HRP20180371T1 - Novi derivati piridina - Google Patents

Novi derivati piridina Download PDF

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HRP20180371T1
HRP20180371T1 HRP20180371TT HRP20180371T HRP20180371T1 HR P20180371 T1 HRP20180371 T1 HR P20180371T1 HR P20180371T T HRP20180371T T HR P20180371TT HR P20180371 T HRP20180371 T HR P20180371T HR P20180371 T1 HRP20180371 T1 HR P20180371T1
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cyclopropyl
pyridin
oxadiazole
butyl
tert
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HRP20180371TT
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Olivier GAVELLE
Uwe Grether
Atsushi KIMBARA
Matthias Nettekoven
Stephan Roever
Mark Rogers-Evans
Didier Rombach
Tanja Schulz-Gasch
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F. Hoffmann - La Roche Ag
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Publication of HRP20180371T1 publication Critical patent/HRP20180371T1/hr

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Claims (21)

1. Spoj, naznačen time, da ima formulu (I) [image] u kojoj A je A1, A2, A3, A4, A5, A6, A7 ili A8 [image] R1 je vodik ili halogen; R2 je halogen, cikloalkil, haloazetidinil, 6-oksa-1-aza-spiro[3.3]heptil ili alkilsulfonil; R3 je -OR8, pirolidinil, halopirolidinil, hidroksipirolidinil, morfolinil, cikloalkilsulfonil, alkoksiazetidinil, 2-oksa-6-aza-spiro[3.3]heptil ili 2-oksa-7-azaspiro[3.4]heptil; R4 je vodik, alkil, hidroksialkil, alkoksialkil, haloalkil, cikloalkil, hidroksicikloalkil, alkilcikloalkil, aminokarbonilcikloalkil, fenil, fenilalkil, alkiloksetanil, azetidinil ili aminooksetanil; R5 je vodik, alkil ili alkiloksadiazolil; ili R4 i R5, zajedno s ugljikovim atomom s kojim su spojeni tvore cikloalkil; R6 je alkil; R7 je alkil; i R8 je haloalkil, alkoksialkil, cikloalkilalkil, haloalkil, halofenil, oksetanil, oksetanilalkil, alkiloksetanilalkil, tetrahidrofuranil, tetrahidrofuranilalkil, alkilsulfonilfenil, alkilpirolidinil, alkilpirolidinilalkil, azetidinil, morfolinilalkil, tetrahidropiranil, pirolidinilalkil, piperidinil, piperidinilalkil, alkilpiperidinilalkil, alkilpiperidinil, dialkilaminoalkil, piridinilalkil, halooksetanilalkil, dialkiloksazolilalkil, alkiloksazolilalkil halopiridinilalkil ili morfolinil; ili njegova farmaceutski prihvatljiva sol.
2. Spoj prema patentnom zahtjevu 1, naznačen time, da A je A1 ili A2.
3. Spoj prema patentnom zahtjevu 1 ili 2, naznačen time, da R1 je vodik ili klor.
4. Spoj prema bilo kojem od patentnih zahtjeva 1 do 3, naznačen time, da R1 je vodik.
5. Spoj prema bilo kojem od patentnih zahtjeva 1 do 4, naznačen time, da R2 je cikloalkil.
6. Spoj prema bilo kojem od patentnih zahtjeva 1 do 5, naznačen time, da R2 je ciklopropil.
7. Spoj prema bilo kojem od patentnih zahtjeva 1 do 6, naznačen time, da R3 je -OR8.
8. Spoj prema bilo kojem od patentnih zahtjeva 1 do 7, naznačen time, da R4 je alkil.
9. Spoj prema bilo kojem od patentnih zahtjeva 1 do 8, naznačen time, da R4 je butil.
10. Spoj prema bilo kojem od patentnih zahtjeva 1 do 9, naznačen time, da R5 je vodik, etil ili metiloksadiazolil, ili R4 i R5 zajedno s ugljikovim atomom s kojim su spojeni, tvore cikloheksil.
11. Spoj prema bilo kojem od patentnih zahtjeva 1 do 10, naznačen time, da R6 je metil.
12. Spoj prema bilo kojem od patentnih zahtjeva 1 do 11, naznačen time, da R7 je metil ili izopropil.
13. Spoj prema bilo kojem od patentnih zahtjeva 1 do 12, naznačen time, da R8 je haloalkil, alkoksialkil, halofenil, alkiloksetanilalkil, oksetanilalkil, tetrahidrofuranil, tetrahidrofuranilalkil, tetrahidropiranil, halopiridinilalkil ili morfolinil.
14. Spoj prema bilo kojem od patentnih zahtjeva 1 do 13, naznačen time, da R8 je trifluorometil, etoksietil, metoksibutil, fluorofenil, oksetanilmetil, metiloksetanilmetil, tetrahidrofuranil, tetrahidrofuranilmetil, tetrahidropiranil, difluoroetil, fluoropiridinilmetil ili morfolinil.
15. Spoj prema bilo kojem od patentnih zahtjeva 1 do 14, naznačen time, da je odabran iz skupine koju čine: 5-[5-ciklopropil-4-(ciklopropilmetoksi)piridin-2-il]-3-metil-1,2,4-oksadiazol; 5-[5-ciklopropil-4-(ciklopropilmetoksi)piridin-2-il]-3-fenil-1,2,4-oksadiazol; 3-ciklopropil-5-[5-ciklopropil-4-(ciklopropilmetoksi)piridin-2-il]-1,2,4-oksadiazol; 3-ciklopentil-5-[5-ciklopropil-4-(ciclopropilmetoksi)piridin-2-il]-1,2,4-oksadiazol; 3-benzil-5-[5-ciklopropil-4-(ciklopropilmetoksi)piridin-2-il]-1,2,4-oksadiazol; 3-terc-butil-5-[5-ciklopropil-4-(ciklopropilmetoksi)piridin-2-il]-1,2,4-oksadiazol; 3-ciklopropil-5-[5-ciklopropil-4-(2,2,2-trifluoroetoksi)piridin-2-il]-1,2,4-oksadiazol; 5-[5-ciklopropil-4-(2,2,2-trifluoroetoksi)piridin-2-il]-3-(trifluorometil)-1,2,4-oksadiazol; 5-ciklopropil-3-[5-ciklopropil-4-(ciklopropilmetoksi)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(ciklopropilmetoksi)piridin-2-il]-1,2,4-oksadiazol; 2-[5-ciklopropil-4-(ciklopropilmetoksi)piridin-2-il]-4,4-dietil-5H-1,3-oksazol; 3-[5-ciklopropil-4-(ciklopropilmetoksi)piridin-2-il]-5-(metoksimetil)-1,2,4-oksadiazol; 3-[5-ciklopropil-4-(ciklopropilmetoksi)piridin-2-il]-5-etil-1,2,4-oksadiazol; 3-[5-ciklopropil-4-(ciklopropilmetoksi)piridin-2-il]-5-propan-2-il-1,2,4-oksadiazol; 3-ciklopropil-5-[5-(3,3-difluoroazetidin-1-il)-4-(2,2,2-trifluoroetoksi)piridin-2-il]-1,2,4-oksadiazol; 5-[5-(3,3-difluoroazetidin-1-il)-4-(2,2,2-trifluoroetoksi)piridin-2-il]-3-metil-1,2,4-oksadiazol; 3-terc-butil-5-[5-(3,3-difluoroazetidin-1-il)-4-(2,2,2-trifluoroetoksi)piridin-2-il]-1,2,4-oksadiazol; [3-[5-ciklopropil-4-(ciklopropilmetoksi)piridin-2-il]-1,2,4-oksadiazol-5-il]metanol; 3-[5-ciklopropil-4-(ciklopropilmetoksi)piridin-2-il]-5-(trifluorometil)-1,2,4-oksadiazol; (4S)-4-terc-butil-2-[5-ciklopropil-4-(ciklopropilmetoksi)piridin-2-il]-4,5-dihidro-1,3-oksazol; 2-[5-ciklopropil-4-(ciklopropilmetoksi)piridin-2-il]-4-etil-4,5-dihidro-1,3-oksazol; 2-[5-ciklopropil-4-(ciklopropilmetoksi)piridin-2-il]-3-oksa-1-azaspiro[4.5]dec-1-en; 1-[3-[5-ciklopropil-4-(ciklopropilmetoksi)piridin-2-il]-1,2,4-oksadiazol-5-il]ciklopropan-1-ol; 3-[5-ciklopropil-4-(ciklopropilmetoksi)piridin-2-il]-5-(1-metilciklopropil)-1,2,4-oksadiazol; 1-[3-[5-ciklopropil-4-(ciklopropilmetoksi)piridin-2-il]-1,2,4-oksadiazol-5-il]ciklopropan-1-karboksamid; 2-[3-[5-ciklopropil-4-(ciklopropilmetoksi)piridin-2-il]-1,2,4-oksadiazol-5-il]propan-2-ol; 2-[5-ciklopropil-4-(2,2,2-trifluoroetoksi)piridin-2-il]-4,4-dietil-5H-1,3-oksazol; 3-[5-ciklopropil-4-(ciklopropilmetoksi)piridin-2-il]-5-(3-metiloksetan-3-il)-1,2,4-oksadiazol; 5-(azetidin-3-il)-3-[5-ciklopropil-4-(ciklopropilmetoksi)piridin-2-il]-1,2,4-oksadiazol; 2-[5-(3,3-difluoroazetidin-1-il)-4-(2,2,2-trifluoroetoksi)piridin-2-il]-4,4-dietil-5H-1,3-oksazol; 2-[5-ciklopropil-4-(2,2,2-trifluoroetoksi)piridin-2-il]-3-oksa-1-azaspiro[4.5]dec-1-en; 5-terc-butil-3-[4-(ciklopropilmetoksi)-5-(3,3-difluoroazetidin-1-il)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(2,2,2-trifluoroetoksi)piridin-2-il]-1,2,4-oksadiazol; 3-[5-ciklopropil-4-(2,2,2-trifluoroetoksi)piridin-2-il]-5-(1-metilciklopropil)-1,2,4-oksadiazol; 1-[6-(5-terc-butil-1,2,4-oksadiazol-3-il)-4-(ciklopropilmetoksi)piridin-3-il]-6-oksa-1-azaspiro[3.3]heptan; 3-[5-ciklopropil-4-(2,2,2-trifluoroetoksi)piridin-2-il]-5-propan-2-il-1,2,4-oksadiazol; 1-[3-[5-ciklopropil-4-(2,2,2-trifluoroetoksi)piridin-2-il]-1,2,4-oksadiazol-5-il]ciklopropan-1-ol; 3-[5-ciklopropil-4-(2,2,2-trifluoroetoksi)piridin-2-il]-5-(3-metiloksetan-3-il)-1,2,4-oksadiazol; 3-[5-ciklopropil-4-(2,2,2-trifluoroetoksi)piridin-2-il]-1,2,4-oksadiazol; 3-terc-butil-5-[5-ciklopropil-4-(2,2,2-trifluoroetoksi)piridin-2-il]-1,2,4-oksadiazol; 2-[5-ciklopropil-4-(2,2,2-trifluoroetoksi)piridin-2-il]-5,5-dimetil-4H-1,3-oksazol; 5-[5-ciklopropil-4-(2,2,2-trifluoroetoksi)piridin-2-il]-3-propan-2-il-1,2,4-oksadiazol; 5-terc-butil-3-[4-(ciklopropilmetoksi)-5-metilsulfonilpiridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-(3,3-difluoroazetidin-1il)-4-(2,2,2-trifluoroetoksi)piridin-2-il]-1,2,4-oksadiazol; 3-[5-(3,3-difluoroazetidin-1-il)-4-(2,2,2-trifluoroetoksi)piridin-2-il]-5-propan-2-il-1,2,4-oksadiazol; 1-[3-[5-(3,3-difluoroazetidin-1-il)-4-(2,2,2-trifluoroetoksi)piridin-2-il]-1,2,4-oksadiazol-5-il]ciklopropan-1-ol; 3-[5-(3,3-difluoroazetidin-1-il)-4-(2,2,2-trifluoroetoksi)piridin-2-il]-5-(3-metiloksetan-3-il)-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-[(2S)-1,1,1-trifluoropropan-2-il]oksipiridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-[(2R)-1,1,1-trifluoropropan-2-il]oksipiridin-2-il]-1,2,4-oksadiazol; 3-[5-(3,3-difluoroazetidin-1-il)-4-(2,2,2-trifluoroetoksi)piridin-2-il]-5-(1-metilciklopropil)-1,2,4-oksadiazol; 3-terc-butil-5-[5-ciklopropil-4-[(2R)-1,1,1-trifluoropropan-2-il]oksipiridin-2-il]-1,2,4-oksadiazol; 3-terc-butil-5-[5-ciklopropil-4-[(2S)-1,1,1-trifluoropropan-2-il]oksipiridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(oksetan-3-iloksi)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-[(3-metiloksetan-3-il)metoksi]piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(oksolan-2-ilmetoksi)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-[[(2S)-1-metilpirolidin-2-il]metoksi]piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(oksetan-2-ilmetoksi)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(1-metilpirolidin-3-il)oksipiridin-2-il]-1,2,4-oksadiazol; 3-[3-[5-ciklopropil-4-(ciklopropilmetoksi)piridin-2-il]-1,2,4-oksadiazol-5-il]oksetan-3-amin; 5-terc-butil-3-[5-ciklopropil-4-(4-fluorofenoksi)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(oksolan-3-iloksi)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(oksan-4-iloksi)piridin-2-il]-1,2,4-oksadiazol; 2-(5-terc-butil-1H-imidazol-2-il)-5-(3,3-difluoroazetidin-1-il)-4-(2,2,2-trifluoroetoksi)piridin; 5-terc-butil-2-[5-ciklopropil-4-(ciklopropilmetoksi)piridin-2-il]-1,3-oksazol; 2-[5-ciklopropil-4-(2,2,2-trifluoroetoksi)piridin-2-il]-4-metil-4-propan-2-il-1H-imidazol-5-on; 5-terc-butil-3-[5-metilsulfonil-4-(2,2,2-trifluoroetoksi)piridin-2-il]-1,2,4-oksadiazol; 2-[5-ciklopropil-4-(2,2,2-trifluoroetoksi)piridin-2-il]-4-etil-4-metil-1H-imidazol-5-on; 2-[5-ciklopropil-4-(2,2,2-trifluoroetoksi)piridin-2-il]-4-metil-4-(2-metilpropil)-1H-imidazol-5-on; 2-[5-bromo-4-(2,2,2-trifluoroetoksi)piridin-2-il]-4-metil-4-propan-2-il-1H-imidazol-5-on; 5-terc-butil-3-[5-kloro-4-(2,2,2-trifluoroetoksi)piridin-2-il]-1,2,4-oksadiazol; 3-[5-kloro-4-(2,2,2-trifluoroetoksi)piridin-2-il]-5-ciklopropil-1,2,4-oksadiazol; 5-ciklopropil-3-[5-ciklopropil-4-(2,2,2-trifluoroetoksi)piridin-2-il]-1,2,4-oksadiazol; 1-[2-(5-terc-butil-1,2,4-oksadiazol-3-il)-5-ciklopropilpiridin-4-il]pirolidin-3-ol; 5-terc-butil-3-[5-ciklopropil-4-(3,3,4,4-tetrafluoropirolidin-1-il)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(4-metilsulfonilfenoksi)piridin-2-il]-1,2,4-oksadiazol; 7-[2-(5-terc-butil-1,2,4-oksadiazol-3-il)-5-ciklopropilpiridin-4-il]-2-oksa-7-azaspiro[3.4]oktan; 5-terc-butil-3-[5-ciklopropil-4-(3,3-difluoropirolidin-1-il)piridin-2-il]-1,2,4-oksadiazol; 4-[2-(5-terc-butil-1,2,4-oksadiazol-3-il)-5-ciklopropilpiridin-4-il]morfolin; 5-terc-butil-3-(5-ciklopropil-4-pirolidin-1-ilpiridin-2-il)-1,2,4-oksadiazol; 5-terc-butil-3-(5-ciklopropil-4-ciklopropilsulfonilpiridin-2-il)-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(3-metoksiazetidin-1-il)piridin-2-il]-1,2,4-oksadiazol; 6-[2-(5-terc-butil-1,2,4-oksadiazol-3-il)-5-ciklopropilpiridin-4-il]-2-oksa-6-azaspiro[3.3]heptan; 5-terc-butil-3-[5-ciklopropil-4-(2-etoksietoksi)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(1-metoksibutan-2-iloksi)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-[2-[(2-metilpropan-2-il)oksi]etoksi]piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-[1-[(2-metilpropan-2-il)oksi]propan-2-iloksi]piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(1-metoksipropan-2-iloksi)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(oksan-3-iloksi)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(3-metoksibutoksi)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(oksetan-3-ilmetoksi)piridin-2-il]-1,2,4-oksadiazol; 5-ciklopropil-3-[5-ciklopropil-4-[(2S)-1,1,1-trifluoropropan-2-il]oksipiridin-2-il]-1,2,4oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(1-etilpirolidin-3-il)oksipiridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(1-propan-2-ilpirolidin-3-il)oksipiridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(2-pirolidin-1-iletoksi)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(2-piperidin-1-iletoksi)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(1-piperidin-1-ilpropan-2-iloksi)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-[(1-metilpiperidin-2-il)metoksi]piridin-2-il]-1,2,4-oksadiazol; 2-terc-butil-5-[5-ciklopropil-4-(oksan-4-iloksi)piridin-2-il]-1,3,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(1-metilpiperidin-3-il)oksipiridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(1-etilpiperidin-3-il)oksipiridin-2-il]-1,2,4-oksadiazol; 2-[2-(5-terc-butil-1,2,4-oksadiazol-3-il)-5-ciklopropilpiridin-4-il]oksi-N,N-dietilpropan-1-amin; 3-[[2-(5-terc-butil-1,2,4-oksadiazol-3-il)-5-ciklopropilpiridin-4-il]oksimetil]morfolin; 4-[2-[2-(5-terc-butil-1,2,4-oksadiazol-3-il)-5-ciklopropilpiridin-4-il]oksietil]morfolin; 5-terc-butil-3-(5-ciklopropil-4-piperidin-3-iloksipiridin-2-il)-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-[(3-fluorooksetan-3-il)metoksi]piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-[(2,5-dimetil-1,3-oksazol-4-il)metoksi]piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-[(5-metil-1,2-oksazol-3-il)metoksi]piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(3-metilsulfonilfenoksi)piridin-2-il]-1,2,4-oksadiazol; 3-[2-[5-ciklopropil-4-(2,2,2-trifluoroetoksi)piridin-2-il]-4-metil-5H-1,3-oksazol-4-il]-5-metil-1,2,4-oksadiazol; 2-terc-butil-5-[5-ciklopropil-4-(2,2,2-trifluoroetoksi)piridin-2-il]-1,3,4-oksadiazol; 5-terc-butil-3-[6-kloro-5-ciklopropil-4-(oksan-4-iloksi)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(2,2-difluoroetoksi)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(2-fluoroetoksi)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(piridin-2-ilmetoksi)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-[(5-fluoropiridin-2-il)metoksi]piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(piridin-3-ilmetoksi)piridin-2-il]-1,2,4-oksadiazol; 2-terc-butil-5-[5-ciklopropil-4-[(2S)-1,1,1-trifluoropropan-2-il]oksipiridin-2-il]-1,3,4-oksadiazol; 3-terc-butil-5-(5-ciklopropil-4-(tetrahidro-2H-piran-4-iloksi)piridin-2-il)-1,2,4-oksadiazol; 3-terc-butil-5-[5-ciklopropil-4-[[(2S)-1-metilpirolidin-2-il]metoksi]piridin-2-il]-1,2,4-oksadiazol; i 3-terc-butil-5-(5-ciklopropil-4-(2,2-difluoroetoksi)piridin-2-il)-1,2,4-oksadiazol.
16. Spoj prema bilo kojem od patentnih zahtjeva 1 do 15, naznačen time, da je odabran iz skupine koju čine: 5-terc-butil-3-[5-ciklopropil-4-(2,2,2-trifluoroetoksi)piridin-2-il]-1,2,4-oksadiazol; 3-terc-butil-5-[5-ciklopropil-4-(2,2,2-trifluoroetoksi)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-[(3-metiloksetan-3-il)metoksi]piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(oksolan-2-ilmetoksi)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(4-fluorofenoksi)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(oksolan-3-iloksi)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(oksan-4-iloksi)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(2-etoksietoksi)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(3-metoksibutoksi)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-(oksetan-3-ilmetoksi)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-ciklopropil-4-[(5-fluoropiridin-2-il)metoksi]piridin-2-il]-1,2,4-oksadiazol; 3-terc-butil-5-(5-ciklopropil-4-(tetrahidro-2H-piran-4-iloksi)piridin-2-il)-1,2,4-oksadiazol; i 3-terc-butil-5-(5-ciklopropil-4-(2,2-difluoroetoksi)piridin-2-il)-1,2,4-oksadiazol.
17. Spoj, naznačen time, da je odabran iz skupine koju čine: 5-terc-butil-3-[5-ciklopropil-4-[(4-fluorofenil)metoksi]piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-(3-fluorooksetan-3-il)-4-(oksan-4-iloksi)piridin-2-il]-1,2,4-oksadiazol; 5-terc-butil-3-[5-(3-fluorooksetan-3-il)-4-(4-fluorofenoksi)piridin-2-il]-1,2,4-oksadiazol; i 5-terc-butil-3-(6-kloro-5-ciklopropil-4-(4-fluorobenziloksi)piridin-2-il)-1,2,4-oksadiazol.
18. Postupak za proizvodnju spoja formule (I) prema bilo kojem od patentnih zahtjeva 1 do 16, naznačen time, da obuhvaća jedan od sljedećih koraka: (a) zagrijavanje spoja formule (A) [image] (b) zagrijavanje spoja formule (B) [image] (c) reakciju spoja formule (C) [image] u prisutnosti haloazetidina ili 6-oksa-1-aza-spiro[3.3]heptana, baze i paladijskog katalizatora; (d) reakciju spoja formule (D) [image] u prisutnosti trifluorometansulfonskog anhidrida i trifenilfosfin-oksida; (e) reakciju spoja formule (E1) ili (E2) [image] u prisutnosti HOR, haloazetidina, 6-oksa-1-aza-spiro[3.3]heptana ili HSO2R i baze; (f) zagrijavanje spoja formule (F) [image] u prisutnosti Burgessovog reagensa; (g) zagrijavanje spoja formule (G) [image] u prisutnosti metansulfonske kiseline; (h) zagrijavanje spoja formule (H) [image] (j) zagrijavanje spoja formule (J) [image] (k) reakciju spoja formule (K) [image] u prisutnosti heksakloroetana, baze i fosfina; (l) reakciju spoja formule (L) [image] u prisutnosti oksidacijskog sredstva; (m) zagrijavanje spoja formule (M) [image] u prisutnosti baze; (n) reakciju spoja formule (N) [image] u prisutnosti sredstva za kloriranje i DMF; ili (o) reakciju spoja formule (C) kao što je gore navedeno u prisutnosti HSR i baze, a zatim i oksidacijskog sredstva; pri čemu A, A1 i A2 te R1 do R4 su isti kao što su definirani u bilo kojem od patentnih zahtjeva 1 do 14 i pri čemu R predstavlja alkil.
19. Spoj prema bilo kojem od patentnih zahtjeva 1 do 17, naznačen time, da se upotrebljava kao terapeutski djelotvorna tvar.
20. Farmaceutski pripravak, naznačen time, da obuhvaća spoj prema bilo kojem od patentnih zahtjeva 1 do 17 i terapeutski inertni nosač.
21. Spoj prema bilo kojem od patentnih zahtjeva 1 do 17, naznačen time, da se upotrebljava u liječenju ili profilaksi boli, ateroskleroze, staračke makularne degeneracije, dijabetičke retinopatije, glaukoma, okluzije retinalne vene, retinopatije nedonoščadi, okularnog ishemijskog sindroma, geografske atrofije, šećerne bolesti (diabetes mellitus), upale, upalne bolesti crijeva, ishemijskih reperfuzijskih ozljeda, akutnog zatajenja jetre, jetrene fibroze, plućne fibroze, fibroze bubrega, sustavne fibroze, akutnog odbijanja alogenskog presatka, kronične alogenske nefropatije, dijabetičke nefropatije, glomerulonefropatije, kardiomiopatije, zatajenja srca, miokardijalne ishemije, miokardijalnog infarkta, sustavne skleroze, toplinskih ozljeda, opeklina, hipertrofičnih ožiljaka, keloida, pireksije gingive, jetrene ciroze ili tumora, u regulaciji koštane mase, amiotrofne lateralne skleroze, multiple skleroze, Alzheimerove bolesti, Parkinsonove bolesti, moždanog udara, prolaznog ishemijskog napadaja ili uveitisa.
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TW202417417A (zh) * 2017-04-06 2024-05-01 美商富曼西公司 殺真菌之噁二唑
TW201904943A (zh) * 2017-06-20 2019-02-01 瑞士商赫孚孟拉羅股份公司 新穎吡啶衍生物
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BR112015024272A2 (pt) 2017-07-18
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CR20150440A (es) 2015-10-08
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