Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1988-06-24
1990-06-05
Sutto, Anton H.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
5142358, 544121, 544295, 544372, 544374, 544394, A61K 31495, C07D40310, C07D40314
Patent
active
049314432
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
The present invention relates to a new and therapeutically useful piperazine compound or a pharmaceutically acceptable salt thereof, and to its pharmaceutical use as well as to an intermediate for its synthesis.
BACKGROUND OF THE INVENTION
Until now, a wide variety of antipsychotic drugs have been developed for the treatment of schizophrenia, mania, etc. Most of these drugs, however, are often found to cause extrapyramidal symptoms which are represented by delayed dyskinesia, Parkinson's disease, etc. in patients receiving continuous administration over a long period and make it difficult for the patients to participate in a social life or return to society.
DISCLOSURE OF THE INVENTION
Taking note of this fact, the present inventors made studies to develop an antipsychotic drug with less adverse reaction on the extrapyramidal system, thus completing the present invention. Accordingly, the present invention relates to a piperazine compound represented by the general formula: ##STR2## wherein Ar represents aryl or heteroaryl; A represents lower alkylene; Z represents --O-- or --NR-- [wherein R represents a hydrogen atom, lower alkyl, aryl, aralkyl, acyl, a group represented by the formula: ##STR3## (wherein R.sup.1 and R.sup.2 independently represent a hydrogen atom, lower alkyl, aralkyl or a group which cooperates with the adjacent nitrogen atom to form a 5 to 7-membered heterocycle; B represents lower alkylene) or a group represented by the formula: aryl)], or a pharmaceutically acceptable acid addition salt thereof.
In the present specification, lower alkyl means straight-chain or branched-chain alkyl with 1 to 4 carbon atoms, including methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl; lower alkenyl means straight-chain or branched-chain alkenyl with 1 to 4 carbon atoms, including vinyl, 1-propenyl, allyl, isopropenyl and 2-butenyl; aryl includes phenyl and naphthyl or phenyl and naphthyl bearing on their aromatic ring at least 1 substituent chosen from halogen (chlorine, bromine, iodine and fluorine), lower alkyl, lower alkoxy (straight-chain or branched-chain alkoxy with 1 to 4 carbon atoms, e.g. methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy and tert-butoxy), hydroxyl group, trifluoromethyl, cyano, nitro and amino; aralkyl includes benzyl, phenylethyl, phenylpropyl, phenylbutyl, naphthylmethyl, naphthylethyl, naphthylpropyl and naphthylbutyl or benzyl, phenylethyl, phenylpropyl, phenylbutyl, naphthylmethyl, naphthylethyl, naphthylpropyl and naphthylbutyl bearing on their aromatic ring at least 1 substituent chosen from halogen, lower alkyl, lower alkoxy, hydroxyl group, trifluoromethyl, cyano, nitro and amino; heteroaryl includes pyridyl, pyrimidyl, thienyl and furyl or pyridyl, pyrimidyl, thienyl and furyl bearing on their ring at least 1 substituent chosen from halogen, lower alkyl, lower alkoxy, hydroxyl group, trifluoromethyl, cyano, nitro and amino; the 5 to 7-membered heterocycle formed with a nitrogen atom may further have oxygen, sulfur or --NR.sup.4 -- (wherein R.sup.4 represents hydrogen, lower alkyl, hydroxy lower alkyl, aryl or aralkyl) as heteroatoms, including pyrrolidinyl, piperidino, piperazinyl, 4-methyl-1-piperazinyl, 4-(2-hydroxyphenyl)-1-piperazinyl, 4-phenyl-1-piperazinyl, 4-benzyl-1-piperazinyl, morpholino, thio-morpholino and homopiperidino; acyl includes acetyl, propionyl, butyryl, pivaloyl, benzoyl, phenylacetyl, phenylpropionyl and phenylbutyryl or benzoyl, phenylacetyl, phenylpropionyl and phenylbutyryl bearing on their phenyl nucleus at least 1 substituent chosen from halogen, lower alkyl and lower alkoxy; lower alkylene means straight-chain or branched-chain alkylene with 1 to 4 carbon atoms, including methylene, ethylene, trimethylene, propylene, tetramethylene, 1-methyltrimethylene and 2-methylmethylene.
Examples of pharmaceutically acceptable acid addition salts of the compound (I) of the present invention include inorganic acid salts such as hydrochloride, hydrobromide, sulfate and phosphate, and organic acid salts
REFERENCES:
patent: 3941789 (1976-03-01), Renth et al.
patent: 3956314 (1976-05-01), Strubbe et al.
patent: 4219551 (1980-08-01), Seidelmann et al.
Witte et al., Chemical Abstracts, vol. 99, No. 105277t (1983).
Goldstein et al., Journal of Pharmacology and Experimental Therapeutics, 249, p. 673 (1989).
Morimoto Yasuto
Morita Kenji
Nakao Toru
Obata Minoru
Bernhardt E.
Sutto Anton H.
Yoshitomi Pharmaceutical Industries Ltd.
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