US4167581A
Expired / Lapsed
US
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Alkanolamine derivatives and pharmaceutical compositions and uses thereof
Assignee: Imperial Chemical Industries Ltd
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Filing: 1978-11-01
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Granted: 1979-09-11
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Expires: 1998-11-01
Abstract
Abstract 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.
Inventors
- 👤 Leslie H. Smith
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 19:54
CPC Classifications
C; C07; C07C; C07C275/00; C07C275/28; C07C233/00; C07C271/00; C07C271/06; C07C271/08; C07C271/10; C07C271/20; C07C275/04; C07C275/06; C07C275/14
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
234 words
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 1 is hydrogen, or alkyl, halogenoalkyl, alkenyl or cycloalkyl each of up to 10 carbon atoms, or aryl of the formula: ##STR21## wherein R 2 , R 3 , R 12 and R 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 2 and R 3 together, and/or R 12 and R 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 4 is hydrogen, hydroxy or hydroxymethyl or aralkoxy of up to 12 carbon atoms; wherein R 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 1 is hydrogen, oxygen; and the acid-addition salts thereof, in association with a pharmaceutically-acceptable diluent or carrier therefor.
Claim 2
Dependent Claim
234 words
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 1 is hydrogen, or alkyl, halogenoalkyl, alkenyl or cycloalkyl each of up to 10 carbon atoms, or aryl of the formula: ##STR21## wherein R 2 , R 3 , R 12 and R 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 2 and R 3 together, and/or R 12 and R 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 4 is hydrogen, hydroxy or hydroxymethyl or aralkoxy of up to 12 carbon atoms; wherein R 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 1 is hydrogen, oxygen; and the acid-addition salts thereof, in association with a pharmaceutically-acceptable diluent or carrier therefor.
Claim 3
Dependent Claim
77 words
A composition as claimed in claim 1 wherein A is ethylene, 1-methylethylene or 1,1-dimethylethylene, R 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 2 is hydrogen or chloro, cyano, nitro, methyl, allyl, methoxy or allyloxy in the ortho-position of the benzene ring and R 3 and R 4 are both hydrogen; or the acid-addition salts thereof.
Claim 4
Dependent Claim
82 words
A composition as claimed in claim 1 wherein A is ethylene, 1-methylethylene or 1,1-dimethylethylene, R 1 is phenyl, R 12 is hydrogen, chloro, nitro, hydroxy, methyl or methoxy, R 13 and R 14 are both hydrogen, Y is methylene, ethylene or methyleneoxy, X is carbonyl, R 2 is hydrogen or chloro, cyano, nitro, methyl, allyl, methoxy or allyloxy in the ortho- or meta- position of the benzene ring and R 3 and R 4 are both hydrogen; or the acid-addition salts thereof
Claim 5
Dependent Claim
67 words
A composition as claimed in claim 1 wherein A is ethylene, 1-methylethylene or 1,1-dimethylethylene, R 1 is hydrogen or alkyl of up to 6 carbon atoms, Y is methyleneoxy, X is carbonyl, and R 2 is hydrogen or chloro, cyano, nitro, methyl, allyl, methoxy or allyloxy in the ortho-position of the benzene ring and R 3 and R 4 are both hydrogen; or the acid-addition salts thereof.
Claim 6
Dependent Claim
75 words
A composition as claimed in claim 1 wherein A is ethylene, 1-methylethylene or 1,1-dimethylethylene, R 1 is alkyl or cycloalkyl each of up to 6 carbon atoms or phenyl, R 12 is hydrogen, methyl, methoxy or phenyl, R 13 and R 14 are both hydrogen, Y is a direct link or methylene, X is carbonyl, R 2 is hydrogen or hydroxy, R 3 is hydrogen and R 4 is hydroxy; and the acid-addition salts thereof.
Claim 7
Dependent Claim
53 words
A composition as claimed in claim 1 wherein A is ethylene, 1-methylethylene or 1,1-dimethylethylene, R 1 is alkyl of up to 6 carbon atoms, Y is oxygen or methyleneoxy, X is carbonyl, and R 2 is hydrogen or hydroxy, R 3 is hydrogen and R 4 is hydroxy or the acid-addition salts thereof.
Claim 8
Dependent Claim
44 words
A composition as claimed in claim 1 wherein the active ingredient is selected from the group consisting of 1-phenoxy-3-β-benzamidoethylamino-2-propanol; 1-phenoxy-3-β-phenylacetamidoethylamino-2-propanol; 1-phenoxy-3-β-phenoxyacetamidoethylamino-2-propanol; 1-phenoxy-3-(α-methyl-β-phenylacetamidoethyl)amino-2-propanol; 1-phenoxy-3-β-pivalamidoethylamino-2-propanol; 1-phenoxy-3-(β-isobutyramido-α-methylethyl) amino-2-propanol; 1-(2-nitrophenoxy)-3-β-isobutyramidoethylamino-2-propanol; 1-phenoxy-3-β-propionamidoethylamino-2-propanol; 1-phenoxy-3-β-hydroxyacetamidoethylamino-2-propanol; 1-(2-cyanophenoxy)-3-β-propionamidoethylamino-2-propanol; 1-phenoxy-3-β-(2-chlorophenylacetamidoethyl)amino-2-propanol; 1-phenoxy-3-β-butyramidoethylamino-2-propanol; 1-phenoxy-3-β-isobutyramidoethylamino-2-propanol; 1-phenoxy-3-β-(4-methoxyphenylacetamidoethyl)amino-2-propanol; 1-phenoxy-3-β-acetamidoethylamino-2-propanol; 1-(2-methoxyphenoxy)-3-β-isobutyramidoethylamino-2-propanol; 1-phenoxy-3-(α,α-dimethyl-β-isobutyramidoethyl) amino-2-propanol; 1-phenoxy-3-(α,α-dimethyl-β-phenylacetamidoethyl) amino-2-propanol; and the acid-addition salts thereof.
Claim 9
Dependent Claim
24 words
A composition as claimed in claim 1 wherein the active ingredient is selected from the group consisting of 1-(3,4-dihydroxyphenoxy)-3-β-isobutyramidoethylamino-2-propanol and the acid-addition salts thereof.
Claim 10
Dependent Claim
25 words
A composition as claimed in claim 1 wherein the active ingredient is selected from the group consisting of 1-(2-cyanophenoxy)-3-β-(4-hydroxyphenylacetamido) ethylamino-2-propanol and the acid-addition salt thereof.
Claim 11
Dependent Claim
37 words
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, β-naphthoate, adipate or 1,1-methylene-bis-(2-hydroxy-3-naphthoate), or a salt derived from a sulphonated polystyrene resin.
Claim 12
Dependent Claim
8 words
The compound 1-(2-cyanophenoxy)-3-β-(4-hydroxyphenylacetamido)ethylamino-2-propanol or an acid-addition salt thereof.
Claim 13
Dependent Claim
8 words
The compound 1-(2-cyanophenoxy)-3-β-(4-hydroxyphenylacetamido)ethylamino-2-propanol or an acid-addition salt thereof.
Claim 14
Dependent Claim
37 words
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.
Claim 15
Dependent Claim
37 words
A method for producing coronary β-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.
Claim 16
Dependent Claim
55 words
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 2 , R 3 and R 4 is hydroxy.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-09-10 | 1983-03-12 | 1983-09-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-09-10 | 1987-03-12 | 1987-09-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-09-10 | 1991-03-12 | 1991-09-11 | $7700.00 | Window Closed / Lapsed |