JPH0977751A - Process for producing N-unsubstituted isoxazolidine - Google Patents

Process for producing N-unsubstituted isoxazolidine

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Publication number
JPH0977751A
JPH0977751A JP7234126A JP23412695A JPH0977751A JP H0977751 A JPH0977751 A JP H0977751A JP 7234126 A JP7234126 A JP 7234126A JP 23412695 A JP23412695 A JP 23412695A JP H0977751 A JPH0977751 A JP H0977751A
Authority
JP
Japan
Prior art keywords
formula
group
substituent
unsubstituted
represented
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
Application number
JP7234126A
Other languages
Japanese (ja)
Inventor
Atsushi Abiko
淳 安孫子
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.)
Kao Corp
Original Assignee
Kao Corp
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 Kao Corp filed Critical Kao Corp
Priority to JP7234126A priority Critical patent/JPH0977751A/en
Publication of JPH0977751A publication Critical patent/JPH0977751A/en
Pending legal-status Critical Current

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Classifications

    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

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  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

(57)【要約】 【解決手段】 次の反応式に従う、Ｎ−無置換イソオキ
サゾリジンの製造法。 【化１】 【効果】 本発明によればアルデヒドとω−ヒドロキシ
オキシムとの反応が低温かつ短時間で終了するので、副
反応が少なく、高収率で、かつ広範囲のＮ−無置換イソ
オキサゾリジン類が得られる。(57) Abstract: A method for producing an N-unsubstituted isoxazolidine according to the following reaction formula. Embedded image [Effects] According to the present invention, since the reaction between an aldehyde and ω-hydroxyoxime is completed at a low temperature and in a short time, side reactions are few, a high yield and a wide range of N-unsubstituted isoxazolidines can be obtained. .

Description

【発明の詳細な説明】Detailed Description of the Invention

【０００１】[0001]

【発明の属する技術分野】本発明は医薬品、農薬、化粧
品等の原料として有用なＮ−無置換イソオキサゾリジン
の製造法に関する。TECHNICAL FIELD The present invention relates to a process for producing an N-unsubstituted isoxazolidine useful as a raw material for medicines, agricultural chemicals, cosmetics and the like.

【０００２】[0002]

【従来の技術】Ｎ−無置換イソオキサゾリジンは医薬
品、農薬、化粧品等の原料となる有用な基本母核ヘテロ
環である。その製造法としては、（１）オキシムの互変
異性化を利用したニトロン−オレフィンの環化付加反応
を利用した方法；（２）イソオキサゾリンのＣ＝Ｎ二重
結合へのヒドリド又はアルキル求核剤の付加反応；
（３）不活性溶媒中の加熱による、ω−ヒドロキシオキ
シムとアルデヒドの縮合によるＮ−環状アセタール置換
ニトロンの生成とオレフィンの環化付加、さらに、それ
に引き続く酸加水分解による方法、が知られている。2. Description of the Related Art N-Unsubstituted isoxazolidine is a useful basic nucleus heterocycle as a raw material for medicines, agricultural chemicals, cosmetics and the like. As its production method, (1) a method utilizing a nitrone-olefin cycloaddition reaction utilizing tautomerization of an oxime; (2) a hydride or an alkyl nucleophile to a C = N double bond of isoxazoline. Addition reaction of agents;
(3) A method is known in which an N-cyclic acetal-substituted nitrone is produced by condensation of ω-hydroxyoxime and an aldehyde by heating in an inert solvent, cycloaddition of an olefin, and subsequent acid hydrolysis is performed. .

【０００３】しかしながら、上記（１）及び（２）の方
法は、適用できる系が限られていて一般性がない。また
（３）の方法は（１）、（２）の方法に比べて適用範囲
は広いが、高温での長時間加熱が必要であり、副反応の
制御が問題となっていた。However, the methods (1) and (2) are not general because the applicable systems are limited. Further, the method (3) has a wider application range than the methods (1) and (2), but requires heating at a high temperature for a long time, which causes a problem of side reaction control.

【０００４】[0004]

【発明が解決しようとする課題】従って、本発明の目的
は短時間の反応で高収率で得られ、かつ適用範囲の広い
Ｎ−無置換イソオキサゾリジンの製造法を提供すること
にある。SUMMARY OF THE INVENTION It is, therefore, an object of the present invention to provide a method for producing an N-unsubstituted isoxazolidine which can be obtained in a high yield in a short reaction time and has a wide range of applications.

【０００５】[0005]

【課題を解決するための手段】そこで本発明者らは上記
（３）の方法に着目して検討したところ、触媒として有
機スズ化合物を用いれば、短時間、高収率でω−ヒドロ
キシオキシムとアルデヒドとの縮合によりＮ−環状アセ
タール置換ニトロンが生成し、これにオレフィンを反応
させて閉環後加水分解すれば、広い一般性を持って、Ｎ
−無置換イソオキサゾリジンが得られることを見出し、
本発明を完成するに至った。Then, the inventors of the present invention have conducted an examination focusing on the above method (3). When an organotin compound is used as a catalyst, ω-hydroxyoxime is produced in a short time in a high yield. N-cyclic acetal-substituted nitrones are produced by condensation with aldehydes, and if they are reacted with olefins to undergo ring-closing and then hydrolysis, N-cyclic compounds have a wide generality.
-Finding that an unsubstituted isoxazolidine is obtained,
The present invention has been completed.

【０００６】本発明は次の反応式で表される。The present invention is represented by the following reaction formula.

【０００７】[0007]

【化７】 [Chemical 7]

【０００８】（式中、Ｒ1 は置換基を有していてもよい
芳香族基又は置換基を有していてもよい脂肪族基を示
し、Ｒ2 は水素原子を有していてもよい直鎖又は分岐鎖
のアルキレン基を示し、Ｒ3、Ｒ4、Ｒ5 及びＲ6 はそれ
ぞれ水素原子又は有機基を示し、Ｒ1a、Ｒ3a、Ｒ4a、Ｒ
5a及びＲ6aはそれぞれＲ1、Ｒ3、Ｒ4 、Ｒ5 及びＲ6 を
示すか又はこれらの基が加水分解を受けて生じる基もし
くは水素原子を示す）(In the formula, R 1 represents an aromatic group which may have a substituent or an aliphatic group which may have a substituent, and R 2 may have a hydrogen atom. A linear or branched alkylene group is shown, R 3 , R 4 , R 5 and R 6 are each a hydrogen atom or an organic group, and R 1a , R 3a , R 4a , R
5a and R 6a each represent R 1 , R 3 , R 4 , R 5 and R 6 or a group or a hydrogen atom formed by hydrolysis of these groups)

【０００９】すなわち、本発明は式（１）で表されるア
ルデヒド類に式（２）で表されるω−ヒドロキシオキシ
ムを有機スズ化合物の存在下に反応させ、得られた式
（３）で表されるＮ−環状アセタール置換ニトロンに式
（４）で表されるオレフィン類を反応させ、次いで得ら
れた式（５）で表される化合物を加水分解することを特
徴とする式（６）で表されるＮ−無置換イソオキサゾリ
ジンの製造法を提供するものである。That is, according to the present invention, the aldehyde represented by the formula (1) is reacted with the ω-hydroxy oxime represented by the formula (2) in the presence of an organotin compound to obtain the compound represented by the formula (3). Formula (6), characterized in that the N-cyclic acetal-substituted nitrone represented is reacted with an olefin represented by the formula (4), and then the obtained compound represented by the formula (5) is hydrolyzed. The present invention provides a method for producing an N-unsubstituted isoxazolidine represented by:

【００１０】[0010]

【発明の実施の形態】本発明において原料として用いら
れるアルデヒド類を示す式（１）中、Ｒ1 で示される置
換基を有していてもよい芳香族基としては、フェニル、
ナフタレン、芳香族複素環などの基にアルキル基、アル
コキシ基、ニトロ基、ハロゲン原子等が置換した基が挙
げられる。一方、置換基を有していてもよい脂肪族基と
しては、アルコキシ基、ニトロ基、芳香族基などが置換
したアルキレン基が挙げられる。BEST MODE FOR CARRYING OUT THE INVENTION In the formula (1) showing an aldehyde used as a raw material in the present invention, an aromatic group which may have a substituent represented by R 1 is phenyl,
Examples thereof include groups in which an alkyl group, an alkoxy group, a nitro group, a halogen atom or the like is substituted on a group such as naphthalene or an aromatic heterocycle. On the other hand, examples of the aliphatic group which may have a substituent include an alkylene group substituted with an alkoxy group, a nitro group or an aromatic group.

【００１１】また、もう一方の原料であるω−ヒドロキ
シオキシムを示す式（２）中、Ｒ2で示される置換基を
有していてもよい直鎖又は分岐鎖のアルキレン基として
は、炭素数２〜６の置換基を有していてもよいアルキレ
ン基が挙げられるが、炭素数３〜５の置換基を有してい
てもよいアルキレン基がより好ましい。ここで、アルキ
レン基上の置換基としては、糖類から誘導された光学活
性酸素官能基であってもよい。Further, in the formula (2) showing ω-hydroxyoxime as the other raw material, the linear or branched alkylene group which may have a substituent represented by R 2 has a carbon number. Examples of the alkylene group which may have a substituent of 2 to 6 include alkylene groups which may have a substituent of 3 to 5 carbon atoms. Here, the substituent on the alkylene group may be an optically active oxygen functional group derived from a saccharide.

【００１２】オレフィン類を示す式（４）中、Ｒ3、
Ｒ4、Ｒ5 及びＲ6 で示される有機基としては、置換基
を有していてもよい脂肪族基、置換基を有していてもよ
い芳香族基、置換基を有していてもよいカルボン酸エス
テル残基等が挙げられるが、さらにはこれらの基が互い
に結合して芳香族基や複素環を形成していてもよい。In the formula (4) showing olefins, R 3 ,
Examples of the organic group represented by R 4 , R 5 and R 6 include an aliphatic group which may have a substituent, an aromatic group which may have a substituent and a substituent which may have a substituent. Examples of the preferred carboxylic acid ester residue include these groups, and these groups may be bonded to each other to form an aromatic group or a heterocycle.

【００１３】アルデヒド類（１）とω−ヒドロキシオキ
シム（２）との縮合反応に触媒として用いられる有機ス
ズ化合物としては、酸化ジブチルスズ、酸化ジオクチル
スズ等の酸化ジアルキルスズ；ジブチルスズジアセテー
ト等のジアルキルスズジカルボン酸エステル等が挙げら
れる。Organotin compounds used as catalysts in the condensation reaction of aldehydes (1) with ω-hydroxyoxime (2) include dialkyltin oxides such as dibutyltin oxide and dioctyltin oxide; dialkyltins such as dibutyltin diacetate. Examples thereof include dicarboxylic acid esters.

【００１４】アルデヒド類（１）とω−ヒドロキシオキ
シム（２）との反応は、前記有機スズ化合物を微量、好
ましくは原料に対し１〜５モル％の存在下、トルエン、
ベンゼン等の不活性溶媒中、数時間（触媒量により３〜
６時間）加熱還流するのが好ましい。なお、原料化合物
の使用モル比は、特に制限されないが１：１が好まし
い。The reaction between the aldehydes (1) and the ω-hydroxy oxime (2) is carried out in the presence of a small amount of the above organic tin compound, preferably 1 to 5 mol% based on the raw material, toluene,
In an inert solvent such as benzene for several hours (depending on the amount of catalyst, 3 to
It is preferable to heat and reflux for 6 hours. The molar ratio of the raw material compound used is not particularly limited, but is preferably 1: 1.

【００１５】得られたＮ−環状アセタール置換ニトロン
（３）とオレフィン類（４）との反応は、通常の縮合環
化条件、例えばベンゼン、トルエン等の不溶性溶媒中で
加熱還流することにより行われる。反応は数時間で充分
である。The reaction of the obtained N-cyclic acetal-substituted nitrone (3) with the olefins (4) is carried out by heating under reflux in an ordinary condensation cyclization condition, for example, an insoluble solvent such as benzene or toluene. . A few hours is sufficient for the reaction.

【００１６】上記反応により得られるＮ−置換オキソゾ
リジン類（５）の加水分解は、酸性条件下に行うのが好
ましい。用いる酸としては塩酸、硝酸、硫酸等の鉱酸が
好ましい。Hydrolysis of the N-substituted oxozolidines (5) obtained by the above reaction is preferably carried out under acidic conditions. The acid used is preferably a mineral acid such as hydrochloric acid, nitric acid or sulfuric acid.

【００１７】反応後の酸性水溶液から、目的物を抽出す
るには、中性不純物を抽出除去後、水層をアルカリ性に
すればよい。また、さらに目的物を精製するには、再結
晶、カラムクロマトグラフィー等を利用すればよい。To extract the desired product from the acidic aqueous solution after the reaction, the neutral layer is extracted and removed, and then the aqueous layer is made alkaline. Further, to further purify the desired product, recrystallization, column chromatography or the like may be used.

【００１８】[0018]

【実施例】次に実施例を挙げて本発明を詳細に説明する
が、本発明はこれら実施例に限定されるものではない。EXAMPLES The present invention will now be described in detail with reference to examples, but the present invention is not limited to these examples.

【００１９】実施例１ （１）ベンズアルデヒド（１０．６ｇ，０．１mol ）、
５−ヒドロキシペンタナールオキシム（１１．７ｇ，
０．１mol ）と酸化ジブチルスズ（０．５ｇ，２mol
％）のベンゼン溶液（１００ml）を５時間加熱還流し
た。溶媒を留去した後、残渣を酢酸エチル−ヘキサンか
ら再結晶しベンズアルデヒド−Ｎ−テトラヒドロピラニ
ルニトロン１７．６ｇ（８７％）を得た。Example 1 (1) Benzaldehyde (10.6 g, 0.1 mol),
5-hydroxypentanal oxime (11.7 g,
0.1 mol) and dibutyltin oxide (0.5 g, 2 mol)
%) In benzene (100 ml) was heated to reflux for 5 hours. After the solvent was distilled off, the residue was recrystallized from ethyl acetate-hexane to obtain benzaldehyde-N-tetrahydropyranyl nitrone (17.6 g, 87%).

【００２０】融点 76〜78℃1 H-NMR；8.30(m,2H), 7.79(s,1H), 7.42(m,3H), 4.88
(m,1H), 4.20(m,1H),3.68(m,1H), 2.46(m,1H), 1.98(m,
1H), 1.66(m,4H).13 C-NMR；130.6, 130.3, 130.2, 129.0, 128.3, 95.8,
67.8, 30.5, 24.9,21.7.Melting point 76-78 ° C. 1 H-NMR; 8.30 (m, 2H), 7.79 (s, 1H), 7.42 (m, 3H), 4.88
(m, 1H), 4.20 (m, 1H), 3.68 (m, 1H), 2.46 (m, 1H), 1.98 (m,
1H), 1.66 (m, 4H). 13 C-NMR; 130.6, 130.3, 130.2, 129.0, 128.3, 95.8,
67.8, 30.5, 24.9, 21.7.

【００２１】（２）ベンズアルデヒド−Ｎ−テトラヒド
ロピラニルニトロン（２０５mg，１．０mmol）と、アク
リル酸メチル（０．１８ml，２．０mmol）のトルエン溶
液（５ml）を６時間加熱還流した。溶媒を留去後メタノ
ール（５ml）、７０％過塩素酸水溶液（０．１ml）を加
え６０℃で１時間反応した。飽和炭酸水素ナトリウム水
溶液にあけ、エーテルで抽出し、結晶化することによ
り、１８５mg（８９％）の３−フェニルイソオキサゾリ
ジン−５−カルボン酸メチルを得た。(2) A toluene solution (5 ml) of benzaldehyde-N-tetrahydropyranyl nitrone (205 mg, 1.0 mmol) and methyl acrylate (0.18 ml, 2.0 mmol) was heated under reflux for 6 hours. After distilling off the solvent, methanol (5 ml) and 70% aqueous perchloric acid solution (0.1 ml) were added and the reaction was carried out at 60 ° C. for 1 hour. It was poured into a saturated aqueous solution of sodium hydrogen carbonate, extracted with ether, and crystallized to obtain 185 mg (89%) of methyl 3-phenylisoxazolidine-5-carboxylate.

【００２２】1H-NMR；7.2〜7.4(m,2H), 6.9〜7.2(m,3
H), 6.0(br,1H),4.33(dd,J=4.5,8.6Hz,1H), 4.07(m,1
H), 3.25(m,3H), 2.23(m,1H),2.08(m,1H). 1 H-NMR; 7.2 to 7.4 (m, 2H), 6.9 to 7.2 (m, 3
H), 6.0 (br, 1H), 4.33 (dd, J = 4.5,8.6Hz, 1H), 4.07 (m, 1
H), 3.25 (m, 3H), 2.23 (m, 1H), 2.08 (m, 1H).

【００２３】実施例２〜６ オレフィン類として、表１記載の化合物を用いる以外は
実施例１と同様にして表１のＮ−無置換イソオキサゾリ
ジンを得た。Examples 2 to 6 N-unsubstituted isoxazolidines in Table 1 were obtained in the same manner as in Example 1 except that the compounds shown in Table 1 were used as the olefins.

【００２４】[0024]

【表１】 [Table 1]

【００２５】実施例７ 実施例１（１）と同様にして得られたベンズアルデヒド
−Ｎ−テトラヒドロピラニルニトロン（１．５０ｇ，
７．３１mmol）と１−アミノベンゾトリアゾール（１．
００ｇ，７．４５mmol）の塩化メチレン溶液（３０ml）
に４酢酸鉛（３．５０ｇ，７．８９mmol）を加え、０℃
で１時間攪拌した。反応混合物を濃縮後、クロマトグラ
フィーにより付加物（１．４０ｇ，６８％）を得た。こ
れをメタノール（５０ml）中、７０％過塩素酸（０．５
ml）と６０℃、３０分反応させた。放冷後メタノールを
留去し、１Ｎ水酸化ナトリウムを加え、塩化メチレンで
抽出し、クロマトグラフィーにより下記化合物を０．８
５ｇ（６８％）得た。Example 7 Benzaldehyde-N-tetrahydropyranyl nitrone (1.50 g, obtained in the same manner as in Example 1 (1))
7.31 mmol) and 1-aminobenzotriazole (1.
A solution of 00g, 7.45mmol) in methylene chloride (30ml)
Add lead tetraacetate (3.50g, 7.89mmol) to
For 1 hour. After the reaction mixture was concentrated, the adduct (1.40 g, 68%) was obtained by chromatography. 70% perchloric acid (0.5%) in methanol (50 ml)
ml) and reacted at 60 ° C. for 30 minutes. After cooling, methanol was distilled off, 1N sodium hydroxide was added, the mixture was extracted with methylene chloride, and the following compound was extracted by chromatography to 0.8%.
5 g (68%) was obtained.

【００２６】[0026]

【化８】 Embedded image

【００２７】融点 49〜51℃（エーテル−ヘキサン）1 H-NMR(CDCl3)；7.36(m,5H), 7.22(t,J=7.6Hz,1H), 7.0
7(d,J=7.3Hz,1H),6.94(t,J=7.0Hz,1H), 6.93(d,J=7.3H
z,1H), 6.70(br,1H),5.69(d,J=10.2Hz,1H).Melting point 49-51 ° C. (ether-hexane) 1 H-NMR (CDCl 3 ); 7.36 (m, 5H), 7.22 (t, J = 7.6Hz, 1H), 7.0
7 (d, J = 7.3Hz, 1H), 6.94 (t, J = 7.0Hz, 1H), 6.93 (d, J = 7.3H
z, 1H), 6.70 (br, 1H), 5.69 (d, J = 10.2Hz, 1H).

【００２８】[0028]

【発明の効果】本発明によればアルデヒドとω−ヒドロ
キシオキシムとの反応が低温かつ短時間で終了するの
で、副反応が少なく、高収率で、かつ広範囲のＮ−無置
換イソオキサゾリジン類が得られる。EFFECTS OF THE INVENTION According to the present invention, the reaction between the aldehyde and the ω-hydroxyoxime is completed at low temperature and in a short time, so that there are few side reactions, a high yield and a wide range of N-unsubstituted isoxazolidines are obtained. can get.

Claims (1)

【特許請求の範囲】[Claims] 【請求項１】 次式（１） 【化１】 （式中、Ｒ1 は置換基を有していてもよい芳香族基又は
置換基を有していてもよい脂肪族基を示す）で表される
アルデヒド類に式（２） 【化２】 （式中、Ｒ2 は置換基を有していてもよい直鎖又は分岐
鎖のアルキレン基を示す）で表されるω−ヒドロキシオ
キシムを有機スズ化合物の存在下に反応させ、得られる
式（３） 【化３】 （式中、Ｒ1 及びＲ2 は前記と同じ）で表されるＮ−環
状アセタール置換ニトロンに次式（４） 【化４】 （式中、Ｒ3、Ｒ4、Ｒ5 及びＲ6 はそれぞれ水素原子又
は有機基を示す）で表されるオレフィン類を反応させ、
次いで得られた式（５） 【化５】 （式中、Ｒ1、Ｒ2、Ｒ3、Ｒ4、Ｒ5 及びＲ6 は前記と同
じ）で表される化合物を加水分解することを特徴とする
式（６） 【化６】 （式中、Ｒ1a、Ｒ3a、Ｒ4a、Ｒ5a及びＲ6aはそれぞれＲ
1、Ｒ3、Ｒ4、Ｒ5 及びＲ6 を示すか又はこれらの基が
加水分解を受けて生じる基もしくは水素原子を示す）で
表されるＮ−無置換イソオキサゾリジンの製造法。1. The following formula (1) (Wherein R 1 represents an aromatic group which may have a substituent or an aliphatic group which may have a substituent), and the aldehyde represented by the formula (2) (In the formula, R 2 represents a linear or branched alkylene group which may have a substituent), and ω-hydroxyoxime is reacted in the presence of an organotin compound to obtain a formula ( 3) [Chemical 3] (Wherein R 1 and R 2 are the same as above) and the N-cyclic acetal-substituted nitrone is represented by the following formula (4): (Wherein R 3 , R 4 , R 5 and R 6 each represent a hydrogen atom or an organic group),
The resulting formula (5) (Wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are the same as above), the compound represented by the formula (6) is hydrolyzed. (In the formula, R 1a , R 3a , R 4a , R 5a and R 6a are each R
1 , R 3 , R 4 , R 5 and R 6 or a group or hydrogen atom formed by hydrolysis of these groups).
JP7234126A 1995-09-12 1995-09-12 Process for producing N-unsubstituted isoxazolidine Pending JPH0977751A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP7234126A JPH0977751A (en) 1995-09-12 1995-09-12 Process for producing N-unsubstituted isoxazolidine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP7234126A JPH0977751A (en) 1995-09-12 1995-09-12 Process for producing N-unsubstituted isoxazolidine

Publications (1)

Publication Number Publication Date
JPH0977751A true JPH0977751A (en) 1997-03-25

Family

ID=16966050

Family Applications (1)

Application Number Title Priority Date Filing Date
JP7234126A Pending JPH0977751A (en) 1995-09-12 1995-09-12 Process for producing N-unsubstituted isoxazolidine

Country Status (1)

Country Link
JP (1) JPH0977751A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9822135B2 (en) 2012-10-30 2017-11-21 H. Lee Moffitt Cancer Center And Research Institute, Inc. STAT3 dimerization inhibitors

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9822135B2 (en) 2012-10-30 2017-11-21 H. Lee Moffitt Cancer Center And Research Institute, Inc. STAT3 dimerization inhibitors
US10494389B2 (en) 2012-10-30 2019-12-03 H. Lee Moffitt Cancer Center And Research Institute, Inc. STAT3 dimerization inhibitors
US10954258B2 (en) 2012-10-30 2021-03-23 H. Lee Moffitt Cancer Center And Research Institute, Inc. STAT3 dimerization inhibitors

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