Patent EP-0178919-B1 (EP)
IPC: C07C307/10
Filed: 1985-10-16
Granted: 1988-12-21
Abstract: The invention provides compounds of the general formula (I)whereinAr represents a phenyl group optionally substituted by one or more substituents selected from halogen atoms, or the groups C<sub>1-6</sub> alkyl, C<sub>1-6</sub> alkoxy, nitro, -(CH<sub>2</sub>)<sub>q</sub>R, [where R is hydroxy, -NR<sup>3</sup>R<sup>4</sup> (where R<sup>3</sup> and R<sup>4</sup> each represents a hydrogen atom, or a C<sub>1-4</sub> alkyl group, or-NR<sup>3</sup>R<sup>4</sup> forms a saturated heterocyclic amino group which has 5-7 ring members and optionally contains in the ring one or more atoms selected from -0- or -S- or a group -NH- or -N(CH<sub>3</sub>)-). -NR<sup>5</sup>COR<sup>6</sup> (where R<sup>5</sup> represents a hydrogen atom or a C<sub>1-5</sub> alkyl group, and R<sup>6</sup> represents a hydrogen atom or a C<sub>1-4</sub> alkyl, C<sub>1-4</sub> alkoxy, phenyl or-NR<sup>3</sup>R<sup>4</sup> group), -NR<sup>6</sup>SO<sub>2</sub>R<sup>7</sup> (where R<sup>7</sup> represents a C<sub>1-4</sub> alkyl, phenyl or -NR<sup>3</sup>R<sup>4</sup> group), -COR<sup>8</sup> (where R<sup>8</sup> represents hydroxy, C<sub>1-4</sub> alkoxy or-NR<sup>3</sup>R<sup>4</sup>), -SR<sup>8</sup> (where R<sup>9</sup> is a hydrogen atom, or a C<sub>1-4</sub> alkyl or phenyl group),-SOR<sup>9</sup>,-SO<sub>2</sub>R<sup>9</sup>, or -CN, and q represents an integer from 0 to 31, -(CH<sub>2</sub>)<sub>r</sub>R<sup>10</sup>, [where R<sup>10</sup> is a C<sub>1-4</sub> alkoxy group and r represents an integer from 1 to 3] or -O(CH<sub>2</sub>)<sub>t</sub>T<sup>11</sup> [where R" represents a hydroxy or C<sub>1-4</sub> alkoxy group and t is 2 or 3] or Ar is a phenyl group substituted by an alkylenedioxy group of formula -O(CH<sub>2</sub>)<sub>p</sub>O-, where p represents 1 or 2; R' and R<sup>2</sup> each represent a hydrogen atom or a C<sub>1-3</sub> alkyl group with the proviso that the sum total of carbon atoms inR<sup>1</sup> and R<sup>2</sup> is not more than 4;X represents a C<sub>1-7</sub> alkylene, C<sub>2</sub> alkenylene or C<sub>2-7</sub> alkynylene chain;Y represents a bond, or a C<sub>1-6</sub> alkylene, C<sub>2-6</sub> alkenylene or C<sub>2-6</sub> alkynylene chain with the proviso that the sum total of carbon atoms in X and Y is 2 to 10;Q represents a group R<sup>12</sup>CO-, R<sup>12</sup>NHCO-, R<sup>12</sup>R<sup>13</sup>NSO<sub>2</sub>- or R<sup>14</sup>SO<sub>2</sub>, where R<sup>12</sup> and R<sup>13</sup> each represents a hydrogen atom or a C<sub>1-3</sub> alkyl group, and R<sup>14</sup> represents a C<sub>1-4</sub> alkyl group, with the proviso that when X represents C<sub>1-7</sub> alkylene, and Y represents a bond or C<sub>1-6</sub> alkylene, then the group Ar does not represent an unsubstituted phenyl group or a phenyl group substituted by one or more substituents selected solely from halogen atoms or C<sub>1-6</sub> alkyl or C<sub>1-6</sub> alkoxy groups or an alkylenedioxy group -O(CH<sub>2</sub>)<sub>p</sub>O-;and physiologically acceptable salts and solvates thereof.The compounds have a selective stimulant action at β<sub>2</sub>-adrenoreceptors and may be used, inter alia, in the treatment of disease associated with reversible airways obstruction such as asthma and chronic bronchitis.