DK2855426T3 - Forbindelser, som hæmmer aktiviteten af catechol-o-methyltransferase - Google Patents

Forbindelser, som hæmmer aktiviteten af catechol-o-methyltransferase Download PDF

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DK2855426T3
DK2855426T3 DK13730284.0T DK13730284T DK2855426T3 DK 2855426 T3 DK2855426 T3 DK 2855426T3 DK 13730284 T DK13730284 T DK 13730284T DK 2855426 T3 DK2855426 T3 DK 2855426T3
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dihydroxy
alkyl
isophthalonitrile
dihydroxyisophthalonitrile
aryl
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DK13730284.0T
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English (en)
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Marko Ahlmark
Belle David Din
Mika Kauppala
Anne Luiro
Taina Pajunen
Jarmo Pystynen
Eija Tiainen
Matti Vaismaa
Josef Messinger
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Orion Corp
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Claims (48)

1. Forbindelse med formlen I,
I hvor Ri er (Ci-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C7)cycloalkyl, (C4-Cio)cycloalkenyl, aryl, (R2)2C=C-, halogen, hydroxy, (Ci-C6)alkoxy, (Ci-C6)alkyl-S-, (C4-Cio)cycloalkenyloxy, (C4-Cio)cycloalkenyl-S-, aryloxy, aryl-S-, heteroaryloxy, heteroaryl-S-, (R3)2N-, (R4)2C=N-, heterocyclyl, heteroaryl, aryl(Ci-C6)alkyl, (1 -amino-1 -carboxymethyl)-(Ci-C6)alkyl, halogen(Ci-C6)alkyl, hydroxy(Ci-C6)alkyl, (Ci-C6)alkoxy(Ci-C6)alkyl, (Ci-Ce)alkyl-S-(Ci-C6)alkyl, (R3)2N-(Ci-C6)alkyl, heterocyclyl(Ci-C6)alkyl, carboxy(C2-Ce)a I kenyl, (C3-C7)cycloal kyl (C2-Ce)a I kenyl, ary I (C2-C6)a I kenyl, (Ci -C6)a I koxy(C2-C6)al kenyl, heterocyclyl(C2-C6)alkenyl, heteroaryl(C2-C6)alkenyl, carboxy(C2-C6)a I kynyl, (C3-C7)cycloa I kyl (C2-C6)al ky nyl, ary I (C2-C6)a I kynyl, (Ci -C6)a I koxy(C2-C6)al kynyl, heterocyclyl (C2-C6)al kynyl, heteroaryl (C2-Ce)a I kynyl, halogen(Ci-C6)alkoxy, hydroxy(Ci-C6)alkoxy, (Ci-C6)alkoxy(Ci-C6)alkoxy, (Ci-C6)alkyl-(C=0)-0-, R5-(S=0)-, R5-(0=S=0)-, hyd roxy(Ci -C6)al koxy(Ci -C6)a I ky I, (Ci-C6)alkoxy-(C=0)-(C2-C6)alkenyl eller (Ci-C6)alkyl-(C=0)-0-(Ci-C6)alkyl, hvor (C4-Cio)cycloalkenyl-, aryl-, heterocyclyl-, heteroaryl- eller (C3-C7)cycloalkylgruppen som sådan eller som del af en anden gruppe er usubstitueret eller substitueret med 1, 2 eller 3 substituent(er) Re; R2 uafhængigt for hver forekomst er carboxy eller aryl, hvor arylgruppen uafhængigt for hver forekomst er usubstitueret eller substitueret med 1,2 eller 3 substituent(er) Re; R3 uafhængigt for hver forekomst er H, (Ci-Ce)alkyl, (C3-C7)cycloalkyl, aryl, (C3-C7)cycloalkyl(Ci-Ce)alkyl, hydroxy(Ci-Ce)alkyl eller (Ci-C6)alkoxy(Ci-C6)alkyl, hvor (C3-C7)cycloalkyl- eller arylgruppen som sådan eller som del af en anden gruppe uafhængigt for hver forekomst er usubstitueret eller substitueret med 1 substituent, som er (Ci-C6)alkyl, halogen, hydroxy, (Ci-Ce)alkoxy eller hydroxy(Ci-C6)alkyl; R4 uafhængigt for hver forekomst er H eller aryl, hvor arylgruppen uafhængigt for hver forekomst er usubstitueret eller substitueret med 1 substituent, som er (Ci-C6)alkyl, halogen eller (Ci-C6)alkoxy; R5 er (Ci-C6)alkyl, aryl, hydroxy eller (Ci-Ce)alkoxy, hvor arylgruppen er usubstitueret eller substitueret med 1,2 eller 3 substituent(er) R6; Re uafhængigt for hver forekomst er (Ci-Ce)alkyl, (C2-C6)alkenyl, carboxy, cyano, aryl, halogen, hydroxy, (Ci-Ce)alkoxy, (Ci-C6)alkyl-S-, (C4-Cio)cycloalkenyloxy, (C4-Cio)cycloalkenyl-S-, aryloxy, aryl-S-, heteroaryloxy, heteroaryl-S-, (R7)2N-, heteroaryl, carboxy(Ci-C6)alkyl, aryl(Ci-C6)alkyl, halogen(Ci-C6)alkyl, hydroxy(Ci-Ce)alkyl, (C1 -C6)alkoxy(Ci-Cejalkyl, heterocyclyl(Ci-Cejalkyl, (C1 -C6)alkyl-(C=0)-, (Ci-C6)alkoxy-(C=0)-, heterocyciyi-(C=0)-, (R7)2N-(C=0)-, halogen(Ci-C6)alkoxy, R8-(S=0)-, R8-(0=S=0)-, (C1 -C6)alkoxy-(C=0)-(Ci-C6)alkyl, (R7)2N-(C=0)-(Ci-C6)alkyl eller (Ci-C6)alkoxy(Ci-C6)alkoxy-(C=0)-, hvor aryl-, heteroaryl- eller heterocyclylgruppen som sådan eller som del afen anden gruppe uafhængigt for hver forekomst er usubstitueret eller substitueret med 1 substituent, som er (CrC6)alkyl; eller R6 og R6 begge er bundet til det samme carbonringatom og sammen med det carbonringatom, hvortil de er bundet, udgør en -(C=0)-gruppe; R7 uafhængigt for hver forekomst er H, (Ci-C6)alkyl, (C3-C7)cycloalkyl eller carboxy(Ci-C6)alkyl, hvor (C3-C7)cycloalkylgruppen uafhængigt for hver forekomst er usubstitueret eller substitueret med 1 substituent, som er (Ci-Cejalkyl; Re uafhængigt for hver forekomst er (Ci-C6)alkyl, hydroxy, (Ci-Ce)alkoxy eller (R9)2N-; R9 uafhængigt for hver forekomst er (Ci-C6)alkyl; eller et farmaceutisk acceptabelt salt eller en farmaceutisk acceptabel ester deraf.
2. Forbindelse ifølge krav 1, hvor Ri er (Ci-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C4-Cio)cycloalkenyl, aryl, halogen, hydroxy, (C4-Cio)cycloalkenyloxy, aryloxy, aryl-S-, heteroaryl-S-, (R3)2N-, (R4)2C=N-, heterocyclyl, heteroaryl, aryl(Ci-C6)alkyl, hydroxy(Ci-C6)alkyl, (R3)2N-(Ci-Ce)alkyl, heterocyclyl(Ci-C6)alkyl, carboxy(C2-C6)alkenyl, (C3-C7)cycloalkyl(C2-C6)alkenyl, aryl(C2-C6)alkenyl, (Ci-C6)alkoxy(C2-C6)alkenyl, heteroaryl(C2-C6)alkenyl, aryl(C2-C6)alkynyl, (Ci-C6)alkoxy(C2-C6)alkynyl, R5-(S=0)-, R5-(0=S=0)- eller (Ci-C6)alkoxy-(C=0)-(C2-C6)alkenyl, hvor (C4-Cio)cycloalkenyl-, aryl-, heterocyclyl-, heteroaryl- eller (C3-C7)cycloalkylgruppen som sådan eller som del af en anden gruppe er usubstitueret eller substitueret med 1,2 eller 3 substituent(er) Re; R3 uafhængigt for hver forekomst er H, (Ci-Ce)alkyl, (C3-C7)cycloalkyl, aryl, (C3-C7)cycloalkyl(Ci-C6)alkyl, hydroxy(Ci-Ce)alkyl eller (Ci-C6)alkoxy(Ci-C6)alkyl, hvor (C3-C7)cycloalkyl- eller arylgruppen som sådan eller som del af en anden gruppe er usubstitueret eller substitueret med 1 substituent, som er (Ci-Ce)alkyl; R4 uafhængigt for hver forekomst er H eller aryl, hvor arylgruppen uafhængigt for hver forekomst er substitueret med 1 substituent, som er (Ci-C6)alkyl, halogen eller (Ci-C6)alkoxy; R5 er aryl, hvor arylgruppen er substitueret med 1 substituent R6; Re uafhængigt for hver forekomst er (Ci-C6)alkyl, (C2-C6)alkenyl, carboxy, cyano, aryl, halogen, hydroxy, (Ci-Ce)alkoxy, (Ci-Ce)alkyl-S-, aryloxy, heteroaryl, carboxy(Ci-Ce)alkyl, aryl(C1 -C6)alkyl, halogen(Ci-Ce)alkyl, hydroxy(Ci-Ce)alkyl, (Ci-Ce)alkoxy(Ci-C6)alkyl, heterocyclyl(Ci-C6)alkyl, (Ci-C6)alkyl-(C=0)-, (Ci-Ce)alkoxy-(C=0)-, heterocyclyl-(C=0)-, (R7)2N-(C=0)-, halogen(Ci-Ce)alkoxy, R8-(0=S=0)-, (Ci-Ce)alkoxy-(C=0)-(Ci-C6)alkyl, (R7)2N-(C=0)-(Ci-Ce)alkyl eller (Ci-C6)alkoxy(Ci-C6)alkoxy-(C=0)-, hvor aryl-, heteroaryl- eller heterocyclylgruppen som sådan eller som del af en anden gruppe uafhængigt for hver forekomst er usubstitueret eller substitueret med 1 substituent, som er (Ci-Ce)alkyl; eller R6 og R6 begge er bundet til det samme carbonringatom og sammen med det carbonringatom, hvortil de er bundet, udgøren -(C=0)-gruppe; R7 uafhængigt for hver forekomst er H, (Ci-C6)alkyl, (C3-C7)cycloalkyl eller carboxy(Ci-C6)alkyl, hvor (C3-C7)cycloalkylgruppen er usubstitueret; Re uafhængigt for hver forekomst er (Ci-Ce)alkyl eller (Rg^N-; Rg uafhængigt for hver forekomst er (Ci-Cejalkyl.
3. Forbindelse ifølge krav 2, hvor Ri er (Ci-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C4-Cio)cycloalkenyl, aryl, halogen, (C4-Cio)cycloalkenyloxy, aryloxy, aryl-S-, heteroaryl-S-, (Rs)2N-, (R4)2C=N-, heterocyclyl, heteroaryl, aryl(Ci-C6)alkyl, (R3)2N-(Ci-C6)alkyl, carboxy(C2-C6)alkenyl, (C3-C7)cycloalkyl(C2-C6)alkenyl eller aryl(C2-C6)alkenyl, hvor (C4-Cio)cycloalkenyl-, aryl-, heterocyclyl-, heteroaryl- eller (C3-C7)cycloalkylgruppen som sådan eller som del afen anden gruppe er usubstitueret eller substitueret med 1,2 eller 3 substituent(er) Re; R3 uafhængigt for hver forekomst er H, (Ci-Ce)alkyl eller (C1 -C6)al koxy(Ci -C6)al kyl; R4 uafhængigt for hver forekomst er H eller aryl, hvor arylgruppen uafhængigt for hver forekomst er substitueret med 1 substituent, som er (Ci-C6)alkyl, halogen eller (Ci-C6)alkoxy; Re uafhængigt for hver forekomst er (Ci-Ce)alkyl, cyano, aryl, halogen, hydroxy, (Ci-C6)alkoxy, (Ci-Ce)alkyl-S-, carboxy(Ci-C6)alkyl, aryl(Ci-Ce)alkyl, halogen(Ci-Ce)alkyl, hydroxy(Ci-C6)alkyl, (Ci-C6)alkoxy(Ci-Ce)alkyl, heterocyclyl-(C=0)-, (R7)2N-(C=0)-R8-(0=S=0)- eller (Ci-C6)alkoxy-(C=0)-(Ci-C6)alkyl, hvor aryl- eller heterocyclylgruppen som sådan eller som del af en anden gruppe er usubstitueret; R7 uafhængigt for hver forekomst er H, (Ci-Ce)alkyl eller (C3-C7)cycloalkyl, hvor (C3-C7)cycloalkylgruppen er usubstitueret; Re uafhængigt for hver forekomst er (Ci-Ce)alkyl eller (Rg^N-; Rg uafhængigt for hver forekomst er (Ci-C6)alkyl.
4. Forbindelse ifølge krav 3, hvor Ri er (Ci-C6)alkyl, (C2-C6)alkenyl, aryl, halogen, aryloxy, aryl-S-, (R3)2N-, (R4)2C=N-, heterocyclyl, heteroaryl, aryl(Ci-C6)alkyl, (C3-C7)cycloalkyl(C2-C6)alkenyl eller aryl(C2-C6)alkenyl, hvor aryl-, heterocyclyl-, heteroaryl- eller (C3-C7)cycloalkylgruppen som sådan eller som del afen anden gruppe er usubstitueret eller substitueret med 1,2 eller 3 substituent(er) Re; R3 uafhængigt for hver forekomst er H eller (Ci-Ce)alkyl; R4 uafhængigt for hver forekomst er H eller aryl, hvor arylgruppen uafhængigt for hver forekomst er substitueret med 1 substituent, som er (Ci-C6)alkyl, halogen eller (Ci-Ce)alkoxy; R6 uafhængigt for hver forekomst er (Ci-Ce)alkyl, cyano, aryl, halogen, hydroxy, (Ci-C6)alkoxy, (Ci-Ce)alkyl-S-, carboxy(Ci-C6)alkyl, halogen(Ci-C6)alkyl, hydroxy(Ci-C6)alkyl, (Ci-C6)alkoxy(Ci-C6)alkyl, heterocyclyl-(C=0)-, (R7)2N-(C=0)- eller R8-(0=S=0)-, hvor aryl- eller heterocyclylgruppen som sådan eller som del afen anden gruppe er usubstitueret; R7 uafhængigt for hver forekomst er H eller (Ci-Ce)alkyl; Re uafhængigt for hver forekomst er (Ci-C6)alkyl.
5. Forbindelse ifølge krav 4, hvor Ri er (Ci-C6)alkyl, (C2-C6)alkenyl, aryl, halogen, aryloxy, aryl-S-, (R3)2N-, heterocyclyl, heteroaryl, aryl(Ci-C6)alkyl eller aryl(C2-C6)alkenyl, hvoraryl-, heterocyclyl- eller heteroarylgruppen som sådan eller som del afen anden gruppe er usubstitueret eller substitueret med 1,2 eller 3 substituent(er) R6; R3 uafhængigt for hver forekomst er H eller (Ci-Ce)alkyl; R6 uafhængigt for hver forekomst er (Ci-C6)alkyl, halogen, hydroxy, (Ci-C6)alkoxy, carboxy(Ci-C6)alkyl, halogen(Ci-C6)alkyl eller (R7)2N-(C=0)-; R7 uafhængigt for hver forekomst er H eller (Ci-C6)alkyl.
6. Forbindelse ifølge krav 5, hvor Ri er (C2-C6)alkenyl, aryl, halogen, aryloxy, aryl-S-, (R3)2N-, heteroaryl, aryl(Ci-C6)alkyl eller aryl(C2-C6)alkenyl, hvor aryl- eller heteroarylgruppen som sådan eller som del afen anden gruppe er usubstitueret eller substitueret med 1 eller 2 substituent(er) R6; R3 uafhængigt for hver forekomst er H eller (CrC6)alkyl; R6 uafhængigt for hver forekomst er (Ci-Ce)alkyl, halogen, (Ci-Ce)alkoxy, carboxy(Ci-C6)alkyl eller halogen(Ci-C6)alkyl.
7. Forbindelse ifølge krav 6, hvor Ri er (C2-Ce)alkenyl, aryl, halogen, aryl-S-, heteroaryl eller aryl(Ci-Ce)alkyl, hvor aryl- eller heteroarylgruppen som sådan eller som del afen anden gruppe er usubstitueret eller substitueret med 1 eller 2 substituent(er) Re; R6 uafhængigt for hver forekomst er (Ci-Ce)alkyl, halogen eller (Ci-C6)alkoxy.
8. Forbindelse ifølge krav 7, hvor Ri er (C2-C6)alkenyl, halogen, aryl-S- eller aryl(Ci-Ce)alkyl, hvor arylgruppen som del af en anden gruppe er usubstitueret eller substitueret med 1 eller 2 substituent(er) R6; R6 uafhængigt for hver forekomst er (Ci-Ce)alkyl, halogen eller (Ci-C6)alkoxy.
9. Forbindelse ifølge krav 7, hvor Ri er (C2-C6)alkenyl, aryl, aryl-S-, heteroaryl eller aryl(CrC6)alkyl, hvor aryl-eller heteroarylgruppen som sådan eller som del afen anden gruppe er substitueret med 1 eller 2 substituent(er) R6; Re uafhængigt for hver forekomst er (Ci-Ce)alkyl eller (Ci-C6)alkoxy.
10. Forbindelse ifølge krav 9, hvor Ri er (C2-C6)alkenyl, aryl-S- eller aryl(Ci-C6)alkyl, hvor arylgruppen som del af en anden gruppe er substitueret med 1 eller 2 substituent(er) R6; R6 uafhængigt for hver forekomst er (Ci-Ce)alkyl eller (Ci-Ce)alkoxy.
11. Forbindelse ifølge krav 7, hvor Ri er (C2-C6)alkenyl.
12. Forbindelse ifølge krav 7, hvor Ri er aryl, hvor arylgruppen er usubstitueret eller substitueret med 1 eller 2 substituent(er) R6; Re uafhængigt for hver forekomst er (Ci-C6)alkyl, halogen eller (Ci-Ce)alkoxy.
13. Forbindelse ifølge krav 7, hvor Ri er aryl-S-, hvor arylgruppen er usubstitueret eller substitueret med 1 eller 2 substituent(er) Re; R6 uafhængigt for hver forekomst er (Ci-Ce)alkyl, halogen eller (Ci-Ce)alkoxy.
14. Forbindelse ifølge krav 7, hvor Ri er heteroaryl, hvor heteroarylgruppen er usubstitueret eller substitueret med 1 eller 2 substituent(er) Re; R6 uafhængigt for hver forekomst er (Ci-Ce)alkyl, halogen eller (Ci-Ce)alkoxy.
15. Forbindelse ifølge krav 7, hvor Ri er aryl(Ci-C6)alkyl, hvor arylgruppen er substitueret med 1 eller 2 substituent(er) Re; R6 uafhængigt for hver forekomst er (Ci-Ce)alkyl eller (Ci-Ce)alkoxy.
16. Forbindelse ifølge krav 1, hvor forbindelsen er 2-brom-4,5-dihydroxyisophthalonitril, 4.5- dihydroxy-2-(phenylethynyl)isophthalonitril, 4.5- dihydroxy-2-(prop-1-ynyl)isophthalonitril, 4.5- dihydroxy-2-(1 -methyl-1 H-pyrrol-2-yl)isophthalonitril, 4.5- dihydroxy-2-(thiophen-2-yl)isophthalonitril, 2-(furan-2-yl)-4,5-dihydroxyisophthalonitril, 3' ,4' ,5'-trif I uor-3,4-d i hyd roxy b ipheny I-2,6-d ica rbon itril, 4.5- dihydroxy-2-(naphthalen-1-yl)isophthalonitril, 4'-tert-butyl-3,4-dihydroxybiphenyl-2,6-dica rbon itril, 3.4- dihydroxy-4'-(hydroxymethyl)biphenyl-2,6-dica rbon itril, 4.5- dihydroxy-2-(naphthalen-2-yl)isophthalonitril, 3.4- dihydroxy-4'-(isopropylthio)biphenyl-2,6-dicarbonitril, 3.4- dihydroxy-4'-(methylthio)biphenyl-2,6-dica rbon itril, 3.4- dihydroxy-4'-isopropoxybiphenyl-2,6-dicarbonitril, 4'-(ethylthio)-3,4-dihydroxybiphenyl-2,6-dicarbonitril, 3.4- dihydroxy-4'-isopropoxy-3',5'-dimethylbiphenyl-2,6-dicarbonitril, 4'-butyl-3,4-dihydroxybiphenyl-2,6-dicarbonitril, 3.4- dihydroxy-2',4',5,-trimethylbiphenyl-2,6-dicarbonitril, 3.4- dihydroxy-2',5'-dimethylbiphenyl-2,6-dica rbon itril, 2- cyclohexenyl-4,5-dihydroxyisophthalonitril, 3'-ethyl-3,4-dihydroxybiphenyl-2,6-dicarbonitril, 3.4- dihydroxybiphenyl-2,4',6-tricarbonitril, 3.4- dihydroxy-4'-(isopropylsulfonyl)biphenyl-2,6-dicarbonitril, 2',6'-dicyano-3,,4,-dihydroxy-N,N-dimethylbiphenyl-4-sulfonamid, (E)-4,5-dihydroxy-2-(pent-1-enyl)isophthalonitril, 2',6'-dicyano-3',4,-dihydroxybiphenyl-3-carboxylsyre, 3.4- dihydrOxy-4'-(1-methoxyethyl)biphenyl-2,6-dicarbonitril, (E)-2-(3,3-dimethylbut-1-enyl)-4,5-dihydroxyisophthalonitril, 3.4- dihydrOxy-2'-methylbiphenyl-2,6-dicarbonitril, (E)-2-(2-cyclohexylvinyl)-4,5-dihydroxyisophthalonitril, (Z)-4,5-dihydroxy-2-(prop-1-enyl)isophthalonitril, 3- (2',6'-dicyano-3',4,-dihydroxybiphenyl-4-yl)propionsyre, 3.4- dihydroxy-3'-(hydroxymethyl)biphenyl-2,6-dica rbon itril, 3.4- dihydroxy-3'-(methoxymethyl)biphenyl-2,6-dicarbonitril, 2',6'-dicyano-3',4'-dihydroxy-N,N-dipropylbiphenyl-4-carboxannid, (E)-4,5-dihydroxy-2-(prop-1-enyl)isophthalonitril, 3.4- dihydroxybiphenyl-2,6-dicarbonitril, 3',4'-dichlor-3,4-dihydroxybiphenyl-2,6-dicarbonitril, 3.4- dihydroxy-3'-(trifluormethyl)biphenyl-2,6-dicarbonitril, 2-(furan-3-yl)-4,5-dihydroxyisophthalonitril, 3.4- dihydroxy-4'-(trifluormethyl)biphenyl-2,6-dicarbonitril, 4.5- dihydroxy-2-(thiophen-3-yl)isophthalonitril, 4.5- dihydroxy-2-(5-methylfuran-2-yl)isophthalonitril, 4.5- dihydroxy-2-(5-methylthiophen-2-yl)isophthalonitril, 2-benzyl-4,5-dihydroxyisophthalonitril, 2-(benzofuran-2-yl)-4,5-dihydroxyisophthalonitril, 2-(5-chlorthiophen-2-yl)-4,5-dihydroxyisophthalonitril, 2-(benzo[b]thiophen-2-yl)-4,5-dihydroxyisophthalonitril, (E)-4,5-dihydroxy-2-styrylisophthalonitril, 4'-ethyl-3,4-dihydroxybiphenyl-2,6-dicarbonitril, 3.4- dihydroxy-3',5'-dimethylbiphenyl-2,6-dicarbonitril, 4.5- dihydroxy-2-(phenylthio)isophthalonitril, 4.5- dihydroxy-2-(p-tolylthio)isophthalonitril, 4.5- dihydroxy-2-(4-methylbenzyl)isophthalonitril, 2-(4-fluorbenzyl)-4,5-dihydroxyisophthalonitril, 4.5- dihydroxy-2-(4-hydroxybenzyl)isophthalonitril, 4.5- dihydroxy-2-(2-methoxybenzyl)isophthalonitril, 4.5- dihydroxy-2-(4-(trifluormethoxy)benzyl)isophthalonitril, 2-(3-fluor-4-methoxybenzyl)-4,5-dihydroxyisophthalonitril, 2-(2-fluorbenzyl)-4,5-dihydroxyisophthalonitril, 4.5- dihydroxy-2-(2-methylbenzyl)isophthalonitril, 2-(2,5-dimethylbenzyl)-4,5-dihydroxyisophthalonitril, 2- (3-fluor-5-methylbenzyl)-4,5-dihydroxyisophthalonitril, 3- (2,6-dicyano-3,4-dihydroxybenzyl)benzoesyre, 2-(4-fluor-3-methylbenzyl)-4,5-dihydroxyisophthalonitril, 4.5- d ihyd roxy-2-(3-methylbenzyl )isophthalonitril, 2-(5-fluor-2-methoxybenzyl)-4,5-dihydroxyisophthalonitril, 2-(3,5-dimethylbenzyl)-4,5-dihydroxyisophthalonitril, 4.5- dihydroxy-2-(4-isopropylbenzyl)isophthalonitril, 2-(4-ethylbenzyl)-4,5-dihydroxyisophthalonitril, 4.5- dihydroxy-2-(naphthalen-1-ylmethyl)isophthalonitril, 5-(2,6-dicyano-3,4-dihydroxybenzyl)-2-hydroxybenzoesyre, 2-(2,4-dimethylbenzyl)-4,5-dihydroxyisophthalonitril, 2-(3,6-dihydro-2H-pyran-4-yl)-4,5-dihydroxyisophthalonitril, 2-cyclopentenyl-4,5-dihydroxyisophthalonitril, (E)-3-(2,6-dicyano-3,4-dihydroxyphenyl)acrylsyre, (E)-4,5-dihydroxy-2-(3-methoxyprop-1-enyl)isophthalonitril, 4.5- dihydroxy-2-(5-(morpholinomethyl)thiophen-2-yl)isophthalonitril, S^-dihydroxy^'^morpholin^-carbonylJbiphenyl^.ø-dicarbonitril, 2-(5'-hexyl-2,2'-bithiophen-5-yl)-4,5-dihydroxyisophthalonitril, 2-(1 -benzyl-1 H-pyrazol-4-yl)-4,5-dihydroxyisophthalonitril, 2-(5-hexylthiophen-2-yl)-4,5-dihydroxyisophthalonitril, (Z)-2-(but-2-enyl)-4,5-dihydroxyisophthalonitril, 4.5- dihydroxy-2-(3-methylbut-2-enyl)isophthalonitril, (E)-2-(but-2-enyl)-4,5-dihydroxyisophthalonitril, 4.5- dihydroxy-2-methylisophthalonitril, 4.5- dihydroxy-2-(2-methylprop-1-enyl)isophthalonitril, 3.4- dihydroxy-3'-methylbiphenyl-2,6-dicarbonitril, 4.5- dihydroxy-2-vinylisophthalonitril, 4.5- dihydroxy-2-(prop-1-en-2-yl)isophthalonitril, 2-(2-ethoxythiazol-5-yl)-4,5-dihydroxyisophthalonitril, 2-allyl-4,5-dihydroxyisophthalonitril, 3'-(tert-butoxymethyl)-3,4-dihydroxybiphenyl-2,6-dicarbonitril, tert-butyl-2',6'-dicyano-3',4'-dihydroxybiphenyl-3-carboxylat, 3,4-dihydroxybiphenyl-2,3',6-tricarbonitril, 2',6'-dicyano-3',4'-dihydroxy-N,N-dipropylbiphenyl-3-carboxamid, 2',6'-dicyano-N-cyclohexyl-3',4'-dihydroxybiphenyl-4-carboxamid, 2',6'-dicyano-N-cyclohexyl-3',4'-dihydroxybiphenyl-3-carboxamid, 2',6'-dicyano-N,N-diethyl-3',4'-dihydroxybiphenyl-4-carboxannid, 2',6'-dicyano-N,N-diethyl-3',4'-dihydroxybiphenyl-3-carboxarriid, 2',6'-dicyano-N-ethyl-3',4'-dihydroxybiphenyl-3-carboxamid, 2',6'-dicyano-3',4'-dihydroxy-N,N-dimethylbiphenyl-3-carboxannid, 4'-fluor-3,4-dihydroxybiphenyl-2,6-dicarbonitril, 3',4'-difluor-3,4-dihydroxybiphenyl-2,6-dicarbonitril, 4'-fluor-3,3',4-trihydroxybiphenyl-2,6-dicarbonitril, (E)-4,5-dihydroxy-2-(3-phenylprop-1-enyl)isophthalonitril, 4'-fluor-3,4-dihydroxy-3'-methoxybiphenyl-2,6-dicarbonitril, 5-(2,6-dicyano-3,4-dihydroxyphenyl)thiophen-2-carboxylsyre, 3.4- dihydroxy-4'-(methylsulfonyl)biphenyl-2,6-dicarbonitril, 3.4- dihydroxy-4'-propoxybiphenyl-2,6-dicarbonitril, 2',6'-dicyano-3',4'-dihydroxybiphenyl-4-carboxylsyre, 4'-chlor-3,4-dihydroxy-3'-methylbiphenyl-2,6-dicarbonitril, 4.5- dihydroxy-2-(5-phenylthiophen-2-yl)isophthalonitril, 3.4- dihydroxy-4'-isopropylbiphenyl-2,6-dicarbonitril, 3.4- dihydroxy-4'-propylbiphenyl-2,6-dicarbonitril, 4.5- dihydroxy-2-(1-phenylvinyl)isophthalonitril, 2',6'-dicyano-3',4'-dihydroxybiphenyl-2-carboxylsyre, 4-(2,6-dicyano-3,4-dihydroxybenzyl)benzoesyre, (E)-4,5-dihydroxy-2-(4-methoxystyryl)isophthalonitril, 3.4- dihydroxy-3',4'-dimethylbiphenyl-2,6-dicarbonitril, (E)-4,5-dihydroxy-2-(4-methylstyryl)isophthalonitril, 4.5- dihydroxy-2-(6-hydroxynaphthalen-2-yl)isophthalonitril, 4'-fluor-3,4-dihydroxy-3'-methylbiphenyl-2,6-dicarbonitril, 4.5- dihydroxy-2-(3-methylbut-2-en-2-yl)isophthalonitril, 2-(2,5-dimethylthiophen-3-yl)-4,5-dihydroxyisophthalonitril, 2-(2,3-difluor-4-methylbenzyl)-4,5-dihydroxyisophthalonitril, 2-(4-(2,6-dicyano-3,4-dihydroxybenzyl)phenyl)propionsyre, (E)-2-(3-cyclopentylprop-1-enyl)-4,5-dihydroxyisophthalonitril, 4.5- dihydroxy-2-(1 -isobutyl-1 H-pyrazol-4-yl)isophthalonitril, 2-(4-(2,6-dicyano-3,4-dihydroxyphenyl)-1H-pyrazol-1-yl)eddikesyre, 4.5- dihydroxy-2-(1 -methyl-1 H-pyrazol-4-yl)isophthalonitril, 4.5- dihydroxy-2-(3-methoxyprop-1-ynyl)isophthalonitril, (E)-4,5-dihydroxy-2-(2-(thiophen-3-yl)vinyl)isophthalonitril, (E)-2-(2-cyclopropylvinyl)-4,5-dihydroxyisophthalonitril, 2',6'-dicyano-3',4'-dihydroxybiphenyl-4-carboxannid, 3.4- dihydroxy-3',4'-dimethoxybiphenyl-2,6-dicarbonitril, 3.4- dihydroxy-3'-isopropylbiphenyl-2,6-dicarbonitril, 2-(2,3-dihydrobenzofuran-5-yl)-4,5-dihydroxyisophthalonitril, 4.5- dihydroxy-2-(6-methoxynaphthalen-2-yl)isophthalonitril, 4.5- dihydroxy-2-(4-(hydroxymethyl)benzyl)isophthalonitril, 2-(2,6-difluor-3-methylbenzyl)-4,5-dihydroxyisophthalonitril, 4.5- dihydroxy-2-(4-(trifluormethyl)phenylthio)isophthalonitril, 2-(2,4-dimethylphenylthio)-4,5-dihydroxyisophthalonitril, methyl-3-(4-(2,6-dicyano-3,4-dihydroxyphenylthio)phenyl)propionat, 4.5- dihydroxy-2-(p-tolyloxy)isophthalonitril, (E)-2-(2,4-difluorstyryl)-4,5-dihydroxyisophthalonitril, (E)-4,5-dihydroxy-2-(3-(trifluormethyl)styryl)isophthalonitril, (E)-4,5-dihydroxy-2-(4-methylpent-1-enyl)isophthalonitril, (E)-2-(3,5-difluorstyryl)-4,5-dihydroxyisophthalonitril, 2-(4-(2,6-dicyano-3,4-dihydroxybenzyl)phenyl)eddikesyre, 2- (4-chlorbenzyl)-4,5-dihydroxyisophthalonitril, 3.4- dihydroxy-4'-methylbiphenyl-2,6-dicarbonitril, 3- (4-(2,6-dicyano-3,4-dihydroxybenzyl)phenyl)propionsyre, 4.5- dihydroxy-2-(4-(trifluormethyl)benzyl)isophthalonitril, (E)-4,5-dihydroxy-2-(4-(trifluormethyl)styryl)isophthalonitril, 4.5- dihydroxy-2-(p-tolylsulfinyl)isophthalonitril, 4- (2,6-dicyano-3,4-dihydroxyphenylthio)benzoesyre, 2-(4-ethylphenylthio)-4,5-dihydroxyisophthalonitril, 2-(4-chlorphenylthio)-4,5-dihydroxyisophthalonitril, 4.5- dihydroxy-2-(o-tolylthio)isophthalonitril, methyl-4-(2,6-dicyano-3,4-dihydroxyphenylthio)benzoat, 2-(2-chlorphenylthio)-4,5-dihyd roxyisophthalonitril, methyl-2-(2,6-dicyano-3,4-dihydroxyphenylthio)benzoat, 2-(4-(2,6-dicyano-3,4-dihydroxyphenylthio)phenyl)eddikesyre, 2- (2,6-dicyano-3,4-dihydroxyphenylthio)benzoesyre, 3- (4-(2,6-dicyano-3,4-dihydroxyphenylthio)phenyl)propionsyre, 4.5- dihydroxy-2-(4-methoxyphenylthio)isophthalonitril, methyl-2-(4-(2,6-dicyano-3,4-dihydroxybenzyl)phenyl)acetat, 4.5- dihydroxy-2-(3-methoxyphenylthio)isophthalonitril, methyl-4-(2,6-dicyano-3,4-dihydroxyphenoxy)benzoat, 4.5- dihydroxy-2-(pyridin-4-ylthio)isophthalonitril, 3-(2,6-dicyano-3,4-dihydroxyphenylthio)benzoesyre, 2-(4-cyanophenylthio)-4,5-dihydroxyisophthalonitril, 4.5- dihydroxy-2-(naphthalen-2-ylthio)isophthalonitril, 2-(4-(2,6-dicyano-3,4-dihydroxybenzyl)phenyl)-N,N-diethylacetamid, 2-(4-ethylphenoxy)-4,5-dihydroxyisophthalonitril, 2-(4-acetylphenoxy)-4,5-dihydroxyisophthalonitril, 4.5- dihydroxy-2-(1-oxo-2,3-dihydro-1 H-inden-5-yloxy)isophthalonitril, 2-(2',6'-dicyano-3',4'-dihydroxybiphenyl-4-yl)eddikesyre, 2-(2,4-dimethylphenoxy)-4,5-dihydroxyisophthalonitril, 2-(4-chlorphenoxy)-4,5-dihydroxyisophthalonitril, 4.5- dihydroxy-2-(4-(trifluormethyl)phenoxy)isophthalonitril, 4.5- dihydroxy-2-(1 H-inden-3-yl)isophthalonitril, 4.5- dihydroxy-2-(morpholinomethyl)isophthalonitril, 2-((diethylamino)methyl)-4,5-dihydroxyisophthalonitril-hydrochlorid, 4.5- dihydroxy-2-(((2-hydroxyethyl)amino)methyl)isophthalonitril-hydrochlorid (1:1), 4,5-dihydroxy-2-(3-hydroxypropyl)isophthalonitril, 2-amino-4,5-dihydroxyisophthalonitril, 4.5- dihydroxy-2-(pyrrolidin-1-yl)isophthalonitril, 2-(2,6-dimethylmorpholino)-4,5-dihydroxyisophthalonitril, 4.5- dihydroxy-2-morpholinoisophthalonitril, 4.5- dihydroxy-2-(isopropylamino)isophthalonitril, 4.5- dihydroxy-2-(3-methoxypropylamino)isophthalonitril, 2,4,5-trihydroxyisophthalonitril, 2-ethyl-4,5-dihydroxyisophthalonitril, 3.4- dihydroxy-4'-methoxybiphenyl-2,6-dicarbonitril, 3.4- dihydroxy-3'-(morpholin-4-carbonyl)biphenyl-2,6-dicarbonitril, N-butyl-2',6'-dicyano-3',4'-dihydroxybiphenyl-4-carboxamid, 2-(3,3-dimethylbutyl)-4,5-dihydroxyisophthalonitril, 4.5- dihydroxy-2-(piperidin-1-yl)isophthalonitril, 2-(hexylamino)-4,5-dihydroxyisophthalonitril, 2-(cyclohexylamino)-4,5-dihydroxyisophthalonitril, 4.5- dihydroxy-2-(2-methoxyethylamino)isophthalonitril, 2-(4-benzylpiperidin-1-yl)-4,5-dihydroxyisophthalonitril, 4.5- dihydrOxy-2-(pentan-3-ylamino)isophthalonitril, (E)-2-(4-ethylbenzylidenamino)-4,5-dihydroxyisophthalonitril, (E)-4,5-dihydroxy-2-(4-methoxybenzylidenamino)isophthalonitril, (E)-2-(4-fluorbenzylidenamino)-4,5-dihydroxyisophthalonitril, 4.5- dihydroxy-2-tosylisophthalonitril, 4-(2,6-dicyano-3,4-dihydroxyphenoxy)benzoesyre, 2-(benzo[d]thiazol-2-ylthio)-4,5-dihydroxyisophthalonitril, 2-(4-fluorphenylthio)-4J5-dihydroxyisophthalonitril, 2-(biphenyl-4-ylmethyl)-4,5-dihyd roxyisophthalonitril, 2-(4-chlor-2-methylbenzyl)-4,5-dihydroxyisophthalonitril, 2-(2-ethylbenzyl)-4,5-dihydroxyisophthalonitril, 2-(2,3-dihydro-1 H-inden-5-yloxy)-4,5-dihydroxyisophthalonitril, enantiomer A af 4.5- dihydroxy-2-(p-tolylsulfinyl)isophthalonitril, enantiomer B af 4.5- dihydroxy-2-(p-tolylsulfinyl)isophthalonitril, 2-((cyclohexylmethyl)amino)-4,5-dihyd roxyisophthalonitril, 4.5- dihydroxy-2-(4-phenoxyphenylthio)isophthalonitril, 4.5- dihydroxy-2-(pyridin-3-yl)isophthalonitril, 4.5- dihydroxy-2-(4-(2,2,2-trifluorethyl)benzyl)isophthalonitril, 4.5- dihydroxy-2-(4-methyl-2-(trifluormethyl)benzyl)isophthalonitril, 4.5- dihydroxy-2-((4-(morpholin-4-carbonyl)phenyl)thio)isophthalonitril, 4.5- dihydroxy-2-(methyl(p-tolyl)amino)isophthalonitril eller 4.5- dihydroxy-2-((6-methoxynaphthalen-2-yl)methyl)isophthalonitril.
17. Forbindelse ifølge krav 1, hvor forbindelsen er 4,5-dihydroxy-2-(1-methyl-1H-pyrrol-2-yl)isophthalonitril.
18. Forbindelse ifølge krav 1, hvor forbindelsen er 4'-tert-butyl-3,4-dihydroxybiphenyl-2,6-dicarbonitril.
19. Forbindelse ifølge krav 1, hvor forbindelsen er 3.4- dihydroxy-2',5'-dimethylbiphenyl-2,6-dicarbonitril.
20. Forbindelse ifølge krav 1, hvor forbindelsen er (E)-2-(3,3-dimethylbut-1-enyl)-4,5-dihydroxyisophthalonitril.
21. Forbindelse ifølge krav 1, hvor forbindelsen er (E)-4,5-dihydroxy-2-(prop-1-enyl)isophthalonitril.
22. Forbindelse ifølge krav 1, hvor forbindelsen er 4'-ethyl-3,4-dihydroxybiphenyl-2,6-dicarbonitril.
23. Forbindelse ifølge krav 1, hvor forbindelsen er 4.5- dihydroxy-2-(4-methylbenzyl)isophthalonitril.
24. Forbindelse ifølge krav 1, hvor forbindelsen er 4.5- dihydroxy-2-(2-methoxybenzyl)isophthalonitril.
25. Forbindelse ifølge krav 1, hvor forbindelsen er 2-(3,5-dimethylbenzyl)-4,5-dihydroxyisophthalonitril.
26. Forbindelse ifølge krav 1, hvor forbindelsen er 2-(4-ethylbenzyl)-4,5-dihydroxyisophthalonitril.
27. Forbindelse ifølge krav 1, hvor forbindelsen er 4.5- dihydroxy-2-(2-methylprop-1-enyl)isophthalonitril.
28. Forbindelse ifølge krav 1, hvor forbindelsen er 4.5- dihydroxy-2-vinylisophthalonitril.
29. Forbindelse ifølge krav 1, hvor forbindelsen er 4.5- dihydroxy-2-(prop-1-en-2-yl)isophthalonitril.
30. Forbindelse ifølge krav 1, hvor forbindelsen er 2-(2-ethoxythiazol-5-yl)-4,5-dihydroxyisophthalonitril.
31. Forbindelse ifølge krav 1, hvor forbindelsen er 2-allyl-4,5-dihyd roxyisophthalonitril.
32. Forbindelse ifølge krav 1, hvor forbindelsen er 3.4- dihydroxy-4'-isopropylbiphenyl-2,6-dicarbonitril.
33. Forbindelse ifølge krav 1, hvor forbindelsen er 3.4- dihydroxy-4'-propylbiphenyl-2,6-dicarbonitril.
34. Forbindelse ifølge krav 1, hvor forbindelsen er 3.4- dihydroxy-3',4'-dimethylbiphenyl-2,6-dicarbonitril.
35. Forbindelse ifølge krav 1, hvor forbindelsen er 2-(2,5-dimethylthiophen-3-yl)-4,5-dihydroxyisophthalonitril.
36. Forbindelse ifølge krav 1, hvor forbindelsen er 4.5- dihydroxy-2-(1 -isobutyl-1 H-pyrazol-4-yl)isophthalonitril.
37. Forbindelse ifølge krav 1, hvor forbindelsen er 3,4-dihydroxy-4'-methylbiphenyl-2,6-dicarbonitril.
38. Forbindelse ifølge krav 1, hvor forbindelsen er 2-(4-ethylphenylthio)-4,5-dihydroxyisophthalonitril.
39. Forbindelse ifølge krav 1, hvor forbindelsen er 4.5- dihydroxy-2-(o-tolylthio)isophthalonitril.
40. Forbindelse ifølge krav 1, hvor forbindelsen er 4.5- dihydroxy-2-(4-methoxyphenylthio)isophthalonitril.
41. Forbindelse ifølge krav 1, hvor forbindelsen er 3,4-dihydroxy-4'-methoxybiphenyl-2,6-dicarbonitril.
42. Forbindelse ifølge krav 1, hvor forbindelsen er 2-(2-ethylbenzyl)-4,5-dihydroxyisophthalonitril.
43. Forbindelse ifølge et hvilket som helst af kravene 1 til 42 til anvendelse som lægemiddel.
44. Forbindelse ifølge et hvilket som helst af kravene 1 til 42 til anvendelse ved behandling afen sygdom eller tilstand, hvor et COMT-hæmmende middel er indiceret som værende egnet.
45. Forbindelse ifølge krav 44, hvor sygdommen er Parkinsons sygdom.
46. Farmaceutisk sammensætning, der som aktiv bestanddel omfatter mindst én forbindelse ifølge et hvilket som helst af kravene 1 til 42 og en farmaceutisk acceptabel bærer, et farmaceutisk acceptabelt fortyndingsmiddel, en farmaceutisk acceptabel excipiens eller en blanding deraf.
47. Farmaceutisk sammensætning ifølge krav 46, hvor sammensætningen yderligere omfatter mindst én anden aktiv bestanddel.
48. Farmaceutisk sammensætning ifølge krav 47, hvor sammensætningen omfatter levodopa og carbidopa.
DK13730284.0T 2012-05-24 2013-05-23 Forbindelser, som hæmmer aktiviteten af catechol-o-methyltransferase DK2855426T3 (da)

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