 | COMPASS Pathfinder Limited | Modified indole alkaloids for therapeutic uses |
-
2021
- 2021-06-30 CN CN202180046999.1A patent/CN115867533B/zh active Active
- 2021-06-30 CN CN202410898893.XA patent/CN119285526A/zh active Pending
- 2021-06-30 CN CN202410898937.9A patent/CN119285527A/zh active Pending
- 2021-06-30 KR KR1020257021837A patent/KR20250103811A/ko active Pending
- 2021-06-30 EP EP21832431.7A patent/EP4172145A4/en active Pending
- 2021-06-30 AU AU2021302692A patent/AU2021302692A1/en active Pending
- 2021-06-30 KR KR1020237003292A patent/KR102829078B1/ko active Active
- 2021-06-30 US US17/364,047 patent/US11292765B2/en active Active
- 2021-06-30 MX MX2022016212A patent/MX2022016212A/es unknown
- 2021-06-30 IL IL299506A patent/IL299506B2/en unknown
- 2021-06-30 JP JP2022580938A patent/JP7702654B2/ja active Active
- 2021-06-30 WO PCT/CA2021/050907 patent/WO2022000091A1/en not_active Ceased
- 2021-06-30 CA CA3181092A patent/CA3181092A1/en active Pending
-
2022
- 2022-02-24 US US17/679,439 patent/US20220177427A1/en not_active Abandoned
-
2024
- 2024-09-30 US US18/902,773 patent/US20250129023A1/en active Pending
-
2025
- 2025-04-30 IL IL320601A patent/IL320601A/en unknown
- 2025-06-05 JP JP2025094025A patent/JP2025143280A/ja active Pending
- 2025-08-22 US US19/308,120 patent/US20250382267A1/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3075992A (en) | 1958-09-12 | 1963-01-29 | Sandoz Ltd | Esters of indoles |
| WO1995006638A1 (en) | 1993-09-01 | 1995-03-09 | Allelix Biopharmaceuticals Inc. | Tryptamine analogs with 5-ht1d selectivity |
Non-Patent Citations (3)
| Title |
|---|
| F. Hasler et al.,Determination of psilocin and 4-hydroxyindole-3-acetic acid in plasma by HPLC-ECD and pharmacokineti,PHARMACEUTICA ACTA HELVETIAE,1997年,72,175-184 |
| Howard Sard et al.,SAR of psilocybin analogs: Discovery of a selective 5-HT2C agonist,BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,15,2005年,4555-4559 |
| Martin K. Madsen et al.,Psychedelic effects of psilocybin correlate with serotonin 2A receptor occupancy and plasma psilocin,Neuropsychopharmacology,44,2019年,1328-1334 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA3181092A1 (en) | 2022-01-06 |
| US20210403425A1 (en) | 2021-12-30 |
| WO2022000091A1 (en) | 2022-01-06 |
| MX2022016212A (es) | 2023-03-02 |
| CN119285526A (zh) | 2025-01-10 |
| EP4172145A4 (en) | 2024-08-21 |
| CN115867533A (zh) | 2023-03-28 |
| JP2025143280A (ja) | 2025-10-01 |
| IL299506A (en) | 2023-02-01 |
| IL299506B1 (en) | 2025-06-01 |
| CN115867533B (zh) | 2024-07-23 |
| KR20250103811A (ko) | 2025-07-07 |
| IL299506B2 (en) | 2025-10-01 |
| EP4172145A1 (en) | 2023-05-03 |
| KR102829078B1 (ko) | 2025-07-04 |
| US20220177427A1 (en) | 2022-06-09 |
| US11292765B2 (en) | 2022-04-05 |
| AU2021302692A1 (en) | 2023-01-19 |
| IL320601A (en) | 2025-07-01 |
| US20250129023A1 (en) | 2025-04-24 |
| US20250382267A1 (en) | 2025-12-18 |
| KR20230028543A (ko) | 2023-02-28 |
| CN119285527A (zh) | 2025-01-10 |
| JP2023531311A (ja) | 2023-07-21 |
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