Claims
- 1. An alkanolamine selected from compounds of the formula: ##STR6## 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: ##STR7## 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, 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; and wherein when R.sup.1 is hydrogen, alkyl, halogenoalkyl or alkenyl, Y is alkyleneoxy or alkylenecarbonyloxy each of up to 6 carbon atoms and when R.sup.1 is cycloalkyl or aryl Y is alkylene, alkyleneoxy or alkylenecarbonyloxy each of up to 6 carbon atoms; and the acid-addition salts thereof.
- 2. An alkanolamine as claimed in claim 1 selected from compounds of the formula given in claim 1 wherein A is ethylene, trimethylene, tetramethylene, hexamethylene, dodecamethylene, 1-methylethylene, 2-methylethylene or 1,1-dimethylethylene; wherein R.sup.1 is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, n-octyl, trifluoromethyl, allyl, cyclopropyl, cyclopentyl or cyclohexyl, or aryl of the formula: ##STR8## wherein R.sup.2, R.sup.3, R.sup.12 and R.sup.13, which may be the same or different, each is hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, amino, nitro, cyano, methyl, ethyl, n-propyl, cyclopropyl, cyclopentyl, allyl, ethynyl, methoxy, isopropoxy, methylthio, cyclopentyloxy, allyloxy, propargyloxy, formyl, acetyl, phenyl, phenoxy or benzyloxy, 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; wherein R.sup.4 is hydrogen, hydroxy, hydroxymethyl or benzyloxy; wherein R.sup.14 is hydrogen, amino or dimethylamino; and wherein when R.sup.1 is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, n-octyl, trifluoromethyl or allyl, Y is methyleneoxy, ethyleneoxy, 2,2-dimethylethyleneoxy or ethylenecarbonyloxy; and when R.sup.1 is cyclopropyl, cyclopentyl, cyclohexyl or aryl, Y is methylene, ethylidene, methyleneoxy, ethyleneoxy, 2,2-dimethyl ethyleneoxy or ethylenecarbonyloxy; and the acid-addition salts thereof.
- 3. An alkanolamine as claimed in claim 1 selected from compounds of the formula given 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 alkyleneoxy or alkylenecarbonyloxy each of up to 4 carbon atoms, R.sup.2 is hydrogen, fluoro, chloro, cyano or methyl and R.sup.3 and R.sup.4 are both hydrogen; and the acid-addition salts thereof.
- 4. An alkanolamine as claimed in claim 3 wherein A is ethylene and R.sup.2 is fluoro, chloro, cyano or methyl in the 2-position of the benzene nucleus.
- 5. An alkanolamine as claimed in claim 1 selected from compounds of the formula given in claim 1 wherein A is ethylene, 1-methylethylene or 1,1-dimethylethylene, R.sup.1 is unsubstituted phenyl, Y is alkylene of 1 or 2 carbon atoms, R.sup.2 is hydrogen, fluoro, chloro, cyano or methyl and R.sup.3 and R.sup.4 are both hydrogen; and the acid-addition salts thereof.
- 6. An alkanolamine as claimed in claim 5 wherein A is ethylene, Y is methylene and R.sup.2 is fluoro, chloro, cyano or methyl in the 2-position of the benzene nucleus.
- 7. An alkanolamine as claimed in claim 1 selected from compounds of the formula given in claim 1 wherein A is ethylene, 1-methyethylene or 1,1-dimethylethylene, R.sup.1 is hydrogen or alkyl of up to 6 carbon atoms and Y is alkyleneoxy or alkylenecarbonyloxy each of up to 4 carbon atoms, or R.sup.1 is unsubstituted phenyl and Y is alkylene of 1 or 2 carbon atoms, R.sup.4 is hydroxy and R.sup.2 and R.sup.3 are both hydrogen; and the acid-addition salts thereof.
- 8. An alkanolamine as claimed in claim 7 wherein A is ethylene and R.sup.4 is hydroxy in the 4-position of the benzene nucleus.
- 9. An alkanolamine as claimed in claim 1 selected from:
- 1-(2-cyanophenoxy)-3-.beta.-(3-benzylureido)ethylamino-2-propanol;
- 1-phenoxy-3-.beta.-(3-.beta.-hydroxymethylureido)ethylamino-2-propanol;
- 1-(2-fluorophenoxy)-3-.beta.-(3-benzylureido)ethylamino-2-propanol; and
- 1-(2-cyanophenoxy)-3-.beta.-(3-methoxymethylureido)ethylamino-2-propanol;
- and the acid-addition salts thereof.
- 10. An alkanolamine as claimed in claim 1 selected from
- 1-(4-hydroxyphenoxy)-3-.beta.-(3-methoxymethylureido)ethylamino-2-propanol; and
- 1-(4-hydroxyphenoxy)-3-.beta.-(3-n-butyloxycarbonylmethylureido) ethylamino-2-propanol;
- and the acid-addition salts thereof.
- 11. An acid-addition salt as claimed in claim 1 which 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.
- 12. A pharmaceutical composition comprising as active ingredient at least one alkanolamine or an acid-addition salt thereof, claimed in claim 1, in association with a pharmaceutically-acceptable diluent or carrier therefor.
- 13. A method for the treatment or prophylaxis of heart diseases and hypertension in a warm-blooded animal which comprises administering to said animal an effective amount of at least one compound claimed in claim 1.
- 14. A method for producing coronary .beta.-adrenergic blockage in a warm-blooded animal in need of such blockade which comprises administering to said animal an effective amount of at least one compound claimed in claim 1.
- 15. A method for the treatment of acute or chronic heart failure in a warm-blooded animal which comprises administering to said animal an effective amount of at least one cardiac stimulant alkanolamine, claimed in claim 1, which has the formula given in claim 1 wherein one or more of the substituents R.sup.2, R.sup.3 and R.sup.4 is hydrogen and the other substituents are as defined in claim 1.
Priority Claims (2)
Number |
Date |
Country |
Kind |
57970/72 |
Dec 1972 |
GBX |
|
43478/73 |
Sep 1973 |
GBX |
|
Parent Case Info
This application is a divisional continuation-in-part of application Ser. No. 738,173, filed Nov. 2, 1976 now U.S. Pat. No. 4,083,992, which is a divisional of application Ser. No. 607,995, filed Aug. 26, 1975 now U.S. Pat. No. 4,010,189, which itself is a divisional of application Ser. No. 421,669, filed Dec. 4, 1973 now U.S. Pat. No. 3,928,412.
US Referenced Citations (4)
Divisions (3)
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Number |
Date |
Country |
Parent |
738173 |
Nov 1976 |
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Parent |
607995 |
Aug 1975 |
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Parent |
421669 |
Dec 1973 |
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