# US 5,346,901 A · Pyrazolopyrimidinone antianginal agents

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- Number: US 5,346,901 A
- Document ID: US5346901A
- Status: Granted
- Kind: A
- Application number: 08/084,827
- Filed: 1993-06-29
- Granted: 1994-09-13
- Earliest claimed: 1990-06-20
- Assignees: Pfizer Inc.
- Inventors: Andrew S. Bell; David Brown; Nicholas K. Terrett
- Web page: https://patentgrep.com/patent/US5346901A

## CPC

- C07D 487/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Compounds of the formula: ##STR1## wherein R.sup.1 is H, C.sub.1 -C.sub.3 alkyl, C.sub.3 -C.sub.5 cycloalkyl or C.sub.1 -C.sub.3 perfluoroalkyl; R.sup.2 is H, C.sub.1 -C.sub.6 alkyl optionally substituted by OH, C.sub.1 -C.sub.3 alkoxy or C.sub.3 -C.sub.6 cycloalkyl, or C.sub.1 -C.sub.3 perfluoroalkyl; R.sup.3 is C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.6 perfluoroalkyl or (C.sub.3 -C.sub.6 cycloalky)C.sub.1 -C.sub.6 alkyl; R.sup.4 taken together with the nitrogen atom to which it is attached completes a pyrrolidinyl, piperidino, morpholino, or 4-N-(R.sup.6)-piperazinyl group; R.sup.5 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy, NR.sup.7 R.sup.8, or CONR.sup.7 R.sup.8 ; R.sup.6 is H, C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.3 alkoxy) C.sub.2 -C.sub.6 alkyl, hydroxy C.sub.2 -C.sub.6 alkyl, (R.sup.7 R.sup.8 N)C.sub.2 -C.sub.6 alkyl, (R.sup.7 R.sup.8 NCO)C.sub.1 -C.sub.6 alkyl, CONR.sup.7 R.sup.8, CSNR.sup.7 R.sup.8 or C(NH)NR.sup.7 R.sup.8 ; R.sup.7 and R.sup.8 are each independently H, C.sub.1 -C.sub.4 alkyl, (C.sub.1 -C.sub.3 alkoxy)C.sub.2 -C.sub.4 alkyl or hydroxy C.sub.2 -C.sub.4 alkyl; and pharmaceutically acceptable salts thereof, are selective cGMP PDE inhibitors useful in the treatment of cardiovascular disorders such as angina, hypertension, heart failure and atherosclerosis.

## Claims

### Claim 1

A compound of the formula: ##STR22## wherein R.sup.1 is H, C.sub.1 -C.sub.3 alkyl, C.sub.3 -C.sub.5 cycloalkyl or C.sub.1 -C.sub.3 perfluoroalkyl;
R.sup.2 is H, C.sub.1 -C.sub.6 alkyl optionally substituted by OH, C.sub.1 -C.sub.3 alkoxy or C.sub.3 -C.sub.6 cycloalkyl, or C.sub.1 -C.sub.3 perfluoroalkyl;
R.sup.3 is C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.6 perfluoroalkyl or (C.sub.3 -C.sub.6 cycloalkyl)C.sub.1 -C.sub.6 alkyl;
R.sup.4 taken together with the nitrogen atom to which it is attached completes a pyrrolidinyl, piperidino, or morpholino group;
R.sup.5 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy, NR.sup.7 R.sup.8, or CONR.sup.7 R.sup.8 ;
R.sup.7 and R.sup.8 are each independently H, C.sub.1 -C.sub.4 alkyl, (C.sub.1 -C.sub.3 alkoxy)C.sub.2 -C.sub.4 alkyl or hydroxy C.sub.2 -C.sub.4 alkyl; and pharmaceutically acceptable salts thereof.

### Claim 2 (depends on 1)

A compound as claimed in claim 1 wherein R.sup.1 is H, methyl or ethyl; R.sup.2 is C.sub.1 -C.sub.3 alkyl optionally substituted by OH or methoxy; R.sup.3 is C.sub.2 -C.sub.3 alkyl or allyl; R.sup.4 taken together with the nitrogen atom to which it is attached completes a piperidino group; R.sup.5 is H, NR.sup.7 R.sup.8 or CONR.sup.7 R.sup.8 ; and R.sup.7 and R.sup.8 are each independently H or methyl.

### Claim 3 (depends on 1, 2)

A pharmaceutical composition comprising a compound of the formula (I) or a pharmaceutically acceptable salt thereof, as claimed in any one of claims 1 to 2, together with a pharmaceutically acceptable diluent or carrier.

### Claim 4 (depends on 1, 2, 3)

A method of treating, in a human being, angina, hypertension, heart failure or atherosclerosis which comprises administering to said human being an effective amount of a compound of the formula (I) or a pharmaceutically acceptable salt thereof, as claimed in any one of claims 1 to 2, or a pharmaceutical composition as claimed in claim 3.