JPS5936660A - Indoleacetic acid derivative - Google Patents
Indoleacetic acid derivativeInfo
- Publication number
- JPS5936660A JPS5936660A JP14515282A JP14515282A JPS5936660A JP S5936660 A JPS5936660 A JP S5936660A JP 14515282 A JP14515282 A JP 14515282A JP 14515282 A JP14515282 A JP 14515282A JP S5936660 A JPS5936660 A JP S5936660A
- Authority
- JP
- Japan
- Prior art keywords
- acid derivative
- indoleacetic acid
- acid
- alkyl group
- lower alkyl
- 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.)
- Granted
Links
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】 本発明は新規なインドール酢酸誘導体に関する。[Detailed description of the invention] The present invention relates to novel indoleacetic acid derivatives.
本発明べ係るインドール酢酸誘導体は、下記一般式（１
）で示される化合物である。The indole acetic acid derivative according to the present invention has the following general formula (1
) is a compound represented by
（式中Ｒ及びＲは水素原子又は低級アル十ル基を、Ｒは
低級アル＋ル基を意味する）上記一般式（１）において
、Ｒ，Ｒ及びＲ３によって示される低級アル十ル基とし
ては、炭素！＆１−６の直鎖状又は分枝状のアル＋ル基
、例えばメチル、エチル、づ０じル、イソプ０じル、ブ
チル、イソブチル、ペシチル、へ＋シル基等が挙げられ
る。(In the formula, R and R represent a hydrogen atom or a lower alkyl group, and R means a lower alkyl group.) In the above general formula (1), as a lower alkyl group represented by R, R, and R3, Ha, carbon! &1-6 straight-chain or branched alkyl groups, such as methyl, ethyl, dioxyl, isopropylene, butyl, isobutyl, pesityl, hexyl groups, and the like.
本発明の上記化合物は文献米記載の新規化合物であって
、抗炎症作用、抗リウマチ作用等を有し医薬として有用
なものである。The above-mentioned compound of the present invention is a novel compound described in the literature, and has anti-inflammatory and anti-rheumatic effects and is useful as a medicine.
本発明の上記一般式（１）で示されるインドール酢酸誘
導体は、例えば次式に示すように式（２）で示さ２−
れる酸り０リドと一般式（３）で示されるフェノール誘
導体とを反応させることにより製造することができる。The indole acetic acid derivative represented by the above general formula (1) of the present invention can be obtained by combining an acid 2-hydride represented by the formula (2) and a phenol derivative represented by the general formula (3) as shown in the following formula, for example. It can be produced by reaction.
（２） （３）
（式中Ｒ，Ｒ及びＲは前記と同じ意味を有する）
上式において、酸り０リド（２）とフェノール誘導体（
３）との反応は、一般に溶媒中、塩基性化合物の＝３−
謀であれば特に限定されないが、例えばエーテル、テト
ラしドロフラジ、ジオ十サシ等のエーテル類；ジグ０ル
メタシ、ジクＤルエタｙ、四塩化炭素類のハロゲン化炭
化水素類；ベンゼン、トルエン、十シレシ等の芳香族炭
化水素類；アセトニトリル、ジメチルホルムアミド、ジ
メチルホルホ＋シト等の非ｊｏｔ−ン性極性溶媒等を使
用できる。塩基性化合物としては例えばトリエチルアミ
ン、じリジル等の有機塩基及び水酸化ナトリウム、水酸
化カリウム、炭酸水素ナトリウム、炭酸水素カリウム、
炭酸ナトリウム、炭酸カリウム等の無機塩基を例示でき
る。酸り０リド（２）とフェノール誘導体（３）との使
用割合は、適宜選択することができるが、通常弄七ル量
程度使用するのが有利である。反応温度も適宜選択すれ
ばよいが、一般に−２０−５０°Ｃ付近において反応は
有利に進行する。(2) (3) (In the formula, R, R and R have the same meanings as above) In the above formula, the acid 0lide (2) and the phenol derivative (
The reaction with 3) is generally not limited as long as it is a basic compound in a solvent, but for example, ethers such as ether, tetrahydroflazide, dioxic acid, etc.; , halogenated hydrocarbons such as carbon tetrachloride; aromatic hydrocarbons such as benzene, toluene, and chloride; non-jot-like polar solvents such as acetonitrile, dimethylformamide, and dimethylformamide, and the like can be used. Examples of basic compounds include organic bases such as triethylamine and diridyl, and sodium hydroxide, potassium hydroxide, sodium hydrogen carbonate, potassium hydrogen carbonate,
Examples include inorganic bases such as sodium carbonate and potassium carbonate. The ratio of the acid hydride (2) and the phenol derivative (3) to be used can be selected as appropriate, but it is usually advantageous to use about 70%. Although the reaction temperature may be selected appropriately, the reaction generally proceeds advantageously at around -20 to 50°C.
上記反応によシ生成する本発明のインドール酸４−
酸誘導体（１）は、通常の分離手段により容易に単離可
能である。The indole acid 4-acid derivative (1) of the present invention produced by the above reaction can be easily isolated by conventional separation means.
次に実施例を挙げて本発明をよシ具体的に説明する。Next, the present invention will be explained in more detail with reference to Examples.
実施例 １
５−（４−しドロ＋ジフェニル） −１，１，３−トリ
メチルじウレットｌ ５ ｆ （０，０４七ル）及びト
リエチルアミン４ ｙ （０，０４′ｅル）を、テトラ
しドロフラン２００ゴに溶解し、０°Ｃに冷却する。Example 1 5-(4-dihydro+diphenyl)-1,1,3-trimethyldiuret l5f (0,047yl) and triethylamine 4y (0,04'eyl) are tetraethylated into dorofuran. Dissolve in 200℃ and cool to 0°C.
これに攪拌下１−（４−９００ベンリイル）−５−メト
中シー２−メチルインドール−３−アセチルクロリド１
５ ｆ （０，０４七ル）を滴下し、０℃で１時間、次
に室温で２時間攪拌した後、析出物を炉去しろ液を減圧
濃縮する。残渣にエーテルを加え、水、炭酸水素ナトリ
ウム水溶液及び水の順に洗浄し、無水硫酸ナトリウムで
乾燥した後エーテルを留去する。残渣をメタノールから
再結晶して、融点１４０−１４１．５°Ｃの５−［４−
（１−（４−りｏＯベンリイル）−５−メト十シー２−
メチルインドール−３−ア七ト十シ〕フェニル）−１，
１，３−トリメチルビウレット１２．５Ｆを得る（収率
５４％）。To this was added 2-methylindole-3-acetyl chloride 1 in 1-(4-900benryyl)-5-methane with stirring.
5 f (0.047 l) was added dropwise and the mixture was stirred at 0° C. for 1 hour and then at room temperature for 2 hours, and then the precipitate was removed from the oven and the filtrate was concentrated under reduced pressure. Ether is added to the residue, which is washed successively with water, an aqueous sodium bicarbonate solution, and water, dried over anhydrous sodium sulfate, and then the ether is distilled off. The residue was recrystallized from methanol to give 5-[4-
(1-(4-rioObenryl)-5-methocy2-
Methylindole-3-a7totency]phenyl)-1,
1,3-trimethylbiuret 12.5F is obtained (yield 54%).
元素分析値（Ｃ３０／／２９””４０５として）計算ｆ
ｉＩＬ（％＞：Ｃ６２，４４Ｈ５，０７＃９．７１実測
値（％）：（’６２．７Ｌ Ｈ５，０４・ ＃９．
５６実施例 ２
■−（４−９００ベン９イル）−５−メト十シー２−メ
チルインドール−３−アｔチルク０リド２．７１ （７
，２三り七ル）、５−、（４−シトロ＋ジフェニル）−
Ｃ３−ジメチルじウレット１．８ｇ（７，２三り七ル）
及び炭酸水素ナトリウム０．８４Ｆ（１０＝り七ル）を
エーテル１００ ｍｅ中に加え室温で１５時間攪拌した
後、析出物を炉夫する。Elemental analysis value (as C30//29""405) calculation f
iIL(%>:C62,44H5,07#9.71 Actual value (%): ('62.7L H5,04・#9.
56 Example 2 ■-(4-900ben9yl)-5-methocy-2-methylindole-3-atylchloride 2.71 (7
,237yl),5-,(4-citro+diphenyl)-
C3-dimethyl diuret 1.8 g (7,2 tri-7)
After adding 0.84 F (10=Li) of sodium hydrogen carbonate to 100 ml of ether and stirring at room temperature for 15 hours, the precipitate was evaporated.
ｐ液を水、炭酸水素ナトリウム水溶液及び水で順次洗浄
し、無水硫酸ナトリウムで乾燥した後、エーテルを留去
する。残渣をメタノールから再結晶して、融点８６−８
９℃の５−（−４−（１−（４−りＤ［］ベンソイル）
−５−メト＋シー２−メチルイシドール−３−アじト十
シ〕フェニル）−１，３−ジメチルじウレット８ｙを得
る（収率７１％）。The p solution is washed successively with water, an aqueous sodium bicarbonate solution, and water, dried over anhydrous sodium sulfate, and then the ether is distilled off. The residue was recrystallized from methanol to give a melting point of 86-8.
5-(-4-(1-(4-riD[]bensoyl) at 9°C
-5-Metho+cy2-methylisidole-3-azitodecy]phenyl)-1,3-dimethyldiuret 8y is obtained (yield 71%).
元素分析値（Ｃ２９Ｈ２７ＣＩＮ４０．とじて）計算値
（％）：Ｃ６１，８７Ｈ４，８３Ｈ９・９５実測値（％
）：Ｃ６１，８８Ｈ４・９０ ”９・６５（以 上
）
３７７−Elemental analysis value (C29H27CIN40.Filled) Calculated value (%): C61,87H4,83H9・95 Actual value (%)
):C61,88H4・90”9・65 (or more) 377-
Claims (1)
Ｒは低級アル↑ル基を意味する）で示されるインドール
酢酸誘導体。[Claims] ■ General formula (wherein R1 and R2 represent a hydrogen atom or a lower alkyl group,
An indole acetic acid derivative represented by R means a lower alkyl group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14515282A JPS5936660A (en) | 1982-08-20 | 1982-08-20 | Indoleacetic acid derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14515282A JPS5936660A (en) | 1982-08-20 | 1982-08-20 | Indoleacetic acid derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5936660A true JPS5936660A (en) | 1984-02-28 |
| JPH0145464B2 JPH0145464B2 (en) | 1989-10-03 |
Family
ID=15378619
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14515282A Granted JPS5936660A (en) | 1982-08-20 | 1982-08-20 | Indoleacetic acid derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5936660A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0225872A (en) * | 1988-07-14 | 1990-01-29 | Konica Corp | Toner container |
-
1982
- 1982-08-20 JP JP14515282A patent/JPS5936660A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0225872A (en) * | 1988-07-14 | 1990-01-29 | Konica Corp | Toner container |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0145464B2 (en) | 1989-10-03 |
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