MX2020004785A - Proceso para preparar tapinarof. - Google Patents
Proceso para preparar tapinarof.Info
- Publication number
- MX2020004785A MX2020004785A MX2020004785A MX2020004785A MX2020004785A MX 2020004785 A MX2020004785 A MX 2020004785A MX 2020004785 A MX2020004785 A MX 2020004785A MX 2020004785 A MX2020004785 A MX 2020004785A MX 2020004785 A MX2020004785 A MX 2020004785A
- Authority
- MX
- Mexico
- Prior art keywords
- isopropyl
- stilbene
- dihydroxy
- trans
- tapinarof
- Prior art date
Links
- ZISJNXNHJRQYJO-CMDGGOBGSA-N 5-[(e)-2-phenylethenyl]-2-propan-2-ylbenzene-1,3-diol Chemical compound C1=C(O)C(C(C)C)=C(O)C=C1\C=C\C1=CC=CC=C1 ZISJNXNHJRQYJO-CMDGGOBGSA-N 0.000 title abstract 4
- 238000004519 manufacturing process Methods 0.000 title 1
- 229940070118 tapinarof Drugs 0.000 title 1
- 150000003839 salts Chemical class 0.000 abstract 2
- 239000012453 solvate Substances 0.000 abstract 2
- -1 (E)-2-chloro-2-isopropyl-5-styrylcyclohexane Chemical compound 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/08—Dihydroxy benzenes; Alkylated derivatives thereof
-
- 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
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/05—Phenols
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
- C07C37/002—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by transformation of a functional group, e.g. oxo, carboxyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/06—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation
- C07C37/07—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation with simultaneous reduction of C=O group in that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/205—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings
- C07C39/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/213—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C49/217—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/683—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings having unsaturation outside the aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/24—Quinones containing halogen
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
- C07C51/38—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by decarboxylation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/347—Saturated compounds containing more than one carboxyl group containing keto groups
- C07C59/353—Saturated compounds containing more than one carboxyl group containing keto groups containing rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Compounds Of Unknown Constitution (AREA)
- Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
La presente invención proporciona procesos para la preparación de 3,5-dihidroxi-4-isopropil-trans-estilbeno o una sal o solvato del mismo y nuevos productos intermedios usados en el mismo. En algunas modalidades, el 3,5-dihidroxi-4-isopropil-trans-estilbeno se prepara a partir de (E)-2-cloro-2-isopropil-5-estirilciclohexan o-5 1,3-diona. También se describen formas cristalinas de 3,5-dihidroxi-4-isopropil-trans-estilbeno o una sal o solvato del mismo y composiciones farmacéuticas que lo comprenden.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201762584192P | 2017-11-10 | 2017-11-10 | |
PCT/US2018/060749 WO2019094934A1 (en) | 2017-11-10 | 2018-11-13 | Process for preparing tapinarof |
Publications (1)
Publication Number | Publication Date |
---|---|
MX2020004785A true MX2020004785A (es) | 2020-08-13 |
Family
ID=66431171
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
MX2020004785A MX2020004785A (es) | 2017-11-10 | 2018-11-13 | Proceso para preparar tapinarof. |
MX2022015106A MX2022015106A (es) | 2017-11-10 | 2020-07-13 | Proceso para preparar tapinarof. |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
MX2022015106A MX2022015106A (es) | 2017-11-10 | 2020-07-13 | Proceso para preparar tapinarof. |
Country Status (14)
Country | Link |
---|---|
US (4) | US10647649B2 (es) |
EP (1) | EP3706725A4 (es) |
JP (5) | JP6912664B2 (es) |
KR (1) | KR20200087786A (es) |
CN (1) | CN111511357B (es) |
AU (2) | AU2018365241B2 (es) |
BR (1) | BR112020009158A2 (es) |
CA (1) | CA3082115A1 (es) |
CL (2) | CL2020001226A1 (es) |
CO (1) | CO2020007018A2 (es) |
IL (2) | IL304090A (es) |
MX (2) | MX2020004785A (es) |
SG (1) | SG11202002576TA (es) |
WO (1) | WO2019094934A1 (es) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11617724B2 (en) | 2015-05-21 | 2023-04-04 | Dermavant Sciences GmbH | Topical pharmaceutical compositions |
JP6863904B2 (ja) | 2015-05-21 | 2021-04-21 | ダーマバント、サイエンシーズ、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツングDermavant Sciences Gmbh | 局所用医薬組成物 |
WO2019094934A1 (en) | 2017-11-10 | 2019-05-16 | Dermavant Sciences GmbH | Process for preparing tapinarof |
US11497718B2 (en) | 2018-11-13 | 2022-11-15 | Dermavant Sciences GmbH | Use of tapinarof for the treatment of atopic dermatitis |
JP2023523213A (ja) * | 2020-04-22 | 2023-06-02 | イッサム リサーチ ディべロップメント カンパニー オブ ザ ヘブライ ユニバーシティー オブ エルサレム,リミテッド | 生理活性フェノラートイオン性錯体 |
EP4153551A1 (en) | 2020-05-19 | 2023-03-29 | Teva Pharmaceuticals International GmbH | Solid state forms of tapinarof |
WO2022109626A1 (en) * | 2020-11-23 | 2022-05-27 | Dermavant Sciences GmbH | Gel, ointment, and foam formulations of tapinarof and methods of use |
CN115703700A (zh) * | 2021-08-03 | 2023-02-17 | 北京颖泰嘉和生物科技股份有限公司 | 1,3-环己二酮的制备方法 |
WO2023067606A1 (en) * | 2021-10-21 | 2023-04-27 | Sol-Gel Technologies Ltd. | Crystalline polymorph of tapinarof |
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JP6863904B2 (ja) * | 2015-05-21 | 2021-04-21 | ダーマバント、サイエンシーズ、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツングDermavant Sciences Gmbh | 局所用医薬組成物 |
US11617724B2 (en) | 2015-05-21 | 2023-04-04 | Dermavant Sciences GmbH | Topical pharmaceutical compositions |
CN111148729A (zh) | 2017-09-30 | 2020-05-12 | 北京文丰天济医药科技有限公司 | 苯烯莫德的晶型及其用途与制备方法 |
WO2019094934A1 (en) | 2017-11-10 | 2019-05-16 | Dermavant Sciences GmbH | Process for preparing tapinarof |
EP4153551A1 (en) | 2020-05-19 | 2023-03-29 | Teva Pharmaceuticals International GmbH | Solid state forms of tapinarof |
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2018
- 2018-11-13 WO PCT/US2018/060749 patent/WO2019094934A1/en unknown
- 2018-11-13 BR BR112020009158-8A patent/BR112020009158A2/pt unknown
- 2018-11-13 MX MX2020004785A patent/MX2020004785A/es unknown
- 2018-11-13 CN CN201880071224.8A patent/CN111511357B/zh active Active
- 2018-11-13 SG SG11202002576TA patent/SG11202002576TA/en unknown
- 2018-11-13 IL IL304090A patent/IL304090A/en unknown
- 2018-11-13 EP EP18875722.3A patent/EP3706725A4/en active Pending
- 2018-11-13 KR KR1020207016222A patent/KR20200087786A/ko not_active Application Discontinuation
- 2018-11-13 IL IL274439A patent/IL274439B2/en unknown
- 2018-11-13 AU AU2018365241A patent/AU2018365241B2/en active Active
- 2018-11-13 JP JP2020523700A patent/JP6912664B2/ja active Active
- 2018-11-13 CA CA3082115A patent/CA3082115A1/en active Pending
- 2018-11-13 US US16/189,268 patent/US10647649B2/en active Active
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2020
- 2020-04-15 US US16/849,346 patent/US10961175B2/en active Active
- 2020-05-08 CL CL2020001226A patent/CL2020001226A1/es unknown
- 2020-06-09 CO CONC2020/0007018A patent/CO2020007018A2/es unknown
- 2020-07-13 MX MX2022015106A patent/MX2022015106A/es unknown
- 2020-12-25 JP JP2020216295A patent/JP2021063100A/ja active Pending
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2021
- 2021-02-12 US US17/174,566 patent/US11597692B2/en active Active
- 2021-07-08 JP JP2021113606A patent/JP7166399B2/ja active Active
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2022
- 2022-09-16 JP JP2022148508A patent/JP2023002516A/ja active Pending
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2023
- 2023-01-16 CL CL2023000154A patent/CL2023000154A1/es unknown
- 2023-02-03 US US18/164,309 patent/US20230174445A1/en active Pending
- 2023-12-04 AU AU2023274224A patent/AU2023274224A1/en active Pending
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2024
- 2024-02-19 JP JP2024022828A patent/JP2024069233A/ja active Pending
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