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SI2978752T1 - Derivati 6-(5-hidroksi-1H-pirazol-1-il)nikotinamida in njihova uporaba kot inhibitorji PHD - Google Patents

Derivati 6-(5-hidroksi-1H-pirazol-1-il)nikotinamida in njihova uporaba kot inhibitorji PHD Download PDF

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SI2978752T1
SI2978752T1 SI201430629T SI201430629T SI2978752T1 SI 2978752 T1 SI2978752 T1 SI 2978752T1 SI 201430629 T SI201430629 T SI 201430629T SI 201430629 T SI201430629 T SI 201430629T SI 2978752 T1 SI2978752 T1 SI 2978752T1
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pyrazol
hydroxy
pyridin
carbonyl
methylbenzonitrile
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SI201430629T
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Jason W. Brown
Melinda Davis
Anthony Ivetac
Benjamin Jones
Andre A. Kiryanov
Jon Kuehler
Marion Lanier
Joanne Miura
Sean Murphy
Xiaolun Wang
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Takeda Pharmaceutical Company Limited
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Publication of SI2978752T1 publication Critical patent/SI2978752T1/sl

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Claims (17)

  1. Derivati 6-(5-hidroksi-lH-pirazol-l-il)nikotinamida in njihova uporaba kot inhibitorji PHD Patentni zahtevki
    1. Spojina s formulo
    ali njena farmacevtsko sprejemljiva sol, kjer q predstavlja 0, 1 ali 2; s je 0, 1 2; R-3 je vsakokrat neodvisno izbran iz skupine, ki vsebuje vodik, hidroksil, amino, Ci-g alkilamino, dano, halo, neobvezno substituiran Cm alkil in Cm alkoksi; Rt je izbran iz skupine, ki vsebuje vodik, ciano, halo, metil, etil, metoksi in trifluorometil; Rs je izbran iz skupine, ki vsebuje
    G je ogljik; A je izbran iz skupine, ki vsebuje N, O, S, CR^ in NR$; E je izbran iz skupine, ki vsebuje N, O, S in CR$; pod pogojem, daje samo eden izmed A in E lahko O ali S; ali G je N in A in E sta CR$; ali G in A sta N in E je CR$; ali G, A in E so N; R6 je vsakokrat neodvisno izbran iz skupine, ki vsebuje vodik, ciano, halo, C3.8 cikloalkil, neobvezno substituiran C1-6 alkil, C1.4 alkoksi in trifluorometil; R7 je izbran iz skupine, ki vsebuje ciano in cianometil; Rg je vsakokrat neodvisno izbran iz skupine, ki vsebuje vodik, ciano, halo, Cm alkil, Cm alkoksi in trifluorometil; in R9 je izbran iz skupine, ki vsebuje vodik, C 1.6 alkil neobvezno substituiran z do 1 do 3 fluoro in C3.8 cikloalkil.
  2. 2. Spojina ali farmacevtsko sprejemljiva sol po zahtevku 1, kjer R5 predstavlja
  3. 3. Spojina ali farmacevtsko sprejemljiva sol po kateremkoli zahtevku 1 ali 2, kjer R9 predstavlja Cm alkil.
  4. 4. Spojina ali farmacevtsko sprejemljiva sol po kateremkoli zahtevku 1 do 3, kjer s predstavlja 1 in q je 1.
  5. 5. Spojina ali farmacevtsko sprejemljiva sol po kateremkoli zahtevku 1 do 4, kjer je vsak Rg vodik.
  6. 6. Spojina ali farmacevtsko sprejemljiva sol po kateremkoli zahtevku 1 do 4, kjer eden izmed Rg predstavlja Cm alkil in vsak naslednji Rg predstavlja vodik.
  7. 7. Spojina ali farmacevtsko sprejemljiva sol po kateremkoli zahtevku 1 do 4, kjer eden izmed Rg predstavlja metil in vsak naslednji Rg predstavlja vodik.
  8. 8. Spojina ali farmacevtsko sprejemljiva sol po kateremkoli zahtevku 1 do 7, kjer je vsak R3 vodik in R4 je vodik.
  9. 9. Spojina po zahtevku 1, ki je izbrana iz skupine, ki vsebuje: 4-(1-(5 -(4-etilpiperazin-1 -karbonil)piridin-2-il)-5 -hidroksi-1 H-pirazol-4-il)-3 -metilbenzonitril; 4-(5-hidroksi-l-(5-(4-propilpiperazin-l-karbonil)piridin-2-il)-lH-pirazol-4-il)-3- metilbenzonitril; 4-(5 -hidroksi-1 -(5-(4-metil-1,4-diazepan-1 -karbonil)piridin-2-il)-1 H-pirazol-4-il)-3-metilbenzonitril; 4-(5-hidroksi-1 -(5-(4-metilpiperazin-1 -karbonil)piridin-2-il)-1 H-pirazol-4-il)-3 -metilbenzonitril; 4-( 1 -(5 -(4-(tert-butil)piperazin-1 -karbonil)piridin-2-il)-5 -hidroksi-1 H-pirazol-4-il)-3 -metilbenzonitril; 4-(1-(5-(6,6-difluoro-4-metil-l,4-diazepan-l-karbonil)piridin-2-il)-5-hidroksi-1 H-pirazol-4-il)-3 -metilbenzonitril; 4-( 1 -(5 -(4-etilpiperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1 H-pirazol-4-il)-2-fluoro-3-metilbenzonitril; 4-( 1 -(5-(4-etilpiperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1 H-pirazol-4-il)-2-fluoro-5 -metilbenzonitril; 4-( 1 -(5-(4-ciklopropilpiperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1 H-pirazol-4-il)-2-fluoro-3-metilbenzonitril; 4-( 1 -(5-(4-ciklopropilpiperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1 H-pirazol-4-il)-2-fluoro-5-metilbenzonitril; 4-(l -(5-(4-etilpiperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1 H-pirazol-4-il)-2,3-dimetilbenzonitril; 4-( 1 -(5-(4-ciklopropilpiperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1 H-pirazol-4-il)-2,3-dimetilbenzonitril; 4-( 1 -(5-(4-(2,2-difluoroetil)piperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1H-pirazol-4-il)-3-metilbenzonitril; 4-(5-hidroksi-1 -(5-(4-(2,2,2-trifluoroetil)piperazin-1 -karbonil)piridin-2-il)-1H-pirazol-4-il)-3-metilbenzonitril; 2-fluoro-4-(5-hidroksi-l -(5-(4-metilpiperazin-1 -karbonil)piridin-2-il)-1H-pirazol-4-il)-3-metilbenzonitril; 4-(1-(5 -(4-ciklopropil-1,4-diazepan-1 -karbonil)piridin-2-il)-5-hidroksi-1H-pirazol-4-il)-2-fluoro-3-metilbenzonitril; (S)-4-( 1 -(5 -(4-etil-3 -metilpiperazin-1 -karbonil)piridin-2-il)-5 -hidroksi-1H-pirazol-4-il)-2-fluoro-3-metilbenzonitril; 4-( 1 -(5 -(4-etil-3 -metilpiperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1 H-pirazol-4-il)-2-fluoro-3-metilbenzonitril; (S)-4-( 1 -(5-(3,4-dimetilpiperazin-1 -karbonil)piridin-2-il)-5 -hidroksi-1 H-pirazol-4-il)-2-fluoro-3-metilbenzonitril; 4-( 1 -(5-(3,4-dimetilpiperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1 H-pirazol-4-il)-2-fluoro-3-metilbenzonitril; (R)-4-( 1 -(5 -(4-etil-2-metilpiperazin-1 -karbonil)piridin-2-il)-5 -hidroksi-1H-pirazol-4-il)-2-fluoro-3-metilbenzonitril; 4-(1-(5 -(4-etil-2-metilpiperazin-1 -karbonil)piridin-2-il)-5 -hidroksi-1 H-pirazol-4-il)-2-fluoro-3 -metilbenzonitril; (R)-2-fluoro-4-(5-hidroksi-1 -(5-(4-izopropil-3-metilpiperazin-1 -karbonil)piridin-2-il)-1 H-pirazol-4-il)-3-metilbenzonitril; 2-fluoro-4-(5-hidroksi-l-(5-(4-izopropil-3-metilpiperazin-l-karbonil)piridin-2-il)-1 H-pirazol-4-il)-3-metilbenzonitril; (R) -4-( 1 -(5-(4-etil-3-metilpiperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1H-pirazol-4-il)-2-fluoro-3 -metilbenzonitril; (S) -2-fluoro-4-(5-hidroksi-1 -(5 -(4-izopropil-3 -metilpiperazin-1 -karbonil)piridin-2-il)-1 H-pirazol-4-il)-3 -metilbenzonitril; (R) -4-( 1-(5-(3,4-dimetilpiperazin-1 -karbonil)piridin-2-il)-5 -hidroksi-1 H-pirazol-4-il)-2-fluoro-3-metilbenzonitril; (S) -4-( 1 -(5-(4-etil-2-metilpiperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1H-pirazol-4-il)-2-fluoro-3-metilbenzonitril; 4-(5 -hidroksi-1 -(5 -(4-(pentan-3 -il)piperazin-1 -karbonil)piridin-2-il)-1 H-pirazol-4-il)-3 -metilbenzonitril; (S)-4-( 1 -(5 -(4-etil-3 -metilpiperazin-1 -karbonil)piridin-2-il)-5 -hidroksi-1H-pirazol-4-il)-3 -metilbenzonitril; 4-(1-(5 -(4-etil-3 -metilpiperazin-1 -karbonil)piridin-2-il)-5 -hidroksi-1 H-pirazol-4-il)-3 -metilbenzonitril; (S)-4-( 1 -(5-(3,4-dimetilpiperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1 H-pirazol-4-il)-3 -metilbenzonitril; 4-( 1 -(5-(3,4-dimetilpiperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1 H-pirazol-4-il)-3 -metilbenzonitril; 4-( 1 -(5 -(4-ciklobutilpiperazin-1 -karbonil)piridin-2-il)-5 -hidroksi-1 H-pirazol-4-il)-3 -metilbenzonitril; (S)-4-(5-hidroksi-1 -(5-(3-metil-4-propilpiperazin-1 -karbonil)piridin-2-il)-1H-pirazol-4-il)-3 -metilbenzonitril; (R)-4-(5 -hidroksi-1 -(5-(3 -metil-4-propilpiperazin-1 -karbonil)piridin-2-il)-1H-pirazol-4-il)-3 -metilbenzonitril; 4-(5-hidroksi-1 -(5-(3-metil-4-propilpiperazin-l -karbonil)piridin-2-il)-1H-pirazol-4-il)-3 -metilbenzonitril; (R)-4-(l-(5-(4-ciklopropil-3-metilpiperazin-l-karbonil)piridin-2-il)-5-hidroksi-l H-pirazol-4-il)-3 -metilbenzonitril; 4-(l -(5-(4-ciklopropil-3-metilpiperazin-l -karbonil)piridin-2-il)-5-hidroksi-1H-pirazol-4-il)-3 -metilbenzonitril; 4-(5 -hidroksi-1-(5-(3,3,4-trimetilpiperazin-1 -karbonil)piridin-2-il)-1 H-pirazol-4-il)-3 -metilbenzonitril; 4-( 1 -(5-(4-etil-3,3 -dimetilpiperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1H-pirazol-4-il)-3-metilbenzonitril; (R)-4-(5 -hidroksi-1 -(5 -(4-izopropil-3 -metilpiperazin-1 -karbonil)piridin-2-il)-1 H-pirazol-4-il)-3 -metilbenzonitril; 4-(5-hidroksi-1 -(5-(4-izopropil-3-metilpiperazin-1 -karbonil)piridin-2-il)-1H-pirazol-4-il)-3 -metilbenzonitril; (R)-4-( 1 -(5-(2,4-dimetilpiperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1 H-pirazol-4-il)-3-metilbenzonitril; 4-( 1 -(5-(2,4-dimetilpiperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1 H-pirazol-4-il)-3 -metilbenzonitril; (R) -4-( 1 -(5-(4-etil-3-metilpiperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1H-pirazol-4-il)-3-metilbenzonitril; (S) -4-(l-(5-(4-ciklopropil-3-metilpiperazin-l-karbonil)piridin-2-il)-5-hidroksi-1 H-pirazol-4-il)-3 -metilbenzonitril; (S)-4-( 1 -(5-(2,4-dimetilpiperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1 H-pirazol-4-il)-3 -metilbenzonitril; (R) -4-( 1 -(5-(3,4-dimetilpiperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1 H-pirazol-4-il)-3 -metilbenzonitril; (S) -4-(5-hidroksi-1 -(5-(4-izopropil-3-metilpiperazin-1 -karbonil)piridin-2-il)-1H-pirazol-4-il)-3 -metilbenzonitril; (R) -4-( 1 -(5-(4-etil-3 -metilpiperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1H-pirazol-4-il)-2-fluoro-5-metilbenzonitril; 4-(l-(5-(4-etil-3-metilpiperazin-l-karbonil)piridin-2-il)-5-hidroksi-lH-pirazol-4-il)-2-fluoro-5 -metilbenzonitril; 2-fluoro-4-(5-hidroksi-l -(5-(4-metilpiperazin-1 -karbonil)piridin-2-il)-1H-pirazol-4-il)-5-metilbenzonitril; (S) -4-( 1 -(5-(4-etil-3-metilpiperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1H-pirazol-4-il)-2-fluoro-5-metilbenzonitril; (S)-4-( 1 -(5-(3,4-dimetilpiperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1 H-pirazol-4-il)-2-fluoro-5-metilbenzonitril; (R) -4-( 1-(5-(3,4-dimetilpiperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1 H-pirazol-4-il)-2 -fluoro- 5 -metilbenzonitril; 4-(1-(5-(3,4-dimetilpiperazin-1 -karbonil)piridin-2-il)-5 -hidroksi-1 H-pirazol-4-il)-2-fluoro-5-metilbenzonitril; 4-( 1 -(5-(4-ciklopropilpiperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1 H-pirazol-4-il)-3 -metilbenzonitril; 4-(5 -hidroksi-1 -(5 -(4-propilpiperazin-1 -karbonil)piridin-2-il)-1 H-pirazol-4-il)-3 -metilbenzonitril; 4-(5-hidroksi-1 -(5-(4-propil-l ,4-diazepan-1 -karbonil)piridin-2-il)-1 H-pirazol-4-il)-3 -metilbenzonitril; 4-(5-hidroksi-1 -(4-metil-5-(4-metilpiperazin-1 -karbonil)piridin-2-il)-1 H-pirazol-4-il)benzonitril; (S) -4-(l-(5-(4-etil-2-metilpiperazin-l-karbonil)piridin-2-il)-5-hidroksi-lH-pirazol-4-il)-2-fluoro-5-metilbenzonitril; (R)-4-( 1 -(5 -(4-etil-2-metilpiperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1H-pirazol-4-il)-2-fluoro-5-metilbenzonitril; 4-(l -(5-(4-etil-2-metilpiperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1 H-pirazol-4-il)-2-fluoro-5 -metilbenzonitril; (R) -4-( 1 -(5-(4-etil-2-metilpiperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1H-pirazol-4-il)-3 -metilbenzonitril; (S) -4-( 1 -(5 -(4-etil-2-metilpiperazin-1 -karbonil)piridin-2-il)-5 -hidroksi-1H-pirazol-4-il)-3-metilbenzonitril; in 4-( 1 -(5 -(4-etil-2-metilpiperazin-1 -karbonil)piridin-2-il)-5-hidroksi-1 H-pirazol-4-il)-3-metilbenzonitril; in farmacevtsko sprejemljiva sol katerekoli izmed zgoraj navedenih spojin.
  10. 10. Spojina po zahtevku 1, kije 4-(l-(5-(4-etilpiperazin-l-karbonil)piridin-2-il)-5-hidroksi-lH-pirazol-4-il)-3-metilbenzonitril ali njena farmacevtsko sprejemljiva sol.
  11. 11. Spojina po zahtevku 1, ki je 4-(5-hidroksi-l-(5-(4-metilpiperazin-l-karbonil)piridin-2-il)-lH-pirazol-4-il)-3-metilbenzonitril ali njena farmacevtsko sprejemljiva sol.
  12. 12. Spojina po zahtevku 1, kije 4-(1-(5-(4-(2,2-difluoroetil)piperazin-l-karbonil)piridin-2-il)-5-hidroksi-1 H-pirazol-4-il)-3-metilbenzonitril ali njena farmacevtsko sprejemljiva sol.
  13. 13. Spojina po zahtevku 1, kije (S)-4-(l-(5-(3,4-dimetilpiperazin-l-karbonil)piridin-2-il)-5-hidroksi-lH-pirazol-4-il)-3-metilbenzonitril ali njena farmacevtsko sprejemljiva sol.
  14. 14. Spojina po zahtevku 1, kije (R)-4-(l-(5-(2,4-dimetilpiperazin-l-karbonil)piridin-2-il)-5-hidroksi-lH-pirazol-4-il)-3-metilbenzonitril ali njena farmacevtsko sprejemljiva sol.
  15. 15. Spojina po zahtevku 1, kije (R)-4-( 1-(5-(3,4-dimetilpiperazin-1-karbonil)piridin-2-il)-5-hidroksi-1 H-pirazol-4-il)-3-metilbenzonitril ali njena farmacevtsko sprejemljiva sol.
  16. 16. Farmacevtski sestavek, ki vsebuje spojino ali farmacevtsko sprejemljivo sol, kot je opisano v kateremkoli zahtevku od 1 do 15 in farmacevtsko sprejemljiv ekscipient.
  17. 17. Spojina ali farmacevtsko sprejemljiva sol po kateremkoli zahtevku 1 do 15, za uporabo kot zdravilo.
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PE20151860A1 (es) 2015-12-16
NZ711522A (en) 2021-02-26
US20170275271A1 (en) 2017-09-28
JP6874114B2 (ja) 2021-05-19
US20150224113A1 (en) 2015-08-13
LT2978752T (lt) 2018-03-26
EA031647B1 (ru) 2019-02-28
IL240803B (en) 2019-02-28
US9040522B2 (en) 2015-05-26
PH12015502248B1 (en) 2016-02-01
EP3336084B1 (en) 2021-03-17
ECSP15045801A (es) 2017-02-24
BR112015020350B1 (pt) 2023-04-25
JP6462911B2 (ja) 2019-01-30
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KR102376354B1 (ko) 2022-04-04
TW201446752A (zh) 2014-12-16
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US20180186772A1 (en) 2018-07-05
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PL2978752T3 (pl) 2018-06-29
PH12015502248A1 (en) 2016-02-01
KR20150135794A (ko) 2015-12-03
US20160251337A1 (en) 2016-09-01
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SG11201506749XA (en) 2015-09-29
AP2015008783A0 (en) 2015-10-31
PT2978752T (pt) 2018-03-09
RS56974B1 (sr) 2018-05-31
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