PE20220341A1 - Derivados de quinazolin-4-ona utiles en el tratamiento de enfermedades y trastornos asociadas con braf - Google Patents
Derivados de quinazolin-4-ona utiles en el tratamiento de enfermedades y trastornos asociadas con brafInfo
- Publication number
- PE20220341A1 PE20220341A1 PE2021002078A PE2021002078A PE20220341A1 PE 20220341 A1 PE20220341 A1 PE 20220341A1 PE 2021002078 A PE2021002078 A PE 2021002078A PE 2021002078 A PE2021002078 A PE 2021002078A PE 20220341 A1 PE20220341 A1 PE 20220341A1
- Authority
- PE
- Peru
- Prior art keywords
- alkyl
- braf
- optionally substituted
- independently selected
- dihydroquinazolin
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/90—Oxygen atoms with acyclic radicals attached in position 2 or 3
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- 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
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/91—Oxygen atoms with aryl or aralkyl radicals attached in position 2 or 3
-
- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
En la presente se proveen compuestos de la formula I, en donde L es O, NH o S; X1 es CH o N; R1 es alquilo de C1-C6, deuteroalquilo de C1-C6, fluoroalquilo de C1-C6, cicloalquilo de C3-C6, (cicloalquilo de C3-C6)CH2-, (alcoxi de C1-C6)alquilo de C1-C6, Ar1 , entre otros; Ar1 es fenilo que esta opcionalmente sustituido con 1-5 sustituyentes seleccionados independientemente de halogeno y alquilo de C1-C3; R2 es metilo, -CD3 o HC?C-; R3 es F, Cl, CN o metilo; R4 es H, F o Cl; R5 es H, F, Cl o metilo; R6 es alquilo de C1-C6, fluoroalquilo de C1-C6, (Cyc1 )alquilo de C1-C6, (alcoxi de C1-C3)alquilo de C1-C6, hetAr2 , Ar2 o RaRbN-; Cyc1 es un anillo carbociclico saturado de 3-6 miembros; hetAr2 es un heteroarilo de 5-6 miembros que tiene 1-2 heteroatomos de anillo seleccionados independientemente de N, O y S y opcionalmente sustituido con 1-3 sustituyentes seleccionados independientemente de halogeno y alquilo de C1-C3; Ar2 es fenilo opcionalmente sustituido con 1-5 sustituyentes seleccionados independientemente de halogeno y alquilo de C1-C6; y Ra y Rb son independientemente alquilo de C1-C3, o Ra y Rb junto con el atomo de nitrogeno al que estan unidos forman un anillo heterociclico saturado monociclico de 5-6 miembros opcionalmente sustituido con 1-2 halogenos. Son compuestos preferidos: N-(3-((3,5-dimetil-4-oxo-3,4-dihidroquinazolin-6-il)amino)-2,4- difluorofenil)propano-1-sulfonamida, N-(3-((3,5-dimetil-4-oxo-3,4-dihidroquinazolin-6-il)amino)-2,4-difluorofenil)-3- fluoropropano-1-sulfonamida, N-(2-cloro-3-((3,5-dimetil-4-oxo-3,4-dihidroquinazolin-6-il)amino)fenil)propano-1- sulfonamida, entre otros. Dichos compuestos son utiles para el tratamiento de enfermedades y trastornos asociados a BRAF, incluyendo tumores asociados a BRAF, incluyendo tumores malignos y benignos asociados a BRAF del SNC y tumores asociados a BRAF extracraneales malignos.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201962868581P | 2019-06-28 | 2019-06-28 | |
US202063021410P | 2020-05-07 | 2020-05-07 | |
PCT/IB2020/055992 WO2020261156A1 (en) | 2019-06-28 | 2020-06-24 | Quinazolin-4-one derivatives useful for the treatment of braf-associated diseases and disorders |
Publications (1)
Publication Number | Publication Date |
---|---|
PE20220341A1 true PE20220341A1 (es) | 2022-03-14 |
Family
ID=71465389
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PE2021002078A PE20220341A1 (es) | 2019-06-28 | 2020-06-24 | Derivados de quinazolin-4-ona utiles en el tratamiento de enfermedades y trastornos asociadas con braf |
Country Status (20)
Country | Link |
---|---|
US (2) | US11414404B2 (es) |
EP (1) | EP3990437A1 (es) |
JP (1) | JP7169469B2 (es) |
KR (1) | KR20220011712A (es) |
CN (1) | CN114026073A (es) |
AU (1) | AU2020302352B2 (es) |
BR (1) | BR112021025102A2 (es) |
CA (1) | CA3144859C (es) |
CO (1) | CO2021017438A2 (es) |
CR (1) | CR20210626A (es) |
CU (1) | CU20210098A7 (es) |
EC (1) | ECSP21093541A (es) |
IL (1) | IL288214A (es) |
MA (1) | MA56387A (es) |
MX (1) | MX2021015903A (es) |
PE (1) | PE20220341A1 (es) |
TW (1) | TWI817018B (es) |
UY (1) | UY38767A (es) |
WO (1) | WO2020261156A1 (es) |
ZA (1) | ZA202201329B (es) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI817018B (zh) * | 2019-06-28 | 2023-10-01 | 美商艾瑞生藥股份有限公司 | 用於治療braf相關的疾病和失調症之化合物 |
KR20220110554A (ko) * | 2019-12-10 | 2022-08-08 | 에프. 호프만-라 로슈 아게 | 신규 메틸퀴나졸리논 유도체 |
PE20221027A1 (es) * | 2019-12-10 | 2022-06-16 | Hoffmann La Roche | Nuevos inhibidores de braf como rompedores de la paradoja |
US20220288074A1 (en) | 2020-06-09 | 2022-09-15 | Array Biopharma Inc. | Compounds for the treatment of braf-associated diseases and disorders |
TWI825637B (zh) | 2021-03-31 | 2023-12-11 | 美商輝瑞股份有限公司 | 啶-1,6(2h,7h)-二酮 |
KR20240008410A (ko) * | 2021-06-09 | 2024-01-18 | 에프. 호프만-라 로슈 아게 | 암 치료를 위한 병용요법 |
WO2023078881A1 (en) * | 2021-11-04 | 2023-05-11 | F. Hoffmann-La Roche Ag | Novel use of quinazolinone compound for the treatment of cancer |
WO2023105371A1 (en) * | 2021-12-08 | 2023-06-15 | Array Biopharma Inc. | Crystalline form of n-(2-chloro-3-((5-chloro-3-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)amino)-4-fluorophenyl)-3-fluoroazetidine-1-sulfonamide |
WO2023230554A1 (en) | 2022-05-25 | 2023-11-30 | Pfizer Inc. | Combination of a braf inhibitor, an egfr inhibitor, and a pd-1 antagonist for the treatment of braf v600e-mutant, msi-h/dmmr colorectal cancer |
US11957759B1 (en) | 2022-09-07 | 2024-04-16 | Arvinas Operations, Inc. | Rapidly accelerated fibrosarcoma (RAF) degrading compounds and associated methods of use |
Family Cites Families (24)
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PT2275102E (pt) | 2002-03-13 | 2015-10-27 | Array Biopharma Inc | Derivados de benzimidazole alquilado n3 como inibidores de mek |
US7144907B2 (en) | 2003-09-03 | 2006-12-05 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
US7517994B2 (en) | 2003-11-19 | 2009-04-14 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
US7732616B2 (en) | 2003-11-19 | 2010-06-08 | Array Biopharma Inc. | Dihydropyridine and dihydropyridazine derivatives as inhibitors of MEK and methods of use thereof |
WO2005051301A2 (en) | 2003-11-19 | 2005-06-09 | Array Biopharma Inc. | Heterocyclic inhibitors of mek and methods of use thereof |
CA2577275A1 (en) | 2004-08-31 | 2006-03-09 | Astrazeneca Ab | Quinazolinone derivatives and their use as b-raf inhibitors |
AR055057A1 (es) | 2005-05-18 | 2007-08-01 | Array Biopharma Inc | Inhibidores heterociclicos de mek, formas cristalinas de los mismos, procesos para su preparacion y metodos de uso de los mismos en composiciones farmaceuticas y medicamentos para el tratamiento de un trastorno hiperproliferativo o de una condicion inflamatoria. |
US20090170849A1 (en) | 2006-04-05 | 2009-07-02 | Astrazeneca Ab | Quinazolinone derivatives having b-raf inhibitory activity |
WO2007113557A1 (en) | 2006-04-05 | 2007-10-11 | Astrazeneca Ab | Substituted quinazolines with anti-cancer activity |
CN101421253A (zh) | 2006-04-18 | 2009-04-29 | 阿斯利康(瑞典)有限公司 | 喹唑啉-4-酮衍生物、其制备方法及含有它们的药用组合物 |
EP2170830B1 (en) | 2007-07-17 | 2014-10-15 | Plexxikon, Inc. | 2-FLUORO-BENZENESULFONAMIDE COMPOUNDS AS Raf KINASE MODULATORS |
WO2012118492A1 (en) * | 2011-03-01 | 2012-09-07 | Array Biopharma Inc. | Heterocyclic sulfonamides as raf inhibitors |
CN108542906A (zh) | 2011-11-11 | 2018-09-18 | 诺华股份有限公司 | 治疗增生性疾病的方法 |
US10093646B2 (en) | 2014-01-17 | 2018-10-09 | Novartis Ag | 1-pyridazin-/triazin-3-yl-piper(-azine)/idine/pyrolidine derivatives and compositions thereof for inhibiting the activity of SHP2 |
JP6473457B2 (ja) | 2014-01-17 | 2019-02-20 | ノバルティス アーゲー | Shp2の活性を阻害するための1−(トリアジン−3−イル/ピリダジン−3−イル)−ピペリジン/ピペラジン誘導体およびその組成物 |
JO3517B1 (ar) | 2014-01-17 | 2020-07-05 | Novartis Ag | ان-ازاسبيرو الكان حلقي كبديل مركبات اريل-ان مغايرة وتركيبات لتثبيط نشاط shp2 |
CN108779079A (zh) | 2016-01-06 | 2018-11-09 | 特里乌姆治疗公司 | 作为egfr抑制剂的新的氟化喹唑啉衍生物 |
EP3558979B1 (en) | 2016-12-22 | 2021-02-17 | Boehringer Ingelheim International GmbH | Novel benzylamino substituted quinazolines and derivatives as sos1 inhibitors |
JP7394768B2 (ja) * | 2017-09-20 | 2023-12-08 | エイビーエム セラピューティックス コーポレイション | キナーゼ阻害剤としての環状イミノピリミジン誘導体 |
WO2019071351A1 (en) | 2017-10-12 | 2019-04-18 | Trillium Therapeutics Inc. | NOVEL 4-ARYLOXYQUINAZOLINE FLUORIN DERIVATIVES AS EGFR INHIBITORS USEFUL FOR THE TREATMENT OF CANCERS |
EP3694848A1 (en) | 2017-10-12 | 2020-08-19 | Revolution Medicines, Inc. | Pyridine, pyrazine, and triazine compounds as allosteric shp2 inhibitors |
UY38349A (es) | 2018-08-30 | 2020-03-31 | Array Biopharma Inc | Compuestos de pirazolo[3,4-b]piridina como inhibidores de cinasas tam y met |
MX2021002880A (es) | 2018-09-14 | 2021-06-04 | Unilever Ip Holdings B V | Evaluacion de la eficacia de composiciones cosmeticas que no se deben enjuagar para proteger la piel de los contaminantes. |
TWI817018B (zh) * | 2019-06-28 | 2023-10-01 | 美商艾瑞生藥股份有限公司 | 用於治療braf相關的疾病和失調症之化合物 |
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2020
- 2020-06-23 TW TW109121279A patent/TWI817018B/zh active
- 2020-06-24 CA CA3144859A patent/CA3144859C/en active Active
- 2020-06-24 PE PE2021002078A patent/PE20220341A1/es unknown
- 2020-06-24 CR CR20210626A patent/CR20210626A/es unknown
- 2020-06-24 BR BR112021025102A patent/BR112021025102A2/pt unknown
- 2020-06-24 MA MA056387A patent/MA56387A/fr unknown
- 2020-06-24 KR KR1020217042157A patent/KR20220011712A/ko not_active Application Discontinuation
- 2020-06-24 AU AU2020302352A patent/AU2020302352B2/en active Active
- 2020-06-24 JP JP2021576777A patent/JP7169469B2/ja active Active
- 2020-06-24 EP EP20736786.3A patent/EP3990437A1/en active Pending
- 2020-06-24 MX MX2021015903A patent/MX2021015903A/es unknown
- 2020-06-24 CU CU2021000098A patent/CU20210098A7/es unknown
- 2020-06-24 CN CN202080047143.1A patent/CN114026073A/zh active Pending
- 2020-06-24 US US16/910,688 patent/US11414404B2/en active Active
- 2020-06-24 WO PCT/IB2020/055992 patent/WO2020261156A1/en active Application Filing
- 2020-06-26 UY UY0001038767A patent/UY38767A/es unknown
-
2021
- 2021-11-17 IL IL288214A patent/IL288214A/en unknown
- 2021-12-20 CO CONC2021/0017438A patent/CO2021017438A2/es unknown
- 2021-12-28 EC ECSENADI202193541A patent/ECSP21093541A/es unknown
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2022
- 2022-01-27 ZA ZA2022/01329A patent/ZA202201329B/en unknown
- 2022-05-16 US US17/745,346 patent/US11634409B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
US20220289721A1 (en) | 2022-09-15 |
JP2022539056A (ja) | 2022-09-07 |
JP7169469B2 (ja) | 2022-11-10 |
CA3144859C (en) | 2023-09-12 |
MA56387A (fr) | 2022-05-04 |
US20200407344A1 (en) | 2020-12-31 |
IL288214A (en) | 2022-01-01 |
CO2021017438A2 (es) | 2022-01-17 |
CR20210626A (es) | 2022-02-08 |
KR20220011712A (ko) | 2022-01-28 |
CA3144859A1 (en) | 2020-12-30 |
MX2021015903A (es) | 2022-02-03 |
WO2020261156A1 (en) | 2020-12-30 |
BR112021025102A2 (pt) | 2022-01-25 |
TWI817018B (zh) | 2023-10-01 |
CN114026073A (zh) | 2022-02-08 |
AU2020302352A1 (en) | 2022-01-20 |
TW202114996A (zh) | 2021-04-16 |
UY38767A (es) | 2021-01-29 |
ZA202201329B (en) | 2023-09-27 |
US11414404B2 (en) | 2022-08-16 |
ECSP21093541A (es) | 2022-01-31 |
EP3990437A1 (en) | 2022-05-04 |
US11634409B2 (en) | 2023-04-25 |
CU20210098A7 (es) | 2022-06-06 |
AU2020302352B2 (en) | 2023-03-23 |
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