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US4148895A Expired / Lapsed US ⏱️ 0.0 years remaining

Basically substituted indole derivatives

Assignee: Hoechst AG
•
Filing: 1976-12-16
•
Granted: 1979-04-10
•
Expires: 1996-12-16
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Abstract

Abstract The present invention relates to basically substituted indole derivatives and to a process for their manufacture.

Inventors

  • 👤 Rudolf Lattrell
  • 👤 Wilhelm Bartmann
  • 👤 Joachim Kaiser

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 13:30
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/04; C07D209/30; C07D209/42; A; A61; A61P; A61P9/00; A61P9/06; A61P9/12

Claims Analysis

Total Claims: 9
Claim 1
Independent Claim 235 words
A compound of the formula ##STR93## or a physiologically acceptable salt thereof wherein R 1 is piperidino, morpholino, piperazino, or piperazino substituted in the 4-position by (a) alkyl having 1 to 3 carbon atoms (b) β-hydroxyethyl (c) 2-(1,3-dioxolan-2-yl)-ethyl (d) phenyl (e) 3,4-methylene-dioxybenzyl (f) 2-furoyl (g) 3,4,5, -trimethoxybenzoyl (h) alkoxycarbonyl having up to 5 carbon atoms (i) (2-methyl-2-propenyl)-oxycarbonyl, or (j) hydroxyalkyl oxycarbonyl having 2 to 5 carbon atoms; R 2 is hydrogen, dialkylamino having identical alkyl groups each having 1 to 4 carbon atoms, piperazino substituted in the 4-position by (a) alkyl having 1 to 3 carbon atoms (b) β-hydroxyethyl (c) 2-(1,3-dioxolan-2-yl)-ethyl (d) phenyl, or (e) 3,4-methylene-dioxy-benzyl, or R 2 is pyrrolidino, piperidino, 4hydroxy-piperidino, morpholino piperazino, [N-(1-ethinyl-cyclohexyl)]-amino, [N-(4-methylpiperazino)]-amino, [N-(dialkylaminocyclohexyl]-amino wherein each alkyl has 1 to 3 carbon atoms, ##STR94## wherein A 1 is alkylene having 2 or 3 carbon atoms or such alkylene mono-substituted by hydroxy and R 12 and R 13 , taken alone, are each alkyl having 1 to 3 carbon atoms, or, taken together with the nitrogen atom to which they are attached, are morpholino, or R 2 is ##STR95## where A 2 is straight-chain alkylene having 2 or 3 carbon atoms and R 14 and R 15 taken alone, are respectively hydrogen and cyclohexyl, or, taken together with the nitrogen atom to which they are attached, are morpholino; R 3 is hydrogen or methoxy; and R 4 is methyl, phenyl, or methoxyphenyl.
Claim 2
Dependent Claim 235 words
A compound of the formula ##STR93## or a physiologically acceptable salt thereof wherein R 1 is piperidino, morpholino, piperazino, or piperazino substituted in the 4-position by (a) alkyl having 1 to 3 carbon atoms (b) β-hydroxyethyl (c) 2-(1,3-dioxolan-2-yl)-ethyl (d) phenyl (e) 3,4-methylene-dioxybenzyl (f) 2-furoyl (g) 3,4,5, -trimethoxybenzoyl (h) alkoxycarbonyl having up to 5 carbon atoms (i) (2-methyl-2-propenyl)-oxycarbonyl, or (j) hydroxyalkyl oxycarbonyl having 2 to 5 carbon atoms; R 2 is hydrogen, dialkylamino having identical alkyl groups each having 1 to 4 carbon atoms, piperazino substituted in the 4-position by (a) alkyl having 1 to 3 carbon atoms (b) β-hydroxyethyl (c) 2-(1,3-dioxolan-2-yl)-ethyl (d) phenyl, or (e) 3,4-methylene-dioxy-benzyl, or R 2 is pyrrolidino, piperidino, 4hydroxy-piperidino, morpholino piperazino, [N-(1-ethinyl-cyclohexyl)]-amino, [N-(4-methylpiperazino)]-amino, [N-(dialkylaminocyclohexyl]-amino wherein each alkyl has 1 to 3 carbon atoms, ##STR94## wherein A 1 is alkylene having 2 or 3 carbon atoms or such alkylene mono-substituted by hydroxy and R 12 and R 13 , taken alone, are each alkyl having 1 to 3 carbon atoms, or, taken together with the nitrogen atom to which they are attached, are morpholino, or R 2 is ##STR95## where A 2 is straight-chain alkylene having 2 or 3 carbon atoms and R 14 and R 15 taken alone, are respectively hydrogen and cyclohexyl, or, taken together with the nitrogen atom to which they are attached, are morpholino; R 3 is hydrogen or methoxy; and R 4 is methyl, phenyl, or methoxyphenyl.
Claim 3
Dependent Claim 49 words
A compound or salt as in claim 1 wherein R 1 is piperazino or piperazino substituted in the 4-position by alkyl having 1 to 3 carbon atoms and R 2 is piperidino, morpholino, piperazino, piperazino substituted in the 4-position by alkyl having 1 to 3 carbon atoms, or ##STR96##
Claim 4
Dependent Claim 12 words
The compound defined in claim 1 which is 1-phenyl-2-(1-piperazinyl)-indole 3-carboxylic acid (4-methyl)-piperazide.
Claim 5
Dependent Claim 12 words
The compound defined in claim 1 which is 1-phenyl-2-(1-piperazinyl)-indole 3-carboxylic acid piperazide.
Claim 6
Dependent Claim 12 words
The compound defined in claim 1 which is 2-[4-(2-(1,3-dioxolan-2-yl)-ethyl)-1-piperazinyl]-1-phenyl-indole 3-carboxylic acid (4-methyl)-piperazide.
Claim 7
Dependent Claim 11 words
The compound defined in claim 1 which is 1-phenyl-2-(1-piperazinyl)-indole 3-carboxylic acid-[4-(3,4-methylene-dioxybenzyl)]-piperazide.
Claim 8
Dependent Claim 27 words
A pharmaceutical composition for treating arrhythmia or hypertension, which composition comprises an effective amount of a compound or salt as in claim 1 and a pharmaceutical carrier.
Claim 9
Dependent Claim 31 words
A method for treating arrhythmia or hypertension in a patent suffering therefrom, which method comprises administering to said patient an effective amount of a compound or salt as in claim 1.

References Cited (Backward Citations)

US3320278A Cited
US3847920A Cited
US3980668A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-04-09 1982-10-09 1983-04-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-04-09 1986-10-09 1987-04-10 $3760.00 Window Closed / Lapsed
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