# US 4,391,808 A · 5(1-Piperazinyl(imidazo[2,1-b][1,3,5]benzothiadiazepines

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- Number: US 4,391,808 A
- Document ID: US4391808A
- Status: Granted
- Kind: A
- Application number: 06/259,261
- Filed: 1981-05-11
- Granted: 1983-07-05
- Earliest claimed: 1980-06-12
- Assignees: Ciba-Geigy Corporation
- Inventors: Isidoros Vlattas
- Web page: https://patentgrep.com/patent/US4391808A

## CPC

- C07D 513/04: Ortho-condensed systems
- C07D 233/84: Sulfur atoms
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

5-Diazacycloalkyl-imidazo[2,1-b][1,3,5]benzothiadiazepines, e.g. those of the formula ##STR1## the N-oxides and salts thereof are neuroleptic agents, lacking extrapyramidal side-effects.

## Claims

### Claim 1

A 5-diazacycloalkyl-imidazo[2,1-b][1,3,5]benzothidiazepine compound of the formula ##STR8## wherein one of R.sub.1 and R.sub.2 is hydrogen, lower alkyl or alkanoyl, halogeno, cyano, carboxy, lower carbalkoxy, carboamoyl, sulfamoyl, mono- or di-lower alkyl-(carbamoyl or sulfamoyl), and the other of R.sub.1 and R.sub.2 is hydrogen, lower alkyl or halogeno; Ph is 1,2-phenylene, unsubstituted or substituted by on member selected from lower alkyl, lower alkoxy, lower alkylthio, halogeno, trifluoromethyl, sulfamoyl, mono- or di-lower alkyl-sulfamoyl, each of C.sub.m H.sub.2m and C.sub.n H.sub.2n is lower alkylene separating both nitrogen atoms by 2 carbon atoms; and R.sub.3 is hydrogen, lower alkyl, lower alkanoyl, lower alkoxycarbonyl, or lower hydroxyalkyl wherein the hydroxy group is separated from the nitrogen atom by at least 2 carbon atoms; the S-oxides; the N-oxides; or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

A compound as claimed in claim 1, in which formula one of R.sub.1 and R.sub.2 is hydrogen, lower alkyl or alkanoyl, halogeno, cyano, carboxy, lower carbalkoxy, carbamoyl, sulfamoyl, mono- or di-lower alkyl-(carbamoyl or sulfamoyl), and the other of R.sub.1 and R.sub.2 is hydrogen or lower alkyl; Ph is 1,2-phenylene, (lower alkyl)-1,2-phenylene, (lower alkoxy)-1,2-phenylene, (lower alkylthio)-1,2-phenylene, (halogeno)-1,2-phenylene, (trifluoromethyl)-1,2-phenylene, (sulfamoyl)-1,2-phenylene, (mono- or di-lower alkyl-sulfamoyl)-1,2-phenylene; each of m and n is the integer 2; and R.sub.3 is hydrogen, lower alkyl, lower alkanoyl, lower alkoxycarbonyl or lower hydroxyalkyl wherein the hydroxy group is separated from the nitrogen atom by at least 2 carbon atoms; the S-oxides; the N-oxides; or a pharmaceutically acceptable salt thereof.

### Claim 3 (depends on 1)

A compound as claimed in claim 1 and corresponding to the formula ##STR9## wherein each of R.sub.1 and R.sub.2 is hydrogen or lower alkyl; R.sub.4 is hydrogen, lower alkyl or lower 2- or 3-hydroxyalkyl; R.sub.5 is hydrogen, lower alkyl, lower alkoxy, halogeno or trifluoromethyl; and p is an integer from 0 to 2; the N-oxide thereof; or a pharmaceutically acceptable acid addition salt thereof.

### Claim 4 (depends on 3)

A compound as claimed in claim 3, in which formula each of R.sub.1 and R.sub.2 is hydrogen or methyl; R.sub.4 is hydrogen, alkyl or 2- or 3-hydroxyalkyl with up to 4 carbon atoms; R.sub.5 is hydrogen, methyl, methoxy, fluoro, chloro, or trifluoromethyl; and p is O; the N-oxide thereof; or a pharmaceutically acceptable acid addition salt thereof.

### Claim 5 (depends on 3)

A compound as claimed in claim 3, in which formula each of R.sub.1 and R.sub.2 is hydrogen or methyl; R.sub.4 is hydrogen, methyl or 2-hydroxyethyl; R.sub.5 is hydrogen, fluoro, chloro or trifluoromethyl; and p is O; or a pharmaceutically acceptable acid addition salt thereof.

### Claim 6 (depends on 3)

A compound as claimed in claim 3 and being the 5-(4-methylpiperazino)-imidazo[2,1-b][1,3,5]benzothiadiazepine, or a pharmaceutically acceptable acid addition salt thereof.

### Claim 7 (depends on 3)

A compound as claimed in claim 3 and being 8-chloro-5-(4-methylpiperazino)-imidazo [2,1-b][1,3,5]benzothiadiazepine, or a pharmaceutically acceptable acid addition salt thereof.

### Claim 8 (depends on 3)

A compound as claimed in claim 3 and being the 3-methyl-5-(4-methylpiperazino)imidazo [2,1-b][1,3,5]benzothiadiazepine, or a pharmaceutically acceptable acid addition salt thereof.

### Claim 9 (depends on 3)

A compound as claimed in claim 3 and being the 5-[4-(2-hydroxyethyl)piperazino]imidazo[2,1-b][1,3,5]benzothiadiazepine or a pharmaceutically acceptable acid addition salt thereof.

### Claim 10 (depends on 1)

A neuroleptic or antipsychotic pharmaceutical composition comprising an antipsychotic a neuroleptically effective amount of a compound as claimed in claim 1, together with a pharmaceutical excipient.

### Claim 11 (depends on 10)

The method of treating a psychotic condition in mammals, which comprises administering to said mammals enterally or parenterally an effective amount of a composition as claimed in claim 10.