# US 4,391,815 A · Cyanobenzano[b]pyrans

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- Number: US 4,391,815 A
- Document ID: US4391815A
- Status: Granted
- Kind: A
- Application number: 06/198,280
- Filed: 1980-10-17
- Granted: 1983-07-05
- Earliest claimed: 1976-04-02
- Assignees: Beecham Group Limited
- Inventors: John M. Evans
- Web page: https://patentgrep.com/patent/US4391815A

## CPC

- C07D 493/04: Ortho-condensed systems
- C07D 311/22: with oxygen or sulfur atoms directly attached in position 4
- C07D 311/58: other than with oxygen or sulphur atoms in position 2 or 4
- C07D 311/68: with nitrogen atoms directly attached in position 4
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

2,2-Dimethyl-3,4-dihydro-2H-benzo[b]pyran-3-ols bearing an amino group in the 4-position and a cyano group in the benzo ring, their salts, esters and ethers, demonstrate excellent vasodilatory activity. The compounds, of which trans-2,2-dimethyl-4-isopropylamino-6-cyano-3,4-dihydro-2H-benzo[b]pyran-3 -ol is a representative embodiment, can be prepared from the corresponding 3,4-epoxy derivative upon treatment with an amine.

## Claims

### Claim 1

A compound selected from the group consisting of benzo[b]pyran of the formula: ##STR3## and the pharmaceutically acceptable acid addition salts thereof wherein R is hydrogen, alkyl of 1 to 3 carbon atoms, alkanoyl of up to 8 carbon atoms or benzoyl,
NR.sub.1 R.sub.2 is pyrrolidino, and the depicted cyano group is the 6-position.

### Claim 2 (depends on 1)

A compound according to claim 1 wherein R is hydrogen.

### Claim 3

The compound which is trans-2,2-dimethyl-4-pyrrolidino-6-cyano-3,4-dihydro-2H-benzo[b]pyran-3-ol or its hydrochloride salt.

### Claim 4 (depends on 3)

The compound according to claim 3 which is the hydrochloride salt.

### Claim 5 (depends on 3)

The compound according to claim 3 which is the (+) isomer.

### Claim 6 (depends on 5)

The compound according to claim 5 which is the hydrochloride salt.

### Claim 7 (depends on 1)

A pharmaceutical composition which comprises an anti-hypertensively effective amount of a compound according to claim 1 and a pharmaceutically acceptable carrier therefor.

### Claim 8

A pharmaceutical composition which comprises an anti-hypertensively effective amount of trans-2,2-dimethyl-4-pyrrolidino-6-cyano-3,4-dihydro-2H-benzo[b]pyran-3-ol or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

### Claim 9 (depends on 8)

A composition according to claim 8 wherein the compound is (+)-trans-2,2-dimethyl-4-pyrrolidino-6-cyano-3,4-dihydro-2H-benzo[b]pyran- 3-ol or a pharmaceutically acceptable salt thereof.

### Claim 10 (depends on 8)

A composition according to claim 8 in orally administrable form and containing from about 1 to about 100 mg of said compound.

### Claim 11 (depends on 10)

A composition according to claim 10 which contains from 2 to 50 mg. of said compound.

### Claim 12 (depends on 10)

A composition according to claim 10 which contains from 5 to 25 mg. of said compound.

### Claim 13 (depends on 1)

A method of treating hypertension in a human which comprises administering thereto an effective amount of a compound according to claim 1.

### Claim 14 (depends on 5)

A method of treating hypertension in a human which comprises administering an effective amount of a compound according to claim 5.