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US 2011/0086852 A2Published application
Pharmaceutical compounds
AssigneeOrion Corporation
InventorsMarko AHLMARK, Reijo BACKSTROM, Anne LUIRO, Jarmo PYSTYNEN, Eija TIAINEN
Life of this patent
Estimating the term…
Abstract
Compounds of formula (I), wherein R1-R4, X, Y and Z are as defined in claims, exhibit COMT enzyme inhibiting activity and are thus useful as COMT inhibitors.
Claims25
A compound of formula I,
- wherein
- R2 is in a position ortho to R3 and R1 is in a position ortho to R2
- or R1 is in a position ortho to R3 and R4 is in a position ortho to R1;
- R1 is cyano or nitro;
- R2 is hydroxy;
- R3 is hydroxy;
- R4 is H, (C1-C6)alkyl, halo(C1-C6)alkyl, cyano, formyl, (C1-C6)alkyl-(C═O)—,
- halogen or nitro;
- the dotted line represents a single or a double bond;
- two of X, Y or Z are independently CR5(R6)m, N(R7)n, O or S and one of X, Y or
- Z is N(R7)n, O or S;
- m is, independently at each occurrence, 0 or 1;
- n is, independently at each occurrence, 0, 1 or 2;
- R5 is, independently at each occurrence, H, (C1-C6)alkyl, (C2-C6)alkenyl, halogen, hydroxy, (C1-C6)alkoxy, halo(C1-C6)alkyl, hydroxy(C1-C6)alkyl, (C1-C6)alkyl-(C═O)—, (C1-C8)alkoxy-(C═O)—, cyano, formyl, (C1-C6)alkyl-(C═S)—, (R8)2N—(C═S)—, R8—(C═NR8)—, carboxy, (C3-C7)cycloalkyl, heterocyclyl, aryl, heteroaryl, heterocyclyl-(C═O)—, aryl(C1-C6)alkyl, (R8)2N—, (R8)2N—(C1-C6)alkyl, (R8)2N—(C═O)—, (C1-C6)alkyl-S—, R9—(S═O)—, R9—(O═S═O)—, (C1-C6)alkoxy(C1-C6)alkyl, (C1-C6)alkoxy-(C═O)—(C1-C6)alkyl, (C1-C6)alkyl-(C═O)—O—, (C1-C6)alkyl-(C═O)—O—(C1-C6)alkyl, hydroxy(C1-C6)alkoxy(C1-C6)alkyl, (C1-C6)alkyl-S—(C1-C6)alkyl, (C1-C6)alkyl-S—(C═O)—, (C3-C7)cycloalkyl(C1-C6)alkyl, aryloxy, aryloxy(C1-C6)alkyl, aryl(C1-C6)alkoxy, aryl(C1-C6)alkoxy(C1-C6)alkyl or heterocyclyl-(C═S)—, wherein said (C3-C7)cycloalkyl, heterocyclyl, aryl or heteroaryl as such or as part of another group is unsubstituted or substituted with 1, 2 or 3 substituent(s) each independently being (C1-C6)alkyl, halogen, hydroxy, carboxy, (C1-C6)alkoxy or (R8)2N—;
- R6 is, independently at each occurrence, H, (C1-C6)alkyl, halogen, hydroxy, hydroxy(C1-C6)alkyl or (C1-C6)alkoxy;
- or R5 and R6 both attached to the same carbon ring atom form, together with the carbon ring atom to which they are attached, a —(C═O)— group;
- or R5 and R6 both attached to the same carbon ring atom form, together with the carbon ring atom to which they are attached, C═C(R8)2;
- or R5 and R6 both attached to the same carbon ring atom form, together with the carbon ring atom to which they are attached, a 5, 6 or 7 membered saturated or unsaturated carbocyclic ring, wherein said ring is unsubstituted or substituted with 1 or 2 substituent(s) each independently being (C1-C6)alkyl, halogen, hydroxy, (C1-C6)alkoxy or carboxy;
- R7 is, independently at each occurrence, H, (C1-C6)alkyl, (C3-C7)cycloalkyl, (C1-C6)alkoxy, aryl or O−, wherein said (C3-C7)cycloalkyl or aryl is unsubstituted or substituted with 1, 2 or 3 substituent(s) each independently being (C1-C6)alkyl, halogen, hydroxy, (C1-C6)alkoxy or carboxy;
- or R5 and R5, R5 and R7, or R7 and R7 attached to adjacent ring atoms form, together with the ring atoms to which they are attached, a condensed 5, 6 or 7 membered saturated or unsaturated carbocyclic ring or a condensed 5, 6 or 7 membered saturated or unsaturated heterocyclic ring containing 1 or 2 heteroatom(s) selected from N, O and S, wherein said carbo- or heterocyclic ring is unsubstituted or substituted with 1 or 2 substituent(s) each independently being (C1-C6)alkyl, halogen, hydroxy, (C1-C6)alkoxy, carboxy or oxo;
- R8 is, independently at each occurrence, H, (C1-C6)alkyl, (C1-C6)alkoxy, aryl or aryl(C1-C6)alkyl, wherein said aryl as such or as part of another group is unsubstituted or substituted with 1 or 2 substituent(s) each independently being (C1-C6)alkyl, halogen, hydroxy, carboxy or (C1-C6)alkoxy;
- R9 is, independently at each occurrence, (C1-C6)alkyl, (R8)2N—, hydroxy or (C1-C6)alkoxy;
- or a pharmaceutically acceptable salt or ester thereof;
- with the proviso that the compound is not 2-benzyl-7-bromo-6-nitro-benzofuran-4,5-diol.
21 more elements
Dependencies are inferred from the claim text.