HRP20151002T1 - 5-anilinoimidazopiridini i postupci njihove uporabe - Google Patents

5-anilinoimidazopiridini i postupci njihove uporabe Download PDF

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HRP20151002T1
HRP20151002T1 HRP20151002TT HRP20151002T HRP20151002T1 HR P20151002 T1 HRP20151002 T1 HR P20151002T1 HR P20151002T T HRP20151002T T HR P20151002TT HR P20151002 T HRP20151002 T HR P20151002T HR P20151002 T1 HRP20151002 T1 HR P20151002T1
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cr14r15
cr19r20
imidazo
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Stephen Price
Robert Heald
Wendy Lee
Mark E. Zak
Joanne Frances Mary Hewitt
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Genentech, Inc.
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    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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Claims (12)

1. Spoj, naznačen time, da se upotrebljava u postupku liječenja raka, pri čemu je odabran od sljedećih: 5-(2-fluoro-4-jodofenilamino)-imidazo[1,5-a]piridin-6-karboksilna kiselina-(2-hidroksietoksi)-amid; 5-(2-fluoro-4-jodofenilamino)-imidazo[1,5-a]piridin-6-karboksilna kiselina-((R)-2,3-dihidroksi-propoksi)-amid; 5-(2-fluoro-4-jodofenilamino)-imidazo[1,5-a]piridin-6-karboksilna kiselina-((S)-2-hidroksi-propoksi)-amid; 5-(4-bromo-2-fluorofenilamino)-imidazo[1,5-a]piridin-6-karboksilna kiselina-(2-hidroksietoksi)-amid; 5-(4-bromo-2-fluorofenilamino)-imidazo[1,5-a]piridin-6-karboksilna kiselina-((S)-2-hidroksi-propoksi)-amid; 5-(4-bromo-2-fluorofenilamino)-8-fluoro-imidazo[1,5-a]piridin-6-karboksilna kiselina- ((S)-2-hidroksi-propoksi)-amid; 8-fluoro-5-(2-fluoro-4-jodofenilamino)-imidazo[1,5-a]piridin-6-karboksilna kiselina-(2-hidroksi-etoksi)-amid; 8-fluoro-5-(2-fluoro-4-jodofenilamino)-imidazo[1,5-a]piridin-6-karboksilna kiselina-((R)-2,3-dihidroksi-propoksi)-amid; 8-fluoro-5-(2-fluoro-4-jodofenilamino)-imidazo[1,5-a]piridin-6-karboksilna kiselina-((S)-2-hidroksi-propoksi)-amid; 5-(2-fluoro-metansulfanil-fenilamino)-imidazo[1,5-a]piridin-6-karboksilna kiselina-(2-hidroksi-etoksi)-amid; 5-(2-fluoro-4-jodofenilamino)-imidazo[1,5-a]pirazin-6-karboksilna kiselina-(2-hidroksi-etoksi)-amid; 5-(2-fluoro-4-jodofenilamino)-imidazo[1,5-a]pirazin-6-karboksilna kiselina-((S)-2-hidroksi-propoksi)-amid; 5-(4-ciklopropil-2-fluorofenilamino)-imidazo[1,5-a]piridin-6-karboksilna kiselina-(2-hidroksi-etoksi)-amid; (R)-N-(2,3-dihidroksipropoksi)-5-(2-fluoro-4-jodofenilamino)-imidazo[1,5-a]pirazin-6-karboksamid; N-etoksi-5-(2-fluoro-4-jodofenilamino)-imidazo[1,5-a]pirazin-6-karboksamid; N-(ciklopropilmetoksi)-5-(2-fluoro-4-jodofenilamino)-imidazo[1,5-a]pirazin-6-karboksamid; 5-(2-fluoro-4-jodofenilamino)-N-metil-imidazo[1,5-a]pirazin-6-karboksamid; 5-(4-bromo-2-fluorofenilamino)-N-(2-hidroksi-etoksi)-imidazo[1,5-a]pirazin-6-karboksamid; (S)-5-(4-bromo-2-fluorofenilamino)-N-(2-hidroksi-propoksi)-imidazo[1,5-a]pirazin-6-karboksamid; (R)-5-(4-bromo-2-fluorofenilamino)-N-(2,3-dihidroksi-propoksi)-imidazo[1,5-a]pirazin-6-karboksamid; i 5-(4-bromo-2-fluorofenilamino)-N-(ciklopropil-metoksi)-imidazo[1,5-a]pirazin-6-karboksamid; ili njegova farmaceutski prihvatljiva sol; pri čemu postupak obuhvaća primjenu spoja u kombinaciji s gemcitabinom ili taksoidom.
2. Spoj za uporabu u postupku liječenja raka prema zahtjevu 1, naznačen time, da spoj je 5-(2-fluoro-4-jodofenilamino)-imidazo[1,5-a]piridin-6-karboksilna kiselina-(2-hidroksietoksi)-amid, ili njegova farmaceutski prihvatljiva sol.
3. Spoj za uporabu u postupku liječenja raka prema zahtjevu 1 ili zahtjevu 2, naznačen time, da rak je rak gušterače, rak nemalih stanica pluća, kolorektalni rak, endometrijski rak, rak jajnika ili maligni melanom.
4. Spoj za uporabu u postupku liječenja raka prema bilo kojem od zahtjeva 1 do 3, naznačen time, da se spoj primjenjuje istovremeno s taksoidom ili gemcitabinom.
5. Spoj za uporabu u postupku liječenja raka prema bilo kojem od zahtjeva 1 do 3, naznačen time, da se spoj primjenjuje uzastopno nakon taksoida ili gemcitabina.
6. Spoj za uporabu u postupku liječenja raka prema bilo kojem od zahtjeva 1 do 3, naznačen time, da se spoj primjenjuje odvojeno od taksoida ili gemcitabina.
7. Spoj za uporabu u postupku liječenja raka prema bilo kojem od prethodnih zahtjeva, naznačen time, da taksoid je paklitaksel.
8. Spoj za uporabu u postupku liječenja raka prema bilo kojem od prethodnih zahtjeva, naznačen time, da je liječenje za oralnu primjenu.
9. Spoj za uporabu u postupku liječenja raka prema bilo kojem od zahtjeva 1 do 3, naznačen time, da se spoj primjenjuje u kombinaciji s gemcitabinom za liječenje raka gušterače.
10. Spoj za uporabu u postupku liječenja raka prema bilo kojem od zahtjeva 1 do 3, naznačen time, da se spoj primjenjuje u kombinaciji s paklitakselom za liječenje raka nemalih stanica pluća ili raka jajnika.
11. Spoj, naznačen time, da se upotrebljava u postupku liječenja raka ili upalnog poremećaja, kojemu je svojstvena mutacija ili prekomjerna ekspresija MEK-kinaze, pri čemu je spoj odabran od sljedećih: 5-(2-fluoro-4-jodofenilamino)-imidazo[1,5-a]piridin-6-karboksilna kiselina-(2-hidroksietoksi)-amid; 5-(2-fluoro-4-jodofenilamino)-imidazo[1,5-a]piridin-6-karboksilna kiselina-((R)-2,3-dihidroksi-propoksi)-amid; 5-(2-fluoro-4-jodofenilamino)-imidazo[1,5-a]piridin-6-karboksilna kiselina-((S)-2-hidroksi-propoksi)-amid; 5-(4-bromo-2-fluorofenilamino)-imidazo[1,5-a]piridin-6-karboksilna kiselina-(2-hidroksietoksi)-amid; 5-(4-bromo-2-fluoro-fenilamino)-imidazo[1,5-a]piridin-6-karboksilna kiselina-((S)-2-hidroksi-propoksi)-amid; 5-(4-bromo-2-fluoro-fenilamino)-8-fluoro-imidazo[1,5-a]piridin-6-karboksilna kiselina-((S)-2-hidroksi-propoksi)-amid; 8-fluoro-5-(2-fluoro-4-jodofenilamino)-imidazo[1,5-a]piridin-6-karboksilna kiselina-(2-hidroksi-etoksi)-amid; 8-fluoro-5-(2-fluoro-4-jodofenilamino)-imidazo[1,5-a]piridin-6-karboksilna kiselina-((R)-2,3-dihidroksi-propoksi)-amid; 8-fluoro-5-(2-fluoro-4-jodofenilamino)-imidazo[1,5-a]piridin-6-karboksilna kiselina-((S)-2-hidroksi-propoksi)-amid; 5-(2-fluoro-metansulfanil-fenilamino)-imidazo[1,5-a]piridin-6-karboksilna kiselina-(2-hidroksi-etoksi)-amid; 5-(2-fluoro-4-jodofenilamino)-imidazo[1,5-a]pirazin-6-karboksilna kiselina-(2-hidroksi-etoksi)-amid; 5-(2-fluoro-4-jodofenilamino)-imidazo[1,5-a]pirazin-6-karboksilna kiselina-((S)-2-hidroksi-propoksi)-amid; 5-(4-ciklopropil-2-fluorofenilamino)-imidazo[1,5-a]piridin-6-karboksilna kiselina-(2-hidroksi-etoksi)-amid; (R)-N-(2,3-dihidroksipropoksi)-5-(2-fluoro-4-jodofenilamino)-imidazo[1,5-a]pirazin-6-karboksamid; N-etoksi-5-(2-fluoro-4-jodofenilamino)-imidazo[1,5-a]pirazin-6-karboksamid; N-(ciklopropilmetoksi)-5-(2-fluoro-4-jodofenilamino)-imidazo[1,5-a]pirazin-6-karboksamid; 5-(2-fluoro-4-jodofenilamino)-N-metil-imidazo[1,5-a]pirazin-6-karboksamid; 5-(4-bromo-2-fluorofenilamino)-N-(2-hidroksi-etoksi)-imidazo[1,5-a]pirazin-6-karboksamid; (S)-5-(4-bromo-2-fluorofenilamino)-N-(2-hidroksi-propoksi)-imidazo[1,5-a]pirazin-6-karboksamid; (R)-5-(4-bromo-2-fluorofenilamino)-N-(2,3-dihidroksi-propoksi)-imidazo[1,5-a]pirazin-6-karboksamid; i 5-(4-bromo-2-fluorofenilamino)-N-(ciklopropil-metoksi)-imidazo[1,5-a]pirazin-6-karboksamid; ili njegova farmaceutski prihvatljiva sol.
12. Spoj, naznačen time, da je predstavljen sljedećom formulom I, i njegove soli, te time da se upotrebljava u postupku liječenja upalnog poremećaja: [image] gdje: Z1 je CR1 ili N; R1 je H, C1-C3-alkil, halo, CF3, CHF2, CN, ORA ili NRARA; R1’ je H, C1-C3-alkil, halo, CF3, CHF2, CN, ORA ili NRARA; pri čemu je svaki RA neovisno H ili C1-C3-alkil; Z2 je CR2 ili N; Z3 je CR3 ili N; pod uvjetom da samo jedan od Z1, Z2 i Z3 može biti istovremeno N; R2 i R3 su neovisno odabrani od sljedećih: H, halo, CN, CF3, -OCF3, -NO2, -(CR14R15)nC(=Y’)R11, -(CR14R15)nC(=Y’)OR11, -(CR14R15)nC(=Y’)NR11R12, -(CR14R15)nNR11R12, -(CR14R15)nOR11, -(CR14R15)nSR11, -(CR14R15)nNR12C(=Y’)R11, -(CR14R15)nNR12C(=Y’)OR11, -(CR14R15)nNR13C(=Y’)NR11R12, -(CR14R15)nNR12SO2R11, -(CR14R15)nOC(=Y’)R11, -(CR14R15)nOC(=Y’)OR11, -(CR14R15)nOC(=Y’)NR11R12, -(CR14R15)nOS(O)2(OR11), -(CR14R15)nOP(=Y’)(OR11)(OR12), -(CR14R15)nOP(OR11)(OR12), -(CR14R15)nS(O)R11, -(CR14R15)nS(O)2R11, -(CR14R15)nS(O)2NR11R12, -(CR14R15)nS(O)(OR11), -(CR14R15)nS(O)2(OR11), -(CR14R15)nSC(=Y’)R11, -(CR14R15)nSC(=Y’)OR11, -(CR14R15)nSC(=Y’)NR11R12, C1-C12-alkil, C2-C8-alkenil, C2-C8-alkinil, karbociklil, heterociklil, aril i heteroaril; R4 je H, C1-C6-alkil ili C3-C4-karbociklil; Y je W-C(O)- ili W’; W je [image] ili [image] R5 je H ili C1-C12-alkil; X1 je odabran od R11’ i -OR11’; kada X1 je R11’, tada se X1 po želji uzima zajedno s R5 i atomom dušika na kojega su vezani, za tvorbu 4-7-članog zasićenog ili nezasićenog prstena koji ima od 0 do 2 dodatna heteroatoma odabrana od O, S i N, pri čemu je navedeni prsten po želji supstituiran s jednom ili više skupina odabranih od sljedećih: halo, CN, CF3, -OCF3, -NO2, okso, -(CR19R20)nC(=Y’)R16, -(CR19R20)nC(=Y’)OR16, -(CR19R20)nC(=Y’)NR16R17, -(CR19R20)nNR16R17, -(CR19R20)nOR16, -(CR19R20)n-SR16, -(CR19R20)nNR16C(=Y’)R17, -(CR19R20)nNR16C(=Y’)OR17, -(CR19R20)nNR18C(=Y’)NR16R17, -(CR19R20)nNR17SO2R16, -(CR19R20)nOC(=Y’)R16, -(CR19R20)nOC(=Y’)OR16, -(CR19R20)nOC(=Y’)NR16R17, -(CR19R20)nOS(O)2(OR16), -(CR19R20)nOP(=Y’)(OR16)(OR17), -(CR19R20)nOP(OR16)(OR17), -(CR19R20)nS(O)R16, -(CR19R21)nS(O)2R16, -(CR19R20)nS(O)2NR16R17, -(CR19R20)nS(O)(OR16), -(CR19R20)nS(O)2(OR16), -(CR19R20)nSC(=Y’)R16, -(CR19R20)nSC(=Y’)OR16, -(CR19R20)nSC(=Y’)NR16R17 i R21; svaki R11’ je neovisno H, C1-C12-alkil, C2-C8-alkenil, C2-C8-alkinil, karbociklil, heterociklil, aril ili heteroaril; R11, R12 i R13 su neovisno H, C1-C12-alkil, C2-C8-alkenil, C2-C8-alkinil, karbociklil, heterociklil, aril ili heteroaril; ili R11 i R12 zajedno s dušikom na kojega su priključeni, tvore 3-8-člani zasićeni, nezasićeni ili aromatski prsten koji ima od 0 do 2 heteroatoma odabranih od O, S i N, pri čemu je spomenuti prsten po želji supstituiran s jednom ili više skupina odabranih od sljedećih: halo, CN, CF3, -OCF3, -NO2, C1-C6-alkil, -OH, -SH, -O(C1-C6-alkil), -S(C1-C6-alkil), -NH2, -NH(C1-C6-alkil), -N(C1-C6-alkil)2, -SO2(C1-C6-alkil), -CO2H, -CO2(C1-C6-alkil), -C(O)NH2, -C(O)NH(C1-C6-alkil), -C(O)N(C1-C6-alkil)2, -N(C1-C6-alkil)C(O)(C1-C6-alkil), -NHC(O)(C1-C6-alkil), -NHSO(C1-C6-alkil), -N(C1-C6-alkil)SO2(C1-C6-alkil), -SO2NH2, -SO2NH(C1-C6-alkil), -SO2N(C1-C6-alkil)2, -OC(O)NH2, -OC(O)NH(C1-C6-alkil), -OC(O)N(C1-C6-alkil)2, -OC(O)O(C1-C6-alkil), -NHC(O)NH(C1-C6-alkil), -NHC(O)N(C1-C6-alkil)2, -N(C1-C6-alkil)C(O)NH(C1-C6-alkil), -N(C1-C6-alkil)C(O)N(C1-C6-alkil)2, -NHC(O)NH(C1-C6-alkil), -NHC(O)N(C1-C6-alkil)2, -NHC(O)O(C1-C6 alkil), i -N(C1-C6-alkil)C(O)O(C1-C6-alkil); R14 i R15 su neovisno odabrani od H, C1-C12-alkila, arila, karbociklila, heterociklila, i heteroarila; W’ je [image] gdje [image] je [image] [image] svaki X2 je neovisno O, S, ili NR9; svaki R7 je neovisno odabran od sljedećih: H, halo, CN, CF3, -OCF3, -NO2, -(CR14R15)nC(=Y’)R11, -(CR14R15)nC(=Y’)OR11, -(CR14R15)nC(=Y’)NR11R12, -(CR14R15)nNR11R12, -(CR14R15)nOR11, -(CR14R15)nSR11, -(CR14R15)nNR12C(=Y’)R11, -(CR14R15)nNR12C(=Y’)OR11, -(CR14R15)nNR13C(=Y’)NR11R12, -(CR14R15)nNR12SO2R11, -(CR14R15)nOC(=Y’)R11, -(CR14R15)nOC(=Y’)OR11, -(CR14R15)nOC(=Y’)NR11R12, -(CR14R15)nOS(O)2(OR11), -(CR14R15)nOP(=Y’)(OR11)(OR12), -(CR14R15)nOP(OR11)(OR12), -(CR14R15)nS(O)R11, -(CR14R15)nS(O)2R11, -(CR14R15)nS(O)2NR11R12, -(CR14R15)nS(O)(OR11), -(CR14R15)nS(O)2(OR11), -(CR14R15)nSC(=Y’)R11, -(CR14R15)nSC(=Y’)OR11, -(CR14R15)nSC(=Y’)NR11R12, C1-C12-alkil, C2-C8-alkenil, C2-C8-alkinil, karbociklil, heterociklil, aril i heteroaril; svaki R8 je neovisno odabran od C1-C12-alkila, arila, karbociklila, heterociklila i heteroarila; R9 je odabran od sljedećih: H, -(CR14R15)nC(=Y’)R11, -(CR14R15)nC(=Y’)OR11, -(CR14R15)nC(=Y’)NR11R12, -(CR14R15)qNR11R12, -(CR14R15)qOR11, -(CR14R15)qSR11, -(CR14R15)qNR12C(=Y’)R11, -(CR14R15)qNR12C(=Y)OR11, -(CR14R15)qNR13C(=Y’)NR11R12, -(CR14R15)qNR12SO2R11, -(CR14R15)qOC(=Y’)R11, -(CR14R15)qOC(=Y’)OR11, -(CR14R15)qOC(=Y’)NR11R12, (CR14R15)qOS(O)2(OR11), -(CR14R15)qOP(-Y’)(OR11)(OR12), -(CR14R15)qOP(OR11)(OR12), -(CR14R15)nS(O)R11, -(CR14R15)nS(O)2R11, -(CR14R15)nS(O)2NR11R12, C1-C12-alkil, C2-C8-alkenil, C2-C8-alkinil, karbociklil, heterociklil, aril i heteroaril; R10 je H, C1-C6-alkil ili C3-C4-karbociklil; X4 je [image] R6 je H, halo, C1-C6-alkil, C2-C8-alkenil, C2-C8-alkinil, karbociklil, heteroaril, heterociklil, -OCF3, -NO2, -Si(C1-C6-alkil), -(CR19R20)nNR16R17, -(CR19R20)nOR16, ili -(CR19R20)n-SR16; R6’ je H, halo, C1-C6-alkil, karbociklil, CF3, -OCF3, -NO2, -Si(C1-C6-alkil), -CR19R20)nNR16R17, -(CR19R20)nOR16, -(CR19R20)n-SR16, C2-C8-alkenil, C2-C8-alkinil, heterociklil, aril ili heteroaril; p je 0, 1, 2 ili 3; n je 0, 1, 2 ili 3; q je 2 ili 3; pri čemu je svaki navedeni alkil, alkenil, alkinil, karbociklil, heterociklil, aril i heteroaril od R1, R2, R3, R4, R5, R6, R6’, R7, R8, R9, R10, R11, R11’, R12, R13, R14, R15 i RA , neovisno po želji supstituiran s jednom ili više skupina neovisno odabranih od sljedećih: halo, CN, CF3, -OCF3, -NO2, okso, -Si(C1-C6-alkil), -(CR19R20)nC(=Y’)R16, -(CR19R20)nC(=Y’)OR16, -(CR19R20)nC(=Y’)NR16R17, -(CR19R20)nNR16R17, -(CR19R20)nOR16, -(CR19R20)nSR16, -(CR19R20)nNR16C(=Y’)R17, -(CR19R20)nNR16C(=Y’)OR17, -(CR19R20)nNR18C(=Y’)NR16R17, -(CR19R20)nNR17SO2R16, -(CR19R20)nOC(=Y’)R16, -(CR19R20)nOC(=Y’)OR16, -(CR19R20)nOC(=Y’)NR16R17, (CR19R20)nOS(O)2(OR16), -(CR19R20)nOP(=Y’)(OR16)(OR17), -(CR19R20)nOP(OR16)(OR17), -(CR19R20)nS(O)R16, -(CR19R20)nS(O)2R16, -(CR19R20)nS(O)2NR16R17, -(CR19R20)nS(O)(OR16), -(CR19R20)nS(O)2(OR16), -(CR19R20)nSC(=Y’)R16, -(CR19R20)nSC(=Y’)OR16, -(CR19R20)nSC(=Y’)NR16R17 i R21; svaki R16, R17 i R18 je neovisno H, C1-C12-alkil, C2-C8-alkenil, C2-C8-alkinil, karbociklil, heterociklil, aril ili heteroaril, pri čemu je navedeni alkil, alkenil, alkinil, karbociklil, heterociklil, aril ili heteroaril po želji supstituiran s jednom ili više skupina odabranih od sljedećih: halo, CN, -OCF3, CF3, -NO2, C1-C6-alkil, -OH, -SH, -O(C1-C6-alkil), -S(C1-C6-alkil), -NH2, -NH(C1-C6-alkil), -N(C1-C6-alkil)2, -SO2(C1-C6-alkil), -CO2H, -CO2(C1-C6-alkil), -C(O)NH2, -C(O)NH(C1-C6-alkil), -C(O)N(C1-C6-alkil)2, -N(C1-C6-alkil)C(O)(C1-C6-alkil), -NHC(O)(C1-C6-alkil), -NHSO2(C1-C6-alkil), -N(C1-C6-alkil)SO2(C1-C6-alkil), -SO2NH2, -SO2NH(C1-C6-alkil), -SO2N(C1-C6-alkil)2, -OC(O)NH2, -OC(O)NH(C1-C6-alkil), -OC(O)N(C1-C6-alkil)2, -OC(O)O(C1-C6-alkil), -NHC(O)NH(C1-C6-alkil), -NHC(O)N(C1-C6-alkil)2, -N(C1-C6-alkil)C(O)NH(C1-C6-alkil), -N(C1-C6-alkil)C(O)N(C1-C6-alkil)2, -NHC(O)NH(C1-C6-alkil), -NHC(O)N(C1-C6-alkil)2, -NHC(O)O(C1-C6-alkil), i -N(C1-C6-alkil)C(O)O(C1-C6-alkil); ili R16 i R17 zajedno s dušikom na kojega su priključeni, tvore 3-8-člani zasićeni, nezasićeni ili aromatski prsten koji ima od 0 do 2 heteroatoma odabrana od O, S i N, pri čemu je spomenuti prsten po želji supstituiran s jednom ili više skupina odabranih od sljedećih: halo, CN, -OCF3, CF3, -NO2, C1-C6-alkil, -OH, -SH, -O(C1-C6-alkil), -S(C1-C6-alkil), -NH2, -NH(C1-C6-alkil), -N(C1-C6-alkil)2, -SO2(C1-C6-alkil), -CO2H, -CO2(C1-C6-alkil), -C(O)NH2, -C(O)NH(C1-C6-alkil), -C(O)N(C1-C6-alkil)2, -N(C1-C6-alkil)C(O)(C1-C6-alkil), -NHC(O)(C1-C6-alkil), -NHSO2(C1-C6-alkil), -N(C1-C6-alkil)SO2(C1-C6-alkil), -SO2NH2, -SO2NH(C1-C6-alkil), -SO2N(C1-C6-alkil)2, -OC(O)NH2, -OC(O)NH(C1-C6-alkil), -OC(O)N(C1-C6-alkil)2, -OC(O)O(C1-C6-alkil), -NHC(O)NH(C1-C6-alkil), -NHC(O)N(C1-C6-alkil)2, -N(C1-C6-alkil)C(O)NH(C1-C6-alkil), N(C1-C6-alkil)C(O)N(C1-C6-alkil)2, -NHC(O)NH(C1-C6-alkil), -NHC(O)N(C1-C6-alkil)2, -NHC(O)O(C1-C6-alkil), i -N(C1-C6-alkil)C(O)O(C1-C6-alkil); R19 i R20 su neovisno odabrani od sljedećih: H, C1-C12-alkil, -(CH2)n-aril, -(CH2)n-karbociklil, -(CH2)n-heterociklil, i -(CH2)n-heteroaril; R21 je C1-C12-alkil, C2-C8-alkenil, C2-C8-alkinil, karbociklil, heterociklil, aril ili heteroaril, pri čemu je svaki član od R21 po želji supstituiran s jednom ili više skupina odabranih od sljedećih: halo, okso, CN, -OCF3, CF3, -NO2, C1-C6-alkil, -OH, -SH, -O(C1-C6-alkil), -S(C1-C6-alkil), -NH2, -NH(C1-C6-alkil), -N(C1-C6-alkil)2, -SO2(C1-C6-alkil), -CO2H, -CO2(C1-C6-alkil), -C(O)NH2, -C(O)NH(C1-C6-alkil), -C(O)N(C1-C6-alkil)2, -N(C1-C6-alkil)C(O)(C1-C6-alkil), -NHC(O)(C1-C6-alkil), -NHSO2(C1-C6-alkil), -N(C1-C6-alkil)SO2(C1-C6-alkil), -SO2NH2, -SO2NH(C1-C6-alkil), -SO2N(C1-C6-alkil)2, -OC(O)NH2, -OC(O)NH(C1-C6-alkil), -OC(O)N(C1-C6-alkil)2, -OC(O)O(C1-C6-alkil), -NHC(O)NH(C1-C6-alkil), -NHC(O)N(C1-C6-alkil)2, -N(C1-C6-alkil)C(O)NH(C1-C6-alkil), -N(C1-C6-alkil)C(O)N(C1-C6-alkil)2, -NHC(O)NH(C1-C6-alkil), -NHC(O)N(C1-C6-alkil)2, -NHC(O)O(C1-C6-alkil), i -N(C1-C6-alkil)C(O)O(C1-C6-alkil); svaki Y’ je neovisno O, NR22, ili S; i R22 je H ili C1-C12-alkil.
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