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Beta-blocking oxindole derivatives

Assignee: Roche Diagnostics GmbH
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Filing: 1986-12-30
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Granted: 1989-05-02
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Expires: 2006-12-30
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Abstract

Abstract The present invention provides oxindole derivatives of the formula: ##STR1## wherein the various substituents are defined hereinbelow. The above compounds display nitrate-like as well as β-blocking actions.

Inventors

  • 👤 Helmut Michel
  • 👤 Wolfgang Kampe
  • 👤 Klaus Strein
  • 👤 Wolfgang Bartsch

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 18:52
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/06; A; A61; A61P; A61P25/00; A61P25/02; A61P9/00; A61P9/08; A61P9/10; C07D209/00; C07D209/02; C07D209/04; C07D209/30; C07D209/32; C07D209/34; C07D403/00; C07D403/02; C07D403/06; C07D405/00; C07D405/02; C07D405/06; C07D405/12; C07D409/00; C07D409/02; C07D409/06

Claims Analysis

Total Claims: 14
Claim 1
Independent Claim 254 words
An oxindole compound of the formula: ##STR14## wherein R 1 is a C 2 -C 10 -nitratoalkyl, X is hydrogen or C 1 -C 6 -alkyl; Y, together with X and the carbon atom to which they are attached, forms a C 3 -C 7 cycloalkyl ring, or is a group of the formula: ##STR15## wherein R 2 is hydrogen or R 2 together with X represents a valency bond, R 3 is hydrogen or a straight-chained or branched C 1 -C 6 -alkyl and R 4 is straight-chained or branched C 1 -C 6 -alkyl, C 3 -C 6 cycloalkyl; or phenyl, furan, thiophene, pyrrole, pyrazole, imidazole, triazole, tetrazole, imidazolinone, pyridine, pyrimidine, uracil, indole, indazole and dihydropyran radical which is unsubstituted or substituted by halogen, C 1 -C 6 -alkyl, hydroxyalkyl, hydroxyl, C 1 -C 6 -alkoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyloxy, C 2 -C 4 -alkynyl, amino, C 1 -C 4 -alkylamino, C 2 -C 8 -dialkylamino, aminocarbonyl, C 1 -C 4 -alkylaminocarbonyl, C 2 -C 8 -dialkylaminocarbonyl, cyano, C 2 -C 4 -alkanoyl, aminosulphonyl, C 1 -C 4 -alkylaminosulphonyl, C 2 -C 8 -dialkylaminosulphonyl, carboxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 2 -C 4 -alkanoylamido, C 1 -C 4 -alkylsulphonylamido or nitro groups or a C 1 -C 2 -alkylenedioxy radical or R 3 and R 4 together with the C-atom represent pyrrolidine or piperidine; or a pharmacologically acceptable salt thereof.
Claim 2
Dependent Claim 254 words
An oxindole compound of the formula: ##STR14## wherein R 1 is a C 2 -C 10 -nitratoalkyl, X is hydrogen or C 1 -C 6 -alkyl; Y, together with X and the carbon atom to which they are attached, forms a C 3 -C 7 cycloalkyl ring, or is a group of the formula: ##STR15## wherein R 2 is hydrogen or R 2 together with X represents a valency bond, R 3 is hydrogen or a straight-chained or branched C 1 -C 6 -alkyl and R 4 is straight-chained or branched C 1 -C 6 -alkyl, C 3 -C 6 cycloalkyl; or phenyl, furan, thiophene, pyrrole, pyrazole, imidazole, triazole, tetrazole, imidazolinone, pyridine, pyrimidine, uracil, indole, indazole and dihydropyran radical which is unsubstituted or substituted by halogen, C 1 -C 6 -alkyl, hydroxyalkyl, hydroxyl, C 1 -C 6 -alkoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyloxy, C 2 -C 4 -alkynyl, amino, C 1 -C 4 -alkylamino, C 2 -C 8 -dialkylamino, aminocarbonyl, C 1 -C 4 -alkylaminocarbonyl, C 2 -C 8 -dialkylaminocarbonyl, cyano, C 2 -C 4 -alkanoyl, aminosulphonyl, C 1 -C 4 -alkylaminosulphonyl, C 2 -C 8 -dialkylaminosulphonyl, carboxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 2 -C 4 -alkanoylamido, C 1 -C 4 -alkylsulphonylamido or nitro groups or a C 1 -C 2 -alkylenedioxy radical or R 3 and R 4 together with the C-atom represent pyrrolidine or piperidine; or a pharmacologically acceptable salt thereof.
Claim 3
Dependent Claim 26 words
The compound of claim 1 wherein R 1 is selected from the group consisting of nitratoethyl, nitratopropyl, nitratobutyl, nitratopentyl, nitroatohexyl, 1-methyl-2-nitratoethyl 1-methyl-3-nitratopropyl, 1,1-dimethyl-3,-nitratopropyl, 1,3-dimethyl-3-nitratopropyl or 2,2-dimethyl-3-nitratopropyl.
Claim 4
Dependent Claim 38 words
The compound of claim 1 wherein the C 1 -C 6 -alkyl in the substituents R 3 , R 4 , R 5 , X are individually selected from the group consisting of methyl, ethyl, isopropyl, and tert.-butyl.
Claim 5
Dependent Claim 120 words
The compound of claim 1 wherein R 4 is phenyl or phenyl substituted by halogen, C 1 -C 6 -alkyl, hydroxyalkyl, hydroxyl, C 1 -C 6 -alkoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyloxy, C 2 -C 4 -alkynyl, amino, C 1 -C 4 -alkylamino, C 2 -C 8 -dialkylamino, aminocarbonyl, C 1 -C 4 -alkylaminocarbonyl, C 2 -C 8 -dialkylaminocarbonyl, cyano, C 2 -C 4 -alkanoyl, aminosulphonyl, C 1 -C 4 -alkylaminosulphonyl, C 2 -C 8 -dialkylaminosulphonyl, carboxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 2 -C 4 -alkanoylamido, C 1 -C 4 -alkylsulphonylamido, C 1 -C 2 -alkylenedioxy or nitro groups.
Claim 6
Dependent Claim 60 words
The compound of claim 1 wherein R 3 is hydrogen or methyl and R 4 is phenyl, pyrazole, pyrrole, furan, thiophene, triazole, pyridine or uracil, which is unsubstituted or substituted by C 1 -C 6 -alkyl, cyano, nitro, halogen or C 1 -C 6 alkoxy or R 3 and R 4 together with the carbon atom represent pyrrolidine or piperidine.
Claim 7
Dependent Claim 7 words
The compound of claim 1 designated 4-[2-hydroxy-3-(1-methyl-3-nitratopropylamino)-propoxy]-3-benzylideneindolinone.
Claim 8
Dependent Claim 7 words
The compound of claim 1 designated 4-[2-hydroxy-3-(1-methyl-3-nitratopropylamino)-propoxy]-3-(pyrazol-5-yl)-methyleneindolinone.
Claim 9
Dependent Claim 7 words
The compound of claim 1 designated 4-[2-hydroxy-3-(1-methyl-3-nitratopropylamino)propoxy]-3-(3-methyl-pyrazole-5-yl)methylene-indolinone.
Claim 10
Dependent Claim 7 words
The compound of claim 1 designated 4-[2-hydroxy-3-(1,1-dimethyl-3-nitratopropylamino)-propoxy]-3-(pyrazol-5-yl)-methyleneindolinone.
Claim 11
Dependent Claim 7 words
The compound of claim 1 designated 4-[2-hydroxy-3-(1-methyl-3-nitratopropylamino)-propoxy]-3-(pyridin-2-yl)-methyleneindolinone.
Claim 12
Dependent Claim 7 words
The compound of claim 1 designated 4-[2-hydroxy-3-(1-methyl-3-nitratopropylamino)propoxy]-3-(4-nitro-benzylidene)indolinone.
Claim 13
Dependent Claim 37 words
The compound of claim 1 wherein C 3 -C 7 cycloalkyl rings formed by X and Y and the carbon to which they are attached are selected from the group consisting of cyclopropyl, cyclopentyl, cyclohexyl and cycloheptyl.
Claim 14
Dependent Claim 57 words
A pharmaceutical composition for the treatment of heart and circulatory diseases that respond to a lowering of blood pressure, a positive inotropic action, an improvement in microcirculation or a combination thereof, comprising an effective amount, for the treatment and prophylaxis of such heart and circulatory diseases, of the compound of claim 1 in a pharmaceutically acceptable carrier.

References Cited (Backward Citations)

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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) 1992-05-01 1992-10-31 1993-05-02 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1996-05-01 1996-10-31 1997-05-02 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2000-05-01 2000-10-31 2001-05-02 $7700.00 Window Closed / Lapsed

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