HRP20221446T1 - Postupci za pripremu n-(5-(3-(7-(3-fluorofenil)-3h-imidazo[4,5-c]piridin-2-il)-1h-indazol-5-il)piridin-3-il)-3-metilbutanamida - Google Patents
Postupci za pripremu n-(5-(3-(7-(3-fluorofenil)-3h-imidazo[4,5-c]piridin-2-il)-1h-indazol-5-il)piridin-3-il)-3-metilbutanamida Download PDFInfo
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- AQDWDWAYVBQMAM-UHFFFAOYSA-N N-[5-[3-[7-(3-fluorophenyl)-3H-imidazo[4,5-c]pyridin-2-yl]-1H-indazol-5-yl]pyridin-3-yl]-3-methylbutanamide Chemical compound CC(C)CC(=O)NC1=CN=CC(C=2C=C3C(C=4NC5=CN=CC(=C5N=4)C=4C=C(F)C=CC=4)=NNC3=CC=2)=C1 AQDWDWAYVBQMAM-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 99
- 150000003839 salts Chemical class 0.000 claims 75
- 238000000034 method Methods 0.000 claims 27
- 239000000203 mixture Substances 0.000 claims 26
- 238000006243 chemical reaction Methods 0.000 claims 14
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical group CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 12
- 239000007787 solid Substances 0.000 claims 11
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 10
- 239000012458 free base Substances 0.000 claims 10
- 238000010511 deprotection reaction Methods 0.000 claims 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 8
- 238000001914 filtration Methods 0.000 claims 7
- 239000003495 polar organic solvent Substances 0.000 claims 6
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims 5
- 150000003891 oxalate salts Chemical class 0.000 claims 5
- 238000001556 precipitation Methods 0.000 claims 5
- 238000002360 preparation method Methods 0.000 claims 5
- 230000001376 precipitating effect Effects 0.000 claims 4
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims 2
- 239000012298 atmosphere Substances 0.000 claims 2
- 239000000706 filtrate Substances 0.000 claims 2
- 239000012299 nitrogen atmosphere Substances 0.000 claims 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims 2
- 235000010265 sodium sulphite Nutrition 0.000 claims 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims 2
- 229910000404 tripotassium phosphate Inorganic materials 0.000 claims 2
- 235000019798 tripotassium phosphate Nutrition 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 claims 1
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- 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
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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
- A61K31/4439—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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- 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
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- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Neurosurgery (AREA)
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- Biomedical Technology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (26)
1. Postupci za pripremu spoja Formule (1)
[image]
ili njegove soli, te postupci obuhvaćaju:
(a) reakciju spoja Formule (8)
[image]
ili njegove soli, sa bis(pinakolato)diboronom i Pd(dppf)Cl2 da se dobije spoj s Formulom (9)
[image]
ili njegova sol;
(b) reakciju spoja Formule (9), ili njegove soli, sa spojem s Formulom (10)
[image]
ili njegovom soli, s Pd(PPh3)4 i K3PO4 da se dobije spoj s Formulom (11)
[image]
ili njegova sol,
(c) reakciju spoja Formule (11), ili njegove soli, sa spojem s Formulom (6)
[image]
ili njegovom soli, da se dobije spoj s Formulom (12)
[image]
ili njegova sol; i
(d) uklanjanje zaštite sa spoja Formule (12), ili njegove soli, da se dobije spoj Formule (1), ili njegova sol, pri čemu uklanjanje zaštite sa spoja Formule (12) da se dobije spoj Formule (1) obuhvaća reakciju spoja Formule (12) s čistom trifluorooctenom kiselinom (TFA).
2. Postupak prema zahtjevu 1, naznačen time što je omjer molarnih ekvivalenata Pd(dppf)Cl2 prema spoju s Formulom (8), ili njegovoj soli, oko 0,01:1 do oko 0,1:1, poželjno oko 0,03:1.
3. Postupak prema zahtjevu 1, naznačen time što je omjer molarnih ekvivalenata Pd(PPh3)4 prema spoju s Formulom (9), ili njegovoj soli, oko 0,01:1 do oko 0,1:1, poželjno oko 0.03:1.
4. Postupak prema bilo kojem od zahtjeva 1-3, naznačen time što je omjer K3PO4 prema spoju s Formulom (10), ili njegovoj soli, oko 3:1.
5. Postupak prema bilo kojem od zahtjeva 1-4, naznačen time što se reakcija spoja Formule (9), ili njegove soli, sa spojem Formule (10), ili njegovom soli, da se dobije spoj s Formulom (11), ili njegova sol, provodi se u prisutnosti 1,4-dioksana.
6. Postupak prema bilo kojem od zahtjeva 1-5, naznačen time što se reakcija spoja Formule (9), ili njegove soli, sa spojem Formule (10), ili njegovom soli, da se dobije spoj s Formulom (11), ili njegova sol, provodi se u inertnoj atmosferi, poželjno u atmosferi N2.
7. Postupak prema bilo kojem od zahtjeva 1-6, naznačen time što se reakcija spoja Formule (9), ili njegove soli, sa spojem Formule (10), ili njegovom soli, da se dobije spoj s Formulom (11), ili njegova sol, provodi na temperaturi od oko 80°C do oko 100°C tijekom vremena od oko 1 sat do oko 5 sati, poželjno na temperaturi od oko 85°C do oko 95°C tijekom vremena od oko 2 sata do oko 3 sata.
8. Postupak prema bilo kojem od zahtjeva 1-7, naznačen time što nadalje obuhvaća taloženje spoja s Formulom (11) u vodi prije reakcije spoja Formule (11), ili njegove soli, sa spojem s Formulom (6), ili njegovom soli, da se dobije spoj s Formulom (12), ili njegova sol.
9. Postupak prema bilo kojem od zahtjeva 1-8, naznačen time što nadalje obuhvaća pripremu soli spoja s Formulom (11) prije reakcije spoja Formule (11), ili njegove soli, sa spojem s Formulom (6), ili njegovom soli, da se dobije spoj s Formulom (12), ili njegova sol, poželjno oksalatne soli spoja s Formulom (11).
10. Postupak prema bilo kojem od zahtjeva 1-9, naznačen time što nadalje obuhvaća pripremu oblika slobodne baze spoja s Formulom (11) prije reakcije spoja Formule (11), ili njegove soli, sa spojem s Formulom (6), ili njegovom soli, da se dobije spoj s Formulom (12), ili njegova sol.
11. Postupak prema bilo kojem od zahtjeva 1-10, naznačen time što nadalje obuhvaća taloženje spoja s Formulom (11), ili njegove soli, u nepolarnom organskom otapalu prije reakcije spoja Formule (11), ili njegove soli, sa spojem s Formulom (6), ili njegovom soli, da se dobije spoj s Formulom (12), ili njegova sol, poželjno nepolarno organsko otapalo je n-heptan.
12. Postupak prema zahtjevu 1, naznačen time što nadalje obuhvaća jedno ili više od:
(a) taloženje spoja s Formulom (11) u vodi;
(b) pripremanje soli spoja s Formulom (11) iz istaloženog spoja s Formulom (11);
(c) pripremanje oblika slobodne baze spoja s Formulom (11) iz soli spoja s Formulom (11); i
(d) taloženje oblika slobodne baze spoja s Formulom (11) u nepolarnom organskom otapalu, prije reakcije spoja Formule (11), ili njegove soli, sa spojem s Formulom (6), ili njegovom soli, da se dobije spoj s Formulom (12), ili njegova sol.
13. Postupak prema zahtjevu 1, naznačen time što nadalje obuhvaća jedno ili više od:
(a) taloženje spoja s Formulom (11) u vodi;
(b) pripremanje oksalatne soli spoja s Formulom (11) iz istaloženog spoja s Formulom (11);
(c) pripremanje oblika slobodne baze spoja s Formulom (11) iz soli spoja s Formulom (11); i
(d) taloženje oblika slobodne baze spoja s Formulom (11) u n-heptanu, prije reakcije spoja Formule (11), ili njegove soli, sa spojem s Formulom (6), ili njegovom soli, da se dobije spoj s Formulom (12), ili njegova sol.
14. Postupak prema bilo kojem od zahtjeva 1-13, naznačen time što se reakcija spoja Formule (11), ili njegove soli, sa spojem s Formulom (6), ili njegovom soli, da se dobije spoj s Formulom (12), ili njegova sol, provodi u prisutnosti Na2SO3, poželjno mljevenog Na2SO3.
15. Postupak prema bilo kojem od zahtjeva 1-14, naznačen time što se reakcija spoja Formule (11), ili njegove soli, sa spojem s Formulom (6), ili njegovom soli, da se dobije spoj s Formulom (12), ili njegova sol, provodi se u prisutnosti N-metil-2-pirolidona.
16. Postupak prema bilo kojem od zahtjeva 1-15, naznačen time što se reakcija spoja Formule (11), ili njegove soli, sa spojem s Formulom (6), ili njegovom soli, da se dobije spoj s Formulom (12), ili njegova sol, provodi u inertnoj atmosferi, poželjno atmosferi N2 .
17. Postupak prema bilo kojem od zahtjeva 1-16, naznačen time što se reakcija spoja Formule (11), ili njegove soli, sa spojem s Formulom (6), ili njegovom soli, da se dobije spoj s Formulom (12), ili njegova sol, provodi se na temperaturi od oko 100°C do oko 120°C tijekom vremena od oko 5 sati do oko 10 sati, poželjno na temperaturi od oko 110°C do oko 115°C tijekom vremena od oko 7 sati do oko 9 sati.
18. Postupak prema bilo kojem od zahtjeva 1-17, naznačen time što nadalje obuhvaća pripremu soli spoja Formule (12) prije uklanjanja zaštite sa spoja s Formulom (12), ili njegove soli, da se dobije spoj s Formulom (1), ili njegova sol, poželjno oksalatna sol spoja s Formulom (12).
19. Postupak prema bilo kojem od zahtjeva 1-18, naznačen time što nadalje obuhvaća pripremu oblika slobodne baze spoja s Formulom (12) prije uklanjanja zaštite sa spoja s Formulom (12), ili njegove soli, da se dobije spoj s Formulom (1), ili njegova sol.
20. Postupak prema bilo kojem od zahtjeva 1-19, naznačen time što nadalje obuhvaća taloženje spoja s Formulom (12), ili njegove soli, u nepolarnom organskom otapalu prije uklanjanja zaštite sa spoja s Formulom (12), ili njegove soli, da se dobije spoj s Formulom (1), ili njegova sol, poželjno nepolarno organsko otapalo je n-heptan.
21. Postupak prema bilo kojem od zahtjeva 1-20, naznačen time što nadalje obuhvaća jedno ili više od:
(a) pripremanje soli spoja s Formulom (12);
(b) pripremanje oblika slobodne baze spoja s Formulom (12) iz soli spoja s Formulom (12); i
(c) taloženje oblika slobodne baze spoja s Formulom (12) u nepolarnom organskom otapalu, prije uklanjanja zaštite sa spoja s Formulom (12), ili njegove soli, da se dobije spoj s Formulom (1), ili njegova sol.
22. Postupak prema bilo kojem od zahtjeva 1-21, naznačen time što nadalje obuhvaća jedno ili više od:
(a) pripremanje oksalatne soli spoja s Formulom (12);
(b) pripremanje oblika slobodne baze spoja s Formulom (12) iz oksalatne soli spoja s Formulom (12); i
(c) taloženje oblika slobodne baze spoja s Formulom (12) u n-heptanu, prije uklanjanja zaštite sa spoja s Formulom (12), ili njegovom soli, da se dobije spoj s Formulom (1), ili njegova sol.
23. Postupak prema bilo kojem od zahtjeva 1-22, je omjer masenih ekvivalenata TFA prema spoju s Formulom (12), ili njegovoj soli, oko 2:1 do oko 16:1, poželjno oko 8:1.
24. Postupak prema bilo kojem od zahtjeva 1-23, naznačen time što se uklanjanje zaštite sa spoja s Formulom (12), ili njegove soli, provodi na temperaturi od oko 15°C do oko 25°C u vremenu od oko 2 sata do oko 7 sati, poželjno oko 5 sati, poželjnije oko 3 sata.
25. Postupak prema bilo kojem od zahtjeva 1-24, naznačen time što se uklanjanje zaštite sa spoja s Formulom (12), ili njegove soli, obuhvaća:
stvaranje prve smjese spoja s Formulom (12) s čistom trifluorooctenom kiselinom (TFA);
dodavanje vode u prvu smjesu na temperaturi od oko 0°C do oko 10°C da nastane druga smjesa;
ponovno suspendiranje druge smjese u vremenu od oko 0,5 sati do oko 1 sat na temperaturi od oko 0°C do oko 10°C;
filtriranje druge smjese da se dobije filtrat;
dodavanje vode u filtrat na temperaturi od oko 0°C do oko 10°C da se dobije treća smjesa,
ponovno suspendiranje treće smjese na temperaturi od oko 5°C do oko 15°C kroz vrijeme od oko 1 sat do oko 2 sata; i
filtriranje treće smjese da se dobije prva rezidualna krutina.
26. Postupak prema zahtjevu 25, naznačen time što nadalje obuhvaća:
dodavanje etanola u prvu rezidualnu krutinu da se dobije četvrta smjesa;
ponovno suspendiranje četvrte smjese na temperaturi od oko 25°C do oko 35°C tijekom vremena od oko 2 sata do oko 4 sata;
filtriranje četvrte smjese da se dobije druga rezidualna krutina;
dodavanje vode u drugu rezidualnu krutinu da se dobije peta smjesa;
ponovno suspendiranje pete smjese na temperaturi od oko 20°C do oko 30°C tijekom vremena od oko 0,5 sata do oko 1,5 sat;
dodavanje baze u petu smjesu da se dobije šesta smjesa;
ponovno suspendiranje šeste smjese na temperaturi od oko 20°C do oko 30°C tijekom vremena od oko 5 sati do oko 7 sati;
filtriranje šeste smjese da se dobije treća rezidualna krutina;
dodavanje vode u treću rezidualnu krutinu da se dobije sedma smjesa;
ponovno suspendiranje sedme smjese na temperaturi od oko 20°C do oko 30°C tijekom vremena od oko 5 sati do oko 8 sati;
filtriranje sedme smjese da se dobije četvrta rezidualna krutina;
dodavanje vode u četvrtu rezidualnu krutinu da se dobije osma smjesa;
ponovno suspendiranje osme smjese;
filtriranje osme smjese da se dobije peta rezidualna krutina;
dodavanje izopropanola u petu rezidualnu krutinu da se dobije deveta smjesa;
ponovno suspendiranje devete smjese na temperaturi od oko 20°C do oko 30°C tijekom vremena od oko 1 sat do oko 3 sata; i
filtriranje devete smjese da se dobije šesta rezidualna krutina.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662344170P | 2016-06-01 | 2016-06-01 | |
| US201662418657P | 2016-11-07 | 2016-11-07 | |
| PCT/US2017/035411 WO2017210407A1 (en) | 2016-06-01 | 2017-06-01 | Process for preparing n-(5-(3-(7-(3-fluorophenyl)-3h-imidazo[4,5-c]pyridin-2-yl)-1h-indazol-5-yl)pyridin-3-yl)-3-methylbutanamide |
| EP17729694.4A EP3464285B1 (en) | 2016-06-01 | 2017-06-01 | Process for preparing n-(5-(3-(7-(3-fluorophenyl)-3h-imidazo[4,5-c]pyridin-2-yl)-1h-indazol-5-yl)pyridin-3-yl)-3-methylbutanamide |
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| Publication Number | Publication Date |
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| HRP20221446T1 true HRP20221446T1 (hr) | 2023-01-06 |
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