HRP20230125T1 - Spojevi kao modulatori signaliziranja tlr2 - Google Patents

Spojevi kao modulatori signaliziranja tlr2 Download PDF

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HRP20230125T1
HRP20230125T1 HRP20230125TT HRP20230125T HRP20230125T1 HR P20230125 T1 HRP20230125 T1 HR P20230125T1 HR P20230125T T HRP20230125T T HR P20230125TT HR P20230125 T HRP20230125 T HR P20230125T HR P20230125 T1 HRP20230125 T1 HR P20230125T1
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Croatia
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image
alkyl
unsubstituted
substituted
alkoxy
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HRP20230125TT
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Srinivasa Reddy Natala
Wolfgang Wrasidlo
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Neuropore Therapies, Inc.
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Publication of HRP20230125T1 publication Critical patent/HRP20230125T1/hr

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Claims (20)

1. Spoj, naznačen time, da je predstavljen Formulom (A): [image] ili njegov tautomer, ili farmaceutski prihvatljiva sol od bilo kojega predstojećeg, pri čemu: [image] pokazuje da je prsten zasićen, djelomično nezasićen, ili potpuno nezasićen; [image] pokazuje da je [image] vezana u E ili Z konfiguraciji; svaki od G1 i G2 je neovisno CRx ili N; Rx je vodik ili halogen; jedan od R1 i R2 je -OH, a preostali se bira iz skupine koju čine -C(O)Ra, -CH=NRj, -S(O)Rb, -S(O)2Rc, -NHC(O)Rd, -NHS(O)2Re, -C1-C6 alkil-Rf, -C2-C6 alkenil-Rg, nesupstituirani ili supstituirani C3-C8 cikloalkil, nesupstituirani ili supstituirani C3-C8 cikloalkenil, i nesupstituirani ili supstituirani heterocikloalkil; svaki od Ra, Rb, Rc i Re je neovisno H, C1-C6 alkil, C2-C6 alkenil, C2-C6 alkinil, C1-C6 haloalkil, nesupstituirani ili supstituirani heterociklil, nesupstituirani ili supstituirani heteroaril, benzoil, ili stiril; Rd je H, C1-C6 alkil, C2-C6 alkenil, C2-C6 alkinil, C1-C6 haloalkil, nesupstituirani ili supstituirani heterociklil, nesupstituirani ili supstituirani heteroaril, ili benzoil; svaki od Rf i Rg je neovisno -OH, nesupstituirani heteroaril, -NRmRn, benzoil, ili stiril; svaki od Rm i Rn je neovisno H, C1-C6 alkil, C2-C6 alkenil, C2-C6 alkinil, ili nesupstituirani ili supstituirani cikloalkil; Rj je nesupstituirani ili supstituirani heterociklil, nesupstituirani ili supstituirani aril, -ORk, -NHRk, -NHC(O)Rk, -NHS(O)2Rk, ili -NHC(NH)NH2; Rk je C1-C6 alkil, C2-C6 alkenil, C2-C6 alkinil, C3-C8 cikloalkil, ili aril; R3 je H, C1-C6 alkil, C1-C6 alkoksi, ili halogen, gdje je svaki C1-C6 alkil i C1-C6 alkoksi od R3, neovisno nesupstituiran ili supstituiran s jednim ili više halogena; pri čemu: kada R1 ili R2 je -C1-C6 alkil-OH ili -C1-C6 alkil-NRmRn, gdje svaki od Rm i Rn jest C1-C6 alkil, tada se R3 bira iz skupine koju čine C1-C6 alkil, C2-C6 alkoksi, i halogen; kada R1 ili R2 je nesupstituirani ili supstituirani C3-C8cikloalkil, -NHC(O)CH3, ili -S(O)2-Rc, gdje Rc je nesupstituirani ili supstituirani heterociklil, tada se R3 bira iz skupine koju čine C1-C6 alkil, C1-C6 alkoksi, i halogen; kada R1 ili R2 je -CHO, tada se R3 bira iz skupine koju čine vodik, C2-C6 alkoksi, i halogen; kada R1 ili R2 je -C(O)CH3, tada se R3 bira iz skupine koju čine C2-C6 alkoksi i halogen; kada R1 ili R2 je -C(O)CH(Br)CH3 ili -C(O)CH(Br)CH2CH3, tada G7 je C ili CH; kada R3 je vodik, ne više od jednog od R6a, R6b, R6c, i R6d je -CF3, ne više od jednog od R6a, R6b, R6c, i R6d je -CH3, i ne više od jednog od R6a, R6b, R6c, i R6d je -OH, Y je -C(O)- ili je izostavljen i svaki od R4 i R5 je H, ili Y je izostavljen te R4 i R5 dolaze zajedno za tvorbu -S-; G3 je CH(X1-R6a), C(X1-R6a), N, N(X1-R6a), S, ili O; G4 je CH(X2-R6b), C(X2-R6b), N, N(X2-R6b), S, ili O; G5 je CH(X3-R6c), C(X3-R6c), N, N(X3-R6c), S, ili O; G6 je CH(X4-R6d), C(X4-R6d), N, N(X4-R6d), S, ili O, ili je izostavljen; G7 je N, C, ili CH; pri čemu kada G5 je N, tada se primjenjuje najmanje jedno od (i), (ii), i (iii): (i) najmanje jedan od G3, G4, i G5, nije CH; (ii) R4 i R5 dolaze zajedno za tvorbu -S-; i (iii) R3 je -OCH3 ili halogen; svaki od X1, X2, X3, i X4 je neovisno izostavljen, m je 1-6; [image] svaki od R6a, R6b, R6c, i R6d je neovisno vodik, C1-C6 alkil, C1-C6 alkoksi, halogen, -OH, NRpRq, aril, heterociklil, heteroaril, -C1-C6 alkil-heterociklil, -OC(O)-heterociklil, -C(O)Rh, -S(O)2NRw1Rw2, S(O)2Ry, ili -NRz1S(O)2Rz2, gdje je svaki C1-C6 alkil, i C1-C6 alkoksi, od R6a, R6b, R6c, i R6d, neovisno nesupstituiran ili supstituiran s jednom ili više skupina odabranih iz skupine koju čine cikloalkil i halogen; svaki aril i heteroaril od R6a, R6b, R6c, i R6d je neovisno nesupstituiran ili supstituiran s jednom ili više skupina odabranih iz skupine koju čine C1-C6 alkil, C1-C6 alkoksi, -OH, i C1-C6 alkil-OH; i svaki heterociklil, -C1-C6 alkil-heterociklil, i -OC(O)-heterociklil od R6a, R6b, R6c, i R6d je neovisno nesupstituiran ili supstituiran s jednom ili više skupina odabranih iz skupine koju čine C1-C6 alkil, C1-C6 alkoksi, -OH, i -C1-C6 alkil-OH, =O, i =S; Rh se bira iz skupine koju čine H, C1-C6 alkil, C1-C6 alkoksi, i C3-C8 cikloalkil, i NRrRs; Rp je H ili C1-C6 alkil; Rq je C2-C3 alkil, -C(O)Rt, -C(O)ORu, -C(O)NRv; svaki od Rr, Rs, Rw1, i Rz1 se neovisno bira od H i C1-C6 alkila; i svaki od Rt, Ru, Rv, Rw2, Ry, i Rz2 se neovisno bira od H, C1-C6 alkila, nesupstituiranog ili supstituiranog C3-C8 cikloalkila, i nesupstituiranog ili supstituiranog heterociklila; ili G5 je CH(X3-R6c), ili C(X3-R6c), G6 je CH(X4-R6d), ili C(X4-R6d), i R6c i R6d se uzimaju zajedno s ugljicima s kojima su vezani, kako bi stvorili 6-člane prstene arila, heterociklila, ili heteroarila; pri čemu je svaki od 6-članog prstena arila, 6-članog prstena heterociklila, i 6-članog prstena heteroarila, neovisno nesupstituiran ili supstituiran; gdje ne više od jednoga od R6a, R6b, R6c, i R6d je C1-C6 alkoksi ili -OH; i pritom spoj nije spoj koji se bira od sljedećih: [image] [image] [image]
2. Spoj prema patentnom zahtjevu 1, ili njegov tautomer, ili farmaceutski prihvatljiva sol od bilo kojega predstojećeg, naznačen time, da Y je izostavljen.
3. Spoj prema patentnom zahtjevu 1 ili 2, ili njegov tautomer, ili farmaceutski prihvatljiva sol od bilo kojega predstojećeg, naznačen time, da svaki od G1 i G2 je CRx.
4. Spoj prema bilo kojem od patentnih zahtjeva 1-3, ili njegov tautomer, ili farmaceutski prihvatljiva sol od bilo kojega predstojećeg, naznačen time, da svaki od G1 i G2 je CH.
5. Spoj prema bilo kojem od patentnih zahtjeva 1-4, ili njegov tautomer, ili farmaceutski prihvatljiva sol od bilo kojega predstojećeg, naznačen time, da: R1 je -OH; i R2 se bira iz skupine koju čine -C(O)Ra, -S(O)2Rc, -NHC(O)Rd, -NHS(O)2Re, -C2-C6 alkenil-Rg, i nesupstituiran ili supstituiran cikloalkenil.
6. Spoj prema bilo kojem od patentnih zahtjeva 1-4, ili njegov tautomer, ili farmaceutski prihvatljiva sol od bilo kojega predstojećeg, naznačen time, da: R1 je -OH; i R2 je -CH=NRj, gdje Rj je nesupstituirani ili supstituirani heterociklil, nesupstituirani ili supstituirani aril, -ORk, -NHRk, -NHC(O)Rk, -NHS(O)2Rk, ili -NHC(NH)NH2.
7. Spoj prema bilo kojem od patentnih zahtjeva 1-4, ili njegov tautomer, ili farmaceutski prihvatljiva sol od bilo kojega predstojećeg, naznačen time, da: R1 je -OH; i R2 se bira iz skupine koju čine -CHO, -C(O)CH3, -C(O)CH2F, -C(O)CH=CH2, -S(O)2CH=CH2, -C(O)C≡CH, -C(O)C≡CCH3, -NHS(O)2CH=CH2, -NHC(O)CH=CH2, -C(O)C(=CH2)CH3, [image] [image] [image] [image] [image] [image]
8. Spoj prema bilo kojem od patentnih zahtjeva 1-7, ili njegov tautomer, ili farmaceutski prihvatljiva sol od bilo kojega predstojećeg, naznačen time, da se R3 bira iz skupine koju čine C1-C6 alkil, C1-C6 alkoksi, i halogen.
9. Spoj prema bilo kojem od patentnih zahtjeva 1-8, ili njegov tautomer, ili farmaceutski prihvatljiva sol od bilo kojega predstojećeg, naznačen time, da se R3 bira iz skupine koju čine -OCH3 ili F.
10. Spoj prema bilo kojem od patentnih zahtjeva 1-9, ili njegov tautomer, ili farmaceutski prihvatljiva sol od bilo kojega predstojećeg, naznačen time, da svaki od R4 i R5 jest H.
11. Spoj prema bilo kojem od patentnih zahtjeva 1-9, ili njegov tautomer, ili farmaceutski prihvatljiva sol od bilo kojega predstojećeg, naznačen time, da R4 i R5 dolaze zajedno kako bi stvorili -S-.
12. Spoj prema bilo kojem od patentnih zahtjeva 1-11, ili njegov tautomer, ili farmaceutski prihvatljiva sol od bilo kojega predstojećeg, naznačen time, da: G5 je CH(X3-R6c) ili C(X3-R6c), G6 je CH(X4-R6d) ili C(X4-R6d), i R6c i R6d se uzimaju zajedno s ugljicima s kojima su vezani, kako bi stvorili 6-člani prsten arila, 6-člani prsten heterociklila, ili 6-člani prsten heteroarila; pri čemu je svaki od 6-članog prstena arila, 6-članog prstena heterociklila, i 6-članog heteroarila, neovisno nesupstituiran ili supstituiran.
13. Spoj prema bilo kojem od patentnih zahtjeva 1-12, ili njegov tautomer, ili farmaceutski prihvatljiva sol od bilo kojega predstojećeg, naznačen time, da G7 je C ili CH.
14. Spoj prema bilo kojem od patentnih zahtjeva 1-13, ili njegov tautomer, ili farmaceutski prihvatljiva sol od bilo kojega predstojećeg, naznačen time, da: G4 je CH(X2-R6b) ili C(X2-R6b); X2 je izostavljen; m je 1-6; R6b je vodik, C1-C6 alkil, C1-C6 alkoksi, halogen, ili -C(O)Rh, gdje C1-C6 alkil je nesupstituiran ili supstituiran sa cikloalkilom ili halogenom; i Rh se bira iz skupine koju čine H, C1-C6 alkil, C1-C6 alkoksi, ili C3-C8 cikloalkil.
15. Spoj prema bilo kojem od patentnih zahtjeva 1-14, ili njegov tautomer, ili farmaceutski prihvatljiva sol od bilo kojega predstojećeg, naznačen time, da: G5 je CH(X3-R6c) ili C(X3-R6c); X3 je izostavljen; m je 1-6; R6c je vodik, C1-C6 alkil, C1-C6 alkoksi, halogen, ili -C(O)Rh, gdje C1-C6 alkil je nesupstituiran ili supstituiran sa cikloalkilom ili halogenom; i Rh se bira iz skupine koju čine H, C1-C6 alkil, C1-C6 alkoksi, ili C3-C8 cikloalkil.
16. Spoj prema bilo kojem od patentnih zahtjeva 1-15, ili njegov tautomer, ili farmaceutski prihvatljiva sol od bilo kojega predstojećeg, naznačen time, da: G6 je CH(X4-R6d) ili C(X4-R6d); X4 je izostavljen; m je 1-6; R6d je vodik, C1-C6 alkil, C1-C6 alkoksi, halogen, ili -C(O)Rh, gdje C1-C6 alkil je nesupstituiran ili supstituiran sa cikloalkilom ili halogenom; i Rh se bira iz skupine koju čine H, C1-C6 alkil, C1-C6 alkoksi, ili C3-C8 cikloalkil.
17. Spoj prema bilo kojem od patentnih zahtjeva 1-16, ili njegov tautomer, ili farmaceutski prihvatljiva sol od bilo kojega predstojećeg, naznačen time, da: svaki od R6a, R6b, R6c, i R6d je neovisno vodik, C1-C6 alkil, C1-C6 alkoksi, halogen, ili -C(O)Rh, gdje C1-C6 alkil je nesupstituiran ili supstituiran sa cikloalkilom ili halogenom; i Rh se bira iz skupine koju čine H, C1-C6 alkil, C1-C6 alkoksi, ili C3-C8 cikloalkil.
18. Spoj prema patentnom zahtjevu 1, naznačen time, da se bira od sljedećih spojeva, ili njegov tautomer, ili farmaceutski prihvatljiva sol od bilo kojega predstojećeg: [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image]
19. Farmaceutski pripravak, naznačen time, da sadrži najmanje jedan spoj u skladu s bilo kojim od patentnih zahtjeva 1-18, ili njegov tautomer, ili farmaceutski prihvatljivu sol od bilo kojega predstojećeg, te opcionalno nadalje sadrži farmaceutski prihvatljivo pomoćno sredstvo.
20. Spoj prema bilo kojem od patentnih zahtjeva 1-18, ili njegov tautomer, ili farmaceutski prihvatljiva sol od bilo kojega predstojećeg, naznačen time, da je za uporabu u postupku liječenja bolesti ili stanja koje je povezano s heterodimerizacijom TLR2, pri čemu se bolest ili stanje bira iz skupine koju čine: Alzheimerova bolest, Parkinsonova bolest, fronto-temporalna demencija, demencija s Lewyjevim tjelešcima (bolest Lewyjevih tijela), Parkinsonova bolest s demencijom, višestruka sustavna atrofija, amiotrofična lateralna skleroza, Huntingtonova bolest, progresivna supranuklearna paraliza (PSP), Niemann-Pickova bolest tipa C, upalne bolesti, astma, kronična opstrukcijska plućna bolest (KOPB), kronični peptički ulkusi, iritabilna bolest crijeva, tuberkuloza, reumatoidni artritis, osteoartritis, kronični sinusitis, hepatitis, hepatitis B, hepatitis C, giht, lupus, pleuritis, ekcem, gastritis, psorijaza, psorijatički artritis, vaskulitis, laringitis, alergijske reakcije, multipla skleroza, Crohnova bolest, traumatska ozljeda mozga, CIDP (kronična upalna demijelinacijska polineuropatija), moždani udar, ishemijska srčana bolest, atopijski dermatitis, akne vulgaris, rozacea, nealkoholna bolest masne jetre, nealkoholni steatohepatitis, ozljede rožnice, poremećaji rožnice, HSV rožnice, Stargardtova bolest (mladenačka makularna degeneracija), starosna makularna degeneracija, sepsa, dijabetičke rane, virus herpes simpleks, i anti-gljivične, anti-bakterijske, antivirusne i antitumorske bolesti ili stanja.
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