ECSP23034049A - Preparación de derivados de oxindol como nuevos inhibidores de la diacilglicerol o-aciltransferasa 2 - Google Patents
Preparación de derivados de oxindol como nuevos inhibidores de la diacilglicerol o-aciltransferasa 2Info
- Publication number
- ECSP23034049A ECSP23034049A ECSENADI202334049A ECDI202334049A ECSP23034049A EC SP23034049 A ECSP23034049 A EC SP23034049A EC SENADI202334049 A ECSENADI202334049 A EC SENADI202334049A EC DI202334049 A ECDI202334049 A EC DI202334049A EC SP23034049 A ECSP23034049 A EC SP23034049A
- Authority
- EC
- Ecuador
- Prior art keywords
- formula
- compounds
- inhibitors
- acyltransferase
- preparation
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
-
- 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
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- 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
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Epidemiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Gastroenterology & Hepatology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Se inventan compuestos de fórmula I [IMAGEN ADJUNTA] y sales farmacéuticamente aceptables, ésteres y profármacos de los mismos, que son inhibidores de DGAT2. También se proporcionan métodos de preparación de compuestos de Fórmula I, composiciones farmacéuticas que comprenden compuestos de Fórmula I y métodos de uso de estos compuestos para tratar la esteatosis hepática, esteatohepatitis no alcohólica (EHNA), fibrosis, diabetes mellitus de tipo 2, obesidad, hiperlipidemia, hipercolesterolemia, ateroesclerosis, declive cognitivo, demencia, enfermedades cardiorrenales tales como enfermedades renales crónicas e insuficiencia cardíaca y enfermedades y afecciones relacionadas, que comprenden administrar un compuesto de Fórmula I a un paciente que lo necesita.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US202063089063P | 2020-10-08 | 2020-10-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ECSP23034049A true ECSP23034049A (es) | 2023-06-30 |
Family
ID=78709520
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ECSENADI202334049A ECSP23034049A (es) | 2020-10-08 | 2023-05-08 | Preparación de derivados de oxindol como nuevos inhibidores de la diacilglicerol o-aciltransferasa 2 |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US12410159B2 (es) |
| EP (1) | EP4225735A1 (es) |
| JP (1) | JP7482324B2 (es) |
| KR (1) | KR20230079427A (es) |
| CN (1) | CN116457346A (es) |
| AR (1) | AR123701A1 (es) |
| AU (1) | AU2021358946A1 (es) |
| CA (1) | CA3195032A1 (es) |
| CL (1) | CL2023000978A1 (es) |
| CO (1) | CO2023004366A2 (es) |
| CR (1) | CR20230160A (es) |
| DO (1) | DOP2023000068A (es) |
| EC (1) | ECSP23034049A (es) |
| IL (1) | IL301799A (es) |
| JO (1) | JOP20230071A1 (es) |
| MX (1) | MX2023003844A (es) |
| PE (1) | PE20240217A1 (es) |
| TW (1) | TW202229232A (es) |
| WO (1) | WO2022076496A1 (es) |
| ZA (1) | ZA202304150B (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN119384420A (zh) * | 2022-06-03 | 2025-01-28 | 多曼治疗学公司 | 新型par-2抑制剂 |
| IL321166A (en) | 2022-12-02 | 2025-07-01 | Merck Sharp & Dohme Llc | Preparation of fused azole derivatives as novel diacylglyceride o-acyltransferase 2 inhibitors |
| WO2026096330A1 (en) | 2024-10-28 | 2026-05-07 | Merck Sharp & Dohme Llc | Glp-1 receptor agonists and methods of use |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
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| ZA981936B (en) | 1997-03-07 | 1999-09-06 | Metabasis Therapeutics Inc | Novel benzimidazole inhibitors of fructose 1,6-bisphosphatase. |
| WO1998039342A1 (en) | 1997-03-07 | 1998-09-11 | Metabasis Therapeutics, Inc. | Novel indole and azaindole inhibitors of fructose-1,6-bisphosphatase |
| WO1998039344A1 (en) | 1997-03-07 | 1998-09-11 | Metabasis Therapeutics, Inc. | Novel purine inhibitors of fructose-1,6-bisphosphatase |
| WO2000014095A1 (en) | 1998-09-09 | 2000-03-16 | Metabasis Therapeutics, Inc. | Novel heteroaromatic inhibitors of fructose 1,6-bisphosphatase |
| JP2004513076A (ja) | 2000-07-25 | 2004-04-30 | メルク エンド カムパニー インコーポレーテッド | 糖尿病治療で有用なn−置換インドール類 |
| US6852738B2 (en) | 2001-01-30 | 2005-02-08 | Merck & Co., Inc. | Acyl sulfamides for treatment of obesity, diabetes and lipid disorders |
| WO2003053363A2 (en) | 2001-12-19 | 2003-07-03 | Millennium Pharmaceuticals, Inc. | Human diacylglycerol acyltransferase 2 (dgat2) family members and uses therefor |
| AR040241A1 (es) | 2002-06-10 | 2005-03-23 | Merck & Co Inc | Inhibidores de la 11-beta-hidroxiesteroide deshidrogrenasa 1 para el tratamiento de la diabetes obesidad y dislipidemia |
| JP4340232B2 (ja) | 2002-08-29 | 2009-10-07 | メルク エンド カムパニー インコーポレーテッド | 抗糖尿病活性を有するインドール類 |
| NZ538031A (en) | 2002-08-29 | 2007-10-26 | Merck & Co Inc | Indoles having anti-diabetic activity |
| WO2004066963A2 (en) | 2003-01-17 | 2004-08-12 | Merck & Co., Inc. | N-cyclohexylaminocarbonyl benzenesulfonamide derivatives |
| US20080287479A1 (en) * | 2006-12-20 | 2008-11-20 | Pfizer Inc | Inhibitors of serine palmitoyltransferase |
| CA2691010A1 (en) | 2007-06-28 | 2008-12-31 | Merck Frosst Canada Ltd. | Substituted fused pyrimidines as antagonists of gpr105 activity |
| EP2174343A1 (en) | 2007-06-28 | 2010-04-14 | Semiconductor Energy Laboratory Co, Ltd. | Manufacturing method of semiconductor device |
| WO2009042053A2 (en) | 2007-09-21 | 2009-04-02 | Merck & Co., Inc. | Neuromedin u receptor agonists and uses thereof |
| WO2010065310A1 (en) * | 2008-12-03 | 2010-06-10 | Via Pharmaceuticals, Inc | Inhibitors of diacylglycerol acyltransferase |
| WO2010077839A1 (en) | 2008-12-15 | 2010-07-08 | Wyeth Llc (Formerly Known As Wyeth) | Substituted oxindol cb2 agonists for pain treatment |
| TW201201815A (en) | 2010-05-28 | 2012-01-16 | Gilead Sciences Inc | 1'-substituted-carba-nucleoside prodrugs for antiviral treatment |
| SG11201405477XA (en) | 2012-04-06 | 2014-11-27 | Pfizer | Diacylglycerol acyltransferase 2 inhibitors |
| AR098394A1 (es) | 2013-11-25 | 2016-05-26 | Lilly Co Eli | Inhibidores de dgat2 (diacilglicerol o-aciltransferasa 2) |
| RU2639102C2 (ru) | 2013-11-26 | 2017-12-19 | Хьюлетт-Паккард Дивелопмент Компани, Лп | Устройство выброса текучей среды с односторонним температурным датчиком |
| EP3119757B1 (en) | 2014-03-17 | 2018-05-16 | Pfizer Inc | Diacylglycerol acyltransferase 2 inhibitors for use in the treatment of metabolic and related disorders |
| US10568876B2 (en) | 2014-09-05 | 2020-02-25 | Merck Sharp & Dohme Corp. | Tetrahydroisoquinoline derivatives useful as inhibitors of diacylglyceride O-acyltransferase 2 |
| US9828369B2 (en) | 2014-09-05 | 2017-11-28 | Merck Sharpe & Dohme Corp. | Isoquinoline derivatives useful as inhibitors of diacylglyceride O-acyltransferase 2 |
| US9877957B2 (en) | 2014-09-05 | 2018-01-30 | Merck Sharp & Dohme Corp. | Tetrahydroisoquinoline derivatives useful as inhibitors of diacylglyceride O-acyltransferase 2 |
| PE20180800A1 (es) | 2015-07-10 | 2018-05-09 | Ionis Pharmaceuticals Inc | Moduladores de diaciglicerol aciltransferasa 2 (dgat2) |
| AR109179A1 (es) | 2016-08-19 | 2018-11-07 | Pfizer | Inhibidores de diacilglicerol aciltransferasa 2 |
| CA3043206A1 (en) * | 2016-11-18 | 2018-05-24 | Merck Sharp & Dohme Corp. | Indole derivatives useful as inhibitors of diacylglyceride o-acyltransferase 2 |
| KR20190078646A (ko) * | 2016-11-18 | 2019-07-04 | 머크 샤프 앤드 돔 코포레이션 | 디아실글리세리드 o-아실트랜스퍼라제 2의 억제제로서 유용한 인다졸 유도체 |
| TWI771766B (zh) | 2019-10-04 | 2022-07-21 | 美商輝瑞股份有限公司 | 二醯基甘油醯基轉移酶2 抑制劑 |
| EP4077309A1 (en) | 2019-12-19 | 2022-10-26 | Arvinas Operations, Inc. | Compounds and methods for the targeted degradation of androgen receptor |
| US11541039B2 (en) | 2020-10-08 | 2023-01-03 | Endogena Therapeutics, Inc. | Compounds and their use as therapeutically active substances in the treatment and/or reducing signs or symptoms of diseases involving the retinal pigment epithelium |
| PT4225739T (pt) | 2020-10-08 | 2026-04-07 | Merck Sharp & Dohme Llc | Preparação de derivados de benzimidazolona como novos inibidores da diacilglicerol o-aciltransferase 2 |
| HRP20241184T1 (hr) | 2020-10-08 | 2024-11-22 | Leukos Biotech, S.L. | Moćni i selektivni spojevi kao modulatori serotonin 1b receptora |
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2021
- 2021-10-06 TW TW110137151A patent/TW202229232A/zh unknown
- 2021-10-06 WO PCT/US2021/053681 patent/WO2022076496A1/en not_active Ceased
- 2021-10-06 EP EP21811162.3A patent/EP4225735A1/en active Pending
- 2021-10-06 PE PE2023001362A patent/PE20240217A1/es unknown
- 2021-10-06 US US17/494,896 patent/US12410159B2/en active Active
- 2021-10-06 CR CR20230160A patent/CR20230160A/es unknown
- 2021-10-06 CA CA3195032A patent/CA3195032A1/en active Pending
- 2021-10-06 KR KR1020237014915A patent/KR20230079427A/ko active Pending
- 2021-10-06 MX MX2023003844A patent/MX2023003844A/es unknown
- 2021-10-06 IL IL301799A patent/IL301799A/en unknown
- 2021-10-06 AR ARP210102767A patent/AR123701A1/es unknown
- 2021-10-06 CN CN202180076390.9A patent/CN116457346A/zh active Pending
- 2021-10-06 JP JP2023521377A patent/JP7482324B2/ja active Active
- 2021-10-06 AU AU2021358946A patent/AU2021358946A1/en active Pending
-
2023
- 2023-04-04 ZA ZA2023/04150A patent/ZA202304150B/en unknown
- 2023-04-04 CL CL2023000978A patent/CL2023000978A1/es unknown
- 2023-04-05 DO DO2023000068A patent/DOP2023000068A/es unknown
- 2023-04-05 CO CONC2023/0004366A patent/CO2023004366A2/es unknown
- 2023-04-06 JO JOJO/P/2023/0071A patent/JOP20230071A1/ar unknown
- 2023-05-08 EC ECSENADI202334049A patent/ECSP23034049A/es unknown
-
2024
- 2024-05-23 US US18/672,808 patent/US12428411B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US20220112181A1 (en) | 2022-04-14 |
| AR123701A1 (es) | 2023-01-04 |
| KR20230079427A (ko) | 2023-06-07 |
| CL2023000978A1 (es) | 2023-09-29 |
| CR20230160A (es) | 2023-06-02 |
| MX2023003844A (es) | 2023-04-14 |
| DOP2023000068A (es) | 2023-05-31 |
| CN116457346A (zh) | 2023-07-18 |
| WO2022076496A1 (en) | 2022-04-14 |
| US20240327391A1 (en) | 2024-10-03 |
| JP7482324B2 (ja) | 2024-05-13 |
| IL301799A (en) | 2023-05-01 |
| CA3195032A1 (en) | 2022-04-14 |
| JP2023541714A (ja) | 2023-10-03 |
| PE20240217A1 (es) | 2024-02-16 |
| AU2021358946A9 (en) | 2024-02-08 |
| US12428411B2 (en) | 2025-09-30 |
| EP4225735A1 (en) | 2023-08-16 |
| CO2023004366A2 (es) | 2023-04-27 |
| JOP20230071A1 (ar) | 2023-04-06 |
| AU2021358946A1 (en) | 2023-06-08 |
| ZA202304150B (en) | 2024-12-18 |
| TW202229232A (zh) | 2022-08-01 |
| US12410159B2 (en) | 2025-09-09 |
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