Imperial Chemical Industries Limited

Leslie H Smith

Michael S Large

Jeffrey J Barlow

Alkanolamine derivatives of the formula ##STR1## wherein Ar is phenyl or napthyl which is unsubstituted or which bears one or two defined substituents, or Ar is certain defined heterocyclic or bicyclic aromatic systems; wherein R.sup.1 is halogen, cyano, trifluoromethyl or trifluoromethylthio; wherein either R.sup.2 and R.sup.3 each is hydrogen or alkyl, or R.sup.2 is hydrogen and R.sup.3 is cycloalkyl or cycloalkyl-alkyl, or R.sup.2 and R.sup.3 are joined to form, together with the adjacent nitrogen atom, a heterocyclic group; wherein either R.sup.4 is hydrogen and R.sup.5 is hydrogen or alkyl, or R.sup.4 is hydrogen and R.sup.5 and R.sup.6 are joined together to form alkylene, or R.sup.4, R.sup.5 and R.sup.6 are joined together to form alk-1-yl-.omega.-ylidene; wherein either R.sup.6 and R.sup.7 each is hydrogen or alkyl, or R.sup.6 is joined to R.sup.4 or to R.sup.4 and R.sup.5 as defined above and R.sup.7 is hydrogen or alkyl, or R.sup.6 and R.sup.7 are joined together to form alkylene, or one of R.sup.6 and R.sup.7 is hydrogen or alkyl and the other of R.sup.6 and R.sup.7 is joined to A as defined below; and wherein either A is alkylene, cycloalkylene or cycloalkylene-alkylene, or wherein A together with either R.sup.6 and its accompanying nitrogen atom, or R.sup.7 and its accompanying nitrogen atom, form pyrrolidine-diyl or piperidine-diyl; and acid-addition salts thereof; processes for their manufacture and pharmaceutical compositions containing them. The compounds possess .beta.-adrenergic blocking and/or diuretic activity.

Alkanolamine derivatives

Novel 1-aryloxy-3-amidoamidoalkylamino-2-propanol derivatives, processes for their manufacture, pharmaceutical compositions containing them and methods of using them in the treatment of heart diseases. Representative of the compounds disclosed is 1-(o-cyanophenoxy)-3-.beta.-(2-thenamidoacetamido)ethylaminopropan-2-ol.

Novel alkanolamine derivatives of the formula: ##STR1## wherein Ar is phenyl or naphthyl which is unsubstituted or which bears one or two substituents selected from halogen, trifluoromethyl, hydroxy, amino, nitro, carbamoyl, carbamoylmethyl and cyano, and alkyl, alkenyl, alkoxy, alkenyloxy, alkylthio, alkanoyl and alkanoylamino each of up to 6 carbon atoms, or Ar is 4-indolyl, 4-benzo[b]thienyl, 5-benzo[1,4]dioxanyl, 4- or 5-indanyl, 5- or 6- 1,2,3,4-tetrahydronaphthyl), 2,3-dihydroxy-1,2,3,4-tetrahydronaphth-5-yl or 4- morpholino-1,2,5-thiadiazol-3-yl;

Novel 1-heterocyclyloxy- or 1-aryloxy-3-amido-alkylamino-2-propanol derivatives, processes for their manufacture, pharmaceutical compositions containing them and methods of using them in the treatment of heart diseases. The compounds possess .beta.-adrenergic blocking activity. Representative of the compounds disclosed is 1-(4-indolyloxy)-3-.beta.-isobutyramidoethylamino-2-propanol.

Novel 1-heterocyclyloxy- or 1-aryloxy-3-amidoalkylamino-2-propanol derivatives, processes for their manufacture, pharmaceutical compositions containing them and methods of using them in the treatment of heart diseases. The compounds possess .beta.-adrenergic blocking activity. Representative of the compounds disclosed is 1-(4-indolyloxy)-3-.beta.-isobutyramidoethylamino-2-propanol.

Novel 1-aryloxy-3-amidoamidoalkylamino-2-propanol derivatives, processes for their manufacture, pharmaceutical compositions containing them and methods of using them in the treatment of heart diseases. Representative of the compounds disclosed is 1-(o-cyanophenoxy)-3-.beta.-(benzamidoacetamido)ethylaminopropan-2-ol.

Novel 1-heterocyclyloxy-or 1-aryloxy-3-amidoalkylamino-2-propanol derivatives, processes for their manufacture, pharmaceutical compositions containing them and methods of using them in the treatment of heart diseases. The compounds possess .beta.-adrenergic blocking activity. Representative of the compounds disclosed is 1-(4-indolyloxy)-3-.beta.-isobutyramidoethylamino-2-propanol.

1-Aryloxy-3-(tri- or tetra-acylamido)-alkylamino-propan-2-ol derivatives, processes for their manufacture and pharmaceutical compositions containing them. The compounds possess .beta.-adrenergic blocking activity and are useful in the treatment of heart diseases such as angina pectoris, cardiac arrhythmias and hypertension. Representative of the compounds disclosed is 1-(o-chlorophenoxy)-3-.beta.-(phenylacetamido-.gamma.-butyramido-.gamma.-b utyramido)-ethylamino-2-propanol.

Novel 1-aryloxy-3-carbamoylalkylamino-2-propanol derivatives, processes for their manufacture, pharmaceutical compositions containing them and methods of using them in the treatment of heart diseases. The compounds possess .beta.-adrenergic blocking activity. Representative of the compounds disclosed is 1-(2-cyanophenoxy)-3-.beta.-(N-2-furfurylcarbamoyl)ethylamino-2-propanol.

Novel 1-aryloxy-3-amidoalkylamino-2-propanol derivatives, processes for their manufacture, pharmaceutical compositions containing them and methods of using them in the treatment of heart diseases. The compounds possess .beta.-adrenergic blocking activity and some of them additionally possess cardiac stimulant activity. Representative of the compounds disclosed is 1-(2-fluorophenoxy)-3-.beta.-(3-benzylureido) ethylamino-2-propanol.

1-Aryloxy-3-aminoalkylamino-2-propanol derivatives, processes for their manufacture, pharmaceutical compositions containing them and methods of using them in the treatment of heart diseases. The compounds possess .beta.-adrenergic blocking activity and some of them additionally possess cardiac stimulant activity. Representative of the compounds disclosed is 1-(2-cyanophenoxy)-3-.beta.(4-hydroxyphenylacetamido)ethylamino-2-propanol .

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Macclesfield, United Kingdom

Leslie H Smith