US4479962A
Expired / Lapsed
US
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Indazoloxypropanolamine derivatives and use in combating, and for the prophylaxis of, cardiac and circulatory diseases
Assignee: Roche Diagnostics GmbH
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Filing: 1982-08-02
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Granted: 1984-10-30
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Expires: 2002-08-02
Abstract
Abstract The present invention provides heteroaryloxypropanolamines and pharmaceutical compositions containing them, for combating, and for the prophylaxis of, cardiac and circulatory diseases. The heteroaryloxypropanolamines of the present invention are of the general formula: <IMAGE> wherein A is a bi- or tricyclic heteroaromatic radical, which is optionally partly hydrogenated, X is a straight-chained or branched alkylene chain containing 2 to 6 carbon atoms, R1 and R2, which can be the same or different, are hydrogen atoms or lower alkyl or benzyl radicals, R3, R4 and R5, which can be the same or different, are hydrogen atoms or lower alkyl, benzyl, formyl, lower alkanoyl, cyano, hydroxymethyl, lower alkoxycarbonyl or carbamoyl radicals or the divalent substituents sulfur or oxygen and R6, R7 and R8, which can be the same or different, are hydrogen or halogen atoms, lower alkyl, nitro, amino, lower alkylthio or lower alkoxy radicals or R6 and R7 together represent an optionally unsaturated trimethylene chain; and the pharmacologically acceptable salts thereof. The present invention also provides processes for the preparation of these compounds, as well as pharmaceutical compositions containing them.
Inventors
- 👤 Fritz Wiedemann
- 👤 Helmut Michel
- 👤 Wolfgang Weckerle
- 👤 Egon Roesch
- 👤 Klaus Strein
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 11:47
CPC Classifications
C; C07; C07D; C07D285/00; C07D285/01; C07D285/02; C07D285/14; A; A61; A61P; A61P9/00; A61P9/04; C07D209/00; C07D209/02; C07D209/04; C07D209/08; C07D209/56; C07D209/80; C07D209/82; C07D209/88; C07D231/00; C07D231/54; C07D231/56; C07D235/00; C07D235/02; C07D235/04; C07D235/06; C07D235/08; C07D235/24; C07D235/26; C07D241/00; C07D241/36; C07D241/38; C07D241/40; C07D241/42; C07D249/00; C07D249/16; C07D249/18
Claims Analysis
Total Claims: 33
Claim 1
Independent Claim
140 words
Indazoloxypropanolamine of the formula: ##STR10## wherein A is indazole, or partly hydrogenated indazole X is a straight-chained or branched alkylene chain containing 2 to 6 carbon atoms, R 1 and R 2 , which can be the same or different, are hydrogen atoms or lower alkyl or benzyl radicals, R 3 , R 4 and R 5 , which can be the same or different, are hydrogen atoms or lower alkyl, benzyl, formyl, lower alkanoyl, cyano, hydroxymethyl, lower alkoxycarbonyl or carbamoyl radicals or the divalent substituents sulfur or oxygen and R 6 , R 7 and R 8 , which can be the same or different, are hydrogen or halogen atoms, lower alkyl, nitro, amino, lower alkylthio or lower alkoxy radicals or R 6 and R 7 together represent an optionally unsaturated trimethylene chain; and the pharmacologically acceptable salts thereof.
Claim 2
Dependent Claim
140 words
Indazoloxypropanolamine of the formula: ##STR10## wherein A is indazole, or partly hydrogenated indazole X is a straight-chained or branched alkylene chain containing 2 to 6 carbon atoms, R 1 and R 2 , which can be the same or different, are hydrogen atoms or lower alkyl or benzyl radicals, R 3 , R 4 and R 5 , which can be the same or different, are hydrogen atoms or lower alkyl, benzyl, formyl, lower alkanoyl, cyano, hydroxymethyl, lower alkoxycarbonyl or carbamoyl radicals or the divalent substituents sulfur or oxygen and R 6 , R 7 and R 8 , which can be the same or different, are hydrogen or halogen atoms, lower alkyl, nitro, amino, lower alkylthio or lower alkoxy radicals or R 6 and R 7 together represent an optionally unsaturated trimethylene chain; and the pharmacologically acceptable salts thereof.
Claim 3
Dependent Claim
11 words
Indazoloxypropanolamine compound as claimed in claim 1, wherein A is indazole.
Claim 4
Dependent Claim
12 words
Indazoloxypropanolamine compound as claimed in claim 1, wherein A is partly hydrogenated.
Claim 5
Dependent Claim
16 words
Indazoloxypropanolamine compound as claimed in claim 1, wherein R 1 and R 2 are both hydrogen.
Claim 6
Dependent Claim
17 words
Indazoloxypropanolamine compound as claimed in claim 1, wherein one of R 1 and R 2 are alkyl.
Claim 7
Dependent Claim
17 words
Indazoloxypropanolamine compound as claimed in claim 1, wherein one of R 1 and R 2 are benzyl.
Claim 8
Dependent Claim
20 words
Indazoloxypropanolamine compound as claimed in claim 1, wherein R 3 , R 4 , and R 5 are all hydrogen.
Claim 9
Dependent Claim
21 words
Indazoloxypropanolamine compound as claimed in claim 1, wherein one of R 3 , R 4 and R 5 is lower alkyl.
Claim 10
Dependent Claim
20 words
Indazoloxypropanolamine compound as claimed in claim 1, wherein one of R 3 , R 4 and R 5 is benzyl.
Claim 11
Dependent Claim
20 words
Indazoloxypropanolamine compound as claimed in claim 1, wherein one of R 3 , R 4 and R 5 is formyl.
Claim 12
Dependent Claim
21 words
Indazoloxypropanolamine compound as claimed in claim 1, wherein one of R 3 , R 4 and R 5 is lower alkanoyl.
Claim 13
Dependent Claim
20 words
Indazoloxypropanolamine compound as claimed in claim 1, wherein one of R 3 , R 4 and R 5 is cyano.
Claim 14
Dependent Claim
20 words
Indazoloxypropanolamine compound as claimed in claim 1, wherein one of R 3 , R 4 and R 5 is hydroxymethyl.
Claim 15
Dependent Claim
21 words
Indazoloxypropanolamine compound as claimed in claim 1, wherein one of R 3 , R 4 and R 5 is lower alkoxycarbonyl.
Claim 16
Dependent Claim
20 words
Indazoloxypropanolamine compound as claimed in claim 1, wherein one of R 3 , R 4 and R 5 is carbamoyl.
Claim 17
Dependent Claim
22 words
Indazoloxypropanolamine compound as claimed in claim 1, wherein at least one of R 3 , R 4 and R 5 is sulfur.
Claim 18
Dependent Claim
22 words
Indazoloxypropanolamine compound as claimed in claim 1, wherein at least one of R 3 , R 4 and R 5 is oxygen.
Claim 19
Dependent Claim
19 words
Indazoloxypropanolamine compound as claimed in claim 1, wherein R 6 , R 7 and R 8 are all hydrogen.
Claim 20
Dependent Claim
22 words
Indazoloxypropanolamine compound as claimed in claim 1, wherein at least one of R 6 , R 7 and R 8 is halogen.
Claim 21
Dependent Claim
23 words
Indazoloxypropanolamine compound as claimed in claim 1, wherein at least one of R 6 , R 7 and R 8 is lower alkyl.
Claim 22
Dependent Claim
22 words
Indazoloxypropanolamine compound as claimed in claim 1, wherein at least one of R 6 , R 7 and R 8 is nitro.
Claim 23
Dependent Claim
22 words
Indazoloxypropanolamine compound as claimed in claim 1, wherein at least one of R 6 , R 7 and R 8 is amino.
Claim 24
Dependent Claim
23 words
Indazoloxypropanolamine compound as claimed in claim 1, wherein at least one of R 6 , R 7 and R 8 is lower alkylthio.
Claim 25
Dependent Claim
23 words
Indazoloxypropanolamine compound as claimed in claim 1, wherein at least one of R 6 , R 7 and R 8 is lower alkoxy.
Claim 26
Dependent Claim
20 words
Indazoloxypropanolamine compound as claimed in claim 1, wherein R 6 and R 7 together represent an optionally unsaturated trimethylene chain.
Claim 27
Dependent Claim
9 words
Indazoloxypropanolamine compound as claimed in claim 1 designated 1-(indazol-4-yloxy)-3-[2-(2,6-dimethylphenylamino)-ethylamine]-propan-2-ol
Claim 28
Dependent Claim
9 words
Indazoloxypropanolamine compound as claimed in claim 1 designated 1-(indazol-4-yloxy)-3-[2-(3-nitrophenylamino)-ethyl-amino]-propan-2-ol.
Claim 29
Dependent Claim
9 words
Indazoloxypropanolamine compound as claimed in claim 1 designated 1-(indazol-4-yloxy)-3-[3-(2,6-dimethylphenylamino)-propylamino]-propan-3-ol.
Claim 30
Dependent Claim
9 words
Indazoloxypropanolamine compound as claimed in claim 1 designated 1-(indazol-4-yloxy)-3-[2-(indanyl-4-amino)-ethylamino]-propan-2-ol.
Claim 31
Dependent Claim
36 words
Composition for combating those cardiac and circulatory disorders which can be ameliorated by a cardiotonic agent comprising an effective cardiotonic amount of an indazoloxypropanolamine compound as claimed in claim 1, together with a pharmacologically acceptable carrier.
Claim 32
Dependent Claim
35 words
Method of combatting those cardiac and circulatory disorders which can be ameliorated by a cardiotonic agent comprising administering to an afflicted subject an effective cardiotonic amount of an indazoloxypropanolamine compound as claimed in claim 1.
Claim 33
Dependent Claim
23 words
Method as claimed in claim 28, wherein the compound is at least one of: 1-(indazol-4-yloxy)-3-[2-(2,6-dimethylphenylamino)ethylamino]-propan-2-ol; 1-(indazol-4-yloxy)-3-[2-(3-nitrophenylamino)-ethylamino]-propan-2-ol; 1-(indazol-4-yloxy)-3-[3-(2,6-dimethylphenylamino)propylamino]-propan-3-ol; 1-(indazol-4-yloxy)-3-[2-(indanyl-4-amino)-ethylamino]-propan-2-ol; or pharmacologically compatible salt thereof.
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) | 1987-10-30 | 1988-04-30 | 1988-10-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-10-30 | 1992-04-30 | 1992-10-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-10-30 | 1996-04-30 | 1996-10-30 | $7700.00 | Window Closed / Lapsed |