Patent EP-0177078-A1 (EP)
Inventor: VAN WIJNGAARDEN INEKE
IPC: C07D211/46
Filed: 1985-09-04
Abstract: The invention relates to new spasmolytically active tertiary amine derivatives and the salts thereof, of the formula (1)wherein the symbols have the following meanings:Ⓐ is phenyl, or a 5- or 6-membered aromatic group containing 1 or 2 of the following hetero atoms: oxygen and or sulphur and or nitrogen;R<sub>1</sub> and R<sub>2</sub> may be equal or different and are hydrogen, alkyl having 1-3 carbon atoms, hydroxyalkyl or mercaptoalkyl having 1-3 carbon atoms wich may be etherified or esterified, alkoxy having 1-3 carbon atoms, the group S(O)<sub>m</sub>-R<sub>9</sub>, wherein Rg is an alkyl group having 1-3 carbon atoms, and m has the value 0, 1 or 2, a group - NR<sub>10</sub>R<sub>11</sub>, wherein R<sub>io</sub> and R<sub>11</sub> represent alkyl having 1-3 carbon atoms, or together may form a saturated, 5 or 6 membered ring which may contain a sulphur, oxygen or nitrogen atom as second hetero atom, R, and R<sub>2</sub> represent an optionally derivated hydroxy group, mercapto group or amino group, or a halogen atom, or R<sub>1</sub> and R<sub>2</sub> together may form a 5- or 6-membered ring optionally containing 1 or 2 oxygen, and/or nitrogen and/or sulphur atoms, which ring is condensed with Ⓐ, is fully or partly unsaturated and may be substituted by one or more alkyl groups having 1-3 carbon atoms, optionally etherified or esterified hydroxyalkyl having 1-3 carbon atoms or an oxygen atom;R<sub>3</sub> is a hydrogen atom or, together with R<sub>4</sub>, may form a ring consisting of 6 or 7 carbon atoms;R<sub>4</sub> is a hydrogen atom or alkyl group having 1-3 carbon atoms;R<sub>5</sub> is a straight, branched or cyclic alkyl group having 1-4 carbon atoms;R<sub>6</sub> is a straight or branched, saturated or unsaturated alkylene group having a chain length of 2-6 carbon atoms;Z is the group NR<sub>12</sub>, wherein R<sub>12</sub> is a hydrogen atom or an alkyl group having 1-3 carbon atoms, or Z is an oxygen atom;n has the value 0 or 1;X is a carbonyl group, thiocarbonyl group or S0<sub>2</sub> group.R<sub>7</sub> and R<sub>8</sub>, together with the nitrogen atom to which they are bound, constitute a fully or partly saturated heterocyclic ring consisting of 5-8 ring atoms and which may comprise in addition an 0, N or S-atom as the second hetero atom, and may be substituted by 1 or 2 alkyl groups having 1-3 carbon atoms, an alkylene bridge of 2 or 3 carbon atoms across the ring. or an oxygen atom which, in case of a keto function may optionally have the form of a ketal or oxim, or the ring formed by R<sub>7</sub> and R<sub>8</sub> may be substituted directly or via an alkylene chain of 1-3 carbon atoms, with 1 or 2 of the following substituents: phenyl or phenyl substituted with halogen, alkyl or alkoxy having 1-3 carbon atoms, hydroxy, amino, mono- or dialkylamino having 1-3 carbon atoms in the alkyl group(s), alkanoyl or thioalkanoyl having 1-3 carbon atoms, hydroxy alkanoyl having 1-3 carbon atoms, benzoyl, optionally esterified or etherified hydroxy or mercapto, optionally mono- or dialkyl and/or -acyl substituted amino, carbalkoxy having 1-3 carbon atoms in the alkoxy group, a carbamoyl, thiocarbamoyl, sulfamoyl or carbamoyloxy group of which the nitrogen atom may be substituted by 1 or 2 alaoxy groups having 1-3 carbon atoms and/or alkyl groups having 1-5 carbon atoms, which, optionally via a nitrogen, oxygen or sulphur atom, may form a substituted or non- sabstituted saturated heterocyclic grohup consisting of 5 or 6 ring atoms