HRP20241184T1 - Moćni i selektivni spojevi kao modulatori serotonin 1b receptora - Google Patents
Moćni i selektivni spojevi kao modulatori serotonin 1b receptora Download PDFInfo
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- HRP20241184T1 HRP20241184T1 HRP20241184TT HRP20241184T HRP20241184T1 HR P20241184 T1 HRP20241184 T1 HR P20241184T1 HR P20241184T T HRP20241184T T HR P20241184TT HR P20241184 T HRP20241184 T HR P20241184T HR P20241184 T1 HRP20241184 T1 HR P20241184T1
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- Croatia
- Prior art keywords
- methyl
- oxadiazol
- dimethylamino
- ethoxy
- phenyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims 17
- 102100027499 5-hydroxytryptamine receptor 1B Human genes 0.000 title claims 3
- 101710138639 5-hydroxytryptamine receptor 1B Proteins 0.000 title claims 3
- 230000003389 potentiating effect Effects 0.000 title 1
- -1 nicotinamide N-(4-bromo-3-(2-(dimethylamino)ethoxy)phenyl)-6-(2-methoxy-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)nicotinamide Chemical compound 0.000 claims 7
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 239000013066 combination product Substances 0.000 claims 3
- 229940127555 combination product Drugs 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 2
- 230000008485 antagonism Effects 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
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- 230000001575 pathological effect Effects 0.000 claims 2
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
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- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 1
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- DTVDYOBOXNJMPK-UHFFFAOYSA-N CC1=NC(C(C=C2)=CC(F)=C2C(C=C2)=CC=C2C(NC(C=C2OCCN(C)C)=NC=C2Br)=O)=NO1 Chemical compound CC1=NC(C(C=C2)=CC(F)=C2C(C=C2)=CC=C2C(NC(C=C2OCCN(C)C)=NC=C2Br)=O)=NO1 DTVDYOBOXNJMPK-UHFFFAOYSA-N 0.000 claims 1
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- SASAFFCTHHUDNM-UHFFFAOYSA-N CC1=NC(C(C=C2)=CC(F)=C2C(C=C2)=NC=C2C(NC(C=C2OCCN(C)C)=NC=C2C#N)=O)=NO1 Chemical compound CC1=NC(C(C=C2)=CC(F)=C2C(C=C2)=NC=C2C(NC(C=C2OCCN(C)C)=NC=C2C#N)=O)=NO1 SASAFFCTHHUDNM-UHFFFAOYSA-N 0.000 claims 1
- RQNIIWCZOYPGIJ-UHFFFAOYSA-N CC1=NC(C(C=C2)=CC(OC)=C2C(C=C2)=CC=C2C(NC(C=C2OCCN(C)C)=NC=C2Br)=O)=NO1 Chemical compound CC1=NC(C(C=C2)=CC(OC)=C2C(C=C2)=CC=C2C(NC(C=C2OCCN(C)C)=NC=C2Br)=O)=NO1 RQNIIWCZOYPGIJ-UHFFFAOYSA-N 0.000 claims 1
- QVLKWTBCGMUHIH-UHFFFAOYSA-N CC1=NC(C(C=C2)=CC(OC)=C2C(C=C2)=CC=C2C(NC(C=C2OCCN(C)C)=NC=C2C#N)=O)=NO1 Chemical compound CC1=NC(C(C=C2)=CC(OC)=C2C(C=C2)=CC=C2C(NC(C=C2OCCN(C)C)=NC=C2C#N)=O)=NO1 QVLKWTBCGMUHIH-UHFFFAOYSA-N 0.000 claims 1
- LHVHHPJEZOLECI-UHFFFAOYSA-N CC1=NC(C(C=C2)=CC(OC)=C2C(C=C2)=NC=C2C(NC(C=C2OCCN(C)C)=NC=C2Br)=O)=NO1 Chemical compound CC1=NC(C(C=C2)=CC(OC)=C2C(C=C2)=NC=C2C(NC(C=C2OCCN(C)C)=NC=C2Br)=O)=NO1 LHVHHPJEZOLECI-UHFFFAOYSA-N 0.000 claims 1
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- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims 1
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims 1
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims 1
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 229940044683 chemotherapy drug Drugs 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229960004397 cyclophosphamide Drugs 0.000 claims 1
- 229960000684 cytarabine Drugs 0.000 claims 1
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 claims 1
- 229960000975 daunorubicin Drugs 0.000 claims 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims 1
- 229960003957 dexamethasone Drugs 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229950009791 durvalumab Drugs 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 201000005787 hematologic cancer Diseases 0.000 claims 1
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 239000002955 immunomodulating agent Substances 0.000 claims 1
- 229960005386 ipilimumab Drugs 0.000 claims 1
- 208000019423 liver disease Diseases 0.000 claims 1
- 229960001428 mercaptopurine Drugs 0.000 claims 1
- 229960000485 methotrexate Drugs 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- IXOXBSCIXZEQEQ-UHTZMRCNSA-N nelarabine Chemical compound C1=NC=2C(OC)=NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O IXOXBSCIXZEQEQ-UHTZMRCNSA-N 0.000 claims 1
- 229960000801 nelarabine Drugs 0.000 claims 1
- 229960003966 nicotinamide Drugs 0.000 claims 1
- 235000005152 nicotinamide Nutrition 0.000 claims 1
- 239000011570 nicotinamide Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 229960003301 nivolumab Drugs 0.000 claims 1
- 229960002621 pembrolizumab Drugs 0.000 claims 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 claims 1
- 229960004618 prednisone Drugs 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 229950007217 tremelimumab Drugs 0.000 claims 1
- 229960004528 vincristine Drugs 0.000 claims 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 claims 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- 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
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
-
- 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
- C07D413/10—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 carbon chain containing aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
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- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP20382888 | 2020-10-08 | ||
| PCT/EP2021/077660 WO2022074103A1 (en) | 2020-10-08 | 2021-10-07 | Potent and selctive compounds as serotonin 1b receptor modulators |
| EP21789678.6A EP4225753B1 (en) | 2020-10-08 | 2021-10-07 | Potent and selective compounds as serotonin 1b receptor modulators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20241184T1 true HRP20241184T1 (hr) | 2024-11-22 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20241184TT HRP20241184T1 (hr) | 2020-10-08 | 2021-10-07 | Moćni i selektivni spojevi kao modulatori serotonin 1b receptora |
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| EP (2) | EP4225753B1 (enExample) |
| JP (1) | JP7687636B2 (enExample) |
| KR (1) | KR20230107566A (enExample) |
| CN (1) | CN116635390B (enExample) |
| AU (1) | AU2021356114A1 (enExample) |
| CA (1) | CA3194700A1 (enExample) |
| CL (1) | CL2023001021A1 (enExample) |
| DK (1) | DK4225753T3 (enExample) |
| ES (1) | ES2985416T3 (enExample) |
| FI (1) | FI4225753T3 (enExample) |
| HR (1) | HRP20241184T1 (enExample) |
| HU (1) | HUE068199T2 (enExample) |
| IL (1) | IL301806B2 (enExample) |
| LT (1) | LT4225753T (enExample) |
| MX (1) | MX2023004116A (enExample) |
| PL (1) | PL4225753T3 (enExample) |
| PT (1) | PT4225753T (enExample) |
| RS (1) | RS65956B1 (enExample) |
| SI (1) | SI4225753T1 (enExample) |
| WO (1) | WO2022074103A1 (enExample) |
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| KR102993831B1 (ko) | 2020-10-08 | 2026-07-23 | 머크 샤프 앤드 돔 엘엘씨 | 신규 디아실글리세리드 o-아실트랜스퍼라제 2 억제제로서의 옥스인돌 유도체의 제조 |
| CN117903116A (zh) * | 2021-08-27 | 2024-04-19 | 杭州阿诺生物医药科技有限公司 | 细胞周期蛋白k降解剂 |
| JP2026521568A (ja) | 2023-06-16 | 2026-06-30 | レウコス バイオテク ソシエダッド リミターダ | ５－ｈｔｒ１ｂ調節因子を用いた固形腫瘍の治療 |
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| TW240217B (enExample) | 1992-12-30 | 1995-02-11 | Glaxo Group Ltd | |
| US5801170A (en) | 1993-12-07 | 1998-09-01 | Smithkline Beecham Plc | Heterocyclic biphenylylamides useful as 5HT1D antagonists |
| ZA985542B (en) | 1997-07-03 | 1999-04-07 | Smithkline Beecham Corp | Substituted benzanilides as CCR5 receptor ligands antiinflammatory agents and antiviral agents |
| SK492001A3 (en) | 1998-07-20 | 2001-08-06 | Merck Patent Gmbh | Biphenyl derivatives |
| HUP0302966A2 (hu) | 2000-07-31 | 2003-12-29 | Smithkline Beecham P.L.C. | Karboxamid-vegyületek és alkalmazásuk humán 11CBY receptor antagonistákként, eljárás az előállításukra és ezeket tartalmazó gyógyszerkészítmények |
| US7105682B2 (en) | 2001-01-12 | 2006-09-12 | Amgen Inc. | Substituted amine derivatives and methods of use |
| WO2007057742A2 (en) | 2005-11-18 | 2007-05-24 | Pfizer Products Inc. | Novel piperazinone derivatives |
| WO2007077457A2 (en) | 2006-01-06 | 2007-07-12 | The Royal Veterinary College | Treatment of equine laminitis with 5-ht1b/ 1d antagonists |
| EP3348266A1 (en) | 2017-01-16 | 2018-07-18 | Leukos Biotech, S.L. | Combination therapy for treating cancer |
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2021
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- 2021-10-07 MX MX2023004116A patent/MX2023004116A/es unknown
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- 2021-10-07 HR HRP20241184TT patent/HRP20241184T1/hr unknown
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2023
- 2023-04-06 CL CL2023001021A patent/CL2023001021A1/es unknown
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2026
- 2026-01-15 US US19/450,120 patent/US20260138974A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US20260138974A1 (en) | 2026-05-21 |
| US20240166639A1 (en) | 2024-05-23 |
| WO2022074103A1 (en) | 2022-04-14 |
| KR20230107566A (ko) | 2023-07-17 |
| CL2023001021A1 (es) | 2023-11-24 |
| FI4225753T3 (fi) | 2024-08-29 |
| DK4225753T3 (da) | 2024-08-19 |
| CN116635390A (zh) | 2023-08-22 |
| CN116635390B (zh) | 2026-03-27 |
| ES2985416T3 (es) | 2024-11-05 |
| CA3194700A1 (en) | 2022-04-14 |
| JP7687636B2 (ja) | 2025-06-03 |
| LT4225753T (lt) | 2024-08-26 |
| IL301806B1 (en) | 2026-01-01 |
| US12540133B2 (en) | 2026-02-03 |
| EP4445901A3 (en) | 2024-12-04 |
| PT4225753T (pt) | 2024-08-30 |
| EP4445901A2 (en) | 2024-10-16 |
| SI4225753T1 (sl) | 2024-10-30 |
| EP4225753A1 (en) | 2023-08-16 |
| IL301806A (en) | 2023-05-01 |
| AU2021356114A9 (en) | 2024-09-12 |
| IL301806B2 (en) | 2026-05-01 |
| PL4225753T3 (pl) | 2024-11-18 |
| EP4225753B1 (en) | 2024-07-31 |
| JP2023547346A (ja) | 2023-11-10 |
| HUE068199T2 (hu) | 2024-12-28 |
| AU2021356114A1 (en) | 2023-05-18 |
| RS65956B1 (sr) | 2024-10-31 |
| MX2023004116A (es) | 2023-06-13 |
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