HRP20210813T1 - Piridinonpiridinilni spojevi supstituirani s metil/fluorpiridinilmetoksi i piridinonpiridinilni spojevi supstituirani s fluorpirimidinilmetoksi - Google Patents

Piridinonpiridinilni spojevi supstituirani s metil/fluorpiridinilmetoksi i piridinonpiridinilni spojevi supstituirani s fluorpirimidinilmetoksi Download PDF

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HRP20210813T1
HRP20210813T1 HRP20210813TT HRP20210813T HRP20210813T1 HR P20210813 T1 HRP20210813 T1 HR P20210813T1 HR P20210813T T HRP20210813T T HR P20210813TT HR P20210813 T HRP20210813 T HR P20210813T HR P20210813 T1 HRP20210813 T1 HR P20210813T1
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methoxy
hydroxypropan
dimethyl
chloro
bromo
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HRP20210813TT
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Susan L. Hockerman
Joseph B. Monahan
Shaun R. Selness
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Aclaris Therapeutics, Inc.
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Claims (17)

1. Spoj Formule (I): [image] , ili njegova farmaceutski prihvatljiva sol, naznačen time što: X je CH ili N; R1 se bira iz skupine koju čine H, C1-C6 alkil, fluor, klor, brom, cijano ili -CF3; R2 se bira iz skupine koju čine H, metil, cijano ili fluor; R3 se bira iz skupine koju čine: [image] , [image] ili [image] ; R4 se bira iz skupine koju čine H, metil, OH, te O-CH3; R5 je H ili C1-C3 alkil; m je 1 ili 2; n je 0 ili 1; p je 1; i q je 0 ili 1.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time što spoj ima strukturu Formule (II): [image] , ili njegova farmaceutski prihvatljiva sol, gdje: X je CH ili N; R1 se bira iz skupine koju čine H, C1-C6 alkil, fluor, klor, brom, cijano ili -CF3; R2 se bira iz skupine koju čine H, metil, cijano ili fluor; R3 je [image] ; R4 se bira iz skupine koju čine H, metil, OH, te -OCH3; R5 je H ili C1-C3 alkil; m je 1 ili 2; i n je 0 ili 1.
3. Spoj u skladu s patentnim zahtjevom 2, naznačen time što se R3 bira iz skupine koju čine 3,5-difluorpiridin-2-il, 3-fluorpiridin-2-il, 5-fluor-3-metilpiridin-2-il, 6-fluorpiridin-2-il, 6-fluor-4-metilpiridin-2-il, 3-fluor-5-metilpiridin-2-il, te 5-fluorpiridin-2-il.
4. Spoj u skladu s patentnim zahtjevom 3, naznačen time što spoj ima strukturu Formule (III): [image] , ili njegova farmaceutski prihvatljiva sol, gdje: X je CH ili N; R1 je klor ili brom; i R2 je -H ili metil.
5. Spoj u skladu s patentnim zahtjevom 4, naznačen time što se spoj bira iz skupine koju čine: 3-brom-4-((3,5-difluorpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-3′′,5′,6-trimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-klor-4-((3,5-difluorpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-3′′,5′,6-trimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-brom-4-((3,5-difluorpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)-5-metilpirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-klor-4-((3,5-difluorpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)-5-metilpirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-brom-4-((3,5-difluorpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-5′,6-dimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-klor-4-((3,5-difluorpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-5′,6-dimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-brom-4-((3,5-difluorpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)pirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; i 3-klor-4-((3,5-difluorpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)pirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on.
6. Spoj u skladu s patentnim zahtjevom 5, naznačen time što je spoj 3-klor-4-((3,5-difluorpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)pirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on.
7. Spoj u skladu s patentnim zahtjevom 6, naznačen time što je spoj (–)-3-klor-4-((3,5-difluorpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)pirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on.
8. Spoj u skladu s patentnim zahtjevom 6, naznačen time što je spoj (+)-3-klor-4-((3,5-difluorpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)pirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on.
9. Spoj u skladu s patentnim zahtjevom 3, naznačen time što se spoj bira iz skupine koju čine: 3-klor-4-((5-fluorpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)pirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-klor-4-((3-fluorpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)pirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-klor-4-((5-fluor-3-metilpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)pirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-klor-4-((6-fluorpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)pirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-klor-4-((6-fluor-4-metilpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)pirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-klor-4-((3-fluor-5-metilpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)pirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-brom-4-((5-fluorpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)pirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-klor-4-((5-fluorpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-5′,6-dimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-brom-4-((5-fluorpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-5′,6-dimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-klor-4-((5-fluorpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)-5-metilpirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-brom-4-((5-fluorpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)-5-metilpirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-klor-4-((5-fluorpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-3′′,5′,6-trimetil-277-[1,4′:2′,2′′-terpiridin]-2-on; 3-brom-4-((5-fluorpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-3′′,5′,6-trimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-brom-4-((3-fluorpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)pirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-klor-4-((3-fluorpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-5′,6-dimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-brom-4-((3-fluorpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-5′,6-dimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-klor-4-((3-fluorpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)-5-metilpirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-brom-4-((3-fluorpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)-5-metilpirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-klor-4-((3-fluorpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-3′′,5′,6-trimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-brom-4-((3-fluorpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-3′′,5′,6-trimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-brom-4-((5-fluor-3-metilpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)pirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-klor-4-((5-fluor-3-metilpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-5′,6-dimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-brom-4-((5-fluor-3-metilpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-5′,6-dimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-klor-4-((5-fluor-3-metilpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)-5-metilpirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-brom-4-((5-fluor-3-metilpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)-5-metilpirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-klor-4-((5-fluor-3-metilpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-3′′,5′,6-trimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-brom-4-((5-fluor-3-metilpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-3′′,5′,6-trimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-brom-4-((6-fluorpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)pirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-klor-4-((6-fluorpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-5′,6-dimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-brom-4-((6-fluorpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-5′,6-dimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-klor-4-((6-fluorpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)-5-metilpirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-brom-4-((6-fluorpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)-5-metilpirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-klor-4-((6-fluorpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-3′′,5′,6-trimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-brom-4-((6-fluorpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-3′′,5′,6-trimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-brom-4-((6-fluor-4-metilpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)pirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-klor-4-((6-fluor-4-metilpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-5′,6-dimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-brom-4-((6-fluor-4-metilpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-5′,6-dimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-klor-4-((6-fluor-4-metilpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)-5-metilpirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-brom-4-((6-fluor-4-metilpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)-5-metilpirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-klor-4-((6-fluor-4-metilpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-3′′,5′,6-trimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-brom-4-((6-fluor-4-metilpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-3′′,5′,6-trimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-brom-4-((3-fluor-5-metilpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)pirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-klor-4-((3-fluor-5-metilpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-5′,6-dimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-brom-4-((3-fluor-5-metilpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-5′,6-dimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-klor-4-((3-fluor-5-metilpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)-5-metilpirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-brom-4-((3-fluor-5-metilpiridin-2-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)-5-metilpirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-klor-4-((3-fluor-5-metilpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-3′′,5′,6-trimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; i 3-brom-4-((3-fluor-5-metilpiridin-2-il)metoksi)-6′′-(2-hidroksipropan-2-il)-3′′,5′,6-trimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on.
10. Spoj u skladu s patentnim zahtjevom 1, naznačen time što spoj ima strukturu Formule (IV): [image] , ili njegova farmaceutski prihvatljiva sol, gdje: X je CH ili N; R1 se bira iz skupine koju čine H, C1-C6 alkil, fluor, klor, brom, cijano ili -CF3; R2 se bira iz skupine koju čine H, metil, cijano ili fluor; R4 se bira iz skupine koju čine H, metil, OH, te -OCH3; R5 je H ili C1-C3 alkil; m je 1 ili 2; i n je 0 ili 1.
11. Spoj u skladu s patentnim zahtjevom 10, naznačen time što spoj ima strukturu Formule (V): [image] , ili njegova farmaceutski prihvatljiva sol, gdje: X je CH ili N; R1 je klor ili brom; i R2 je -H ili metil.
12. Spoj u skladu s patentnim zahtjevom 11, naznačen time što se spoj bira iz skupine koju čine: 3-klor-4-((4-fluorpiridin-3-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)pirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-brom-4-((4-fluorpiridin-3-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)pirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-klor-4-((4-fluorpiridin-3-il)metoksi)-6′′-(2-hidroksipropan-2-il)-5′,6-dimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-brom-4-((4-fluorpiridin-3-il)metoksi)-6′′-(2-hidroksipropan-2-il)-5′,6-dimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-klor-4-((4-fluorpiridin-3-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)-5-metilpirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-brom-4-((4-fluorpiridin-3-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)-5-metilpirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-klor-4-((4-fluorpiridin-3-il)metoksi)-6′′-(2-hidroksipropan-2-il)-3′′,5′,6-trimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; i 3-brom-4-((4-fluorpiridin-3-il)metoksi)-6′′-(2-hidroksipropan-2-il)-3′′,5′,6-trimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on.
13. Spoj u skladu s patentnim zahtjevom 1, naznačen time što spoj ima strukturu Formule (VI): [image] , ili njegova farmaceutski prihvatljiva sol, gdje: X je CH ili N; R1 se bira iz skupine koju čine H, C1-C6 alkil, fluor, klor, brom, cijano ili -CF3; R2 se bira iz skupine koju čine H, metil, cijano ili fluor; R4 se bira iz skupine koju čine H, metil, OH, te -OCH3; R5 je H ili C1-C3 alkil; p je 1; i q je 0 ili 1.
14. Spoj u skladu s patentnim zahtjevom 13, naznačen time što spoj ima strukturu Formule (VII): [image] , ili njegova farmaceutski prihvatljiva sol, gdje: X je CH ili N; R1 je klor ili brom; i R2 je -H ili metil.
15. Spoj u skladu s patentnim zahtjevom 14, naznačen time što se spoj bira iz skupine koju čine: 3-klor-4-((5-fluorpirimidin-4-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)pirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-brom-4-((5-fluorpirimidin-4-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)pirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-klor-4-((5-fluorpirimidin-4-il)metoksi)-6′′-(2-hidroksipropan-2-il)-5′,6-dimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-brom-4-((5-fluorpirimidin-4-il)metoksi)-6′′-(2-hidroksipropan-2-il)-5′,6-dimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; 3-klor-4-((5-fluorpirimidin-4-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)-5-metilpirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-brom-4-((5-fluorpirimidin-4-il)metoksi)-2′-(2-(2-hidroksipropan-2-il)-5-metilpirimidin-4-il)-5′,6-dimetil-2H-[1,4′-bipiridin]-2-on; 3-klor-4-((5-fluorpirimidin-4-il)metoksi)-6′′-(2-hidroksipropan-2-il)-3′′,5′,6-trimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on; i 3-brom-4-((5-fluorpirimidin-4-il)metoksi)-6′′-(2-hidroksipropan-2-il)-3′′,5′,6-trimetil-2H-[1,4′:2′,2′′-terpiridin]-2-on.
16. Farmaceutski pripravak, naznačen time što sadrži terapijski djelotvornu količinu spoja u skladu s patentnim zahtjevom 1, ili njegove farmaceutski prihvatljive soli, kao i farmaceutski prihvatljivi nosač.
17. Farmaceutski pripravak u skladu s patentnim zahtjevom 16, naznačen time što dodatno sadrži terapijski djelotvornu količinu aktivnog farmaceutskog sastojka kojeg se bira iz skupine koju čine protuupalni lijekovi, antiaterosklerotički lijekovi, imunosuppresivni lijekovi, imunomodulacijski lijekovi, citostatički lijekovi, inhibitori angiogeneze, inhibitori kinaza, blokatori citokina i inhibitori molekula stanične adhezije.
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