JPS5946227B2 - N-substituted trimethoxybenzylpiperazine derivative - Google Patents
N-substituted trimethoxybenzylpiperazine derivativeInfo
- Publication number
- JPS5946227B2 JPS5946227B2 JP51040782A JP4078276A JPS5946227B2 JP S5946227 B2 JPS5946227 B2 JP S5946227B2 JP 51040782 A JP51040782 A JP 51040782A JP 4078276 A JP4078276 A JP 4078276A JP S5946227 B2 JPS5946227 B2 JP S5946227B2
- Authority
- JP
- Japan
- Prior art keywords
- trimethoxybenzylpiperazine
- substituted
- group
- derivative
- hydrochloride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
【発明の詳細な説明】
本発明は次の一般式(I)
化合物 (1)Z
濃度g /mq〒伏壊b
イソプロペニル
ンノナミル
ルフォリノエチル
(LD5oの値は(〜/に9
本発明の化合物中は次の化学構造式(■)(式中Zはイ
ソプロペニル基、シンナミル基、又はモルフオリルエチ
ル基を示す。DETAILED DESCRIPTION OF THE INVENTION The present invention is a compound of the following general formula (I) (1) The compound has the following chemical structural formula (■) (where Z represents an isopropenyl group, a cinnamyl group, or a morpholylethyl group).
)で表わされるN一置換トリメトキシベンジルピペラジ
ン誘導体に関するものである。) N-monosubstituted trimethoxybenzylpiperazine derivatives.
本発明化合物は文献未載の新規物質であつて心運動抑制
咋用を有し、虚血性心疾患治療剤として有用である。こ
れらの薬理作用の一例として、モルモツト摘出心臓にお
けLangendorff法による心臓脈管に対する活
性、およびマウスに対するLDm値を第1表に示す。で
表示)
で表わされるトリメタジジンをアルキル化する方法によ
つて合成するのが有利であるが、アルキルピペラジン類
をトリメトキシベンジル化する方法またはN−トリメト
キシベンジルジエタノールアミン誘導体とアルキルアミ
ン類との反応によりピペラジン閉環を行なうことによつ
ても合成可能である。The compound of the present invention is a novel substance that has not been described in any literature, has a cardiac movement suppressing effect, and is useful as a therapeutic agent for ischemic heart disease. As an example of these pharmacological actions, Table 1 shows the cardiac vascular activity in isolated guinea pig hearts according to the Langendorff method, and the LDm value in mice. Although it is advantageous to synthesize trimetazidine by alkylating trimetazidine represented by It can also be synthesized by performing piperazine ring closure.
以下実施例をあげ、具体的に述べる。Hereinafter, examples will be given and concretely described.
実施例 1
(Z:イソプロペニル基)
()物質塩酸塩5.0g1イソプロペニルプロマイド3
.3g及び無水炭酸カリウム8.1gを、DMFl5O
ml中50℃で1時間撹拌、冷後常法により処理し、反
応成績体をシリカゲルカラムクロマトにて精製し、塩酸
塩とし、イソプロパノールより再結晶する。Example 1 (Z: isopropenyl group) () Substance hydrochloride 5.0 g 1 isopropenyl bromide 3
.. 3 g and 8.1 g of anhydrous potassium carbonate, DMFl5O
ml at 50° C. for 1 hour, cooled and treated in a conventional manner, and the reaction product was purified by silica gel column chromatography to form a hydrochloride salt, which was recrystallized from isopropanol.
融点205〜210℃、収量2.5g0実施例 2(Z
:シンナミル基)
()物質塩酸塩5.0g1シンナミルクロライド3.3
8g及び無水炭酸カリウム8.1gを60℃で1時間撹
拌、冷後、実施例1と同様に処理精製し、塩酸塩とし、
エタノールより再結晶する。Example 2 (Z
: cinnamyl group) () Substance hydrochloride 5.0g1 cinnamyl chloride 3.3
8g and 8.1g of anhydrous potassium carbonate were stirred at 60°C for 1 hour, cooled, and purified in the same manner as in Example 1 to obtain a hydrochloride.
Recrystallize from ethanol.
融点208とC(分解)。収量4.2g0実施例 3
(Z:モルフオリノエチル基)
()物質塩酸塩10.4g1モリフオリノエチルクロラ
イド6.56g及び無水炭酸カリウム25.1gをエタ
ノール150m1中4時間撹拌還流、冷後常法により処
理し、塩酸塩とし、メタノールより再結晶する。Melting point 208 and C (decomposed). Yield 4.2 g0 Example 3 (Z: Morpholinoethyl group) (10.4 g of substance hydrochloride 1 6.56 g of morpholinoethyl chloride and 25.1 g of anhydrous potassium carbonate were stirred under reflux for 4 hours in 150 ml of ethanol, and after cooling. It is treated in a conventional manner to form a hydrochloride salt, and then recrystallized from methanol.
Claims (1)
るN−置換トリメトキシベンジルピペラジン誘導体。 (式中Zはイソプロペニル基、シンナミル基、又はモル
フオリルエチル基を示す。 )[Scope of Claims] 1. An N-substituted trimethoxybenzylpiperazine derivative represented by the following general formula (I), ▲ which includes mathematical formulas, chemical formulas, tables, etc. ▼ (I). (In the formula, Z represents an isopropenyl group, a cinnamyl group, or a morpholylethyl group.)
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP51040782A JPS5946227B2 (en) | 1976-04-09 | 1976-04-09 | N-substituted trimethoxybenzylpiperazine derivative |
US05/783,561 US4100285A (en) | 1976-04-09 | 1977-04-01 | N-substituted trialkoxybenzyl piperazine derivatives |
DE19772714996 DE2714996A1 (en) | 1976-04-09 | 1977-04-04 | N-SUBSTITUTED TRIALCOXYBENZYLPIPERAZINE DERIVATIVES |
GB14537/77A GB1565431A (en) | 1976-04-09 | 1977-04-06 | N-substituted trialkoxybenzylpiperazine derivatives |
CH446377A CH629197A5 (en) | 1976-04-09 | 1977-04-07 | Process for the preparation of N-substituted trialkoxybenzylpiperazine derivatives |
CH446277A CH629196A5 (en) | 1976-04-09 | 1977-04-07 | Process for the preparation of N-substituted trialkoxybenzylpiperazine derivatives |
FR7710859A FR2347359A1 (en) | 1976-04-09 | 1977-04-08 | N-SUBSTITUTED TRIALCOXYBENZYLPIPERAZINE DERIVATIVES AND THEIR PHARMACEUTICAL USES, ESPECIALLY FOR THEIR VASODILATOR ACTION |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP51040782A JPS5946227B2 (en) | 1976-04-09 | 1976-04-09 | N-substituted trimethoxybenzylpiperazine derivative |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS52131588A JPS52131588A (en) | 1977-11-04 |
JPS5946227B2 true JPS5946227B2 (en) | 1984-11-10 |
Family
ID=12590185
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP51040782A Expired JPS5946227B2 (en) | 1976-04-09 | 1976-04-09 | N-substituted trimethoxybenzylpiperazine derivative |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5946227B2 (en) |
-
1976
- 1976-04-09 JP JP51040782A patent/JPS5946227B2/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
JPS52131588A (en) | 1977-11-04 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Kim et al. | Monosubstituted guanidines from primary amines and aminoiminomethanesulfonic acid | |
US4261895A (en) | Alkanoyl-proline derivatives and homologues thereof | |
US5112826A (en) | Vasodilatory dihydrodibenzocycloheptyliden-ethylpiperazine derivatives | |
JPH0226629B2 (en) | ||
CA1221967A (en) | Derivatives of piperidinedione for protecting the myocardium presenting an anti-arrythmic activity, process for preparing them and drugs containing said derivatives | |
US2918401A (en) | Treatment of nematodes with quaternary ammonium compounds | |
US2704757A (en) | 5-hydroxy-3, 4, 5, 6-tetrahydropyriminines | |
US4451473A (en) | 3,7-Diazabicyclo [3.3.1] nonanes having anti-arrhythmic activity | |
JPS5946227B2 (en) | N-substituted trimethoxybenzylpiperazine derivative | |
JPS635059A (en) | Antibacterial n-(6,6-dimethyl-2-hepten-4-ynyl)-1- naphthalenemethaneamine derivatives and use | |
US4407816A (en) | 3-Substituted-2-propenimidamides and method of manufacturing the same | |
JPS60158150A (en) | 1,4-naphthoquinone derivatives | |
US4511566A (en) | 2-N-Cycloalkylmethyl 3-oxo 5,6-diaryl-as-triazines | |
JPH02233677A (en) | New 1-(3-(2-hydroxy-3-alkylaminopropoxy)-2-thienyl)- 3-phenyl-1-propanone,and preparation thereof | |
JPS5943946B2 (en) | N-alkenylmoranoline derivative | |
JPH03167184A (en) | N-benzyltropane amides | |
US2970159A (en) | Hydrazine derivatives | |
GB1565022A (en) | Methylamine derivatives and provesses for preparing the same | |
US3420841A (en) | 1,3-di-(4-pyridyl)propane derivatives | |
EP0069527B1 (en) | Cystine derivatives | |
US3149108A (en) | Preparation of derivatives of 1, 4-benzodioxan | |
Sprinson | The synthesis of N-substituted choline carbamates and trimethyl-β-phenylaminoethylammonium chloride | |
US3072726A (en) | N1-cycloalkanoyl and n1-[alpha-tri-alkyl]-alkanoyl-hydrazides and derivatives thereof | |
US2855400A (en) | 2-methyl-pyridine-4-carboxylic acid derivatives | |
US3647785A (en) | Novel 3-indolylaliphatic acid anhydrides |