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US4042697A Expired / Lapsed US ⏱️ 0.0 years remaining

Isoquinolium compounds for treating diabetes

Assignee: Allen and Hanburys Ltd
•
Filing: 1975-11-17
•
Granted: 1977-08-16
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Expires: 1995-11-17
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Abstract

Abstract Compounds of the general formula 1; ##STR1## in which R 1 and R 5 which may be the same or different represent an alkyl, alkenyl or alkynyl group, which groups may optionally be substituted by an amino, alkylamino or dialkylamino groups, or by hydroxy, alkoxy (C 1-4 ), aroyl, aryl or aryloxy groups, in which the aroyl, aryl or aryloxy groups may contain an alkoxy (C 1-4 ) substituent; and R 5 may in addition represent a cycloalkyl group containing from 4 to 8 carbon atoms or a heterocyclic group; R 2 and R 3 which may be the same or different represent a hydrogen atom or an alkyl group; R 4 represents a hydrogen atom or an alkyl group which alkyl group may be substituted by an aryl or aryloxy group which aryl group or aryloxy group may be substituted by an alkoxy (C 1-4 ) substituent, or R 4 may represent an aryl group which may be substituted by an alkoxy (C 1-4 ) substituent; and X represents a pharmaceutically acceptable anion of an inorganic or organic acid. These compounds have therapeutic utility particularly improving glucose utilization.

Inventors

  • 👤 Peter Garside
  • 👤 Michael John Dimsdale

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 12:01
CPC Classifications
C; C07; C07D; C07D217/00; C07D217/02; C07D217/10; C07D217/12; C07D217/14; C07D217/16

Claims Analysis

Total Claims: 15
Claim 1
Independent Claim 91 words
A method of treatment of diabetes which comprises administering to a patient an effective amount of a compound of the formula: ##STR6## in which R 1 represents C 1-4 alkyl; aminoethyl; dimethylaminoethyl; 2-ethoxyethyl; allyl; propynyl; benzyl, p-methoxybenzyl; phenoxyethyl; phenacyl or 4-methoxyphenacyl; R 2 represents hydrogen or C 1-4 alkyl; R 3 represents hydrogen; R 4 represents hydrogen; methyl, ethyl; benzyl; or p-methoxyphenyl; R 5 represents C 1-5 alkyl; 2-aminoethyl; 2-hydroxyethyl; 2-ethoxyethyl, 2-methoxyethyl, 3-methoxypropyl, ethoxymethyl; allyl, dimethylallyl; cyclopentyl; benzyl; phenoxyethyl or 3-tetrahydrofuranyl; X represents iodide, bromide, chloride, toluene sulphonate or hydrogen sulphate.
Claim 2
Independent Claim 91 words
A method of treatment of diabetes which comprises administering to a patient an effective amount of a compound of the formula: ##STR6## in which R 1 represents C 1-4 alkyl; aminoethyl; dimethylaminoethyl; 2-ethoxyethyl; allyl; propynyl; benzyl, p-methoxybenzyl; phenoxyethyl; phenacyl or 4-methoxyphenacyl; R 2 represents hydrogen or C 1-4 alkyl; R 3 represents hydrogen; R 4 represents hydrogen; methyl, ethyl; benzyl; or p-methoxyphenyl; R 5 represents C 1-5 alkyl; 2-aminoethyl; 2-hydroxyethyl; 2-ethoxyethyl, 2-methoxyethyl, 3-methoxypropyl, ethoxymethyl; allyl, dimethylallyl; cyclopentyl; benzyl; phenoxyethyl or 3-tetrahydrofuranyl; X represents iodide, bromide, chloride, toluene sulphonate or hydrogen sulphate.
Claim 3
Dependent Claim 24 words
The method of claim 1 wherein R 1 represents methyl, ethyl, isopropyl or butyl; and R 5 represents methyl, ethyl, isopropyl, pentyl or isopentyl.
Claim 4
Dependent Claim 12 words
The method of claim 1 wherein the compound is 6-(2-ethoxyethoxy)-2-methylisoquinolinium bromide monohydrate.
Claim 5
Independent Claim 18 words
A method of treatment of diabetes which comprises administering to a patient an effective amount of 6-ethoxy-2-(2-hydroxyethyl)isoquinolinium bromide.
Claim 6
Independent Claim 18 words
A method of treatment of diabetes which comprises administering to a patient an effective amount of 6-ethoxy-2-(2-hydroxyethyl)isoquinolinium bromide.
Claim 7
Dependent Claim 11 words
The method of claim 1 wherein the compound is administered orally.
Claim 8
Dependent Claim 22 words
The method of claim 5 wherein the effective amount of the compound is in a dosage range of from 5-500 mg daily.
Claim 9
Dependent Claim 11 words
The method of claim 1 wherein the compound is 6-methoxy-2-methylisoquinolinium iodide.
Claim 10
Dependent Claim 11 words
The method of claim 1 wherein the compound is 6-methoxy-2,3-dimethylisoquinolinium iodide.
Claim 11
Dependent Claim 11 words
The method of claim 1 wherein the compound is 6-methoxy-1,2-dimethylisoquinolinium iodide.
Claim 12
Dependent Claim 11 words
The method of claim 1 wherein the compound is 6-ethoxy-2-butylisoquinolinium iodide.
Claim 13
Dependent Claim 13 words
The method of claim 1 wherein the compound is 6-ethoxy-2-ethylisoquinolinium hydrogen sulphate, monohydrate.
Claim 14
Dependent Claim 12 words
The method of claim 1 wherein the compound is 6-ethoxy-2-methylisoquinolinium bromide monohydrate.
Claim 15
Dependent Claim 12 words
The method of claim 1 wherein the compound is 6-ethoxy-2,3-dimethylisoquinolinium bromide monohydrate.

References Cited (Backward Citations)

US3235556A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-08-15 1981-02-14 1981-08-16 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-08-15 1985-02-14 1985-08-16 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-08-15 1989-02-14 1989-08-16 $7700.00 Window Closed / Lapsed

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