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US 10,336,740 B2Granted
Nitrocatechol derivatives as COMT inhibitors
AssigneeBial - Portela & Ca, S.A.
InventorsDavid Alexander Learmonth, Laszlo Erno Kiss, Pedro Nuno Leal Palma, Humberto dos Santos Ferreira, Patricio Manuel V. A. Soares Da Silva
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Abstract
New compounds of formula I are described. The compounds have potentially valuable pharmaceutical properties in the treatment of some central and peripheral nervous system disorders.
Claims16
A process for the preparation of compounds according to formula I,
- wherein
- R1 and R2 independently from each other represent hydrogen, optionally substituted lower alkanoyl or optionally substituted lower aroyl;
- R3 represents a pyridine N-oxide group according to the formula A, B or C, which is connected as indicated by the unmarked bond:
- comprising steps wherein a compound of formula IIA, IIB or IIC,
- wherein R4, R5, R6 and R7 independently from each other represent hydrogen, C1-C6-alkyl, C1-C6-thioalkyl, C1-C6-alkoxy, C6-C12-aryloxy, a C6-C12-thioaryl group, C1-C6-alkanoyl, a C7-C13-aroyl group, amino, C1-C6-alkylamino, C1-C6-dialkylamino, C3-C12-cycloalkylamino, C3-C12-heterocycloalkylamino, C1-C6-alkylsulphonyl, C6-C12-arylsulphonyl, halogen, C1-C6-haloalkyl, trifluoromethyl, cyano, nitro or a heteroaryl group;
- or where two or more of residues R4, R5, R6 and R7 taken together represent aliphatic or heteroaliphatic rings or aromatic or heteroaromatic rings,
- is subjected to cyclisation with a compound of formula III,
- wherein R8 and R9 independently from each other represent hydrogen or suitable protective groups for aromatic hydroxyl groups, under conditions suitable to produce oxadiazole derivatives of formula IVA, IVB or IVC,
- optionally followed by removal of the protecting groups R8 and or R9.
6 more elements
A process for the preparation of compounds according to formula I,
- wherein
- R1 and R2 independently from each other represent hydrogen, optionally substituted lower alkanoyl or optionally substituted lower aroyl;
- R3 represents a pyridine group according to the formula A, B or C, which is connected as indicated by the unmarked bond:
- comprising steps wherein a compound of formula VA, VB, or VC,
- wherein R4, R5, R6 and R7 independently from each other represent hydrogen, C1-C6-alkyl, C1-C6-thioalkyl, C1-C6-alkoxy, C6-C12-aryloxy, a C6-C12-thioaryl group, C1-C6-alkanoyl, a C7-C13-aroyl group, amino, C1-C6-alkylamino, C1-C6-dialkylamino, C3-C12-cycloalkylamino, C3-C12-heterocycloalkylamino, C1-C6-alkylsulphonyl, C6-C12-arylsulphonyl, halogen, C1-C6-haloalkyl, trifluoromethyl, cyano, nitro or a heteroaryl group;
- or where two or more of residues R4, R5, R6 and R7 taken together represent aliphatic or heteroaliphatic rings or aromatic or heteroaromatic rings,
- is subjected to cyclisation with a compound of formula III
- under conditions suitable to produce oxadiazole derivatives of formula VIA, VIB or VIC,
- followed by oxidation of the pyridyl nitrogen atom to give a compound according to formula IVA, IVB or IVC,
- optionally followed by removal of the protecting groups R8 and/or R9, wherein R8 and R9 independently from each other represent hydrogen or suitable protective groups for aromatic hydroxyl groups.
7 more elements
Dependencies are inferred from the claim text.