DK2794627T3 - Substituerede nukleosider, nukleotider og analoger deraf - Google Patents

Substituerede nukleosider, nukleotider og analoger deraf Download PDF

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DK2794627T3
DK2794627T3 DK12860391.7T DK12860391T DK2794627T3 DK 2794627 T3 DK2794627 T3 DK 2794627T3 DK 12860391 T DK12860391 T DK 12860391T DK 2794627 T3 DK2794627 T3 DK 2794627T3
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optionally substituted
alkyl
compound
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hydrogen
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Leonid Beigelman
Guangyi Wang
David Bernard Smith
Jerome Deval
Marija Prhavc
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Alios Biopharma Inc
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Claims (48)

1. Forbindelse med formlen (I) eller et farmaceutisk acceptabelt salt deraf:
hvor: B1A er valgt fra gruppen bestående af:
hvor: RA2 er valgt fra gruppen bestående af hydrogen, halogen og NHRJ2, hvor RJ2 er valgt fra gruppen bestående af hydrogen, C(=O)RK2 og -C(=O)ORL2; RB2 er halogen eller NHRW2, hvor Rw2 er valgt fra gruppen bestående af hydrogen, en eventuelt substitueret Ci-6-alkyl, en eventuelt substitueret C2-6-alkenyl, en eventuelt substitueret C3-8-cycloalkyl, -C(=O)RM2 og -C(=O)ORN2; Rc2 er hydrogen eller NHR02, hvor R02 er valgt fra gruppen bestående af hydrogen, -C(=O)RP2 og -C(=O)ORQ2; RD2 er valgt fra gruppen bestående af hydrogen, halogen, en eventuelt substitueret Ci-6-alkyl, en eventuelt substitueret C2-6-alkenyl og en eventuelt substitueret C2-6-alkynyl; RE2 er valgt fra gruppen bestående af hydrogen, hydroxy, en eventuelt substitueret Ci-6-alkyl, en eventuelt substitueret C3-8-cycloalkyl, -C(=O)RR2 og -C(=O)ORS2; RF2 er valgt fra gruppen bestående af hydrogen, halogen, en eventuelt substitueret Ci-6-alkyl, en eventuelt substitueret C2-
6-alkenyl og en eventuelt substitueret C2-6-alkynyl ; Y2 og Y3 er uafhængigt N eller CR12, hvor R12 er valgt fra gruppen bestående af hydrogen, halogen, en eventuelt substitueret Ci-6-alkyl, en eventuelt substitueret C2-6-alkenyl og en eventuelt substitueret C2-6-alkynyl; RG2 er en eventuelt substitueret Ci-6-alkyl; RH2 er hydrogen eller NHRT2, hvor RT2 er valgt fra gruppen bestående af hydrogen, -C(=O)RU2 og -C(=O)ORV2; og RK2, RL2, RM2, RN2, Rp2, RQ2, RR2, Rs2, Ru2 og Rv2 er uafhængigt valgt fra gruppen bestående af Ci-6-alkyl, C2-6-alkenyl, C2-6- alkynyl, C3-6-cycloalkyl, C3-6-cycloalkenyl, C6-io-aryl, heteroaryl, heteroalicyklyl, aryl (Ci-6-alkyl) , heteroaryl (C1-6-alkyl) og heteroalicyklyl (Ci-6-alkyl) ; R1A er valgt fra gruppen bestående af hydrogen, en eventuelt substitueret acyl, en eventuelt substitueret O-bundet aminosyre,
den stiplede linje (------) f formel (I) er fraværende; R2A er valgt fra gruppen bestående af en ikke-substitueret C1-6-alkyl, en halogen-substitueret Ci-6-alkyl, en hydroxy-substitueret Ci-6-alkyl, en alkoxy-substitueret Ci-6-alkyl og en sulfenyl-subs ti tueret Ci-6-alkyl ; R3A er valgt fra gruppen bestående af OH, -OC(=O)R"A og en eventuelt substitueret O-bundet aminosyre; R4A er fluor; R5A er hydrogen; r6a, r7a og r8a er uafhængigt valgt fra gruppen bestående af fraværende, hydrogen, en eventuelt substitueret Ci-24-alkyl, en eventuelt substitueret C2-24-alkenyl, en eventuelt substitueret C2-24-alkynyl, en eventuelt substitueret C3-6-cycloalkyl, en eventuelt substitueret C3-6-cycloalkenyl, en eventuelt substitueret aryl, en eventuelt substitueret heteroaryl, en eventuelt substitueret aryl(Ci-6-alkyl), en eventuelt substitueret * - (CR15AR16A) p-O-Ci-24-alkyl, en eventuelt substitueret *- (CR17AR18A) q-O-Ci-24-alkenyl,
eller R6A er
og R7A er fraværende eller hydrogen; eller R6A og R7A er taget sammen for at danne en del valgt fra gruppen bestående af en eventuelt substitueret
og en eventuelt substitueret
hvor oxygenatomerne, der er forbundet med R6A og R7A, phosphor og delen danner et seks- til ti-leddet ringsystem;. R9A er valgt fra gruppen bestående af en eventuelt substitueret Ci-24-alkyl, en eventuelt substitueret C2-24-alkenyl, en eventuelt substitueret C2-24-alkynyl, en eventuelt substitueret C3-6-cycloalkyl, en eventuelt substitueret C3-6-cycloalkenyl, NR30AR31A, en eventuelt substitueret N-bundet aminosyre og et eventuelt substitueret N-bundet aminosyre-esterderivat; R10A og R11A er uafhængigt en eventuelt substitueret N-bundet aminosyre eller et eventuelt substitueret N-bundet aminosyre-esterderivat ; R12A, R13A og R14A er uafhængigt fraværende eller hydrogen;
hver R15A, hver R16A, hver R17A og hver R18A er uafhængigt hydrogen, en eventuelt substitueret Ci-24-alkyl eller alkoxy; R19A, R20A, R22A og R23A er uafhængigt valgt fra gruppen bestående af hydrogen, en eventuelt substitueret Ci-24-alkyl og en eventuelt substitueret aryl; R21A og R24A er uafhængigt valgt fra gruppen bestående af hydrogen, en eventuelt substitueret Ci-24-alkyl, en eventuelt substitueret aryl, en eventuelt substitueret -O-Ci-24-alkyl og en eventuelt substitueret -O-aryl; R25A og r29a er uafhængigt valgt fra gruppen bestående af hydrogen, en eventuelt substitueret Ci-24-alkyl og en eventuelt substitueret aryl; R26A og R27A er uafhængigt -C^N eller en eventuelt substitueret substituent valgt fra gruppen bestående af C2-8-organylcarbonyl, C2-8-alkoxycarbonyl og C2-8- organylaminocarbonyl; R28A er valgt fra gruppen bestående af hydrogen, en eventuelt substitueret Ci-24-alkyl, en eventuelt substitueret C2-24-alkenyl, en eventuelt substitueret C2-24-alkynyl, en eventuelt substitueret C3-6-cycloalkyl og en eventuelt substitueret C3-6-cycloalkenyl ; R30A og R31A er uafhængigt valgt fra gruppen bestående af hydrogen, en eventuelt substitueret Ci-24-alkyl, en eventuelt substitueret C2-24-alkenyl, en eventuelt substitueret C2-24-alkynyl, en eventuelt substitueret C3-6-cycloalkyl og en eventuelt substitueret C3-6-cycloalkenyl; R"A er en eventuelt substitueret Ci-24-alkyl; m er 0 eller 1; p og q er uafhængigt valgt fra gruppen bestående af 1, 2 og 3; r er 1 eller 2; og Z1A, Z2A, Z3A og Z4A er uafhængigt 0 eller S.
2. Forbindelse ifølge krav 1, hvor R1A er
eller
hvor Z1A, Z2A og Z3A hver er 0.
3. Forbindelse ifølge krav 2, hvor den ene af R6A og R7A er hydrogen, og den anden af R6A og R7A er valgt fra gruppen bestående af en eventuelt substitueret Ci-24-alkyl, en eventuelt substitueret C2-24-alkenyl, en eventuelt substitueret C2-24-alkynyl, en eventuelt substitueret C3-6-cycloalkyl, en eventuelt substitueret C3-6-cycloalkenyl, en eventuelt substitueret aryl, en eventuelt substitueret heteroaryl og en eventuelt substitueret aryl (Ci-6-alkyl) , den anden af R6A og R7A fortrinsvis er en eventuelt substitueret Ci-24-alkyl; eller R6A og R7A begge er uafhængigt valgt fra gruppen bestående af en eventuelt substitueret Ci-24-alkyl, en eventuelt substitueret C2-24-alkenyl, en eventuelt substitueret C2-24-alkynyl, en eventuelt substitueret C3-6-cycloalkyl, en eventuelt substitueret C3-6-cycloalkenyl, en eventuelt substitueret aryl, en eventuelt substitueret heteroaryl og en eventuelt substitueret aryl (Ci-6-alkyl) , R6A og R7A fortrinsvis begge er en eventuelt substitueret Ci-24-alkyl; eller den ene af R6A og R7A er valgt fra gruppen bestående af og den anden af
R6A og R7A er valgt fra gruppen bestående af fraværende, hydrogen, en eventuelt substitueret Ci-24-alkyl, en eventuelt substitueret C2-24-alkenyl, en eventuelt substitueret C2-24-alkynyl, en eventuelt substitueret C3-6-cycloalkyl, en eventuelt substitueret C3-6-cycloalkenyl, en eventuelt substitueret aryl, en eventuelt substitueret heteroaryl og en eventuelt substitueret aryl (Ci-6-alkyl) , R6A og R7A fortrinsvis
begge er uafhænqiqt
valqt fra gruppen bestående af R6A og R7A fortrinsvis begge er
R6A og R7A fortrinsvis begge er
R6A og R7A fortrinsvis begge er
eller R6A og R7A begge er en eventuelt substitueret Ci-24-alkyl; eller R6A og R7A begge er en eventuelt substitueret C2-24- alkenyl; eller R6A og R7A begge er *-(CR15AR16A) p-O-Ci-24-alkyl; eller R6A og R7A begge er *-(CR17AR19A) q-O-C2-24-alkenyl; eller R6A og R7A begge er en eventuelt substitueret aryl; eller R6A og R7A begge er en eventuelt substitueret aryl (Ci-6-alkyl) ; eller R6A og R7A begge er
eller R6A og R7A begge er
eller R6A og R7A er taget sammen for at danne en del valgt fra
gruppen bestående af en eventuelt substitueret
og en eventuelt substitueret
hvor oxygenatomerne, der er forbundet med R6A og R7A, phosphor og delen danner et seks- til ti-leddet ringsystem, R6A og R7A fortrinsvis er taget sammen for at danne en del valgt fra gruppen bestående af
hvor R32A er en eventuelt substitueret aryl, en eventuelt substitueret heteroaryl eller en eventuelt substitueret heterocyclyl.
4. Forbindelse ifølge krav 2, hvor R8A er valgt fra gruppen bestående af fraværende, hydrogen, en eventuelt substitueret Ci-24-alkyl, en eventuelt substitueret C2-24-alkenyl, en eventuelt substitueret C2-24~alkynyl, en eventuelt substitueret C3-6-cycloalkyl og en eventuelt substitueret C3-6-cycloalkenyl, og R9A er valgt fra gruppen bestående af en eventuelt substitueret Ci-24-alkyl, en eventuelt substitueret C2-24-alkenyl, en eventuelt substitueret C2-24~alkynyl, en eventuelt substitueret C3-6-cycloalkyl og en eventuelt substitueret C3-6-cycloalkenyl, R8A fortrinsvis er hydrogen, og R9A er en
eventuelt substitueret Ci-6-alkyl; eller R8A er hydrogen, og R9A er NR30AR31A, hvor R30A og R31A er uafhængigt valgt fra gruppen bestående af hydrogen, en eventuelt substitueret Ci-24-alkyl, en eventuelt substitueret C2-24-alkenyl, en eventuelt substitueret C2-2-alkynyl, en eventuelt substitueret C3-6-cycloalkyl og en eventuelt substitueret C3-6-cycloalkenyl; eller R8A er fraværende eller hydrogen, og R9A er en eventuelt substitueret N-bundet aminosyre eller et eventuelt substitueret N-bundet aminosyre-esterderivat; eller R8A er en eventuelt substitueret aryl, og R9A er en eventuelt substitueret N-bundet aminosyre eller et eventuelt substitueret N-bundet aminosyre-esterderivat .
5. Forbindelse ifølge krav 2, hvor R10A og R11A begge er en eventuelt substitueret N-bundet aminosyre eller et eventuelt substitueret N-bundet aminosyre-esterderivat, R10A og R11A fortrinsvis er uafhængigt valgt fra gruppen bestående af alanin, asparagin, aspartat, cystein, glutamat, glutamin, glycin, prolin, serin, tyrosin, arginin, histidin, isoleucin, leucin, lysin, methionin, phenylalanin, threonin, tryptophan, valin og esterderivater deraf, R10A og R11A fortrinsvis er uafhængigt valgt fra gruppen bestående af alanin-isopropylester, alanin-cyclohexylester, alanin-neopentylester, valin-isopropylester og leucin-isopropylester; eller R10A og R11A uafhængigt har strukturen
hvor r36a er valgt fra gruppen bestående af hydrogen, en eventuelt substitueret Ci-6-alkyl, en eventuelt substitueret C3-6-cycloalkyl, en eventuelt substitueret aryl, en eventuelt substitueret aryl(Ci-6-alkyl) og en eventuelt substitueret halogenalkyl, R37A er valgt fra gruppen bestående af hydrogen, en eventuelt substitueret Ci-6-alkyl, en eventuelt substitueret Ci-6-halogenalkyl, en eventuelt substitueret C3-6-cycloalkyl, en eventuelt substitueret C6-aryl, en eventuelt substitueret C10-aryl og en eventuelt substitueret aryl (Ci-6-alkyl) , og R38A er hydrogen eller en eventuelt substitueret Ci-4-alkyl; eller
R37A og R38A er taget sammen for at danne en eventuelt substitueret C3-6-cycloalkyl, R37A fortrinsvis er en eventuelt substitueret Ci-6-alkyl, R37A fortrinsvis er methyl, R38A fortrinsvis er hydrogen, r36a fortrinsvis er en eventuelt substitueret Ci-6-alkyl, en eventuelt substitueret C3-6-cycloalkyl eller en eventuelt substitueret benzyl.
6. Forbindelse ifølge krav 1, hvor R1A er hvor R6A og R7A begge er hydrogen, eller R6A og R7A begge er fraværende; eller R1A er
hvor R6A er
m fortrinsvis er 0, og R7A, R12A og R13A uafhængigt er fraværende eller hydrogen, eller m fortrinsvis er 1, og R7A, R12A, R13A og R14A uafhængigt er fraværende eller hydrogen.
7. Forbindelse ifølge krav 1, hvor R1A er H.
8. Forbindelse ifølge krav 1, hvor R1A er en eventuelt substitueret acyl.
9. Forbindelse ifølge krav 8, hvor den eventuelt substituerede acyl er -C(=O)R39A, hvor R39A er valgt fra gruppen bestående af en eventuelt substitueret Ci-12-alkyl, en eventuelt substitueret C2-i2-alkenyl, en eventuelt substitueret C2-12-alkynyl, en eventuelt substitueret C3-8-cycloalkyl, en eventuelt substitueret Cs-8-cycloalkenyl, en eventuelt substitueret C6-io-aryl, en eventuelt substitueret heteroaryl, en eventuelt substitueret heterocyclyl, en eventuelt
substitueret aryl(Ci-6-alkyl), en eventuelt substitueret heteroaryl(Ci-6-alkyl) og en eventuelt substitueret heterocyclyl (Ci-6-alkyl) , R39A fortrinsvis er substitueret eller ikke-substitueret Ci-12-alkyl.
10. Forbindelse ifølge krav 9, hvor R39A er en ikke-substitueret Ci-12-alkyl.
11. Forbindelse ifølge krav 1, hvor R1A er en eventuelt substitueret O-bundet aminosyre, eller R1A er
hvor r4oa er valgt fra gruppen bestående af hydrogen, en eventuelt substitueret Ci-6-alkyl, en eventuelt substitueret Ci-6-halogenalkyl, en eventuelt substitueret C3-6-cycloalkyl, en eventuelt substitueret C6-aryl, en eventuelt substitueret C10-aryl og en eventuelt substitueret aryl (Ci-6-alkyl) , og R41A er hydrogen eller en eventuelt substitueret Ci-4-alkyl, eller R40A og R41A er taget sammen for at danne en eventuelt substitueret C3-6-cycloalkyl, R40A fortrinsvis er en eventuelt substitueret Ci-6-alkyl, r4oa fortrinsvis er methyl, R41A fortrinsvis er hydrogen.
12. Forbindelse ifølge krav 1, hvor B1A er
eller
13. Forbindelse ifølge krav 1, hvor B1A er
eller
14. Forbindelse ifølge et hvilket som helst af kravene 1-13, hvor R2A er en halogen-substitueret Ci-6-alkyl eller en sulfenyl-substitueret Ci-6-alkyl.
15. Forbindelse ifølge et hvilket som helst af kravene 1-13, hvor R2A er en halogen-substitueret Ci-6-alkyl.
16. Forbindelse ifølge et hvilket som helst af kravene 1-15, hvor R3A er OH.
17. Forbindelse ifølge et hvilket som helst af kravene 1-15, hvor R3A er -OC(=O)R"A, R3A fortrinsvis er -OC(=O)R"A, hvor R"A er en eventuelt substitueret Ci-8-alkyl.
18. Forbindelse ifølge krav 17, hvor R"A er en ikke-substitueret Ci-s-alkyl.
19. Forbindelse ifølge et hvilket som helst af kravene 1-15, hvor R3A er en eventuelt substitueret O-bundet aminosyre, den O-bundne aminosyre fortrinsvis er valgt fra gruppen bestående af alanin, asparagin, aspartat, cystein, glutamat, glutamin, glycin, prolin, serin, tyrosin, arginin, histidin, isoleucin, leucin, lysin, methionin, phenylalanin, threonin, tryptophan, valin, ornithin, hypusin, 2-aminoisosmørsyre, dehydroalanin, gamma-aminosmørsyre, citrullin, beta-alanin, alfa-ethylglycin, alfa-propylglycin og norleucin; eller R3A er
hvor R42A er valgt fra gruppen bestående af hydrogen, en eventuelt substitueret Ci-6-alkyl, en eventuelt substitueret Ci-6-halogenalkyl, en eventuelt substitueret C3-6-cycloalkyl, en eventuelt substitueret C6~aryl, en eventuelt substitueret Cio-aryl og en eventuelt substitueret aryl (Ci-6-alkyl) , og R43A er hydrogen eller en eventuelt substitueret Ci-4-alkyl, eller R42A og R43A er taget sammen for at danne en eventuelt substitueret C3-6-cycloalkyl, R42A fortrinsvis er en eventuelt substitueret Ci-6-alkyl, R42A fortrinsvis er methyl, R43A fortrinsvis er hydrogen.
20. Forbindelse ifølge krav 1, hvor forbindelsen med formlen (I) er valgt fra gruppen bestående af:
eller et farmaceutisk acceptabelt salt af en hvilket som helst af de foregående forbindelser.
21. Forbindelse ifølge krav 1, hvor forbindelsen med formlen (I) er valgt fra gruppen bestående af:
eller et farmaceutisk acceptabelt salt af en hvilket som helst af de foregående forbindelser.
22. Forbindelse ifølge krav 1, hvor forbindelsen med formlen (I) er valgt fra gruppen bestående af:
eller et farmaceutisk acceptabelt salt af en hvilket som helst af de foregående forbindelser.
23. Forbindelse ifølge krav 1, hvor forbindelsen med formlen (I) er valgt fra gruppen bestående af:
eller et farmaceutisk acceptabelt salt af en hvilket som helst af de foregående forbindelser.
24. Forbindelse ifølge krav 1, hvor forbindelsen med formlen (I) er
eller et farmaceutisk acceptabelt salt deraf.
25. Forbindelse ifølge krav 1, hvor forbindelsen med formlen (I) er
eller et farmaceutisk acceptabelt salt deraf.
26. Forbindelse ifølge krav 1, hvor forbindelsen med formlen (I) er
eller et farmaceutisk acceptabelt salt deraf.
27. Forbindelse ifølge krav 1, hvor forbindelsen med formlen (I) er
eller et farmaceutisk acceptabelt salt deraf.
28. Forbindelse ifølge krav 1, hvor forbindelsen med formlen (I) er
eller et farmaceutisk acceptabelt salt deraf.
29. Forbindelse ifølge et hvilket som helst af kravene 24-28, hvor B1A er cytosin.
30. Forbindelse ifølge et hvilket som helst af kravene 24-28, hvor R1A er hydrogen, et monophosphat, et diphosphat eller et triphosphat.
31. Forbindelse ifølge krav 1, hvor forbindelsen med formlen (I) er
eller et farmaceutisk acceptabelt salt deraf.
32. Forbindelse ifølge krav 1, hvor forbindelsen med formlen (I) er
eller et farmaceutisk acceptabelt salt deraf.
33. Forbindelse ifølge krav 1, hvor forbindelsen med formlen (I) er
eller et farmaceutisk acceptabelt salt deraf.
34. Forbindelse ifølge krav 1, hvor forbindelsen med formlen (I) er
eller et farmaceutisk acceptabelt salt deraf.
35. Forbindelse ifølge krav 1, hvor forbindelsen med formlen (I) er
eller et farmaceutisk acceptabelt salt deraf.
36. Forbindelse ifølge krav 1, hvor forbindelsen med formlen (I) er
eller et farmaceutisk acceptabelt salt deraf.
37. Forbindelse ifølge krav 1, hvor forbindelsen med formlen (I) er
eller et farmaceutisk acceptabelt salt deraf.
38. Forbindelse ifølge krav 1, hvor forbindelsen med formlen (I) er
eller et farmaceutisk acceptabelt salt deraf.
39. Forbindelse ifølge krav 1, hvor forbindelsen med formlen (I) er
eller et farmaceutisk acceptabelt salt deraf.
40. Forbindelse ifølge krav 1, hvor forbindelsen med formlen (I) er
eller et farmaceutisk acceptabelt salt deraf.
41. Forbindelse ifølge krav 1, hvor forbindelsen med formlen (I) er
eller et farmaceutisk acceptabelt salt deraf.
42. Forbindelse ifølge krav 1, hvor forbindelsen med formlen (I) er
eller et farmaceutisk acceptabelt salt deraf.
43. Forbindelse, der har en struktur valgt fra gruppen bestående af:
eller et farmaceutisk acceptabelt salt af en hvilket som helst af de foregående forbindelser.
44. Farmaceutisk sammensætning, der omfatter en effektiv mængde af en forbindelse ifølge et hvilket som helst af kravene 1-43 eller et farmaceutisk acceptabelt salt deraf, og en farmaceutisk acceptabelt bærer, diluent, excipiens eller kombination deraf.
45. Forbindelse ifølge et hvilket som helst af kravene 1-43 til anvendelse til forbedring eller behandling af en viral infektion med paramyxovirus, fortrinsvis en pneumoviral infektion, fortrinsvis en human respiratorisk syncytialvirusinfektion.
46. Forbindelse ifølge et hvilket som helst af kravene 1-43 til anvendelse til hæmning af replikationen af en paramyxovirus, fortrinsvis en pneumoviral infektion, fortrinsvis en human respiratorisk syncytialvirusinfektion.
47. Forbindelse til anvendelse ifølge krav 45 eller 46 i kombination med et eller flere anti-RSV-midler.
48. Forbindelse til anvendelse ifølge krav 47, hvor det ene eller flere RSV-midler er valgt fra gruppen bestående af ribavirin, palivizumab, RSV-IGIV, ALN-RSV01, BMS-433771, RFI-641, RSV604, MDT-637, BTA9881, TMC-353121, MBX-300, YM-53403 og en RSV-F-partikelvaccine.
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