CO2022018295A2 - 2-oxoimidazolidin-4-carboxamidas como inhibidores de nav1.8 - Google Patents
2-oxoimidazolidin-4-carboxamidas como inhibidores de nav1.8Info
- Publication number
- CO2022018295A2 CO2022018295A2 CONC2022/0018295A CO2022018295A CO2022018295A2 CO 2022018295 A2 CO2022018295 A2 CO 2022018295A2 CO 2022018295 A CO2022018295 A CO 2022018295A CO 2022018295 A2 CO2022018295 A2 CO 2022018295A2
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- Colombia
- Prior art keywords
- disorders
- inhibitors
- prevention
- management
- useful
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- 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
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- 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
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- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
-
- 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
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
-
- 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
- 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
-
- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen 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
- 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
- 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
- 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
- C07D471/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Nuevos compuestos de la fórmula estructural (I), y las sales farmacéuticamente aceptables de los mismos, son inhibidores de la actividad de los canales Nav1.8 y pueden ser útiles en el tratamiento, prevención, gestión, mejoría, control y supresión de enfermedades mediadas por la actividad de los canales Nav1.8. Los compuestos de la presente invención pueden ser útiles en el tratamiento, prevención o gestión de trastornos de dolor, trastornos de tos, trastornos de picazón aguda y trastornos de picazón crónica.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US202063040461P | 2020-06-17 | 2020-06-17 | |
PCT/US2021/037303 WO2021257490A1 (en) | 2020-06-17 | 2021-06-15 | 2-oxoimidazolidine-4-carboxamides as nav1.8 inhibitors |
Publications (1)
Publication Number | Publication Date |
---|---|
CO2022018295A2 true CO2022018295A2 (es) | 2022-12-20 |
Family
ID=76829646
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CONC2022/0018295A CO2022018295A2 (es) | 2020-06-17 | 2022-12-15 | 2-oxoimidazolidin-4-carboxamidas como inhibidores de nav1.8 |
Country Status (19)
Country | Link |
---|---|
US (2) | US11802122B2 (es) |
EP (1) | EP4168393A1 (es) |
JP (3) | JP7323723B2 (es) |
KR (1) | KR20230024985A (es) |
CN (1) | CN116134018A (es) |
AR (1) | AR122628A1 (es) |
AU (1) | AU2021293176A1 (es) |
BR (1) | BR112022025805A2 (es) |
CA (1) | CA3182633A1 (es) |
CL (1) | CL2022003544A1 (es) |
CO (1) | CO2022018295A2 (es) |
CR (1) | CR20220642A (es) |
DO (1) | DOP2022000290A (es) |
EC (1) | ECSP23003443A (es) |
IL (1) | IL299180A (es) |
MX (1) | MX2022015581A (es) |
PE (1) | PE20231383A1 (es) |
TW (1) | TWI806073B (es) |
WO (1) | WO2021257490A1 (es) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP4334293A1 (en) * | 2021-05-07 | 2024-03-13 | Merck Sharp & Dohme LLC | Cycloalkyl 3-oxopiperazine carboxamides and cycloheteroalkyl 3-oxopiperazine carboxamides as nav1.8 inhibitors |
IL308953A (en) | 2021-06-04 | 2024-01-01 | Vertex Pharma | N-Hydroalkyl(Hetero)Aryl)Tetrahydrofuran Carboxamides as Natrene Channel Modulators |
CN117794918A (zh) | 2021-06-04 | 2024-03-29 | 沃泰克斯药物股份有限公司 | 经取代的四氢呋喃类似物作为钠通道调节剂 |
CA3221939A1 (en) | 2021-06-04 | 2022-12-08 | Vertex Pharmaceuticals Incorporated | N-(hydroxyalkyl (hetero)aryl) tetrahydrofuran carboxamide analogs as modulators of sodium channels |
JP2024520649A (ja) | 2021-06-04 | 2024-05-24 | バーテックス ファーマシューティカルズ インコーポレイテッド | (2r,3s,4s,5r)-4-[[3-(3,4-ジフルオロ-2-メトキシ-フェニル)-4,5-ジメチル-5-(トリフルオロメチル)テトラヒドロフラン-2-カルボニル]アミノ]ピリジン-2-カルボキサミドを含む固体剤形及び投与レジメン |
CA3221788A1 (en) | 2021-06-04 | 2022-12-08 | Vertex Pharmaceuticals Incorporated | Substituted tetrahydrofuran-2-carboxamides as modulators of sodium channels |
AU2022286511A1 (en) | 2021-06-04 | 2023-11-30 | Vertex Pharmaceuticals Incorporated | Hydroxy and (halo)alkoxy substituted tetrahydrofurans as modulators of sodium channels |
WO2023205468A1 (en) | 2022-04-22 | 2023-10-26 | Vertex Pharmaceuticals Incorporated | Heteroaryl compounds for the treatment of pain |
WO2023205463A1 (en) | 2022-04-22 | 2023-10-26 | Vertex Pharmaceuticals Incorporated | Heteroaryl compounds for the treatment of pain |
WO2023205465A1 (en) | 2022-04-22 | 2023-10-26 | Vertex Pharmaceuticals Incorporated | Heteroaryl compounds for the treatment of pain |
TW202408501A (zh) | 2022-04-22 | 2024-03-01 | 美商維泰克斯製藥公司 | 用於治療疼痛之雜芳基化合物 |
WO2023211990A1 (en) | 2022-04-25 | 2023-11-02 | Siteone Therapeutics, Inc. | Bicyclic heterocyclic amide inhibitors of na v1.8 for the treatment of pain |
WO2024123815A1 (en) | 2022-12-06 | 2024-06-13 | Vertex Pharmaceuticals Incorporated | Process for the synthesis of substituted tetrahydrofuran modulators of sodium channels |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BRPI0809930A2 (pt) * | 2007-04-03 | 2014-10-07 | Glaxo Group Ltd | Derivados de carboxamida imidazolidina como moduladores de p2x7 |
MX2010003866A (es) | 2007-10-11 | 2010-06-01 | Vertex Pharma | Heteroaril amidas utiles como inhibidores de canales de sodio dependientes de voltaje. |
US8389734B2 (en) | 2007-10-11 | 2013-03-05 | Vertex Pharmaceuticals Incorporated | Amides useful as inhibitors of voltage-gated sodium channels |
US8779197B2 (en) | 2007-10-11 | 2014-07-15 | Vertex Pharmaceuticals Incorporated | Aryl amides useful as inhibitors of voltage-gated sodium channels |
WO2011026240A1 (en) | 2009-09-04 | 2011-03-10 | Zalicus Pharmaceuticals Ltd. | Oxopiperazine derivatives for the treatment of pain and epilepsy |
PE20140868A1 (es) | 2011-06-24 | 2014-07-18 | Amgen Inc | Antagonistas trpm8 y su uso en tratamientos |
WO2012177896A1 (en) | 2011-06-24 | 2012-12-27 | Amgen Inc. | Trpm8 antagonists and their use in treatments |
MX368833B (es) | 2013-01-31 | 2019-10-18 | Vertex Pharma | Derivados de quinolina y quinazolina amidas como inhibidores de canales de sodio nav1.8 y el uso de los mismos en el tratamiento del dolor. |
KR102226588B1 (ko) | 2013-01-31 | 2021-03-11 | 버텍스 파마슈티칼스 인코포레이티드 | 나트륨 채널의 조절제로서의 아미드 |
SG11201505953TA (en) | 2013-01-31 | 2015-08-28 | Vertex Pharma | Pyridone amides as modulators of sodium channels |
WO2014146111A2 (en) * | 2013-03-15 | 2014-09-18 | The Regents Of The University Of California | Analgesic compounds and methods of use |
WO2015010065A1 (en) | 2013-07-19 | 2015-01-22 | Vertex Pharmaceuticals Incorporated | Sulfonamides as modulators of sodium channels |
DK3080134T3 (en) | 2013-12-13 | 2018-10-22 | Vertex Pharma | PRODRUGS OF PYRIDONAMIDS USED AS MODULATORS OF SODIUM CHANNELS |
KR101844984B1 (ko) | 2016-05-31 | 2018-04-03 | 한림대학교 산학협력단 | 5원 헤테로사이클릭 유도체, 이의 제조방법 및 이를 포함하는 약제학적 조성물 |
KR20200006128A (ko) | 2017-05-16 | 2020-01-17 | 버텍스 파마슈티칼스 인코포레이티드 | 나트륨 채널의 조절제로서의 중수소화 피리돈 아미드 및 이의 프로드럭 |
JOP20200001A1 (ar) | 2017-07-11 | 2022-10-30 | Vertex Pharma | كاربوكسأميدات بوصفها معدلات لقنوات الصوديوم |
CR20200116A (es) * | 2017-09-13 | 2021-04-28 | Amgen Inc | Compuestos de bisamida que activan el sarcómero y sus usos |
BR112021008524A8 (pt) | 2018-11-02 | 2023-02-07 | Merck Sharp & Dohme | 2-amino-n-heteroaril-nicotinamidas como inibidores de nav 1.8 |
-
2021
- 2021-06-15 EP EP21739498.0A patent/EP4168393A1/en active Pending
- 2021-06-15 CN CN202180057478.6A patent/CN116134018A/zh active Pending
- 2021-06-15 AR ARP210101629A patent/AR122628A1/es unknown
- 2021-06-15 PE PE2022002927A patent/PE20231383A1/es unknown
- 2021-06-15 CA CA3182633A patent/CA3182633A1/en active Pending
- 2021-06-15 WO PCT/US2021/037303 patent/WO2021257490A1/en active Application Filing
- 2021-06-15 JP JP2022577338A patent/JP7323723B2/ja active Active
- 2021-06-15 KR KR1020237001361A patent/KR20230024985A/ko active Search and Examination
- 2021-06-15 BR BR112022025805A patent/BR112022025805A2/pt unknown
- 2021-06-15 MX MX2022015581A patent/MX2022015581A/es unknown
- 2021-06-15 IL IL299180A patent/IL299180A/en unknown
- 2021-06-15 TW TW110121743A patent/TWI806073B/zh active
- 2021-06-15 CR CR20220642A patent/CR20220642A/es unknown
- 2021-06-15 AU AU2021293176A patent/AU2021293176A1/en active Pending
- 2021-06-15 US US17/347,639 patent/US11802122B2/en active Active
-
2022
- 2022-12-13 CL CL2022003544A patent/CL2022003544A1/es unknown
- 2022-12-15 CO CONC2022/0018295A patent/CO2022018295A2/es unknown
- 2022-12-15 DO DO2022000290A patent/DOP2022000290A/es unknown
-
2023
- 2023-01-16 EC ECSENADI20233443A patent/ECSP23003443A/es unknown
- 2023-04-19 JP JP2023068778A patent/JP2023093623A/ja active Pending
- 2023-06-05 US US18/329,108 patent/US20230312528A1/en active Pending
- 2023-07-27 JP JP2023122332A patent/JP2023139235A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
KR20230024985A (ko) | 2023-02-21 |
PE20231383A1 (es) | 2023-09-12 |
CA3182633A1 (en) | 2021-12-23 |
DOP2022000290A (es) | 2023-01-31 |
CR20220642A (es) | 2023-02-15 |
TW202214573A (zh) | 2022-04-16 |
US11802122B2 (en) | 2023-10-31 |
ECSP23003443A (es) | 2023-02-28 |
US20230312528A1 (en) | 2023-10-05 |
TWI806073B (zh) | 2023-06-21 |
AR122628A1 (es) | 2022-09-21 |
BR112022025805A2 (pt) | 2023-01-10 |
WO2021257490A1 (en) | 2021-12-23 |
JP2023139235A (ja) | 2023-10-03 |
EP4168393A1 (en) | 2023-04-26 |
CN116134018A (zh) | 2023-05-16 |
MX2022015581A (es) | 2023-01-24 |
IL299180A (en) | 2023-02-01 |
JP2023093623A (ja) | 2023-07-04 |
JP7323723B2 (ja) | 2023-08-08 |
CL2022003544A1 (es) | 2023-06-02 |
US20210403457A1 (en) | 2021-12-30 |
JP2023524167A (ja) | 2023-06-08 |
AU2021293176A1 (en) | 2023-02-02 |
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