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US4801596A Expired / Lapsed US ⏱️ 0.0 years remaining

Nitroxy amino propanols for treating heart and circulatory diseases

Assignee: Roche Diagnostics GmbH
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Filing: 1985-12-02
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Granted: 1989-01-31
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Expires: 2005-12-02
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Abstract

Abstract The present invention provides new aminopropanol derivatives of the general formula: <IMAGE> (I) wherein A is a direct bond, a straight-chained or branched alkylene chain containing up to 3 carbon atoms or a -CO-CH2- group; X is a direct bond or a carbonyl group; B is a straight-chained or branched, saturated or unsaturated alkylene chain containing up to 12 carbon atoms, in which one or two -CH2- groups can also be replaced by a saturated or unsaturated alkylene ring containing 3 to 7 carbon atoms and/or by an oxygen or sulphur atom or an -S(=O)- or -S(=O)2- group, n is 1, 2 or 3; R1 is a hydrogen atom or a straight-chained or branched, saturated or unsaturated alkyl radical containing up to 6 carbon atoms or a -B-(ONO2)n group, in which B and n have the same meanings as above, or when A is a -CO-CH2- group and X is a direct bond, R1 together with the nitrogen atom and a carbon atom of chain B can represent a heteroaliphatic ring containing 2 to 7 carbon atoms; R2 is a hydrogen or halogen atom or a cyano, hydroxyl, amino, nitro, carboxyl, carbamoyl, ureido or sulphamoyl group or an alkyl, alkoxy, alkylamino, alkylthio, hydroxyalkyl, aminoalkyl, alkoxycarbonyl, alkylcarbonyl, alkylaminocarbonyl, alkylcarbonylamino, alkoxycarbonylamino or alkylaminocarbonylamino radical; and R3 is an alkyl or nitroxyalkyl radical containing 3 to 8 carbon atoms; and the physiologically acceptable salts thereof. The present invention also provides processes for the preparation of these aminopropanol derivatives and pharmaceutical compositions containing them, as well as intermediates for the preparation of the new aminopropanol derivatives.

Inventors

  • 👤 Herbert Simon
  • 👤 Helmut Michel
  • 👤 Walter-Gunar Friebe
  • 👤 Wolfgang Bartsch

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 22:29
CPC Classifications
C; C07; C07D; C07D303/00; C07D303/02; C07D303/12; C07D303/18; C07D303/20; C07D303/22; A; A61; A61P; A61P25/00; A61P25/02; A61P9/00; A61P9/08; A61P9/10; A61P9/12; C07C; C07C255/00; C07D211/00; C07D211/04; C07D211/06; C07D211/08; C07D211/18; C07D211/20; C07D211/22; C07D211/36; C07D211/40; C07D211/44; C07D211/46; C07D405/00; C07D405/02; C07D405/12

Claims Analysis

Total Claims: 12
Claim 1
Independent Claim 170 words
A compound of the formula: ##STR21## wherein A is a direct bond, an ethylene chain or a --CO--CH 2 -- group; X is a direct bond or a carbonyl group; B is a straight-chained or branched, saturated alkyl C 1 -C 6 chain, in which one or two --CH 2 -- groups can also be replaced by a saturated C 6 cycloalkylene ring, n is 1, 2 or 3; R 1 is a hydrogen atom or a C 1 -C 4 straight-chained or branched saturated alkyl or a --B--(ONO 2 ) n group, in which B and n have the same meanings as above, or when A is a --CO--CH 2 -- group and X is a direct bond, R 1 together with the nitrogen atom and a carbon atom of chain B can represent a piperidine ring; R 2 is a hydrogen, cyano, C 1 -C 4 alkyl acetyl or ethoxycarbonyl; and R 3 is C 3 -C 5 alkyl, 2-methyl-3-butyn-2-yl or 1-nitroxy-but-3-yl or a physiologically acceptable salt thereof.
Claim 2
Dependent Claim 170 words
A compound of the formula: ##STR21## wherein A is a direct bond, an ethylene chain or a --CO--CH 2 -- group; X is a direct bond or a carbonyl group; B is a straight-chained or branched, saturated alkyl C 1 -C 6 chain, in which one or two --CH 2 -- groups can also be replaced by a saturated C 6 cycloalkylene ring, n is 1, 2 or 3; R 1 is a hydrogen atom or a C 1 -C 4 straight-chained or branched saturated alkyl or a --B--(ONO 2 ) n group, in which B and n have the same meanings as above, or when A is a --CO--CH 2 -- group and X is a direct bond, R 1 together with the nitrogen atom and a carbon atom of chain B can represent a piperidine ring; R 2 is a hydrogen, cyano, C 1 -C 4 alkyl acetyl or ethoxycarbonyl; and R 3 is C 3 -C 5 alkyl, 2-methyl-3-butyn-2-yl or 1-nitroxy-but-3-yl or a physiologically acceptable salt thereof.
Claim 3
Dependent Claim 29 words
A method for the treatment and prophylaxis of heart and circulatory diseases comprising administering 20-500 mg per day per 75 kg body weight of the compound of claim 1.
Claim 4
Dependent Claim 28 words
A pharmaceutical composition comprising an effective amount for the treatment and prophylaxis of heart and circulatory diseases of the compound of claim 1 in a pharmaceutically acceptable carrier.
Claim 5
Dependent Claim 21 words
The compound of claim 1 wherein the group ##STR22## forms with a --CH 2 -- group of B a piperidine ring.
Claim 6
Dependent Claim 16 words
The compound of claim 1 wherein R 2 is selected from hydrogen, cyano, acetyl or ethoxycarbonyl.
Claim 7
Dependent Claim 70 words
The compound of claim 1 wherein the group ##STR23## is a C 2 -C 4 -(alkylene)-carbonylamino, C 5 -C 6 -(cycloalkylene)-carbonylamino, cyclohexylenemethlcarbonylamino or ethyleneoxymethylcarbonylamino, piperidinyl or a methylenepiperidinyl group and A is a direct bond, an ethylene chain or a --CO--CH 2 --group, n is 1, 2 or 3, R 2 is a hydrogen atom or a cyano, acetyl or ethoxycarbonyl group, R 3 is isopropyl, tert-butyl, 2-methyl-3-butyn-2-yl and 1-nitroxy-but-3-yl.
Claim 8
Dependent Claim 8 words
The compound of claim 1 designated 1-[4-[(2-nitroxypropyl)-amino]-carbonylmethyl]-phenoxy-3-tert.-butylaminopropan-2-ol hemifumarate.
Claim 9
Dependent Claim 8 words
The compound of claim 1 designated 1-[4-(3-nitroxypropyl)-carbonylamino]-phenoxy-3-tert.-butylaminopropan-2-ol hydrochloride.
Claim 10
Dependent Claim 8 words
The compound of claim 1 designated 1-[4-(4-nitroxymethyl-1-piperidino)-carbonylmethyl]-phenoxy-3-tert.-butylaminopropan-2-ol fumarate.
Claim 11
Dependent Claim 8 words
The compound of claim 1 designated 1-[2-methylcarbonyl-4-(3-nitroxypropyl)-carbonylamino]-phenoxy-3-tert.-butylaminopropan-2-ol fumarate.
Claim 12
Dependent Claim 8 words
The compound of claim 1 designated 1-[2-cyano-4-(3-nitroxypropyl)-carbonylamino]-phenoxy-3-tert.-butylaminopropan-2-ol hydrochloride.

References Cited (Backward Citations)

EP0034461A1 Cited
US4438143A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1992-01-31 1992-08-01 1993-01-31 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1996-01-31 1996-08-01 1997-01-31 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2000-01-31 2000-08-01 2001-01-31 $7700.00 Window Closed / Lapsed

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