CN116783191A - 作为prmt5抑制剂的三环甲酰胺衍生物 - Google Patents
作为prmt5抑制剂的三环甲酰胺衍生物 Download PDFInfo
- Publication number
- CN116783191A CN116783191A CN202180091440.0A CN202180091440A CN116783191A CN 116783191 A CN116783191 A CN 116783191A CN 202180091440 A CN202180091440 A CN 202180091440A CN 116783191 A CN116783191 A CN 116783191A
- Authority
- CN
- China
- Prior art keywords
- methyl
- amino
- carboxamide
- quinoline
- dihydrofuro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Classifications
-
- 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
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- 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
-
- 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
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
-
- 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
- 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
- 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
- C07D471/12—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 three hetero rings
- C07D471/14—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
-
- 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
- C07D491/14—Ortho-condensed systems
- C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- 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)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US202063117937P | 2020-11-24 | 2020-11-24 | |
| US63/117937 | 2020-11-24 | ||
| PCT/US2021/060332 WO2022115377A1 (en) | 2020-11-24 | 2021-11-22 | Tricyclic carboxamide derivatives as prmt5 inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116783191A true CN116783191A (zh) | 2023-09-19 |
Family
ID=78957958
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202180091440.0A Pending CN116783191A (zh) | 2020-11-24 | 2021-11-22 | 作为prmt5抑制剂的三环甲酰胺衍生物 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US20240101570A1 (https=) |
| EP (1) | EP4251624B1 (https=) |
| JP (1) | JP2023550466A (https=) |
| KR (1) | KR20230113339A (https=) |
| CN (1) | CN116783191A (https=) |
| AU (1) | AU2021386149A1 (https=) |
| CA (1) | CA3202141A1 (https=) |
| CL (1) | CL2023001461A1 (https=) |
| CO (1) | CO2023007504A2 (https=) |
| CR (1) | CR20230286A (https=) |
| ES (1) | ES3058979T3 (https=) |
| IL (1) | IL302820B1 (https=) |
| JO (1) | JOP20230113A1 (https=) |
| MX (1) | MX2023006145A (https=) |
| PE (1) | PE20231312A1 (https=) |
| SA (1) | SA523440916B1 (https=) |
| WO (1) | WO2022115377A1 (https=) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116462676A (zh) * | 2022-01-20 | 2023-07-21 | 上海和誉生物医药科技有限公司 | 一种多稠环prmt5抑制剂及其制备方法和应用 |
| CN119552151A (zh) * | 2025-01-24 | 2025-03-04 | 赛岚(杭州)生物医药科技有限公司 | 新型prmt5抑制剂及其用途 |
| WO2025113705A1 (zh) * | 2023-12-01 | 2025-06-05 | 上海翰森生物医药科技有限公司 | N-取代酰胺类衍生物抑制剂、其制备方法和应用 |
| WO2025180517A1 (zh) * | 2024-03-01 | 2025-09-04 | 武汉人福创新药物研发中心有限公司 | 含sf5类喹啉衍生物及其作为p2x7拮抗剂的用途 |
| WO2025218671A1 (en) * | 2024-04-16 | 2025-10-23 | Shanghai Apeiron Therapeutics Company Limited | Novel prmt5 proteolysis targeting chimeric molecules and associated methods of use |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11077101B1 (en) | 2018-07-18 | 2021-08-03 | Tango Therapeutics, Inc. | Compounds and methods of use |
| US12403137B2 (en) | 2019-10-28 | 2025-09-02 | Tango Therapeutics, Inc. | Compounds and methods of use |
| WO2022026892A1 (en) | 2020-07-31 | 2022-02-03 | Tango Therapeutics, Inc. | Piperidin-1- yl-n-pyrydi ne-3-yl-2-oxoacet am ide derivatives useful for the treatment of mtap-deficient and/or mt a-accumulating cancers |
| CN116462677A (zh) * | 2022-01-20 | 2023-07-21 | 上海和誉生物医药科技有限公司 | 一种多稠环prmt5抑制剂及其制备方法和应用 |
| US12552760B2 (en) * | 2022-04-22 | 2026-02-17 | The Board Of Trustees Of The University Of Illinois | Compounds for increasing the nicotinamide adenine dinucleotide in a subject and methods of use thereof |
| WO2023246873A1 (zh) * | 2022-06-23 | 2023-12-28 | 南京明德新药研发有限公司 | 氨基取代的杂芳基衍生物及其应用 |
| EP4549440A4 (en) * | 2022-07-01 | 2026-04-22 | Cytosinlab Therapeutics Co Ltd | CLASS OF PRMT5 INHIBITORS AND THEIR USES |
| CN117362304A (zh) * | 2022-07-07 | 2024-01-09 | 深圳微芯生物科技股份有限公司 | 一种甲酰胺取代的杂三环类衍生物、其制备方法及其应用 |
| KR20250004026A (ko) * | 2022-07-15 | 2025-01-07 | 아비스코 테라퓨틱스 컴퍼니 리미티드 | Prmt5 억제제, 그 제조 방법과 약학에서의 응용 |
| KR20250002472A (ko) * | 2022-08-03 | 2025-01-07 | 아비스코 테라퓨틱스 컴퍼니 리미티드 | 질소 함유 삼중 축합고리 prmt5 억제제 및 이의 제조 방법 및 약학적 용도 |
| WO2024032572A1 (zh) * | 2022-08-09 | 2024-02-15 | 上海湃隆生物科技有限公司 | 新型prmt5抑制剂及其应用 |
| AU2023327684A1 (en) | 2022-08-15 | 2025-03-20 | Astrazeneca Ab | Mta-cooperative prmt5 inhibitors for use in the treatment of cancer |
| CN118613482B (zh) * | 2022-09-26 | 2025-09-30 | 上海湃隆生物科技有限公司 | 新型prmt5抑制剂及其应用 |
| AU2023409398A1 (en) * | 2022-12-22 | 2025-06-05 | Gilead Sciences, Inc. | Prmt5 inhibitors and uses thereof |
| CN120418246A (zh) * | 2022-12-23 | 2025-08-01 | 成都微芯药业有限公司 | 一类含炔基取代的杂环酰胺衍生物、其制备方法及其应用 |
| CN118103373A (zh) * | 2023-01-18 | 2024-05-28 | 上海德琪医药科技有限公司 | Prmt5抑制化合物和其用途 |
| WO2024170488A1 (en) | 2023-02-13 | 2024-08-22 | Astrazeneca Ab | Prmt5 inhibitor for use in cancer therapy |
| TW202438054A (zh) * | 2023-03-30 | 2024-10-01 | 瑞士商百濟神州瑞士有限責任公司 | 作為ＭＴＡ－協同ＰＲＭＴ５抑制劑的５－胺基－６，８－二氫－１Ｈ－呋喃并［３，４－ｄ］吡咯并［３，２－ｂ］吡啶－２－甲醯胺衍生物 |
| CR20250446A (es) * | 2023-04-21 | 2025-12-02 | Gilead Sciences Inc | Inhibidores de prmt5 y usos de los mismos |
| WO2024234821A1 (zh) * | 2023-05-17 | 2024-11-21 | 四川科伦博泰生物医药股份有限公司 | 三并环酰胺化合物、包含其的药物组合物及其制备方法和用途 |
| AU2024275020A1 (en) * | 2023-05-24 | 2025-11-13 | Ryvu Therapeutics S.A. | Prmt5 inhibitors |
| TW202513565A (zh) * | 2023-06-02 | 2025-04-01 | 香港商英矽智能科技知識產權有限公司 | Prmt5抑制劑及其用途 |
| WO2025016323A1 (zh) | 2023-07-14 | 2025-01-23 | 江苏亚虹医药科技股份有限公司 | 蛋白质精氨酸酶甲基转移酶-5抑制剂及其医药用途 |
| WO2025026381A1 (zh) * | 2023-08-02 | 2025-02-06 | 成都微芯药业有限公司 | 杂环炔基取代的酰胺衍生物、其制备方法及其应用 |
| TW202521525A (zh) | 2023-08-09 | 2025-06-01 | 大陸商江蘇恆瑞醫藥股份有限公司 | 雜芳基化合物、其製備方法及其在醫藥上的應用 |
| WO2025039979A1 (zh) | 2023-08-18 | 2025-02-27 | 江苏亚虹医药科技股份有限公司 | 蛋白质精氨酸酶甲基转移酶-5抑制剂及其医药用途 |
| US11858935B1 (en) | 2023-09-06 | 2024-01-02 | King Faisal University | Pyrrolo[2,3-c][1,7]naphthyridine-2-carboxylic acid compounds as CK2 inhibitors |
| US11891394B1 (en) | 2023-09-06 | 2024-02-06 | King Faisal University | Pyrrolo[2,3-c][1,6]naphthyridine-8-carboxylic acid compounds as CK2 inhibitors |
| WO2025137640A1 (en) | 2023-12-22 | 2025-06-26 | Gilead Sciences, Inc. | Azaspiro wrn inhibitors |
| WO2025166260A1 (en) * | 2024-02-02 | 2025-08-07 | Ideaya Biosciences, Inc. | Amide substituted tricyclic guanidino compounds as prmt5 inhibitors |
| WO2025166257A1 (en) * | 2024-02-02 | 2025-08-07 | Ideaya Biosciences, Inc. | Amide substituted triheterocyclic guanidino compounds as prmt5 inhibitors |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017153515A1 (en) * | 2016-03-09 | 2017-09-14 | Ctxt Pty Limited | Tetrahydroisoquinolines as prmt5-inhibitors |
| WO2019209896A1 (en) * | 2018-04-25 | 2019-10-31 | Innate Tumor Immunity, Inc. | Nlrp3 modulators |
| JP2020504716A (ja) * | 2016-12-22 | 2020-02-13 | グローバル ブラッド セラピューティクス インコーポレイテッド | ヒストンメチルトランスフェラーゼ阻害剤 |
| CN111542523A (zh) * | 2017-11-24 | 2020-08-14 | 朱比连特埃皮斯科瑞有限责任公司 | 作为prmt5抑制剂的杂环化合物 |
-
2021
- 2021-11-22 WO PCT/US2021/060332 patent/WO2022115377A1/en not_active Ceased
- 2021-11-22 AU AU2021386149A patent/AU2021386149A1/en active Pending
- 2021-11-22 KR KR1020237021023A patent/KR20230113339A/ko active Pending
- 2021-11-22 US US18/255,575 patent/US20240101570A1/en active Pending
- 2021-11-22 EP EP21827727.5A patent/EP4251624B1/en active Active
- 2021-11-22 CR CR20230286A patent/CR20230286A/es unknown
- 2021-11-22 JP JP2023530598A patent/JP2023550466A/ja active Pending
- 2021-11-22 ES ES21827727T patent/ES3058979T3/es active Active
- 2021-11-22 CA CA3202141A patent/CA3202141A1/en active Pending
- 2021-11-22 CN CN202180091440.0A patent/CN116783191A/zh active Pending
- 2021-11-22 PE PE2023001721A patent/PE20231312A1/es unknown
- 2021-11-22 MX MX2023006145A patent/MX2023006145A/es unknown
-
2023
- 2023-05-10 IL IL302820A patent/IL302820B1/en unknown
- 2023-05-22 CL CL2023001461A patent/CL2023001461A1/es unknown
- 2023-05-23 JO JOJO/P/2023/0113A patent/JOP20230113A1/ar unknown
- 2023-05-24 SA SA523440916A patent/SA523440916B1/ar unknown
- 2023-06-06 CO CONC2023/0007504A patent/CO2023007504A2/es unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017153515A1 (en) * | 2016-03-09 | 2017-09-14 | Ctxt Pty Limited | Tetrahydroisoquinolines as prmt5-inhibitors |
| JP2020504716A (ja) * | 2016-12-22 | 2020-02-13 | グローバル ブラッド セラピューティクス インコーポレイテッド | ヒストンメチルトランスフェラーゼ阻害剤 |
| CN111542523A (zh) * | 2017-11-24 | 2020-08-14 | 朱比连特埃皮斯科瑞有限责任公司 | 作为prmt5抑制剂的杂环化合物 |
| WO2019209896A1 (en) * | 2018-04-25 | 2019-10-31 | Innate Tumor Immunity, Inc. | Nlrp3 modulators |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116462676A (zh) * | 2022-01-20 | 2023-07-21 | 上海和誉生物医药科技有限公司 | 一种多稠环prmt5抑制剂及其制备方法和应用 |
| WO2025113705A1 (zh) * | 2023-12-01 | 2025-06-05 | 上海翰森生物医药科技有限公司 | N-取代酰胺类衍生物抑制剂、其制备方法和应用 |
| WO2025180517A1 (zh) * | 2024-03-01 | 2025-09-04 | 武汉人福创新药物研发中心有限公司 | 含sf5类喹啉衍生物及其作为p2x7拮抗剂的用途 |
| WO2025218671A1 (en) * | 2024-04-16 | 2025-10-23 | Shanghai Apeiron Therapeutics Company Limited | Novel prmt5 proteolysis targeting chimeric molecules and associated methods of use |
| CN119552151A (zh) * | 2025-01-24 | 2025-03-04 | 赛岚(杭州)生物医药科技有限公司 | 新型prmt5抑制剂及其用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20230113339A (ko) | 2023-07-28 |
| EP4251624B1 (en) | 2025-10-29 |
| IL302820B1 (en) | 2026-03-01 |
| MX2023006145A (es) | 2023-06-06 |
| AU2021386149A9 (en) | 2024-08-08 |
| US20240101570A1 (en) | 2024-03-28 |
| JP2023550466A (ja) | 2023-12-01 |
| IL302820A (en) | 2023-07-01 |
| CR20230286A (es) | 2023-08-24 |
| PE20231312A1 (es) | 2023-08-24 |
| JOP20230113A1 (ar) | 2023-05-23 |
| CA3202141A1 (en) | 2022-06-02 |
| WO2022115377A1 (en) | 2022-06-02 |
| EP4251624A1 (en) | 2023-10-04 |
| CO2023007504A2 (es) | 2023-09-08 |
| CL2023001461A1 (es) | 2023-12-01 |
| ES3058979T3 (en) | 2026-03-16 |
| AU2021386149A1 (en) | 2023-06-22 |
| SA523440916B1 (ar) | 2025-05-07 |
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