HRP20231618T1 - Postupak za pripremu ivosideniba i njegovog intermedijara - Google Patents
Postupak za pripremu ivosideniba i njegovog intermedijara Download PDFInfo
- Publication number
- HRP20231618T1 HRP20231618T1 HRP20231618TT HRP20231618T HRP20231618T1 HR P20231618 T1 HRP20231618 T1 HR P20231618T1 HR P20231618T T HRP20231618T T HR P20231618TT HR P20231618 T HRP20231618 T HR P20231618T HR P20231618 T1 HRP20231618 T1 HR P20231618T1
- Authority
- HR
- Croatia
- Prior art keywords
- compound iia
- ethanol solvate
- crystalline
- crystalline ethanol
- solvate
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 16
- WIJZXSAJMHAVGX-DHLKQENFSA-N ivosidenib Chemical compound FC1=CN=CC(N([C@H](C(=O)NC2CC(F)(F)C2)C=2C(=CC=CC=2)Cl)C(=O)[C@H]2N(C(=O)CC2)C=2N=CC=C(C=2)C#N)=C1 WIJZXSAJMHAVGX-DHLKQENFSA-N 0.000 title 1
- 229950010738 ivosidenib Drugs 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 56
- 150000001875 compounds Chemical class 0.000 claims 36
- 239000012453 solvate Substances 0.000 claims 31
- 238000000634 powder X-ray diffraction Methods 0.000 claims 16
- 239000000203 mixture Substances 0.000 claims 8
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 6
- 238000006243 chemical reaction Methods 0.000 claims 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims 6
- 239000000126 substance Substances 0.000 claims 6
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 claims 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 2
- FVKFHMNJTHKMRX-UHFFFAOYSA-N 3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine Chemical compound C1CCN2CCCNC2=N1 FVKFHMNJTHKMRX-UHFFFAOYSA-N 0.000 claims 2
- 238000002425 crystallisation Methods 0.000 claims 2
- 230000008025 crystallization Effects 0.000 claims 2
- 229940043279 diisopropylamine Drugs 0.000 claims 2
- 238000002955 isolation Methods 0.000 claims 2
- 239000012454 non-polar solvent Substances 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- KNGUWKBLWSRYCV-UHFFFAOYSA-N 1,1-difluoro-3-isocyanatocyclobutane Chemical compound FC1(F)CC(N=C=O)C1 KNGUWKBLWSRYCV-UHFFFAOYSA-N 0.000 claims 1
- AWSJFEKOXQBDSL-UHFFFAOYSA-N 2-bromopyridine-4-carbonitrile Chemical compound BrC1=CC(C#N)=CC=N1 AWSJFEKOXQBDSL-UHFFFAOYSA-N 0.000 claims 1
- FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 claims 1
- ZRORIJXOWXYPMO-UHFFFAOYSA-N 5-fluoropyridin-3-amine Chemical compound NC1=CN=CC(F)=C1 ZRORIJXOWXYPMO-UHFFFAOYSA-N 0.000 claims 1
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- SBNQZJXLQLUESH-UHFFFAOYSA-N ethyl 2-bromopyridine-4-carboxylate Chemical compound CCOC(=O)C1=CC=NC(Br)=C1 SBNQZJXLQLUESH-UHFFFAOYSA-N 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
Classifications
-
- 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
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
Claims (18)
1. Postupak za pripremu spoja I
[image]
koji sadrži izoliranje kristalnog etanolnog solvata spoja IIa
[image]
i pretvaranje etanolnog solvata spoja IIa u spoj I ili njegov solvat.
2. Postupak prema patentnom zahtjevu 1, naznačen time što izoliranje kristalnog etanolnog solvata spoja IIa sadrži kristalizaciju spoja IIa iz mješavine spojeva formule II
[image]
3. Postupak prema patentnom zahtjevu 1, naznačen time što pretvaranje kristalnog etanolnog solvata spoja IIa sadrži reakciju spoja IIa sa 2-halo-4-cijanopiridinom da bi se dobio spoj I.
4. Postupak prema patentnom zahtjevu 2, naznačen time što kristalizacija kristalnog etanolnog solvata spoja IIa sadrži suspendiranje ili rastvaranje dijastereomerne mješavine spojeva formule II u sustavu otapala etanola, dodavanje baze i miješanje mješavine na između 0 i 25°C, i dodavanje najmanje jednog nepolarnog otapala.
5. Postupak prema patentnom zahtjevu 4, naznačen time što je baza izabrana iz grupa koje se sastoje od 1,5,7-triazabiciklo[4.4.0]dek-5-ena („TBD“), 1,5-diazabiciklo[4.3.0]non-5-ena („DBN“), trietilamina, diizopropil amina, N,N-diizopropil etilamina, N-metilmorfolina, morfolina, N-metil-piperazina, piridina, butilamina, dibutilamina i 1,5-diazabiciklo(4.3.0)non-5-ena ili njihove mješavine.
6. Postupak prema patentnom zahtjevu 2 naznačen time što je mješavina spojeva Formule II pripremljena reakcijom 2-klorobenzaldehida sa 5-fluoropiridin-3-aminom u metanolu, nakon čega slijedi reagiranje nastalog proizvoda sa (S)-5-oksopirolidin-2-karboksilnom kiselinom i 1,1-difluoro-3-izocijanatociklobutanom da bi se dobila mješavina spojeva formule II.
7. Postupak prema patentnom zahtjevu 1 koji sadrži reakciju kristalnog etanolnog solvata spoja IIa sa 2-bromoizonikotinonitrilom da bi se dobio spoj I.
8. Postupak prema patentnom zahtjevu 1, koji sadrži reakciju kristalnog etanolnog solvata spoja IIa sa etil 2-bromoizonikotinatom da bi se dobio intermedijar S9:
[image]
9. Postupak prema patentnom zahtjevu 8, koji sadrži redukciju intermedijara S9 u prisustvu NH3 da bi se dobio amid S10:
[image]
10. Postupak prema patentnom zahtjevu 9, koji sadrži miješanje S10 sa trifluorooctenim anhidridom (TFAA) u prisustvu piridina da bi se dobio spoj I.
11. Postupak prema bilo kojem od patentnih zahtjeva 1 ili 2, pri čemu:
(a) kristalni etanolni solvat spoja IIa je naznačen obrascem rendgenske difrakcije praha (XRPD) koji sadrži jedan ili više od sljedećih pikova na 2θ: 7.2° ± 0.2 °, 8.6° ± 0.2 °, 12.2° ± 0.2 °, 13.1° ± 0.2 °, 14.4 ° ± 0.2°, 16.7° ± 0.2°, 19.4° ± 0.2 °, 19.8° ± 0.2°, 21.8° ± 0.2 ° i 25.2° ± 0.2 °; ili
(b) kristalni etanolni solvat spoja IIa je naznačen obrascem rendgenske difrakcije praha (XRPD) koji sadrži tri ili više od sljedećih pikova na 2Θ: 7.2° ± 0.2 °, 8.6° ± 0.2 °, 12.2° ± 0.2 °, 13.1° ± 0.2 °, 14.4 ° ± 0.2°, 16.7° ± 0.2°, 19.4° ± 0.2 °, 19.8° ± 0.2°, 21.8° ± 0.2 ° i 25.2° ± 0.2 °.
12. Postupak prema bilo kom od patentnih zahtjeva 1 ili 2, naznačen time što:
(a) kristalni etanolni solvat spoja IIa ima dijastereomernu čistoću od najmanje 90% i kemijsku čistoću od najmanje 80%; ili
(b) kristalni etanolni solvat spoja IIa ima dijastereomernu čistoću između 90% do 99%; ili
(c) kristalni etanolni solvat spoja IIa ima kemijsku čistoću između 80% do 99%.
13. Postupak za pripremu kristalnog etanolnog solvata spoja IIa:
[image]
koji sadrži suspendiranje ili rastvaranje mješavine spojeva formule II
[image]
i baze u sustavu otapala etanola, dodavanjem najmanje jednog nepolarnog otapala i izoliranjem kristalnog etanolnog solvata spoja IIa; izborno
pri čemu je baza izabrana iz grupe koja se sastoji od 1,5,7-triazabiciklo[4.4.0]dek-5-ena ("TBD"), 1,5-diazabiciklo[4.3.0]non-5-ena ("DBN"), trietilamina, diizopropil amina, N,N-diizopropil etilamina, N-metilmorfolina, morfolina, N-metil-piperazina, piridina, butilamina, dibutilamina i 1,5-diazabiciklo(4.3.0)non-5-ena ili njihove mješavine.
14. Postupak prema patentnom zahtjevu 13, naznačen time što:
(a) kristalni etanolni solvat spoja IIa ima dijastereomernu čistoću od najmanje 90% i kemijsku čistoću od najmanje 80%; i/ili
(b) kristalni etanolni solvat spoja IIa ima dijastereomernu čistoću između 90% do 99%.
15. Postupak prema bilo kojem od patentnih zahtjeva 13-14, pri čemu
(a) kristalni etanolni solvat spoja IIa je naznačen obrascem rendgenske difrakcije praha (XRPD) u kojem je prisutno najmanje 50% najintenzivnijih pikova prikazanih u tabeli ispod:
[image]
i/ili
(b) kristalni etanolni solvat spoja IIa je naznačen obrascem rendgenske difrakcije praha (XRPD) koji sadrži jedan ili više od sljedećih pikova na 2Θ: 7.2° ± 0.2 °, 8.6° ± 0.2 °, 12.2° ± 0.2 °, 13.1° ± 0.2 °, 14.4 ° ± 0.2°, 16.7° ± 0.2°, 19.4° ± 0.2 °, 19.8° ± 0.2°, 21.8° ± 0.2 ° i 25.2° ± 0.2 °; i/ili
(c) kristalni etanolni solvat spoja IIa je naznačen obrascem rendgenske difrakcije praha (XRPD) koji sadrži tri ili više od sljedećih pikova na 2Θ: 7.2° ± 0.2 °, 8.6° ± 0.2 °, 12.2° ± 0.2 °, 13.1° ± 0.2 °, 14.4 ° ± 0.2°, 16.7° ± 0.2°, 19.4° ± 0.2 °, 19.8° ± 0.2°, 21.8° ± 0.2 ° i 25.2° ± 0.2 °; i/ili
(d) pri čemu kristalni etanolni solvat spoja IIa ima kemijsku čistoću između 80% do 99%.
16. Kristalni etanolni solvat spoja IIa:
[image]
17. Kristalni etanolni solvat prema patentnom zahtjevu 16, pri čemu:
(a) kristalni etanolni solvat spoja IIa je naznačen obrascem rendgenske difrakcije praha (XRPD) u kojem je prisutno najmanje 50% najintenzivnijih pikova prikazanih u tabeli ispod:
[image]
ili
(b) kristalni etanolni solvat spoja IIa je naznačen obrascem rendgenske difrakcije praha (XRPD) koji sadrži jedan ili više od sljedećih pikova na 2Θ: 7.2° ± 0.2 °, 8.6° ± 0.2 °, 12.2° ± 0.2 °, 13.1° ± 0.2 °, 14.4 ° ± 0.2°, 16.7° ± 0.2°, 19.4° ± 0.2 °, 19.8° ± 0.2°, 21.8° ± 0.2 ° i 25.2° ± 0.2 °; ili
(c) kristalni etanolni solvat spoja IIa je naznačen obrascem rendgenske difrakcije praha (XRPD) koji sadrži tri ili više od sljedećih pikova na 2θ: 7.2° ± 0.2 °, 8.6° ± 0.2 °, 12.2° ± 0.2 °, 13.1° ± 0.2 °, 14.4 ° ± 0.2°, 16.7° ± 0.2°, 19.4° ± 0.2 °, 19.8° ± 0.2°, 21.8° ± 0.2 ° i 25.2° ± 0.2°.
18. Kristalni etanolni solvat prema patentnom zahtjevu 16, naznačen time što:
(a) kristalni etanolni solvat ima dijastereomernu čistoću između 90% do 99%; ili
(b) kristalni etanolni solvat ima dijastereomernu čistoću od najmanje 99%; ili
(c) kristalni etanolni solvat ima dijastereomernu čistoću od najmanje 90% i kemijsku čistoću od najmanje 80%; ili
(d) kristalni etanolni solvat ima kemijsku čistoću između 80% do 99%.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962884480P | 2019-08-08 | 2019-08-08 | |
| EP20758409.5A EP4010331B1 (en) | 2019-08-08 | 2020-08-07 | A method for preparing ivosidenib and an intermediate thereof |
| PCT/US2020/045368 WO2021026436A1 (en) | 2019-08-08 | 2020-08-07 | A method for preparing ivosidenib and an intermediate thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20231618T1 true HRP20231618T1 (hr) | 2024-03-15 |
Family
ID=74504162
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20231618TT HRP20231618T1 (hr) | 2019-08-08 | 2020-08-07 | Postupak za pripremu ivosideniba i njegovog intermedijara |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US20230025411A1 (hr) |
| EP (1) | EP4010331B1 (hr) |
| JP (1) | JP2022544143A (hr) |
| KR (1) | KR20220061971A (hr) |
| CN (1) | CN114555584A (hr) |
| AU (1) | AU2020327013A1 (hr) |
| BR (1) | BR112022002253A2 (hr) |
| CA (1) | CA3150028A1 (hr) |
| CL (1) | CL2022000310A1 (hr) |
| CO (1) | CO2022001991A2 (hr) |
| CR (1) | CR20220090A (hr) |
| DK (1) | DK4010331T3 (hr) |
| EC (1) | ECSP22016924A (hr) |
| ES (1) | ES2967909T3 (hr) |
| FI (1) | FI4010331T3 (hr) |
| HR (1) | HRP20231618T1 (hr) |
| HU (1) | HUE064193T2 (hr) |
| IL (1) | IL290377A (hr) |
| LT (1) | LT4010331T (hr) |
| MA (1) | MA56783B1 (hr) |
| MD (1) | MD4010331T2 (hr) |
| MX (1) | MX2022001619A (hr) |
| PE (1) | PE20221761A1 (hr) |
| PL (1) | PL4010331T3 (hr) |
| PT (1) | PT4010331T (hr) |
| RS (1) | RS64934B1 (hr) |
| SI (1) | SI4010331T1 (hr) |
| TW (1) | TW202120491A (hr) |
| WO (1) | WO2021026436A1 (hr) |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006067445A2 (en) | 2004-12-22 | 2006-06-29 | Astrazeneca Ab | Csf-1r kinase inhibitors |
| ATE541844T1 (de) | 2005-12-21 | 2012-02-15 | Abbott Lab | Antivirale verbindungen |
| US9474779B2 (en) * | 2012-01-19 | 2016-10-25 | Agios Pharmaceuticals, Inc. | Therapeutically active compositions and their methods of use |
| NZ723859A (en) | 2014-03-14 | 2023-01-27 | Servier Lab | Pharmaceutical compositions of therapeutically active compounds and their uses |
| WO2019104318A1 (en) * | 2017-11-27 | 2019-05-31 | Teva Pharmaceuticals Usa, Inc. | Solid state forms of ivosidenib |
| CA3103498A1 (en) * | 2018-07-06 | 2020-01-09 | Agios Pharmaceuticals, Inc. | Ivosidenib forms and pharmaceutical compositions |
| WO2020127887A1 (en) * | 2018-12-21 | 2020-06-25 | Sandoz Ag | Process for the preparation of an intermediate product of ivosidenib |
-
2020
- 2020-08-07 CR CR20220090A patent/CR20220090A/es unknown
- 2020-08-07 CA CA3150028A patent/CA3150028A1/en active Pending
- 2020-08-07 PT PT207584095T patent/PT4010331T/pt unknown
- 2020-08-07 BR BR112022002253A patent/BR112022002253A2/pt unknown
- 2020-08-07 US US17/634,524 patent/US20230025411A1/en active Pending
- 2020-08-07 MA MA56783A patent/MA56783B1/fr unknown
- 2020-08-07 SI SI202030329T patent/SI4010331T1/sl unknown
- 2020-08-07 CN CN202080070672.3A patent/CN114555584A/zh active Pending
- 2020-08-07 HR HRP20231618TT patent/HRP20231618T1/hr unknown
- 2020-08-07 TW TW109126862A patent/TW202120491A/zh unknown
- 2020-08-07 LT LTEPPCT/US2020/045368T patent/LT4010331T/lt unknown
- 2020-08-07 PL PL20758409.5T patent/PL4010331T3/pl unknown
- 2020-08-07 WO PCT/US2020/045368 patent/WO2021026436A1/en active Application Filing
- 2020-08-07 DK DK20758409.5T patent/DK4010331T3/da active
- 2020-08-07 ES ES20758409T patent/ES2967909T3/es active Active
- 2020-08-07 HU HUE20758409A patent/HUE064193T2/hu unknown
- 2020-08-07 MX MX2022001619A patent/MX2022001619A/es unknown
- 2020-08-07 RS RS20231183A patent/RS64934B1/sr unknown
- 2020-08-07 FI FIEP20758409.5T patent/FI4010331T3/fi active
- 2020-08-07 MD MDE20220658T patent/MD4010331T2/ro unknown
- 2020-08-07 AU AU2020327013A patent/AU2020327013A1/en active Pending
- 2020-08-07 EP EP20758409.5A patent/EP4010331B1/en active Active
- 2020-08-07 KR KR1020227007851A patent/KR20220061971A/ko active Search and Examination
- 2020-08-07 JP JP2022507572A patent/JP2022544143A/ja active Pending
- 2020-08-07 PE PE2022000203A patent/PE20221761A1/es unknown
-
2022
- 2022-02-06 IL IL290377A patent/IL290377A/en unknown
- 2022-02-07 CL CL2022000310A patent/CL2022000310A1/es unknown
- 2022-02-24 CO CONC2022/0001991A patent/CO2022001991A2/es unknown
- 2022-03-07 EC ECSENADI202216924A patent/ECSP22016924A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MA56783B1 (fr) | 2023-10-31 |
| RS64934B1 (sr) | 2023-12-29 |
| WO2021026436A1 (en) | 2021-02-11 |
| CA3150028A1 (en) | 2021-02-11 |
| CL2022000310A1 (es) | 2022-11-25 |
| TW202120491A (zh) | 2021-06-01 |
| PL4010331T3 (pl) | 2024-03-11 |
| MD4010331T2 (ro) | 2024-03-31 |
| AU2020327013A1 (en) | 2022-03-24 |
| EP4010331B1 (en) | 2023-10-04 |
| BR112022002253A2 (pt) | 2022-07-05 |
| IL290377A (en) | 2022-04-01 |
| LT4010331T (lt) | 2023-11-10 |
| ECSP22016924A (es) | 2022-06-30 |
| SI4010331T1 (sl) | 2024-02-29 |
| ES2967909T3 (es) | 2024-05-06 |
| CR20220090A (es) | 2022-08-24 |
| JP2022544143A (ja) | 2022-10-17 |
| EP4010331A1 (en) | 2022-06-15 |
| KR20220061971A (ko) | 2022-05-13 |
| PE20221761A1 (es) | 2022-11-11 |
| CO2022001991A2 (es) | 2022-07-29 |
| PT4010331T (pt) | 2024-01-08 |
| DK4010331T3 (da) | 2023-12-18 |
| HUE064193T2 (hu) | 2024-02-28 |
| FI4010331T3 (fi) | 2023-12-28 |
| US20230025411A1 (en) | 2023-01-26 |
| MX2022001619A (es) | 2022-07-19 |
| CN114555584A (zh) | 2022-05-27 |
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