3,5-disubstituted pyrocatechole derivatives

Details 3,5-disubstituted pyrocatechole derivatives 3,5-disubstituted pyrocatechole derivatives

C - Chemistry, Metallurgy

07

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C07C 205/45 (2006.01) C07C 45/29 (2006.01) C07C 45/30 (2006.01) C07C 45/46 (2006.01) C07C 45/67 (2006.01) C07C 47/565 (2006.01) C07C 47/575 (2006.01) C07C 49/83 (2006.01) C07C 49/84 (2006.01) C07C 69/017 (2006.01) C07C 205/23 (2006.01) C07C 205/37 (2006.01) C07C 205/43 (2006.01) C07C 205/44 (2006.01) C07C 205/56 (2006.01) C07C 205/59 (2006.01) C07D 209/12 (2006.01) C07D 213/53 (2006.01) C07D 215/14 (2006.01) C07D 217/16 (2006.01) C07D 241/44 (2006.01) C07D 253/07 (2006.01) C07D 265/36 (2006.01) C07D 277/24

Patent

CA 1302418

RAN 4007/50 Abstract The catechol derivatives of the general formula Image Ia wherein Ra signifies nitro or cyano, Rb signifies hydrogen or halogen, Rc signifies halogen, nitro, cyano or the group -(A)n-(Q)m-R1 or -(A)n-Q-R2, A signifies vinylene optionally substituted by lower alkyl, n signifies the number O or 1, m signifies the number 0 or 1, R1 signifies the group -COR3, a carbocyclic, aromatic group or an aromatic or partially unsaturated, heterocyclic group attached via a carbon atom, R2 signifies hydrogen or an optionally substituted, saturated or partially unsaturated, lower hydrocarbon residue, R3 signifies hydroxy, amino, an optionally substituted, saturated or partially unsaturated, lower hydrocarbon residue ateached via an oxygen atom or an imino or lower alkylimino group or a saturated, N-containing hetero- cyclic group attached via a ring nitrogen atom, Q signifies the group -CO- or >C=N-(Z)p-R4, Z signifies an oxygen atom or an imino group, p signifies the number 0 or 1 and R4 signifies hydrogen or a saturated or partially unsaturated. lower hydrocarbon residue which is optionally substituted and which is optionally attached via a carbonyl group, the ester and ether derivatives which are hydrolyzable under physiological conditions and the pharmaceutically acceptable salts thereof posses valuable pharmacological (Abstract cont'd) properties. In particular, they inhibit the enzyme catechol-O-methyltransferase (COMT), a soluble, magnesium dependent enzyme which catalyses the transference of the methyl group of S-adenosylmethionine to a catechol substrate, whereby the corresponding methyl ethers are formed. Suitable substrates which can be O-methylated by COMT and which can thus be deactivated are, for example, extraneuronal catecholamines and exogeneously-administered therapeutically active substances having a catechol structure. Formula Ia above embraces not only novel compounds, but also known compounds; the novel compounds can be manufactured according to methods known per se.

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