Spirocycles

• US 5,439,914 A
• Filed: 02/18/1994
• Issued: 08/08/1995
• Est. Priority Date: 02/18/1994
• Status: Expired due to Fees

• Current Assignee: Merck & Co., Inc.
• Original Assignee: Merck & Co., Inc.
• Inventors: Selnick, Harold G., Claremon, David A., Ponticello, Gerald S.
• Primary Examiner(s): Berch, Mark L.
• Application Number:
  US08/198,940
• Time in Patent Office: 536 Days
• Field of Search: 546/17, 514/278
• US Class Current: 514/278
• CPC Class Codes: A61P 9/06 Antiarrhythmics
• CPC Class Codes: C07D 221/20 Spiro-condensed ring systems
• CPC Class Codes: C07D 491/10 Spiro-condensed systems

Abstract

Compounds of the general structural formula: ##STR1## or a pharmaceutically acceptable salt, hydrate or crystal form thereof, wherein;

X is O or CH₂

R¹ is H if R² is not H or if R² is H then R¹ is ##STR2## R² is --H if R¹ is not H or if R¹ is H then R² is; ##STR3## and R³ is ##STR4## are Class HI antiarrhythmic agents.

Claims

1. A compound of the structural formula:

##STR36## wherein;

X is CH₂ ;

R¹ is H if R² is not H or if R² is H then R¹ is ##STR37## R² is --H if R¹ is not H or if R¹ is H then R² is ##STR38## and R³ is ##STR39## or a pharmaceutically acceptable salt, hydrate or crystal form thereof.

2. The compound of claim 1 selected from the group consisting of ##STR40## 1-(RS)-1-Acetamido-1'"'"'-[2-(p-cyanophenyl)ethyl]3,4-dihydro-7-methoxyspironaphthalene -3,4'"'"'-piperidine;

##STR41## (1S)-1-Acetamido-1'"'"'-[2-(p-cyanophenyl)ethyl]3,4-dihydro-7-methoxyspironaphthalene -3,4'"'"'-piperidine;

or ##STR42##

3. A pharmaceutical formulation comprising a carrier and an amount of a compound of claim 1 which is therapeutically effective for the treatment of arrhythmia for those in need thereof.

4. The pharmaceutical formulation of claim 3, wherein the pharmaceutically effective amount of compound ranges from about 1.0 mg to about 100 mg of the compound.

5. The pharmaceutical formulation of claim 3, which comprises from about compound ranges from about 2.0 mg to about 25 mg of the compound.

6. A method of treating arrhythmia and/or impaired cardiac pump function in a patient in need of such treatment which comprises administering to such patient a therapeutically effective amount of the compound of claim 1.

7. The method of claim 6 wherein the therapeutically effective amount of compound is administered orally or intravenously.

8. The pharmaceutical formulation of claim 3 wherein the formulation is compressed into a tablet which comprises from about 1.0 mg to about 100 mg of the compound.

9. The pharmaceutical formulation of claim 3, wherein the formulation is compressed into a tablet which comprises from about 2.0 mg to about 25 mg of the compound.