Thiaxanthene derivatives, compositions thereof and methods of treating therewith
AssigneeKefalas A/S
InventorsJorn Lasse Martin Buus, Niels Lassen, Allan Johan Bigler
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Abstract
Fluoro-substituted thiaxanthene derivatives as well as their non-toxic pharmaceutically acceptable acid addition salts having pronounced neuroleptic properties and a relatively low degree of undesired side effects, methods of preparation of said derivatives, pharmaceutical compositions containing same which may be administered to animals, including human beings, orally or parenterally.
Claims31
A compound selected from the group consisting of (1) a fluoro-substituted thiaxanthene of the formula ##STR13## wherein X is selected from the group consisting of --Cl, --CF.sub.3 and --SO.sub.2.sup.. N(CH.sub.3).sub.2, Z is selected from the group consisting of >CH.sup.. CH.sub.2 --and >C.dbd.CH--, and Y is selected from the group consisting of >NH, >N.sup.. CH.sub.3, >N.sup.. CH.sub.2.sup.. CH.sub.2 OH, >N.sup.. CH.sub.2.sup.. CH.sub.2 OAc, >CH.sup.. CH.sub.3, >CH.sup.. CH.sub.2.sup.. CH.sub.2 OH and >CH.sup.. CH.sub.2.sup.. CH.sub.2 OAc, wherein --Ac is an acyl radical of an aliphatic carboxylic acid having from one to 30 carbon atoms inclusive, and (2) and acid addition salt thereof with a pharmaceutically acceptable acid.
A compound according to clainm 1 which is the palmitic acid ester of 2-trifluoromethyl-6-fluoro-9-(3-(4-(2-hydroxyethyl)-piperazine-1-yl)propyl )-thiaxanthene.
A pharmaceutical composition useful as a neuroleptic and anti-psychotic in unit dosage form consisting essentially of a major quantity of a pharmaceutical carrier and as an active ingredient a pharmaceutically effective dose of a compound selected from the group consisting of (1) a fluoro-substituted thiaxanthene of the formula:
- ##STR14## wherein X is selected from the group consisting of --Cl, --CF.sub.3 and SO.sub.2.sup.. N(CH.sub.3).sub.2, Z is selected from the group consisting of >
- CH.sup.. CH.sub.2 -- and >
- C.dbd.CH--, and Y is selected from the group consisting of >
- NH, >
- N.sup.. CH.sub.3, >
- N.sup.. CH.sub.2.sup.. CH.sub.2 OH, >
- N.sup.. CH.sub.2.sup.. CH.sub.2.sup.. OAc, >
- CH.sup.. CH.sub.2.sup.. CH.sub.2 OH and >
- CH.sup.. CH.sub.2.sup.. CH.sub.2 OAc, wherein --Ac is an acyl radical of an aliphatic carboxylic acid having from one to thirty carbon atoms inclusive, and (2) an acid addition salt thereof with a pharmaceutically acceptable acid.
A method for producing neuroleptic and antipsychotic effects in warm-blooded animals which consists essentially of administering to said warm-blooded animal an antipsychotic effective amount of a compound selected from the group consisting of:
- (1) a fluoro-substituted thiaxanthene of the formula ##STR15## wherein X is selected from the group consisting of --Cl, --CF.sub.3 and --SO.sub.2.sup.. N(CH.sub.3 ).sub.2, Z is selected from the group consisting of >
- CH.sup.. CH.sub.2 -- and >
- C.dbd.CH--, and Y is selected from the group consisting of >
- NH, >
- N.sup.. CH.sub.3, >
- N.sup.. CH.sub.2.sup.. CH.sub.2 OH, >
- N.sup.. CH.sup.. CH.sub.2 OAc, >
- CH.sup.. CH.sub.3, >
- CH.sup.. CH.sub.2.sup.. CH.sub.2 OH and >
- CH.sup.. CH.sub.2.sup.. CH.sub.2 OAc, wherein --Ac is an acyl radical of an aliphatic carboxylic acid having from one to thirty carbon atoms inclusive, and (2) an acid addition salt thereof with a pharmaceutically acceptable acid.
The method of claim 27 wherein the compound to be administered to said warm-blooded animal is the compound described in claim 24 wherein X is CF.sub.3, Z is >
- CH.sup.. CH.sub.2 -- and Y is >
- N.sup.. CH.sub.2.sup.. CH.sub.2 OH.
Dependencies are inferred from the claim text.