HRP20110105T4 - Mek heterocikliäśki inhibitori - Google Patents

Mek heterocikliäśki inhibitori Download PDF

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Publication number
HRP20110105T4
HRP20110105T4 HRP20110105TT HRP20110105T HRP20110105T4 HR P20110105 T4 HRP20110105 T4 HR P20110105T4 HR P20110105T T HRP20110105T T HR P20110105TT HR P20110105 T HRP20110105 T HR P20110105T HR P20110105 T4 HRP20110105 T4 HR P20110105T4
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HR
Croatia
Prior art keywords
alkyl
halogen
heteroaryl
aryl
cycloalkyl
Prior art date
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HRP20110105TT
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English (en)
Inventor
Allison L. Marlow
Eli Wallace
Jeongbeob Seo
Joseph P. Lyssikatos
Hong Woon Yang
Jim Blake
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Array Biopharma, Inc.
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Publication date
Application filed by Array Biopharma, Inc. filed Critical Array Biopharma, Inc.
Publication of HRP20110105T1 publication Critical patent/HRP20110105T1/hr
Publication of HRP20110105T4 publication Critical patent/HRP20110105T4/hr

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    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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

Claims (29)

1. Spoj, naznačen time, što uključuje rastvarajuće enantiomere, dijastereomere i njegove farmaceutski prihvatljive soli, te ima formulu: [image] gdje X je N ili CR10; R1, R2, R8, R9 i R10 nezavisno su vodik, halogen, cijano, nitro, trifluorometil, difluorometil, fluorometil, fluorometoksi, difluorometoksi, triftuorometoksi, azido, -SR11, -OR3, -C(O)R3, -C(O)OR3, -NR4C (O)OR3, -OC(O)R3,-NR4SO2R6, -SO2NR3R4, -NR4C(O)R3, -C(O)NR3R4, -NR5C(O)NR3R4,-NR5C(NCN) NR3R4, -NR3R4; C1-C10 alkil, C2-C10 alkenil, C2-C10 alkinil, C3-C10 cikloalkil, C3-C10 cikloalkilalkil, -S(O)j (C1-C6 alkil), -S(O)j(CR4R5)m-aril, aril, arilalkil, heteroaril, heteroarilalkil, heterociklil, heterociklilalkil, -O(CR4R5)m-aril, -NR4(CR4R5)m-aril, -O(CR4R5)m-heteroaril, -NR4(CR4R5)m-heteroaril, -O(CR4R5)m-heterociklil ili -NR4(CR4R5)m- heterociklil, pri čemu je svaki od navedenih dijelova alkila, alkenila, alkinila, cikloalkila, arila, arilalkila, heteroarila, heteroarilalkila, heterociklila i heterociklilalkila opcionalno supstituiran sa jednom ili više nezavisnih grupa izabranih iz okso (pod uvjetom da nije supstituiran za aril ili heteroaril), halogen, cijano, nitro, trifluorometil, difluorometoksi, trifluorometoksi, azido, -NR4SO2R6, -SO2NR3R4; -C(O)R3, -C(O)OR3, -OC(O)R3, -NR4C(O)OR6, NR4C(O)R3, -C(O)NR3R4, -NR3R4, -NR5C(O)NR3R4, -NR5C (NCN)NR3R4, -OR3, aril, heteroaril, arilalkil, heteroarilalkil, heterociklil i heterociklilalkil, pri čemu navedeni aril, heteroaril, arilalkil, heteroarilalkil, heterociklil ili heterociklilalkil prstenovi mogu dodatno biti supstituirani sa jednom ili više grupa izabranih iz halogen, hidroksil, cijano, nitro, azido, fluorometil, difluorometil, trifluorometil, C1-C4 alkil, C2-C4 alkenil, C2-C4 alkinil, C3-C6 cikloalkil, C3-C6 heterocikloalkil, NR3R4 i OR3; R7 je hidrogen, trifluorometil, C1-C10 alkil, C2-C10 alkenil, C2-C10 alkinil, C3-C10 cikloalkil, C3-C10 cikloalkilalkil, aril, arilalkil, heteroaril, heteroarilalkil, heterociklil, ili heterociklilalkil, pri čemu je svaki od navedenih dijelova alkil, alkenil, alkinil, cikloalkil, aril, arilalkil, heteroaril, heteroarilalkil, heterociklil i heterociklilalkil opcionalno supstituiran sa jednom ili više nezavisnih grupa izabranih iz okso (pod uvjetom da nije supstituiran za aril ili heteroaril), halogen, cijano, nitro, trifluorometil, difluorometil, fluorometil, difluorometoksi, trifluorometoksi, azido, -NR11SO2R14, -SO2NR11R12, -C(O)R11, C(O)OR11, -OC(O)R11, -NR11C(O)OR14, -NR11C(O)R12, -C(O)NR11R12, -SR11, -S(O)R14, -SO2R14, -NR11R12, -NR11C(O) NR12R13,-NR11C(NCN)NR12R13, -OR11, C1-C10 alkil, C2-C10 alkenil, C2-C10 alkinil, C3-C10 cikloalkil, aril, heteroaril, arilalkil, heteroarilalkil, heterociklil i heterociklilalkil, pri čemu navedeni aril, heteroaril, arilalkil, heteroarilalkil, heterociklil ili heterociklilalkil prstenovi mogu dodatno biti supstituirani sa jednom ili više grupa izabranih iz halogen, hidroksil, cijano, nitro, azido, fluorometil, difluorometil, trifluorometil, C1-C4 alkil, C2-C4 alkenil, C2-C4 alkinil, C3-C6 cikloalkil, C3-C6 heterocikloalkil, NR3R4 i OR3; R3 je vodik, trifluorometil, C1-C10 alkil, C2-C10 alkenil, C2-C10 alkinil, C3-C10 cikloalkil, C3-C10 cikloalkilalkil, aril, arilalkil, heteroaril, heteroarilalkil, heterociklil, heterociklilalkil, fosfat ili ostatak aminokiseline, pri čemu je svaki od navedenih dijelova alkil, alkenil, alkinil, cikloalkil, aril, arilalkil, heteroaril, heteroarilalkil, heterociklil i heterociklilalkil opcionalno supstituiran sa jednom ili više nezavisnih grupa izabranih iz okso (pod uvjetom da nije supstituiran za aril ili heteroaril), halogen, cijano, nitro, trifluorometil, difluorometoksi, trifluorometoksi, azido, -NR11SO2R14, -SO2NR11R12, -C(O)R11, C(O)OR11, -OC(O)R11, -NR11C(O)OR14, - NR11C(O)R12, -C(O)NR11R12, -SR11, -S(O)R14, -SO2R14, -NR11R12, -NR11C (O)NR12R13, - NR11C(NCN)NR12R13, -OR11, aril, heteroaril, arilalkil, heteroarilalkil, heterociklil i heterociklilalkil, ili R3 i R4 zajedno s atomom za koji su pričvršćeni formiraju 4 do 10člani karbociklički, heteroarilni ili heterociklički prsten, pri čemu je svaki od navedenih karbociklički, heteroarilni ili heterociklički prstenova opcionalno supstituiran sa jednom ili više nezavisnih grupa izabranih iz halogen, cijano, nitro, trifluorometil, difluorometoksi, trifluorometoksi, azido, -NR11SO2R14, -SO2NR11R12, -C(O)R11, C(O)OR11, -OC(O)R11,-NR11C(O)OR14, -NR11C(O)R12, -C(O)NR11R12, -SR11, -S(O)R14, -SO2R14, -NR11R12, -NR11C(O)NR12R13, -NR11C(NCN)NR12R13, -OR11, aril, heteroaril, arilalkil, heteroarilalkil, heterociklil i heterociklilalkil; R4 i R5 nezavisno su vodik ili C1-C6 alkil, ili R4 i R5 zajedno s atomom za koji su pričvršćeni formiraju 4 do 10člani karbociklički, heteroarilni ili heterociklički prsten, pri čemu navedeni alkil ili svaki od navedenih karbociklički, heteroarilni ili heterociklički prstenova opcionalno supstituiran sa jednom ili više nezavisnih grupa izabranih iz halogen, cijano, nitro, trifluorometil, difluorometoksi, trifluorometoksi, azido, -NR11SO2R14, -SO2NR11R12, -C(O)R11, C(O)OR11, -OC(O)R11,-NR11C(O)OR14, -NR11C(O)R12, -C(O)NR11R12, -SR11, -S(O)R14, -SO2R14, -NR11R12, -NR11C(O)NR12R13, -NR11C(NCN)NR12R13, -OR11, aril, heteroaril, arilalkil, heteroarilalkil, heterociklil i heterociklilalkil; R6 je trifluorometil, C1-C10 alkil, C3-C10 cikloalkil, aril, arilalkil, heteroaril, heteroarilalkil, heterociklil ili heterociklilalkil, pri čemu je svaki od navedenih dijelova alkil, cikloalkil, aril, arilalkil, heteroaril, heteroarilalkil, heterociklil i heterociklilalkil opcionalno supstituiran sa jednom ili više nezavisnih grupa izabranih iz okso (pod uvjetom da nije supstituiran za aril ili heteroaril), halogen, cijano, nitro, trifluorometil, difluorometoksi, trifluorometoksi, azido, -NR11SO2R14, -SO2NR11R12, -C(O)R11, C(O)OR11, -OC(O)R11,-NR11C(O)OR14, -NR11C(O)R12, -C(O)NR11R12, -SR11, -S(O)R14, -SO2R14, -NR11R12, -NR11C(O)NR12R13, -NR11C(NCN)NR12R13, -OR11, aril, heteroaril, arilalkil, heteroarilalkil, heterociklil i heterociklilalkil; R11, R12 i R13 nezavisno su vodik, C1-C10 alkil, C2-C10 alkenil, aril i arilalkil, i R14 je C1-C10 alkil, C1-C10 alkenil, aril i arilalkil; ili bilo koja dva od R11, R12, R13 ili R14 zajedno s atomom za koji su pričvršćeni formiraju 4 do 10člani karbociklički, heteroarilni ili heterociklički prsten, pri čemu je svaki navedeni alkil, alkenil, aril, arilalkil karbociklički prstenovi, heteroarilni prstenovi ili heterociklički prstenovi opcionalno supstituiran sa jednom ili više nezavisnih grupa izabranih iz halogen, cijano, nitro, trifluorometil, difluorometoksi, trifluorometoksi, azido, aril, heteroaril, arilalkil, heteroarilalkil, heterociklil i heterociklilalkil; W je heterociklil, -C(O)OR3, -C(O)NR4OR3, -C(O)NR4SO2R3, -C(O) (C3-C10 cikloalkil), -C(O)(C1-C10 alkil), -C(O)(aril), -C(O)(heteroaril), -C(O)(heterociklil) ili CR3OR3, pri čemu je svaki navedeni heterociklil, -C(O)OR3, -C(O)NR4OR3, -C(O)NR4SO2R3, -C(O)(C3-C10 cikloalkil), -C(O)(C1-C10 alkil), -C(O)(aril), -C(O)(heteroaril), -C(O)(heterociklil) i CR3OR3 opcionalno supstituiran sa jednom ili više nezavisnih grupa izabranih iz halogen, cijano, nitro, azido, -NR3R4, -OR3, C1-C10 alkil, C2-C10 alkenil, C2-C10 alkinil, cikloalkil i heterocikloalkil, pri čemu je svaki navedeni C1-C10 alkil, C2-C10 alkenil, C2-C10 alkinil, cikloalkil i heterocikloalkil opcionalno supstituiran sa jednom ili više nezavisnih grupa izabranih iz -NR3R4 i -OR3; pod uvjetom da X je CH, W ne može biti C(O)aril ili C(O)heteroaril i dodatno pod uvjetom da X je CH, W je C(O)OR3 i R9 je F, R7 ne može biti H; m je 0, 1,2,3,4 ili 5; i j je 0, 1 ili 2.
2. Spoj prema zahtjevu 1, naznačen time, što X je CR10, a R10 je vodik, halogen, metil, fluorometil, difluorometil, fluorometil ili etil.
3. Spoj prema zahtjevu 2, naznačen time, što R9 je vodik, halogen, metil, fluorometil, difluorometil, trifluorometil ili etil.
4. Spoj prema zahtjevu 3, naznačen time, što W je izabran iz C(O)OR3, C(O)NR4OR3, i C(O)NR4S(O)2R3, pri čemu je svaki navedeni C(O)OR3, C(O)NR4OR3 ili C(O)NR4S(O)2R3 opcionalno supstituiran sa jednom ili više grupa izabranih iz halogen, hidroksil, cijano, nitro, azido, fluorometil, difluorometil, trifluorometil, metoksi, fluorometoksi, difluorometoksi, trifluorometoksi, amino, aminometil, dimetilamino, aminoetil, dietilamino, etoksi, C1-C4 alkil, C2-C4 alkenil, C2-C4 alkinil, C3-C6 cikloalkil i C3-C6 heterocikloalkil, pri čemu svaki navedeni C1-C4 alkil, C2-C4 alkenil, C2-C4 alkinil, cikloalkil ili heterocikloalkil može biti dodatno opcionalno supstituiran sa jednom ili više grupa izabranih iz NR3R4 i OR3.
5. Spoj prema zahtjevu 3, naznačen time, što W je izabran iz C(O)OR3 i C(O)NHOR3, pri čemu je svaki navedeni C(O)OR3 i C(O)NHOR3 opcionalno supstituiran sa jednom ili više grupa izabranih iz halogen, hidroksil, cijano, nitro, azido, fluorometil, difluorometil, trifluorometil, metoksi, fluorometoksi, difluorometoksi, trifluorometoksi, amino, aminometil, dimetilamino, aminoetil, dietilamino, etoksi, C1-C4 alkil, C2-C4 alkenil, C2-C4 alkinil, C3-C6 cikloalkil i C3-C6 heterocikloalkil, pri čemu svaki navedeni C1-C4 alkil, C2-C4 alkenil, C2-C4 alkinil, cikloalkil ili heterocikloalkil može biti dodatno opcionalno supstituiran sa jednom ili više grupa izabranih iz NR3R4 i OR3; i R3 je izabran iz vodika, C1-C4 alkil, C2-C4 alkenil, C2-C4 alkinil, C3-C6 cikloalkil i C3-C6 heterocikloalkil, pri čemu je svaki navedeni C1-C4 alkil, C2-C4 alkenil, C2-C4 alkinil, cikloalkil ili heterocikloalkil opcionalno supstituiran sa jednom ili više grupa izabranih iz NR11R12 i OR11.
6. Spoj prema zahtjevu 4, naznačen time, što R7 je C1-C4 alkil, C2-C4 alkenil ili C2-C4 alkinil, pri čemu navedeni C1-C4 alkil, C2-C4 alkenil i C2-C4 alkinil mogu biti opcionalno supstituirani sa jednom ili više grupa izabranih iz halogen, hidroksil, cijano, nitro, azido, fluorometil, difluorometil, trifluorometil, metoksi, fluorometoksi, difluorometoksi, amino, aminometil, dimetilamino, aminoetil, dietilamino, etoksi, cikloalkil, heterocikloalkil, aril ili heteroaril, pri čemu navedeni cikloalkil, heterocikloalkil, aril ili heteroaril prstenovi mogu biti opcionalno supstituirani sa jednom ili više grupa izabranih iz halogen, hidroksil, cijano, nitro, azido, fluorometil, difluorometil, trifluorometil, C1-C4 alkil, C2-C4 alkenil, C2-C4 alkinil, C3-C6 cikloalkil, C3-C6 heterocikloalkil, NR3R4 i OR3.
7. Spoj prema zahtjevu 5, naznačen time, što R7 je C1-C4 alkil, C2-C4 alkenil ili C2-C4 alkinil, pri čemu navedeni C1-C4 alkil, C2-C4 alkenil i C1-C4 alkinil mogu biti opcionalno supstituirani sa jednom ili više grupa izabranih iz halogen, hidroksil, cijano, nitro, azido, fluorometil, difluorometil, trifluorometil, metoksi, fluorometoksi, difluorometoksi, amino, aminometil, dimetilamino, aminoetil, dietilamino, etoksi, cikloalkil, heterocikloalkil, aril ili heteroaril, pri čemu navedeni cikloalkil, heterocikloalkil, aril ili heteroaril prstenovi mogu biti opcionalno supstituirani sa jednom ili više grupa izabranih iz halogen, hidroksil, cijano, nitro, azido, fluorometil, difluorometil, trifluorometil, C1-C4 alkil, C2-C4 alkenil, C2-C4 alkinil, C3-C6 cikloalkil, C3-C6 heterocikloalkil, NR3R4 i OR3.
8. Spoj prema zahtjevu 6 ili 7, naznačen time, što R8 je halogen, hidroksil, cijano, nitro, azido, metil, fluorometil, difluorometil, trifluorometil, metoksi, fluorometoksi, difluorometoksi, trifluorometoksi, amino, aminometil, dimetilamino, aminoetil, dietilamino, etil, etoksi ili SR11.
9. Spoj prema zahtjevu 8, naznačen time, što R1 i R2 nezavisno su vodik, halogen, metil, fluorometil, difluorometil, trifluorometil ili etil.
10. Spoj prema zahtjevu 6, naznačen time, što R1 je halogen ili metil, R2 je vodik i R8 je vodik, halogen, metil, fluorometil, difluorometil, trifluorometil ili SR11.
11. Spoj prema zahtjevu 7, naznačen time, što R1 je halogen ili metil, R2 je vodik i R8 je vodik, halogen, metil, fluorometil, difluorometil, trifluorometil ili SR11.
12. Spoj prema zahtjevu 10, naznačen time, što R1 je halogen, R8 je halogen, R9 je alkil ili halogen, i R2 je smješten u susjedni položaj do -NH- grupe gdje je R2 vodik.
13. Spoj prema zahtjevu 11, naznačen time, što R1 je halogen, R8 je halogen, R9 je alkil ili halogen, i R2 je smješten u susjedni položaj do -NH- grupe gdje je R2 vodik.
14. Spoj prema zahtjevu 1, naznačen time, što X je N.
15. Spoj prema zahtjevu 14, naznačen time, što R9 je vodik, halogen, metil, fluorometil, difluorometil, trifluorometil ili etil.
16. Spoj prema zahtjevu 15, naznačen time, što W je izabran iz C(O)OR3 i C(O)NHOR3, pri čemu je svaki navedeni C(O)OR3 i C(O)NHOR3 opcionalno supstituiran sa jednom ili više grupa izabranih iz halogen, hidroksil, cijano, nitro, azido, fluorometil, difluorometil, trifluorometil, metoksi, fluorometoksi, difluorometoksi, trifluorometoksi, amino, aminometil, dimetilamino, aminoetil, dietilamino, etoksi, C1-C4 alkil, C2-C4 alkenil, C2-C4 alkinil, C3-C6 cikloalkil i C3-C6 heterocikloalkil, pri čemu svaki navedeni C1-C4 alkil, C2-C4 alkenil, C2-C4 alkinil, cikloalkil ili heterocikloalkil može biti dodatno opcionalno supstituiran sa jednom ili više grupa izabranih iz NR3R4 i OR3; i R3 je izabran iz vodika, C1-C4 alkil, C2-C4 alkenil, C2-C4 alkinil, C3-C6 cikloalkil i C3-C6 heterocikloalkil, pri čemu je svaki navedeni C1-C4 alkil, C2-C4 alkenil, C2-C4 alkinil, cikloalkil ili heterocikloalkil opcionalno supstituiran sa jednom ili više grupa izabranih iz NR11R12 i OR11.
17. Spoj prema zahtjevu 16, naznačen time, što R7 je C1-C4 alkil, C2-C4 alkenil ili C2-C4 alkinil, pri čemu navedeni C1-C4 alkil, C2-C4 alkenil i C2-C4 alkinil mogu biti opcionalno supstituirani sa jednom ili više grupa izabranih iz halogen, hidroksil, cijano, nitro, azido, fluorometil, difluorometil, trifluorometil, metoksi, fluorometoksi, difluorometoksi, amino, aminometil, dimetilamino, aminoetil, dietilamino, etoksi, cikloalkil, heterocikloalkil, aril ili heteroaril, pri čemu navedeni cikloalkil, heterocikloalkil, aril ili heteroaril prstenovi mogu biti opcionalno supstituirani sa jednom ili više grupa izabranih iz halogen, hidroksil, cijano, nitro, azido, fluorometil, difluorometil, trifluorometil, C1-C4 alkil, C2-C4 alkenil, C2-C4 alkinil, C3-C6 cikloalkil, C3-C6 heterocikloalkil, NR3R4 i OR3.
18. Spoj prema zahtjevu 17, naznačen time, što R8 je halogen, hidroksil, cijano, nitro, azido, metil, fluorometil, difluorometil, trifluorometil, metoksi, fluorometoksi, difluorometoksi, trifluorometoksi, amino, aminometil, dimetilamino, aminoetil, dietilamino, etil, etoksi ili SR11.
19. Spoj prema zahtjevu 18, naznačen time, što R1 i R2 nezavisno su vodik, halogen, metil, fluorometil, difluorometil, trifluorometil ili etil.
20. Spoj prema zahtjevu 19, naznačen time, što R1 je halogen ili metil, R2 je vodik i R8 je vodik, halogen, metil, fluorometil, difluorometil, trifluorometil ili SR11.
21. Spoj prema zahtjevu 20, naznačen time, što R1 je halogen, R8 je halogen, R9 je alkil ili halogen, i R2 je smješten u susjedni položaj do -NH- grupe gdje je R2 vodik.
22. Sastav, naznačen time, što sadrži spoj bilo kojeg zahtjeva 1, 5, 7, 13 i 17 i farmaecutski prihvatljiv nosač.
23. Spoj prema bilo kojem zahtjevu 1, 5, 7, 13 i 17, naznačen time, što je za primjenu kao lijek.
24. Spoj prema bilo kojem zahtjevu 1, 5, 7, 13 i 17, naznačen time, što je za primjenu kao lijek za liječenje poremećaja hiperproliferacije ili upalnog stanja.
25. Primjena spoja prema bilo kojem zahtjevu 1, 5, 7, 13 i 17, naznačena time, što je za proizvodnju lijeka za liječenje poremećaja hiperproliferacije ili upalnog stanja.
26. Postupak za pripremu spoja formule 56 [image] naznačen time, što R1, R2 i R9 nezavisno su vodik, halogen, metil, fluorometil, difluorometil, trifluorometil ili etil; R4 je vodik ili C1-C6 alkil; R3 je alkil, alkenil, alkinil, cikloalkil, heterocikloalkil, aril ili heteroaril, pri čemu navedeni alkil, alkenil, alkinil, cikloalkil, heterocikloalkil, aril ili heteroaril mogu biti opcionalno supstituirani sa jednom ili više grupa izabranih iz halogen, hidroksil, cijano, nitro, amino, azido, fluorometil, difluorometil, trifluorometil, metoksi, fluorometoksi, difluorometoksi, amino, aminometil, dimetilamino, aminoetil, dietilamino, etoksi, cikloalkil, heterocikloalkil, aril ili heteroaril; R7 je alkil; i R8 je halogen, hidroksil, cijano, nitro, azido, metil, fluorometil, difluorometil, trifluorometil, metoksi, fluorometoksi, difluorometoksi, trifluorometoksi, amino, aminometil, dimetilamino, aminoetil, dietilamino, SR1, etil ili etoksi, navedeni postupak sadrži: (a) reakcija spoja formule 53 ili 58 [image] sa alkil halidom i bazom provođena pomoću reakcije sa anilin derivatom da osigura spoj formule 54 [image] i (b) (i) reakcija spoja formule 54 sa hidroksilaminom da osigura spoj formule 56 [image] ili (ii) reakcija spoja formule 54 sa vodenom bazom da osigura spoj formule 55 [image] provođena pomoću reakcije spoja formule 55 sa hidroksilaminom u prisustvu agensa spajanja da osigura spoj formule 56.
27. Postupak za pripremu spoja formule 57 [image] naznačen time, što R1, R2 i R9 nezavisno su vodik, halogen, metil, fluorometil, difluorometil, trifluorometil ili etil; R4 je vodik ili C1-C6 alkil; R3 je alkil, alkenil, alkinil, cikloalkil, heterocikloalkil, aril ili heteroaril, pri čemu navedeni alkil, alkenil, alkinil, cikloalkil, heterocikloalkil, aril ili heteroaril mogu biti opcionalno supstituirani sa jednom ili više grupa izabranih iz halogen, hidroksil, cijano, nitro, amino, azido, fluorometil, difluorometil, trifluorometil, metoksi, fluorometoksi, difluorometoksi, amino, aminometil, dimetilamino, aminoetil, dietilamino, etoksi, cikloalkil, heterocikloalkil, aril ili heteroaril; R7 je alkil; i R8 je halogen, hidroksil, cijano, nitro, azido, metil, fluorometil, difluorometil, trifluorometil, metoksi, fluorometoksi, difluorometoksi, trifluorometoksi, amino, aminometil, dimetilamino, aminoetil, dietilamino, SR1, etil ili etoksi, navedeni postupak sadrži: (a) reakcija spoja formule 53 ili 58 [image] sa alkil halidom i bazom provođena pomoću reakcije sa anilin derivatom da osigura spoj formule 54 [image] (b) reakcija spoja formule 54 sa vodenom bazom da osigura spoj formule 55 [image] i (c) reakcija spoja formule 55 sa aminom u prisustvu agensa spajanja da osigura spoj formule 57.
28. Postupak za pripremu spoja formule 87 [image] naznačen time, što X je CH ili N; R1, R2 i R9 nezavisno su vodik, halogen, metil, fluorometil, difluorometil, trifluorometil ili etil; R7 je alkil; i R8 je halogen, hidroksil, cijano, nitro, azido, metil, fluorometil, difluorometil, trifluorometil, metoksi, fluorometoksi, difluorometoksi, trifluorometoksi, amino, aminometil, dimetilamino, aminoetil, dietilamino, SR1, etil ili etoksi, navedeni postupak sadrži: (a) reakcija spoja formule 55 ili 62 [image] sa hidrazinom u prisustvu agensa spajanja da osigura spoj formule 86 [image] i (b) reakcija spoja formule 86 sa cijanogen bromidom da osigura spoj formule 87.
29. Spoj, naznačen time što je odabran iz 2-(4-Brom-2-fluoro-fenilamino)-1-metil-6-okso-1,6-dihidro-piridin-3-karboksilna kiselina ciklopropilmetoksi-amida, 2-(4-Brom-2-fluoro-fenilamino)-1-metil-6-okso-1,6-dihidro-piridin-3-karboksilna kiselina (2-hidroksi-etoksi)-amida, 2-(4-Brom-2-fluoro-fenilamino)-5-fluoro-1-metil-6-okso-1,6-dihidro-piridin-3- karboksilna kiselina (2-hidroksi-etoksi)-amida, 2-(4-Brom-2-fluoro-fenilamino)-1-etil-6-okso-1,6-dihidro-piridin-3- karboksilna kiselina (2- hidroksi-etoksi)-amida, 2-(2-Fluoro-4-metil-fenilamino)-1-metil-6-okso-1,6-dihidro-piridin-3- karboksilna kiselina (2- hidroksi-etoksi)-amida, 2-(2-Fluoro-4-iodo-fenilamino)-1-metil-6-okso-1,6-dihidro-piridin-3-karboksilna kiselina metoksi-amida.
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AU2004293019B2 (en) 2010-10-28
EP1682138A4 (en) 2007-01-24
UA84175C2 (ru) 2008-09-25
RU2351593C2 (ru) 2009-04-10
WO2005051300A3 (en) 2005-09-15
TW200526594A (en) 2005-08-16
ATE524443T1 (de) 2011-09-15
US7598383B2 (en) 2009-10-06
IL216454A0 (en) 2011-12-29
IL175716A (en) 2015-05-31
IL175716A0 (en) 2006-09-05
ES2355797T3 (es) 2011-03-31
CA2545660A1 (en) 2005-06-09
IL216455A0 (en) 2011-12-29
ES2389628T3 (es) 2012-10-29
CY1112941T1 (el) 2016-04-13
HRP20110105T1 (hr) 2011-03-31
CN102633716A (zh) 2012-08-15
EP2251327B1 (en) 2014-02-12
MXPA06005657A (es) 2006-08-23
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TWI404703B (zh) 2013-08-11
ES2355797T7 (es) 2013-04-01
US20090131435A1 (en) 2009-05-21
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JP4842137B2 (ja) 2011-12-21
SI1682138T1 (sl) 2011-04-29
US7576072B2 (en) 2009-08-18
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NO20062692L (no) 2006-08-14
ATE495155T1 (de) 2011-01-15
RU2006120948A (ru) 2008-01-10
PL1689233T3 (pl) 2012-11-30
CN1905873A (zh) 2007-01-31
PL2251327T3 (pl) 2014-07-31
US20050153942A1 (en) 2005-07-14
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WO2005051302A2 (en) 2005-06-09
HK1150607A1 (en) 2012-01-06
DK1682138T3 (da) 2011-04-18
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AU2011200276A1 (en) 2011-02-17
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