HRP20140023T1 - Derivati pirimidin sulfonamida kao modulatori kemokinskih receptora - Google Patents

Derivati pirimidin sulfonamida kao modulatori kemokinskih receptora Download PDF

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Publication number
HRP20140023T1
HRP20140023T1 HRP20140023TT HRP20140023T HRP20140023T1 HR P20140023 T1 HRP20140023 T1 HR P20140023T1 HR P20140023T T HRP20140023T T HR P20140023TT HR P20140023 T HRP20140023 T HR P20140023T HR P20140023 T1 HRP20140023 T1 HR P20140023T1
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Croatia
Prior art keywords
compound
phenyl
independently selected
group
substituents independently
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HRP20140023TT
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English (en)
Inventor
David Ranulf Cheshire
Rhona Jane Cox
Premji Meghani
Cherylin Francis Preston
Neal Michael Smith
Jeffrey Paul Stonehouse
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Astrazeneca Ab
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=35549576&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=HRP20140023(T1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from GB0419235A external-priority patent/GB0419235D0/en
Priority claimed from GB0502544A external-priority patent/GB0502544D0/en
Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab
Publication of HRP20140023T1 publication Critical patent/HRP20140023T1/hr

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Claims (25)

1. Spoj sa formulom (1) [image] naznačen time da R1 je C1-8alkil supstituiran sa fenilom koji je proizvoljno supstituiran sa 1, 2 ili 3 supstituenta neovisno odabrana od fluoro, kloro, bromo, metoksi, metila i trifluorometila; X je -CH2-, veza, kisik, sumpor, sulfoksid, ili sulfon; R2 je C3-7karbociklil, proizvoljno supstituiran sa 1, 2 ili 3 supstituenta neovisno odabrana od: fluoro, -OR4, -NR5R6 -CONR5R6, -COOR7, -NR8COR9, -SR10, -SO2R10, -SO2NR5R6, -NR8SO2R9; ili R2 je 3-8 člani prsten koji proizvoljno sadrži 1, 2 ili 3 atoma odabrana od O, S, -NR8 i pri čemu je prsten proizvoljno supstituiran sa 1,2 ili 3 supstituenta neovisno odabrana od C1-3alkila, fluoro, -OR4, -NR5R6 -CONR5R6, -COOR7, -NR8COR9, -SR10, -SO2R10, -SO2NR5R6, -NR8SO2R9; ili R2 je fenil ili monociklički ili biciklički heteroarilni prsten koji sadrži 5 do 10 atoma u prstenu od kojih su 1, 2, 3 ili 4 atoma u prstenu odabrani od dušika, sumpora ili kisika; svaki od kojih je proizvoljno supstituiran sa 1, 2 ili 3 supstituenta neovisno odabrana od halo, cijano, nitro, -OR4, -NR5R6, -CONR5R6, -NR8COR9, -SO2NR5R6, -NR8SO2R9, C1-6alkila i trifluorometila; ili R2 je skupina odabrana od C1-8alkila, C2-6alkenila ili C2-6alkinila pri čemu je skupina supstituirana sa 1, 2 ili 3 supstituenta neovisno odabrana od hidroksi, amino, C1-6alkoksi, C1-6alkilamino, di(C1-6alkil)amino, N-(C1-6alkil)-N-(fenil)amino, N-C1-6alkilkarbamoila, N,N-di(C1-6alkil)karbamoila, N-(C1-6alkil)-N-(fenil)karbamoila, karboksi, fenoksikarbonila, -NR8COR9, -SO2R10, -SO2NR5R6, -NR8SO2R9, te -CONR5R6; R3 je trifluorometil ili skupina-NR5R6, ili R3 je fenil, naftil, monociklički ili biciklički heteroarilni prsten koji sadrži 5 do 10 atoma u prstenu od kojih su 1, 2, 3 ili 4 atoma u prstenu odabrani od dušika, sumpora ili kisika pri čemu heteroprsten može biti djelomično ili potpuno zasićen i jedan ili više atoma ugljika u prstenu mogu tvoriti karbonilnu skupinu, te pri čemu je svaka fenilna ili heteroarilna skupina proizvoljno supstituirana sa 1, 2 ili 3 supstituenta neovisno odabrana od halo, cijano, nitro, fenila, heteroarila, -OR4, -NR5R6, -CONR5R6, -COR7-, -COR20,--COOR7, -NR8COR9, -SR10, -SO2R10, -SO2NR5R6, -NR8SO2R9, trifluorometil ili C1-6alkil [proizvoljno nadalje supstituiran sa 1, 2 ili 3 supstituenta neovisno odabranih od halo, cijano, nitro, -OR20, -COOR20, -COR20, NR18R19, -CONR18R19, -NR18COR19, -SO2R20, -SO2NR18R19, NR18SO2R19, fenila ili monocikličkog ili bicikličkog heteroarilnog prstena koji sadrži 5 do 10 atoma u prstenu od kojih su 1, 2, 3 ili 4 atoma u prstenu odabrani od dušika, sumpora ili kisika, pri čemu heteroprsten može biti djelomično ili potpuno zasićen; te pri čemu je svaka fenilna ili heteroarilna skupina proizvoljno supstituirana sa 1, 2 ili 3 supstituenta neovisno odabrana od halo, cijano, nitro, -OR20, -NR5R6, -CONR5R6, -COR7, -COOR7, -NR8COR9, -SR10, -SO2R10, -SO2NR5R6, -NR8SO2R9, heteroaril, C1-6alkil (proizvoljno nadalje supstituiran sa 1, 2 ili 3 supstituenta neovisno odabranih od halo, cijano, nitro, -OR20, -COOR20, COR20, NR18R19, -CONR18R19, NR18COR19, SO2R20, -SO2NR18R19, NR18SO2R19, ili R3 je skupina odabrana od C3-7karbociklila, C1-8alkila, C2-6alkenila i C2-6alkinila pri čemu je skupina proizvoljno supstituirana sa 1, 2 ili 3 supstituenta neovisno odabrana od halo, -OR4, -NR5R6, -CONR5R6, -COR7,-COOR7, -NR8COR9, -SR10, -SO2R10, -SO2NR5R6, -NR8SO2R9, fenila ili monocikličkog ili bicikličkog heteroarilnog prstena koji sadrži 5 do 10 atoma u prstenu od kojih su 1, 2, 3 ili 4 atoma u prstenu odabrani od dušika, sumpora ili kisika, pri čemu heteroprsten može biti djelomično ili potpuno zasićen; te pri čemu svaki fenil ili monociklička ili biciklička heteroarilna skupina je proizvoljno supstituirana sa 1, 2 ili 3 supstituenta neovisno odabrana od halo, cijano, nitro, -OR4, -NR5R6, -CONR5R6, -COR7, -COOR7, -NR8COR9, -SR10, -SO2R10, -SO2NR5R6, -NR8SO2R9, C1-6alkila, ili trifluorometila; R4 je vodik ili skupina odabrana od C1-6alkila i fenila, pri čemu je skupina proizvoljno supstituirana sa 1 ili 2 supstituenta neovisno odabrana od halo, fenil, -OR11 i - NR12R13; R5 i R6 su neovisno vodik ili skupina odabrana od C1-6alkila i fenila i monocikličkog ili bicikličkog heteroarilnog prstena, koji sadrži 5 do 10 atoma u prstenu od kojih su 1, 2, 3 ili 4 atoma u prstenu odabrani od dušika, sumpora ili kisika, pri čemu heteroprsten može biti djelomično ili potpuno zasićen; pri čemu je skupina proizvoljno supstituirana sa 1, 2 ili 3 supstituenta neovisno odabrana od halo, fenila, -OR14,-NR15R16, -COOR14, -CONR15R16, -NR15COR16, -SO2R10, -SO2NR15R16 i NR15SO2R16; ili R5 i R6 zajedno s atomom dušika na koji su vezani tvore 4- do 7-člani zasićeni heterociklički prstenasti sustav koji proizvoljno sadrži dodatni heteroatom odabran od kisika, -SO(n)- (gdje n = 0, 1 ili 2) i atoma dušika, u kojem je prsten proizvoljno supstituiran sa 1, 2 ili 3 supstituenta neovisno odabrana od fenila, monocikličkog ili bicikličkog heteroarilnog prstena koji sadrži 5 do 10 atoma u prstenu od kojih su 1, 2, 3 ili 4 atoma u prstenu odabrani od dušika, sumpora ili kisika; -OR14, -COR20, -COOR14, -NR15R16, -CONR15R16, -NR15COR16, -SO2R10, -SO2NR15R16, NR15SO2R16 ili C1-6alkil (proizvoljno nadalje supstituiran sa 1 ili 2 ili 3 supstituenta neovisno odabrana od halo, -NR15R16 i -OR17 ili cijano, nitro, -OR20, -COOR20, -COR20, -NR18R19, -CONR18R19, -NR18COR19,-SO2R20, -SO2NR18R19, NR18SO2R19 skupina); R10 je vodik ili skupina odabrana od C1-6alkila ili fenila, pri čemu je skupina proizvoljno supstituirana sa 1, 2 ili 3 supstituenta neovisno odabrana od halo, fenila, -OR17i -NR15R16; te svaki od R7, R8, R9, R11, R12, R13, R14 R15, R16, R17 je neovisno vodik, C1-6alkil ili fenil; R18, R19, i R20 su vodik ili skupina odabrana od C1-6alkila ili monocikličkog ili bicikličkog heteroarilnog prstena koji sadrži 5 do 10 atoma u prstenu od kojih su 1, 2, 3 ili 4 atoma u prstenu odabrani od dušika, sumpora ili kisika (pri čemu heteroprsten može biti djelomično ili potpuno zasićen) ili fenila, pri čemu je skupina proizvoljno supstituirana sa 1, 2 ili 3 supstituenta neovisno odabrana od halo, nitro, -CN, -OR4, -NR8R9, -CONR8R9, -COR7, -COOR7, NR8COR9, -SR10, -SO2R10, -SO2NR8R9, -NR8SO2R9, C1-6alkila ili monocikličkog ili bicikličkog heteroarilnog prstena, koji sadrži 5 do 10 atoma u prstenu od kojih su 1, 2, 3 ili 4 atoma u prstenu odabrani od dušika, sumpora ili kisika; ili njegova farmaceutski prihvatljiva sol, solvat ili ester koji hidrolizira in vivo.
2. Spoj, njegova farmaceutski prihvatljiva sol, solvat ili ester koji hidrolizira in vivo prema zahtjevu 1 naznačen time da X je odabran od -CH2-, veze, kisika i sumpora.
3. Spoj, ili njegova farmaceutski prihvatljiva sol, solvat ili ester koji hidrolizira in vivo prema zahtjevu 1 naznačen time da R2 je C1-8alkil proizvoljno supstituiran sa 1, 2 ili 3 supstituenta neovisno odabrana od C1-6alkoksi, hidroksi i fluoro; ili R2 je 5-6 člani prsten koji proizvoljno sadrži 1, 2 ili 3 heteroatoma odabrana od O, S,-NR8 i pri čemu je prsten proizvoljno supstituiran sa -OR4.
4. Spoj, njegova farmaceutski prihvatljiva sol, solvat ili ester koji hidrolizira in vivo prema zahtjevu 1 naznačen time da R3 je C3-7karbociklil, C1-8alkil, -NR5R6, fenil, monociklički ili biciklički heteroarilni prsten koji sadrži 5 do 10 atoma u prstenu od kojih su 1, 2, 3 ili 4 atoma u prstenu odabrani od dušika, sumpora ili kisika pri čemu heteroprsten može biti djelomično ili potpuno zasićen i jedan ili više atoma ugljika u prstenu mogu tvoriti karbonilnu skupinu, te pri čemu svaki fenil ili heteroarilna skupina je proizvoljno supstituirana sa 1, 2 ili 3 supstituenta neovisno odabrana od cijano, heteroaril, -OR4, -NR5R6, -CONR5R6, -COR7-, -COR20, -NR8COR9, -SO2R10, -SO2NR5R6, C1-6alkil [proizvoljno nadalje supstituiran sa 1, 2 ili 3 supstituenta neovisno odabrana od -OR20, -COR20, -NR18R19, -CONR18R19, fenila ili monocikličkog ili bicikličkog heteroarilnog prstena, koji sadrži 5 do 10 atoma u prstenu od kojih su 1, 2, 3 ili 4 atoma u prstenu odabrani od dušika, sumpora ili kisika, pri čemu heteroprsten može biti djelomično ili potpuno zasićen; te pri čemu svaki fenil ili heteroarilna skupina je proizvoljno supstituirana sa 1, 2 ili 3 supstituenta neovisno odabrana od nitro, -OR20, -NR5R6, -NR8COR9, heteroaril, C1-6alkil (proizvoljno nadalje supstituiran sa 1, 2 ili 3 supstituenta neovisno odabrana od cijano, -OR20.
5. Spoj, njegova farmaceutski prihvatljiva sol, solvat ili ester koji hidrolizira in vivo prema zahtjevu 1 naznačen time da je odabran od N-[2-[[(2,3-Difluorofenil)metil]tio]-6-{[(1R,2S)-2,3-dihidroksi-1-metilpropil]oksi}-4-pirimidinil]-1-azetidinsulfonamida.
6. Spoj prema zahtjevu 1 naznačen time da je N-[2-[[(2,3-Difluorofenil)metil]tio]-6-{[(1R,2S)-2,3-dihidroksi-1-metilpropil]oksi}-4-pirimidinil]-1-azetidinsulfonamid.
7. Spoj prema zahtjevu 6 naznačen time da je za upotrebu kao medikament.
8. Spoj prema zahtjevu 6 naznačen time da je za upotrebu kao medikament za liječenje astme, alergijskog rinitisa, KOPB, upalne bolesti crijeva, osteoartritisa, osteoporoze, reumatoidnog artritisa, ili psorijaze.
9. Upotreba spoja prema zahtjevu 6 naznačena time da je za proizvodnju medikamenta za liječenje ljudskih bolesti ili stanja kod kojih je korisna modulacija aktivnosti kemokinskih receptora.
10. Upotreba spoja prema zahtjevu 6 naznačena time da je za proizvodnju medikamenta za liječenje astme, alergijskog rinitisa, KOPB, upalne bolesti crijeva, sindroma iritabilnog crijeva, osteoartritisa, osteoporoze, reumatoidnog artritisa, ili psorijaze.
11. Farmaceutski pripravak naznačen time da sadrži spoj prema zahtjevu 6 i farmaceutski prihvatljiv razrjeđivač ili nosač.
12. Spoj, ili njegova farmaceutski prihvatljiva sol, solvat ili ester koji hidrolizira in vivo prema bilo kojem zahtjevu od 1 do 5 naznačen time da je za upotrebu kao medikament.
13. Spoj, ili njegova farmaceutski prihvatljiva sol, solvat ili ester koji hidrolizira in vivo prema bilo kojem zahtjevu od 1 do 5 naznačen time da je za upotrebu kao medikament za liječenje astme, alergijskog rinitisa, KOPB, upalne bolesti crijeva, osteoartritisa, osteoporoze, reumatoidnog artritisa, ili psorijaze.
14. Spoj, ili njegova farmaceutski prihvatljiva sol, solvat ili ester koji hidrolizira in vivo prema bilo kojem zahtjevu od 1-5, naznačen time da je za upotrebu kao medikament za liječenje raka.
15. Upotreba spoja, ili njegove farmaceutski prihvatljive soli, solvata ili estera koji hidrolizira in vivo, prema bilo kojem zahtjevu od 1 do 5 naznačena time da je za proizvodnju medikamenta za liječenje ljudskih bolesti ili stanja kod kojih je korisna modulacija aktivnosti kemokinskih receptora.
16. Upotreba spoja, ili njegove farmaceutski prihvatljive soli, solvata ili estera koji hidrolizira in vivo, prema bilo kojem zahtjevu od 1 do 5 naznačena time da je za proizvodnju medikamenta za liječenje astme, alergijskog rinitisa, KOPB, upalne bolesti crijeva, sindroma iritabilnog crijeva, osteoartritisa, osteoporoze, reumatoidnog artritisa, ili psorijaze.
17. Upotreba spoja, ili njegove farmaceutski prihvatljive soli, solvata ili estera koji hidrolizira in vivo, prema bilo kojem zahtjevu od 1 do 5 naznačena time da je za proizvodnju medikamenta za liječenje raka.
18. Farmaceutski pripravak naznačen time da sadrži spoj, ili njegovu farmaceutski prihvatljivu sol, solvat ili ester koji hidrolizira in vivo prema bilo kojem zahtjevu od 1 do 5 i farmaceutski prihvatljiv razrjeđivač ili nosač.
19. Postupak za dobivanje spoja prema zahtjevu 1 ili njegove farmaceutski prihvatljive soli, solvata ili estera koji hidrolizira in vivo, naznačen time da sadrži korake: (a) obradu spoja sa formulom (2a): [image] pri čemu R1, R2, R3 i X su kako je definirano u formuli (1) i L je izlazna skupina sa sulfonamidom sa formulom R3SO2NH2 gdje je R3 kako je definirano u formuli (1); i proizvoljno zatim, jedan ili više koraka (i), (ii), (iii), (iv), ili (v) u bilo kojem poretku: i) uklanjanje bilo kojih zaštitnih skupina; ii) konverziju spoja sa formulom (1) u drugi spoj sa formulom (1) iii) tvorbu soli iv) stvaranje predlijeka v) stvaranje estera koji hidrolizira in vivo; ili (b) obradu spoja sa formulom (2b): [image] pri čemu R1 i R3 su kako je definirano u formuli (1), L je izlazna skupina, PG je zaštitna skupina ili vodik i gdje X je kisik ili sumpor, sa alkoholima HOR2 ili odgovarajućim tiolima HSR2 pri čemu je R2 kako je definirano u formuli (1) u prisutnosti pogodne baze ili otapala, i proizvoljno zatim, jedan ili više koraka (i), (ii), (iii), (iv), ili (v) u bilo kojem poretku: i) uklanjanje bilo kojih zaštitnih skupina; ii) konverziju spoja sa formulom (1) u drugi spoj sa formulom (1) iii) tvorbu soli iv) stvaranje predlijeka v) tvaranje estera koji hidrolizira in vivo.
20. Spoj sa formulom (2a) [image] naznačen time da R1, R2 i X su kako je definirano u formuli (1) iz zahtjeva 1 i L je izlazna skupina, uz uvjet da kada R1 je benzil, X je kisik, R2 je metil tada L nije klor ili kada R1 je benzil, X je veza, R2 je propil tada L nije klor.
21. Farmaceutski pripravak naznačen time da sadrži spoj sa formulom (1) prema zahtjevu 1 ili njegovu farmaceutski prihvatljivu sol, solvat ili ester koji hidrolizira in vivo, u kombinaciji s drugim farmaceutskim sredstvom.
22. Farmaceutski pripravak prema zahtjevu 21 naznačen time da je za liječenje astme, alergijskog rinitisa, KOPB, upalne bolesti crijeva, sindroma iritabilnog crijeva, osteoartritisa, osteoporoze, reumatoidnog artritisa, ili psorijaze.
23. Farmaceutski pripravak prema zahtjevu 21 naznačen time da je za liječenje raka.
24. Spoj naznačen time da je 4-kloro-2-[(2,3-difluorobenzil)tio]-6-{(1R)-1-[(4S)-2,2-dimetil-1,3-dioksolan-4-il]etoksi}pirimidin.
25. Spoj naznačen time da je N-[2-[[(2,3-difluorofenil)metil]tio]-6-{(1R)-1-[(4S)-2,2-dimetil-1,3-dioksolan-4-il]etoksi}pirimidinil]-1-azetidinsulfonamid.
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