HRP20201522T1 - Heteroaromatski nmda receptor modulatori i njihove uporabe - Google Patents

Heteroaromatski nmda receptor modulatori i njihove uporabe Download PDF

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HRP20201522T1
HRP20201522T1 HRP20201522TT HRP20201522T HRP20201522T1 HR P20201522 T1 HRP20201522 T1 HR P20201522T1 HR P20201522T T HRP20201522T T HR P20201522TT HR P20201522 T HRP20201522 T HR P20201522T HR P20201522 T1 HRP20201522 T1 HR P20201522T1
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halogen
optionally substituted
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cyano
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David R. Anderson
Robert A. Volkmann
Frank S. Menniti
Christopher Fanger
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Cadent Therapeutics, Inc.
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Claims (15)

1. Spoj predstavljen Formulom I [image] ili njegova farmaceutski prihvatljiva sol, pri čemu: prstenovi A i B su spojeni [5,6] ili [6,6] heteroaromatski sustav; Q je N ili CR6; T je N ili CR6; i y je 0 ili 1 pri čemu kada y je 1, U1 i U2 je C; W i V je svaki neovisno odabrani iz CR6; jedno od Y i X je CR3 i jedno od Y i X je CR6; i kada y je 0: X je CR3 ili NR33; W je odabrano iz skupine koja sadrži CR6, N ili S; V je odabrano iz skupine koja sadrži N, NR7, CR6, S i O; U1 i U2 mogu svaki biti C ili N; pri čemu kada jedno od U1 i U2 je N drugo je C; i kada Q je CR6, T je N, W je CR6 i X je CR3; V nije S; L1 je veza ili C1-4alkilen po izboru prekinut pomoću O, i po izboru supstituiran na ugljiku koji nije vezan na dušični prsten jednim, dva, ili tri supstituenata svaki neovisno odabran iz skupine koja sadrži halogen, OH, cijano i -NRaRb; R1 i R2, zajedno s dušikom na koji su spojeni, tvore 4-6 člani monociklički heterociklički prsten po izboru supstituiran na ugljik pomoću jednog, dva ili više supstituenata svaki odabran iz skupine koja sadrži halogen, cijano, okso, hidroksil i C1-6alkil po izboru supstituiran pomoću jednog, dva ili tri halogena; R3 je fenil, tiofenil, pirimidinil, pirazinil ili piridinil, svaki po izboru supstituiran pomoću jednog ili dva supstituenta svaki neovisno odabran iz skupine koja sadrži halogen i C1-3alkil opciono supstituiran pomoću jednog, dva ili tri halogena; R33 je odabran iz skupine koja sadrži fenil, naftil, heteroaril, heterociklil i C3-6cikloalkil, pri čemu je R33 po izboru supstituirano s jednim, dva ili tri supstituenta svakim neovisno odabranim iz skupine koja sadrži C1-4alkil, halogen, hidroksil, C1-4alkoksi, C2-6alkenil, C2-6alkinil, C3-6cikloalkil, C1-6alkil-S(O)2-, C1-6alkilkarbonil, RaRbN-SO2-, NRaRb, C(O)OH, C1-4alkoksikarbonil, i NRaRbkarbonil; pri čemu C1-6alkil, C2-6alkenil, C2-6alkinil, C3-6cikloalkil, C1-6alkil-S(O)2- i C1-6alkilkarbonil mogu biti po izboru supstituirani jednim ili više supstituenata svakim odabranim iz skupine koja sadrži halogen, hidroksil, cijano, i NRaRb; R6 je neovisno odabran pri svakoj pojavi iz skupine koja sadrži vodik, halogen, cijano, C1-4 alkil, C(O)OH, C(O)H, -C(=NH)-NRaRc, fenil, piridinil i pirimidinil, pri čemu je spomenuti C1-4 alkil po izboru supstituiran jednim ili više supstituenata odabranim iz skupine koja sadrži -NRaRb, C1-4alkoksi, halogen, cijano, hidroksil, C(O)H, i =NRa i spomenuti fenil je po izboru supstituiran uz pomoć jednog ili dva supstituenta svakim i odabranim iz skupine koja sadrži NRaRb, C1-4alkoksi, halogen, cijano, hidroksil, C(O)H, i =NRa I, i R7 je odabran iz skupine koja sadrži vodik, C1-6alkil, C2-6alkinil, C3-6cikloalkil, heterociklil, heteroaril, i fenil; pri čemu C1-6alkil, C2-6alkenil i C3-6cikloalkil mogu po izboru biti supstituirani jednim ili više supstituenata svakim odabranim iz skupine koja sadrži halogen, hidroksil, C1-4alkoksi, cijano, -Si(Rs)0-3, -O-Si(Rs)0-3, i NRaRb, pri čemu Rs je H ili C1-6alkil i pri čemu spomenuti C1-4alkoksi je po izboru supstituiran s halogenom ili -Si(Rs)0-3; Rc je odabrani iz skupine koja sadrži vodik, C1-3alkil, i hidroksil; Ra i Rb su neovisno odabrani, pri svakoj pojavi, iz skupine koja sadrži vodik, C1- 4alkilkarbonil, -C(O)-O-C1-4alkil, C3-6cikloalkil i C1-3alkil; pri čemu C1-3alkil i C3-6cikloalkil mogu po izboru biti supstituirani na ugljiku koji nije vezan na dušik jednim ili više supstituenata svakim odabranim iz skupine koja sadrži fluor, cijano, okso i hidroksil; ili Ra i Rb, zajedno s dušikom na koji su spojeni, tvore 4-6 člani heterociklični prsten koji može imati dodatni heteroatom odabran od O, S, ili N; i pri čemu 4-6 člani heterociklični prsten može po izboru biti supstituiran na ugljiku koji nije vezan na dušik jednim ili više supstituenata odabranih iz skupine koja sadrži fluor, metil, cijano, okso i hidroksil.
2. Spoj sukladno patentnom zahtjevu 1, pri čemu je spojeni [5,6] ili [6,6] heteroaromatski sustav odabran iz skupine koja sadrži: [image] [image] [image] [image]
3. Spoj sukladno patentnom zahtjevu 1 ili 2, pri čemu je spojeni [5,6] heteroaromatski sustav odabran iz skupine koja sadrži: [image] [image]
4. Spoj sukladno bilo kojem od patentnih zahtjeva 1-3, pri čemu spojeni [5,6] heteroaromatski sustav je: [image]
5. Spoj sukladno bilo kojem od patentnih zahtjeva 1-4, pri čemu L1 je -CH2-.
6. Spoj sukladno bilo kojem od patentnih zahtjeva 1-5, pri čemu je spoj predstavljen: [image] pri čemu: U1 i U2 može svaki biti C ili N; pri čemu kada jedan od U1 i U2 je N drugi je C; T je N ili CR6; R66 i R67 su svaki neovisno odabran iz skupine koja sadrži halogen, C1-4 alkil po izboru supstituirani pomoću jednog, dva, tri supstituenta odabran od halogena, hidroksila, cijano i NRaRb; i V je odabran iz skupine koja sadrži N, NR7, CR66 i S.
7. Spoj sukladno patentnom zahtjevu 6, pri čemu U1 je N i U2 je C.
8. Spoj sukladno bilo kojem od patentnih zahtjeva 1-7, pri čemu V je NR7.
9. Spoj sukladno bilo kojem od patentnih zahtjeva 6-8, je predstavljeno pomoću: [image] pri čemu V je NR7 ili S.
10. Spoj sukladno bilo kojem od patentnih zahtjeva 1-9, pri čemu je R7 odabran iz skupine koja sadrži vodik, C1-6alkil, piridil, i fenil; pri čemu je C1-6alkil po izboru supstituiran jednim ili više supstituenata svaki odabran iz skupine koja sadrži vodik, hidroksil, i C1-4alkoksi.
11. Spoj predstavljen pomoću: [image] Ili njegova farmaceutski prihvatljivu sol, pri čemu: R1 i R2, zajedno s dušikom na koji su spojeni, tvore 4-6 člani monociklični heterociklički prsten po izboru supstituiran na ugljiku jednim, dva ili više supstituenata svaki odabran iz skupine koja sadrži halogen, cijano, okso, hidroksil i C1-6 alkil po izboru supstituiranim pomoću jednog, dva ili tri halogena; R3 je fenil, tiofenil, pirimidinil, pirazinil ili piridinil, svaki po izboru supstituiran pomoću jednog ili dva supstituenta svakim neovisno odabran iz skupine koja sadrži halogen i C1-3alkil po izboru supstituiran pomoću jednog, dva ili tri halogena; R6 je svakim neovisno odabran za svaku pojavu iz skupine koja sadrži vodik, C1-6 alkil, C1-6alkoksi, halogen, cijano, C2-6alkenil, C2-6alkinil, C3-6cikloalkil, heteroaril, fenil, -C(=NH)-NRaRc, C(=N-OH)-H, C(=N-OH)-C1-6alkil, -NRaRb, C(O)OH, C1-6alkilkarbonil, C1-6alkoksikarbonil, NRaRbkarbonil-, i RaRbN- SO2-; pri čemu su fenil i heteroaril su po izboru supstituirani jednim ili više supstituenata svakim odabranim iz skupine koja sadrži halogen, C1-4 alkil po izboru supstituiran pomoću halogena, cijano, C1-4 alkoksi, -NRaRb, =NRa, -C(=NH)-NRaRc, i RaRbN-SO2; i pri čemu su svaki C1-6 alkil, C1-6alkoksi, C2-6alkenil, C2-6alkinil, i C3-6cikloalkil po izboru supstituirani jednim ili više supstituenata svakim odabranim iz skupine koja sadrži hidroksil, cijano, C1-4alkoksi, halogen, NRaRb, =NRa, -C(=NH)- NRaRc, cijano, i RaRbN-SO2-, R66 i R67 su svaki neovisno odabranim iz skupine koja sadrži halogen, C1-4 alkil po izboru supstituiran pomoću jednog, dva, tri supstituenta odabranim između halogena, hidroksil, cijano i NRaRb; i R7 je odabran iz skupine koja sadrži vodik, C1-6alkil, C2-6alkinil, C3-6cikloalkil, heterociklil, heteroaril, i fenil; pri čemu C1-6alkil, C2-6alkenil, i C3-6cikloalkil može po izboru biti supstituiran jednim ili više supstituenata svakim odabranim iz skupine koja sadrži halogen, hidroksil, C1-4 alkoksi, cijano, -Si(Rs)0-3, -O-Si(Rs)0-3, i NRaRb; pri čemu Rs je H ili C1-6alkil i pri čemu spomenuti C1-4alkoksi je po izboru supstituiran pomoću halogena ili -Si(Rs)0-3 Rc je odabrano iz skupine koja sadrži vodik, C1-3alkil, i hidroksil; Ra i Rb su neovisno odabrani, za svaku pojavu, iz skupine koja sadrži vodik, hidroksil, i C1-3alkil; pri čemu C1-3alkil može po izboru biti supstituiran pomoću jednog ili više supstituenata odabranih iz skupine koja sadrži fluor, cijano, okso i hidroksil; ili Ra i Rb, zajedno s dušikom na koji su spojeni, tvore 4-6 člani heterociklički prsten koji može imati dodatni heteroatom odabran iz O, S, ili N.
12. Spoj sukladno patentnom zahtjevu 11, pri čemu R7 je odabrano iz skupine koja sadrži vodik, C1-6alkil, C3-6cikloalkil, heteroaril, i fenil; pri čemu C1-6alkil je po izboru supstituiran jednim ili više supstituenata svakim odabranim iz skupine koja sadrži halogen, hidroksil, C1-4 alkoksi, cijano, i NRaRb, pri čemu spomenuti C1-4 alkoksi je po izboru supstituiran pomoću halogena ili -Si(Rs)0-3 i pri čemu spomenuto RS je vodik ili C1-6alkil.
13. Farmaceutski prihvatljivi pripravak koji sadrži spoj, sukladno bilo kojem od patentnih zahtjeva 1-12, ili njegova farmaceutski prihvatljiva sol, i njegov farmaceutski prihvatljivi ekscipijens.
14. Spoj sukladno bilo kojem od patentnih zahtjeva 1-12, ili farmaceutski prihvatljivi pripravak sukladno patentnom zahtjevu 13, za uporabu u liječenju neuropsihijatrijskog poremećaja.
15. Spoj ili farmaceutski prihvatljivi pripravak za uporabu sukladno patentnom zahtjevu 14, pri čemu je neuropsihijatrijski poremećaj odabran između shizofrenije, depresije, poremećaja iz spektra autizma i Rett sindroma.
HRP20201522TT 2015-12-09 2020-09-23 Heteroaromatski nmda receptor modulatori i njihove uporabe HRP20201522T1 (hr)

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US201562265182P 2015-12-09 2015-12-09
PCT/US2016/065852 WO2017100591A1 (en) 2015-12-09 2016-12-09 Heteroaromatic nmda receptor modulators and uses thereof
EP16820103.6A EP3386591B1 (en) 2015-12-09 2016-12-09 Heteroaromatic nmda receptor modulators and uses thereof

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