# US 5,348,964 A · Piperidyl ethers and thioethers as inhibitors of cholesterol biosynthesis

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- Number: US 5,348,964 A
- Document ID: US5348964A
- Status: Granted
- Kind: A
- Application number: 08/092,278
- Filed: 1993-07-15
- Granted: 1994-09-20
- Earliest claimed: 1990-07-25
- Assignees: Merrell Dow Pharmaceuticals Inc.
- Inventors: Charlotte L. Barney; James R. McCarthy; Marion W. Wannamaker
- Web page: https://patentgrep.com/patent/US5348964A

## CPC

- C07D 295/088: to an acyclic saturated chain
- C07D 211/22: by oxygen atoms
- C07D 211/46: having a hydrogen atom as the second substituent in position 4
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention relates to certain novel piperidyl ethers and thioethers which are useful as inhibitors of cholesterol biosynthesis and as agents which lower total serum cholesterol in patients in need thereof.

## Claims

### Claim 1

A method of inhibiting the biosynthesis of cholesterol in a patient in need thereof comprising administering to said patient an effective cholesterol biosynthesis inhibiting amount of a compound of the formula ##STR7## wherein Y is oxygen, sulfur, sulfinyl or sulfonyl;
A is a C.sub.2 -C.sub.15 alkylene having 0 to 3 double bonds;
B is a C.sub.2 -C.sub.15 alkyl having 0 to 3 double bonds;
v is a integer 0, 1 or 2; and
R is hydroxy, C.sub.1 -C.sub.4 alkyl or a radical of the formula ##STR8## wherein n is an integer 0, 1, 2 or 3; and
R.sub.1 R.sub.2 and R.sub.3 are each independently hydrogen or a C.sub.1 -C.sub.4 alkyl.

### Claim 2

A method of lowering plasma cholesterol in a patient in need thereof comprising administering to said patient an effective hypocholesterolemic amount of a compound of the formula ##STR9## wherein Y is oxygen, sulfur, sulfinyl or sulfonyl;
A is a C.sub.2 -C.sub.15 alkylene having 0 to 3 double bonds;
B is a C.sub.2 -C.sub.15 alkyl having 0 to 3 double bonds;
v is an integer 0, 1 or 2; and
R is hydroxy, C.sub.1 -C.sub.4 alkyl or a radical of the formula ##STR10## wherein n is an integer 0, 1, 2 or 3; and
R.sub.1 R.sub.2 and R.sub.3 are each independently hydrogen or a C.sub.1 -C.sub.4 alkyl.

### Claim 3

A method of treating a patient afflicted with hypercholesterolemia comprising administering to said patient an effective hypocholesterolemic amount of a compound of the formula ##STR11## wherein Y is oxygen, sulfur, sulfinyl or sulfonyl;
A is a C.sub.2 -C.sub.15 alkylene having 0 to 3 double bonds;
B is a C.sub.2 -C.sub.15 alkyl having 0 to 3 double bonds;
v is an integer 0, 1 or 2; and
R is hydroxy, C.sub.1 -C.sub.4 alkyl or a radical of the formula ##STR12## wherein n is an integer 0, 1, 2 or 3; and
R.sub.1 R.sub.2 and R.sub.3 are each independently hydrogen or a C.sub.1 -C.sub.4 alkyl.

### Claim 4

A pharmaceutical composition comprising an effective hypocholesterolemic amount of a compound of the formula ##STR13## wherein Y is oxygen, sulfur, sulfinyl or sulfonyl;
A is a C.sub.2 -C.sub.15 alkylene having 0 to 3 double bonds;
B is a C.sub.2 -C.sub.15 alkyl having 0 to 3 double bonds;
v is an integer 0, 1 or 2; and
R is hydroxy, C.sub.1 -C.sub.4 alkyl or a radical of the formula ##STR14## wherein n is an integer 0, 1, 2 or 3; and
R.sub.1 R.sub.2 and R.sub.3 are each independently hydrogen or a C.sub.1 -C.sub.4 alkyl
in admixture or otherwise in association with one or more pharmaceutically acceptable carriers or excipients.

### Claim 5 (depends on 1)

A method of claim 1 wherein the compound is [2-(1-piperidyl)pentyl isopentyl sulfide]5-(1-piperidyl)pentyl isopentyl sulfide.

### Claim 6 (depends on 1)

A method of claim 1 wherein the compound is [2-(1-piperidyl)pentyl isopentyl sulfoxide]5-(1-piperidyl)pentyl isopentyl sulfoxide.

### Claim 7 (depends on 1)

A method of claim 1 wherein the compound is [2-(1-piperidyl)pentyl isopentyl sulfone]5-(1-piperidyl)pentyl isopentyl sulfone.

### Claim 8 (depends on 1)

A method of claim 1 wherein the compound is [2-(1-piperidyl)propyl isopentyl sulfide]3-(1-piperidyl)propyl isopentyl sulfide.

### Claim 9 (depends on 1)

A method of claim 1 wherein the compound is 2-(1-piperidyl)ethyl ethyl sulfide.

### Claim 10

A method of treating a patient afflicted with a fungal infection comprising administering an effective antifungal amount of a compound of the formula ##STR15## wherein Y is oxygen, sulfur, sulfinyl or sulfonyl;
A is a C.sub.2 -C.sub.15 alkylene having 0 to 3 double bonds;
B is a C.sub.2 -C.sub.15 alkyl having 0 to 3 double bonds;
v is an integer 0, 1 or 2; and
R is hydroxy, C.sub.1 -C.sub.4 alkyl or a radical of the formula ##STR16## wherein n is an integer 0, 1, 2 or 3; and
R.sub.1 R.sub.2 and R.sub.3 are each independently hydrogen or a C.sub.1 -C.sub.4 alkyl.

### Claim 11 (depends on 1)

A method of claim 1 wherein the compound is 9-(1-piperidyl)nonanyl isopropyl ether.

### Claim 12 (depends on 1)

A method of claim 1 wherein the compound is 3-(1-piperidyl)propyl hexyl ether.

### Claim 13 (depends on 1)

A method of claim 1 wherein the compound is 2-(1-piperidyl)ethyl heptyl ether.