HRP20140098T1 - Derivati piridin-4-ila kao agonisti s1p1/edg1 - Google Patents

Derivati piridin-4-ila kao agonisti s1p1/edg1 Download PDF

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HRP20140098T1
HRP20140098T1 HRP20140098AT HRP20140098T HRP20140098T1 HR P20140098 T1 HRP20140098 T1 HR P20140098T1 HR P20140098A T HRP20140098A T HR P20140098AT HR P20140098 T HRP20140098 T HR P20140098T HR P20140098 T1 HRP20140098 T1 HR P20140098T1
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methyl
pyridin
oxadiazol
methoxy
ethyl
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Martin Bolli
Cyrille Lescop
Boris Mathys
Keith Morrison
Claus Mueller
Oliver Nayler
Beat Steiner
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Actelion Pharmaceuticals Ltd.
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Claims (29)

1. Spoj, naznačen time, da ima formulu (I), [image] u kojoj A predstavlja [image] gdje zvjezdice označuju vezu koja je spojena na piridinsku skupinu formule (I); R1 predstavlja 3-pentil, 3-metil-but-1-il, ciklopentil, ili cikloheksil; R2 predstavlja metoksi; R3 predstavlja 2,3-dihidroksipropoksi, -OCH2-CH(OH)-CH2-NHCO-CH2OH, -OCH2-CH(OH)-CH2N(CH3)-COCH2OH, -NHSO2CH3, ili -NHSO2CH2CH3; i R4 predstavlja etil ili kloro; ili njegove soli.
2. Spoj prema zahtjevu 1, naznačen time, da je stereocentar u S-konfiguraciji od R3 skupina 2,3-dihidroksipropoksi, -OCH2-CH (OH)-CH2-NHCO-CH2OH, i -OCH2-CH(OH)-CH2N(CH3)-CO-CH2OH, ili njegove soli.
3. Spoj prema zahtjevu 1, naznačen time, da je stereocentar u R-konfiguraciji od R3 skupina 2,3-dihidroksipropoksi, -OCH2-CH (OH)-CH2-NHCO-CH2OH, i -OCH2-CH(OH)-CH2N(CH3)-CO-CH2OH, ili njegove soli.
4. Spoj prema bilo kojem od zahtjeva 1 do 3, naznačen time, da A predstavlja [image] gdje zvjezdice označuju vezu koja je spojena na piridinsku skupinu formule (I); ili njegove soli.
5. Spoj prema bilo kojem od zahtjeva 1 do 3, naznačen time, da A predstavlja [image] gdje zvjezdice označuju vezu koja je spojena na piridinsku skupinu formule (I); ili njegove soli.
6. Spoj prema bilo kojem od zahtjeva 1 do 3, naznačen time, da A predstavlja [image] ili njegove soli.
7. Spoj prema bilo kojem od zahtjeva 1 do 6, naznačen time, da R1 predstavlja 3-pentil, ili njegove soli.
8. Spoj prema bilo kojem od zahtjeva 1 do 6, naznačen time, da R1 predstavlja 3-metil-but-1-il, ili njegove soli.
9. Spoj prema bilo kojem od zahtjeva 1 do 6, naznačen time, da R1 predstavlja ciklopentil, ili njegove soli.
10. Spoj prema bilo kojem od zahtjeva 1 do 6, naznačen time, da R1 predstavlja cikloheksil, ili njegove soli.
11. Spoj prema bilo kojem od zahtjeva 1 do 10, naznačen time, da R3 predstavlja 2,3-dihidroksipropoksi, ili njegove soli.
12. Spoj prema bilo kojem od zahtjeva 1 do 10, naznačen time, da R3 predstavlja -OCH2-CH(OH)-CH2-NHCO-CH2OH, ili njegove soli.
13. Spoj prema bilo kojem od zahtjeva 1 do 10, naznačen time, da R3 predstavlja -OCH2-CH(OH)-CH2N(CH3)-CO-CH2OH, ili njegove soli.
14. Spoj prema bilo kojem od zahtjeva 1 do 10, naznačen time, da R3 predstavlja -NHSO2CH3, ili njegove soli.
15. Spoj prema bilo kojem od zahtjeva 1 do 10, naznačen time, da R3 predstavlja -NHSO2CH2CH3, ili njegove soli.
16. Spoj prema bilo kojem od zahtjeva 1 do 15, naznačen time, da R4 predstavlja etil, ili njegove soli.
17. Spoj prema bilo kojem od zahtjeva 1 do 15, naznačen time, da R4 predstavlja klor, ili njegove soli.
18. Spoj prema zahtjevu 1, naznačen time, da je odabran iz skupine koja se sastoji od sljedećih: (S)-3-(2-etil-4-{5-[2-(1-etil-propil)-6-metoksi-piridin-4-il]-[1,2,4]oksadiazol-3-il}-6-metil-fenoksi)-propan-1,2-diol; (S)-3-{4-[5-(2-ciklopentil-6-metoksi-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2-etil-6-metil-fenoksi}-propan-1,2-diol; (R)-3-{4-[5-(2-ciklopentil-6-metoksi-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2-etil-6-metil-fenoksi}-propan-1,2-diol; (S)-3-{4-[5-(2-cikloheksil-6-metoksi-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2-etil-6-metil-fenoksi}-propan-1,2-diol; etansulfonska kiselina-{2-kloro-4-[5-(2-ciklopentil-6-metoksi-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenil}-amid; N-[(S)-3-(2-etil-4-{5-[2-(1-etil-propil)-6-metoksi-piridin-4-il]-[1,2,4]oksadiazol-3-il}-6-metil-fenoksi)-2-hidroksi-propil]-2-hidroksi-acetamid; N-((S)-3-{4-[5-(2-ciklopentil-6-metoksi-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-cikloheksil-6-metoksi-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-metoksi-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2-etil-6-metil-fenoksi}-2-hidroksi-propil)-2-hidroksi-N-metil-acetamid; N-(2-kloro-4-{5-[2-(1-etil-propil)-6-metoksi-piridin-4-il]-[1,2,4]oksadiazol-3-il}-6-metil-fenil)-metansulfonamid; N-{2-kloro-4-[5-(2-ciklopentil-6-metoksi-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenil}-metansulfonamid; (S)-3-{2-kloro-4-[5-(2-ciklopentil-6-metoksi-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenoksi}-propan-1,2-diol; N-((S)-3-{2-kloro-4-[5-(2-ciklopentil-6-metoksi-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; (S)-3-(2-etil-4-{5-[2-metoksi-6-(3-metil-butil)-piridin-4-il]-[1,2,4]oksadiazol-3-il}-6-metil-fenoksi)-propan-1,2-diol; N-[(S)-3-(2-etil-4-{5-[2-metoksi-6-(3-metil-butil)-piridin-4-il]-[12,4]oksadiazol-3-il}-6-metil-fenoksi)-2-hidroksi-propil]-2-hidroksi-acetamid; N-{2-kloro-4-[5-(2-cikloheksil-6-metoksi-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenil}-metansulfonamid; N-(2-etil-4-{5-[2-(1-etil-propil)-6-metoksi-piridin-4-il]-[1,2,4]oksadiazol-3-il}-6-metil-fenil)-metansulfonamid; N-{4-[5-(2-ciklopentil-6-metoksi-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2-etil-6-metil-fenil}-metansulfonamid; N-{4-[5-(2-cikloheksil-6-metoksi-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2-etil-6-metil-fenil}-metansulfonamid; (S)-3-{4-[3-(2-ciklopentil-6-metoksi-piridin-4-il)-[1,2,4]oksadiazol-5-il]-2-etil-6-metil-fenoksi}-propan-1,2-diol; (R)-3-{4-[3-(2-ciklopentil-6-metoksi-piridin-4-il)-[1,2,4]oksadiazol-5-il]-2-etil-6-metil-fenoksi}-propan-1,2-diol; N-((S)-3-{4-[3-(2-ciklopentil-6-metoksi-piridin-4-il)-[1,2,4]oksadiazol-5-il]-2-etil-6-metil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; N-((R)-3-{4-[3-(2-ciklopentil-6-metoksi-piridin-4-il)-[1,2,4]oksadiazol-5-il]-2-etil-6-metil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; (S)-3-{4-[5-(2-ciklopentil-6-metoksi-piridin-4-il)-[1,3,4]oksadiazol-2-il]-2-etil-6-metil-fenoksi}-propan-1,2-diol; (R)-3-{4-[5-(2-ciklopentil-6-metoksi-piridin-4-il)-[1,3,4]oksadiazol-2-il]-2-etil-6-metil-fenoksi}-propan-1,2-diol; N-((S)-3-{4-[5-(2-ciklopentil-6-metoksi-piridin-4-il)-[1,3,4]oksadiazol-2-il]-2-etil-6-metil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; i N-((R)-3-{4-[5-(2-ciklopentil-6-metoksi-piridin-4-il)-[1,3,4]oksadiazol-2-il]-2-etil-6-metil-fenoksi}-2-hidroksi-propil)-2-hidroksi-acetamid; ili soli tih spojeva.
19. Spoj prema zahtjevu 1, naznačen time, da je odabran iz skupine koja se sastoji od sljedećih: (S)-3-{2-kloro-4-[5-(2-cikloheksil-6-metoksi-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil- fenoksi}-propan-1,2-diol; i N-(2-etil-4-(5-(2-izopentil-6-metoksipiridin-4-il)-1,2,4-oksadiazol-3-il)-6-metilfenil)metansulfonamid; ili soli tih spojeva.
20. Spoj prema zahtjevu 1, naznačen time, da je to (S)-3-{4-[5-(2-ciklopentil-6-metoksi-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2-etil-6-metil- fenoksi}-propan-1,2-diol ili njegova sol.
21. Spoj prema zahtjevu 1, naznačen time, da je to N-((S)-3-{4-[5-(2-ciklopentil-6-metoksi-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2-etil-6-metil-fenoksi}-2-hidroksi-propil)-2-hidroksi-N-metil-acetamid ili njegova sol.
22. Spoj prema zahtjevu 1, naznačen time, da je to N-{2-kloro-4-[5-(2-ciklopentil-6-metoksi-piridin-4-il)-[1,2,4]oksadiazol-3-il]-6-metil-fenil}-metansulfonamid ili njegova sol.
23. Spoj prema zahtjevu 1, naznačen time, da je to N-{4-[5-(2-ciklopentil-6-metoksi-piridin-4-il)-[1,2,4]oksadiazol-3-il]-2-etil-6-metil-fenil}-metansulfonamid ili njegova sol.
24. Farmaceutski sastav, naznačen time, da obuhvaća spoj prema bilo kojem od zahtjeva 1 do 23, ili njegovu farmaceutski prihvatljivu sol, te farmaceutski prihvatljiv nosač.
25. Spoj prema bilo kojem od zahtjeva 1 do 23 ili njegova farmaceutski prihvatljiva sol ili farmaceutski sastav prema zahtjevu 24, naznačen(a) time, da se upotrebljava kao lijek.
26. Spoj prema bilo kojem od zahtjeva 1 do 23 ili njegova farmaceutski prihvatljiva sol, naznačen(a) time, da se upotrebljava u prevenciji ili liječenju bolesti ili poremećaja povezanih s aktiviranjem imunološkog sustava.
27. Spoj prema bilo kojem od zahtjeva 1 do 23 ili njegova farmaceutski prihvatljiva sol, naznačen(a) time, da se upotrebljava u prevenciji ili liječenju bolesti ili poremećaja odabranih iz skupine koju čine odbacivanje transplatiranih organa kao što su bubrezi, jetra, srce, pluća, gušterača, rožnica i koža; bolesti koje izaziva usadak protiv stanice domaćina nastale nakon transplatacije matičnih stanica; autoimuni sindromi uključujući reumatoidni artritis, multiplu sklerozu, upalne bolesti crijeva kao što su Crohnova bolest i ulcerativni kolitis, psorijazu, psorijastični artritis, tiroiditis kao što je Hashimotoov tiroiditis, uveo-retinitis; atopijske bolesti kao što su rinitis, konjunktivitis, dermatitis; astma; dijabetes tipa I; autoimune bolesti nastale nakon infekcija uključujući reumatsku groznicu i postinfekcijski glomerulonefritis; čvrsti tumori i metastaze tumora.
28. Spoj prema bilo kojem od zahtjeva 1 do 23 ili njegova farmaceutski prihvatljiva sol, naznačen(a) time, da se upotrebljava u prevenciji ili liječenju bolesti ili poremećaja odabranih iz skupine koju čine odbacivanje transplantiranih organa kao što su bubrezi, jetra, srce i pluća; bolesti koje izaziva usadak protiv stanice domaćina nastale nakon transplantacije matičnih stanica; autoimuni sindromi uključujući reumatoidni artritis, multiplu sklerozu, psorijazu, psorijatički artritis, Crohnovu bolest i Hashimotoov tiroiditis; te atopijski dermatitis.
29. Spoj prema bilo kojem od zahtjeva 1 do 23 ili njegova farmaceutski prihvatljiva sol, naznačen(a) time, da se upotrebljava u prevenciji ili liječenju multiple skleroze ili psorijaze.
HRP20140098AT 2009-07-16 2014-02-04 Derivati piridin-4-ila kao agonisti s1p1/edg1 HRP20140098T1 (hr)

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