JPS5835994B2 - Quinolinone imine derivative and method for producing the same - Google Patents
Quinolinone imine derivative and method for producing the sameInfo
- Publication number
- JPS5835994B2 JPS5835994B2 JP16212678A JP16212678A JPS5835994B2 JP S5835994 B2 JPS5835994 B2 JP S5835994B2 JP 16212678 A JP16212678 A JP 16212678A JP 16212678 A JP16212678 A JP 16212678A JP S5835994 B2 JPS5835994 B2 JP S5835994B2
- Authority
- JP
- Japan
- Prior art keywords
- quinolinone
- producing
- dichlorophenyl
- formula
- 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.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- -1 Quinolinone imine Chemical class 0.000 title description 9
- 229930185107 quinolinone Natural products 0.000 title description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 235000011054 acetic acid Nutrition 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229960003424 phenylacetic acid Drugs 0.000 description 6
- 239000003279 phenylacetic acid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
- 239000005695 Ammonium acetate Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000019257 ammonium acetate Nutrition 0.000 description 3
- 229940043376 ammonium acetate Drugs 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 125000005427 anthranyl group Chemical group 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 238000005659 Kindler reaction Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical class OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- SQEOYWVUJIPLKN-UHFFFAOYSA-N ethyl 1-(2,6-dichlorophenyl)-2-iminoquinoline-3-carboxylate Chemical compound N=C1C(C(=O)OCC)=CC2=CC=CC=C2N1C1=C(Cl)C=CC=C1Cl SQEOYWVUJIPLKN-UHFFFAOYSA-N 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- ZWJINEZUASEZBH-UHFFFAOYSA-N fenamic acid Chemical class OC(=O)C1=CC=CC=C1NC1=CC=CC=C1 ZWJINEZUASEZBH-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 1
- QJIJQNUQORKBKY-UHFFFAOYSA-N piperidin-1-ium;benzoate Chemical compound C1CCNCC1.OC(=O)C1=CC=CC=C1 QJIJQNUQORKBKY-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Quinoline Compounds (AREA)
Description
【発明の詳細な説明】
本発明は、キノリノンイミン誘導体およびその製造方法
に関し、さらに詳しくは、医薬品として有用な式（ＩＶ
）
で表わされる０−（２・６−ジクロロアニリノ）フェニ
ル酢酸を製造するための中間原料となるキノリノンイミ
ン誘導体およびその製造方法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a quinolinone imine derivative and a method for producing the same, and more particularly, the present invention relates to a quinolinone imine derivative and a method for producing the same.
The present invention relates to a quinolinone imine derivative that is an intermediate raw material for producing 0-(2,6-dichloroanilino)phenylacetic acid represented by the following formula, and a method for producing the same.
０−（２・６−ジクロロアニリノ）フェニル酢酸は、抗
炎症作用、鎮痛作用および解熱作用等を有することが知
られ、その製造方法としては、例えば
（１）ジフェニルアミン誘導体をクロロアセチルハライ
ドと反応せしめ、次いでこれよりインドリノン誘導体を
合成し、これを加水分解する方法（特公昭４２−２３４
１８号明細書）、
（２）Ｎ−フェニルアントラニル酸誘導体を還元して得
られる０−アニリノベンジル誘導体から誘導する方法（
特公昭４４−２７３７４号および特公昭４５−１１２９
５号明細書）、
（３）０−アニリノアセトフェノン誘導体よりウイルゲ
ロットーキンドラー反応を経て得られるモルホライド誘
導体から誘導する方法（特公昭４４−２７５７３号明細
書）などが提案されている。0-(2,6-dichloroanilino)phenylacetic acid is known to have anti-inflammatory, analgesic, and antipyretic effects, and methods for producing it include, for example, (1) reacting a diphenylamine derivative with chloroacetyl halide. A method of synthesizing an indolinone derivative from this and hydrolyzing it (Japanese Patent Publication No. 42-234
18), (2) A method of deriving from an 0-anilinobenzyl derivative obtained by reducing an N-phenylanthranilic acid derivative (
Special Publication No. 44-27374 and Special Publication No. 1129 of 1977
(3) A method of deriving from a morpholide derivative obtained from an 0-anilinoacetophenone derivative through the Wilgerott-Kindler reaction (Japanese Patent Publication No. 27573/1983) has been proposed.
しかしながら、これらの方法は、いずれも反応工程が複
雑で、収率も充分満足のいくものではない。However, all of these methods involve complicated reaction steps and yields that are not fully satisfactory.
本発明の目的は、上記従来技術に鑑み、工程が比較的簡
単で、かつ高い収率で０−（２・６−ジクロロアニリノ
）フェニル酢酸を得るための中間原料およびその製造方
法を提供することにある。In view of the above prior art, an object of the present invention is to provide an intermediate raw material for obtaining 0-(2,6-dichloroanilino)phenylacetic acid with a relatively simple process and a high yield, and a method for producing the same. There is a particular thing.
本発明者らの研究によれば、式（１）
で表わされるＮ−（２・６−ジクロロフェニル）アント
ラニルアルテヒドと、式（ＩＩＩ）（但し、式中Ｒは低
級アルキル基を示す）で表わされるジアゾ酢酸エステル
類とを縮合させると高収率で前記式（■）
で表わされる１−（２・６−ジクロロフェニル）３−ア
ルコキシカルボニル−２−キノリノンイミン誘導体（但
し、式中Ｒは低級アルキル基を示す）が得られることが
わかった。According to the research of the present inventors, N-(2,6-dichlorophenyl)anthranyl altehyde represented by formula (1) and N-(2,6-dichlorophenyl)anthranyl altehyde represented by formula (III) (wherein R represents a lower alkyl group) 1-(2,6-dichlorophenyl)3-alkoxycarbonyl-2-quinolinone imine derivative represented by the above formula (■) (wherein R is a lower alkyl group) ) was found to be obtained.
次いでこの化合物を特定条件下に酸化すると、選択的に
３・４一位がエポキシ化され、式（Ｖ）
（但し、式中Ｒは低級アルキル基を示す）で表わサレル
１−（２・６−ジクロロフェニル）−３アルコキシカル
ボニル−３・４−エポキシ−２−キノリノンイミン誘導
体が得られ、さらに研究を進めた結果、驚くべきことに
、この化合物に単に塩基を作用させるのみで、高純度、
かつ高収率で前記式（ＩＶ）で表わされる０−（２・６
−ジクロロアニリノ）フェニル酢酸が得られることを見
出した。Next, when this compound is oxidized under specific conditions, the 3 and 4-1 positions are selectively epoxidized, resulting in salel 1-(2, 6-dichlorophenyl)-3alkoxycarbonyl-3,4-epoxy-2-quinolinone imine derivative was obtained, and as a result of further research, surprisingly, simply by reacting this compound with a base, high purity,
and 0-(2.6 represented by the formula (IV)) in high yield.
-dichloroanilino)phenylacetic acid was found to be obtained.
本発明によれば、医薬品として有用な０−（２・６−ジ
クロロアニリノ）フェニル酢酸の中間原料として、式（
Ｉ）で表わされる１−（２・６−ジクロロフェニル）
−３−フルコキシカルボニルー２−キノリノンイミン誘
導体が提供される。According to the present invention, the formula (
1-(2,6-dichlorophenyl) represented by I)
-3-Flucoxycarbonyl-2-quinolinoneimine derivatives are provided.
この化合物は文献未載の新規化合物である。This compound is a new compound that has not been described in any literature.
前記式（Ｉ）および（ＩＩＩ）で表わされる化合物のＲ
は、メチル基、エチル基、プロピル基、ブチル基等の低
級アルキル基を示すが、これらの内、エチル基、メチル
基を有するものが特に好ましい。R of the compounds represented by formulas (I) and (III) above
represents a lower alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, and among these, those having an ethyl group or a methyl group are particularly preferred.
本発明において、前記式（１）で表わされる目的化合物
は、前記式（川）で表わされるＮ−（２・６−ジクロロ
フェニル）アントラニルアルデヒドと、前記式（ＩＩＩ
）で表わされるシアノ酢酸エステル類を触媒共存下で縮
合することにより製造される。In the present invention, the target compound represented by the above formula (1) is N-(2,6-dichlorophenyl)anthranylaldehyde represented by the above formula (Kawa) and the above formula (III).
) is produced by condensing cyanoacetic esters represented by () in the presence of a catalyst.
この縮合反応に使用されるシアノ酢酸エステル類は、Ｎ
−（２・６−ジクロロフェニル）アントラニルアルデヒ
ド１モルに対して１．０モルから３．０モル、好ましく
は１．１モルから１．５モルである。The cyanoacetates used in this condensation reaction are N
The amount is from 1.0 mol to 3.0 mol, preferably from 1.1 mol to 1.5 mol, per mol of -(2,6-dichlorophenyl)anthranyl aldehyde.
触媒としては、例えば酢酸アンモニウムと酢酸の混合物
、酢酸ピペリジニウムと酢酸の混合物、および安息香酸
ピペリジニウムと酢酸等のようなアミンの有機酸塩と酢
酸の混合物が挙げられるが、これらの内、酢酸アンモニ
ウムと酢酸の混合物が特に好ましく用いられる。Examples of the catalyst include a mixture of ammonium acetate and acetic acid, a mixture of piperidinium acetate and acetic acid, and a mixture of acetic acid and an organic acid salt of an amine such as piperidinium benzoate and acetic acid. Particular preference is given to using mixtures of acetic acids.
この場合の触媒の量は、酢酸アンモニウムについては０
．５モルから５モル、好ましくは１．０モルから２モル
であり、酢酸については０．５モルから１０モル、好ま
しくは１．０モルから４モルである。The amount of catalyst in this case is 0 for ammonium acetate.
．． The amount is from 5 mol to 5 mol, preferably from 1.0 mol to 2 mol, and for acetic acid from 0.5 mol to 10 mol, preferably from 1.0 mol to 4 mol.
溶媒としては、ベンゼン、トルエン、キシレン等、反応
に関与しないものであれば何れも使用することができる
が、反応中に生成する水を溶媒との共沸混合物として除
去しながら反応を行なうことができるものが好ましい。Any solvent that does not participate in the reaction, such as benzene, toluene, and xylene, can be used as the solvent, but it is possible to carry out the reaction while removing water produced during the reaction as an azeotrope with the solvent. Preferably something that can be done.
反応時間は１時間から１２２時間程、好ましくは２時間
から５時間程度である。The reaction time is about 1 hour to 122 hours, preferably about 2 hours to 5 hours.
反応温度は、使用した溶媒の沸点付近が好ましい。The reaction temperature is preferably around the boiling point of the solvent used.
以上のようにして得られた式（Ｉ）の化合物は、後の参
考例に示すように、酸化後、塩基を作用させることによ
り、〇−（２・６−ジクロロアニリノ）フェニル酢酸に
容易に転化される。The compound of formula (I) obtained as described above can be easily converted to 〇-(2,6-dichloroanilino)phenylacetic acid by reacting with a base after oxidation, as shown in the reference examples below. converted into.
以下、本発明を実施例によりさらに詳しく説明する。Hereinafter, the present invention will be explained in more detail with reference to Examples.
実施例
１−（２・６ジクロロフエニル） −３−エトキシカル
ボニル−２−キノリノンイミンの製造Ｎ−（２・６ジク
ロロフエニル）アントラニルアルデヒド１５０ｆ、シア
ノ酢酸エチル９８１、酢酸１２８Ｐ、酢酸アンモニウム
７８１およびベンゼン７５０ｒｒＬｌの混合物を、水分
除去装置を備えた反応容器内で、水を除去しながら３時
間還流させた。Example 1 - Preparation of (2,6 dichlorophenyl)-3-ethoxycarbonyl-2-quinolinone imine N-(2,6 dichlorophenyl) anthranyl aldehyde 150f, ethyl cyanoacetate 981, acetic acid 128P, ammonium acetate 781 and benzene The 750 rrLl mixture was refluxed for 3 hours while removing water in a reaction vessel equipped with a water removal device.
放冷後、反応液を水洗し、水洗層を分取した。After cooling, the reaction solution was washed with water, and the washed layer was separated.
この水洗層を水酸化ナトリウムにてアルカリ性にするこ
とに析出した黄色結晶をＰ取した。The washed layer was made alkaline with sodium hydroxide, and the precipitated yellow crystals were collected.
一方、ベンゼン層は、硫酸マグネシウムで乾燥した後、
ベンゼンを留去し、得られた残渣をインプロパツールに
て結晶化し、析出した黄色結晶を１取した。On the other hand, the benzene layer was dried with magnesium sulfate, then
Benzene was distilled off, and the resulting residue was crystallized using an inproper tool, and one precipitated yellow crystal was collected.
この黄色結晶と先にＰ取した黄色結晶を合わせてエタノ
ールで再結晶し、１−（２・６ジクロロフエニル）−３
−エトキシカルボニル−２−キノリノンイミンの黄色結
晶１８３．３ｆを得た。This yellow crystal and the yellow crystal from which P was removed earlier were combined and recrystallized with ethanol, and 1-(2.6 dichlorophenyl)-3
-Ethoxycarbonyl-2-quinolinoneimine yellow crystals 183.3f were obtained.
融点１６９〜１７０℃。Melting point: 169-170°C.
収率は、理論量の９０％であった。The yield was 90% of theory.
分析値を以下に示す。元素分析値（％）
ジカルボニル−２−キノリノンイミン１１８グをエタノ
ール１．２１に熱時溶解した後、室温に冷却し、タング
ステン酸ナトリウム５３グを添加した。The analytical values are shown below. Elemental analysis value (%) After hot dissolving 118 g of dicarbonyl-2-quinolinone imine in 1.21 g of ethanol, it was cooled to room temperature, and 53 g of sodium tungstate was added.
次に、３０％過酸化水素水９６ｒＩｌｌを滴下し、さら
に室温で２時間攪拌した。Next, 96 ml of 30% hydrogen peroxide solution was added dropwise, and the mixture was further stirred at room temperature for 2 hours.
反応後、反応液を水で希釈し、斤出した結晶を１取した
。After the reaction, the reaction solution was diluted with water, and one loaf of crystals was collected.
得られた結晶をイン％−／しで再結晶し、１−（２・６
ジクロロフェニル）−３−エトキシカルボニル−３・４
−エポキシ−２−キノリノンイミンの白色結晶１１０グ
を得た。The obtained crystals were recrystallized with in%-/2 to give 1-(2.6
dichlorophenyl)-3-ethoxycarbonyl-3,4
-110 g of white crystals of epoxy-2-quinolinone imine were obtained.
融点１３０〜１３１℃。収率は理論量の８９．３％であ
った。Melting point: 130-131°C. The yield was 89.3% of theory.
分析値を以下に示す。元素分析値（％）
質量分析（ｍ／ｌ） ： ３７６ （Ｍ＋）、３７８
（Ｍ”十、 ）
参考例 ２
ｏ−（２・６−ジクロロアニリノフェニル酢酸の製造
１−（２・６−ジクロロフェニル）−３−エトキシカポ
ニル−３・４−エポキシ−２−キノリノンイミン１１０
ｔをエタノール１，２１に熱時溶解した後、水浴で２０
℃まで冷却し、この冷却後の液に塩基として水酸化カリ
ウム２２０ｔを加えた。The analytical values are shown below. Elemental analysis value (%) Mass spectrometry (m/l): 376 (M+), 378
(M”10, ) Reference Example 2 Production of o-(2,6-dichloroanilinophenyl acetic acid 1-(2,6-dichlorophenyl)-3-ethoxycaponyl-3,4-epoxy-2-quinolinoneimine 110
After hot dissolving t in ethanol 1,21, it was dissolved in a water bath for 20
The solution was cooled to .degree. C., and 220 t of potassium hydroxide was added as a base to the cooled solution.
溶液が白濁したのち、さらに３０分間攪拌し、その後５
時間還流した。After the solution became cloudy, it was stirred for another 30 minutes, and then stirred for 5 minutes.
Refluxed for an hour.
その後、溶媒を留去し、残渣を水に溶解した。Thereafter, the solvent was distilled off, and the residue was dissolved in water.
さらに濃塩酸でｐＨ２〜３にした後、そのまま１時間攪
拌した。After adjusting the pH to 2 to 3 with concentrated hydrochloric acid, the mixture was stirred for 1 hour.
析出物をＰ取乾燥したのち、ベンゼンより再結晶して０
−（２・６−ジクロロアニリノ）−フェニル酢酸６ｏ、
４ｙを得た。After removing the precipitate and drying it, it was recrystallized from benzene to give 0
-(2,6-dichloroanilino)-phenylacetic acid 6o,
Got 4y.
融点１５６〜１５８℃。収率は理論量の７０％であった
。Melting point 156-158°C. The yield was 70% of theory.
この物を、別途合成した０−（２・６−ジクロロアニリ
ノ）−フェニル酢酸と混融したところ、何ら融点降下を
示さなかった。When this product was mixed with separately synthesized 0-(2,6-dichloroanilino)-phenylacetic acid, no decrease in melting point was observed.
Claims (1)
１−（２・６−ジクロロフェニル）−３アルコキシカル
ボニル−２−キノリノンイミン誘導体。 ２ 式（１） で表わされるＮ−（２・６−ジクロロフェニル）アンド
ラニルアルテヒドと、式（ＩＩＩ）（但し、式中Ｒは低
級アルキル基を示す）で表わされるシアノ酢酸エステル
類を縮合することを特徴とする式（ｉ） （但し、式中Ｒは低級アルキル基を示す）で表わされる
１−（２・６−シクロロフエニ／１／）−３−アルコキ
シカルボニル−２−キノリノンイミン誘導体の製造方法
。[Scope of Claims] 1. A 1-(2,6-dichlorophenyl)-3alkoxycarbonyl-2-quinolinone imine derivative represented by formula (I) (wherein R represents a lower alkyl group). 2 N-(2,6-dichlorophenyl)andranylaltehyde represented by formula (1) and cyanoacetic esters represented by formula (III) (wherein R represents a lower alkyl group) are condensed. A method for producing a 1-(2,6-cyclophenylene/1/)-3-alkoxycarbonyl-2-quinolinone imine derivative represented by formula (i) (wherein R represents a lower alkyl group), characterized by .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16212678A JPS5835994B2 (en) | 1978-12-25 | 1978-12-25 | Quinolinone imine derivative and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16212678A JPS5835994B2 (en) | 1978-12-25 | 1978-12-25 | Quinolinone imine derivative and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5585568A JPS5585568A (en) | 1980-06-27 |
| JPS5835994B2 true JPS5835994B2 (en) | 1983-08-05 |
Family
ID=15748528
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16212678A Expired JPS5835994B2 (en) | 1978-12-25 | 1978-12-25 | Quinolinone imine derivative and method for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5835994B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20210098243A (en) * | 2020-01-31 | 2021-08-10 | 삼성메디슨 주식회사 | Ultrasound imaging apparatus, method for controlling the same, and computer program |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5721371A (en) * | 1980-07-11 | 1982-02-04 | Daito Koeki Kk | Quinolinoneiminecarboxylic ester derivative, its preparation and anti-inflammatory and analgesic agent composition containing the same |
-
1978
- 1978-12-25 JP JP16212678A patent/JPS5835994B2/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20210098243A (en) * | 2020-01-31 | 2021-08-10 | 삼성메디슨 주식회사 | Ultrasound imaging apparatus, method for controlling the same, and computer program |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5585568A (en) | 1980-06-27 |
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