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Piperidine derivatives and hypotensives containing the same

a technology of piperidine and derivatives, applied in the field of piperidine derivatives and hypotensives containing the same, can solve the problems of recent controversy over the safety or the effect of pharmaceuticals of these hypotensives, and achieve the effect of low cost and simple preparation

Inactive Publication Date: 2003-09-23
AJINOMOTO CO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

Accordingly, one object of the present invention is to provide an effective hypotensive agent which is relatively simple to prepare at low cost.

Problems solved by technology

Further, as the age of a given population increases, increased attention is directed to hypertension which becomes more and more of a dangerous factor in severe heart and cerebral diseases represented by cardiac infarction and cerebral apoplexy.
But the pharmaceutical effects or safety of these hypotensives have recently come into question.

Method used

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  • Piperidine derivatives and hypotensives containing the same
  • Piperidine derivatives and hypotensives containing the same
  • Piperidine derivatives and hypotensives containing the same

Examples

Experimental program
Comparison scheme
Effect test

example 1

4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-hexylpiperidine hydrochloride

A solution of 273 mg (1 mmol) of 4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-hexylpiperidine, 165 mg (1 mmol) of 1-bromohexane, 745 mg (5 mmols) of sodium iodide and 414 mg (3 mmols) of potassium carbonate in 20 ml of methyl isobutyl ketone was stirred and refluxed at 120.degree. C. overnight on an oil bath. After the reaction, the mixture was washed by adding 20 ml of water thereto. Then the organic phase was separated and the solvent was distilled off under reduced pressure. After purifying by silica gel column chromatography (eluent: methanol / chloroform, 1 / 100-1 / 50), the product was converted into the hydrochloride with an equimolar hydrogen chloride / dioxane solution. Amount yielded 180 mg Yield 46% TLC Rf=0.68 MS 357 (M+) NMR 0.83 (3H, t), 1.2-1.4 (6H, m), 1.7-1.9 (2H, m), 2.31 (2H, dd), 2.53 (2H, d), 2.7-2.8 (2H, m), 3.14 (2H, dd), 3.38 (2H, dd), 3.38 (2H, d), 6.92 (2H, s), 7.2-7.4 (8H, m)

Hereafter procedure...

example 2

4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-octylpiperidine hydrochloride Amount yielded 300 mg Yield 72% TLC Rf=0.71 MS 385 (M+) NMR 0.85 (3H, t), 1.2-1.4 (10H, m), 1.7-2.0 (2H, m), 2.30 (2H, dd), 2.53 (2H, d), 2.7-2.9 (2H, m), 3.13 (2H, dd), 3.38 (2H, d), 6.90 (2H, s), 7.1-7.4 (8H, m)

example 3

1-Decyl-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine hydrochloride Amount yielded 300 mg Yield 67% TLC Rf=0.75 MS 413 (M+) NMR 0.85 (3H, t), 1.2-1.4 (14H, m), 1.7-1.9 (2H, m), 2.33 (2H, dd), 2.54 (2H, d), 2.7-2.8 (2H, m), 3.15 (2H, dd), 3.39 (2H, d), 6.92 (2H, s), 7.1-7.4 (8H, m)

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Abstract

A piperidine compound of the formula (I): ##STR1## wherein A is a fused aromatic ring; R is hydrogen, chloro or methoxy; X is (CH.sub.2).sub.n, which may be substituted, in which n is 0 or an integer of 1 to 10, --CH.ident.CH--, --C.ident.C--, --O--, --S--, --NH--, --N(COCH.sub.3)--, --N(COOC.sub.2 H.sub.5)--, --N(CHO)--, --N(CH.sub.3)--, --CO--, --SO--, or --SO.sub.2 --; Y is --CH.ident.CH--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 CO--, --O--, --S--, --NH--, --OCH.sub.2 --, --SCH.sub.2 --, --NHCH.sub.2 --, --CH(OH)CH.sub.2 -- or --CH(OH)CH(OH)--; and Q is substituted or unsubstituted n-hexyl, carboxypropyl, ethoxycarbonylpropyl, cyanopropyl, cyclohexyl, phenyl, indanyl, naphthyl, tetrahydronaphthyl, benzocycloheptyl, piperidinyl, tetrahydroisoquinolinyl, indolyl, pyrolyl, furyl, thienyl, thiazolyl, oxazolyl or N-methylpyrolyl, wherein any one or more of the --(CH.sub.2)-groups of the hexyl, carboxypropyl, ethoxycarbonylpropyl and cyanopropyl groups may be replaced by --CH.ident.CH--, --C.ident.C--, --O--, --S--, --NH--, --N(COCH.sub.3), --N(COC.sub.2 H.sub.5)--, --N(CHO)--, --N(CH.sub.3), --CO--, --SO-- or --SO.sub.2 --, and wherein one or more of the --(CH.sub.2)-groups in X and Q may be substituted by --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 -- thereby forming a ring structure.

Description

BACKGROUND OF THE INVENTIONFIELD OF THE INVENTIONThe present invention relates to a piperidine derivative and hypotensives containing the same.DESCRIPTION OF THE BACKGROUNDIt is said that there are about 13,000,000 patients with hypertension in Japan and its frequency of occurrence in individuals becomes greater with advancing age. Further, as the age of a given population increases, increased attention is directed to hypertension which becomes more and more of a dangerous factor in severe heart and cerebral diseases represented by cardiac infarction and cerebral apoplexy. In recent years, calcium antagonists or angiotensin convertase inhibitors have been widely used as excellent primary selection drugs for treatment of hypertension. But the pharmaceutical effects or safety of these hypotensives have recently come into question.A need therefore continues to exist for new hypotensive agents which exhibit excellent pharmaceutical effects and safety which can be industrially prepared a...

Claims

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Application Information

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IPC IPC(8): C07D211/22C07D405/00C07D211/32C07C255/00C07C255/43C07D211/00C07D409/00C07D211/70C07D211/52C07D405/06C07D409/06C07D295/145C07D401/06C07D295/00C07D417/06C07D401/00C07D417/00C07D491/052
CPCC07C255/43C07D211/22C07D211/32C07D211/52C07D211/70C07D295/145C07D401/06C07D405/06C07D409/06C07D417/06C07C2603/32
Inventor SHOJI, MASATAKATOYOTA, KOZOEGUCHI, CHIKAHIKOYOSHIMOTO, RYOTAKOYAMA, YOSHIKATSUDOMOTO, HIDEKIKAMIMURA, AKIRA
Owner AJINOMOTO CO INC
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