JPS6047264B2 - Thiazolidine derivatives - Google Patents
Thiazolidine derivativesInfo
- Publication number
- JPS6047264B2 JPS6047264B2 JP9802477A JP9802477A JPS6047264B2 JP S6047264 B2 JPS6047264 B2 JP S6047264B2 JP 9802477 A JP9802477 A JP 9802477A JP 9802477 A JP9802477 A JP 9802477A JP S6047264 B2 JPS6047264 B2 JP S6047264B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- acid
- hydrogen atom
- salt
- methylpropionyl
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
Description
【発明の詳細な説明】 本発明は、一般式(I) 〒゜ ゛←。[Detailed description of the invention] The present invention relates to general formula (I) 〒゜ ゛←.
R1SCH2CHC0選 (I) で表わされるチアゾリジン誘導体に関するものである。R1SCH2CHC0 selection (I) This relates to a thiazolidine derivative represented by
式中、R1は水素原子、アシル基(アセチル、プロピオ
ニル、ブチリル、ベンゾイルなど)またはアルキルカル
バモイル基(メチルカルバモイル、エチルカルバモイル
、プロピルカルバモイル、イソプロピルカルバモイル、
ブチルカルバモイル、イソブチルカルバモイル、ペンチ
ルカルバモイル、ヘキシルカルバモイルなど)を、R2
は1本素原子またはメチル基を、R゜は水素原子または
アルキル基(メチル、エチル、プロピル、イソプロピル
、ブチルなど)を、R4はフェニル基または置換フェニ
ル基を示し、該置換基は低級アルキル基(メチル、エチ
ル、プロピル、ブチルな・ど)、低級アルコキシ基(メ
トキシ、エトキシ、プロボキシ、ブトキシなど)、ハロ
ゲン原子またはニトロ基から選択される1個または複数
の基を示す。あるいはRa、R4はテトラメチレン、ペ
ンタメチレンなどの互いに結合してシクロアルカンフを
形成する基を示す。一般式(I)で表わされる化合物中
、R゛がアシル基またはアルキルカルバモイル基である
化合物は、一般式(■)R1SCH2CHCOOH(■
)
〔式中、R゛はアシル基またはアルキルカルバモイル基
を、R2は水素原子またはメチル基を示す。In the formula, R1 is a hydrogen atom, an acyl group (acetyl, propionyl, butyryl, benzoyl, etc.) or an alkylcarbamoyl group (methylcarbamoyl, ethylcarbamoyl, propylcarbamoyl, isopropylcarbamoyl,
butylcarbamoyl, isobutylcarbamoyl, pentylcarbamoyl, hexylcarbamoyl, etc.), R2
represents a single elementary atom or a methyl group, R° represents a hydrogen atom or an alkyl group (methyl, ethyl, propyl, isopropyl, butyl, etc.), R4 represents a phenyl group or a substituted phenyl group, and the substituent is a lower alkyl group. (methyl, ethyl, propyl, butyl, etc.), a lower alkoxy group (methoxy, ethoxy, propoxy, butoxy, etc.), a halogen atom, or a nitro group. Alternatively, Ra and R4 represent a group such as tetramethylene and pentamethylene that combine with each other to form a cycloalkampf. Among the compounds represented by the general formula (I), the compound in which R is an acyl group or an alkylcarbamoyl group has the general formula (■) R1SCH2CHCOOH (■
) [In the formula, R′ represents an acyl group or an alkylcarbamoyl group, and R2 represents a hydrogen atom or a methyl group.
〕で表わされるカルボン酸の反応性誘導体と、一般式(
■)〔式中、R3,R4は前記と同義である。] and a reactive derivative of carboxylic acid represented by the general formula (
(2) [In the formula, R3 and R4 have the same meanings as above.
〕で表わされる化合物を反応させることにより得られる
。一般式(■)の反応性誘導体としては、酸塩化物、酸
臭化物などの酸ハロゲン化物、酸無水物、アルキル炭酸
または無機ハロゲン化物(例えば、チオニルクロリド、
オキシ塩化リン、三塩化リンなど)などとの混合酸無水
物、バラニトロフェニル、ポリクロロフェニルエステル
などの活性エステルなどが挙げられる。この反応は通常
、必要に応じ、トリエチルアミン、ジメチルアニリン、
ピリジンなどの脱酸剤の存在下、メチレンクロリド、ク
ロロホルム、エーテル、ベンゼン、トルエン、ジオキサ
ン、ジメチルホルムアミドなどの不活性溶媒の存在下、
室温乃至必要に応じ加温または冷却して行われる。] can be obtained by reacting a compound represented by: Reactive derivatives of general formula (■) include acid halides such as acid chlorides and acid bromides, acid anhydrides, alkyl carbonates, and inorganic halides (for example, thionyl chloride,
Examples include mixed acid anhydrides with phosphorus oxychloride, phosphorus trichloride, etc., and active esters such as varanitrophenyl and polychlorophenyl ester. This reaction typically uses triethylamine, dimethylaniline,
In the presence of a deoxidizing agent such as pyridine, in the presence of an inert solvent such as methylene chloride, chloroform, ether, benzene, toluene, dioxane, dimethylformamide, etc.
It is carried out at room temperature or heated or cooled as necessary.
一般式(1)で表わされる化合物中、R1が水素原子で
ある化合物は、R1がアシル基またはアルキルカルバモ
イル基である化合物を加水分解することによつて容易に
得られる。反応は、水酸化ナトリウム、水酸化カリウム
、炭酸ナトリウム、炭酸カリウム、アンモニア、ヒドラ
ジンなどの塩基の存在下、水、メタノール、エタノール
などの溶媒中、室温で容易に進行する。Among the compounds represented by the general formula (1), a compound in which R1 is a hydrogen atom can be easily obtained by hydrolyzing a compound in which R1 is an acyl group or an alkylcarbamoyl group. The reaction easily proceeds at room temperature in the presence of a base such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, ammonia, or hydrazine, in a solvent such as water, methanol, or ethanol.
なお、反応は窒素気流中で行うのが望ましい。本発明に
よつて得られるチアゾリジン誘導体はIナトリウム塩、
カリウム塩、カルシウム塩などの金属塩またはジシクロ
ヘキシルアミン塩、N−メチルヘキシルアミン塩、ジエ
タノールアミン塩、N−メチルピペラジン塩、ジエチル
アミン塩、ブルシン塩などの有機塩基塩とすることがで
きる。Note that the reaction is preferably carried out in a nitrogen stream. The thiazolidine derivatives obtained by the present invention are I sodium salt,
It can be a metal salt such as potassium salt or calcium salt, or an organic base salt such as dicyclohexylamine salt, N-methylhexylamine salt, diethanolamine salt, N-methylpiperazine salt, diethylamine salt, or brucine salt.
なお、本発明によつて得られる化合物は、不斉炭素を有
するが、本発明は全ての立体異性体と包含するものであ
り、必要に応じ、常法により分割することができる。一
般式(1)の化合物およびその塩類は、すぐれた降圧作
用を有し、高血圧治療剤などの医薬として有用である。Although the compound obtained by the present invention has an asymmetric carbon, the present invention encompasses all stereoisomers and can be resolved by conventional methods if necessary. The compound of general formula (1) and its salts have an excellent antihypertensive effect and are useful as medicines such as antihypertensive agents.
実施例1
一3−アセチルチオー2−メチルプロピオン酸6.4q
を無水ベンゼン25mtに溶かし、チオニルクロリド7
.1gを加え50〜60にCで2時間攪拌する。Example 1 6.4q of 1-3-acetylthio-2-methylpropionic acid
was dissolved in 25 mt of anhydrous benzene, and thionyl chloride 7
.. Add 1g and stir at 50-60C for 2 hours.
反応液を減圧下濃縮して得られる3−アセチルチオー2
−メチルプロピオニルクロリドを、2−PO−クロロフ
ェニルー4(R)−チアゾリジンカルボン酸10.7f
1トリエチルアミン8.9yをメチレンクロリドに溶か
した溶液に、−10℃にて冷却下、加える。−8〜−5
℃にて1時間攪拌後、さらに室温で4時間攪拌する。反
応液を減圧下濃縮5し、氷冷下、へ塩酸水を加え分離し
た油状物をクロロホルムで抽出する。飽和食塩水で洗浄
、乾燥(無水硫酸マグネシウム)後、溶媒を減圧下留去
すると淡黄色油状物質が得られる。この油状物質をアセ
トン50m1に溶かし、氷冷下、ジシクロへ)キシルア
ミン8.2Vを含むアセトン溶液20m1を加え、析出
した結晶を淵取し、エタノールより再結晶すると、融点
233〜234℃(分解)の白色結晶性粉末として、3
−(3−アセチルチオー2−メチルプロピオニル)−2
−p−クロロフェニルー4!(R)−チアゾリジンカル
ボン酸ジシクロヘキシルアミン塩5.2ダが得られる。
実施例2
3−エチルカルバモイルチオプロピオン酸5.3yを無
水ベンゼン25m1に溶かし、チオニルクロリド5.4
′を加え40〜45℃て30分攪拌する。3-acetylthio 2 obtained by concentrating the reaction solution under reduced pressure
-Methylpropionyl chloride, 2-PO-chlorophenyl-4(R)-thiazolidinecarboxylic acid 10.7f
1 To a solution of 8.9y of triethylamine dissolved in methylene chloride is added under cooling at -10°C. -8 to -5
After stirring at ℃ for 1 hour, the mixture is further stirred at room temperature for 4 hours. The reaction solution was concentrated under reduced pressure (5), hydrochloric acid water was added thereto under ice cooling, and the separated oil was extracted with chloroform. After washing with saturated brine and drying (anhydrous magnesium sulfate), the solvent is distilled off under reduced pressure to obtain a pale yellow oil. Dissolve this oily substance in 50 ml of acetone, add 20 ml of acetone solution containing 8.2 V of xylamine under ice cooling, add 20 ml of acetone solution containing 8.2 V of xylamine, filter out the precipitated crystals, and recrystallize from ethanol, melting point 233-234°C (decomposition). as a white crystalline powder of 3
-(3-acetylthio-2-methylpropionyl)-2
-p-chlorophenyl-4! 5.2 da of (R)-thiazolidinecarboxylic acid dicyclohexylamine salt is obtained.
Example 2 5.3y of 3-ethylcarbamoylthiopropionic acid was dissolved in 25ml of anhydrous benzene, and 5.4y of thionyl chloride was dissolved.
' and stirred at 40-45°C for 30 minutes.
反応液を減圧下濃縮して得られる3−エチルカルバモイ
ルチオプロピオニルクロリドを、2−p−トリルー4(
R)−チアゾリジンカルボン酸5.7y1トリエチルア
ミン6.1qをメチレンクロリドに溶かした溶液に、−
10℃にて冷却下、加える。−8〜−5℃にて1時間攪
拌後、さらに室温で4時間攪拌する。反応液を減圧下濃
縮し、氷冷下、へ塩酸水を加え分離した油状物をクロロ
ホルムで抽出する。飽和食塩水で洗浄、乾燥(無水マグ
ネシウム)後、溶媒を減圧下留去して得られる油状物を
、シリカゲルクロマトにてクロロホルム−メタノールの
展開混合溶媒によつて精製すると、淡黄色油状物質とし
て、3−エチルカルバモイルチオプロピオニルー2−p
−トリルー4(R)−チアゾリジンカルボン酸3.8g
が得られる。赤外線吸収スペクトル νMaxcm−1
1630,1690,1760(カルボン酸、アミド)
核磁気共鳴スペクトル δ(CDCl3中)1.6(3
H1三重線、CH3CH2NH−) 55.05
(1H、三重線、4位の水素原子)実施例3窒素気流中
、へ水酸化ナトリウム溶液50m1に、3−(3−アセ
チルチオー2−メチルプロピオニル)−2−p−クロロ
フェニルー4−(R)1(ーチアゾリジンカルボン酸6
qを徐々に加え、室温で2時間攪拌する。3-ethylcarbamoylthiopropionyl chloride obtained by concentrating the reaction solution under reduced pressure was mixed with 2-p-tolylu-4(
R)-thiazolidinecarboxylic acid 5.7y1 triethylamine 6.1q dissolved in methylene chloride, -
Add while cooling at 10°C. After stirring at -8 to -5°C for 1 hour, the mixture is further stirred at room temperature for 4 hours. The reaction solution was concentrated under reduced pressure, and hydrochloric acid water was added thereto under ice cooling, and the separated oil was extracted with chloroform. After washing with saturated brine and drying (anhydrous magnesium), the solvent was distilled off under reduced pressure, and the resulting oil was purified with silica gel chromatography using a chloroform-methanol mixed solvent to give a pale yellow oil. 3-ethylcarbamoylthiopropionyl-2-p
-Trilu-4(R)-thiazolidinecarboxylic acid 3.8g
is obtained. Infrared absorption spectrum νMaxcm-1
1630, 1690, 1760 (carboxylic acid, amide)
Nuclear magnetic resonance spectrum δ (in CDCl3) 1.6 (3
H1 triplet, CH3CH2NH-) 55.05
(1H, triple line, hydrogen atom at position 4) Example 3 In a nitrogen stream, 3-(3-acetylthio-2-methylpropionyl)-2-p-chlorophenyl-4-(R) was added to 50 ml of sodium hydroxide solution. 1 (-thiazolidinecarboxylic acid 6
Add q gradually and stir at room temperature for 2 hours.
氷冷下、30%硫酸水30TT1tを加え、分離する油
状物をエーテルで抽出する。飽和食塩水で洗浄、乾燥(
無水硫酸マグネシウム)後、溶媒を減圧下留去すると結
晶か析出してく1.る。この結晶を酢酸エチルとn−ヘ
キサンとの混合溶媒から再結晶すると、融点100〜1
03゜Cの白色結晶性粉末として、2−p−クロロフェ
ニルー3一(3−メルカプトー2−メチルプロピオニル
)−4(R)−チアゾリジンカルボン酸3yが得ら2れ
る。実施例4
窒素気流中、3−エチルカルバモイルチオプロピオニル
ー2−p−トリルー4(R)−チアゾリジンカルボン酸
3.8ダを溶かしたメタノール溶液235mLに、4N
水酸化ナトリウム溶液9m1を徐々に加え、室温て1.
5I寺間攪拌する。Under ice-cooling, 30 TT of 30% sulfuric acid water is added, and the oily substance that separates is extracted with ether. Wash with saturated saline and dry (
After (anhydrous magnesium sulfate), the solvent is distilled off under reduced pressure to precipitate crystals.1. Ru. When this crystal is recrystallized from a mixed solvent of ethyl acetate and n-hexane, it has a melting point of 100-1
2-p-chlorophenyl-3-(3-mercapto-2-methylpropionyl)-4(R)-thiazolidinecarboxylic acid 3y is obtained as a white crystalline powder at 0.03°C. Example 4 In a nitrogen stream, 4 N
Gradually add 9 ml of sodium hydroxide solution and leave at room temperature for 1.
5I Terama stir.
氷冷下、希塩酸を加えPH3以下とし、分離する油状物
を食塩て飽和後、エーテルで抽出する。飽和食塩水で洗
浄、乾燥(無水硫酸マグネシウム)後、溶媒を減圧下!
濃縮して得られる油状物を、シリカゲルクロマトにてク
ロロホルム−メタノールの展開混合溶媒によつて精製す
ると、淡黄色油状物質として、3一(3−メルカプトフ
狛ピオニル)−2−p−トリルー4(R)−チアゾリジ
ンカルボン酸1.6gが.得られる。赤外線吸収スペク
トル νMaxcm−11610,1740(カルボン
酸、アミド)核磁気共鳴スペクトル δ(CDCl3中
)1.64(IHl三重線、.US−)5.04(1H
、三重線、4位の水素原子)実施例1あるいは実施例2
と同様にして、さらにたとえば次の化合物が得られる。Under ice-cooling, dilute hydrochloric acid is added to bring the pH to below 3, and the oily substance that separates is saturated with sodium chloride, and then extracted with ether. After washing with saturated saline and drying (anhydrous magnesium sulfate), remove the solvent under reduced pressure!
The oily substance obtained by concentration is purified by silica gel chromatography using a developing mixed solvent of chloroform-methanol to obtain 3-(3-mercaptov-koma-pionyl)-2-p-trilu-4(R) as a pale yellow oily substance. )-thiazolidinecarboxylic acid 1.6g. can get. Infrared absorption spectrum νMaxcm-11610, 1740 (carboxylic acid, amide) Nuclear magnetic resonance spectrum δ (in CDCl3) 1.64 (IHl triplet, .US-) 5.04 (1H
, triple line, hydrogen atom at position 4) Example 1 or Example 2
Similarly, for example, the following compounds can be obtained.
◎3−(3−アセチルチオー2−メチルプロピオニル)
−2−(2,4−ジクロロフェニル)一4(R)−チア
ゾリジンカルボン酸ジシクロヘキシルアミン塩 白色結
晶性粉末 融点230〜234℃(分解点)。◎3-(3-acetylthio 2-methylpropionyl)
-2-(2,4-dichlorophenyl)-4(R)-thiazolidinecarboxylic acid dicyclohexylamine salt White crystalline powder Melting point 230-234°C (decomposition point).
)3−(3−アセチルチオー2−メチルプロピオニル)
−2−p−メトキシフェニルー4(R)−チアゾリジン
カルボゾ酸。)3-(3-acetylthio-2-methylpropionyl)
-2-p-methoxyphenyl-4(R)-thiazolidinecarbozoic acid.
赤外線吸収スペクトルVmaxCF?t−11610,
1690,1745(カルボン酸、アミド)核磁気共鳴
スペクトル δ(CDCl3中)3.8(3N1一重線
、CH3O−)5.0(1H14位水素原子)
A3−(3−アセチルチオー2−メチルプロピオニル)
−2−フェニルー4(R)−チアゾリジンカルボン酸ブ
ルシン塩 白色結晶性粉末融点122〜123℃。Infrared absorption spectrum VmaxCF? t-11610,
1690,1745 (carboxylic acid, amide) nuclear magnetic resonance spectrum δ (in CDCl3) 3.8 (3N1 singlet, CH3O-) 5.0 (1H14-position hydrogen atom) A3- (3-acetylthio-2-methylpropionyl)
-2-Phenyl-4(R)-thiazolidinecarboxylic acid brucine salt White crystalline powder, melting point 122-123°C.
)3−(3−アセチルチオー2−メチルプロピオニル)
−2−p−ニトロフェニルー4(R)−チアゾリジンカ
ルボン酸。)3-(3-acetylthio-2-methylpropionyl)
-2-p-nitrophenyl-4(R)-thiazolidinecarboxylic acid.
D3−(3−アセチルチオー2−メチルプロピオニル)
−2−メチルー2−フェニルー4(R)−チアゾリジン
カルボン酸。D3-(3-acetylthio 2-methylpropionyl)
-2-Methyl-2-phenyl-4(R)-thiazolidinecarboxylic acid.
◎3−(3−エチルカルバモイルチオプロピオニル)−
2−フェニルー4(R)−チアゾ”リジンカルボン酸。◎3-(3-ethylcarbamoylthiopropionyl)-
2-Phenyl-4(R)-thiazo"lysinecarboxylic acid.
実施例3あるいは実施例4と同様にして、さらにたとえ
ば次の化合物が得られる。◎3−(3−メルカプトー2
−メチルプロピオニル)−2−p−メトキシフェニルー
4(R)ーチアゾリジンカルボン酸 白色結晶性粉末融
点152〜154℃。In the same manner as in Example 3 or 4, for example, the following compound is obtained. ◎3-(3-mercapto 2
-Methylpropionyl)-2-p-methoxyphenyl-4(R)-thiazolidinecarboxylic acid White crystalline powder, melting point 152-154°C.
◎2−(2,4−ジクロロフェニル)−3−(3−メル
カプトー2−メチルフ0ロピオニル)−4(R)−チア
ゾリジンカルボン酸ジシクロヘキシルアミン塩 白色結
晶性粉末 融点200〜203アC0◎3−(3−メル
カプトー2−メチルプロピオニル)−2−フェニルー4
(R)−チアゾリジンカルボン酸N。◎2-(2,4-dichlorophenyl)-3-(3-mercapto-2-methylfluoropionyl)-4(R)-thiazolidinecarboxylic acid dicyclohexylamine salt White crystalline powder Melting point 200-203ACO◎3-(3 -mercapto-2-methylpropionyl)-2-phenyl-4
(R)-thiazolidinecarboxylic acid N.
;1.5795(25ゾC)。赤外線吸収スペクトル
νMaxcm−11610,1740(カルボン酸、ア
ミド)核磁気共鳴スペクトル δ(CDCl3中)1.
56(1H1三重線、US−)◎3−(3−メルカプト
ー2−メチルプロビオニル)−2−p−ニトロフェニル
ー4(R)ーチアゾリジンカルボン酸。;1.5795 (25zoC). Infrared absorption spectrum
νMaxcm-11610,1740 (carboxylic acid, amide) nuclear magnetic resonance spectrum δ (in CDCl3) 1.
56 (1H1 triplet, US-) 3-(3-mercapto-2-methylprobionyl)-2-p-nitrophenyl-4(R)-thiazolidinecarboxylic acid.
03−(3−メルカプトー2−メチルプロピオニル)−
2−メチルー2−フェニルー4(R)−チアゾリジンカ
ルボン酸。03-(3-mercapto 2-methylpropionyl)-
2-Methyl-2-phenyl-4(R)-thiazolidinecarboxylic acid.
@3−(3−メルカプトー2−メチルプロピオニル)−
2−p−トリルー4(R)−チアゾリジンカルボン酸。@3-(3-mercapto 2-methylpropionyl)-
2-p-Tolylu-4(R)-thiazolidinecarboxylic acid.
@3−(3−メルカプトプロピオニル)−2−フェニル
ー4(R)−チアゾリジンカルボン酸。)3−(3−メ
ルカプトプロピオニル)−2ーメチルー2−フェニルー
4(R)−チアゾリジンカルボン酸。@3-(3-mercaptopropionyl)-2-phenyl-4(R)-thiazolidinecarboxylic acid. ) 3-(3-mercaptopropionyl)-2-methyl-2-phenyl-4(R)-thiazolidinecarboxylic acid.
)4−(3−メルカプトー2−メチルプロピオニル)−
1−チアー4−アザスピロ〔4,5〕デカンー3(R)
一カルボン酸 白色結晶性粉末 融点175〜178ボ
C0)4−(3−アセチルチオー2−メチルプロピオニ
ル)−1−チアー4−アザスピロ〔4,5〕デカンー3
(R)一カルボン酸 白色結晶性粉末 融点165〜1
68℃。)4-(3-mercapto-2-methylpropionyl)-
1-thia 4-azaspiro[4,5]decane-3(R)
Monocarboxylic acid White crystalline powder Melting point 175-178 Bo) 4-(3-acetylthio-2-methylpropionyl)-1-thia 4-azaspiro[4,5]decane-3
(R) Monocarboxylic acid White crystalline powder Melting point 165-1
68℃.
Claims (1)
ルバモイル基を、R^2は水素原子またはメチル基を、
R^3は水素原子またはアルキル基を、R^4はフェニ
ル基または置換フェニル基を示し、該置換基は低級アル
キル基、低級アルコキシ基、ハロゲン原子またはニトロ
基から選択される1個または複数の基を示す。 あるいはR^3とR^4は互いに結合したシクロアルカ
ンを形成する基を示す。[Claims] 1. A thiazolidine derivative or a salt thereof represented by the general formula ▲ Numerical formula, chemical formula, table, etc. ▼. [In the formula, R^1 is a hydrogen atom, an acyl group or an alkylcarbamoyl group, R^2 is a hydrogen atom or a methyl group,
R^3 represents a hydrogen atom or an alkyl group, R^4 represents a phenyl group or a substituted phenyl group, and the substituent is one or more selected from a lower alkyl group, a lower alkoxy group, a halogen atom, or a nitro group. Indicates the group. Alternatively, R^3 and R^4 represent groups bonded to each other to form a cycloalkane.
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP9802477A JPS6047264B2 (en) | 1977-08-15 | 1977-08-15 | Thiazolidine derivatives |
IT50037/78A IT1105731B (en) | 1977-06-29 | 1978-06-27 | THIAZOLIDINE COMPOUNDS |
FR7819125A FR2395998A1 (en) | 1977-06-29 | 1978-06-27 | NEW THIAZOLIDINE DERIVATIVES AND THEIR APPLICATION IN THE TREATMENT OF HYPERTENSION |
ES471239A ES471239A1 (en) | 1977-06-29 | 1978-06-28 | Thiazolidine compounds |
GB7828177A GB2000508B (en) | 1977-06-29 | 1978-06-28 | Thiazolidine compounds |
SE7807335A SE434836B (en) | 1977-06-29 | 1978-06-28 | thiazolidine |
AT0472378A AT379591B (en) | 1977-08-15 | 1978-06-29 | METHOD FOR PRODUCING NEW THIAZOLIDE DERIVATIVES AND THEIR SALTS AND ISOMERS |
NL7807023A NL7807023A (en) | 1977-06-29 | 1978-06-29 | NEW THIAZOLIDINS, PREPARATIONS CONTAINING THEM AND METHODS FOR PREPARING THEM. |
DE2828578A DE2828578C2 (en) | 1977-06-29 | 1978-06-29 | Thiazolidines, their manufacture and use |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP9802477A JPS6047264B2 (en) | 1977-08-15 | 1977-08-15 | Thiazolidine derivatives |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5432466A JPS5432466A (en) | 1979-03-09 |
JPS6047264B2 true JPS6047264B2 (en) | 1985-10-21 |
Family
ID=14208341
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP9802477A Expired JPS6047264B2 (en) | 1977-06-29 | 1977-08-15 | Thiazolidine derivatives |
Country Status (2)
Country | Link |
---|---|
JP (1) | JPS6047264B2 (en) |
AT (1) | AT379591B (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU528115B2 (en) * | 1978-04-08 | 1983-04-14 | Santen Pharmaceutical Co. Ltd. | Antihypertensive 4-thiazolidine/carboxylic acids |
JPS565415A (en) * | 1979-06-26 | 1981-01-20 | Santen Pharmaceut Co Ltd | Ester-type hypotensor |
JPS55124757A (en) * | 1979-03-17 | 1980-09-26 | Santen Pharmaceut Co Ltd | Sulfur-containing compound |
JPS57112381A (en) * | 1980-12-29 | 1982-07-13 | Santen Pharmaceut Co Ltd | Five-membered heterocyclic compound |
-
1977
- 1977-08-15 JP JP9802477A patent/JPS6047264B2/en not_active Expired
-
1978
- 1978-06-29 AT AT0472378A patent/AT379591B/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
AT379591B (en) | 1986-01-27 |
JPS5432466A (en) | 1979-03-09 |
ATA472378A (en) | 1981-04-15 |
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