# US 4,381,309 A · 1-Aryloxy-2-hydroxy-3-((heterocyclic-substituted alkyl)-amino)-propanes and salts thereof

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- Number: US 4,381,309 A
- Document ID: US4381309A
- Status: Granted
- Kind: A
- Application number: 06/195,650
- Filed: 1980-10-09
- Granted: 1983-04-26
- Earliest claimed: 1976-10-05
- Assignees: Boehringer Ingelheim GmbH
- Inventors: Herbert Koppe; Anton Mentrup; Ernst-Otto Renth; Kurt Schromm; Wolfgang Hoefke; Gojko Muacevic
- Web page: https://patentgrep.com/patent/US4381309A

## CPC

- C07D 215/227: only one oxygen atom which is attached in position 2
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 25/24: Antidepressants
- A61P 25/26: Psychostimulants, e.g. nicotine, cocaine
- C07D 209/34: in position 2
- C07D 233/32: One oxygen atom
- C07D 235/26: Oxygen atoms
- C07D 265/18: with hetero atoms directly attached in position 2
- C07D 265/28: 1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Compounds of the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are hydrogen or substituents of various types; R.sub.4 is hydrogen, alkyl of 1 to 5 carbon atoms, or optionally substituted aralkyl of 7 to 14 carbon atoms; R.sub.5 is a heterocycle; D is alkylene of 1 to 12 carbon atoms; and A is hydrogen or acyl; and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as .alpha.- and .beta.-adrenergic receptor blocking agents and antidepressants.

## Claims

### Claim 1

A compound of the formula ##STR117## wherein R.sub.4 is hydrogen, alkyl of 1 to 5 carbon atoms, or aralkyl of 7 to 14 carbon atoms;
R.sub.5 is ##STR118## where R.sub.10 and R.sub.11 are each hydrogen, halogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, trifluoromethyl, carboxamido or, together with each other, --O--(CH.sub.2).sub.y --O--, where y is 1 or 2, attached to carbon atoms of the phenyl ring in o-position with respect to each other; and
D is alkylene of 1 to 12 carbon atoms,
or a non-toxic, pharmacologically acceptable acid addition salt thereof.

### Claim 2 (depends on 1)

A compound of claim 1, wherein
R.sub.4 is hydrogen or methyl;
R.sub.5 is ##STR119## D is alkylene of 2 to 8 carbon atoms, or a non-toxic, pharmacologically acceptable acid addition salt thereof.

### Claim 3

A compound of the formula ##STR120## wherein R.sub.4 is hydrogen or methyl; and
D' is alkylene of 2 to 8 carbon atoms,
or a non-toxic, pharmacologically acceptable acid addition salt thereof.

### Claim 4 (depends on 3)

The compound of claim 3, which is 1-(2-cyanophenoxy)-3-[1,1-dimethyl-4-(N-benzimidazolon(2)yl)-butylamino-1] -propanol-(2) or a non-toxic, pharmacologically acceptable acid addition salt thereof.

### Claim 5 (depends on 1, 3)

An .alpha.- and .beta.-adrenolytic pharmaceutical dosage composition consisting essentially of an inert pharmaceutical carrier and an effective amount of a compound of claims 1 or 3.

### Claim 6 (depends on 1, 3)

The method of blocking the .alpha.- and .beta.-adrenergic receptors in a warm-blooded animal in need thereof, which comprises perorally, parenterally or rectally administering to said animal an effective amount of a compound of claims 1 or 3.