Novel compounds are disclosed having useful activity as bronchodilators of improved longevity of action and reduced incidence of side effects. These compounds are described by the formula: ##EQU1## wherein R.sub.1 is a member of the class consisting of tertiary butyl and cyclobutyl, and R.sub.2 is a hydrogen or 2 to 5 carbon atom acyl radical, and pharmaceutically acceptable salts thereof. The activity of these compounds is compared to previously known bronchodilators such as 1-(3', 5'-dihydroxyphenyl)-2-(isopropylamino)-ethanol, having the common name orciprenaline, and 1-(3', 4'-dihydroxyphenyl-2-isoproplyamino-ethanol, having the common name isoprenaline.
This is a continuation-in-part of our copending applications Ser. Nos. 55,791 and 55,676, filed July 17, 1970, which in turn are respectively both continuations-in-part of application Ser. No. 676,288, filed Oct. 18, 1967, now abandoned.
New bronchospasmolytically active compounds exhibiting long duration of action and reduced undesired side effects of the structural formula ##STR1## and therapeutically acceptable salts thereof, in which formula R is selected from the group consisting of --C(CH.sub.3).sub.3, ##STR2## R.sup.1 is selected from the group consisting of H and R.sup.2, R.sup.2 represents the radical of the formula ##STR3## wherein R.sup.3 is selected from the group consisting of (a) H (b) alkyl groups containing 1-3 carbon atoms ##STR4## wherein R.sup.5 is selected from the group consisting of (e) OH (b) alkoxy groups containing 1-3 carbon atoms and wherein R.sup.4 is selected from the group consisting of (a) H (b) alkyl groups containing 1-3 carbon atoms, with the proviso that R.sup.3 and R.sup.4 are combined as follows: processes for the preparation thereof, chemical intermediates at their preparation, pharmaceutical preparations containing them, and their medicinal use.
Pharmaceutical Combination Preparations useful as hypnotics which contain as pharmacological active compounds a beta-receptor-blocking compound and L-tryptophane or a non-toxic salt thereof.
The invention relates to weight gain-increasing compositions, particularly fodder supplement, premix, drinking water supplement, bolus and/or microcapsule containing 0.001 to 90% by weight of 1-(3,5-dihydroxyphenyl)-2-(tertiary butylamino)-ethanol or a physiologically acceptable acid addition salt thereof as active ingredient in admixture with inert solid and/or liquid carrier(s).
Intraocular pressure in warm-blooded animals is reduced by topically applying to the eye thereof, an effective ophthalmologically acceptable amount of a compound of the formula: ##STR1## wherein R represents a member selected from the group consisting of hydrogen or a C.sub.1 -C.sub.5 straight or branched alkyl group; and wherein R.sub.1 and R.sub.2, which may be the same or different, represents an acyl member selected from the group consisting of alkanoyl having 1-22 carbon atoms, alkenoyl having one or two double bonds and having 4-22 carbon atoms, ##STR2## having a total of 4-10 carbon atoms of which 3-7 are ring carbon atoms in cycloalkyl and wherein n is zero, one, or two, phenoxyacetyl, naphthalenecarbonyl, pyridinecarbonyl, ##STR3## wherein n is zero, one or two and phenyl is unsubstituted or is substituted by 1-3 alkyl having 1-4 carbon atoms, alkoxy having 1-4 carbon atoms, halo, trifluoromethyl, dialkylamino having 2-8 carbon atoms, and alkanoylamino having 1-6 carbon atoms; or an ophthalmologically acceptable acid addition salt thereof.
A method for the preparation of 1-(4'-amino-3',5'-dichlorophenyl)-2-alkyl)or dialkyl)aminoethanols. The method involves preparation of the above compounds from the corresponding aminoketones by reduction with hydrogen in the presence of platinum oxide catalyst and a promoter, such as stannous chloride.
