# US 4,396,629 A · Compositions, processes and method

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- Number: US 4,396,629 A
- Document ID: US4396629A
- Status: Granted
- Kind: A
- Application number: 06/220,412
- Filed: 1980-12-29
- Granted: 1983-08-02
- Earliest claimed: 1980-12-29
- Assignees: Sterling Drug Inc.
- Inventors: Richard E. Philion
- Web page: https://patentgrep.com/patent/US4396629A

## CPC

- C07D 303/24: with polyhydroxy compounds
- C07C 317/00: Sulfones; Sulfoxides
- C07C 381/12: Sulfonium compounds
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Therapeutically useful 1-(substituted-amino)-3-[4-R.sub.1 O-3-(lower-alkylthio, lower-alkylsulfinyl or lower-alkylsulfonyl)phenoxy]-2-propanols are obtained by reacting a 4-R.sub.1 0-3-(lower-alkylthio, lower-alkylsulfinyl or lower-alkylsulfonyl)phenol with an epihalohydrin and reacting the resulting product with a primary amine. The compounds have both antihypertensive and .beta.-adrenergic blocking activity and are useful as antihypertensive agents.

## Claims

### Claim 1

A compound having the formula ##STR20## wherein: Y is lower-alkylthio, lower-alkylsulfinyl or lower-alkylsulfonyl;
R.sub.1 is hydrogen, lower-alkyl or benzyl;
R.sub.2 is lower-alkyl or ##STR21## R.sub.3 and R.sub.4 are independently hydrogen or lower-alkyl; Q is hydrogen, lower-alkyl, hydroxy or lower-alkoxy; and
n is 1, 2 or 3;
or an acid-addition salt thereof.

### Claim 2 (depends on 1)

A compound according to claim 1 where R.sub.2 is ##STR22##

### Claim 3 (depends on 2)

A compound according to claim 2 wherein Y is methylthio, methylsulfinyl or methylsulfonyl.

### Claim 4 (depends on 3)

A compound according to claim 3 wherein n is 2.

### Claim 5 (depends on 4)

A compound according to claim 4 wherein Q is lower-alkoxy.

### Claim 6 (depends on 5)

A compound according to claim 5 wherein Y is methylsulfinyl.

### Claim 7 (depends on 6)

A compound according to claim 6 wherein R.sub.1 is hydrogen.

### Claim 8 (depends on 6)

1-[4-Methoxy-3-(methylsulfinyl)phenoxy]-3-[[3-(4-methoxyphen yl)-1-methylpropyl]amino]-2-propanol or an acid addition salt thereof according to claim 6.

### Claim 9 (depends on 7)

1-[4-Hydroxy-3-(met hylsulfinyl)phenoxy]-3-[[3-(4-methoxyphenyl)-1-methylpropyl]amino]-2-propan ol or an acid-addition salt thereof according to claim 7.

### Claim 10 (depends on 5)

A compound according to claim 5 wherein Y is methylsulfonyl.

### Claim 11 (depends on 10)

A compound according to claim 10 wherein R.sub.1 is hydrogen.

### Claim 12 (depends on 11)

1-[4-Hydroxy-3-(methylsulfonyl)phenoxy]-3-[[3-(4-methoxypheny l)-1-methylpropyl]amino]-2-propanol or an acid-addition salt thereof according to claim 11.

### Claim 13 (depends on 1)

A compound according to claim 1 wherein R.sub.2 is lower-alkyl.

### Claim 14 (depends on 13)

A compound according to claim 13 wherein Y is methylthio, methylsulfinyl or methylsulfonyl.

### Claim 15 (depends on 14)

A compound according to claim 14 wherein Y is methylthio.

### Claim 16 (depends on 15)

1-(t-Butylamino)-3-[4-methoxy-3-(methylthio)phenoxy]-2-propanol or an acid-addition salt thereof according to claim 15.

### Claim 17 (depends on 14)

A compound according to claim 14 wherein Y is methylsulfinyl.

### Claim 18 (depends on 17)

A compound according to claim 17 wherein R.sub.1 is hydrogen.

### Claim 19 (depends on 17)

1-(t-Butylamino)-3-[4-methoxy-3-(methylsulfinyl)phenoxy]-2-propanol or an acid-addition salt thereof according to claim 17.

### Claim 20 (depends on 18)

1-(t-Butylamino)-3-[4-hydroxy-3-(methylsulfinyl)phenoxy]-2-propanol or an acid-addition salt thereof according to claim 18.

### Claim 21 (depends on 14)

A compound according to claim 14 wherein Y is methylsulfonyl.

### Claim 22 (depends on 21)

A compound according to claim 21 wherein R.sub.1 is hydrogen.

### Claim 23 (depends on 22)

1-(t-Butylamino)-3-[4-hydroxy-3-(methylsulfonyl)phenoxy]-2-propanol or an acid-addition salt thereof according to claim 22.

### Claim 24 (depends on 1)

A pharmaceutical composition comprising a compound according to claim 1 in admixture with a pharmaceutically acceptable excipient.

### Claim 25 (depends on 2)

A pharmaceutical composition comprising a compound according to claim 2 in admixture with a pharmaceutically acceptable excipient.

### Claim 26 (depends on 9)

A pharmaceutical composition comprising a compound according to claim 9 in admixture with a pharmaceutically acceptable excipient.

### Claim 27 (depends on 13)

A pharmaceutical composition comprising a compound according to claim 13 in admixture with a pharmaceutically acceptable excipient.

### Claim 28 (depends on 1)

The method of lowering blood pressure in a mammal in need of such treatment which comprises administering to said mammal a blood pressure-lowering effective amount of a compound according to claim 1.

### Claim 29 (depends on 2)

The method of lowering blood pressure in a mammal in need of such treatment which comprises administering to said mammal a blood pressure-lowering effective amount of a compound according to claim 2.

### Claim 30 (depends on 9)

The method of lowering blood pressure in a mammal in need of such treatment which comprises administering to said mammal a blood pressure-lowering effective amount of a compound according to claim 9.

### Claim 31 (depends on 13)

The method of lowering blood pressure in a mammal in need of such treatment which comprises administering to said mammal a blood pressure-lowering effective amount of a compound according to claim 13.