JPS61212578A - 2-furanone derivative and production thereof - Google Patents
2-furanone derivative and production thereofInfo
- Publication number
- JPS61212578A JPS61212578A JP5203385A JP5203385A JPS61212578A JP S61212578 A JPS61212578 A JP S61212578A JP 5203385 A JP5203385 A JP 5203385A JP 5203385 A JP5203385 A JP 5203385A JP S61212578 A JPS61212578 A JP S61212578A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- furanone
- reaction
- organic solvent
- 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
Links
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は優れた強心作用及び抗かいよう作用を有し、医
薬として有用な新規なフラノン誘導体及びその製造方法
に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a novel furanone derivative that has excellent cardiotonic and anti-inflammatory effects and is useful as a medicine, and a method for producing the same.
（従来の技術）
本発明の２−７ラノン誘導体は文献末記載の新規化合物
である。(Prior Art) The 2-7 lanone derivative of the present invention is a novel compound described at the end of the literature.
（発明が解決しようとする問題点）
本発明の目的とするところは２−フラノン誘導体を工業
的に有利に得、優れた強心作用、抗かいよう作用を有す
る医薬を提供することである。(Problems to be Solved by the Invention) The object of the present invention is to obtain a 2-furanone derivative industrially advantageously and to provide a medicament having excellent cardiotonic and anti-inflammatory effects.
（問題点を解決するための手段）
一般式
（式中Ｘは酸素原子又は硫黄原子をＹはノ・ロゲン原子
を示す。）で表される化合物が優れた強心作用を有し、
更に抗かいよう作用も有し、しかも毒性は小さく、強心
剤、抗かいよう剤として有用であることを見い出した。(Means for solving the problem) A compound represented by the general formula (wherein,
Furthermore, it has been found that it has an anti-inflammatory effect, has low toxicity, and is useful as a cardiotonic agent and an anti-inflammatory agent.
本発明化合物は一般式
（式中Ｘは前記と同じ意味を示す。）で表される化合物
と３，４−ジハロ−５−ヒドロキシ−５Ｈ−２−フラノ
ンとを反応させることによ〕製造することができる。反
応は有機溶媒中脱水剤の存在下０℃〜室温で２〜３時間
行う。The compound of the present invention is produced by reacting a compound represented by the general formula (wherein X has the same meaning as above) with 3,4-dihalo-5-hydroxy-5H-2-furanone. be able to. The reaction is carried out in an organic solvent in the presence of a dehydrating agent at 0°C to room temperature for 2 to 3 hours.
反応終了後は反応液を水にあけ塩酸酸性とすることによ
シ目的物の粗結晶が析出する。必要ならば有機溶媒から
再結晶することによシ本発明化合物が得られる。After the reaction is completed, the reaction solution is poured into water and acidified with hydrochloric acid to precipitate crude crystals of the desired product. If necessary, the compound of the present invention can be obtained by recrystallization from an organic solvent.
（実施例） 次に実施例を挙げて本発明を更に説明する。(Example) Next, the present invention will be further explained with reference to Examples.
実施例１
〔３，４−ジクロロ−５−（２−フロイルメチル）−２
，５−ジヒドロフラン−２−オン〕（化合物Ｉ）２−ア
セチルフラン２５ｆとムコクロル酸３８ｔをメタノール
１５０艷に溶解し０℃に冷却した。Example 1 [3,4-dichloro-5-(2-furoylmethyl)-2
, 5-dihydrofuran-2-one] (Compound I) 25 f of 2-acetylfuran and 38 t of mucochloric acid were dissolved in 150 methanol and cooled to 0°C.
カセイソーダ１３．５αｆを水１００ｍ１Ｋ溶かした溶
液を２時間をかけて滴下し反応させた。滴下終了後反応
液を水にあけ塩酸酸性とし析出した結晶を炉別した。メ
タノールよシ再結晶して目的物２５ｔを得た。融点１１
０〜１１２℃
実施例２
〔３，４−ジクロロ−５−（２−テノイルメチル）−２
，５−ジヒドロフラン−２−オン〕２−アセチルチオフ
ェン１３１とムコクロル酸１７？をメタノール８０誠に
溶解しＯ’ＣＫ冷却した。カセイソーダ６１を水５０−
に溶かした溶液を２時間の間に滴下し反応させた。滴下
終了後反応液を水にあけ塩酸酸性とし析出した結晶を炉
別した。メタノールよシ再結晶して目的物１５ｆを得た
。融点９４〜９５℃
（発明の効果β：薬理作用）
次に本発明により得られた化合物の薬理活性についてそ
の代表例を記載する。A solution prepared by dissolving 13.5αf of caustic soda in 100 ml of water was added dropwise over 2 hours to cause a reaction. After the addition was completed, the reaction solution was poured into water, acidified with hydrochloric acid, and the precipitated crystals were separated in a furnace. Recrystallization from methanol yielded 25 tons of the desired product. Melting point 11
0 to 112°C Example 2 [3,4-dichloro-5-(2-tenoylmethyl)-2
, 5-dihydrofuran-2-one]2-acetylthiophene 131 and mucochloric acid 17? was dissolved in 80% methanol and cooled to O'CK. 61 parts caustic soda to 50 parts water
A solution dissolved in water was added dropwise over a period of 2 hours to cause a reaction. After the addition was completed, the reaction solution was poured into water, acidified with hydrochloric acid, and the precipitated crystals were separated in a furnace. Recrystallization from methanol gave the desired product 15f. Melting point: 94-95°C (Effect β of the invention: Pharmacological action) Next, representative examples of the pharmacological activity of the compound obtained according to the present invention will be described.
強心作用
アルシーブ アンチルナシ冒ナル ド ファル！コディ
ナミー エ ド テラピー（Ａｒｃｈ、 Ｉｎｔ。Cardiotroping Alceive Antillestic Explosive De Far! Codynamie et de therapy (Arch, Int.
Claims (2)
を示す。）で表される化合物。(1) A compound represented by the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, X represents an oxygen atom or a sulfur atom, and Y represents a halogen atom.)
化合物と３，４−ジハロ−５−ヒドロキシ−５Ｈ−２−
フラノンとを反応させることを特徴とする一般式 ▲数式、化学式、表等があります▼ （式中Ｘは前記と同じ意味を、Ｙはハロゲン原子を示す
。）で表される化合物の製造方法。(2) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, X represents an oxygen atom or a sulfur atom.) Compounds represented by the following and 3,4-dihalo-5-hydroxy-5H-2-
A method for producing a compound represented by the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, X has the same meaning as above, and Y represents a halogen atom.) characterized by reacting with a furanone.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5203385A JPS61212578A (en) | 1985-03-15 | 1985-03-15 | 2-furanone derivative and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5203385A JPS61212578A (en) | 1985-03-15 | 1985-03-15 | 2-furanone derivative and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS61212578A true JPS61212578A (en) | 1986-09-20 |
Family
ID=12903497
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5203385A Pending JPS61212578A (en) | 1985-03-15 | 1985-03-15 | 2-furanone derivative and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61212578A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5084464A (en) * | 1989-09-20 | 1992-01-28 | Kuraray Company Ltd. | Conjugated γ-hydroxybutenolide compounds and antiulcer agents containing the same as an effective ingredient |
-
1985
- 1985-03-15 JP JP5203385A patent/JPS61212578A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5084464A (en) * | 1989-09-20 | 1992-01-28 | Kuraray Company Ltd. | Conjugated γ-hydroxybutenolide compounds and antiulcer agents containing the same as an effective ingredient |
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