IP Library Granted Patent US 12,258,309
Granted Patent B2
US 12,258,309 · App. 18/347,808 · Granted Mar 25, 2025

Ultra short acting anti-arrhythmic agents

Inventors: John Somberg (Lake Forest, IL); Robert J Chorvat (Chadds Ford, PA)
Assignee: Academic Pharmcauticals, Inc.
C07C317/28
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Quick Facts
Patent No.
US 12,258,309
App. No.
18/347,808
Granted
Mar 25, 2025
Kind
B2
Abstract

Some aspects provide novel dofetilide derivatives and pharmaceutical compositions containing the same that are useful as pharmaceutical agents in the treatment of supraventricular and ventricular arrhythmias.

Claims (141)

1. A compound of Formula I-III or a stereoisomer thereof:

Formula

Formula

I

II

III

wherein:

R is selected from H, C 1-6 alkyl, C 3-6 alkenyl, and C 3-6 alkynyl; and,

m is selected from 0 and 1;

or a pharmaceutically acceptable salt thereof.

2. A compound of claim 1 , wherein the compound is of Formula I:

wherein the compound is selected from the following table:

R

m

 1.

CH 3

0

 2.

CH 2 CH 3

0

 3.

CH 2 CH 2 CH 3

0

 4.

CH 2 CH═CH 2

0

 5.

CH 3

1

 6.

CH 2 CH 3

1

 7.

CH 2 CH 2 CH 3

1

 8.

CH 2 CH═CH 2

1

 9.

CH 3

2

10.

CH 2 CH 3

2

11.

CH 2 CH 2 CH 3

2

12.

CH 2 CH═CH 2

2

or pharmaceutically acceptable salt thereof.

3. A compound of claim 1 , wherein the compound is of Formula II:

wherein the compound is selected from the following table:

R

M

 1.

CH 3

0

 2.

CH 2 CH 3

0

 3.

CH 2 CH 2 CH 3

0

 4.

CH 2 CH=CH 2

0

 5.

CH 3

1

 6.

CH 2 CH 3

1

 7.

CH 2 CH 2 CH 3

1

 8.

CH 2 CH=CH 2

1

 9.

CH 3

2

10.

CH 2 CH 3

2

11.

CH 2 CH 2 CH 3

2

12.

CH 2 CH=CH 2

2

or pharmaceutically acceptable salt thereof.

4. A compound of claim 1 , wherein the compound is of Formula III:

wherein the compound is selected from the following table:

R

m

 1.

CH 3

0

 2.

CH 2 CH 3

0

 3.

CH 2 CH 2 CH 3

0

 4.

CH 2 CH═CH 2

0

 5.

CH 3

1

 6.

CH 2 CH 3

1

 7.

CH 2 CH 2 CH 3

1

 8.

CH 2 CH═CH 2

1

 9.

CH 3

2

10.

CH 2 CH 3

2

11.

CH 2 CH 2 CH 3

2

12.

CH 2 CH═CH 2

2

or pharmaceutically acceptable salt thereof.

5. A pharmaceutical composition, comprising: a therapeutically effective amount of a compound of claim 1 or pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

6. A pharmaceutical composition, comprising: a therapeutically effective amount of a compound of claim 2 or pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

7. A pharmaceutical composition, comprising: a therapeutically effective amount of a compound of claim 3 or pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

8. A pharmaceutical composition, comprising: a therapeutically effective amount of a compound of claim 4 or pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

9. A method of terminating or blocking the occurrence of an arrhythmia, comprising: administering to a patient in need thereof a therapeutically effective amount of a compound of claim 1 or pharmaceutically acceptable salt thereof, wherein the arrhythmia is selected from: paroxysmal atrial tachycardia, junctional ectopic tachycardia, atrial flutter, atrial fibrillation, atrial tachycardia, ventricular tachycardia, junctional tachycardia, and ventricular fibrillation.

10. A method of terminating or blocking the occurrence of an arrhythmia, comprising: administering to a patient in need thereof a therapeutically effective amount of a compound of claim 2 or pharmaceutically acceptable salt thereof, wherein the arrhythmia is selected from: paroxysmal atrial tachycardia, junctional ectopic tachycardia, atrial flutter, atrial fibrillation, atrial tachycardia, ventricular tachycardia, junctional tachycardia, and ventricular fibrillation.

11. A method of terminating or blocking the occurrence of an arrhythmia, comprising: administering to a patient in need thereof a therapeutically effective amount of a compound of claim 3 or pharmaceutically acceptable salt thereof, wherein the arrhythmia is selected from: paroxysmal atrial tachycardia, junctional ectopic tachycardia, atrial flutter, atrial fibrillation, atrial tachycardia, ventricular tachycardia, junctional tachycardia, and ventricular fibrillation.

12. A method of terminating or blocking the occurrence of an arrhythmia, comprising: administering to a patient in need thereof a therapeutically effective amount of a compound of claim 4 or pharmaceutically acceptable salt thereof, wherein the arrhythmia is selected from: paroxysmal atrial tachycardia, junctional ectopic tachycardia, atrial flutter, atrial fibrillation, atrial tachycardia, ventricular tachycardia, junctional tachycardia, and ventricular fibrillation.

Continuity (3)
Continuation 17645723 · Dec 22, 2021
Provisional Application 63199436 · Dec 28, 2020
Related Publication 20240025846A1 · Jan 25, 2024
References Cited (10)
US 10793519B2 · Somberg · 2020 [cited by examiner]
US 11286235B2 · Somberg · 2022 [cited by examiner]
US 11731938B2 · Somberg · 2023 [cited by examiner]
Erhardt1, J. Med. Chem. 1983, 26, 1109-1112. [cited by examiner]
Erhardt, J. Med. Chem. 1982, 25, 1402-1407. [cited by examiner]
Tikosyn-Dofetilide Label, Revised Aug. 2019. [cited by applicant]
Erhardt, P.W., et al., Ultra-Short-Acting B-Adrenergic Receptor Blocking Agents. 1. (Aryloxy)propanolamines Containing Esters in the Nitrogen Substituent, J. Med. Chem. 1982, 25, 1402-1407. [cited by applicant]
Erhardt, P.W., et al., Ultra-Short-Acting B-Adrenergic Receptor Blocking Agents. 3. Ethylenediamine Derivatives of (Aryloxy)propanolamines Having Esters on the Aryl Function, J. Med. Chem. 1983, 26, 1109-1112. [cited by applicant]
Murray, K.T., et al., Suppression of ventricular arrhythmias in man by d-propanolol independent of beta-adrenergic receptor blockade, J. Clin. Invest. 1990, 83(3), 836-42. [cited by applicant]
Walker, D.K., et al., Significance of Metabolism in the Disposition and Action of the Antidysrhythmic Drug, Dofetilide, Drug Metab. Dispos. 1996, 24(4), 447-55. [cited by applicant]