# US 4,396,550 A · Dibenz [b,e] oxepin derivatives

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 4,396,550 A
- Document ID: US4396550A
- Status: Granted
- Kind: A
- Application number: 06/256,037
- Filed: 1981-04-21
- Granted: 1983-08-02
- Earliest claimed: 1980-04-22
- Assignees: Kyowa Hakko Kogyo Co., Ltd.
- Inventors: Hiroshi Takizawa; Osamu Morita; Yoshimasa Oiji; Tamotsu Hashimoto
- Web page: https://patentgrep.com/patent/US4396550A

## CPC

- C07D 491/10: Spiro-condensed systems
- C07D 313/12: [b,e]-condensed
- C07D 453/02: containing not further condensed quinuclidine ring systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Novel dibenz [b,e] oxepin derivatives represented by the general formula: ##STR1## wherein R.sub.11 represents an alkyl group containing 1 to 5 carbon atoms, an alkoxy group containing 1 to 5 carbon atoms, a halogen atom, a cyclohexyl group or a phenyl group; and R.sub.21 represents ##STR2## wherein X represents a hydrogen atom, a hydroxy group, an amino group or a substituted aralkyl group containing 7 to 20 carbon atoms, and n represents 0 or an integer of 1 to 3 ##STR3## or (3) --NH--(CH.sub.2).sub.n --Y, wherein Y represents an alkylamino group containing 1 to 5 carbon atoms, an aralkyl group containing 7 to 20 carbon atoms, a substituted aralkyl group, an aralkyloxy group containing 7 to 20 carbon atoms, an aralkylamino group containing 7 to 20 carbon atoms, a heterocyclic ring or a substituted heterocyclic ring, and n has the same meaning as defined before; provided that when R.sub.11 represents an alkyl group, an alkoxy group or a halogen atom, X does not represent a hydrogen atom; and the pharmaceutically acceptable acid addition salts thereof. Also disclosed are pharmaceutical compositions comprising a pharmaceutical carrier and, as an active ingredient, an effective amount of a dibenz [b,e] oxepin derivative represented by the following general formula: ##STR4## wherein R.sub.1 represents an alkyl group containing 1 to 5 carbon atoms, an alkoxy group containing 1 to 5 carbon atoms, a halogen atom, a cyclohexyl group or a phenyl group; and R.sub.2 represents ##STR5## wherein X represents a hydrogen atom, a hydroxy group, an amino group or a substituted aralkyl group containing 7 to 20 carbon atoms, and n has the same meaning as defined before ##STR6## or (3) --NH--(CH.sub.2).sub.n --Y, wherein Y and n have the same meaning as defined above; and the pharmaceutically acceptable acid addition salts thereof. Compound I, represented by the general formula (I), has antichlolinergic, antihistaminergic, antiasthmatic and antiplatelet aggregation activities, and is therefore useful as a sposmolysant, an antihistaminic, an antiasthmatic agent and as a medicament for cardiovascular or cerebrovascular diseases, respectively.

## Claims

### Claim 1

A dibenz[b,e]oxepin compound represented by the formula: ##STR59## wherein R.sub.11 represents an alkyl group having 1 to 5 carbon atoms or a cyclohexyl group; and R.sub.21 represents --NH--(CH.sub.2).sub.n --Y, wherein Y represents an alkylamino group having 1 to 5 carbon atoms and n represents an integer of 1 to 3; and the pharmaceutically acceptable acid addition salts thereof.

### Claim 2 (depends on 1)

A dibenz[b,e]oxepin compound of claim 1 wherein R.sub.11 represents an alkyl group containing 1 to 5 carbon atoms.

### Claim 3 (depends on 2)

A dibenz[b,e]oxepin compound of claim 2 wherein the alkyl group represents a methyl group, an ethyl group, a propyl group or a butyl group.

### Claim 4 (depends on 3)

A dibenz[b,e]oxepin compound of claim 3 wherein the alkyl group represents a methyl group or an ethyl group.

### Claim 5 (depends on 1)

A dibenz[b,e]oxepin compound of claim 1 wherein R.sub.11 represents a cyclohexyl group.

### Claim 6 (depends on 1)

A dibenz[b,e]oxepin compound of claim 1 wherein Y represents a methylamino group, an ethylamino group, a propylamino group, a dimethylamino group or a diethylamino group, and n has the same meaning as defined before.

### Claim 7 (depends on 6)

A dibenz[b,e]oxepin compound of claim 6 wherein Y represents a dimethylamino group or a diethylamino group, and n has the same meaning as defined before.

### Claim 8

2-ethyl-11-{2-(diethylamino)ethyl}amino-6,11-dihydrodibenz[b,e]oxepin.

### Claim 9

2-methyl-11-{3-diethylamino)propyl}amino-6,11-dihydrodibenz[b,e]oxepin.

### Claim 10

2-ethyl-11-{3-(dimethylamino)propyl}amino-6,11-dihydrodibenz[b,e]oxepin

### Claim 11

2-ethyl-11-{2-(dimethylamino)ethyl}amino-6,11-dihydrodibenz[b,e]oxepin.

### Claim 12

2-cyclohexyl-11-{2-(diethylamino)ethyl}amino-6,11-dihydrodibenz[b,e]oxe pin.