JP2023528087A - ミトコンドリア機能不全、癌、及び線維症の治療に使用されるＵＳＰ３０阻害剤としての１－（５－（２－シアノピリジン－４－イル）オキサゾール－２－カルボニル）－４－メチルヘキサヒドロピロロ［３，４－ｂ］ピロール－５（１Ｈ）－カルボニトリル - Google Patents
ミトコンドリア機能不全、癌、及び線維症の治療に使用されるＵＳＰ３０阻害剤としての１－（５－（２－シアノピリジン－４－イル）オキサゾール－２－カルボニル）－４－メチルヘキサヒドロピロロ［３，４－ｂ］ピロール－５（１Ｈ）－カルボニトリル Download PDFInfo
- Publication number
- JP2023528087A JP2023528087A JP2022575399A JP2022575399A JP2023528087A JP 2023528087 A JP2023528087 A JP 2023528087A JP 2022575399 A JP2022575399 A JP 2022575399A JP 2022575399 A JP2022575399 A JP 2022575399A JP 2023528087 A JP2023528087 A JP 2023528087A
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
- A61P25/28—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Pulmonology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Epidemiology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB2008598.1A GB202008598D0 (en) | 2020-06-08 | 2020-06-08 | Novel compounds |
| GB2008598.1 | 2020-06-08 | ||
| GB2016758.1 | 2020-10-22 | ||
| GBGB2016758.1A GB202016758D0 (en) | 2020-10-22 | 2020-10-22 | Novel compounds |
| PCT/EP2021/065112 WO2021249909A1 (en) | 2020-06-08 | 2021-06-07 | 1-(5-(2-cyanopyridin-4-yl)oxazole-2-carbonyl)-4-methylhexahydropyrrolo[3,4-b]pyr role-5(1h)-carbonitrile as usp30 inhibitor for use in the treatment of mitochondrial dysfunction, cancer and fibrosis |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2023528087A true JP2023528087A (ja) | 2023-07-03 |
| JP2023528087A5 JP2023528087A5 (https=) | 2024-06-14 |
Family
ID=76444375
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022575399A Pending JP2023528087A (ja) | 2020-06-08 | 2021-06-07 | ミトコンドリア機能不全、癌、及び線維症の治療に使用されるＵＳＰ３０阻害剤としての１－（５－（２－シアノピリジン－４－イル）オキサゾール－２－カルボニル）－４－メチルヘキサヒドロピロロ［３，４－ｂ］ピロール－５（１Ｈ）－カルボニトリル |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US20230312580A1 (https=) |
| EP (1) | EP4161929B1 (https=) |
| JP (1) | JP2023528087A (https=) |
| KR (1) | KR20230022215A (https=) |
| CN (1) | CN115836073B (https=) |
| AU (1) | AU2021286831A1 (https=) |
| BR (1) | BR112022024794A2 (https=) |
| CA (1) | CA3186148A1 (https=) |
| CO (1) | CO2022017233A2 (https=) |
| DK (1) | DK4161929T3 (https=) |
| ES (1) | ES3040433T3 (https=) |
| FI (1) | FI4161929T3 (https=) |
| HR (1) | HRP20250891T1 (https=) |
| HU (1) | HUE072598T2 (https=) |
| IL (1) | IL298785B2 (https=) |
| LT (1) | LT4161929T (https=) |
| MD (1) | MD4161929T2 (https=) |
| MX (1) | MX2022015608A (https=) |
| PL (1) | PL4161929T3 (https=) |
| PT (1) | PT4161929T (https=) |
| RS (1) | RS67140B1 (https=) |
| SI (1) | SI4161929T1 (https=) |
| SM (1) | SMT202500343T1 (https=) |
| WO (1) | WO2021249909A1 (https=) |
| ZA (1) | ZA202213877B (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK4161929T3 (da) * | 2020-06-08 | 2025-08-18 | Mission Therapeutics Ltd | 1-(5-(2-cyanopyridin-4-yl)oxazol-2-carbonyl)-4-methylhexahydropyrrolo[3,4-b]pyrrol-5(1h)-carbonitril som usp30-hæmmer til anvendelse i behandling af mitokondriedysfunktion, cancer og fibrose |
| JP2024544660A (ja) | 2021-12-01 | 2024-12-03 | ミッション セラピューティクス リミティド | Ｕｓｐ３０阻害剤としての活性を有する置換ｎ－シアノピロリジン |
| CN114646700B (zh) * | 2022-03-01 | 2023-10-20 | 浙江国邦药业有限公司 | 一种（s）-吡咯烷-2-甲腈盐酸盐的检测方法 |
| GB202408928D0 (en) | 2024-06-21 | 2024-08-07 | Mission Therapeutics Ltd | Novel compounds |
| GB202411060D0 (en) | 2024-07-29 | 2024-09-11 | Mission Therapeutics Ltd | Novel compounds |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2018510183A (ja) * | 2015-03-30 | 2018-04-12 | ミッション セラピューティクス リミティド | Ｕｓｐ３０阻害剤としての１−シアノ−ピロリジン化合物 |
| JP2019513135A (ja) * | 2016-03-24 | 2019-05-23 | ミッション セラピューティクス リミティド | Ｄｕｂ阻害剤としての１−シアノピロリジン誘導体 |
Family Cites Families (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9518953D0 (en) | 1995-09-15 | 1995-11-15 | Pfizer Ltd | Pharmaceutical formulations |
| EP1272467A4 (en) | 2000-04-06 | 2003-05-07 | Merck Frosst Canada Inc | Cathepsin cysteine protease inhibitors |
| PE20060777A1 (es) | 2004-12-24 | 2006-10-06 | Boehringer Ingelheim Int | Derivados de indolinona para el tratamiento o la prevencion de enfermedades fibroticas |
| SG174050A1 (en) | 2006-04-13 | 2011-09-29 | Actelion Pharmaceuticals Ltd | Endothelin receptor antagonists for early stage idiopathic pulmonary fibrosis |
| TWI433677B (zh) | 2007-06-04 | 2014-04-11 | Avila Therapeutics Inc | 雜環化合物及其用途 |
| US20090264431A1 (en) | 2007-08-20 | 2009-10-22 | Palovich Michael R | Novel cathepsin c inhibitors and their use |
| WO2009129371A1 (en) | 2008-04-18 | 2009-10-22 | Glaxo Group Limited | Cathepsin c inhibitors |
| WO2009129370A1 (en) | 2008-04-18 | 2009-10-22 | Glaxo Group Limited | Cathepsin c inhibitors |
| WO2009129365A1 (en) | 2008-04-18 | 2009-10-22 | Glaxo Group Limited | Cathepsin c inhibitors |
| US20120309820A1 (en) | 2011-06-04 | 2012-12-06 | Jb Therapeutics Inc. | Methods of treating fibrotic diseases using tetrahydrocannabinol-11-oic acids |
| EP2565186A1 (en) | 2011-09-02 | 2013-03-06 | Hybrigenics S.A. | Selective and reversible inhibitors of ubiquitin specific protease 7 |
| RS58361B1 (sr) | 2013-07-31 | 2019-03-29 | Merck Patent Gmbh | Piridini, pirimidini i pirazini, kao inhibitori btk i njihova upotreba |
| US9963444B2 (en) | 2014-05-19 | 2018-05-08 | Northeastern University | N-acylethanolamine hydrolyzing acid amidase (NAAA) inhibitors and their use thereof |
| US20170095457A1 (en) | 2014-05-27 | 2017-04-06 | David Lonergan | Compositions and methods of delivery of deubiquitinase inhibitors |
| WO2016019237A2 (en) | 2014-07-31 | 2016-02-04 | Pharmacyclics Llc | Inhibitors of bruton's tyrosine kinase |
| GB201416754D0 (en) | 2014-09-23 | 2014-11-05 | Mission Therapeutics Ltd | Novel compounds |
| WO2017009650A1 (en) | 2015-07-14 | 2017-01-19 | Mission Therapeutics Limited | Cyanopyrrolidines as dub inhibitors for the treatment of cancer |
| GB201521109D0 (en) | 2015-11-30 | 2016-01-13 | Mission Therapeutics Ltd | Novel compounds |
| GB201522267D0 (en) | 2015-12-17 | 2016-02-03 | Mission Therapeutics Ltd | Novel compounds |
| GB201522768D0 (en) | 2015-12-23 | 2016-02-03 | Mission Therapeutics Ltd | Novel compounds |
| GB201602854D0 (en) | 2016-02-18 | 2016-04-06 | Mission Therapeutics Ltd | Novel compounds |
| GB201603779D0 (en) | 2016-03-04 | 2016-04-20 | Mission Therapeutics Ltd | Novel compounds |
| GB201604647D0 (en) | 2016-03-18 | 2016-05-04 | Mission Therapeutics Ltd | Novel compounds |
| GB201604638D0 (en) | 2016-03-18 | 2016-05-04 | Mission Therapeutics Ltd | Novel compounds |
| US11014912B2 (en) | 2016-09-27 | 2021-05-25 | Mission Therapeutics Limited | Cyanopyrrolidine derivatives with activity as inhibitors of USP30 |
| GB201616511D0 (en) | 2016-09-29 | 2016-11-16 | Mission Therapeutics Limited | Novel compounds |
| GB201616627D0 (en) | 2016-09-30 | 2016-11-16 | Mission Therapeutics Limited | Novel compounds |
| TWI771327B (zh) | 2016-10-05 | 2022-07-21 | 英商使命醫療公司 | 新穎化合物 |
| US10968172B2 (en) | 2017-05-15 | 2021-04-06 | Mitobridge, Inc. | USP30 inhibitors |
| GB201708652D0 (en) | 2017-05-31 | 2017-07-12 | Mission Therapeutics Ltd | Novel compounds and uses |
| GB2563595B (en) | 2017-06-19 | 2020-04-15 | Edwards Ltd | Twin-shaft pumps |
| AU2018346597B2 (en) | 2017-10-06 | 2023-07-13 | Forma Therapeutics, Inc. | Inhibiting Ubiquitin Specific Peptidase 30 |
| GB2571731A (en) | 2018-03-06 | 2019-09-11 | Mission Therapeutics Ltd | Novel compounds and uses |
| JP7449242B2 (ja) | 2018-05-17 | 2024-03-13 | フォーマ セラピューティクス，インコーポレイテッド | ユビキチン特異的ペプチダーゼ３０（ｕｓｐ３０）阻害剤として有用な縮合二環化合物 |
| US11572374B2 (en) | 2018-08-14 | 2023-02-07 | Amgen Inc. | N-cyano-7-azanorbornane derivatives and uses thereof |
| JP7530889B2 (ja) | 2018-10-05 | 2024-08-08 | フォーマ セラピューティクス，インコーポレイテッド | ユビキチン特異的プロテアーゼ３０（ｕｓｐ３０）阻害剤として作用する縮合ピロリン |
| GB201905375D0 (en) | 2019-04-16 | 2019-05-29 | Mission Therapeutics Ltd | Novel compounds |
| GB201905371D0 (en) | 2019-04-16 | 2019-05-29 | Mission Therapeutics Ltd | Novel compounds |
| GB201912674D0 (en) | 2019-09-04 | 2019-10-16 | Mission Therapeutics Ltd | Novel compounds |
| DK4161929T3 (da) * | 2020-06-08 | 2025-08-18 | Mission Therapeutics Ltd | 1-(5-(2-cyanopyridin-4-yl)oxazol-2-carbonyl)-4-methylhexahydropyrrolo[3,4-b]pyrrol-5(1h)-carbonitril som usp30-hæmmer til anvendelse i behandling af mitokondriedysfunktion, cancer og fibrose |
-
2021
- 2021-06-07 DK DK21732212.2T patent/DK4161929T3/da active
- 2021-06-07 AU AU2021286831A patent/AU2021286831A1/en active Pending
- 2021-06-07 ES ES21732212T patent/ES3040433T3/es active Active
- 2021-06-07 WO PCT/EP2021/065112 patent/WO2021249909A1/en not_active Ceased
- 2021-06-07 MD MDE20230409T patent/MD4161929T2/ro unknown
- 2021-06-07 HR HRP20250891TT patent/HRP20250891T1/hr unknown
- 2021-06-07 US US18/008,352 patent/US20230312580A1/en active Pending
- 2021-06-07 KR KR1020237000509A patent/KR20230022215A/ko active Pending
- 2021-06-07 CN CN202180040683.1A patent/CN115836073B/zh active Active
- 2021-06-07 BR BR112022024794A patent/BR112022024794A2/pt unknown
- 2021-06-07 JP JP2022575399A patent/JP2023528087A/ja active Pending
- 2021-06-07 SI SI202130328T patent/SI4161929T1/sl unknown
- 2021-06-07 EP EP21732212.2A patent/EP4161929B1/en active Active
- 2021-06-07 LT LTEPPCT/EP2021/065112T patent/LT4161929T/lt unknown
- 2021-06-07 IL IL298785A patent/IL298785B2/en unknown
- 2021-06-07 FI FIEP21732212.2T patent/FI4161929T3/fi active
- 2021-06-07 PT PT217322122T patent/PT4161929T/pt unknown
- 2021-06-07 PL PL21732212.2T patent/PL4161929T3/pl unknown
- 2021-06-07 RS RS20250744A patent/RS67140B1/sr unknown
- 2021-06-07 MX MX2022015608A patent/MX2022015608A/es unknown
- 2021-06-07 HU HUE21732212A patent/HUE072598T2/hu unknown
- 2021-06-07 SM SM20250343T patent/SMT202500343T1/it unknown
- 2021-06-07 CA CA3186148A patent/CA3186148A1/en active Pending
-
2022
- 2022-11-30 CO CONC2022/0017233A patent/CO2022017233A2/es unknown
- 2022-12-21 ZA ZA2022/13877A patent/ZA202213877B/en unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2018510183A (ja) * | 2015-03-30 | 2018-04-12 | ミッション セラピューティクス リミティド | Ｕｓｐ３０阻害剤としての１−シアノ−ピロリジン化合物 |
| JP2019513135A (ja) * | 2016-03-24 | 2019-05-23 | ミッション セラピューティクス リミティド | Ｄｕｂ阻害剤としての１−シアノピロリジン誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| SI4161929T1 (sl) | 2025-10-30 |
| CN115836073A (zh) | 2023-03-21 |
| IL298785B2 (en) | 2026-03-01 |
| MX2022015608A (es) | 2023-03-03 |
| KR20230022215A (ko) | 2023-02-14 |
| IL298785B1 (en) | 2025-11-01 |
| HRP20250891T1 (hr) | 2025-09-26 |
| LT4161929T (lt) | 2025-09-25 |
| RS67140B1 (sr) | 2025-09-30 |
| FI4161929T3 (fi) | 2025-07-30 |
| EP4161929B1 (en) | 2025-04-30 |
| EP4161929A1 (en) | 2023-04-12 |
| IL298785A (en) | 2023-02-01 |
| WO2021249909A1 (en) | 2021-12-16 |
| MD4161929T2 (ro) | 2025-10-31 |
| US20230312580A1 (en) | 2023-10-05 |
| CA3186148A1 (en) | 2021-12-16 |
| CO2022017233A2 (es) | 2023-03-07 |
| DK4161929T3 (da) | 2025-08-18 |
| HUE072598T2 (hu) | 2025-11-28 |
| ZA202213877B (en) | 2024-07-31 |
| CN115836073B (zh) | 2024-08-27 |
| PT4161929T (pt) | 2025-08-05 |
| PL4161929T3 (pl) | 2026-01-05 |
| AU2021286831A1 (en) | 2023-02-02 |
| BR112022024794A2 (pt) | 2022-12-27 |
| ES3040433T3 (en) | 2025-10-30 |
| SMT202500343T1 (it) | 2025-11-10 |
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