JPS6127984A - Phodanineacetic acid derivative - Google Patents

Phodanineacetic acid derivative

Info

Publication number
JPS6127984A
JPS6127984A JP14817284A JP14817284A JPS6127984A JP S6127984 A JPS6127984 A JP S6127984A JP 14817284 A JP14817284 A JP 14817284A JP 14817284 A JP14817284 A JP 14817284A JP S6127984 A JPS6127984 A JP S6127984A
Authority
JP
Japan
Prior art keywords
formula
acetic acid
rhodanine
methyl
acid derivative
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
Application number
JP14817284A
Other languages
Japanese (ja)
Other versions
JPH0566391B2 (en
Inventor
Takatsugu Honna
隆次 本那
Kazuo Ogawa
和男 小川
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Taiho Pharmaceutical Co Ltd
Original Assignee
Taiho Pharmaceutical Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Taiho Pharmaceutical Co Ltd filed Critical Taiho Pharmaceutical Co Ltd
Priority to JP14817284A priority Critical patent/JPS6127984A/en
Publication of JPS6127984A publication Critical patent/JPS6127984A/en
Publication of JPH0566391B2 publication Critical patent/JPH0566391B2/ja
Granted legal-status Critical Current

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  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

NEW MATERIAL:A compound expressed by formula I (R is lower alkyl). EXAMPLE:5-(3-Methyl-5-isoxazolylmethylene)rhodanine-3-acetic acid. USE:A drug for diabetes. PREPARATION:For example, a compound expressed by formula II or an alkali salt thereof, e.g. 5-(3-methyl-5-isoxazolylmethylene)rhodanine-3-acetic acid, is reduced in the presence of a Pd/C catalyst preferably in an aqueous solvent under ordinary pressure -10atm hydrogen pressure at room temperature. The starting material is novel, and obtained by for example reacting a compound expressed by formula III, e.g. 3-methylisoxazole-5-aldehyde, with rhodanine-3-acetic acid expressed by formula IV.

Description

【発明の詳細な説明】 ［産業上の利用分野］ 本発明のローダニン酢酸誘導体は新規化合物であり、医
薬として有用である。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The rhodanine acetic acid derivative of the present invention is a new compound and is useful as a medicine.

［発明の構成及び効果コ 本発明は下記一般式（１）で示される新規なローダニン
酢酸誘導体に関する。[Structure and Effects of the Invention] The present invention relates to a novel rhodanine acetic acid derivative represented by the following general formula (1).

（式中、Ｒは低級アルキル基を意味する。）上記一般式
（１）において、Ｒで定義される低級アルキル基として
は、例えばメチル、エチル、プロピル、イソプロピル、
ブチル基等が挙げられる。(In the formula, R means a lower alkyl group.) In the above general formula (1), the lower alkyl group defined by R includes, for example, methyl, ethyl, propyl, isopropyl,
Examples include butyl group.

本発明の上記化合物は文献未記載の新規化合物であって
、血糖降下作用、脂質低下作用、アルドース・リダクタ
ーゼ阻害作用等を有し、糖尿病用剤として有用なもので
ある。The above-mentioned compound of the present invention is a novel compound that has not been described in any literature, and has hypoglycemic action, lipid-lowering action, aldose reductase inhibiting action, etc., and is useful as an agent for diabetes.

本発明に係る前記一般式（１）で示されるローダニン酢
酸誘導体は、例えば一般式（２）で示される化合物を還
元することにより製造することができる。The rhodanine acetic acid derivative represented by the general formula (1) according to the present invention can be produced, for example, by reducing the compound represented by the general formula (2).

（式中、Ｒは前記に同じ） 上式の還元反応は通常、液相中、常圧〜ｌＯ気圧程度に
おいて行われる。溶媒としては、反応に悪影響を及ぼさ
ないものであれば特に限定されないが、通常水が好適で
ある。尚、一般式（２）で示される化合物が水にＳ溶性
の場合には、アルカリ塩等とすることにより、還元する
のが有利である。還元反応は一般に水素圧が高いほど有
利であるが、通常、常圧〜１０気圧程度で十分に反応は
進行する。温度は適宜選択することができるが、通常１
０〜５０℃、好ましくは室温付近で行われる。触媒とし
ては一般に白金、パラジウム、ニッケル等が用いられる
が、パラジウム触媒が好適である。上記の反応により、
本発明化合物（１）が生成し、これは通常の分離手段に
より容易に単離可能である。(In the formula, R is the same as above.) The reduction reaction in the above formula is usually carried out in a liquid phase at about normal pressure to 100 atm. The solvent is not particularly limited as long as it does not adversely affect the reaction, but water is usually preferred. In addition, when the compound represented by general formula (2) is S-soluble in water, it is advantageous to reduce it by converting it into an alkali salt or the like. Generally, the higher the hydrogen pressure, the more advantageous the reduction reaction is, but the reaction usually proceeds sufficiently at normal pressure to about 10 atm. The temperature can be selected as appropriate, but usually 1
It is carried out at 0 to 50°C, preferably around room temperature. As a catalyst, platinum, palladium, nickel, etc. are generally used, and a palladium catalyst is preferred. Due to the above reaction,
Compound (1) of the present invention is produced, which can be easily isolated by conventional separation means.

尚、出発原料となる一般式（２）で示される化合物は新
規化合物であり、例えば一般式（３）で示されるアルデ
ヒドとローダニン酢酸（４）とを公知の方法［Ｆｉｓｃ
ｈｅｒ、Ｅ、Ｈ，＋Ｈｉｂｂｅｒｔ＋ｌｌ’、、Ｊ、Ａ
ｍ、Ｃｈｅｍ、ｓｏｃ、、６９，１２０８　（１９４７
）］に準じて（式中、Ｒは前記に同じ） 反応させることにより容易に製造することができる。次
に参考例及び実施例を挙げて本発明を具体的に説明する
。The compound represented by the general formula (2) as a starting material is a new compound. For example, the aldehyde represented by the general formula (3) and rhodanine acetic acid (4) are prepared by a known method [Fisc.
her,E,H,+Hibbert+ll',,J,A
m, Chem, soc, 69, 1208 (1947
)] (wherein R is the same as above). Next, the present invention will be specifically explained with reference to reference examples and examples.

参考例１゜ ３−メチルイソキサゾール−５−アルデヒド３．２ｇ、
ローダニン−３−酢酸５．６ｇ、酢酸ナトリウム２．９
ｇを無水酢酸３０ｍ１中に加え、１３０〜１５０℃に３
０分間加熱攪拌したのち、氷水中に注加する。析出物を
濾取し、ジメチルホルムアミドから再結晶すると融点２
８０〜２８３℃（分解）の５−（３−メチル−５−イソ
キサゾリルメチレン）ローダニン−３−酢酸４．０ｇが
得られる（収率４８．８％）。Reference example 1 3.2 g of 3-methylisoxazole-5-aldehyde,
Rhodanine-3-acetic acid 5.6g, sodium acetate 2.9
g in 30 ml of acetic anhydride and heated to 130-150℃ for 3 hours.
After heating and stirring for 0 minutes, the mixture was poured into ice water. When the precipitate is filtered and recrystallized from dimethylformamide, the melting point is 2.
4.0 g of 5-(3-methyl-5-isoxazolylmethylene)rhodanine-3-acetic acid at 80-283°C (decomposition) is obtained (yield 48.8%).

元素分析（Ｃ，０ＨｅＮ２０４Ｓ２・Ｈ２Ｏとして）Ｃ
ＨＮ 計算値（％）３９．７２　３．３３　９．２７実測値（
％）３９．０Ｂ　　３．２４　８．８８実施例１ ５−（３−メチル−５−インキサゾリルメチレン）ロー
ダニン−３−酢酸２６０ｇ、炭酸′水素ナトリウム１．
０ｇを水１００ｍ１に溶解し、１０％パラジウム炭素１
６０ｇを加えて、室温、水素圧３気圧下で還元する。反
応後、触媒を濾去し、濾液に希塩酸を加えてＰＨ１とす
る。析出物を濾取し、水から再結晶すると融点２３５〜
２４０℃（分解）の５−（３−メチル−５−イソキサゾ
リルメチル）ローダニン−３−酢酸０．６ｇが得られる
（収率３ｏ％）。Elemental analysis (as C,0HeN204S2・H2O)C
HN Calculated value (%) 39.72 3.33 9.27 Actual value (
%) 39.0B 3.24 8.88 Example 1 260 g of 5-(3-methyl-5-inxazolylmethylene)rhodanine-3-acetic acid, sodium bicarbonate 1.
Dissolve 0 g in 100 ml of water, add 10% palladium on carbon 1
Add 60 g and reduce at room temperature under 3 atmospheres of hydrogen pressure. After the reaction, the catalyst is removed by filtration, and dilute hydrochloric acid is added to the filtrate to adjust the pH to 1. When the precipitate is filtered and recrystallized from water, the melting point is 235 ~
0.6 g of 5-(3-methyl-5-isoxazolylmethyl)rhodanine-3-acetic acid at 240°C (decomposition) is obtained (yield: 30%).

元素分析　（Ｃ＋　ＯＨＩ　０Ｎ２０４Ｓ２として）Ｃ
ＨＮ 計算値（％）４１．９５　３．５２　９．７８実測値（
％）４１．’　３３　３．２５　９．５７（以上）Elemental analysis (as C+ OHI 0N204S2)C
HN Calculated value (%) 41.95 3.52 9.78 Actual value (
%)41. ' 33 3.25 9.57 (or more)

Claims (1)

【特許請求の範囲】[Claims] （１）一般式 ▲数式、化学式、表等があります▼ （式中、Ｒは低級アルキル基を意味する。）で示される
ローダニン酢酸誘導体。(1) Rhodanine acetic acid derivative represented by the general formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R means a lower alkyl group.)
JP14817284A 1984-07-16 1984-07-16 Phodanineacetic acid derivative Granted JPS6127984A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP14817284A JPS6127984A (en) 1984-07-16 1984-07-16 Phodanineacetic acid derivative

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP14817284A JPS6127984A (en) 1984-07-16 1984-07-16 Phodanineacetic acid derivative

Publications (2)

Publication Number Publication Date
JPS6127984A true JPS6127984A (en) 1986-02-07
JPH0566391B2 JPH0566391B2 (en) 1993-09-21

Family

ID=15446855

Family Applications (1)

Application Number Title Priority Date Filing Date
JP14817284A Granted JPS6127984A (en) 1984-07-16 1984-07-16 Phodanineacetic acid derivative

Country Status (1)

Country Link
JP (1) JPS6127984A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0208040A2 (en) * 1985-07-10 1987-01-14 Taiho Pharmaceutical Company Limited Rhodanine derivatives and a process for preparing same
JPS62238286A (en) * 1986-04-08 1987-10-19 Taiho Yakuhin Kogyo Kk Tetrazole derivative
KR100844131B1 (en) 2007-01-03 2008-07-04 한국화학연구원 Anticancer drug comprising rhodanine derivatives or their pharmaceutically acceptable salts

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5430171A (en) * 1977-08-10 1979-03-06 Taiho Pharmaceutical Co Ltd Isooxazole derivative and production

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5430171A (en) * 1977-08-10 1979-03-06 Taiho Pharmaceutical Co Ltd Isooxazole derivative and production

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0208040A2 (en) * 1985-07-10 1987-01-14 Taiho Pharmaceutical Company Limited Rhodanine derivatives and a process for preparing same
US4714765A (en) * 1985-07-10 1987-12-22 Taiho Pharmaceutical Company, Limited Rhodanine derivatives and process for preparing the same
US4777259A (en) * 1985-07-10 1988-10-11 Taiho Pharmaceutical Company Limited Rhodanine derivatives and process for preparing the same
JPS62238286A (en) * 1986-04-08 1987-10-19 Taiho Yakuhin Kogyo Kk Tetrazole derivative
JPH0580479B2 (en) * 1986-04-08 1993-11-09 Taiho Pharmaceutical Co Ltd
KR100844131B1 (en) 2007-01-03 2008-07-04 한국화학연구원 Anticancer drug comprising rhodanine derivatives or their pharmaceutically acceptable salts

Also Published As

Publication number Publication date
JPH0566391B2 (en) 1993-09-21

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