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US4438143A
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1-Aryloxy-3-alkylamino-2-propanols and pharmaceutical compositions containing them
Assignee: Boehringer Ingelheim GmbH
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Filing: 1982-09-21
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Granted: 1984-03-20
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Expires: 2002-09-21
Abstract
Abstract This invention relates to compounds of the formula <IMAGE> (I) wherein R1 represents a linear or branched alkyl of from 1 to 20 carbon atoms; R2 represents a hydrogen or halogen atom, a linear or branched alkyl or alkoxy of from 1 to 4 carbon atoms, or a divalent group -CH=CH-CH=CH- or -(CH2)n-, in which n is an integer of from 3 to 5, with the free valences bonded in the o-position relative to one another; and R3 represents a linear or branched alkyl of from 3 to 10 carbon atoms, with the provisos that R3 is not tert.butyl when R1 is ethyl or propyl and R2 is a hydrogen atom and that R3 is not isopropyl when R1 is propyl and R2 is a hydrogen atom, or a non-toxic, pharmacologically acceptable acid addition salt thereof. The compounds of Formula I are useful for treatment and prophylaxis of diseases of the coronaries, for the treatment of hypertension, and for treatment of cardiac arrhythmia, particularly tachycardia.
Inventors
- 👤 Herbert Koppe
- 👤 Werner Kummer
- 👤 Helmut Stahle
- 👤 Gojko Muacevic
- 👤 Werner Traunecker
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 13:19
CPC Classifications
C; C07; C07C; C07C253/00; C07C253/30; C07C255/00; A; A61; A61P; A61P9/00; A61P9/08; A61P9/12
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
143 words
A compound of the formula ##STR10## wherein R 1 represents a linear or branched alkyl of from 1 to 20 carbon atoms; R 2 represents a hydrogen or halogen atom, a linear or branched alkyl or alkoxy of from 1 to 4 carbon atoms, or a divalent group --CH═CH--CH═CH-- or --(CH 2 ) n --, in which n is an integer of from 3 to 5, with the free valences bonded in the o-position relative to one another; and R 3 represents a linear or branched alkyl of from 3 to 10 carbon atoms, with the provisos that R 3 is not tert.butyl when R 1 is ethyl or propyl and R 2 is a hydrogen atom and that R 3 is not isopropyl when R 1 is propyl and R 2 is hydrogen, or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
143 words
A compound of the formula ##STR10## wherein R 1 represents a linear or branched alkyl of from 1 to 20 carbon atoms; R 2 represents a hydrogen or halogen atom, a linear or branched alkyl or alkoxy of from 1 to 4 carbon atoms, or a divalent group --CH═CH--CH═CH-- or --(CH 2 ) n --, in which n is an integer of from 3 to 5, with the free valences bonded in the o-position relative to one another; and R 3 represents a linear or branched alkyl of from 3 to 10 carbon atoms, with the provisos that R 3 is not tert.butyl when R 1 is ethyl or propyl and R 2 is a hydrogen atom and that R 3 is not isopropyl when R 1 is propyl and R 2 is hydrogen, or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
76 words
A compound of claim 1, wherein R 1 represents a linear or branched alkyl of from 1 to 7 carbon atoms; R 2 represents a hydrogen atom; and R 3 represents an alkyl branched in the α- or β-position, with the provisos that R 3 is not tert.butyl when R 1 is ethyl or propyl and that R 3 is not isopropyl when R 1 is propyl, or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 4
Dependent Claim
51 words
A compound of claim 2, wherein R 1 is selected from the group consisting of methyl, n-propyl, isopropyl, 1-ethylpropyl, n-butyl, tert.butyl, n-pentyl, neopentyl, 1-ethylpentyl, 3-ethylpentyl, and n-heptyl, and R 3 is selected from the group consisting of isopropyl, tert.butyl, sec.butyl, and tert.pentyl, or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 5
Dependent Claim
26 words
A compound of claim 2, wherein R 1 is n-pentyl and R 3 is isopropyl or tert.butyl, or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 6
Dependent Claim
17 words
The compound of claim 1 which is 1-(2-cyano-4-n-hexanoylamino-phenoxy)-3-tert.butylamino-2-propanol or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 7
Dependent Claim
17 words
The compound of claim 1 which is 1-(2-cyano-4-n-hexanoylamino-phenoxy)-3-isopropylamino-2-propanol or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 8
Dependent Claim
24 words
A β-adrenolytic pharmaceutical dosage unit composition consisting essentially of an inert pharmaceutical carrier and an effective β-adrenolytic amount of a compound of claim 1.
Claim 9
Dependent Claim
42 words
A method for the treatment or prophylaxis of diseases of the coronaries, for the treatment of hypertension, or for the treatment of cardiac arrhythmia, which comprise administering to a warm-blooded animal or human an effective amount of a compound of claim 1.
Claim 10
Dependent Claim
10 words
The method of claim 8 for the treatment of tachycardia.
References Cited (Backward Citations)
US3712927A
Cited
DE2503222A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-03-20 | 1987-09-19 | 1988-03-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-03-20 | 1991-09-19 | 1992-03-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-03-20 | 1995-09-19 | 1996-03-20 | $7700.00 | Window Closed / Lapsed |