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 |
| PCT/CA2021/050907 WO2022000091A1 (en) | 2020-06-30 | 2021-06-30 | Tryptamine prodrugs |
| US17/364,047 | 2021-06-30 |
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 (3)
| Publication Number | Publication Date |
|---|---|
| JP2023531311A JP2023531311A (ja) | 2023-07-21 |
| JP2023531311A5 JP2023531311A5 (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) | KR102829078B1 (https=) |
| CN (3) | CN119285527A (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 |
|---|---|---|---|---|
| CA3152752A1 (en) | 2019-10-01 | 2021-04-08 | Thomas Henley | Genetic engineering of fungi to modulate tryptamine expression |
| KR20220137081A (ko) | 2020-02-04 | 2022-10-11 | 마인드셋 파마 인크. | Cns 장애의 치료를 위한 세로토닌성 사이키델릭 작용제로서의 실로신 유도체 |
| BR112022015379A2 (pt) | 2020-02-04 | 2022-09-27 | Mindset Pharma Inc | Derivados de 3-pirrolidino-indol como agentes psicodélicos serotonérgicos para o tratamento de distúrbios do snc |
| WO2021226416A1 (en) | 2020-05-08 | 2021-11-11 | Psilera Inc. | Novel compositions of matter and pharmaceutical compositions |
| CN119285527A (zh) * | 2020-06-30 | 2025-01-10 | 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 |
| EP4255422A4 (en) * | 2020-12-03 | 2024-12-18 | Mydecine Innovations Group Inc. | NEW PSILOCIN ANALOGUE COMPOSITIONS AND METHODS OF THEIR SYNTHESIS |
| JP2024500397A (ja) * | 2020-12-18 | 2024-01-09 | コンパス パスファインダー リミテッド | 治療用途のための修飾インドールアルカロイド |
| EP4155306A1 (en) | 2021-01-15 | 2023-03-29 | Beckley Psytech Limited | Neuroactive ergoline analogue |
| US12534441B2 (en) | 2021-01-15 | 2026-01-27 | Beckley Psytech Limited | Tryptamine analogues |
| US11312684B1 (en) | 2021-02-10 | 2022-04-26 | Eleusis Therapeutics Us, Inc. | Pharmaceutically acceptable salts of psilocin and uses thereof |
| MX2023014630A (es) | 2021-06-08 | 2024-01-30 | Atai Therapeutics Inc | Activadores de dimetoxifenilalquilamina de receptores de serotonina. |
| AU2022309017A1 (en) | 2021-07-07 | 2024-01-25 | Terran Biosciences Inc. | N,n-dimethyltryptamine and related psychedlics and uses thereof |
| KR20240058859A (ko) | 2021-08-12 | 2024-05-03 | 쿨레온 엘엘씨 | 환각성 및 비환각성 세로토닌 수용체 작용제 및 이의 제조 및 사용 방법 |
| JP2024534801A (ja) * | 2021-08-20 | 2024-09-26 | テラン バイオサイエンシズ インコーポレイテッド | サイロシンのプロドラッグ及び誘導体ならびにその使用 |
| US20250011351A1 (en) | 2021-11-12 | 2025-01-09 | Terran Biosciences Inc. | Psilocybin and o-acetylpsilocin, salts and solid state forms thereof |
| EP4444698A4 (en) * | 2021-12-10 | 2025-07-09 | Caamtech Inc | PSILOCYBIN DERIVATIVES |
| US20250051278A1 (en) * | 2021-12-14 | 2025-02-13 | Reunion Neuroscience, Inc. | Tryptamine prodrugs |
| EP4457203A4 (en) | 2021-12-27 | 2025-12-17 | Atai Therapeutics Inc | AMINOTETRALINE ACTIVATORS OF SEROTONIN RECEPTORS |
| WO2023129956A2 (en) | 2021-12-30 | 2023-07-06 | ATAI Life Sciences AG | Dimethyltryptamine analogues as nitric oxide delivery drugs |
| CN118984868A (zh) | 2021-12-31 | 2024-11-19 | 恩派瑞安神经科学公司 | 用于产生精神药物生物碱的遗传修饰的生物体 |
| 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 |
| AU2023234202A1 (en) * | 2022-03-18 | 2024-11-07 | Enveric Biosciences Canada Inc. | Salts of c4-carboxylic acid- and c4-carbonothioate-substituted tryptamine derivatives and methods of using |
| CA3246245A1 (en) * | 2022-03-18 | 2023-09-21 | Enveric Biosciences Canada Inc. | C4 CARBOXYLIC ACID SUBSTITUTED TRYPTAMINE DERIVATIVES AND METHODS OF USE |
| WO2023173196A1 (en) | 2022-03-18 | 2023-09-21 | 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 |
| CA3248442A1 (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 |
| CA3258595A1 (en) * | 2022-07-27 | 2024-02-01 | Reconnect Labs Ag | HIGHLY SOLUBBLE FORMULATIONS BASED ON HARMIN |
| 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 |
| WO2024145719A1 (en) * | 2023-01-05 | 2024-07-11 | Reunion Neuroscience Inc. | Improved pharmacokinetics of tryptamine prodrugs |
| WO2024178051A2 (en) * | 2023-02-22 | 2024-08-29 | Caamtech, Inc. | Tryptamine derivatives |
| US12343319B2 (en) | 2023-05-01 | 2025-07-01 | 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 |
|---|---|---|---|---|
| BE582353A (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 |
| US5376645A (en) | 1990-01-23 | 1994-12-27 | University Of Kansas | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof |
| KR0166088B1 (ko) | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
| GB9711643D0 (en) | 1997-06-05 | 1997-07-30 | Janssen Pharmaceutica Nv | Glass thermoplastic systems |
| US7655691B2 (en) * | 2004-09-27 | 2010-02-02 | Sard Howard P | Indole compounds useful as serotonin selective agents |
| HUE032158T2 (en) | 2008-10-31 | 2017-09-28 | Univ Mississippi | Process for the preparation of delta9-THC amino acid esters |
| 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 |
| CA3132731A1 (en) | 2019-03-07 | 2020-09-10 | University Of Padova | Compositions and methods of use comprising substances with neural plasticity actions administered at non-psychedelic/psychotomimetic dosages and formulations |
| KR20220137081A (ko) | 2020-02-04 | 2022-10-11 | 마인드셋 파마 인크. | Cns 장애의 치료를 위한 세로토닌성 사이키델릭 작용제로서의 실로신 유도체 |
| CN119285527A (zh) * | 2020-06-30 | 2025-01-10 | 瑞安神经科学公司 | 色胺前药 |
| JP2024500397A (ja) * | 2020-12-18 | 2024-01-09 | コンパス パスファインダー リミテッド | 治療用途のための修飾インドールアルカロイド |
-
2021
- 2021-06-30 CN CN202410898937.9A patent/CN119285527A/zh active Pending
- 2021-06-30 WO PCT/CA2021/050907 patent/WO2022000091A1/en not_active Ceased
- 2021-06-30 AU AU2021302692A patent/AU2021302692A1/en active Pending
- 2021-06-30 IL IL299506A patent/IL299506B2/en unknown
- 2021-06-30 KR KR1020237003292A patent/KR102829078B1/ko active Active
- 2021-06-30 KR KR1020257021837A patent/KR20250103811A/ko active Pending
- 2021-06-30 CA CA3181092A patent/CA3181092A1/en active Pending
- 2021-06-30 US US17/364,047 patent/US11292765B2/en active Active
- 2021-06-30 MX MX2022016212A patent/MX2022016212A/es unknown
- 2021-06-30 CN CN202410898893.XA patent/CN119285526A/zh active Pending
- 2021-06-30 EP EP21832431.7A patent/EP4172145A4/en active Pending
- 2021-06-30 CN CN202180046999.1A patent/CN115867533B/zh active Active
- 2021-06-30 JP JP2022580938A patent/JP7702654B2/ja active Active
-
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 |
|---|---|
| IL299506B2 (en) | 2025-10-01 |
| CN119285526A (zh) | 2025-01-10 |
| IL299506A (en) | 2023-02-01 |
| IL299506B1 (en) | 2025-06-01 |
| CA3181092A1 (en) | 2022-01-06 |
| US20250382267A1 (en) | 2025-12-18 |
| KR20250103811A (ko) | 2025-07-07 |
| US20250129023A1 (en) | 2025-04-24 |
| EP4172145A4 (en) | 2024-08-21 |
| AU2021302692A1 (en) | 2023-01-19 |
| WO2022000091A1 (en) | 2022-01-06 |
| US20210403425A1 (en) | 2021-12-30 |
| EP4172145A1 (en) | 2023-05-03 |
| JP2025143280A (ja) | 2025-10-01 |
| US20220177427A1 (en) | 2022-06-09 |
| CN115867533B (zh) | 2024-07-23 |
| US11292765B2 (en) | 2022-04-05 |
| KR20230028543A (ko) | 2023-02-28 |
| IL320601A (en) | 2025-07-01 |
| CN119285527A (zh) | 2025-01-10 |
| KR102829078B1 (ko) | 2025-07-04 |
| MX2022016212A (es) | 2023-03-02 |
| JP2023531311A (ja) | 2023-07-21 |
| CN115867533A (zh) | 2023-03-28 |
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