HRP20130181T1 - Derivati piridin-4-ila kao sredstva imunomodulacije - Google Patents

Derivati piridin-4-ila kao sredstva imunomodulacije Download PDF

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HRP20130181T1
HRP20130181T1 HRP20130181TT HRP20130181T HRP20130181T1 HR P20130181 T1 HRP20130181 T1 HR P20130181T1 HR P20130181T T HRP20130181T T HR P20130181TT HR P20130181 T HRP20130181 T HR P20130181T HR P20130181 T1 HRP20130181 T1 HR P20130181T1
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methyl
hydroxy
pyridin
oxadiazol
phenoxy
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Martin Bolli
David Lehmann
Boris Mathys
Claus Mueller
Oliver Nayler
Beat Steiner
Jörg Velker
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Actelion Pharmaceuticals Ltd.
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Claims (22)

1. Spoj, naznačen time, da ima formulu (I), [image] formula (I) gdje A predstavlja *-CONH-CH2-, *-CO-CH=CH-, *-CO-CH2CH2-, [image] gdje zvjezdice označavaju vezu koja je spojena na piridin-skupinu formule (I); R1 predstavlja C1-4-alkil ili kloro; R2 predstavlja C1-5-alkil, C1-4-alkoksi ili C3-6-cikloalkil; R3 predstavlja vodik, C1-4-alkil, C1-4-alkoksi ili halogen; R4 predstavlja vodik, C1-4-alkil, C1-4-alkoksi, halogen, trifluorometil ili trifluorometoksi; R5 predstavlja 2,3-dihidroksipropil, di-(hidroksi-C1-4-alkil)-C1-4-alkil, -CH2-(CH2)k-NHSO2R53, -(CH2)nCH(OH)-CH2-NHSO2R53, -CH2-(CH2)k-NHCOR54, (CH2)nCH(OH)-CH2-NHCOR54, -CH2-(CH2)n-CONR51R52, -CO-NHR51, 1-(3-karboksi-azetidinil)-2-acetil, 1-(2-karboksi-pirolidinil)-2-acetil, 1-(3-karboksi-pirolidinil)-2-acetil, 1-(3-karboksi-azetidinil)-3-propionil, 1-(2-karboksi-pirolidinil)-3-propionil, 1-(3-karboksi-pirolidinil)-3-propionil, (CH2)nCH(OH)-CH2-NR51R52, hidroksi, hidroksi-C2-5-alkoksi, di-(hidroksi-C1-4-alkil)-C1-4-alkoksi, 2,3-dihidroksi-propoksi, 2-hidroksi-3-metoksi-propoksi, -OCH2-(CH2)m-NR51R52, 2-[(azetidin-3-karboksilna kiselina)-1-il]-etoksi, 2-[(azetidin-3-karboksilna kiselina-C1-5-alkilester)-1-il]-etoksi, 2-[(pirolidin-3-karboksilna kiselina)-1-il]-etoksi, 2-[(pirolidin-3-karboksilna kiselina-C1-5-alkilester)-1-il]-etoksi, OCH2-CH(OH)-CH2-NR51R52, 3-[(azetidin-3-karboksilna kiselina)-1-il]-2-hidroksipropoksi, 3-[(azetidin-3-karboksilna kiselina-C1-5-alkilester)-1-il]-2-hidroksipropoksi, 2-hidroksi-3-[(pirolidin-3-karboksilna kiselina)-1-il]-propoksi, 2-hidroksi-3-[(pirolidin-3-karboksilna kiselina-C1-5-alkilester)-1-il]-propoksi, 2-hidroksi-3-[(pirolidin-2-karboksilna kiselina)-1-il]-propoksi, 2-hidroksi-3-[(pirolidin-2-karboksilna kiselina-C1-5-alkilester)-1-il]-propoksi, -OCH2-(CH2)m-NHSO2R53, -OCH2-CH(OH)-CH2-NHSO2R53, -OCH2-(CH2)m-NHCOR54, -OCH2-CH(OH)-CH2-NHCOR54; R51 predstavlja vodik, C1-3-alkil, 2-hidroksietil, 2-hidroksi-1-hidroksimetil-etil, 2,3-dihidroksipropil, karboksimetil, 1-(C1-5-alkilkarboksi)metil, 2-karboksietil ili 2-(C1-5-alkilkarboksi)etil; R52 predstavlja vodik, metil ili etil; R53 predstavlja C1-3-alkil, metilamino, etilamino ili dimetilamino; R54 predstavlja hidroksimetil, hidroksietil, aminometil, metilaminometil, dimetilaminometil, aminoetil, 2-metilamino-etil ili 2-dimetilamino-etil; k predstavlja cijeli broj 1, 2 ili 3; m predstavlja cijeli broj 1 ili 2; n predstavlja 0, 1 ili 2; i R6 predstavlja vodik, C1-4-alkil ili halogen; i sol takvog spoja.
2. Spoj prema zahtjevu 1, naznačen time, da A predstavlja [image] gdje zvjezdice označavaju vezu koja je spojena na piridin-skupinu formula (I); i sol takvog spoja.
3. Spoj prema zahtjevu 1, naznačen time, da A predstavlja [image] , [image] , [image] , [image] ili [image] gdje zvjezdice označavaju vezu koja je spojena na piridin-skupinu formule (I); i sol takvog spoja.
4. Spoj prema zahtjevu 1, naznačen time, da A predstavlja [image] gdje zvjezdica označava vezu koja je spojena na piridin-skupinu formule (I); i sol takvog spoja.
5. Spoj prema bilo kojem od zahtjeva 1 do 4, naznačen time, da R1 predstavlja C1-4-alkil; i sol takvog spoja.
6. Spoj prema bilo kojem od zahtjeva 1 do 4, naznačen time, da R1 predstavlja metil ili etil; i sol takvog spoja.
7. Spoj prema bilo kojem od zahtjeva 1 do 4, naznačen time, da R1 predstavlja metil; i sol takvog spoja.
8. Spoj prema bilo kojem od zahtjeva 1 do 7, naznačen time, da R2 predstavlja C1-5-alkil, C1-3-alkoksi ili ciklopentil; i sol takvog spoja.
9. Spoj prema bilo kojem od zahtjeva 1 do 7, naznačen time, da R2 predstavlja C2-5-alkil; i sol takvog spoja.
10. Spoj prema bilo kojem od zahtjeva 1 do 7, naznačen time, da R2 predstavlja etil, n-propil, izopropil, izobutil ili 3-pentil; i sol takvog spoja.
11. Spoj prema bilo kojem od zahtjeva 1 do 10, naznačen time, da barem jedan od R3, R4 i R6 predstavlja neku skupinu koja nije vodik; i sol takvog spoja.
12. Spoj prema bilo kojem od zahtjeva 1 do 11, naznačen time, da R3 predstavlja vodik; i sol takvog spoja.
13. Spoj prema bilo kojem od zahtjeva 1 do 11, naznačen time, da R3 predstavlja vodik; i R4 predstavlja C1-4-alkil ili C1-4-alkoksi; i R6 predstavlja C1-4-alkil ili halogen; i sol takvog spoja.
14. Spoj prema bilo kojem od zahtjeva 1 do 11, naznačen time, da R3 predstavlja vodik; i R4 predstavlja C1-3-alkil ili metoksi; i R6 predstavlja metil, etil ili kloro; i sol takvog spoja.
15. Spoj prema bilo kojem od zahtjeva 1 do 14, naznačen time, da R5 predstavlja 2,3-dihidroksipropil, di-(hidroksi-C1-4-alkil)-C1-4-alkil, -CH2-(CH2)k-NR51R52, -CH2-(CH2)k-NHSO2R53, -(CH2)nCH(OH)-CH2-NHSO2R53, -CH2-(CH2)k-NHCOR54, (CH2)nCH(OH)-CH2-NHCOR54, -CH2-(CH2)n-CONR51R52, -CO-NHR51, (CH2)nCH(OH)-CH2-NR51R52, hidroksi, hidroksi-C2-5-alkoksi, di-(hidroksi-C1-4-alkil)-C1-4-alkoksi, 2,3-dihidroksi-propoksi, 2-hidroksi-3-metoksi-propoksi, -OCH2-(CH2)m-NR51R52, OCH2-CH(OH)-CH2-NR51R52, -OCH2-(CH2)m-NHSO2R53, -OCH2-CH(OH)-CH2-NHSO2R53, -OCH2-(CH2)m-NHCOR54, -OCH2-CH(OH)-CH2-NHCOR54; i sol takvog spoja.
16. Spoj prema bilo kojem od zahtjeva 1 do 14, naznačen time, da R5 predstavlja 2,3-dihidroksipropil, -CH2-(CH2)k-NR51R52, -CH2-(CH2)k-NHCOR54, (CH2)nCH(OH)-CH2-NHCOR54, -CH2-(CH2)n-CONR51R52, -CO-NHR51, (CH2)nCH(OH)-CH2-NR51R52, hidroksi-C2-5-alkoksi, di-(hidroksi-C1-4-alkil)-C1-4-alkoksi, 2,3-dihidroksi-propoksi, 2-hidroksi-3-metoksi-propoksi, -OCH2-(CH2)m-NR51R52, OCH2-CH(OH)-CH2-NR51R52, -OCH2-(CH2)m-NHCOR54 ili -OCH2-CH(OH)-CH2-NHCOR54; i sol takvog spoja.
17. Spoj prema bilo kojem od zahtjeva 1 do 14, naznačen time, da R5 predstavlja 3-hidroksi-2-hidroksimetil-propoksi, 2,3-dihidroksi-propoksi ili -OCH2-CH(OH)-CH2-NHCOR54; i sol takvog spoja.
18. Spoj prema zahtjevu 1, naznačen time, da je odabran iz skupine koju čine: N-(3-{4-[5-(2-kloro-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2,6-dimetil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; 3-{4-[5-(2-kloro-6-izobutil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2,6-dimetil-fenoksi}-propan-1,2-diol; N-(3-{4-[5-(2-kloro-6-izobutil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2,6-dimetil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; 3-{4-[5-(2-etil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2,6-dimetil-fenoksi}-propan-1,2-diol; 3-{4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2,6-dimetil-fenoksi}-propan-1,2-diol; 2-hidroksi-N-(2-hidroksi-3-{4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2,6-dimetil-fenoksi}-propil)-acetamid; 3-{2-etil-4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenoksi}-propan-1,2-diol; 2-etil-4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenol; (R)-3-{2-etil-4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenoksi}-propan-1,2-diol; (S)-3-{2-etil-4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenoksi}-propan-1,2-diol; 2-{2-etil-4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenoksimetil}-propan-1,3-diol; 2-{2-etil-4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenoksi}-etanol; 3-{2-etil-4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenoksi}-propan-1-ol; N-(3-{2-etil-4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; 3-{4-[5-(2,6-diizobutil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2,6-dimetil-fenoksi}-propan-1,2-diol; 3-{4-[5-(2-kloro-6-izopropoksi-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2,6-dimetil-fenoksi}-propan-1,2-diol; N-(3-{4-[5-(2-kloro-6-izopropoksi-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2,6-dimetil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; 3-{4-[5-(2-etoksi-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2,6-dimetil-fenoksi}-propan-1,2-diol; 3-{4-[5-(2-izopropoksi-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2,6-dimetil-fenoksi}-propan-1,2-diol; 2-hidroksi-N-(2-hidroksi-3-{4-[5-(2-izopropoksi-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2,6-dimetil-fenoksi}-propil)-acetamid; 4-[5-(2-etil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2,6-dimetil-fenol; (R)-3-{4-[5-(2-etil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2,6-dimetil-fenoksi}-propan-1,2-diol; (R)-3-{2-kloro-4-[5-(2-etil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenoksi}-propan-1,2-diol; (S)-3-{4-[5-(2-etil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2,6-dimetil-fenoksi}-propan-1,2-diol; (S)-3-{2-kloro-4-[5-(2-etil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenoksi}-propan-1,2-diol; (S)-3-{2-kloro-4-[5-(2-etil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metoksi-fenoksi}-propan-1,2-diol; N-(3-{4-[5-(2-etil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2,6-dimetil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; N-((R)-3-{2-etil-4-[5-(2-etil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; N-((S)-3-{2-etil-4-[5-(2-etil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; N-(3-{4-[5-(2-etil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2-metil-6-propil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; N-((S)-3-{4-[5-(2-etil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2-metil-6-propil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; N-((R)-3-{2-kloro-4-[5-(2-etil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; N-((S)-3-{2-kloro-4-[5-(2-etil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; N-((R)-3-{2-kloro-4-[5-(2-etil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metoksi-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; N-((S)-3-{2-kloro-4-[5-(2-etil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metoksi-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; N-(3-{4-[5-(2-etil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2-metoksi-6-metil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; N-((S)-3-{2-etil-4-[3-(2-etil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-5-il]-6-metil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; N-((S)-3-{4-[5-(2-etil-6-metil-piridin-4-il)-[1,3,4]oksadiazol-2-il]-2,6-dimetil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; 2,6-dimetil-4-[5-(2-metil-6-propil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-fenol; 2-etil-6-metil-4-[5-(2-metil-6-propil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-fenol; (R)-3-{2,6-dimetil-4-[5-(2-metil-6-propil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-fenoksi}-propan-1,2-diol; (S)-3-{2,6-dimetil-4-[5-(2-metil-6-propil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-fenoksi}-propan-1,2-diol; (R)-3-{2-etil-6-metil-4-[5-(2-metil-6-propil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-fenoksi}-propan-1,2-diol; (S)-3-{2-etil-6-metil-4-[5-(2-metil-6-propil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-fenoksi}-propan-1,2-diol; (R)-3-{2-kloro-6-metoksi-4-[5-(2-metil-6-propil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-fenoksi}-propan-1,2-diol; (S)-3-{2-kloro-6-metoksi-4-[5-(2-metil-6-propil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-fenoksi}-propan-1,2-diol; N-(3-{2,6-dimetil-4-[5-(2-metil-6-propil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; N-((S)-3-{2,6-dimetil-4-[5-(2-metil-6-propil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; N-((R)-3-{2-etil-6-metil-4-[5-(2-metil-6-propil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; N-((S)-3-{2-etil-6-metil-4-[5-(2-metil-6-propil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; N-((R)-3-{2-kloro-6-metoksi-4-[5-(2-metil-6-propil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; N-((S)-3-{2,6-dimetil-4-[5-(2-metil-6-propil-piridin-4-il)-[1,3,4]oksadiazol-2-il]-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; N-((R)-3-{2-etil-6-metil-4-[5-(2-metil-6-propil-piridin-4-il)-[1,3,4]oksadiazol-2-il]-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; N-((S)-3-{2-etil-6-metil-4-[5-(2-metil-6-propil-piridin-4-il)-[1,3,4]oksadiazol-2-il]-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; 2-{2-etil-4-[5-(2-izopropil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenoksi}-etanol; (S)-3-{2-etil-4-[5-(2-izopropil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenoksi}-propan-1,2-diol; N-(3-{2-etil-4-[5-(2-izopropil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; 2-hidroksi-N-((S)-2-hidroksi-3-{4-[5-(2-izopropil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2-metil-6-propil-fenoksi}-propil)-acetamid; N-((S)-3-{2-etil-4-[5-(2-izopropil-6-metil-piridin-4-il)-[1,3,4]tiadiazol-2-il]-6-metil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; 3-{2-kloro-4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenoksi}-propan-1,2-diol; 3-{2-kloro-4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metoksi-fenoksi}-propan-1,2-diol; 3-{2-bromo-4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-fenoksi}-propan-1,2-diol; 1-{2-kloro-4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metoksi-fenoksi}-3-(2-hidroksi-etilamino)-propan-2-ol; 2-hidroksi-N-(2-hidroksi-3-{4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-3-metil-fenoksi}-propil)-acetamid; N-(3-{2-kloro-4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; N-(3-{2-kloro-4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metoksi-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; 2-kloro-4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metoksi-fenol; (S)-3-{4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2-metil-6-propil-fenoksi}-propan-1,2-diol; 2-hidroksi-N-(2-hidroksi-3-{4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-3-metoksi-fenoksi}-propil)-acetamid; 2-hidroksi-N-((S)-2-hidroksi-3-{4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2-metil-6-propil-fenoksi}-propil)-acetamid; 2-hidroksi-N-(2-hidroksi-3-{4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2-metoksi-6-metil-fenoksi}-propil)-acetamid; N-((R)-3-{2-kloro-4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metoksi-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; N-((S)-3-{2-kloro-4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metoksi-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; (R)-3-{2-etil-4-[3-(2-izobutil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-5-il]-6-metil-fenoksi}-propan-1,2-diol; (S)-3-{2-etil-4-[3-(2-izobutil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-5-il]-6-metil-fenoksi}-propan-1,2-diol; 2-hidroksi-N-((R)-2-hidroksi-3-{4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,3,4]oksadiazol-2-il]-2,6-dimetil-fenoksi}-propil)-acetamid; 2-hidroksi-N-((S)-2-hidroksi-3-{4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,3,4]oksadiazol-2-il]-2,6-dimetil-fenoksi}-propil)-acetamid; N-((R)-3-{2-etil-4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,3,4]oksadiazol-2-il]-6-metil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; N-((S)-3-{2-etil-4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,3,4]oksadiazol-2-il]-6-metil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; N-((S)-3-{2-kloro-4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,3,4]oksadiazol-2-il]-6-metoksi-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; N-((S)-3-{2-etil-4-[5-(2-izobutil-6-metil-piridin-4-il)-[1,3,4]tiadiazol-2-il]-6-metil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; 2-etil-4-{5-[2-(1-etil-propil)-6-metil-piridin-4-il]-[1,2,4]oksadiazol-3-il}-6-metil-fenol; (R)-3-(2-etil-4-{5-[2-(1-etil-propil)-6-metil-piridin-4-il]-[1,2,4]oksadiazol-3-il}-6-metil-fenoksi)-propan-1,2-diol; (S)-3-(2-etil-4-{5-[2-(1-etil-propil)-6-metil-piridin-4-il]-[1,2,4]oksadiazol-3-il}-6-metil-fenoksi)-propan-1,2-diol; (R)-3-(4-{5-[2-(1-etil-propil)-6-metil-piridin-4-il]-[1,2,4]oksadiazol-3-il}-2-metil-6-propil-fenoksi)-propan-1,2-diol; (S)-3-(4-{5-[2-(1-etil-propil)-6-metil-piridin-4-il]-[1,2,4]oksadiazol-3-il}-2-metil-6-propil-fenoksi)-propan-1,2-diol; N-[(R)-3-(2-etil-4-{5-[2-(1-etil-propil)-6-metil-piridin-4-il]-[1,2,4]oksadiazol-3-il}-6-metil-fenoksi)-2-hidroksi-propil]-2-hidroksi-acetamid; N-[(S)-3-(2-etil-4-{5-[2-(1-etil-propil)-6-metil-piridin-4-il]-[1,2,4]oksadiazol-3-il}-6-metil-fenoksi)-2-hidroksi-propil]-2-hidroksi-acetamid; N-[(R)-3-(4-{5-[2-(1-etil-propil)-6-metil-piridin-4-il]-[1,2,4]oksadiazol-3-il}-2-metil-6-propil-fenoksi)-2-hidroksi-propil]-2-hidroksi-acetamid; N-[(S)-3-(4-{5-[2-(1-etil-propil)-6-metil-piridin-4-il]-[1,2,4]oksadiazol-3-il}-2-metil-6-propil-fenoksi)-2-hidroksi-propil]-2-hidroksi-acetamid; 3-{4-[5-(2,6-dietil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2,6-dimetil-fenoksi}-propan-1,2-diol; 3-{4-[5-(2,6-dietil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2-etil-6-metil-fenoksi}-propan-1,2-diol; N-((S)-3-{4-[5-(2,6-dietil-piridin-4-il)-[1,3,4]oksadiazol-2-il]-2,6-dimetil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; N-(3-{4-[5-(2-etoksi-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2,6-dimetil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; (R)-3-{2-etil-4-[5-(2-izobutil-6-metoksi-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenoksi}-propan-1,2-diol; (S)-3-{2-etil-4-[5-(2-izobutil-6-metoksi-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenoksi}-propan-1,2-diol; N-((R)-3-{2-etil-4-[5-(2-izobutil-6-metoksi-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; N-((S)-3-{2-etil-4-[5-(2-izobutil-6-metoksi-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; (R)-3-{4-[5-(2-ciklopentil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2-etil-6-metil-fenoksi}-propan-1,2-diol; (S)-3-{4-[5-(2-ciklopentil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2-etil-6-metil-fenoksi}-propan-1,2-diol; N-((R)-3-{4-[5-(2-ciklopentil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2-etil-6-metil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; N-((S)-3-{4-[5-(2-ciklopentil-6-metil-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2-etil-6-metil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; and (S)-3-{2-etil-4-[5-(2-izobutil-6-metil-piridin-4-il)-oksazol-2-il]-6-metil-fenoksi}-propan-1,2-diol; i sol takvog spoja.
19. Farmaceutski sastav, naznačen time, da obuhvaća spoj prema bilo kojem od zahtjeva 1 do 18, ili njegovu farmaceutski prihvatljivu sol i farmaceutski prihvatljiv nosač.
20. Spoj prema bilo kojem od zahtjeva 1 do 18, ili njegova farmaceutski prihvatljiva sol, ili farmaceutski sastav prema zahtjevu 19, naznačen time, da se upotrebljava kao lijek.
21. Spoj prema bilo kojem od zahtjeva 1 do 18, ili njegova farmaceutski prihvatljiva sol, naznačen time, da se upotrebljava u prevenciji ili liječenju bolesti ili poremećaja povezanih s aktiviranim imunološkim sustavom.
22. Spoj prema bilo kojem od zahtjeva 1 do 18, ili njegova farmaceutski prihvatljiva sol, naznačen time, da se upotrebljava u prevenciji ili liječenju bolesti ili poremećaja odabranih iz skupine koju čine: odbijanje transplantiranih organa kao što su bubreg, jetra, srce, pluća, gušterača, rožnica i koža; bolesti presatka protiv domaćina nastale zbog transplantacije matičnih stanica; autoimuni sindromi uključujući reumatoidni artritis, multiplu sklerozu, upalnu bolest crijeva kao što je Crohn-ova bolest i ulcerativni kolitis, psorijazu, psorijatički artritis, tiroiditis kao što je Hashimoto-tiroiditis, uveo-retinitis; atopijske bolesti kao što su rinitis, konjunktivitis, dermatitis; astma; dijabetes tipa I; autoimune bolesti nakon infekcija uključujući reumatsku groznicu i postinfekcijski glomerulonefritis; čvrsti rak i tumorske metastaze.
HRP20130181TT 2006-09-07 2013-03-04 Derivati piridin-4-ila kao sredstva imunomodulacije HRP20130181T1 (hr)

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