Claims
- 1. A pharmaceutical composition comprising as active ingredient a therapeutically effective amount of at least one alkanolamine selected from compounds of the formula: ##STR20## wherein A is alkylene of from 2 to 12 carbon atoms, wherein R.sup.1 is hydrogen, or alkyl, halogenoalkyl, alkenyl or cycloalkyl each of up to 10 carbon atoms, or aryl of the formula: ##STR21## wherein R.sup.2, R.sup.3, R.sup.12 and R.sup.13, which may be the same or different, each is hydrogen, halogen, hydroxy, amino, nitro or cyano, alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkylthio, cycloalkoxy, alkenyloxy, alkynyloxy or alkanoyl each of up to 6 carbon atoms, or aryl, aryloxy or aralkoxy each of up to 12 carbon atoms; or wherein R.sup.2 and R.sup.3 together, and/or R.sup.12 and R.sup.13 together, are trimethylene, tetramethylene, 1-oxotetramethylene, propenylene, but-2-enylene or buta-1,3-dienylene such that together with the adjacent benzene ring they form respectively indanyl, 5,6,7,8-tetrahydronaphthyl, 5-oxo-5,6,7,8-tetrahydronaphthyl, indenyl, 5,8-dihydronaphthyl or naphthyl; wherein R.sup.4 is hydrogen, hydroxy or hydroxymethyl or aralkoxy of up to 12 carbon atoms; wherein R.sup.14 is hydrogen, amino or dialkylamino of up to 12 carbon atoms; wherein X is carbonyl (--CO--) and wherein Y is a direct link, or alkylene, oxyalkylene or alkyleneoxy each of up to 6 carbon atoms, or except when R.sup.1 is hydrogen, oxygen; and the acid-addition salts thereof, in association with a pharmaceutically-acceptable diluent or carrier therefor.
- 2. A composition as claimed in claim 1 wherein A is ethylene, 1-methylethylene or 1,1-dimethylethylene, R.sup.1 is hydrogen, or alkyl, alkenyl or cycloalkyl each of up to 6 carbon atoms, or trifluoromethyl, monohydroxyphenyl or dihydroxyphenyl, Y is a direct link, X is carbonyl, R.sup.2 is hydrogen or chloro, cyano, nitro, methyl, allyl, methoxy or allyloxy in the ortho-position of the benzene ring and R.sup.3 and R.sup.4 are both hydrogen; or the acid-addition salts thereof.
- 3. A composition as claimed in claim 1 wherein A is ethylene, 1-methylethylene or 1,1-dimethylethylene, R.sup.1 is phenyl, R.sup.12 is hydrogen, chloro, nitro, hydroxy, methyl or methoxy, R.sup.13 and R.sup.14 are both hydrogen, Y is methylene, ethylene or methyleneoxy, X is carbonyl, R.sup.2 is hydrogen or chloro, cyano, nitro, methyl, allyl, methoxy or allyloxy in the ortho- or meta- position of the benzene ring and R.sup.3 and R.sup.4 are both hydrogen; or the acid-addition salts thereof
- 4. A composition as claimed in claim 1 wherein A is ethylene, 1-methylethylene or 1,1-dimethylethylene, R.sup.1 is hydrogen or alkyl of up to 6 carbon atoms, Y is methyleneoxy, X is carbonyl, and R.sup.2 is hydrogen or chloro, cyano, nitro, methyl, allyl, methoxy or allyloxy in the ortho-position of the benzene ring and R.sup.3 and R.sup.4 are both hydrogen; or the acid-addition salts thereof.
- 5. A composition as claimed in claim 1 wherein A is ethylene, 1-methylethylene or 1,1-dimethylethylene, R.sup.1 is alkyl or cycloalkyl each of up to 6 carbon atoms or phenyl, R.sup.12 is hydrogen, methyl, methoxy or phenyl, R.sup.13 and R.sup.14 are both hydrogen, Y is a direct link or methylene, X is carbonyl, R.sup.2 is hydrogen or hydroxy, R.sup.3 is hydrogen and R.sup.4 is hydroxy; and the acid-addition salts thereof.
- 6. A composition as claimed in claim 1 wherein A is ethylene, 1-methylethylene or 1,1-dimethylethylene, R.sup.1 is alkyl of up to 6 carbon atoms, Y is oxygen or methyleneoxy, X is carbonyl, and R.sup.2 is hydrogen or hydroxy, R.sup.3 is hydrogen and R.sup.4 is hydroxy or the acid-addition salts thereof.
- 7. A composition as claimed in claim 1 wherein the active ingredient is selected from the group consisting of
- 1-phenoxy-3-.beta.-benzamidoethylamino-2-propanol;
- 1-phenoxy-3-.beta.-phenylacetamidoethylamino-2-propanol;
- 1-phenoxy-3-.beta.-phenoxyacetamidoethylamino-2-propanol;
- 1-phenoxy-3-(.alpha.-methyl-.beta.-phenylacetamidoethyl)amino-2-propanol;
- 1-phenoxy-3-.beta.-pivalamidoethylamino-2-propanol;
- 1-phenoxy-3-(.beta.-isobutyramido-.alpha.-methylethyl) amino-2-propanol;
- 1-(2-nitrophenoxy)-3-.beta.-isobutyramidoethylamino-2-propanol;
- 1-phenoxy-3-.beta.-propionamidoethylamino-2-propanol;
- 1-phenoxy-3-.beta.-hydroxyacetamidoethylamino-2-propanol;
- 1-(2-cyanophenoxy)-3-.beta.-propionamidoethylamino-2-propanol;
- 1-phenoxy-3-.beta.-(2-chlorophenylacetamidoethyl)amino-2-propanol;
- 1-phenoxy-3-.beta.-butyramidoethylamino-2-propanol;
- 1-phenoxy-3-.beta.-isobutyramidoethylamino-2-propanol;
- 1-phenoxy-3-.beta.-(4-methoxyphenylacetamidoethyl)amino-2-propanol;
- 1-phenoxy-3-.beta.-acetamidoethylamino-2-propanol;
- 1-(2-methoxyphenoxy)-3-.beta.-isobutyramidoethylamino-2-propanol;
- 1-phenoxy-3-(.alpha.,.alpha.-dimethyl-.beta.-isobutyramidoethyl) amino-2-propanol;
- 1-phenoxy-3-(.alpha.,.alpha.-dimethyl-.beta.-phenylacetamidoethyl) amino-2-propanol; and the acid-addition salts thereof.
- 8. A composition as claimed in claim 1 wherein the active ingredient is selected from the group consisting of 1-(3,4-dihydroxyphenoxy)-3-.beta.-isobutyramidoethylamino-2-propanol and the acid-addition salts thereof.
- 9. A composition as claimed in claim 1 wherein the active ingredient is selected from the group consisting of 1-(2-cyanophenoxy)-3-.beta.-(4-hydroxyphenylacetamido) ethylamino-2-propanol and the acid-addition salt thereof.
- 10. A composition as claimed in claim 1 wherein the acid-addition salt is a hydrochloride, hydrobromide, phosphate, sulphate, oxalate, lactate, tartrate, acetate, salicylate, citrate, benzoate, .beta.-naphthoate, adipate or 1,1-methylene-bis-(2-hydroxy-3-naphthoate), or a salt derived from a sulphonated polystyrene resin.
- 11. The compound 1-(2-cyanophenoxy)-3-.beta.-(4-hydroxyphenylacetamido)ethylamino-2-propanol or an acid-addition salt thereof.
- 12. A method for the treatment or prophylaxis of heart diseases and hypertension in warm-blooded animals which comprises administering to said animals a therapeutically effective amount of at least one alkanolamine or salt thereof defined in claim 1.
- 13. A method for producing coronary .beta.-adrenergic blockade in warm-blooded animals in need of such blockade which comprises administering to said animals a therapeutically effective amount of at least one alkanolamine or salt thereof defined in claim 1.
- 14. A method for the treatment of acute or chronic heart failure in warm-blooded animals which comprises administering to said animals a therapeutically effective amount of at least one cardiac stimulant alkanolamine or salt thereof defined in claim 1 wherein one or more of the substituents R.sup.2, R.sup.3 and R.sup.4 is hydroxy.
Priority Claims (1)
Number |
Date |
Country |
Kind |
57970/72 |
Dec 1972 |
GBX |
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Parent Case Info
This application is a divisional continuation-in-part of application Ser. No. 880,495, filed Feb. 23, 1978 now U.S. Pat. No. 4,131,685 as a division of application Ser. No. 738,173, filed Nov. 2, 1976, now U.S. Pat. No. 4,083,992, which itself is a division of application Ser. No. 607,995, filed Aug. 26, 1975, now U.S. Pat. No. 4,010,189, which in turn is a division of application Ser. No. 421,669, filed Dec. 4, 1973, now U.S. Pat. No. 3,928,412.
US Referenced Citations (9)
Divisions (3)
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Number |
Date |
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738173 |
Nov 1976 |
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Parent |
607995 |
Aug 1975 |
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Parent |
421669 |
Dec 1973 |
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Continuation in Parts (1)
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880495 |
Feb 1978 |
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