HRP20170277T1 - N-cijanometilamidi kao inhibitori janus kinaze - Google Patents

N-cijanometilamidi kao inhibitori janus kinaze Download PDF

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HRP20170277T1
HRP20170277T1 HRP20170277TT HRP20170277T HRP20170277T1 HR P20170277 T1 HRP20170277 T1 HR P20170277T1 HR P20170277T T HRP20170277T T HR P20170277TT HR P20170277 T HRP20170277 T HR P20170277T HR P20170277 T1 HRP20170277 T1 HR P20170277T1
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benzamide
phenyl
amino
cyanomethyl
pyrimidin
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HRP20170277TT
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Ranjit C. Desai
Jigar Desai
Pankaj Patel
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Cadila Healthcare Limited
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Claims (11)

1. Spoj sa strukturom opće formule (I) [image] ili njegove farmaceutski prikladne soli Gdje X se pri svakom pojavljivanju nezavisno odabire između N ili CH; Z se pri svakom pojavljivanju nezavisno odabire između N ili CH; n se odabire između 0,1. A se nezavisno odabire između vodika, halogena, C1-4 alkil, CF3, CN, CON(R1)2, OC1-4alkil Prsten B se odabire između sljedećih prstenastih sustava, od kojih svaki može biti supstituiran [image]
2. Spojevi prema zahtjevu 1 gdje se supstituenti na prstenu B, uvijek kada je primjenjivo, nezaviso odabiru između H, OH, CN, NH2, halogen, okso, OCF3, CF3, C1-C6 alkil, OC1-C6 alkil, (CH2)1-6OC1-C6 alkil, O-(CH2)0-4OC1-C6 alkil, C(O)NHC1-C6 alkil, NHC(O)C1-C6 alkil, S(O)0-2C1-C6 alkil, (CH2)1-6N(R1)2, (CH2)1-6NHC(=O)OR1, (CH2)1-6NHC(=O)R1, C(=O)OR1, C(=O)R1, (CH2)1-4C(=O) NHR1, (CH2)0-4O(CH2)0-4Ar1, (CH2)0-4NH(CH2)0-4Ar1, (CH2)0-4 Ar1, (CH2)0-4C(O)(CH2)0-4Ar1, (CH2)0-4C(=O) O(CH2)0-4Ar1, (CH2)0-4C(=O)NR1(CH2)0-4Ar1.
3. Spoj prema zahtjevu 1 i 2 gdje se R1 pri svakom pojavljivanju nezavisno odabire između vodika, C1-C4 alkil, C1-C4 haloalkil, C3-C7 cikloalkil skupina.
4. Spoj prema zahtjevu 2 gdje se Ar1 pri svakom pojavljivanju nezavisno odabire između nesupstituiranih ili supstituiranih aril ili heterocikličkih prstenova supstituiranih s jednim, dva, tri ili četiri supstituenta.
5. Spojevi prema zahtjevu 4 gdje se supstituenti na Ar1 nezavisno odabiru iz grupe koju čine OH, CN, NH2, halogen, OCF3, CF3, C1-C6 alkil, OC1-C6alkil, (CH2)1-6OC1-C6 alkil, O-(CH2)0-4OC1-C6 alkil, C(O)NHC1-C6 alkil, NHC(O)C1-C6 alkil, S(O)0-2C1-C6 alkil, (CH2)1-6N(R1)2, (CH2)1-6NHC(=O)OR1, (CH2)1-6NHC(=O)R1, C(=O)OR1 ili -C(=O)R1, CH2(CH2)0-4C(=O)NHR1.
6. Spoj prema zahtjevu 1 odabran iz grupe koju čine: N-(Cijanometil)-4-(2-((4-(4-(2-oksopirolidin-1-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(1,1-dioksidoizotiazolidin-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-morfolinopiperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; 4-(2-((4-(4-(1H-1,2,4-Triazol-1-il)piperidin-1-il)fenil)amino)pirimidin-4-il)-N-(cijanometil)benzamid; 4-(2-((4-(4-(1H-Pirazol-1-il)piperidin-1-il)fenil)amino)pirimidin-4-il)-N-(cijanometil)benzamid; 4-(2-((4-([1,3’-Bipirolidin]-1’-il)fenil)amino)pirimidin-4-il)-N-(cijanometil) benzamid; N-(cijanometil)-4-(2-((4-(4-(1,1-dioksidotetrahidro-2H-tiopiran-4-il)piperazin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(furan-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(1,1-dioksidotetrahidrotiofen-3-il)piperazin-1-il)fenil)amino)pirimidin-4- il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(2,5-dioksopirolidin-1-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(tiofen-2-il)piperidin-1-il)fenil)amino) pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(2-oksooksazolidin-3-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(tetrahidrofuran-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(5-metilfuran-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(tetrahidro-2H-piran-4-il)piperazin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(5-metiltetrahidrofuran-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; 4-(2-((4-(4-(6-Oksa-3-azabiciklo[3.1.1]heptan-3-il)piperidin-1-il)fenil)amino)pirimidin-4-il)-N-(cijanometil)benzamid; N-(Cijanometil)-4-(2-((4-(4-(2-oksoimidazolidin-1-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; 4-(2-((4-(4-(1,3,4-Oksadiazol-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)-N-(cijanometil)benzamid; 4-(2-((4-(4-(2H-1,2,3-Triazol-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)-N-(cijanometil) benzamid; 4-(2-((4-(4-(1H-1,2,3-Triazol-1-il)piperidin-1-il)fenil)amino)pirimidin-4-il)-N-(cijano metil)benzamid; N-(Cijanometil)-4-(2-((4-(4-(5-okso-1H-1,2,4-triazol-4(SH)-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(5-okso-4,5-dihidro-1H-1,2,4-triazol-1-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; 4-(2-((4-(4-(1-Oksa-8-azaspiro[4.5]dekan-8-il)piperidin-1-il)fenil)amino)pirimidin-4-il)-N-(cijanometil)benzamid; N-(Cijanometil)-4-(2-((4-(4-(5-metil-1,3,4-oksadiazol-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(5-metil-1,3,4-tiadiazol-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(tetrahidro-2H-[1,4]dioksino[2,3-c]pirol-6(3H)-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(2-okso-1-oksa-8-azaspiro[4.5]dekan-8-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(5-okso-4,5-dihidro-1,3,4-oksadiazol-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(4-ciklopropil-5-metil-4H-1,2,4-triazol-3-il)piperidin-1-il)fenil) amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(5-metoksi-1,3,4-oksadiazol-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; 4-(2-((4-(4-(1,4-Dioksepan-6-il)piperazin-1-il)fenil)amino)pirimidin-4-il)-N-(cijanometil)benzamid; N-(Cijanometil)-4-(2-((4-(4-(4,5-dihidro-1H-imidazol-2-il)piperazin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(4,5-dihidro-1H-imidazol-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(3-(tetrahidro-2H-[1,4]dioksino[2,3-c]pirol-6(3H)-il)pirolidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(5-metil-1,3,4-oksadiazol-2-il)piperazin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(3,4-dihidroksipirolidin-1-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; 4-(2-((4-(4-(8-Oksa-3-azabiciklo[3.2.1]oktan-3-il)piperidin-1-il)fenil)amino)pirimidin-4-il)-N-(cijanometil)benzamid; 4-(2-((4-(4-(6-Acetil-3,6-diazabiciklo[3.1.1]heptan-3-il)piperidin-1-il)fenil)amino)pirimidin-4-il)-N-(cijanometil)benzamid; N-(Cijanometil)-4-(5-metil-2-((4-(4-morfolinopiperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(5-metil-2-((4-(4-(2-oksopirolidin-1-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; 4-(2-((4-(4-(1-Oksa-8-azaspiro[4.5]dekan-8-il)piperidin-1-il)fenil)amino)-5-metilpirimidin-4-il)-N-(cijanometil)benzamid; N-(Cijanometil)-4-(5-metil-2-((4-(4-(5-metil-1,3,4-oksadiazol-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(5-fluoro-2-((4-(4-morfolinopiperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; 4-(5-Kloro-2-((4-(4-morfolinopiperidin-1-il)fenil)amino)pirimidin-4-il)-N-(cijanometil)benzamid; N-(Cijanometil)-4-(5-fluoro-2-((4-(4-(2-oksopirolidin-1-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; 4-(5-Kloro-2-((4-(4-(2-oksopirolidin-1-il)piperidin-1-il)fenil)amino)pirimidin-4-il)-N-(cijanometil)benzamid; 4-(2-((4-(4-(6-Oksa-3-azabiciklo[3.1.1]heptan-3-il)piperidin-1-il)fenil)amino)-5-metilpirimidin-4-il)-N-(cijanometil)benzamid; 4-(2-((4-(4-(6-Oksa-3-azabiciklo[3.1.1]heptan-3-il)piperidin-1-il)fenil)amino)-5-fluoropirimidin-4-il)-N-(cijanometil)benzamid; -(2-((4-(4-(6-Oksa-3-azabiciklo[3.1.1]heptan-3-il)piperidin-1-il)fenil)amino)-5-kloropirimidin-4-il)-N-(cijanometil)benzamid; N-(Cijanometil)-4-(5-metil-2-((4-(4-(tetrahidro-2H-[1,4]dioksino[2,3-c]pirol-6(3H)-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(5-fluoro-2-((4-(4-(tetrahidro-2H-[1,4]dioksino[2,3-c]pirol-6(3H)-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; 4-(5-Kloro-2-((4-(4-(tetrahidro-2H-[1,4]dioksino[2,3-c]pirol-6(3H)-il)piperidin-1-il)fenil)amino)pirimidin-4-il)-N-(cijanometil)benzamid; N-(Cijanometil)-4-(5-fluoro-2-((4-(4-(5-metil-1,3,4-oksadiazol-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; 4-(5-Kloro-2-((4-(4-(5-metil-1,3,4-oksadiazol-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)-N-(cijanometil)benzamid; N-(Cijanometil)-4-(5-metil-2-((4-(4-(5-metil-1,3,4-oksadiazol-2-il)piperazin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(5-fluoro-2-((4-(4-(5-metil-1,3,4-oksadiazol-2-il)piperazin-1-il)fenil)amino)pirimidin-4-il)benzamid; 4-(5-Kloro-2-((4-(4-(5-metil-1,3,4-oksadiazol-2-il)piperazin-1-il)fenil)amino)pirimidin-4-il)-N-(cijanometil)benzamid; 4-(2-((4-(4-(3-Tia-6-azabiciklo[3.1.1]heptan-6-il)piperidin-1-il)fenil)amino)pirimidin-4-il)-N-(cijanometil)benzamid; 4-(2-((4-(4-(3-Tia-6-azabiciklo[3.1.1]heptan-6-il)piperidin-1-il)fenil)amino)-5-metilpirimidin-4-il)-N-(cijanometil)benzamid; 4-(2-((4-(4-(3-Tia-6-azabiciklo[3.1.1]heptan-6-il)piperidin-1-il)fenil)amino)-5-fluoropirimidin-4-il)-N-(cijanometil)benzamid; 4-(2-((4-(4-(3-Tia-6-azabiciklo[3.1.1]heptan-6-il)piperidin-1-il)fenil)amino)-5-kloropirimidin-4-il)-N-(cijanometil)benzamid;
7. Spoj prema bilo kojem od prethodnih zahtjeva odabran iz grupe koju čine: N-(Cijanometil)-4-(2-((4-(4-(2-oksopirolidin-1-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(1,1-dioksidoizotiazolidin-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-morfolinopiperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; 4-(2-((4-(4-(1H-1,2,4-Triazol-1-il)piperidin-1-il)fenil)amino)pirimidin-4-il)-N-(cijanometil)benzamid; 4-(2-(4-((4-(1H-Pirazol-1-il)piperidin-1-il)fenil)amino)pirimidin-4-il)-N-(cijanometil)benzamid; 4-(2-((4-([1,3’-Bipirolidin]-1’-il)fenil)amino)pirimidin-4-il)-N-(cijanometil) benzamid; N-(cijanometil)-4-(2-((4-(4-(1,1-dioksidotetrahidro-2H-tiopiran-4-il)piperazin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(furan-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(1,1-dioksidotetrahidrotiofen-3-il)piperazin-1-il)fenil)amino)pirimidin-4- il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(2,5-dioksopirolidin-1-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(tiofen-2-il)piperidin-1-il)fenil)amino) pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(2-oksooksazolidin-3-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(tetrahidrofuran-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(5-metilfuran-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(tetrahidro-2H-piran-4-il)piperazin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(5-metiltetrahidrofuran-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; 4-(2-((4-(4-(6-Oksa-3-azabiciklo[3.1.1]heptan-3-il)piperidin-1-il)fenil)amino)pirimidin-4-il)-N-(cijanometil)benzamid; N-(Cijanometil)-4-(2-((4-(4-(2-oksoimidazolidin-1-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; 4-(2-((4-(4-(1,3,4-Oksadiazol-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)-N-cijanometil)benzamid; 4-(2-((4-(4-(2H-1,2,3-Triazol-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)-N-(cijanometil)benzamid; 4-(2-((4-(4-(1H-1,2,3-Triazol-1-il)piperidin-1-il)fenil)amino)pirimidin-4-il)-N-(cijanometil)benzamid; N-(Cijanometil)-4-(2-((4-(4-(5-okso-1H-1,2,4-triazol-4(SH)-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(5-okso-4,5-dihidro-1H-1,2,4-triazol-1-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; 4-(2-((4-(4-(1-Oksa-8-azaspiro[4.5]dekan-8-il)piperidin-1-il)fenil)amino)pirimidin-4-il)-N-(cijanometil)benzamid; N-(Cijanometil)-4-(2-((4-(4-(5-metil-1,3,4-oksadiazol-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(5-metil-1,3,4-tiadiazol-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(tetrahidro-2H-[1,4]dioksino[2,3-c]pirol-6(3H)-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(2-okso-1-oksa-8-azaspiro[4.5]dekan-8-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(5-okso-4,5-dihidro-1,3,4-oksadiazol-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(4-ciklopropil-5-metil-4H-1,2,4-triazol-3-il)piperidin-1-il)fenil) amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(5-metoksi-1,3,4-oksadiazol-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; 4-(2-((4-(4-(1,4-Dioksepan-6-il)piperazin-1-il)fenil)amino)pirimidin-4-il)-N-(cijanometil) benzamid; N-(Cijanometil)-4-(2-((4-(4-(4,5-dihidro-1H-imidazol-2-il)piperazin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(4,5-dihidro-1H-imidazol-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(3-(tetrahidro-2H-[1,4]dioksino[2,3-c]pirol-6(3H)-il)pirolidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(5-metil-1,3,4-oksadiazol-2-il)piperazin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(2-((4-(4-(3,4-dihidroksipirolidin-1-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; 4-(2-((4-(4-(8-Oksa-3-azabiciklo[3.2.1]octan-3-il)piperidin-1-il)fenil)amino)pirimidin-4-il)-N-(cijanometil)benzamid; 4-(2-((4-(4-(6-Acetil-3,6-diazabiciklo[3.1.1]heptan-3-il)piperidin-1-il)fenil)amino)pirimidin-4-il)-N-(cijanometil)benzamid; N-(Cijanometil)-4-(5-metil-2-((4-(4-morfolinopiperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(5-metil-2-((4-(4-(2-oksopirolidin-1-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; 4-(2-((4-(4-(1-Oksa-8-azaspiro[4.5]dekan-8-il)piperidin-1-il)fenil)amino)-5-metilpirimidin-4-il)-N-(cijanometil)benzamid; N-(Cijanometil)-4-(5-metil-2-((4-(4-(5-metil-1,3,4-oksadiazol-2-il)piperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; N-(Cijanometil)-4-(5-fluoro-2-((4-(4-morfolinopiperidin-1-il)fenil)amino)pirimidin-4-il)benzamid; 4-(5-Kloro-2-((4-(4-morfolinopiperidin-1-il)fenil)amino)pirimidin-4-il)-N-(cijanometil)benzamid;
8. Farmaceutski pripravak koji sadrži terapijski učinkovitu količinu spoja Formule (I) prema bilo kojem od prethodnih zahtjeva i po izboru jedan ili više farmaceutski prikladnih nosača, punila ili pomoćnih tvari.
9. Spojevi prema bilo kojem od prethodnih zahtjeva za uporabu u liječenju upalnih stanja, autoimunih bolesti, proliferativnih bolesti, alergije i odbacivanja transplantata, bolesti koje obuhvaćaju poremećaj obnavljanja hrskavice, kongenitalnih malformacija hrskavice i/ili bolesti povezanih s hipersekrecijom IL6 ili interferona gdje JAK kinaza ima patofiziološku ulogu.
10. Farmaceutski pripravak koji sadrži spojeve formule 1 prema zahtjevu 1 zajedno s prikladnim pomoćnim tvarima, pogodan za liječenje upalnih stanja, autoimunih bolesti, proliferativnih bolesti, alergije i odbacivanja transplantata, bolesti koje obuhvaćaju poremećaj obnavljanja hrskavice, kongenitalnih malformacija hrskavice i/ili bolesti povezanih s hipersekrecijom IL6 ili interferona.
11. Međuspoj formule 4 [image] gdje su B, Z, X, n i A prema zahtjevu 1.
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