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US4220645A Expired / Lapsed US ⏱️ 0.0 years remaining

Chromone derivatives

Assignee: Therapeutique et Applications (Thea) SA
•
Filing: 1977-12-29
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Granted: 1980-09-02
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Expires: 1997-12-29
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Abstract

Abstract A chromone derivative has the formula: ##STR1## in which one of the radicals R, R' is a hydrogen atom or a lower alkyl radical and the other of the radicals is an aminoalkyl oxy benzoyl group having the formula: ##STR2## The derivative can be of use in the pharmaceutical industry in drugs for treating heart disorders. The derivative can be prepared from the novel intermediate compounds: ##STR3##

Inventors

  • 👤 Henri Chibret

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 00:20
CPC Classifications
C; C07; C07D; C07D311/00; C07D311/02; C07D311/04; C07D311/22; A; A61; A61P; A61P25/00; A61P25/02; A61P9/00; A61P9/06

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 132 words
A chromone derivative having the general formula: ##STR43## in which one of the radicals R and R' is in the 2 position on the chromone ring and the other of the radicals R and R' is in the 3 position, R' is a hydrogen atom or a lower alkyl radical, and R is the group: ##STR44## in which both R 1 and R 2 are a hydrogen atom or a lower alkyl radical, n is an integer of from 1 to 5, R 3 and R 4 are identical or different and comprise a hydrogen atom or a lower cycloalkyl radical or a hydroxy substituted lower cycloalkyl or alkyl radical, or form with the nitrogen atom a heterocyclic ring selected from the group consisting of pyrrolidine, piperidine, morpholine and N-hydroxy ethyl piperazine.
Claim 2
Dependent Claim 132 words
A chromone derivative having the general formula: ##STR43## in which one of the radicals R and R' is in the 2 position on the chromone ring and the other of the radicals R and R' is in the 3 position, R' is a hydrogen atom or a lower alkyl radical, and R is the group: ##STR44## in which both R 1 and R 2 are a hydrogen atom or a lower alkyl radical, n is an integer of from 1 to 5, R 3 and R 4 are identical or different and comprise a hydrogen atom or a lower cycloalkyl radical or a hydroxy substituted lower cycloalkyl or alkyl radical, or form with the nitrogen atom a heterocyclic ring selected from the group consisting of pyrrolidine, piperidine, morpholine and N-hydroxy ethyl piperazine.
Claim 3
Dependent Claim 16 words
The derivative of claim 1, wherein R' is a hydrogen atom when in the 2 position.
Claim 4
Dependent Claim 17 words
The derivative of claim 1, wherein R' is a lower alkyl radical when in the 3 position.
Claim 5
Dependent Claim 11 words
The derivative of claim 3, wherein R' is a methyl radical.
Claim 6
Dependent Claim 32 words
The derivative of claim 1, wherein R 1 is the same as R 2 and is a hydrogen atom or a methyl group and wherein n is 2, 3, 4 or 5.
Claim 7
Dependent Claim 19 words
The derivative of claim 1, wherein R 3 and R 4 are an ethyl, n-butyl or 2-hydroxy propyl group.
Claim 8
Dependent Claim 21 words
The derivative of claim 1, wherein R 3 is a hydrogen atom and R 4 is an isopropyl or terbutyl group.
Claim 9
Dependent Claim 21 words
The derivative of claim 1, wherein R 3 is a cyclohexyl group and R 4 is a methyl or isopropyl group.
Claim 10
Dependent Claim 34 words
The derivative of claim 1, wherein R 3 and R 4 combine with the nitrogen atom to form a heterocyclic ring selected from the group consisting of pyrrolidine, piperidine, morpholine and N-hydroxy ethyl piperazine.
Claim 11
Dependent Claim 20 words
The derivative of claim 1, which is in the form of a salt of addition of a pharmaceutically acceptable acid.
Claim 12
Dependent Claim 16 words
The derivative of claim 1, wherein R is in the 2 position on the chromone ring.
Claim 13
Dependent Claim 123 words
The derivative of claim 1, which is selected from the group consisting of 2-[4-(3N,N-dibutylamino propoxy)3,5-dimethyl benzoyl] chromone hydrochloride, 3-[4-(3-N,N-dibutylamino propoxy)3,5-dimethyl benzoyl] chromone hydrochloride, 2-[2-(3-N,N-dibutylamino propoxy) benzoyl] chromone hydrochloride, 2-[4-(2-N,N-diethylamino ethoxy) benzoyl] chromone hydrochloride, 2[4-(3-N,N-dibutylamino propoxy) benzoyl] chromone hydrochloride, 2-[4-(3-N,N-dibutylamino propoxy) 3,5-dimethyl benzoyl] 3-methyl chromone hydrochloride, 2-[4-(2-N,N-dibutylamino ethoxy) 3,5-dimethyl benzoyl] chromone hydrochloride, 2-[4-(3-N-isopropylamino propoxy) 3,5-dimethyl benzoyl] chromone hydrochloride, 2-[4-(3-N, terbutylamino propoxy) 3,5-dimethyl benzoyl] chromone hydrochloride 2[4-(N, cylcohexyl 3-N-isopropylamino propoxy) 3,5- dimethyl benzoyl]chromone hydrochloride, 2-[4-(3-N-morpholino propoxy) 3,5-dimethyl benzoyl] chromone iodomethylate, 2-[4-(N-hydroxyethyl 3-piperazino) 3,5-dimethyl benzoyl] chromone hydrochloride 2-[4-(3-N,N-diiasopropanolamino propoxy) 3,5-dimethyl benzoyl] chromone hydrochloride, 2-[4-(3-N-piperidino propoxy) 3,5-dimethyl benzoyl] chromone iodomethylate, 2-[4-(N-methyl 3-N-cyclohexoamino propoxy) 3,5-dimethyl benzoyl] chromone iodomethylate, 2-[4-(4-N,N-dibutylamino butoxy) 3,5-dimethyl benzoyl] chromone iodomethylate, 2-[4-(5-N, N-dibutylamino pentoxy) 3,5-dimethyl benzoyl] chromone iodomethylate, and 2-[4-(3-N-pyrrolidino propoxy) 3,5-dimethyl benzoyl] chromone iodomethylate.
Claim 14
Dependent Claim 32 words
A pharmaceutical composition useful in treating arrhythmia, bradycardia, tachycardia, and heart disorders necessitating sympathico inhibition comprising an effective amount of a derivative of claim 1 and a pharmaceutically acceptable carrier or diluent.
Claim 15
Dependent Claim 20 words
The pharmaceutical composition of claim 13, which is in a tablet or pill form containing from 50 to 300 mg.
Claim 16
Dependent Claim 18 words
The pharmaceutical composition of claim 14 which is in tablet or pill form containing 100 or 200 mg.
Claim 17
Dependent Claim 30 words
A method of treating arrhythmia, bradycardia, tachycardia, and heart disorders necessitating sympathico inhibition which comprises administering an effective amount of a non-toxic dosage of the pharmaceutical composition of claim 13.

References Cited (Backward Citations)

US2897211A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1983-09-02 1984-03-03 1984-09-02 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1987-09-02 1988-03-03 1988-09-02 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1991-09-02 1992-03-03 1992-09-02 $7700.00 Window Closed / Lapsed

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