AR113895A1 - Compuestos de heteroarilo sustituidos con alquilamida de piridinsulfona - Google Patents
Compuestos de heteroarilo sustituidos con alquilamida de piridinsulfonaInfo
- Publication number
- AR113895A1 AR113895A1 ARP180103395A ARP180103395A AR113895A1 AR 113895 A1 AR113895 A1 AR 113895A1 AR P180103395 A ARP180103395 A AR P180103395A AR P180103395 A ARP180103395 A AR P180103395A AR 113895 A1 AR113895 A1 AR 113895A1
- Authority
- AR
- Argentina
- Prior art keywords
- substituted
- alkyl
- membered
- hydrogen
- cycloalkyl
- Prior art date
Links
- 150000001875 compounds Chemical group 0.000 title abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 9
- 239000001257 hydrogen Substances 0.000 abstract 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 7
- 125000005842 heteroatom Chemical group 0.000 abstract 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 4
- 125000000623 heterocyclic group Chemical group 0.000 abstract 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 2
- 101150105130 RORB gene Proteins 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 abstract 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 abstract 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 1
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 abstract 1
- 108010081348 HRT1 protein Hairy Proteins 0.000 abstract 1
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 208000037979 autoimmune inflammatory disease Diseases 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
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- 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
- C07D401/14—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 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
- A61K31/495—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
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- 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
- 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
- C07D405/14—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 three or more hetero rings
-
- 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
- C07D417/14—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 three or more hetero rings
-
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Una composición farmacéutica que los comprende y su uso en el tratamiento de enfermedades inflamatorias autoinmunes. Reivindicación 1: Un compuesto caracterizado porque tiene la fórmula (1), en donde Y es N o CR⁶; R¹ es H, CD₃ o C₁₋₃ alquilo; R² es -C(O)R²ᵃ; o C₁₋₆ alquilo, -(CH₂)ʳ-carbociclo de 3 - 14 miembros sustituido con 0 - 1 R²ᵃ o un heterociclo de 5 - 14 miembros que contiene 1 - 4 heteroátomos seleccionados de N, O, y S, sustituido con 0 - 4 R²ᵃ; R²ᵃ, en cada caso, es independientemente hidrógeno, OH, halo, OCF₃, CN, NO₂, -(CH₂)ʳORᵇ, -(CH₂)ʳSRᵇ, -(CH₂)ʳC(O)Rᵇ, -(CH₂)ʳC(O)ORᵇ, -(CH₂)ʳOC(O)Rᵇ, -(CH₂)ʳNR¹¹R¹¹, -(CH₂)ʳC(O)NR¹¹R¹¹, -(CH₂)ʳNRᵇC(O)Rᶜ, -(CH₂)ʳNRᵇC(O)ORᶜ, -NRᵇC(O)NR¹¹R¹¹, -S(O)ₚNR¹¹R¹¹, -NRᵇS(O)ₚRᶜ, -S(O)ₚRᶜ, C₁₋₆ alquilo sustituido con 0 - 3 Rᵃ, C₁₋₆ haloalquilo, C₂₋₆ alquenilo sustituido con 0 - 3 Rᵃ, -(CH₂)ʳ-carbociclo de 3 - 14 miembros sustituido con 0 - 1 Rᵃ o un -(CH₂)ʳ-heterociclo de 5 - 7 miembros que contiene 1 - 4 heteroátomos seleccionados de N, O y S(O)ₚ sustituido con 0 - 2 Rᵃ; R³ es un compuesto de fórmula (2); X está ausente, es O ó NH; R⁴ y R⁵ son independientemente hidrógeno, C₁₋₄ alquilo sustituido con 0 - 1 Rᶠ, (CH₂)ʳ-fenilo sustituido con 0 - 3 Rᵈ o un -(CH₂)-heterociclo de 5 - 7 miembros que contiene 1 - 4 heteroátomos seleccionados de N, O y S(O)ₚ; R⁶ es hidrógeno, halo, C₁₋₄ alquilo, C₁₋₄ alquiloxi, C₁₋₄ haloalquilo, C₁₋₄ haloalcoxi, C₃₋₆ cicloalquilo, CN, NO₂ u OH; R¹¹, en cada caso, es independientemente hidrógeno, C₁₋₄ alquilo sustituido con 0 - 3 Rᶠ, CF₃, C₃₋₁₀ cicloalquilo sustituido con 0 - 1 Rᶠ, (CH₂)ʳ-fenilo sustituido con 0 - 3 Rᵈ o -(CH₂)ʳ-heterociclo de 5 - 7 miembros que contiene 1 - 4 heteroátomos seleccionados de N, O y S(O)ₚ sustituido con 0 - 3 Rᵈ; Rᵃ y Rᵃ¹, en cada caso, son independientemente hidrógeno, F, Cl, Br, OCF₃, CF₃, CHF₂, CN, NO₂, -(CH₂)ʳORᵇ, -(CH₂)ʳSRᵇ, -(CH₂)ʳC(O)Rᵇ, -(CH₂)ʳC(O)ORᵇ, -(CH₂)ʳOC(O)Rᵇ, -(CH₂)ʳNR¹¹R¹¹, -(CH₂)ʳC(O)NR¹¹R¹¹, -(CH₂)ʳNRᵇC(O)Rᶜ, -(CH₂)ʳNRᵇC(O)ORᶜ, -NRᵇC(O)NR¹¹R¹¹, -S(O)ₚNR¹¹R¹¹, -NRᵇS(O)ₚRᶜ, -S(O)Rᶜ, -S(O)₂Rᶜ, C₁₋₆ alquilo sustituido con 0 - 3 Rᶠ, C₁₋₆ haloalquilo, C₂₋₆ alquenilo sustituido con 0 - 3 Rᵃ, C₂₋₆ alquinilo sustituido con 0 - 3 Rᵃ, -(CH₂)ʳ-carbociclo de 3 - 14 miembros o -(CH₂)ʳ-heterociclo de 5 - 7 miembros que contiene 1 - 4 heteroátomos seleccionados de N, O y S(O)ₚ sustituido con 0 - 3 Rᶠ; Rᵇ es hidrógeno, C₁₋₆ alquilo sustituido con 0 - 3 Rᵈ, C₁₋₆ haloalquilo, C₃₋₆ cicloalquilo sustituido con 0 - 2 Rᵈ o -(CH₂)ʳ-heterociclo de 5 - 7 miembros que contiene 1 - 4 heteroátomos seleccionados de N, O y S(O)ₚ sustituido con 0 - 3 Rᶠ, o (CH₂)ʳ-fenilo sustituido con 0 - 3 Rᵈ; Rᶜ es C₁₋₆ alquilo sustituido con 0 - 3 Rᶠ, (CH₂)ʳ-C₃₋₆ cicloalquilo sustituido con 0 - 3 Rᶠ o (CH₂)ʳ-fenilo sustituido con 0 - 3 Rᶠ; Rᵈ es independientemente, en cada caso, hidrógeno, F, Cl, Br, OCF₃, CF₃, CN, NO₂, -ORᵉ, -(CH₂)ʳC(O)Rᶜ, -NRᵉRᵉ, -NRᵉC(O)ORᶜ, C₁₋₆, alquilo o (CH₂)ʳ-fenilo sustituido con 0 - 3 Rᶠ; Rᵉ es independientemente, en cada caso, hidrógeno, C₁₋₆ alquilo, C₃₋₆ cicloalquilo o (CH₂)ʳ-fenilo sustituido con 0 - 3 Rᶠ; Rᶠ es independientemente, en cada caso, hidrógeno, halo, CN, NH₂, OH, C₃₋₆ cicloalquilo, CF₃, O(C₁₋₆ alquilo) o un -(CH₂)ʳ-heterociclo de 5 - 7 miembros que contiene 1 - 4 heteroátomos seleccionados de N, O y S(O)ₚ; p es 0, 1 ó 2; r es 0, 1, 2, 3 ó 4; o un estereoisómero o una sal de aquel aceptable desde el punto de vista farmacéutico.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201762589165P | 2017-11-21 | 2017-11-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
AR113895A1 true AR113895A1 (es) | 2020-06-24 |
Family
ID=65036887
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ARP180103395A AR113895A1 (es) | 2017-11-21 | 2018-11-20 | Compuestos de heteroarilo sustituidos con alquilamida de piridinsulfona |
Country Status (19)
Country | Link |
---|---|
US (3) | US11021462B2 (es) |
EP (1) | EP3713930A1 (es) |
JP (2) | JP7258903B2 (es) |
KR (1) | KR102702228B1 (es) |
CN (1) | CN111315737B (es) |
AR (1) | AR113895A1 (es) |
AU (3) | AU2018371010C1 (es) |
BR (1) | BR112020009606A2 (es) |
CA (1) | CA3083122A1 (es) |
CL (1) | CL2020001338A1 (es) |
CO (1) | CO2020006139A2 (es) |
EA (1) | EA202091269A1 (es) |
IL (1) | IL274816B2 (es) |
MX (1) | MX2020005210A (es) |
PE (1) | PE20211461A1 (es) |
SG (1) | SG11202004592TA (es) |
TW (1) | TWI776994B (es) |
WO (1) | WO2019103952A1 (es) |
ZA (1) | ZA202003717B (es) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2018371010C1 (en) * | 2017-11-21 | 2024-09-26 | Bristol-Myers Squibb Company | Sulfone pyridine alkyl amide-substituted heteroaryl compounds |
CN111484480B (zh) * | 2019-01-29 | 2023-08-11 | 上海翰森生物医药科技有限公司 | 一种多环类衍生物抑制剂、其制备方法和应用 |
JP2022542704A (ja) * | 2019-08-01 | 2022-10-06 | インテグラル バイオサイエンシーズ プライベート リミテッド | キナーゼインヒビターとしての複素環式化合物およびその使用 |
CN115160297B (zh) * | 2020-12-22 | 2023-03-31 | 益方生物科技(上海)股份有限公司 | 杂芳基化合物及其制备方法和用途 |
BR112023016614A2 (pt) | 2021-02-19 | 2023-11-07 | Sudo Biosciences Ltd | Inibidores de tyk2 e usos dos mesmos |
EP4294807A1 (en) | 2021-02-19 | 2023-12-27 | Sudo Biosciences Limited | Tyk2 inhibitors and uses thereof |
US20240182429A1 (en) * | 2021-03-30 | 2024-06-06 | Zhejiang Wenda Pharma Technology Ltd. | Heterocyclic compound as tyk2 pseudokinase domain inhibitor, synthetic method, and use |
JP2024518792A (ja) * | 2021-05-14 | 2024-05-02 | ブリストル-マイヤーズ スクイブ カンパニー | 置換ヘテロ環化合物 |
CN116693449A (zh) | 2022-03-04 | 2023-09-05 | 上海致根医药科技有限公司 | 用作tyk2抑制剂的化合物、其制备方法及其在医药上的应用 |
WO2024125651A1 (zh) * | 2022-12-16 | 2024-06-20 | 津药生物科技(天津)有限公司 | 新型含杂环取代的丙烯酸衍生物及其用途 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20140108594A (ko) | 2012-01-10 | 2014-09-11 | 에프. 호프만-라 로슈 아게 | 피리다진 아미드 화합물 및 syk 저해제로서의 이의 용도 |
WO2014060371A1 (en) | 2012-10-19 | 2014-04-24 | F. Hoffmann-La Roche Ag | Inhibitors of syk |
AU2013341185B2 (en) * | 2012-11-08 | 2017-07-13 | Bristol-Myers Squibb Company | Alkyl-amide-substituted pyridyl compounds useful as modulators of IL-12, IL-23 and/or IFNalpha responses |
RS63328B1 (sr) * | 2012-11-08 | 2022-07-29 | Bristol Myers Squibb Co | Amidom-supstituisana heterociklična jedinjenja korisna kao modulatori il-12, il-23 i/ili ifn alfa odgovora |
AR094537A1 (es) * | 2013-11-07 | 2015-08-12 | Bristol Myers Squibb Co | COMPUESTOS DE PIRIDILO SUSTITUIDOS CON ALQUILAMIDA ÚTILES COMO MODULADORES DE LAS RESPUESTAS DE IL-12, IL-23 Y/O IFNa |
JP6345786B2 (ja) | 2013-12-05 | 2018-06-20 | ファーマサイクリックス エルエルシー | ブルトン型チロシンキナーゼの阻害剤 |
TW201827423A (zh) | 2016-12-13 | 2018-08-01 | 美商必治妥美雅史谷比公司 | 做為IL-12, IL-23及/或IFNα反應調節劑之經烷基醯胺取代之雜芳基化合物氧化膦 |
AU2018371010C1 (en) * | 2017-11-21 | 2024-09-26 | Bristol-Myers Squibb Company | Sulfone pyridine alkyl amide-substituted heteroaryl compounds |
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2018
- 2018-11-19 AU AU2018371010A patent/AU2018371010C1/en active Active
- 2018-11-19 EP EP18836556.3A patent/EP3713930A1/en active Pending
- 2018-11-19 BR BR112020009606-7A patent/BR112020009606A2/pt unknown
- 2018-11-19 EA EA202091269A patent/EA202091269A1/ru unknown
- 2018-11-19 SG SG11202004592TA patent/SG11202004592TA/en unknown
- 2018-11-19 PE PE2020000703A patent/PE20211461A1/es unknown
- 2018-11-19 IL IL274816A patent/IL274816B2/en unknown
- 2018-11-19 JP JP2020545054A patent/JP7258903B2/ja active Active
- 2018-11-19 WO PCT/US2018/061726 patent/WO2019103952A1/en unknown
- 2018-11-19 MX MX2020005210A patent/MX2020005210A/es unknown
- 2018-11-19 KR KR1020207017459A patent/KR102702228B1/ko active IP Right Grant
- 2018-11-19 CA CA3083122A patent/CA3083122A1/en active Pending
- 2018-11-19 CN CN201880072389.7A patent/CN111315737B/zh active Active
- 2018-11-20 US US16/195,951 patent/US11021462B2/en active Active
- 2018-11-20 TW TW107141159A patent/TWI776994B/zh active
- 2018-11-20 AR ARP180103395A patent/AR113895A1/es unknown
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2020
- 2020-05-19 CO CONC2020/0006139A patent/CO2020006139A2/es unknown
- 2020-05-20 CL CL2020001338A patent/CL2020001338A1/es unknown
- 2020-06-19 ZA ZA2020/03717A patent/ZA202003717B/en unknown
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2021
- 2021-04-28 US US17/242,428 patent/US11787779B2/en active Active
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2022
- 2022-09-06 AU AU2022228101A patent/AU2022228101B2/en active Active
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2023
- 2023-04-05 JP JP2023061359A patent/JP7490107B2/ja active Active
- 2023-09-05 US US18/461,093 patent/US20240002364A1/en active Pending
- 2023-10-27 AU AU2023255024A patent/AU2023255024A1/en active Pending
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