JPH02233670A - Piperazinosulfonic acid derivative - Google Patents
Piperazinosulfonic acid derivativeInfo
- Publication number
- JPH02233670A JPH02233670A JP1054140A JP5414089A JPH02233670A JP H02233670 A JPH02233670 A JP H02233670A JP 1054140 A JP1054140 A JP 1054140A JP 5414089 A JP5414089 A JP 5414089A JP H02233670 A JPH02233670 A JP H02233670A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- expressed
- solvent
- temperature
- compound
- 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.)
- Pending
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- BHJHVDDOCMGCDD-UHFFFAOYSA-N piperazin-1-ium-1-sulfonate Chemical class OS(=O)(=O)N1CCNCC1 BHJHVDDOCMGCDD-UHFFFAOYSA-N 0.000 title claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 13
- 239000002904 solvent Substances 0.000 abstract description 11
- 150000001875 compounds Chemical class 0.000 abstract description 9
- -1 cyclic sulfonic acid ester Chemical class 0.000 abstract description 7
- 229940079593 drug Drugs 0.000 abstract description 6
- 239000003814 drug Substances 0.000 abstract description 6
- 208000010110 spontaneous platelet aggregation Diseases 0.000 abstract description 4
- 208000007536 Thrombosis Diseases 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 3
- 230000002265 prevention Effects 0.000 abstract description 3
- 208000011775 arteriosclerosis disease Diseases 0.000 abstract description 2
- 238000009835 boiling Methods 0.000 abstract description 2
- 206010008118 cerebral infarction Diseases 0.000 abstract description 2
- 208000026106 cerebrovascular disease Diseases 0.000 abstract description 2
- 230000002093 peripheral effect Effects 0.000 abstract description 2
- 150000004885 piperazines Chemical class 0.000 abstract description 2
- 230000003405 preventing effect Effects 0.000 abstract description 2
- 238000010992 reflux Methods 0.000 abstract description 2
- 206010061216 Infarction Diseases 0.000 abstract 1
- 230000000747 cardiac effect Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000007574 infarction Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000008640 diphenylmethylpiperazines Chemical class 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 210000003743 erythrocyte Anatomy 0.000 description 5
- ZDVDCDLBOLSVGM-UHFFFAOYSA-N [chloro(phenyl)methyl]benzene Chemical class C=1C=CC=CC=1C(Cl)C1=CC=CC=C1 ZDVDCDLBOLSVGM-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000004089 microcirculation Effects 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 206010050661 Platelet aggregation inhibition Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- GSNOZLZNQMLSKJ-UHFFFAOYSA-N Trapidil Chemical compound CCN(CC)C1=CC(C)=NC2=NC=NN12 GSNOZLZNQMLSKJ-UHFFFAOYSA-N 0.000 description 1
- 229940090012 bentyl Drugs 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000002327 cardiovascular agent Substances 0.000 description 1
- 229940125692 cardiovascular agent Drugs 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229940125890 compound Ia Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- CURUTKGFNZGFSE-UHFFFAOYSA-N dicyclomine Chemical group C1CCCCC1C1(C(=O)OCCN(CC)CC)CCCCC1 CURUTKGFNZGFSE-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- NWVNXDKZIQLBNM-UHFFFAOYSA-N diphenylmethylpiperazine Chemical compound C1CNCCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 NWVNXDKZIQLBNM-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229960000363 trapidil Drugs 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は、新規なピベラジノスルホン酸誘導体に関する
。DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to novel piperazinosulfonic acid derivatives.
近年、虚血状態下の微小循環を改善するためには、単な
る血管拡張剤による治療だけでは不十分とされ、赤血球
変形能を冗進したり血小板の機能を制御することにより
、血液性状を積極的に改善することが望まれてきている
。即ち血栓症や微小循環障害の治療において、赤血球変
形能冗進作用及び血小板凝集阻止作用を有する薬剤が注
目されるようになってきた。そこで既存の循環器用剤に
ついて、ヘモレオロジー的立場からの検討が成され、ベ
ントキシフィリン、トラピジル、ジラゼップなどが血液
性状の改善薬としても有効であることが認められるよう
になった。しかし、それらの血液性状改善作用はまだま
だ満足できるものではない。従って、微小血管内流動に
対する血液流体力学的作用、即ち赤血球変形能冗造作用
や血小板凝集阻止作用に著効を示す薬剤の出現が要望さ
れている。In recent years, in order to improve microcirculation under ischemic conditions, it has been recognized that simple treatment with vasodilators is not sufficient, and efforts have been made to actively improve blood properties by increasing red blood cell deformability and controlling platelet function. It is hoped that improvements will be made. That is, in the treatment of thrombosis and microcirculatory disorders, drugs that have red blood cell deformability enhancing effects and platelet aggregation inhibiting effects have been attracting attention. Therefore, existing cardiovascular drugs were examined from a hemorheological standpoint, and drugs such as bentxifylline, trapidil, and dirazep were found to be effective as drugs for improving blood properties. However, their blood property improving effects are still not satisfactory. Therefore, there is a demand for a drug that exhibits significant effects on blood fluid dynamics on microvascular flow, ie, red blood cell deformability redundancy and platelet aggregation inhibition.
本発明は、一般式
(式中、R1及びR2は同一又は相異なり、水素原子、
ハロゲン原子又は低級アルコキシ基を示す。The present invention is based on the general formula (wherein R1 and R2 are the same or different, a hydrogen atom,
Indicates a halogen atom or a lower alkoxy group.
R3は水素原子又は低級アルキル基を示す。nは2〜4
の整数を示す。)で表わされるビペラジノスルホン酸誘
導体に係る。R3 represents a hydrogen atom or a lower alkyl group. n is 2 to 4
indicates an integer. ) is related to the biperazinosulfonic acid derivative represented by
上記一般式(I)で表わされる本発明ビベラジノスルホ
ン酸誘導体は文献未載の新規化合物であり、従来の薬剤
に比べて赤血球変形能先進作用が強く、かつ血小板凝集
阻止作用をも併せ持ち、血栓症及び微小循環障害の予防
及び治療に有用である。The biverazinosulfonic acid derivative of the present invention represented by the above general formula (I) is a new compound that has not been described in any literature, and has a stronger effect on red blood cell deformability than conventional drugs, and also has an effect on inhibiting platelet aggregation. It is useful for the prevention and treatment of diseases and microcirculatory disorders.
上記一般式(I)においてR3で示される低級アルキル
基としては、炭素数1〜6の直鎖又は分枝鎖状のアルキ
ル基、例えばメチル、エチル、プロビル、ブチル、t−
ブチル、ベンチル、ヘキシル基などを挙げることができ
る。R,及びR2で示されるハロゲン原子としては、塩
素、臭素、フッ素、ヨウ素原子などを挙げることができ
る。また低級アルコキシ基としては、炭素数1〜6の直
鎖又は分枝鎖状のアルコキシ基例えばメトキシ、エトキ
シ、ブロポキシ、ブトキシ、イソブロポキシ、ヘキシル
オキシ基などを挙げることができる。The lower alkyl group represented by R3 in the above general formula (I) is a linear or branched alkyl group having 1 to 6 carbon atoms, such as methyl, ethyl, proyl, butyl, t-
Examples include butyl, bentyl, hexyl groups, and the like. Examples of the halogen atoms represented by R and R2 include chlorine, bromine, fluorine, and iodine atoms. Examples of lower alkoxy groups include linear or branched alkoxy groups having 1 to 6 carbon atoms, such as methoxy, ethoxy, propoxy, butoxy, isobropoxy, and hexyloxy groups.
本発明化合物(I)は、例えば、以下の方法によって製
造することができる。Compound (I) of the present invention can be produced, for example, by the following method.
(m)
(式中R,%R2 、R3及びnは前記に同じ)ジフエ
ニルクロルメタン誘導体(II)とピペラジン誘導体(
m)との反応は、適当な溶媒中で行なわれる。この反応
によって、ジフエニルメチルビペラジン誘導体(IV)
を得ることが.できる。ジフエニルク口ルメタン誘導体
(II)とビペラジン誘導体(m)の使用割合は特に制
限されないが、通常前者に対して後者を2.0〜2.2
モル量程度使用すればよい。溶媒としては反応に影響を
与えないものがいずれも使用でき、例えば、メタノール
、エタノール、ブロパノールなどの低級アルコール類、
ジエチルエーテル、イソブロビルエーテル、テトラハイ
ドロフラン、ジオキサンなどのエーテル類、ベンゼン、
トルエンなどの芳香族炭化水素類などを挙げることがで
きる。反応は、室温から溶媒の沸点の範囲で有利に進行
し、通常11〜24時間程度で終了する。(m) (in the formula, R, %R2, R3 and n are the same as above) diphenylchloromethane derivative (II) and piperazine derivative (
The reaction with m) is carried out in a suitable solvent. By this reaction, diphenylmethylbiperazine derivative (IV)
To obtain. can. The ratio of the diphenylmethane derivative (II) and the biperazine derivative (m) to be used is not particularly limited, but the ratio of the latter to the former is usually 2.0 to 2.2.
It is sufficient to use about a molar amount. Any solvent that does not affect the reaction can be used, such as lower alcohols such as methanol, ethanol, and propanol;
Ethers such as diethyl ether, isobrobyl ether, tetrahydrofuran, dioxane, benzene,
Examples include aromatic hydrocarbons such as toluene. The reaction proceeds advantageously in a range from room temperature to the boiling point of the solvent, and usually completes in about 11 to 24 hours.
上記方法で得られるジフェニルメチルビベラジン誘導体
(IV)は、単離するかあるいは単離することなく次の
反応に使用できる。The diphenylmethyl biverazine derivative (IV) obtained by the above method can be used in the next reaction with or without isolation.
ジフエニルメチルピペラジン誘導体(IV)と環状スル
ホン酸エステル(V)との反応は、適当な溶媒中で行な
われる。ジフエニルメチルピペラジン誘導体(IV)と
環状スルホン酸エステル(V)の使用割合は特に制限さ
れないが、通常前者に対して後者を1〜1.5倍モル量
程度使用すればよい。適当な溶媒としては、例えば、メ
タノール、エタノール、プロパノール、イソプロバノー
ルなどの低級アルコール類、アセトン、メチルエチルケ
トン、ジエチルケトンなどの低級ケトン類、ベンゼン、
トルエンなどの芳香族炭化水素類又はこれらの混合溶媒
などを挙げることができる。反応は、上記2種の原料化
合物を0℃〜室温程度の温度下に溶媒に加えた後、攪拌
下、室温〜還流温度程度の温度下に行なわれ、通常数時
間〜数日間程度で終了する。The reaction between the diphenylmethylpiperazine derivative (IV) and the cyclic sulfonic acid ester (V) is carried out in a suitable solvent. The ratio of the diphenylmethylpiperazine derivative (IV) and the cyclic sulfonic acid ester (V) to be used is not particularly limited, but the latter should generally be used in an amount of about 1 to 1.5 times the molar amount of the former. Suitable solvents include, for example, lower alcohols such as methanol, ethanol, propanol, and isoprobanol, lower ketones such as acetone, methyl ethyl ketone, and diethyl ketone, benzene,
Examples include aromatic hydrocarbons such as toluene and mixed solvents thereof. The reaction is carried out under stirring at a temperature of room temperature to reflux temperature after adding the above two raw material compounds to a solvent at a temperature of about 0°C to room temperature, and usually completes in about several hours to several days. .
このようにして得られる本発明化合物(I)は、通常の
手段に従って精製単離できる。例えば、減圧濃縮するか
、またはそのままの状態で生成した沈澱を戸取した後、
水若しくはメタノール、エタノール、プロパノール、イ
ソブロパノールなどの低級アルコール類、アセトン、メ
チルエチルケトらの混合溶媒などから再結晶することに
よって精製単離することができる。The compound (I) of the present invention thus obtained can be purified and isolated by conventional means. For example, after concentrating under reduced pressure or taking the precipitate produced as it is,
It can be purified and isolated by recrystallization from water or a mixed solvent of lower alcohols such as methanol, ethanol, propanol, isopropanol, acetone, methyl ethyl keto, etc.
発明の効果
本発明化合物(I)は優れた赤血球変形能九進作用と血
小板凝集阻止作用を有しており、微小循環領域での血液
流動性を改善することから、動脈硬化症、脳梗塞、心筋
梗塞、末梢性血栓、及び閉塞などの予防及び治療に有用
である。Effects of the Invention The compound (I) of the present invention has excellent red blood cell deformability quantal action and platelet aggregation inhibiting action, and improves blood fluidity in the microcirculation area, thereby preventing arteriosclerosis, cerebral infarction, It is useful for the prevention and treatment of myocardial infarction, peripheral thrombosis, occlusion, etc.
実施例 以下に実施例を挙げて、本発明を具体的に説明する。Example The present invention will be specifically explained below with reference to Examples.
実施例1
ピペラジン3.5gのベンゼン溶液4011IQに、反
応液の温度を40℃前後に保ちながら、ジフエニルメチ
ルクロライド4.1gのベンゼン溶液を滴下した。滴下
後24時間加熱撹拌を行なった。Example 1 A benzene solution of 4.1 g of diphenylmethyl chloride was added dropwise to a benzene solution of 4011IQ containing 3.5 g of piperazine while maintaining the temperature of the reaction solution at around 40°C. After the dropwise addition, heating and stirring were performed for 24 hours.
冷却後溶媒を減圧下に留去し、得られた残液に工ーテル
100式と希炭酸水素ナトリウム液30mQを加えてエ
ーテル抽出した。エーテル層は無水硫酸ナトリウムで乾
燥後溶媒を留去し、油状のジフエニルメチルピペラジン
2.8gを得た。続いて精製することなくジフエニルメ
チルビベラジンをアセトン50或に溶解し、この溶液に
1.3−プロパンサルトン1.5gのアセトン溶液10
−を室温下に滴下した。滴下後室温で18時間撹拌した
。反応後析出物を枦取し、アセトン続いてエーテルで洗
浄し、1−(3−スルホプ口ピル)−4−(ジフエニル
メチル)ビペラジン(化合物Ia)3.4g (45%
)を得た。融点290℃分解、元素分析値を第1表に示
す。After cooling, the solvent was distilled off under reduced pressure, and to the resulting residual liquid were added Ether 100 formula and 30 mQ of diluted sodium bicarbonate solution for ether extraction. The ether layer was dried over anhydrous sodium sulfate and the solvent was distilled off to obtain 2.8 g of oily diphenylmethylpiperazine. Subsequently, diphenylmethylbiverazine was dissolved in 50 g of acetone without purification, and a solution of 1.5 g of 1.3-propanesultone in 10 g of acetone was added to this solution.
- was added dropwise at room temperature. After the addition, the mixture was stirred at room temperature for 18 hours. After the reaction, the precipitate was collected and washed with acetone and then ether to give 3.4 g (45%) of 1-(3-sulfopyr)-4-(diphenylmethyl)biperazine (compound Ia).
) was obtained. Melting point 290°C decomposition and elemental analysis values are shown in Table 1.
実施例2
実施例1と同様の方法にて化合物Ib−Ieを合成した
。それぞれの融点、収率及び元素分析値を第1表に示す
。Example 2 Compound Ib-Ie was synthesized in the same manner as in Example 1. Table 1 shows the respective melting points, yields, and elemental analysis values.
Claims (1)
子、ハロゲン原子又は低級アルコキシ基を示す。R_3
は水素原子又は低級アルキル基を示す。nは2〜4の整
数を示す。)で表わされるピペラジノスルホン酸誘導体
。[Claims] 1 General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R_1 and R_2 are the same or different and represent a hydrogen atom, a halogen atom, or a lower alkoxy group. R_3
represents a hydrogen atom or a lower alkyl group. n represents an integer of 2 to 4. ) A piperazinosulfonic acid derivative represented by
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1054140A JPH02233670A (en) | 1989-03-07 | 1989-03-07 | Piperazinosulfonic acid derivative |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1054140A JPH02233670A (en) | 1989-03-07 | 1989-03-07 | Piperazinosulfonic acid derivative |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH02233670A true JPH02233670A (en) | 1990-09-17 |
Family
ID=12962261
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP1054140A Pending JPH02233670A (en) | 1989-03-07 | 1989-03-07 | Piperazinosulfonic acid derivative |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH02233670A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1995019345A1 (en) * | 1994-01-14 | 1995-07-20 | Nippon Shoji Kabushiki Kaisha | Diazacycloalkanealkylsulfonamide derivative |
JP2679872B2 (en) * | 1989-04-28 | 1997-11-19 | 明治製菓株式会社 | Brain dysfunction improving agent containing N-substituted piperazine derivative |
-
1989
- 1989-03-07 JP JP1054140A patent/JPH02233670A/en active Pending
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2679872B2 (en) * | 1989-04-28 | 1997-11-19 | 明治製菓株式会社 | Brain dysfunction improving agent containing N-substituted piperazine derivative |
WO1995019345A1 (en) * | 1994-01-14 | 1995-07-20 | Nippon Shoji Kabushiki Kaisha | Diazacycloalkanealkylsulfonamide derivative |
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