DK2155663T3 - Substituerede 2-[2-(phenyl)ethylamino]alkanamidderivater og deres anvendelse som natrium- og/eller kalciumkanalmodulatorer - Google Patents

Substituerede 2-[2-(phenyl)ethylamino]alkanamidderivater og deres anvendelse som natrium- og/eller kalciumkanalmodulatorer Download PDF

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DK2155663T3
DK2155663T3 DK08749449.8T DK08749449T DK2155663T3 DK 2155663 T3 DK2155663 T3 DK 2155663T3 DK 08749449 T DK08749449 T DK 08749449T DK 2155663 T3 DK2155663 T3 DK 2155663T3
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ethylamino
alkyl
butoxyphenyl
dimethylacetamide
disease
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DK08749449.8T
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Piero Melloni
Alessandra Restivo
Emanuela Izzo
Simona Francisconi
Elena Colombo
Cibele Sabido-David
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Newron Pharm Spa
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Claims (34)

1. Forbindelse med den almene formel (I):
hvor: X er -O-, -S- eller -S02-; Y er hydrogen, OH eller 0(Ci-C4)alkyl; Z er =0 eller =S; R er (C3-Cio)alkyl; (jo-trifluor(C3-C-i0)alkyl; Ri og R2 uafhængigt er hydrogen, hydroxy, (CrC8)alkoxy, (CrC8) alkylthio, halogen, trifluormethyl eller 2,2,2-trifluorethyl; eller et af Ri og R2 er i ortho- position til R-X- og i forening med samme R-X- repræsenterer en o— gruppe, hvor R0 er (C2-C9)alkyl; R3 og R'3 uafhængigt er hydrogen eller (CrC4)alkyl; R4 og R5 uafhængigt er hydrogen, (CrC4)alkyl; eller R4 er hydrogen, og R5 er en gruppe valgt blandt -CH2-OH, -CH2-0-(CrC6)alkyl, - CH(CH3)-OH, -(CH2)2-S-CH3, benzyl og 4-hydroxybenzyl; eller R4 og R5 i forening med det hosliggende carbonatom danner en (C3-C6)cycloalkylrest; R6 og R7 uafhængigt er hydrogen eller (CrC6)alkyl; eller i forening med det hosliggende nitrogenatom danner en 5-6-leddet monocyklisk mættet hetero-cyklus, som eventuelt indeholder et yderligere heteroatom valgt blandt -O-, -S- og -NRS- hvor R8 er hydrogen eller (CrC6) alkyl; forudsat at når X er -S- eller -S02-, så er Y ikke OH eller 0(CrC4) alkyl; i det pågældende tilfælde enten som en enkelt optisk isomer i den isolerede form eller blanding deraf i et hvilket som helst forhold og dens farmaceutisk acceptable salte.
2. Forbindelse ifølge krav 1, hvor: X er -O-, -S-; Y er hydrogen, OH eller 0(CrC3)alkyl; Z er =0 eller =S; R er (C4-C7)alkyl eller u>trifluor(C4-C6)alkyl; Ri og R2 uafhængigt er hydrogen, (CrC4)alkoxy, halogen, trifluormethyl eller 2,2,2-trifluorethyl; eller et af Ri og R2 er i ortho-position til R-X- og i forening med
samme R-X- repræsenterer en gruppe, hvor R0 er (C2-C5)alkyl; R3 og R'3 uafhængigt er hydrogen eller (CrC3)alkyl; R4 og R5 uafhængigt er hydrogen eller (CrC4)alkyl; eller R4 er hydrogen, og R5 er en gruppe valgt blandt -CH2-OH, -CH2-0-(CrC3)alkyl, - (CH2)2-S-CH3, benzyl og 4-hydroxybenzyl; R6 og R7 uafhængigt er hydrogen eller (CrC4)alkyl; eller i forening med det hosliggende nitrogenatom danner en 5-6-leddet monocyklisk mættet hetero-cyklus, som eventuelt indeholder et yderligere heteroatom valgt blandt -O- og -NRS-, hvor Rs er hydrogen eller (CrC3) alkyl; forudsat at når X er -S-, så er Y ikke OH eller 0(CrC3) alkyl; i det pågældende tilfælde enten som en enkelt optisk isomer i den isolerede form eller blanding deraf i et hvilket som helst forhold og dens farmaceutisk acceptable salte.
3. Forbindelse ifølge krav 1, hvor: X er -O-, -S-; Y er hydrogen eller 0(CrC3)alkyl; Z er =0 eller =S; R er (C4-C7)alkyl eller u>trifluor(C4-C6)alkyl; Ri og R2 uafhængigt er hydrogen, (CrC3)alkoxy, fluor, chlor, trifluormethyl eller 2,2,2-trifluorethyl; eller et af Ri og R2 er i ortho-position til R-X- og i for-enina med samme R-X- repræsenterer en
gruppe, hvor R0 er (C3-C4)alkyl; R3 og R'3 uafhængigt er hydrogen eller (CrC3)alkyl; R4 og R5 uafhængigt er hydrogen eller (CrC4)alkyl; eller R4 er hydrogen, og R5 er en gruppe valgt blandt -CH2-OH, -CH2-0-(CrC3)alkyl, benzyl og 4-hydroxybenzyl; R6 og R7 uafhængigt er hydrogen eller (CrC3)alkyl; eller i forening med det hosliggende nitrogenatom danner en 5-6-leddet monocyklisk mættet heterocyklus, som eventuelt indeholder et yderligere heteroatom valgt blandt -O- og -NR8-, hvor R8 er hydrogen eller (C1-C3) alkyl; forudsat at når X er -S-, så er Y ikke 0(C-|-C3) alkyl; i det pågældende tilfælde enten som enkelt optisk isomer i den isolerede form eller blanding deraf i et hvilket som helst forhold og dens farmaceutisk acceptable salte.
4. Forbindelse ifølge krav 1, hvor: X er -0-; Y er hydrogen; Z er =0; R er (C4-C6)alkyl; Ri og R2 uafhængigt er hydrogen eller halogen, fortrinsvis fluor; R3, R'3, R4 og R5 er hydrogen; R6 og R7 uafhængigt er hydrogen eller (CrC3)alkyl; i det pågældende tilfælde enten som en enkelt optisk isomer i den isolerede form eller blanding deraf i et hvilket som helst forhold og dens farmaceutisk acceptable salte.
5. Forbindelse ifølge krav 1, som er valgt blandt: 2-[2-(3-butoxyphenyl)-ethylamino]-acetamid 2-[2-(3-pentyloxyphenyl)-ethylamino]-acetamid 2-[2-(3-hexyloxyphenyl)-ethylamino]-acetamid 2-[2-(3-butoxyphenyl)-ethylamino]-N-methylacetamid 2-[2-(3-pentyloxyphenyl)-ethylamino]-N-methylacetamid 2-[2-(3-hexyloxyphenyl)-ethylamino]-N-methylacetamid 2-[2-(3-butoxyphenyl)-ethylamino]-N,N-dimethylacetamid 2-[2-(3-butylsulfonylphenyl)-ethylamino]-N,N-dimethylacetamid 2-[2-(3-butoxyphenyl)-(N'-hydroxy)ethylamino]-N,N-dimethylacetamid 2-[2-(3-butoxyphenyl)- (N'-methoxy)ethylamino]-N,N-dimethylacetamid 2-[2-(3-butoxyphenyl)- (N'-propoxy)ethylamino]-N,N-dimethylacetamid 2-[2-(3-butoxyphenyl)-ethylamino]-N,N-dimethyl-thioacetamid 2-[2-(3-butoxyphenyl)-2-methylpropylamino]-N,N-dimethylacetamid 2-{2-[3-(4,4,4-trifluorbutoxy)phenyl]-ethylamino}-N,N-dimethylacetamid 2-[2-(3-butylthiophenyl)-ethylamino]-N,N-dimethylacetamid 2-[2-(3-butoxy-2-chlorophenyl)-ethylamino]-N,N-dimethylacetamid 2-[2-(3-butoxy-2-fluorphenyl)-ethylamino]-N,N-dimethylacetamid 2-[2-(3-butoxy-4-methoxyphenyl)-ethylamino]-N,N-dimethylacetamid 2-[2-(3-butoxyphenyl)-ethylamino]-N,N-diethylacetamid 2-[2-(3-butoxyphenyl)-ethylamino]-N,N-dipropylacetamid 2-[2-(3-butoxyphenyl)-ethylamino]-N,N-dibutylacetamid 2-[2-(3-pentyloxyphenyl)-ethylamino]-N,N-dimethylacetamid 2-[2-(3-hexyloxyphenyl)-ethylamino]-N,N-dimethylacetamid 2-[2-(3-butoxyphenyl)-ethylamino]-1 -pyrrolidin-1 -yl-ethan-1 -on 2-[2-(3-pentyloxyphenyl)-ethylamino]-1 -pyrrolidin-1 -yl-ethan-1 -on 2-[2-(3-hexyloxyphenyl)-ethylamino]-1 -pyrrolidin-1 -yl-ethan-1 -on 2-[2-(3-butoxyphenyl)-ethylamino]- N,N-dimethylpropanamid 2-[2-(3-butoxyphenyl)-ethylamino]-3-hydroxy-N,N-dimethylpropanamid 2-[2-(3-butoxyphenyl)-ethylamino]-3-methoxy-N,N-dimethylpropanamid 2-[2-(3-butoxyphenyl)-ethylamino]-3-propoxy-N,N-dimethylpropanamid 2-[2-(3-butoxyphenyl)-ethylamino]-2,N,N-trimethylpropanamid 2-[2-(3-pentyloxyphenyl)-ethylamino]-2,N,N-trimethylpropanamid 2-[2-(3-hexyloxyphenyl)-ethylamino]-2,N,N-trimethylpropanamid (S)-2-[2-(3-butoxyphenyl)-ethylamino]-propanamid (S)-2-[2-(3-butoxyphenyl)-ethylamino]-N-methylpropanamid (S)-2-[2-(3-butoxyphenyl)-ethylamino]-N,N-dimethylpropanamid (R)-2-[2-(3-butoxyphenyl)-ethylamino]-propanamid (R)-2-[2-(3-butoxyphenyl)-ethylamino]-N-methylpropanamid (R)-2-[2-(3-butoxyphenyl)-ethylamino]-N,N-dimethylpropanamid 2-[2-(3-butoxy-2-trifluormethylphenyl)-ethylamino]-N,N-dimethylacetamid 2-[2-(3-butoxy-4-trifluormethylphenyl)-ethylamino]-N,N-dimethylacetamid 2-[2-(3-butoxy-5-trifluormethylphenyl)-ethylamino]-N,N-dimethylacetamid i det pågældende tilfælde enten som en enkelt optisk isomer i den isolerede form eller blanding deraf i et hvilket som helst forhold og dens farmaceutisk acceptable salte, fortrinsvis dens salt med salt- eller methansulfonsyre.
6. Forbindelse ifølge krav 1, som er 2-[2-(3-butoxyphenyl)-ethylamino]-N,N-dimethylacetamid, 2-[2-(3-butoxy-2,6-difluorphenyl)-ethylamino]-N,N- dimethylacetamid, 2-[2-(3-pentyloxyphenyl)-ethylamino]-N,N- dimethylacetamid eller 2-[2-(3-hexyloxyphenyl)-ethylamino]-N,N- dimethylacetamid og de farmaceutisk acceptable salte deraf.
7. Forbindelse ifølge krav 6, som er 2-[2-(3-butoxyphenyl)-ethylamino]-N,N-dimethylacetamid eller et farmaceutisk acceptabelt salt deraf.
8. Forbindelse ifølge et af kravene 6 og 7, hvor det farmaceutisk acceptable salt er hydrochlorid- eller methansulfonatsaltet.
9. Forbindelse ifølge krav 1, hvor: X er -S02-; eller Y er OH eller 0(CrC4)alkyl; eller Z er =S; eller R er (C9-Cio)alkyl eller u-thfluor(C3-Ci0)alkyl; eller Ri og/eller R2 er forskellige fra hydrogen; eller både R3 og R'3 er forskellige fra hydrogen; eller både R4 og R5 er forskellige fra hydrogen, men ikke danner en (C3-C6)cycloalkylrest, når de er i forening med det hosliggende carbonatom; eller R6 og R7 i forening med det hosliggende nitrogenatom danner en monocyklisk 5-6-leddet mættet heterocyklus, som eventuelt indeholder et yderligere heteroatom valgt blandt -O-, -S- og -NR8-, hvor R8 er hydrogen eller (CrC6) al kyl; forudsat at når X er -S- eller -S02-, så er Y ikke OH eller 0(CrC4)alkyl; i det pågældende tilfælde enten som enkelt optisk isomer i den isolerede form eller blanding deraf i et hvilket som helst forhold og dens farmaceutisk acceptable salte.
10. Forbindelse ifølge et af kravene 1 til 9 til anvendelse som medikament.
11. Forbindelse ifølge krav 1 til anvendelse som et medikament, der er aktivt som natrium- og/eller kalciumkanalmodulator til behandling af patologier, hvor den ovennævnte mekanisme(r) spiller en patologisk rolle, som er en neurologisk, kognitiv, psykiatrisk, inflammatorisk, urogenital eller gastrointestinal sygdom, hvor medikamentet er i det væsentlige frit for MAO-inhibitorisk aktivitet eller har en signifikant reduceret MAO-inhibitorisk aktivitet.
12. Forbindelse ifølge et af kravene 2,3 og 4 til anvendelse ifølge krav 11.
13. Forbindelse ifølge krav 5 til anvendelse ifølge krav 11.
14. Forbindelse ifølge krav 6 til anvendelse ifølge krav 11.
15. Forbindelse ifølge krav 7 til anvendelse ifølge krav 11.
16. Forbindelse ifølge et af kravene 1 til 9 til anvendelse ifølge krav 11, hvor sygdommen er en neurologisk sygdom valgt blandt smerte og migræne.
17. Forbindelse ifølge et af kravene 1 til 9 til anvendelse ifølge krav 16, hvor smerten er et neuropatisk smertesyndrom eller et inflammatorisk smertesyndrom.
18. Forbindelse ifølge et af kravene 1 til 9 til anvendelse ifølge krav 16, hvor smerten er en akut eller kronisk smerte.
19. Forbindelse ifølge et af kravene 1 til 9 til anvendelse ifølge krav 11, hvor sygdommen er en neurologisk sygdom valgt blandt Alzheimers sygdom, Parkinsons sygdom, epilepsi, restless legs-syndrom, slagtilfælde eller cerebral iskæmi.
20. Forbindelse ifølge et af kravene 1 til 9 til anvendelse ifølge krav 11, hvor sygdommen er en inflammatorisk proces, som påvirker alle kropssystemer valgt blandt en artritisk tilstand, en sygdom, som påvirker hud og relateret væv, en sygdom i åndedrætssystemet eller en sygdom i immunsystemet eller det endokrinologiske system.
21. Forbindelse ifølge et af kravene 1 til 9 til anvendelse ifølge krav 11, hvor sygdommen er en kognitiv og/eller psykiatrisk sygdom valgt blandt let kognitiv svækkelse, depression, bipolar lidelse, mani, skizofreni, psykose, angst og afhængighed.
22. Forbindelse ifølge et af kravene 1 til 9 til anvendelse ifølge krav 11, hvor sygdommen er en urogenital sygdom.
23. Forbindelse ifølge et af kravene 1 til 9 til anvendelse ifølge krav 11, hvor sygdommen er en gastrointestinal sygdom.
24. Forbindelse ifølge et af kravene 1 til 9 til anvendelse ifølge et af kravene 11 og 16 til 23, hvor forbindelsen er associeret med et eller flere andre terapeutiske midler.
25. Farmaceutisk sammensætning, der som aktivstof indeholder en forbindelse ifølge et af kravene 1 til 9 i forening med farmaceutisk acceptable terapeutisk inerte organiske eller uorganiske bærermaterialer.
26. Forbindelse ifølge et af kravene 1 til 9 til anvendelse ifølge krav 21, hvor forbindelsen er associeret med et eller flere andre terapeutiske midler ifølge krav 24, hvor det andet terapeutiske middel er et typisk eller et atypisk anti-psykotisk middel.
27. Forbindelse ifølge krav 26, hvor det typiske antipsykotiske middel er haloperidol, og det atypiske antipsykotiske middel er valgt blandt risperidon og clozapin.
28. Forbindelse ifølge krav 26, hvor forbindelsen er 2-[2-(3-butoxyphenyl)-ethylamino]-N,N-dimethylacetamid eller et farmaceutisk acceptabelt salt deraf, hvor det typiske antipsykotiske middel er haloperidol, og det atypiske antipsykotiske middel er valgt blandt risperidon og clozapin.
29. Forbindelse ifølge krav 26, hvor forbindelsen er hydrochloridet eller methansulfonatet af 2-[2-(3-butoxyphenyl)-ethylamino]-N,N- dimethylacetamid, og det typiske antipsykotiske middel er haloperidol, og det atypiske antipsykotiske middel er valgt blandt risperidon og clozapin.
30. Forbindelse ifølge et af kravene 1 til 9 til anvendelse ifølge krav 20, hvor sygdommen er en sygdom i immunsystemet.
31. Forbindelse ifølge krav 30, hvor sygdommen i immunsystemet er multipel sklerose eller andre demyeliniseringssygdomme.
32. Forbindelse ifølge et af kravene 1 til 9 til anvendelse ifølge et af kravene 11 til 24 og 26 til 31, hvor patienterne, som lider af sygdommen(e), især er følsomme over for uønskede bivirkninger på grund af MAO-inhibitorisk aktivitet.
33. Anvendelse af en forbindelse ifølge et af kravene 1 til 9 til fremstilling af et medikament, der er aktivt som natrium- og/eller kalciumkanalmodulator til behandling af patologier, hvor den ovennævnte mekanisme(r) spiller en patologisk rolle, som er en neurologisk, kognitiv, psykiatrisk, inflammatorisk, urogenital eller gastrointestinal sygdom, hvor medikamentet er i det væsentlige frit for MAO-inhibitorisk aktivitet eller har en signifikant reduceret MAO-inhibitorisk aktivitet.
34. Anvendelse ifølge krav 33, hvor sygdommen er ifølge et af kravene 16 til 23.
DK08749449.8T 2007-06-15 2008-05-14 Substituerede 2-[2-(phenyl)ethylamino]alkanamidderivater og deres anvendelse som natrium- og/eller kalciumkanalmodulatorer DK2155663T3 (da)

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US9474738B2 (en) 2016-10-25
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