PE20221283A1 - Compuestos triciclicos sustituidos - Google Patents
Compuestos triciclicos sustituidosInfo
- Publication number
- PE20221283A1 PE20221283A1 PE2022001331A PE2022001331A PE20221283A1 PE 20221283 A1 PE20221283 A1 PE 20221283A1 PE 2022001331 A PE2022001331 A PE 2022001331A PE 2022001331 A PE2022001331 A PE 2022001331A PE 20221283 A1 PE20221283 A1 PE 20221283A1
- Authority
- PE
- Peru
- Prior art keywords
- substituted
- unsubstituted
- cycloalkyl
- alkyl
- amino
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- MEUGSNBOYROBOF-SNVBAGLBSA-N 4-[[(1R)-1-[3-amino-5-(trifluoromethyl)phenyl]ethyl]amino]-2,6-dimethylpyrimido[5,4-g][1,4]benzoxazin-7-one Chemical compound NC=1C=C(C=C(C=1)C(F)(F)F)[C@@H](C)NC1=NC(=NC2=CC3=C(C=C12)N(C(CO3)=O)C)C MEUGSNBOYROBOF-SNVBAGLBSA-N 0.000 abstract 1
- 125000001054 5 membered carbocyclic group Chemical group 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004008 6 membered carbocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 101100404726 Arabidopsis thaliana NHX7 gene Proteins 0.000 abstract 1
- 208000035473 Communicable disease Diseases 0.000 abstract 1
- WKEUOIJSEBKOJQ-GFCCVEGCSA-N FC(C(C)(C)O)(F)C=1C(=C(C=CC=1)[C@@H](C)NC1=NC(=NC2=CC3=C(C=C12)N(C(CO3)=O)C)C)F Chemical compound FC(C(C)(C)O)(F)C=1C(=C(C=CC=1)[C@@H](C)NC1=NC(=NC2=CC3=C(C=C12)N(C(CO3)=O)C)C)F WKEUOIJSEBKOJQ-GFCCVEGCSA-N 0.000 abstract 1
- WFXAEYOBJFAFSJ-LLVKDONJSA-N FC(CO)(F)C=1C(=C(C=CC=1)[C@@H](C)NC1=NC(=NC2=CC3=C(C=C12)N(C(CO3)=O)C)C)F Chemical compound FC(CO)(F)C=1C(=C(C=CC=1)[C@@H](C)NC1=NC(=NC2=CC3=C(C=C12)N(C(CO3)=O)C)C)F WFXAEYOBJFAFSJ-LLVKDONJSA-N 0.000 abstract 1
- 102000057028 SOS1 Human genes 0.000 abstract 1
- 108700022176 SOS1 Proteins 0.000 abstract 1
- 101100197320 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) RPL35A gene Proteins 0.000 abstract 1
- 101150100839 Sos1 gene Proteins 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 208000015181 infectious disease Diseases 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- -1 perhaloalkyl Chemical group 0.000 abstract 1
- 230000002062 proliferating effect Effects 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
Classifications
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- 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
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—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
- A61K31/495—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
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5383—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- 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
- C07D487/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/20—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/20—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Referida a un compuesto de formula general (I), donde: el anillo A se selecciona entre arilo, heteroarilo y heterociclilo; el anillo B es un anillo carbociclico de 5 o 6 miembros 10 sustituido o no sustituido y un anillo heterociclico de 5 o 6 miembros sustituido o no sustituido que contiene de 1 a 3 heteroatomos seleccionados independientemente entre S, O y N; R1 es hidrogeno, alquilo sustituido o no sustituido y cicloalquilo sustituido o no sustituido; R2 y R3 son hidrogeno, halogeno, ciano, alquilo sustituido o no sustituido y cicloalquilo sustituido o no sustituido; R4 es halogeno, ciano, entre otros; "n" es un numero entero seleccionado entre 0, 1, 2 y 3; R5 es hidrogeno, alquilo, perhaloalquilo y cicloalquilo; R6 es hidrogeno, alquilo y cicloalquilo; o R6 junto con el nitrogeno al que estan unidos, forman un anillo de heterociclilo; y R7 es alquilo y cicloalquilo. Son compuestos preferidos: (R)-4-((1-(3-amino-5-(trifluorometil)fenil)etil)amino)-2,6-dimetil-6H- [1,4]oxazino[3,2-g]quinazolin-7(8H)-ona; (R)-4-((1-(3-(1,1-difluoro-2-hidroxietil)-2-fluorofenil)etil)amino)-2,6-dimetil6H-[1,4]oxazino[3,2-g]quinazolin-7(8H)-ona; (R)-4-((1-(3-(1,1-difluoro-2-hidroxi-2-metilpropil)-2-fluorofenil)etil)amino)- 2,6-dimetil-6H-[1,4]oxazino[3,2-g]quinazolin-7(8H)-ona; entre otros. Dichos compuestos son inhibidores de SOS1 y son utiles en el tratamiento de enfermedades o trastornos proliferativos, infecciosos y RASopatias.
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN201921054254 | 2019-12-27 | ||
| IN201921049099 | 2019-12-29 | ||
| IN202021022668 | 2020-05-29 | ||
| IN202021032769 | 2020-07-30 | ||
| IN202021035200 | 2020-08-14 | ||
| PCT/IB2020/062462 WO2021130731A1 (en) | 2019-12-27 | 2020-12-27 | Substituted tricyclic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20221283A1 true PE20221283A1 (es) | 2022-09-05 |
Family
ID=74184675
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2022001331A PE20221283A1 (es) | 2019-12-27 | 2020-12-27 | Compuestos triciclicos sustituidos |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US20230119316A1 (es) |
| EP (1) | EP4081521B1 (es) |
| JP (1) | JP7642647B2 (es) |
| KR (1) | KR20220132543A (es) |
| CN (1) | CN115605476B (es) |
| AU (1) | AU2020412429B2 (es) |
| BR (1) | BR112022012641A2 (es) |
| CA (1) | CA3165864A1 (es) |
| CL (1) | CL2022001739A1 (es) |
| CO (1) | CO2022010460A2 (es) |
| CR (1) | CR20220363A (es) |
| EC (1) | ECSP22058816A (es) |
| GE (2) | GEP20247653B (es) |
| IL (1) | IL294198A (es) |
| MX (1) | MX2022008066A (es) |
| PE (1) | PE20221283A1 (es) |
| PH (1) | PH12022551585A1 (es) |
| SA (1) | SA522433155B1 (es) |
| WO (1) | WO2021130731A1 (es) |
| ZA (1) | ZA202207722B (es) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL312367A (en) | 2017-01-31 | 2024-06-01 | Arvinas Operations Inc | Cereblon ligands and bifunctional compounds comprising the same |
| SG11202012922VA (en) | 2018-07-09 | 2021-01-28 | Boehringer Ingelheim Animal Health Usa Inc | Anthelminthic heterocyclic compounds |
| CA3165168A1 (en) | 2019-12-19 | 2021-06-24 | Arvinas Operations, Inc. | Compounds and methods for the targeted degradation of androgen receptor |
| CR20220665A (es) | 2020-05-29 | 2023-07-19 | Boehringer Ingelheim Pharma | Compuestos heterocíclicos como anthelmínticos |
| US11690915B2 (en) | 2020-09-15 | 2023-07-04 | Revolution Medicines, Inc. | Ras inhibitors |
| KR20230093300A (ko) * | 2020-10-20 | 2023-06-27 | 쑤저우 젤겐 바이오파마슈티칼즈 컴퍼니 리미티드 | 치환된 벤조 또는 피리도피리미딘 아민계 억제제 및 이의 제조 방법과 응용 |
| WO2022121813A1 (zh) * | 2020-12-07 | 2022-06-16 | 北京泰德制药股份有限公司 | Sos1抑制剂、包含其的药物组合物及其用途 |
| MX2023008460A (es) * | 2021-01-19 | 2023-09-12 | Lupin Ltd | Combinaciones farmacéuticas de inhibidores de sos1 para el tratamiento y/o prevención del cáncer. |
| CN114835719A (zh) * | 2021-02-01 | 2022-08-02 | 苏州泽璟生物制药股份有限公司 | 取代双环并芳杂环胺类抑制剂及其制备方法和应用 |
| MX2023011633A (es) | 2021-03-31 | 2023-12-15 | Sevenless Therapeutics Ltd | Inhibidores de sos1 e inhibidores de ras para su uso en el tratamiento del dolor. |
| CN117479942A (zh) | 2021-04-09 | 2024-01-30 | 勃林格殷格翰国际有限公司 | 抗癌疗法 |
| TWI807787B (zh) * | 2021-04-19 | 2023-07-01 | 大陸商昆藥集團股份有限公司 | 苯並嘧啶三環衍生物及製備方法和應用 |
| AR127308A1 (es) | 2021-10-08 | 2024-01-10 | Revolution Medicines Inc | Inhibidores ras |
| PE20250675A1 (es) | 2021-11-01 | 2025-03-04 | Boehringer Ingelheim Vetmedica Gmbh | Compuestos de pirrolopiridazina como antihelminticos |
| CN115536660B (zh) * | 2021-11-04 | 2025-09-02 | 北京福元医药股份有限公司 | 苄氨基取代的杂多环化合物及其组合物、制剂和用途 |
| US20250282782A1 (en) | 2021-12-17 | 2025-09-11 | Genzyme Corporation | Pyrazolopyrazine compounds as shp2 inhibitors |
| WO2023109929A1 (zh) * | 2021-12-17 | 2023-06-22 | 石药集团中奇制药技术（石家庄）有限公司 | 一种具有抗肿瘤活性的杂环化合物及其用途 |
| WO2023135260A1 (en) | 2022-01-14 | 2023-07-20 | Jazz Pharmaceuticals Ireland Limited | Novel amine-substituted phthalazines and derivatives as sos1 inhibitors |
| KR20230121208A (ko) * | 2022-02-10 | 2023-08-18 | (주)파로스아이바이오 | Sos1 억제제 및 이의 유도체 |
| EP4227307A1 (en) | 2022-02-11 | 2023-08-16 | Genzyme Corporation | Pyrazolopyrazine compounds as shp2 inhibitors |
| WO2023165438A1 (zh) * | 2022-03-03 | 2023-09-07 | 浙江海正药业股份有限公司 | 三环类衍生物及其制备方法和用途 |
| GB202203976D0 (en) | 2022-03-22 | 2022-05-04 | Jazz Pharmaceuticals Ireland Ltd | Tricyclic phthalazines and derivatives as sos1 inhibitors |
| KR20250040894A (ko) | 2022-05-25 | 2025-03-25 | 이케나 온콜로지, 인코포레이티드 | Mek 억제제 및 이의 용도 |
| EP4536364A1 (en) | 2022-06-10 | 2025-04-16 | Revolution Medicines, Inc. | Macrocyclic ras inhibitors |
| KR20260005904A (ko) | 2023-04-07 | 2026-01-12 | 레볼루션 메디슨즈, 인크. | 매크로사이클릭 ras 억제제 |
| WO2024211712A1 (en) | 2023-04-07 | 2024-10-10 | Revolution Medicines, Inc. | Condensed macrocyclic compounds as ras inhibitors |
| AU2024252105A1 (en) | 2023-04-14 | 2025-10-16 | Revolution Medicines, Inc. | Crystalline forms of ras inhibitors, compositions containing the same, and methods of use thereof |
| AU2024251341A1 (en) | 2023-04-14 | 2025-10-16 | Revolution Medicines, Inc. | Crystalline forms of a ras inhibitor |
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| JOP20190221A1 (ar) | 2017-04-05 | 2019-09-23 | Seal Rock Therapeutics Inc | مركبات مثبطات كيناز منظم لإشارات الاستماتة 1 (ask1) واستخداماتها |
| TWI870922B (zh) * | 2017-12-21 | 2025-01-21 | 德商百靈佳殷格翰國際股份有限公司 | 作為sos1抑制劑之新穎芐胺基取代吡啶并嘧啶酮及衍生物 |
| US20220274979A1 (en) | 2018-04-18 | 2022-09-01 | Bayer Pharma Aktiengesellschaft | 2-methyl-aza-quinazolines |
| WO2019243823A1 (en) | 2018-06-21 | 2019-12-26 | Curadev Pharma Limited | Azaheterocyclic small molecule modulators of human sting |
| AU2020232616A1 (en) | 2019-03-01 | 2021-09-09 | Revolution Medicines, Inc. | Bicyclic heterocyclyl compounds and uses thereof |
| WO2020180768A1 (en) | 2019-03-01 | 2020-09-10 | Revolution Medicines, Inc. | Bicyclic heteroaryl compounds and uses thereof |
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2020
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- 2020-12-27 BR BR112022012641A patent/BR112022012641A2/pt unknown
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- 2020-12-27 JP JP2022539232A patent/JP7642647B2/ja active Active
- 2020-12-27 WO PCT/IB2020/062462 patent/WO2021130731A1/en not_active Ceased
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| SA522433155B1 (ar) | 2025-04-20 |
| BR112022012641A2 (pt) | 2022-09-06 |
| JP7642647B2 (ja) | 2025-03-10 |
| GEAP202416015A (en) | 2024-04-10 |
| GEP20247653B (en) | 2024-08-12 |
| KR20220132543A (ko) | 2022-09-30 |
| EP4081521A1 (en) | 2022-11-02 |
| IL294198A (en) | 2022-08-01 |
| ECSP22058816A (es) | 2022-08-31 |
| AU2020412429A1 (en) | 2022-08-18 |
| CL2022001739A1 (es) | 2023-03-31 |
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| EP4081521B1 (en) | 2025-12-10 |
| MX2022008066A (es) | 2022-08-15 |
| PH12022551585A1 (en) | 2023-11-29 |
| CN115605476B (zh) | 2024-05-24 |
| CN115605476A (zh) | 2023-01-13 |
| AU2020412429B2 (en) | 2025-12-04 |
| CO2022010460A2 (es) | 2022-08-09 |
| ZA202207722B (en) | 2023-03-29 |
| CA3165864A1 (en) | 2021-07-01 |
| CR20220363A (es) | 2022-09-23 |
| WO2021130731A1 (en) | 2021-07-01 |
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