HRP20220118T1 - Agonisti fenilpirolidinon formil peptidnih 2 receptora - Google Patents

Agonisti fenilpirolidinon formil peptidnih 2 receptora Download PDF

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HRP20220118T1
HRP20220118T1 HRP20220118TT HRP20220118T HRP20220118T1 HR P20220118 T1 HRP20220118 T1 HR P20220118T1 HR P20220118T T HRP20220118T T HR P20220118TT HR P20220118 T HRP20220118 T HR P20220118T HR P20220118 T1 HRP20220118 T1 HR P20220118T1
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Croatia
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alkyl
halo
image
hydrogen
alkoxy
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HRP20220118TT
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Pravin Sudhakar Shirude
Vishweshwaraiah BALIGAR
Balaji SESHADRI
Amit Kumar Chattopadhyay
Nicholas R. Wurtz
Ellen K. Kick
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Bristol-Myers Squibb Company
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Publication of HRP20220118T1 publication Critical patent/HRP20220118T1/hr

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Claims (30)

1. Spoj sa formulom (II): [image] ili farmaceutski prihvatljiva sol istog, pri čemu: Ar1 je aril supstituiran sa 1-2 R1a i 1-2 R1b ili monociklični heteroaril sa 1-3 heteroatoma odabrana od dušika, kisika i sumpora, i supstituiran sa 1-2 R1a i 1-2 R1b; Ar2 je aril supstituiran sa 1-4 R2a ili 6-člani heteroaril sa 1-2 atoma dušika, i supstituiran sa 1-4 R2a; Ar3 je aril supstituiran sa 1-4 R3a ili monociklični heteroaril sa 1-3 heteroatoma odabrana od dušika, kisika i sumpora, i supstituiran sa 1-4 R3a; R1a je vodik ili halo; R1b je halo, haloalkil, alkoksi, ili haloalkoksi; R2a je vodik, cijano, halo, alkil, hidroksialkil, haloalkil, cikloalkil, alkoksi, ili haloalkoksi; alternativno, dvije susjedne R2a grupe su uzete zajedno sa atomima ugljika za koje su vezane da formiraju heterociklus sa 1-4 heteroatoma odabrana od dušika, kisika i sumpora; R3a je cijano, halo, alkil, alkoksi, hidroksialkil, alkoksialkil, haloalkil, (R1R2N)alkil, R1R2N, alkilC(O)(R2)Nalkil, (alkil)2(O)P, (alkoksi)2(O)P, (alkoksi)(alkil)(O)P, (alkil)(O)(NR1)S, alkilSO2, ili alkilSO2NH; alternativno, dvije susjedne R3a grupe su uzete zajedno sa atomima ugljika za koje su vezane da formiraju heterociklus sa1-4 heteroatoma odabrana od dušika, kisika i sumpora; R4a ili R4b je nezavisno vodik, alkil, alkoksi, hidroksilalkil, alkoksialkil, ili haloalkoksi; alternativno, R4a i R4b zajedno sa atomom ugljika oba su vezana da formiraju C3-6 cikloalkil; R5a ili R5b je nezavisno vodik, alkil, hidroksilalkil, alkoksialkil ili haloalkoksil; R1 je vodik ili alkil; i R2 je vodik ili alkil; ili R1R2N uzeto zajedno je azetidinil, oksazolil pirolidinil, piperidinil, piperazinil, ili morfolinil, i supstituirano je sa 0-3 supstituenta odabrana od halo, alkil, i okso; alkil označava ravnu ili razgranatu alkil grupu sačinjenu od 1do 6 ugljika; cikloalkil označava monociklični prstenasti sustav sastavljen od 3 do 7 ugljika.
2. Spoj prema patentnom zahtjevu 1, koje ima formulu (III): [image] ili farmaceutski prihvatljiva sol istog, pri čemu: Ar1 je fenil supstituiran sa 1-2 R1a i 1-2 R1b ili 6-člani heteroaril sa 1-3 atoma dušika i supstituiran sa 1R1a i 1-2 R1b; Ar3 je fenil supstituiran sa 1-3 R3a ili 5- do 6-člani heteroaril sa 1-3 atoma dušika i supstituiran sa 1-3 R3a; R1a je vodik ili halo; R1b je halo, C1-4 haloalkil, C1-4 alkoksi, ili C1-4 haloalkoksi; R2a je vodik, halo, C1-4 alkil, C1-4hidroksialkil, C1-4haloalkil, C3-6 cikloalkil, C1-4 alkoksi, ili C1-4 haloalkoksi; R3a je cijano, halo, C1-4 alkil, C1-4hidroksialkil, C1-4 alkoksialkil, C1-4 haloalkil, (R1R2N)C1-4 alkil, R1R2N, C1-4 alkilC(O)(R2)NC1-4 alkil, (C1-4 alkil)2(O)P, (C1-4 alkoksi)2(O)P, (C1-4 alkoksi)(C1-4 alkil)(O)P, C1-4 alkilSO2, ili C1-4 alkilSO2NH; R1R2N uzeto zajedno je oksazolil ili pirolidinil i supstituirano je sa 0-3 supstituenta odabrana od halo, alkil, i okso; R4a ili R4b je nezavisno vodik, C1-4 alkil, ili C1-4 hidroksilalkil; alternativno, R4a i R4b zajedno sa atomom ugljika oba su vezana da formiraju C3-6 cikloalkil; i R5a ili R5b je nezavisno vodik, C1-4 alkil, C1-4 hidroksilalkil, ili C1-4 alkoksialkil.
3. Spoj prema patentnom zahtjevu 2, ili farmaceutski prihvatljiva sol istog, pri čemu: Ar1 je fenil supstituiran sa 1-2 R1a i 1-2 R1b, piridinil supstituiran sa 1 R1a i 1-2 R1b, ili pirazinil supstituiran sa 1R1a i 1-2 R1b; i Ar3 je fenil supstituiran sa 1-3 R3a, pirazolil supstituiran sa 1-3 R3a, piridinil supstituiran sa 1-3 R3a, ili pirimidinil supstituiran sa 1-3 R3a.
4. Spoj prema patentnom zahtjevu 2 ili 3, koje ima formulu (IV): [image] ili farmaceutski prihvatljiva sol istog, pri čemu: Ar1 je fenil supstituiran sa 1-2 R1a i 1-2 R1b, piridinil supstituiran sa 1 R1a i 1-2 R1b, ili pirazinil supstituiran sa 1 R1a i 1-2 R1b; R1a je vodik ili halo; R1b je halo, C1-4 haloalkil, C1-4 alkoksi, ili C1-4 haloalkoksi; R2a je vodik, halo, C1-4 alkil, C1-4hidroksialkil, C1-4haloalkil, C3-6 cikloalkil, C1-4 alkoksi, ili C1-4haloalkoksi; R3a je cijano, halo, C1-3 alkil, C1-3hidroksialkil, C1-3 alkoksialkil, C1-3 haloalkil, R1R2N, (C1-3 alkil)2(O)P, (C1-3 alkoksi)2(O)P, (C1-3 alkoksi)(C1-3 alkil)(O)P, C1-3 alkilSO2, ili C1-3 alkilSO2NH; R4a ili R4b je nezavisno vodik, C1-3 alkil, ili C1-3 hidroksilalkil; alternativno, R4a i R4b zajedno sa atomom ugljika oba su vezana da formiraju C3-6 cikloalkil; i R5a ili R5b je nezavisno vodik, C1-3 alkil, C1-3 hidroksilalkil, ili C1-3 alkoksialkil.
5. Spoj prema patentnom zahtjevu 4, koji ima formulu (V): [image] ili farmaceutski prihvatljiva sol istog, pri čemu: R1a je vodik ili F; R1b je halo, C1-2 haloalkil, ili C1-2 alkoksi; R2a je vodik, halo, C1-3 alkil, C1-3 haloalkil, ili C3-6 cikloalkil; R3a je halo, hidroksialkil, alkoksialkil, (C1-2 alkil)2(O)P, (C1-2 alkoksi)2(O)P, (C1-2 alkoksi)(C1-2 alkil)(O)P, C1-2 alkilSO2, ili C1-2 alkilSO2NH; i R3a' je halo.
6. Spoj prema patentnom zahtjevu 5, ili farmaceutski prihvatljiva sol istog, pri čemu: R1a je vodik ili F; R1b je F, Cl, ili CF3; R2a je vodik, F, Cl, izopropil, CF3, ili ciklopropil; R3a je (CH3)2(O)P, (CH3CH2)2(O)P, (CH3CH2O)(CH3)(O)P, CH3SO2, ili CH3SO2NH; i R3a' je F.
7. Spoj prema patentnom zahtjevu 4, koji ima formulu (VI): [image] ili farmaceutski prihvatljiva sol istog, pri čemu: R1a je vodik ili halo; R1b je halo, C1-2haloalkil, ili C1-2 alkoksi; R2a je vodik, halo, C1-3 alkil, ili C3-6 cikloalkil; R3a je (C1-2 alkil)2(O)P, (C1-2 alkoksi)2(O)P, (C1-2 alkoksi)(C1-2 alkil)(O)P, C1-2 alkilSO2, ili C1-2 alkilSO2NH.
8. Spoj prema patentnom zahtjevu 2 ili 3, koji ima formulu (VII): [image] ili farmaceutski prihvatljiva sol istog, pri čemu: Ar3 je pirazolil supstituiran sa 1-3 R3a, piridinil supstituiran sa 1-3 R3a, ili pirimidinil supstituiran sa 1-3 R3a; R1a je vodik ili halo; R1b je halo, C1-4 haloalkil, C1-4 alkoksi, ili C1-4 haloalkoksi; R2a je vodik, halo, C1-4 alkil, C1-4hidroksialkil, C1-4haloalkil, C3-6 cikloalkil, C1-4 alkoksi, ili C1-4haloalkoksi; R3a je cijano, halo, C1-4 alkil, C1-4hidroksialkil, C1-4 alkoksialkil, (R1R2N)C1-4 alkil, R1R2N-, (C1-4 alkil)2(O)P, (C1-4 alkoksi)2(O)P, (C1-4 alkoksi)(C1-4 alkil)(O)P, C1-4 alkilSO2, ili C1-4 alkilSO2NH; R1 je vodik ili alkil; R2 je vodik ili alkil; ili R1R2N uzeto zajedno je oksazolil ili pirolidinil, i supstituirano je sa 0-3 supstituenta odabrana od halo, alkil, ili okso; R4a ili R4b je nezavisno vodik, C1-4 alkil, C1-4 alkoksi, C1-4 alkoksialkil, ili C1-4haloalkoksi; R4a i R4b zajedno sa atomom ugljika oba su vezana da formiraju C3-6 cikloalkil; i R5a ili R5b je nezavisno vodik, C1-4 alkil, C1-4 alkoksi, C1-4 alkoksialkil, ili C1-4haloalkoksi.
9. Spoj prema patentnom zahtjevu 8, koji ima formulu (VIII): [image] ili farmaceutski prihvatljiva sol istog, pri čemu: R1a je vodik ili halo; R1b je halo, C1-2haloalkil, ili C1-2 alkoksi; R2a je vodik, halo, C1-3 alkil, ili C3-6 cikloalkil; R3a je (C1-2 alkil)2(O)P, (C1-2 alkoksi)2(O)P, (C1-2 alkoksi)(C1-2 alkil)(O)P, C1-2 alkilSO2, ili C1-2 alkilSO2NH; i R5a ili R5b je nezavisno vodik ili C1-2 alkil.
10. Spoj prema patentnom zahtjevu 1, koji ima formulu (IX): [image] ili farmaceutski prihvatljiva sol istog, pri čemu: R1a je vodik ili halo; R1b je halo, C1-2haloalkil, ili C1-2 alkoksi; R2a je vodik, halo, C1-2 haloalkil, C1-3 alkil, ili C3-6 cikloalkil; Ar3 je [image] R3a je (C1-2 alkil)2(O)P, (C1-2 alkoksi)(C1-2 alkil)(O)P, ili C1-2 alkilSO2NH; R3a je halo; R4a ili R4b je nezavisno vodik, C1-2 alkil, ili C1-2 hidroksialkil; ili R4a i R4b zajedno sa atomom ugljika za koji su oba vezana formiraju C3-6 cikloalkil; i R5a ili R5b je nezavisno vodik, C1-2 alkil, C1-2 hidroksialkil, ili C1-2 alkoksialkil.
11. Spoj prema patentnom zahtjevu 4, ili farmaceutski prihvatljiva sol istog, pri čemu: R4a je vodik; R4b je vodik; R5a je C1-2 alkil, C1-2 hidroksilalkil, ili C1-2 alkoksialkil; i R5b je vodik.
12. Spoj prema patentnom zahtjevu 4, ili farmaceutski prihvatljiva sol istog, pri čemu: R4a je C1-2 alkil; R4b je C1-2 alkil; R5a je vodik; i R5b je vodik.
13. Spoj prema patentnom zahtjevu 1, sa formulom (I): [image] pri čemu: Ar1 je fenil, piridinil, ili piridazinil i supstituiran je sa 1 halo, haloalkil ili haloalkoksi supstituentom u položaju 4 i 0-2 dodatna halo ili haloalkil supstituenta; Ar2 je fenil ili piridinil i supstituiran je sa 0-2 supstituenta odabrana od cijano, fluoro, alkil, haloalkil, cikloalkil, alkoksi, i haloalkoksi; Ar3 je fenil ili piridinil i supstituiran je sa 0-2 supstituenta odabrana od cijano, halo, hidroksialkil, alkoksialkil, (R1R2N)alkil, (alkil)2(O)P, (alkil)(O)(NR1)S, alkilSO2, i alkilSO2NH; R1 je vodik ili alkil; i R2 je vodik ili alkil; ili (R1)(R2)N uzeto zajedno je azetidinil, pirolidinil, piperidinil, piperazinil, ili morfolinil i supstituirano je sa 0-3 supstituenta odabrana od halo i alkil; ili farmaceutski prihvatljiva sol istog.
14. Spoj prema patentnom zahtjevu 13 pri čemu Ar1 je fenil supstituiran sa 1 halo, haloalkil ili haloalkoksi supstituentom u položaju 4 i 0-2 dodatna halo ili haloalkil supstituenta.
15. Spoj prema patentnom zahtjevu 13 pri čemu Ar2 je fenil supstituiran sa 0 supstituenata, 1 alkil ili cikloalkil supstituentom, ili 1-2 fluoro supstituenta.
16. Spoj prema patentnom zahtjevu 13 pri čemu Ar3 je fenil supstituiran sa 1-2 supstituenta odabrana od cijano, halo, hidroksialkil, alkoksialkil, (R1R2N)alkil, (alkil)2(O)P, (alkil)(O)(NR1)S, alkilSO2, i alkilSO2NH.
17. Spoj prema patentnom zahtjevu 13 pri čemu R1 je vodik i R2 je vodik.
18. Spoj prema patentnom zahtjevu 13 odabran iz grupe koja se sastoji od [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] i [image] ili farmaceutski prihvatljiva sol istog.
19. Spoj prema patentnom zahtjevu 1 koji je odabrano iz grupe koja se sastoji od [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] ili farmaceutski prihvatljiva sol istog.
20. Spoj prema patentnom zahtjevu 19, koji je [image] ili farmaceutski prihvatljiva sol istog.
21. Spoj prema patentnom zahtjevu 19, koji je [image] ili farmaceutski prihvatljiva sol istog.
22. Spoj prema patentnom zahtjevu 19, koji je [image] ili farmaceutski prihvatljiva sol istog.
23. Spoj prema patentnom zahtjevu 19, koji je [image] ili farmaceutski prihvatljiva sol istog.
24. Spoj prema patentnom zahtjevu 19, koji je [image] ili farmaceutski prihvatljiva sol istog.
25. Kompozicija koja sadrži spoj iz bilo kojeg od patentnih zahtjeva 1-24, ili farmaceutski prihvatljiva sol istog, i farmaceutski prihvatljiv nosač, razblaživač, ili ekscipijens.
26. Spoj prema bilo kojem od patentnih zahtjeva 1-24, ili farmaceutski prihvatljiva sol istog ili kompozicija prema patentnom zahtjevu 25 za primjenu u liječenju.
27. Spoj prema bilo kojem od patentnih zahtjeva 1-24 ili farmaceutski prihvatljiva sol istog za primjenu u liječenju bolesti srca kod pacijenta koji ima potrebu za istim.
28. Spoj ili farmaceutski prihvatljiva sol istog za primjenu prema patentnom zahtjevu 27 pri čemu je bolest srca odabrana iz grupe koja se sastoji od angine pektoris, nestabilne angine, infarkta miokarda, insuficijencije srca, akutne koronarne bolesti, akutne insuficijencije srca, kronične insuficijencije srca, i srčanog jatrogenog oštećenja.
29. Spoj ili farmaceutski prihvatljiva sol istog za primjenu prema patentnom zahtjevu 28 pri čemu je insuficijencija srca odabrana iz grupe koja se sastoji od kongestivne insuficijencije srca, sistolne insuficijencije srca, dijastolne insuficijencije srca, insuficijencije srca sa reduciranom ejekcijskom frakcijom (HFREF), insuficijencije srca sa očuvanom ejekcijskom frakcijom (HFPEF), akutne insuficijencije srca, kronične insuficijencije srca ishemijskog i neishemijskog porijekla.
30. Spoj ili farmaceutski prihvatljiva sol istog za primjenu prema patentnom zahtjevu 28 pri čemu je bolest srca insuficijencija srca.
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