# US 5,332,733 A · Heterocyclically substituted piperazinoakylbenzoxazine and piperazinoalkylbenzothiazine compounds, processes for preparing them, and medicaments containing them

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- Number: US 5,332,733 A
- Document ID: US5332733A
- Status: Granted
- Kind: A
- Application number: 07/977,859
- Filed: 1992-11-17
- Granted: 1994-07-26
- Earliest claimed: 1990-11-24
- Assignees: Kali-Chemie Pharma GmbH
- Inventors: Daniel Jasserand; Francois Floc'h; Richard White
- Web page: https://patentgrep.com/patent/US5332733A

## CPC

- C07D 265/36: condensed with one six-membered ring
- C07D 279/16: condensed with one six-membered ring
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Pharmacologically active compounds corresponding to the general formula I ##STR1## which are optionally substituted in the benzene ring and in which X denotes oxygen or sulfur, Y denotes oxygen or sulfur, R.sup.1 denotes hydrogen or lower alkyl, n is an integer from 0 to 4, and R.sup.4 is an optionally substituted 6-membered unsaturated heterocycle containing 1 or 2 nitrogen atoms not directly bonded to the piperazine ring, and physiologically acceptable acid addition salts thereof.

## Claims

### Claim 1

A compound corresponding to the formula I ##STR28## wherein X denotes oxygen or sulfur,
Y denotes oxygen or sulfur,
R.sup.1 denotes hydrogen or lower alkyl,
R.sup.2 denotes hydrogen, lower alkyl, halogen, lower alkoxy, hydroxy, nitro or trifluoromethyl, and
R.sup.3 denotes hydrogen, lower alkyl, halogen or lower alkoxy, or
R.sup.2 and R.sup.3 are bonded to adjacent carbon atoms and together denote an alkylenedioxy group having 1-2 carbon atoms,
n is an integer from 0 to 4, and
R.sup.4 is a 6-membered unsaturated heterocycle containing 1 or 2 nitrogen atoms not directly bonded to the piperazine ring, said heterocycle being substituted by 0 to 2 substituents bonded to carbon atoms selected from the group consisting of lower alkyl, lower alkoxy and halogen,
and physiologically acceptable acid addition salts thereof.

### Claim 2 (depends on 1)

A compound according to claim 1, wherein Y denotes oxygen.

### Claim 3 (depends on 1)

A compound according to claim 1, wherein n is 3 or 4.

### Claim 4 (depends on 1)

A compound according to claim 1, wherein R.sup.4 is an optionally substituted pyridyl group.

### Claim 5 (depends on 4)

A compound according to claim 4, wherein R.sup.4 is a 4-(lower alkyl)-pyrid-2-yl group.

### Claim 6 (depends on 1)

A compound according to claim 1, wherein R.sup.1 denotes hydrogen.

### Claim 7 (depends on 1)

A compound according to claim 1, wherein R.sup.2 denotes hydrogen or lower alkyl, and R.sup.3 denotes hydrogen.

### Claim 8 (depends on 1)

A compound according to claim 1, wherein Y denotes oxygen, R.sup.1 denotes hydrogen, R.sup.2 denotes hydrogen or lower alkyl, R.sup.3 denotes hydrogen, n is 3 or 4, and R.sup.4 denotes a pyridyl group optionally substituted by lower alkyl.

### Claim 9 (depends on 8)

2-{4-[4-(4-methylpyridin- 2-yl)-piperazin-1-yl]-butyl}-2H-1,4-benzothiazine-3(4H)-one according to claim 8, and physiologically acceptable acid addition salts thereof.

### Claim 10 (depends on 1)

A pharmaceutical composition comprising an effective anti-inflammatory or anti-allergic amount of a compound according to claim 1 and at least one conventional pharmaceutical adjuvant.

### Claim 11

A compound corresponding to the formula IV ##STR29## wherein X denotes oxygen or sulfur,
R.sup.1 denotes hydrogen or lower alkyl,
R.sup.2' denotes hydrogen, lower alkyl, halogen, lower alkoxy, nitro or trifluoromethyl, and
R.sup.3 denotes hydrogen, lower alkyl, halogen or lower alkoxy, or
R.sup.2' and R.sup.3 are bonded to adjacent carbon atoms and together denote an alkylenedioxy group having 1-2 carbon atoms, and
n is an integer from 0 to 4.