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US4034112A
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Ethanolamine derivatives having β-adrenergic blocking activity
Assignee: Imperial Chemical Industries Ltd
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Filing: 1975-12-29
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Granted: 1977-07-05
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Expires: 1995-12-29
Abstract
Abstract Novel 1-aryl-2-amidoalkylaminoethanol 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-phenyl-2-(1,1-dimethyl-2-phenylacetamidoethyl)aminoethanol.
Inventors
- 👤 Leslie Harold Smith
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 17:55
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/16; A61K31/18; C; C07; C07C; C07C233/00
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
154 words
An ethanolamine derivative selected from the group consisting of a compound of the formula: ##STR31## wherein A is alkylene of from 2 to 6 carbon atoms, wherein R 1 is hydrogen or alkyl, alkenyl, halogenoalkyl or cycloalkyl each of up to 6 carbon atoms, or aryl of the formula: ##STR32## wherein R 2 , R 3 , R 12 and R 13 , which may be the same or different, each is hydrogen, halogen, nitro, amino or cyano, or alkyl alkenyl, alkoxy, alkenyloxy, hydroxyalkyl, alkanoyl, acylamino or alkanesulphonamido each of up to 6 carbon atoms, wherein R 4 is hydrogen, hydroxy or carbamoyl, wherein R 5 is hydrogen or alkyl of up to 6 carbon atoms, wherein X is sulphonyl and wherein Y is a direct link, or alkylene or alkylenoxy each of up to 6 carbon atoms, or imino (--NH--) or (except when R 1 is hydrogen) oxygen; and an acid-addition salt thereof.
Claim 2
Dependent Claim
154 words
An ethanolamine derivative selected from the group consisting of a compound of the formula: ##STR31## wherein A is alkylene of from 2 to 6 carbon atoms, wherein R 1 is hydrogen or alkyl, alkenyl, halogenoalkyl or cycloalkyl each of up to 6 carbon atoms, or aryl of the formula: ##STR32## wherein R 2 , R 3 , R 12 and R 13 , which may be the same or different, each is hydrogen, halogen, nitro, amino or cyano, or alkyl alkenyl, alkoxy, alkenyloxy, hydroxyalkyl, alkanoyl, acylamino or alkanesulphonamido each of up to 6 carbon atoms, wherein R 4 is hydrogen, hydroxy or carbamoyl, wherein R 5 is hydrogen or alkyl of up to 6 carbon atoms, wherein X is sulphonyl and wherein Y is a direct link, or alkylene or alkylenoxy each of up to 6 carbon atoms, or imino (--NH--) or (except when R 1 is hydrogen) oxygen; and an acid-addition salt thereof.
Claim 3
Dependent Claim
65 words
An ethanolamine derivative as claimed in claim 1 selected from the group consisting of a compound of the formula given in claim 1 wherein A is ethylene, 1-methylethylene or 1,1-dimethylethylene, wherein R 1 is alkyl or cycloalkyl each of up to 6 carbon atoms, wherein R 2 and R 3 are both hydrogen, and wherein Y is a direct link, and an acid-addition salt thereof.
Claim 4
Dependent Claim
57 words
An ethanolamine derivative as claimed in claim 1 selected from the group consisting of a compound of the formula given in claim 1 wherein A is ethylene, 1-methylethylene or 1,1-dimethylethylene, wherein R 1 is phenyl, chlorophenyl or methoxyphenyl, wherein R 2 and R 3 are both hydrogen, and wherein Y is methylene, and an acid-addition salt thereof.
Claim 5
Dependent Claim
16 words
An ethanolamine derivative as claimed in claim 1 selected from 1-phenyl-2-(β-benzenesulphonamidoethyl)aminoethanol; or an acid-addition salt thereof.
Claim 6
Dependent Claim
16 words
An ethanolamine derivative as claimed in claim 1 selected from 1-phenyl-2-(β-n-propanesulphonamidoethyl)aminoethanol or an acid-addition salt thereof.
Claim 7
Dependent Claim
16 words
An ethanolamine derivative as claimed in claim 1 selected from 1-phenyl-2-(β-benzylsulphonamidoethyl)aminoethanol or an acid-addition salt thereof.
Claim 8
Dependent Claim
16 words
An ethanolamine derivative as claimed in claim 1 selected from 1-phenyl-2-(β-o-nitrobenzenesulphonamidoethyl)aminoethanol or an acid-addition salt thereof.
Claim 9
Dependent Claim
35 words
An acid-addition salt as claimed in claim 1 which 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 10
Dependent Claim
36 words
A pharmaceutical composition having β-adrenergic blocking activity, comprising as active ingredient an effective amount of at least one alkanolamine derivative or an acid-addition salt thereof, claimed in claim 1, in association with a pharmaceutically-acceptable carrier therefor.
Claim 11
Dependent Claim
36 words
A method for the treatment or prophylaxis of angina pectoris and cardiac arrhythmias and hypertension in warm-blooded animals which comprises administering to said animals an effective amount of at least one compound claimed in claim 1.
Claim 12
Dependent Claim
33 words
A method for producing coronary β-adrenergic blockade in warm-blooded animals in need of such blockade which comprises administering to said animals an effective amount of at least one compound claimed in claim 1.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-07-04 | 1981-01-03 | 1981-07-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-07-04 | 1985-01-03 | 1985-07-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-07-04 | 1989-01-03 | 1989-07-05 | $7700.00 | Window Closed / Lapsed |