SI2155663T1 - Substituirani 2-(2-(fenil)etilamino)alkanamidni derivati in njihova uporaba kot modulatorji natrijevega in/ali kalcijevega kanala - Google Patents

Substituirani 2-(2-(fenil)etilamino)alkanamidni derivati in njihova uporaba kot modulatorji natrijevega in/ali kalcijevega kanala Download PDF

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SI2155663T1
SI2155663T1 SI200831914T SI200831914T SI2155663T1 SI 2155663 T1 SI2155663 T1 SI 2155663T1 SI 200831914 T SI200831914 T SI 200831914T SI 200831914 T SI200831914 T SI 200831914T SI 2155663 T1 SI2155663 T1 SI 2155663T1
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Slovenia
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ethylamino
alkyl
dimethylacetamide
disorder
butoxyphenyl
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SI200831914T
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Piero Melloni
Alessandra Restivo
Emanuela Izzo
Simona Francisconi
Elena Colombo
Cibele Sabido-David
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Newron Pharmaceuticals S.P.A.
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Publication of SI2155663T1 publication Critical patent/SI2155663T1/sl

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Claims (34)

  1. Substituirani 2-[2-(fenil)etilamino]alkanamidni derivati in njihova uporaba kot modulatorji natrijevega in/ali kalcijevega kanala Patentni zahtevki
    1. Spojina s splošno formulo (I):
    v kateri: X je -O-, -S- ali -SO2-; Y je vodik, OH ali 0(Ci-C4)alkil; Z je =0 ali =S; R je (C3-Cio)alkil; u)-trifluoro(C3-Cio)alkil; R1 in R2 sta neodvisno vodik, hidroksi, (Ci-Cejalkoksi, (CrCe) alkiltio, halo, trifluorometil ali 2,2,2-trifluoroetil; ali je eden od R1 in R2 v orto položaju na R-X-in vzet skupaj z istim R-X- pomeni skupino kjer je R0 (C2-Cg)alkil;
    R3 in R'3 sta neodvisno vodik ali (Ci-C4)alkil; R4 in R5 sta neodvisno vodik, (Ci-C4)alkil; ali je R4 vodik in je R5 skupina, izbrana med -CH2-OH, >CH2-0-(Ci-C6)alkilom, -CH(CH3)-OH, -(CH2)2-S-CH3, benzilom in 4-hidroksibenzilom; ali R4 in R5 vzeta skupaj s sosednjim atomom ogljika tvorita (C3-C6)cikloalkilni ostanek; R6 in R7 sta neodvisno vodik ali (Ci-C6)alkil; ali vzeta skupaj s sosednjim atomom dušika tvorita 5-6-členski monocikličen nasičen heterocikel, ki po izbiri vsebuje en dodaten heteroatom, izbran med -O-, -S- in -NR8-, kjer je R8 vodik ali (Ci-C6)alkil; pod pogojem, da, kadar je X -S- ali -SO2-, potem Y ni OH ali 0(Ci-C4)alkil; v takšnem primeru bodisi kot posamičen optični izomer v izolirani obliki ali zmes le-teh v kakršnem koli razmerju in njene farmacevtsko sprejemljive soli.
  2. 2. Spojina po zahtevku 1, v kateri: X je -0-, -S-; Y je vodik, OH ali 0(C-i-C3)alkil; Z je =0 ali =S; R je (C4-C7)alkil ali (jo-trifluoro(C4-C6)alkil; R1 in R2 sta neodvisno vodik, (Ci-C4)alkoksi, halo, trifluorometil ali 2,2,2-trifluoroetil; ali je eden od R1 in R2 v orto položaju na R-X- in vzet skupaj z istim R-X- pomeni skupino kjer je Ro (C2-C5)alkil;
    R3 in R'3 sta neodvisno vodik ali (Ci-C3)alkil; R4 in R5 sta neodvisno vodik, (Ci-C4)alkil; ali je R4 vodik in je R5 skupina, izbrana med -CH2-OH, -CH2-0-(Ci-C3)alkilom, -(CH2)2-S-CH3, benzilom in 4-hidroksibenzilom; R6 in R7 sta neodvisno vodik ali (Ci-C4)alkil; ali vzeta skupaj s sosednjim atomom dušika tvorita 5-6-členski monocikličen nasičen heterocikel, ki po izbiri vsebuje en dodaten heteroatom, izbran med -O- in -NR8-, kjer je R8 vodik ali (Ci-C3)alkil; pod pogojem, da, kadar je X -S-, potem Y ni OH ali 0(Ci-C3)alkil; v takšnem primeru bodisi kot posamičen optični izomer v izolirani obliki ali zmes le-teh v kakršnem koli razmerju in njene farmacevtsko sprejemljive soli.
  3. 3. Spojina po zahtevku 1, v kateri: X je -Ο-, -S-; Y je vodik ali 0(Ci-C3)alkil; Z je =0 ali =S; R je (C4-C7)alkil ali u)-trifluoro(C4-C6)alkil; Ri in R2 sta neodvisno vodik, (Ci-C3)alkoksi, fluoro, kloro, trifluorometil ali 2,2,2-trifluoroetil; ali je eden od R1 in R2 v orto položaju na R-X- in vzet skupaj z istim R-X- pomeni skupino
    kjer je R0 (C3-C4)alkil; R3 in R'3 sta neodvisno vodik ali (CrC3)alkil; R4 in R5 sta neodvisno vodik ali (Ci-C4)alkil; ali je R4 vodik in je R5 skupina, izbrana med -CH2-OH, -CH2-0-(Ci-C3)alkilom, benzilom in 4-hidroksibenzilom; R6 in R7 sta neodvisno vodik ali (CrC3)alkil; ali vzeta skupaj s sosednjim atomom dušika tvorita 5-6-členski monocikličen nasičen heterocikel, ki po izbiri vsebuje en dodaten heteroatom, izbran med -O- in -NRe-, kjer je Re vodik ali (C1-C3) alkil; pod pogojem, da, kadar je X -S-, potem Y ni 0(CrC3)alkil; v takšnem primeru bodisi kot posamičen optični izomer v izolirani obliki ali zmes le-teh v kakršnem koli razmerju in njene farmacevtsko sprejemljive soli.
  4. 4. Spojina po zahtevku 1, v kateri: X je -ΟΥ je vodik; Z je =0; R je (C4-C6)alkil; R1 in R2 sta neodvisno vodik ali halo, prednostno fluoro; R3, R3, R4 in R5 so vodik; R6 in R7 sta neodvisno vodik ali (Ci-C3)alkil; v takšnem primeru bodisi kot posamičen optični izomer v izolirani obliki ali zmes le-teh v kakršnem koli razmerju in njene farmacevtsko sprejemljive soli.
  5. 5. Spojina po zahtevku 1, izbrana med: 2-[2-(3-butoksifenil)-etilamino]-acetamidom 2-[2-(3-pentiloksifenil)-etilamino]-acetamidom 2-[2-(3-heksiloksifenil)-etilamino]-acetamidom 2-[2-(3-butoksifenil)-etilamino]-N-metilacetamidom 2-[2-(3-pentiloksifenil)-etilamino]-N-metilacetamidom 2-[2-(3-heksiloksifenil)-etilamino]-N-metilacetamidom 2-[2-(3-butoksifenil)-etilamino]-N,N-dimetilacetamidom 2-[2-(3-butilsulfonilfenil)-etilamino]-N,N-dimetilacetamidom 2-[2-(3-butoksifenil)-(N'-hidroksi)etilamino]-N,N-dimetilacetamidom 2-[2-(3-butoksifenil)- (N'-metoksi)etilamino]-N,N-dimetilacetamidom 2-[2-(3-butoksifenil)- (N'-propoksi)etilamino]-N,N-dimetilacetamidom 2-[2-(3-butoksifenil)-etilamino]-N,N-dimetil-tioacetamidom 2-[2-(3-butoksifenil)-2-metilpropilamino]-N,N-dimetilacetamidom 2-{2-[3-(4,4,4-trifluorobutoksi)fenil]-etilamino}-N,N-dimetilacetamidom 2-[2-(3-butiltiofenil)-etilamino]-N,N-dimetilacetamidom 2-[2-(3-butoksi-2-klorofenil)-etilamino]-N,N-dimetilacetamidom 2-[2-(3-butoksi-2-fluorofenil)-etilamino]-N,N-dimetilacetamidom 2-[2-(3-butoksi-4-metoksifenil)-etilamino]-N,N-dimetilacetamidom 2-[2-(3-butoksifenil)-etilamino]-N,N-dietilacetamidom 2-[2-(3-butoksifenil)-etilamino]-N,N-dipropilacetamidom 2-[2-(3-butoksifenil)-etilamino]-N,N-dibutilacetamidom 2-[2-(3-pentiloksifenil)-etilamino]-N,N-dimetilacetamidom 2-[2-(3-heksiloksifenil)-etilamino]-N,N-dimetilacetamidom 2-[2-(3-butoksifenil)-etilamino]-1 -pirolidin-1 -il-etan-1 -onom 2-[2-(3-pentiloksifenil)-etilamino]-1 -pirolidin-1 -il-etan-1 -onom 2-[2-(3-heksiloksifenil)-etilamino]-1 -pirolidin-1 -il-etan-1 -onom 2-[2-(3-butoksifenil)-etilamino]- N.N-dimetilpropanamidom 2-[2-(3-butoksifenil)-etilamino]-3-hidroksi-N,N-dimetilpropanamidom 2-[2-(3-butoksifenil)-etilamino]-3-metoksi-N,N-dimetilpropanamidom 2-[2-(3-butoksifenil)-etilamino]-3-propoksi-N,N-dimetilpropanamidom 2-[2-(3-butoksifenil)-etilamino]-2,N)N-trimetilpropanamidom 2-[2-(3-pentiloksifenil)-etilamino]-2,N,N-trimetilpropanamidom 2-[2-(3-heksiloksifenil)-etilamino]-2,N,N-trimetilpropanamidom (S)-2-[2-(3-butoksifenil)-etilamino]-propanamidom (S)-2-[2-(3-butoksifenil)-etilamino]-N-metilpropanamidom (S)-2-[2-(3-butoksifenil)-etilamino]-N,N-dimetilpropanamidom (R)-2-[2-(3-butoksifenil)-etilamino]-propanamidom (R)-2-[2-(3-butoksifenil)-etilamino]-N-metilpropanamidom (R)-2-[2-(3-butoksifenil)-etilamino]-N,N-dimetilpropanamidom 2-[2-(3-butoksi-2-trifluorometilfenil)-etilamino]-N,N-dimetilacetamidom 2-[2-(3-butoksi-4-trifluorometilfenil)-etilamino]-N,N-dimetilacetamidom 2-[2-(3-butoksi-5-trifluorometilfenil)-etilamino]-N,N-dimetilacetamidom v takšnem primeru bodisi kot posamičen optični izomer v izolirani obliki ali zmes le-teh v kakršnem koli razmerju in njene farmacevtsko sprejemljive soli, prednostno njene soli z klorovodikovo ali metansulfonsko kislino.
  6. 6. Spojina po zahtevku 1, ki je 2-[2-(3-butoksifenil)-etilamino]-N,N-dimetilacetamid, 2-[2-(3-butoksi-2,6-difluorofenil)-etilamino]-N,N-dimetilacetamid, 2-[2-(3-pentiloksifenil)-etilaminoj-N.N-dimetilacetamid ali 2-[2-(3-heksiloksifenil)-etilamino]-N,N-dimetilacetamid in farmacevtsko sprejemljive soli le-teh.
  7. 7. Spojina po zahtevku 6, ki je 2-[2-(3-butoksifenil)-etilamino]-N,N-dimetilacetamid ali njegova farmacevtsko sprejemljiva sol.
  8. 8. Spojina po katerem koli od zahtevkov 6 in 7, pri čemer je farmacevtsko sprejemljiva sol klorovodikova ali metansulfonatna sol.
  9. 9. Spojina po zahtevku 1, v kateri: X je -S02-; ali Υ je OH ali 0(CrC4)alkil; ali Z je =S; ali Rje (Cg-Cio)alkil ali u)-trifluoro(C3-Cio)alkil; ali Ri in/ali R2 se razlikujeta od vodika; ali R3 in R'3 se oba razlikujeta od vodika; ali R4 in R5 se oba razlikujeta od vodika, vendar ne tvorita (C3-C6)cikloalkilega ostanka, če sta vzeta skupaj s sosednjim atomom ogljika; ali R6 in R7 vzeta skupaj s sosednjim atomom dušika tvorita 5-6-členski nasičen heterocikel, ki po izbiri vsebuje en dodaten heteroatom, izbran med -O-, -S- in -NR8-, kjer je R8 vodik ali (Ci-C6) alkil; pod pogojem, da, kadar je X -S- ali -SO2-, potem Y ni OH ali 0(Ci-C4)alkil; v takšnem primeru bodisi kot posamičen optični izomer v izolirani obliki ali zmes le-teh v kakršnem koli razmerju in njene farmacevtsko sprejemljive soli.
  10. 10. Spojina po katerem koli od zahtevkov od 1 do 9 za uporabo kot zdravilo.
  11. 11. Spojina po zahtevku 1 za uporabo kot zdravilo, ki je aktivno kot modulator natrijevega in/ali kalcijevega kanala za zdravljenje patologij, kjer zgoraj navedeni mehanizem(-mi) igra(-jo) patološko vlogo, ki je nevrološka, kognitivna psihiatrična, vnetna, urogenitalna ali gastrointestinalna motnja, pri čemer je zdravilo v bistvu brez kakršne koli MAO inhibitorne aktivnosti ali ima bistveno zmanjšano MAO inhibitorno aktivnost.
  12. 12. Spojina po katerem koli od zahtevkov 2, 3 in 4 za uporabo po zahtevku 11.
  13. 13. Spojina po zahtevku 5 za uporabo po zahtevku 11.
  14. 14. Spojina po zahtevku 6 za uporabo po zahtevku 11.
  15. 15. Spojina po zahtevku 7 za uporabo po zahtevku 11.
  16. 16. Spojina po katerem koli od zahtevkov od 1 do 9 za uporabo po zahtevku 11, pri čemer je motnja nevrološka motnja, izbrana med bolečino in migreno.
  17. 17. Spojina po katerem koli od zahtevkov od 1 do 9 za uporabo po zahtevku 16, pri čemer je bolečina sindrom nevropatske bolečine ali sindrom vnetne bolečine.
  18. 18. Spojina po katerem koli od zahtevkov od 1 do 9 za uporabo po zahtevku 16, pri čemer je bolečina akutna ali kronična bolečina.
  19. 19. Spojina po katerem koli od zahtevkov od 1 do 9 za uporabo po zahtevku 11, pri čemer je motnja nevrološka motnja, izbrana med Alzheimerjevo boleznijo, Parkinsonovo boleznijo, epilepsijo, sindromom nemirnih nog, kapjo ali cerebralno ishemijo.
  20. 20. Spojina po katerem koli od zahtevkov od 1 do 9 za uporabo po zahtevku 11, pri čemer je motnja vnetni proces, ki vpliva na vse telesne sisteme in je izbrana med artritičnim stanjem, motnjo, ki vpliva na kožo in sorodna tkiva, motnja dihalnega sistema ali motnja imunskega in endokrinega sistema.
  21. 21. Spojina po katerem koli od zahtevkov od 1 do 9 za uporabo po zahtevku 11, pri čemer je motnja kognitivna in/ali psihiatrična motnja, izbrana med blago kognitivno motnjo, depresijo, bipolarno motnjo, manijo, shizofrenijo, psihozo, anksioznostjo in odvisnostjo.
  22. 22. Spojina po katerem koli od zahtevkov od 1 do 9 za uporabo po zahtevku 11, pri čemer je motnja urogenitalna motnja.
  23. 23. Spojina po katerem koli od zahtevkov od 1 do 9 za uporabo po zahtevku 11, pri čemer je motnja gastrointestinalna motnja.
  24. 24. Spojina po katerem koli od zahtevkov od 1 do 9 za uporabo po katerem koli od zahtevkov 11 in od 16 do 23, pri čemer je spojina v povezavi z enim ali več drugimi terapevtskimi sredstvi.
  25. 25. Farmacevtski sestavek, ki vsebuje kot učinkovino spojino po katerem koli od zahtevkov od 1 do 9 skupaj s farmacevtsko sprejemljivimi terapevtsko inertnimi organskimi ali anorganskimi nosilnimi materiali.
  26. 26. Spojina po katerem koli od zahtevkov od 1 do 9 za uporabo po zahtevku 21, pri čemer je spojina v povezavi z enim ali več terapevtskimi sredstvi po zahtevku 24, pri čemer je drugo terapevtsko sredstvo tipično ali atipično antipsihotično sredstvo.
  27. 27. Spojina po zahtevku 26, pri čemer je tipično antipsihotično sredstvo haloperidol in atipično antipsihotično sredstvo je izbrano med risperidonom in klozapinom.
  28. 28. Spojina po zahtevku 26, pri čemer je spojina 2-[2-(3-butoksifenil)-etilamino]-N,N-dimetilacetamid ali njegova farmacevtsko sprejemljiva sol, tipično antipsihotično sredstvo je haloperidol in atipično antipsihotično sredstvo je izbrano med risperidonom in klozapinom.
  29. 29. Spojina po zahtevku 26, pri čemer je spojina hidroklorid ali metansulfonat 2-(2-(3-butoksifenil)-etilamino]-N,N-dimetilacetamida in tipično antipsihotično sredstvo je haloperidol in atipično antipsihotično sredstvo je izbrano med risperidonom in klozapinom.
  30. 30. Spojina po katerem koli od zahtevkov od 1 do 9 za uporabo po zahtevku 20, pri čemer je motnja motnja imunskega sistema.
  31. 31. Spojina po zahtevku 30, pri čemer je motnja imunskega sistema multipla skleroza ali druge demielinizacijske motnje.
  32. 32. Spojina po katerem koli od zahtevkov od 1 do 9 za uporabo po katerem koli od zahtevkov od 11 do 24 in od 26 do 31, kjer so pacienti, ki trpijo za motnjo/motnjami, zlasti dovzetni za neželene stranske učinke zaradi MAO inhibitorne aktivnosti.
  33. 33. Uporaba spojine po katerem koli od zahtevkov od 1 do 9 za proizvodnjo zdravila, ki je aktivno kot modulator natrijevega in/ali kalcijevega kanala, za zdravljenje patologij, kjer zgoraj navedeni mehanizem(-mi) igra(-jo) patološko vlogo, ki je nevrološka, kognitivna psihiatrična, vnetna, urogenitalna ali gastrointestinalna motnja, pri čemer je zdravilo v bistvu brez kakršne koli MAO inhibitorne aktivnosti ali ima bistveno zmanjšano MAO inhibitorno aktivnost.
  34. 34. Uporaba po zahtevku 33, pri čemer je motnja takšna, kot navedeno v katerem koli od zahtevkov od 16 do 23.
SI200831914T 2007-06-15 2008-05-14 Substituirani 2-(2-(fenil)etilamino)alkanamidni derivati in njihova uporaba kot modulatorji natrijevega in/ali kalcijevega kanala SI2155663T1 (sl)

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DK2155663T3 (en) 2018-01-22
NO2155663T3 (sl) 2018-04-28
HRP20180324T1 (hr) 2018-04-06
US20150157602A1 (en) 2015-06-11
TW200908956A (en) 2009-03-01
CN101687773B (zh) 2014-07-30
US9474738B2 (en) 2016-10-25
JP2010529969A (ja) 2010-09-02
KR20100039848A (ko) 2010-04-16
CA2689561A1 (en) 2008-12-18
US20150157598A1 (en) 2015-06-11
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US20130289122A1 (en) 2013-10-31
BRPI0813363B8 (pt) 2021-05-25
NZ581288A (en) 2011-08-26
US8519000B2 (en) 2013-08-27
BRPI0813363B1 (pt) 2019-11-12
CA2689561C (en) 2015-11-17
EP2155663B1 (en) 2017-11-29
US9051240B2 (en) 2015-06-09
AU2008261325A1 (en) 2008-12-18
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US20150157600A1 (en) 2015-06-11
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