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HRP20180324T1 - Supstituirani derivati 2-[2-(fenil)etilamino]alkanamida i njihova upotreba kao modulatora natrijevih i/ili kalcijevih kanala - Google Patents

Supstituirani derivati 2-[2-(fenil)etilamino]alkanamida i njihova upotreba kao modulatora natrijevih i/ili kalcijevih kanala Download PDF

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Publication number
HRP20180324T1
HRP20180324T1 HRP20180324TT HRP20180324T HRP20180324T1 HR P20180324 T1 HRP20180324 T1 HR P20180324T1 HR P20180324T T HRP20180324T T HR P20180324TT HR P20180324 T HRP20180324 T HR P20180324T HR P20180324 T1 HRP20180324 T1 HR P20180324T1
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HR
Croatia
Prior art keywords
ethylamino
alkyl
compound
hydrogen
butoxyphenyl
Prior art date
Application number
HRP20180324TT
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English (en)
Inventor
Piero Melloni
Alessandra Restivo
Emanuela Izzo
Simona Francisconi
Elena Colombo
Cibele Sabido-David
Original Assignee
Newron Pharmaceuticals S.P.A.
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Publication date
Application filed by Newron Pharmaceuticals S.P.A. filed Critical Newron Pharmaceuticals S.P.A.
Publication of HRP20180324T1 publication Critical patent/HRP20180324T1/hr
Publication of HRP20180324T8 publication Critical patent/HRP20180324T8/hr

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Claims (34)

1. Spoj opće formule (I): [image] (I) u kojoj: X je -O-, -S- ili -SO2-; Y je vodik, OH ili O(C1-C4)alkil; Z je =O ili =S; R je (C3-C10)alkil; ω-trifluor(C3-C10)alkil; R1 i R2 jesu, neovisno, vodik, hidroksi, (C1-C8)alkoksi, (C1-C8)alkiltio, halogen, trifluormetil ili 2,2,2-trifluoretil; ili jedan od R1 i R2 je u ortho-položaju prema R-X- i, uzet zajedno s istim R-X-, predstavlja skupinu [image] u kojoj R0 jest (C2-C9)alkil; R3 i R’3 jesu, neovisno, vodik ili (C1-C4)alkil; R4 i R5 jesu, neovisno, vodik, (C1-C4)alkil; ili R4 je vodik te R5 je skupina odabrana od -CH2-OH, -CH2-O-(C1-C6)alkil, -CH(CH3)-OH, -(CH2)2-S-CH3, benzil i 4-hidroksibenzil; ili R4 i R5, uzeti zajedno sa susjednim ugljikovim atomom, tvore (C3-C6)cikloalkilni ostatak; R6 i R7 jesu neovisno vodik ili (C1-C6)alkil; ili uzeti zajedno sa susjednim dušikovim atomom tvore peteročlani ili šesteročlani monociklički zasićeni heterociklički prsten, koji može sadržavati jedan dodatni heteroatom odabran od -O-, -S- i -NR8- gdje R8 je vodik ili (C1-C6)alkil; pod uvjetom da kada X jest -S- ili -SO2-, tada Y nije OH ili O(C1-C4)alkil; u kojem slučaju, može biti jedan optički izomer u izoliranom obliku ili njegova smjesa u bilo kojem omjeru i njegove farmaceutski prihvatljive soli.
2. Spoj iz patentnog zahtjeva 1 naznačeno time da: X je -O-, -S-; Y je vodik, OH ili O(C1-C3)alkil; Z je =O ili =S; R je (C4-C7)alkil ili ω-trifluor(C4-C6)alkil; R1 i R2 jesu, neovisno, vodik, (C1-C4)alkoksi, halogen, trifluormetil ili 2,2,2-trifluoretil; ili jedan od R1 i R2 je u ortho-položaju prema R-X- i, uzet zajedno s istim R-X-, predstavlja skupinu [image] u kojoj R0 jest (C2-C5)alkil; R3 i R’3 jesu, neovisno, vodik ili (C1-C3)alkil; R4 i R5 jesu, neovisno, vodik ili (C1-C4)alkil; ili R4 je vodik te R5 je skupina odabrana od -CH2-OH, -CH2-O-(C1-C3)alkil, -(CH2)2-S-CH3, benzil i 4-hidroksibenzil; R6 i R7 jesu, neovisno, vodik ili (C1-C4)alkil; ili uzeti zajedno sa susjednim dušikovim atomom tvore peteročlani ili šesteročlani monociklički zasićeni heterociklički prsten, koji može sadržavati jedan dodatni heteroatom odabran od -O- i -NR8- gdje R8 je vodik ili (C1-C3)alkil; pod uvjetom da kada X jest -S-, tada Y nije OH ili O(C1-C3)alkil; u kojem slučaju, može biti jedan optički izomer u izoliranom obliku ili njegova smjesa u bilo kojem omjeru i njegove farmaceutski prihvatljive soli.
3. Spoj iz patentnog zahtjeva 1 naznačeno time da: X je -O-, -S-; Y je vodik ili O(C1-C3)alkil; Z je =O ili =S; R je (C4-C7)alkil ili ω-trifluor(C4-C6)alkil; R1 i R2 jesu, neovisno, vodik, (C1-C3)alkoksi, fluor, klor, trifluormetil ili 2,2,2-trifluoretil; ili jedan od R1 i R2 je u ortho-položaju prema R-X- i uzet zajedno s istim R-X-, predstavlja skupinu [image] u kojoj R0 jest (C3-C4)alkil; R3 i R’3 jesu, neovisno, vodik ili (C1-C3)alkil; R4 i R5 jesu, neovisno, vodik ili (C1-C4)alkil; ili R4 je vodik te R5 je skupina odabrana od -CH2-OH, -CH2-O-(C1-C3)alkil, benzil i 4-hidroksibenzil; R6 i R7 jesu, neovisno, vodik ili (C1-C3)alkil; ili uzeti zajedno sa susjednim dušikovim atomom tvore peteročlani ili šesteročlani monociklički zasićeni heterociklički prsten, koji može sadržavati jedan dodatni heteroatom odabran od -O- i -NR8-, gdje R8 je vodik ili (C1-C3)alkil; pod uvjetom da kada X jest -S-, tada Y nije O(C1-C3)alkil; u kojem slučaju, može biti jedan optički izomer u izoliranom obliku ili njegova smjesa u bilo kojem omjeru i njegove farmaceutski prihvatljive soli.
4. Spoj iz patentnog zahtjeva 1 naznačeno time da: X je -O-; Y je vodik; Z je =O; R je (C4-C6)alkil; R1 i R2 jesu, neovisno, vodik ili halogen, preferirano fluor; R3, R’3, R4 i R5 su vodik; R6 i R7 jesu, neovisno, vodik ili (C1-C3)alkil; u kojem slučaju, može biti jedan optički izomer u izoliranom obliku ili njegova smjesa u bilo kojem omjeru i njegove farmaceutski prihvatljive soli.
5. Spoj iz patentnog zahtjeva 1 naznačeno time da je odabran od: 2-[2-(3-butoksifenil)-etilamino]-acetamid 2-[2-(3-pentiloksifenil)-etilamino]-acetamid 2-[2-(3-heksiloksifenil)-etilamino]-acetamid 2-[2-(3-butoksifenil)-etilamino]-N-metilacetamid 2-[2-(3-pentiloksifenil)-etilamino]-N-metilacetamid 2-[2-(3-heksiloksifenil)-etilamino]-N-metilacetamid 2-[2-(3-butoksifenil)-etilamino]-N,N-dimetilacetamid 2-[2-(3-butilsulfonilfenil)-etilamino]-N,N-dimetilacetamid 2-[2-(3-butoksifenil)-(N’-hidroksi)etilamino]-N,N-dimetilacetamid 2-[2-(3-butoksifenil)-(N’-metoksi)etilamino]-N,N-dimetilacetamid 2-[2-(3-butoksifenil)-(N’-propoksi)etilamino]-N,N-dimetilacetamid 2-[2-(3-butoksifenil)-etilamino]-N,N-dimetil-tioacetamid 2-[2-(3-butoksifenil)-2-metilpropilamino]-N,N-dimetilacetamid 2-{2-[3-(4,4,4-trifluorbutoksi)fenil]-etilamino}-N,N-dimetilacetamid 2-[2-(3-butiltiofenil)-etilamino]-N,N-dimetilacetamid 2-[2-(3-butoksi-2-klorfenil)-etilamino]-N,N-dimetilacetamid 2-[2-(3-butoksi-2-fluorfenil)-etilamino]-N,N-dimetilacetamid 2-[2-(3-butoksi-4-metoksifenil)-etilamino]-N,N-dimetilacetamid 2-[2-(3-butoksifenil)-etilamino]-N,N-dietilacetamid 2-[2-(3-butoksifenil)-etilamino]-N,N-dipropilacetamid 2-[2-(3-butoksifenil)-etilamino]-N,N-dibutilacetamid 2-[2-(3-pentiloksifenil)-etilamino]-N,N-dimetilacetamid 2-[2-(3-heksiloksifenil)-etilamino]-N,N-dimetilacetamid 2-[2-(3-butoksifenil)-etilamino]-1-pirolidin-1-il-etan-1-on 2-[2-(3-pentiloksifenil)-etilamino]-1-pirolidin-1-il-etan-1-on 2-[2-(3-heksiloksifenil)-etilamino]-1-pirolidin-1-il-etan-1-on 2-[2-(3-butoksifenil)-etilamino]-N,N-dimetilpropanamid 2-[2-(3-butoksifenil)-etilamino]-3-hidroksi-N,N-dimetilpropanamid 2-[2-(3-butoksifenil)-etilamino]-3-metoksi-N,N-dimetilpropanamid 2-[2-(3-butoksifenil)-etilamino]-3-propoksi-N,N-dimetilpropanamid 2-[2-(3-butoksifenil)-etilamino]-2,N,N-trimetilpropanamid 2-[2-(3-pentiloksifenil)-etilamino]-2,N,N-trimetilpropanamid 2-[2-(3-heksiloksifenil)-etilamino]-2,N,N-trimetilpropanamid (S)-2-[2-(3-butoksifenil)-etilamino]-propanamid (S)-2-[2-(3-butoksifenil)-etilamino]-N-metilpropanamid (S)-2-[2-(3-butoksifenil)-etilamino]-N,N-dimetilpropanamid (R)-2-[2-(3-butoksifenil)-etilamino]-propanamid (R)-2-[2-(3-butoksifenil)-etilamino]-N-metilpropanamid (R)-2-[2-(3-butoksifenil)-etilamino]-N,N-dimetilpropanamid 2-[2-(3-butoksi-2-trifluormetilfenil)-etilamino]-N,N-dimetilacetamid 2-[2-(3-butoksi-4-trifluormetilfenil)-etilamino]-N,N-dimetilacetamid 2-[2-(3-butoksi-5-trifluormetilfenil)-etilamino]-N,N-dimetilacetamid u kojem slučaju, može biti jedan optički izomer u izoliranom obliku ili njegova smjesa u bilo kojem omjeru i njegove farmaceutski prihvatljive soli, preferirano njegova sol s klorovodičnom ili metansulfonskom kiselinom.
6. Spoj iz patentnog zahtjeva 1 naznačeno time da je 2-[2-(3-butoksifenil)-etilamino]-N,N-dimetilacetamid, 2-[2-(3-butoksi-2,6-difluorfenil)-etilamino]-N,N-dimetilacetamid, 2-[2-(3-pentiloksifenil)-etilamino]-N,N-dimetilacetamid, ili 2-[2-(3-heksiloksifenil)-etilamino]-N,N-dimetilacetamid, i njihove farmaceutski prihvatljive soli.
7. Spoj iz patentnog zahtjeva 6 naznačeno time da je 2-[2-(3-butoksifenil)-etilamino]-N,N-dimetilacetamid ili njegova farmaceutski prihvatljiva sol.
8. Spoj iz bilo kojeg od patentnih zahtjeva 6 i 7 naznačeno time da farmaceutski prihvatljiva sol jest hidroklorid ili metansulfonat.
9. Spoj iz patentnog zahtjeva 1 naznačeno time da: X je -SO2-; ili Y je OH ili O(C1-C4)alkil; ili Z je =S; ili R je (C9-C10)alkil ili ω-trifluor(C3-C10)alkil; ili R1 i/ili R2 su različiti od vodika; ili oba R3 i R'3 su različiti od vodika; ili oba R4 i R5 su različiti od vodika, ali kad su uzeti zajedno sa susjednim ugljikovim atomom ne tvore (C3-C6)cikloalkilni ostatak; ili R6 i R7, uzeti zajedno sa susjednim dušikovim atomom tvore monociklički peteročlani ili šesteročlani zasićeni heterociklički prsten, koji može sadržavati jedan dodatni heteroatom odabran od -O-, -S- i -NR8-, gdje R8 je vodik ili (C1-C6)alkil; pod uvjetom da kada X jest -S- ili -SO2-, tada Y nije OH ili O(C1-C4)alkil; u kojem slučaju, može biti jedan optički izomer u izoliranom obliku ili njegova smjesa u bilo kojem omjeru i njegove farmaceutski prihvatljive soli.
10. Spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 za upotrebu kao lijek.
11. Spoj iz patentnog zahtjeva 1 za upotrebu kao lijek aktivan kao modulator natrijevih i/ili kalcijevih kanala za liječenje patologija u kojima gore rečeni mehanizam (mehanzimi) igra (igraju) patološku ulogu, koja je neurološki, kognitivni, psihijatrijski, upalni, urogenitalni ili gastrointestinalni poremećaj, a rečeni lijek uopće nema MAO inhibitorsku aktivnost ili ima znatno smanjenu MAO inhibitorsku aktivnost.
12. Spoj iz bilo kojeg od patentnih zahtjeva 2, 3 i 4 za upotrebu prema patentnom zahtjevu 11.
13. Spoj iz patentnog zahtjeva 5 za upotrebu prema patentnom zahtjevu 11.
14. Spoj iz patetnog zahtjeva 6 za upotrebu prema patentnom zahtjevu 11.
15. Spoj iz patentnog zahtjeva 7 za upotrebu prema patentnom zahtjevu 11.
16. Spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 za upotrebu prema patentnom zahtjevu 11, pri čemu poremećaj jest neurološki poremećaj odabran od boli i migrene.
17. Spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 za upotrebu prema patentnom zahtjevu 16 pri čemu bol jest sindrom neuropatske boli ili sindrom upalne boli.
18. Spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 za upotrebu prema patentnom zahtjevu 16 pri čemu bol jest akutna ili kronična bol.
19. Spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 za upotrebu prema patentnom zahtjevu 11, pri čemu poremećaj jest neurološki poremećaj odabran od Alzheimerove bolesti, Parkinsonove bolesti, epilepsije, sindroma nemirnih nogu, moždanog udara ili cerebralne ishemije.
20. Spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 za upotrebu prema patentnom zahtjevu 11, pri čemu poremećaj jest upalni proces koji djeluje na sve sustave tijela odabran od artritičnog stanja, poremećaja koji djeluje na kožu i pripadajuća tkiva, poremećaja respiratornog sustava ili poremećaja imunološkog i endokrinološkog sustava.
21. Spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 za upotrebu prema patentnom zahtjevu 11, pri čemu poremećaj jest kognitivni i/ili psihijatrijski poremećaj odabran od blagog kognitivnog oštećenja, depresije, bipolarnog poremećaja, manije, shizofrenije, psihoze, anksioznosti i ovisnosti.
22. Spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 za upotrebu prema patentnom zahtjevu 11, pri čemu poremećaj jest urogenitalni poremećaj.
23. Spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 za upotrebu prema patentnom zahtjevu 11, pri čemu poremećaj jest gastrointestinalni poremećaj.
24. Spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 za upotrebu prema bilo kojem od patentnih zahtjeva 11 i 16 do 23, pri čemu je rečeni spoj kombiniran s jednim ili više drugih terapeutskih sredstava.
25. Farmaceutski pripravak koji sadrži, kao aktivnu tvar, spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 zajedno s farmaceutski prihvatljivim terapeutski inertnim organskim ili anorganskim materijalima za nosač.
26. Spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 za upotrebu prema patentnom zahtjevu 21, pri čemu je rečeni spoj kombiniran s jednim ili više drugih terapeutskih sredstava prema patentnom zahtjevu 24, pri čemu je drugo terapeutsko sredstvo tipično ili atipično antipsihotičko sredstvo.
27. Spoj iz patentnog zahtjeva 26 naznačeno time da tipično antipsihotičko sredstvo jest haloperidol, a atipično antipsihotičko sredstvo odabrano je od risperidona i klozapina.
28. Spoj iz patentnog zahtjeva 26, naznačeno time da rečeni spoj jest 2-[2-(3-butoksifenil)-etilamino]-N,N-dimetilacetamid ili njegova farmaceutski prihvatljiva sol, tipično antipsihotičko sredstvo jest haloperidol, a atipično antipsihotičko sredstvo odabrano je od risperidona i klozapina.
29. Spoj iz patentnog zahtjeva 26, naznačeno time da rečeni spoj jest hidroklorid ili metansulfonat 2-[2-(3-butoksifenil)-etilamino]-N,N-dimetilacetamida te tipično antipsihotičko sredstvo jest haloperidol, a atipično antipsihotičko sredstvo odabrano je od risperidona i klozapina.
30. Spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 za upotrebu prema patentnom zahtjevu 20, pri čemu poremećaj jest poremećaj imunološkog sustava.
31. Spoj iz patentnog zahtjeva 30, naznačeno time da poremećaj imunološkog sustava jest multipla skleroza ili drugi demijelinizirajući poremećaji.
32. Spoj iz bilo kojeg od patentnih zahtjeva 1 do 9 za upotrebu prema bilo kojem od patentnih zahtjeva 11 do 24 i 26 do 31 gdje su pacijenti koji pate od poremećaja (poremećaja) posebno osjetljivi na neželjene nuspojave zbog MAO inhibitorske aktivnosti.
33. Upotreba spoja iz bilo kojeg od patentnih zahtjeva 1 do 9 za pripravu lijeka aktivnog kao modulator natrijevog i/ili kalcijevog kanala za liječenje patologija u kojima gore rečeni mehanizam (mehanizimi) igra (igraju) patološku ulogu, koja je neurološki, kognitivni, psihijatrijski, upalni, urogenitalni ili gastrointestinalni poremećaj, a rečeni lijek uopće nema MAO inhibitorsku aktivnost ili ima znatno smanjenu MAO inhibitorsku aktivnost.
34. Upotreba prema patentnom zahtjevu 33 pri čemu poremećaj jest kao u bilo kojem od patentnih zahtjeva 16 do 23.
HRP20180324TT 2007-06-15 2008-05-14 Supstituirani derivati 2-[2-(fenil)etilamino]alkanamida i njihova upotreba kao modulatora natrijevih i/ili kalcijevih kanala HRP20180324T8 (hr)

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