# US 4,395,409 A · Carbamoyloxyamino-1,4-benzodiazepines and medicaments containing these compounds

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- Number: US 4,395,409 A
- Document ID: US4395409A
- Status: Granted
- Kind: A
- Application number: 06/269,689
- Filed: 1981-06-02
- Granted: 1983-07-26
- Earliest claimed: 1980-06-04
- Assignees: Hoechst Aktiengesellschaft
- Inventors: Manfred Forsch; Hermann Gerhards
- Web page: https://patentgrep.com/patent/US4395409A

## CPC

- C07D 243/20: Nitrogen atoms
- A61P 25/26: Psychostimulants, e.g. nicotine, cocaine
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

What are disclosed are 1,4-benzodiazepines, having a carbamoyloxyamino group, of the following formula I ##STR1## tautomers thereof of the following formula IA ##STR2## physiologically tolerated salts thereof, said compounds having an anxiolytic action without sedating, a process for the preparation of these new compounds, pharmaceutical agents which contain the active compounds, and methods for treating anxiety states with said compounds.

## Claims

### Claim 1

A carbamoyloxyamino-1,4-benzodiazepine of the formula ##STR12## or of the formula ##STR13## or a physiologically tolerated salt of such a compound, wherein R.sup.1 is halogen, nitro, or trifluoromethyl;
R.sup.2 is phenyl, pyridyl, or phenyl which is mono- or di-substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, hydroxy, halogen, or trifluoromethyl;
R.sup.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, monoalkylcarbamoyloxy, or dialkylcarbamoyloxy; and
R.sup.4 is phenyl or phenyl which is mono- or di-substituted by halogen, nitro, cyano, trifluoromethyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, hydroxy, or dialkylamino having 1-4 carbon atoms in each alkyl.

### Claim 2

7-Chloro-2-(3-chlorophenylcarbamoyloxyamino)-5-phenyl-3H-1,4-benzodiazep ine.

### Claim 3

5 -(2-Chlorophenyl)-2-(3-chlorophenylcarbamoyloxyamino)-7-nitro-3H-1,4-benzod iazepine.

### Claim 4

7-Chlo ro-5-(2-chlorophenyl)-2-(3-chlorophenylcarbamoyloxyamino)-3H-1,4-benzodiaze pine.

### Claim 5

2- (3-Chlorophenylcarbamoyloxyamino)-5-(2-fluorophenyl)-7-nitro-3H-1,4-benzodi azepine.

### Claim 6

2-(3- Chlorophenylcarbamoyloxyamino)-7-nitro-5-phenyl-3H-1,4-benzodiazepine.

### Claim 7

7-Chloro-2-(3-chlorophenylcarbamoyloxyamino)-5-(2-fluorophenyl)-3H- 1,4-benzodiazepine.

### Claim 8 (depends on 1)

A pharmaceutical preparation for the treatment of anxiety states comprising an anxiolytic amount of a compound as in claim 1 and a pharmaceutically acceptable carrier therefor.

### Claim 9 (depends on 1)

A method for treating anxiety states in a patient in need of such treatment, which method comprises orally or parenterally administering to said patient an anxiolytic amount of a compound as in claim 1.