Drug – bio-affecting and body treating compositions – Antigen – epitope – or other immunospecific immunoeffector – Parasitic organism or component thereof or substance...
Patent
1980-02-02
1984-05-01
Schwartz, Richard A.
Drug, bio-affecting and body treating compositions
Antigen, epitope, or other immunospecific immunoeffector
Parasitic organism or component thereof or substance...
424263, 546199, 546221, 546271, A61K 31445, C07D40104
Patent
active
044461410
DESCRIPTION:
BRIEF SUMMARY
Technical Field
The present invention relates to novel piperidine derivatives, acid addition salts thereof and pharmaceutical compositions containing the same.
The piperidine derivatives are compounds represented by the general formula (I): ##STR3## [wherein Ar represents a naphthyl, phenyl or substituted phenyl group, Q represents ##STR4## (wherein R.sub.1 is a hydrogen atom or an alkyl, alkanoyl or alkyoxycarbonyl group), R represents a hydrogen atom or an alkyl group, and Z represents a substituted benzimidazolinyl group; the broken line in piperidine ring means that the 3,4-positions in the piperidine ring are saturated or form a double bond]. The compounds represented by the general formula (I) and the pharmaceutically acceptable acid addition salts thereof have a hypotensive action, and therefore are useful as medicine.
Background Art
As the compounds structurally analogous to the compounds of the general formula (I), there have been known some compounds wherein arylalkyl hyrocarbon having an aromatic substituent and containing 3 or 4 carbon atoms in the aliphatic moiety is bonded to the nitrogen atom in the piperidine ring of the general formula (I). For example, the following compounds are commercially available as tranquilizers.
4'-fluoro-4-[4-(2-oxobenzimidazolin-1-yl) piperid-1-yl] butyrophenone (trade name: Benperidol) ##STR5##
1-{1-[4-(P-fluorophenyl)-4-oxobutyl]-1,2,3,6-tetrahydro-4-pyridyl}-2-benzim idazolinone (trade name: Droperidol) ##STR6##
1-{1-[4,4-bis(P-fluorophenyl)butyl]-4-piperidyl}-2-benzimidazolinone (trade name: Pimozide) ##STR7##
Compounds having excellent pharmacological activities are always in demand. In order to obtain such compounds, studies have been made on piperidine derivatives and as a result, it has been found that novel piperidine derivatives represented by the general formula (I) have a hypotensive action.
Disclosure of Invention
The present invention relates to the compounds represented by the above general formula (I), acid addition salts thereof and their use as medicine.
Each symbol in the general formula (I) is explained in detail below.
The substituent in the substituted phenyl group represented by Ar is a straight- or branched-chain alkoxy group having 1-6 carbon atoms, a hydroxy group, a benzyloxy group or an alkylenedioxy group having 1-3 carbon atoms, and the substituted phenyl group has 1-5 substituents at the benzene ring.
Examples of the substituent are alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy and t-butoxy, a benzyloxy group and alkylenedioxy groups such as methylenedioxy, ethylenedioxy and propylenedioxy.
Examples of the substituted phenyl group are 3,4-dihydroxyphenyl, 3-hydroxyphenyl, 3,4-dimethoxyphenyl, 3,4-methylenedioxyphenyl, 3,4,5-trimethoxyphenyl, 3,4-dibenzyloxyphenyl and 3-benzyloxyphenyl.
Examples of the naphthyl represented by Ar are 1-naphthyl and 2-naphthyl.
The alkyl group represented by R.sub.1 in the definition of Q is straight- or branched-chain alkyl having 1-5 carbon atoms such as methyl, ethyl, n-propyl, i-propyl and n-butyl. The alkanoyl group represented by R.sub.1 has the alkyl moiety the definition of which is the same as that of the above-mentioned alkyl group, and the examples thereof are acetyl and propionyl.
The alkyl group represented by R has the same definition as the alkyl group represented by R.sub.1.
Z is a substituted benzimidazolinyl group represented by the following formula (a) or (b). ##STR8##
The alkyl groups represented by R.sub.2 and R.sub.3 have the same definition as the alkyl group represented by R.sub.1. The alkanoyl group represented by R.sub.2 has the same definition as the alkanoyl group represented by R.sub.1. The alkoxycarbonyl group represented by R.sub.2 is alkoxycarbonyl having 2-6 carbon atoms such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl and t-butoxycarbonyl.
Acid addition salts of the compounds represented by the general formula (I) are, for example, inorganic acid addition salts such as hydrochloride, hydrobromide, hydriodide, sulfate and phosphate and org
REFERENCES:
patent: 3318900 (1967-05-01), Janssen
patent: 3910930 (1975-10-01), Janssen
patent: 3929801 (1975-12-01), Janssen
patent: 4031226 (1977-06-01), Soudijn et al.
patent: 4264613 (1981-04-01), Regnier et al.
patent: 4344948 (1982-08-01), Takai et al.
Wellens, D., et al., Arch. Int. Pharmacodyn. 215, 91-103, (1975).
Kasuya Yutaka
Kubo Kazuhiro
Nakamizo Nobuhiro
Obase Hiroyuki
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