JPS6034555B2 - Method for producing 1-azaxanthone derivative - Google Patents
Method for producing 1-azaxanthone derivativeInfo
- Publication number
- JPS6034555B2 JPS6034555B2 JP15389877A JP15389877A JPS6034555B2 JP S6034555 B2 JPS6034555 B2 JP S6034555B2 JP 15389877 A JP15389877 A JP 15389877A JP 15389877 A JP15389877 A JP 15389877A JP S6034555 B2 JPS6034555 B2 JP S6034555B2
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- Japan
- Prior art keywords
- formula
- general formula
- azaxanthone
- ring
- compound
- Prior art date
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Description
【発明の詳細な説明】 本発明は１−アザキサントン誘導体の製造法に関する。[Detailed description of the invention] The present invention relates to a method for producing 1-azaxanthone derivatives.
さらに詳しくは、本発明は一般式（ｍ）〔式中、Ａ環は
ハロゲン原子またはアルキル基で置換されていてもよい
〕で示される化合物に置換ホルムァミドの存在下にシア
ン酢酸ハロゲニドを反応させることからなる一般式（ロ
）〔式中、Ａ環は前記と同意義を表わす〕で示される１
ーアザキサントン誘導体の製造法ならびにこのようにし
て得た一般式（０）で示される化合物を加水分解するこ
とにより一般式（１）〔式中、Ａ環は前記と同意菱を表
わす〕で示される１−アザキサン−３−カルボン酸誘導
体またはその他の製造法に関する。More specifically, the present invention involves reacting a compound represented by general formula (m) (in which ring A may be substituted with a halogen atom or an alkyl group) with cyanacetic acid halide in the presence of a substituted formamide. 1 represented by the general formula (b) [in the formula, ring A represents the same meaning as above]
-A method for producing an azaxanthone derivative, and by hydrolyzing the compound represented by the general formula (0) thus obtained, a compound represented by the general formula (1) [wherein A ring represents the same rhombus as above] is produced. -Relating to azaxane-3-carboxylic acid derivatives or other manufacturing methods.
本発明の方法によって得られる一般式（１）の化合物ま
たはその塩は抗アレルギー作用を有し、抗アレルギー剤
などの医薬として有用である。The compound of general formula (1) or a salt thereof obtained by the method of the present invention has an antiallergic effect and is useful as a medicine such as an antiallergic agent.
前記各式中、Ａ環で示されるベンゼン環の置換基である
アルキル基としては、たとえばメチル、エチル、プロピ
ル、イソプロピル、ブチル、イソプチル、ｔ−プチル、
ベンチル、ヘキシル基などの炭素数１〜６の直鎖、分枝
アルキル基があげられ、なかでも炭素数１〜４の低級ア
ルキル基が実用上好ましい。また、ハロゲン原子として
は、塩素、臭素、ヨウ素、フッ素があげられる。これら
のＡ環で示されるベンゼン環の置換数は１または２以上
、同一または異つてＡ環の任意の位置に置換していてよ
い。In each of the above formulas, examples of the alkyl group as a substituent on the benzene ring represented by ring A include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl,
Examples include straight chain and branched alkyl groups having 1 to 6 carbon atoms such as bentyl and hexyl groups, and among them, lower alkyl groups having 1 to 4 carbon atoms are practically preferred. Furthermore, examples of the halogen atom include chlorine, bromine, iodine, and fluorine. The number of substitutions on the benzene ring represented by these A rings is 1 or 2 or more, and the substitutions may be the same or different and may be substituted at any position of the A ring.
本発明の一般式（Ｄ）の化合物は次の方法により製造す
ることができる。The compound of general formula (D) of the present invention can be produced by the following method.
即ち、一般式（ｍ）の化合物に置換ホルムァミドの存在
下に、シアン酢酸ハロゲニドを反応させることによって
製造される。反応に用いられるシアン酢酸ハロゲニドと
しては、シアン酢酸クロリド、シアン酢酸ブロマイド、
シアン酢酸ョーダィド、シアン酢酸フロラィドなどがあ
げられる。また反応に用いられる置換ホルムアミドとし
てはアルキル或いはアリルで置換されたホルムアミド、
たとえば、Ｎ，Ｎ．ジメチルホルムアミド、Ｎ，Ｎ−ジ
エチルホルムアミド、Ｎ，Ｎ−ジフ。ロピルホルムアミ
ド、Ｎ−メチル−Ｎ−エチルホルムアミド、Ｎ−メチル
−Ｎ−フエニルホルムアミド、Ｎ，Ｎージフエニルホル
ムアミドなどがあげられる。また本反応は置換ホルムア
ミド単独で反応溶媒に用いることもでき、或いは所望に
より本反応に障害とならない溶媒との混合溶媒中でみ実
施することができる。このような溶媒としては、一般に
有機溶媒が好ましく、たとえばベンゼン、トルェン、キ
シレン、石油エーテルなどの炭化水素類、テトラヒドロ
フラン、ジオキサン、エチルエーテル、エチレングリコ
ールジメチルヱーテルなどのエーテル類、クロロホルム
、ジク。メタン、ジクロルエタン、テトラクロルヱタン
などのハロゲン化された炭化水素類、酢酸エチル、酢酸
メチル、酢酸ブチルなどのェステル類、アセトン、メチ
ルエチルケトンなどのケトン類、アセトニトリル、ジメ
チルスルホキシドなどがあげられる。一般式（０）の製
造に用いられるシアン酢酸ハロゲニドの使用量は、通常
一般式（ｍ）の原料化合物１モルに対し、実用上約１〜
１０モル程度である。反応温度、反応時間などのその他
の反応条件に特に制限はないが、約２０〜約１２０３０
程度で約３０分間〜２日間程度反応させるのが一般的で
ある。また、置換ホルムァミドの使用量は特に制限はな
いが、一般式（ｍ）の原料化合物１モルに対し、２モル
程度以上使用するのが一般的である。かくして製造され
た一般式（ロ）の化合物は、薬効を有する化合物製造の
ための中間体として有用である。次にかくして製造され
た一般式（ロ）の化合物を加水分解処理をして一般式（
１）の化合物を製造することができる。That is, it is produced by reacting the compound of general formula (m) with cyanacetic acid halide in the presence of substituted formamide. Examples of cyanacetic acid halogenide used in the reaction include cyanacetic acid chloride, cyanacetic acid bromide,
Examples include cyanacetate iodide and cyanacetate fluoride. Substituted formamides used in the reaction include alkyl- or allyl-substituted formamides,
For example, N,N. Dimethylformamide, N,N-diethylformamide, N,N-diph. Examples include propylformamide, N-methyl-N-ethylformamide, N-methyl-N-phenylformamide, and N,N-diphenylformamide. Further, this reaction can be carried out using substituted formamide alone as a reaction solvent, or if desired, it can be carried out only in a mixed solvent with a solvent that does not interfere with this reaction. Such solvents are generally preferably organic solvents, such as hydrocarbons such as benzene, toluene, xylene, and petroleum ether, ethers such as tetrahydrofuran, dioxane, ethyl ether, and ethylene glycol dimethyl ether, chloroform, and dichloromethane. Examples include halogenated hydrocarbons such as methane, dichloroethane, and tetrachloroethane, esters such as ethyl acetate, methyl acetate, and butyl acetate, ketones such as acetone and methyl ethyl ketone, acetonitrile, and dimethyl sulfoxide. The amount of cyanacetic acid halide used in the production of general formula (0) is usually approximately 1 to 1 mol per mol of the raw material compound of general formula (m).
It is about 10 moles. Other reaction conditions such as reaction temperature and reaction time are not particularly limited, but about 20 to about 12030
Generally, the reaction is carried out for about 30 minutes to about 2 days. The amount of substituted formamide to be used is not particularly limited, but it is generally used in an amount of about 2 moles or more per 1 mole of the raw material compound of general formula (m). The compound of general formula (b) thus produced is useful as an intermediate for producing compounds having medicinal effects. Next, the compound of the general formula (b) thus produced was subjected to hydrolysis treatment to give a compound of the general formula (b).
The compound of 1) can be produced.
本反応における加水分解は酸性、アルカリ性いずれでも
よいが、とりわけ酸性で行なうのが好ましく、たとえば
塩酸、硫酸、過塩素酸などの鉱酸、トリフロロ酢酸、ギ
酸、酢酸などの有機酸などが使用し得る。本反応は一般
に、水の存在下に有機酸と滋酸との混合液中で実施する
のが好ましい。反応温度、反応時間など、その他の反応
条件に特に制限はないが、５０〜１５０℃程度で約１時
間〜２日間程度反応させるのが一般的である。かくして
製造された一般式（１）の化合物は、たとえばエタノー
ルアミン、ジェタノールアミン、ｄク−メチルエフヱド
リン、１−（３，５一ジヒドロキシフエニル）一Ｌ−イ
ソプロピルアミノエタノール、イソフ。ロテレノール、
デキストロメトルフアン、ヘトラザン（ジエチルァミン
，トリェチルアミンなどの有機ァミン類あるいはたとえ
ば水酸化ナトリウム、水酸化カリウムなどのアルカリ金
属の水酸化物あるいはアンモニアな！′と一般式（１）
の化合物とをたとえば両者を造ユの溶媒中で混合、加熱
するなど自体公知の方法で反応させることにより、一般
式（１）の化合物に対応する有機アミン塩、アルカリ金
属塩あるいはアンモニウム塩を得ることができる。かく
して製造される一般式（１）の化合物は抗アレルギー作
用を有し、たとえばアレルギー性端息、アレルギー性皮
フ炎、枯草熱などのアレルギー性疾患の予防、治療剤と
して有用である。一般式（１）の化合物をたとえば前記
のアレルギー疾患の予防、治療剤として用いる場合か、
成人投与量として通常約０．１〜５００の９／日程度を
錠剤、カプセル剤、散剤、水剤などとして経口投与する
ほか、注射剤、階霧吸入剤、軟膏剤などの適宜の剤型で
投与することができる。なお、本発明の原料化合物であ
る一般式（ｍ）合化合物は下記の方法によって製造する
ことができる。The hydrolysis in this reaction may be carried out under either acidic or alkaline conditions, but acidic conditions are particularly preferred; for example, mineral acids such as hydrochloric acid, sulfuric acid, and perchloric acid, and organic acids such as trifluoroacetic acid, formic acid, and acetic acid can be used. . This reaction is generally preferably carried out in a mixture of organic acid and hydrogenated acid in the presence of water. Other reaction conditions such as reaction temperature and reaction time are not particularly limited, but the reaction is generally carried out at about 50 to 150°C for about 1 hour to 2 days. Compounds of general formula (1) thus produced include, for example, ethanolamine, jetanolamine, d-methylephedrine, 1-(3,5-dihydroxyphenyl)-1L-isopropylaminoethanol, and isof. loterenol,
Dextromethorphan, hetrazan (organic amines such as diethylamine and triethylamine, or alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, or ammonia!' and the general formula (1)
The organic amine salt, alkali metal salt, or ammonium salt corresponding to the compound of general formula (1) is obtained by reacting the compound with the compound of formula (1) by a method known per se, such as by mixing the two in a solvent and heating. be able to. The compound of general formula (1) thus produced has an antiallergic effect and is useful as a prophylactic or therapeutic agent for allergic diseases such as allergic asthma, allergic dermatitis, and hay fever. For example, when the compound of general formula (1) is used as a prophylactic or therapeutic agent for the aforementioned allergic diseases,
The usual adult dosage is approximately 0.1 to 500 9/day administered orally in the form of tablets, capsules, powders, solutions, etc., as well as in appropriate dosage forms such as injections, inhalers, and ointments. can be administered. Note that the compound of general formula (m), which is the raw material compound of the present invention, can be produced by the following method.
すなわち、Ｊ．ＭＥｄ．Ｃｈｅｍ．２０，１４１（１９
７７）に開示された方法あるいはそれと同様の方法によ
って製造される一般式（Ｎ）〔式中、Ａ環は前記と同意
菱を表わす〕の化合物を、塩基の存在下に水と反応させ
ることにより、一般式（ｍ）で示される化合物が製造さ
れる。That is, J. MEd. Chem. 20,141 (19
77) or a method similar thereto, by reacting a compound of general formula (N) [wherein A ring represents the same diamond as above] with water in the presence of a base. , a compound represented by general formula (m) is produced.
反応に用いられる塩基としては有機ァミン類が、例えば
エチルアミン、ｎープロピルアミン，ｎーブチルアミン
、ベンジルアミン、アニリン等一級アミンやジメチルア
ミン、ジェチルアミン、ジプロピルアミン、ジブチルア
ミン、モルホリン、ピベリジン、ピロリジン等の二級ア
ミンや、トリェチルアミンのような三級アミン、イミダ
ゾール、２ーメチルアミダゾールのような異境環塩基や
、アンモニア水、酢酸アンモニウム、炭酸アンモニウム
、炭酸ナトリウム、炭酸水素ナトリウムのような無機の
塩基があげられる。これらの塩基は触媒量から大過剰ま
で使用することができ、特に制限はない。反応は一般に
水と混和する溶媒中で行うのが好ましく、例えばジメチ
ルホルムアミド、ジメチルスルホキド、ヘキサメチルリ
ン酸トリアミドや、ギ酸、酢酸、プロピオン酸等の有機
酸額や、テトラヒドロフラン、ジオキサン等のエーテル
類があげられる。The bases used in the reaction include organic amines, such as primary amines such as ethylamine, n-propylamine, n-butylamine, benzylamine, and aniline, and secondary amines such as dimethylamine, diethylamine, dipropylamine, dibutylamine, morpholine, piberidine, and pyrrolidine. Examples include amines, tertiary amines such as triethylamine, exotic bases such as imidazole and 2-methylamidazole, and inorganic bases such as aqueous ammonia, ammonium acetate, ammonium carbonate, sodium carbonate, and sodium bicarbonate. . These bases can be used in a catalytic amount to a large excess, and are not particularly limited. The reaction is generally preferably carried out in a solvent that is miscible with water, such as dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, organic acids such as formic acid, acetic acid, and propionic acid, and ethers such as tetrahydrofuran and dioxane. can be given.
反応温度、反応温度などその他の反応条件に特に制限は
ないが、約２０〜１００００程度で数分間〜３時間程度
反応させるのが一般的である。以下に、参考例および実
施例を挙げて本発明をより具体的に説明する。参考例
１
モルホリン２の‘、ジメチルホルムアミド３の【、水１
０机上の涙液を６０００に加溢し、かきまぜあがら粉末
化した４−オキシ−４Ｈ−１ーベンゾピラン−３−カル
ボニトリル１．７１夕を５分間かかって添加した。Although there are no particular limitations on other reaction conditions such as reaction temperature, reaction temperature is generally about 20 to about 10,000 and the reaction is carried out for several minutes to about 3 hours. The present invention will be described in more detail below with reference to Reference Examples and Examples. Reference example
1 morpholine 2 ', dimethylformamide 3 [, water 1
The lacrimal fluid on the table was brought to 6,000 ml, and while stirring, 1.71 ml of powdered 4-oxy-4H-1-benzopyran-3-carbonitrile was added over 5 minutes.
そのまま１時間加湿したのち、析出物をろ取し、水洗後
、酢酸から再結晶し、クロロホルムで洗族すると、２−
アミノ−４−オキソ−４Ｈ−１−ペンゾピラン−３−カ
ルボキサアルデヒドの結晶１．３２夕が得られた。融点
２５２−２５５００（分解）核磁気共鳴スペクトル（Ｄ
ＭＳＯ−ｄ６）６：１０．１９（ＩＨ，ｓ），９．６７
（Ｃａｌ．凪，ｂｒ，ｓ），８．１１（ＩＨ，ｄｄ，Ｊ
＝２．８１Ｚ），７．９７−７．８０（３日，ｍ）元素
分析 Ｃ，虹７Ｎ０３として計算値：Ｃ，６３．４９：
日，３．７３：Ｎ，７．４１実験値：Ｃ，６３．５９；
日，３．４４；Ｎ，７．４５以下同様にして次の化合式
を得た。After humidifying for 1 hour, the precipitate was collected by filtration, washed with water, recrystallized from acetic acid, and washed with chloroform to obtain 2-
1.32 crystals of amino-4-oxo-4H-1-penzopyran-3-carboxaldehyde were obtained. Melting point 252-25500 (decomposed) nuclear magnetic resonance spectrum (D
MSO-d6) 6:10.19 (IH, s), 9.67
(Cal. Nagi, br, s), 8.11 (IH, dd, J
=2.81Z), 7.97-7.80 (3 days, m) Elemental analysis C, Calculated value as Rainbow 7N03: C, 63.49:
Day, 3.73: N, 7.41 Experimental value: C, 63.59;
Day, 3.44; N, 7.45 The following compound formula was obtained in the same manner.
２−アミノ−６−エチル−４−キキソ−４Ｈ−１−ペン
ゾピラン−３−カルボキサアルデヒド１．８２夕をジメ
チルホルムアミド１４０の‘にとかし、ついで、ジアノ
アセチルクロリド３．５夕を加え、６０ｏｏ、３時間、
かくはんしながら反応させたのち、減圧下溶媒を留去し
、残留物をシリカゲルラムクロマトに付し、クロロホル
ム熔出部より目的物を得た。1.82 ml of 2-amino-6-ethyl-4-xo-4H-1-penzopyran-3-carboxaldehyde was dissolved in 140 ml of dimethylformamide, and then 3.5 ml of dianoacetyl chloride was added to give 60 ml of 2-amino-6-ethyl-4-xo-4H-1-penzopyran-3-carboxaldehyde. , 3 hours,
After reacting with stirring, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography to obtain the desired product from the chloroform elution section.
アセトニトリルより再結晶し、７−エチル−３ーシアノ
ー１−アザキサントン１．０３夕を得た。融点１８３〜
１８５００同様にして、以下の化合物を得た。Recrystallization from acetonitrile gave 1.03 g of 7-ethyl-3-cyano-1-azaxanthone. Melting point 183~
The following compounds were obtained in the same manner as 18500.
７ーメチル−３−シアノー１ーアザキサントン融点２４
０−２４２００（再結晶溶媒：エタノール），３ーシア
ノー１−アザキサントン 融点２２０一２２６℃（再結
晶溶媒：エタノール），７ーイソプロピル−３ーシァノ
−１−アザキサントン 融点２０６−２０５午Ｃ（再結
晶溶媒：エタノール），７−クロル−３−シアノ−１ー
アザキサントン 融点２８６−２８８つ０再結晶溶媒：
ジメチルホルムアミド），７，９ージメチル−３−シア
ノ−１−アザキサントン融点２５４−２５７℃再結晶溶
媒：アセトニトリル）。7-Methyl-3-cyano 1-azaxanthone Melting point 24
0-24200 (recrystallization solvent: ethanol), 3-cyano-1-azaxanthone melting point 220-226℃ (recrystallization solvent: ethanol), 7-isopropyl-3-cyano-1-azaxanthone melting point 206-205℃ (recrystallization solvent : ethanol), 7-chloro-3-cyano-1-azaxanthone Melting point 286-288 0 Recrystallization solvent:
dimethylformamide), 7,9-dimethyl-3-cyano-1-azaxanthone melting point 254-257°C recrystallization solvent: acetonitrile).
７−ｔーブチル−３−シアノー１−アザキサントン 融
点２４７−２４９００再結晶溶媒：アセトニトＩＪル）
実施例 ２７ーイソプロピルー３−シアノー１−アザキ
サントン０．８７５９を５０％硫酸水溶液１０地、酢酸
ｌｏｗ‘とからなる混液中で、かくはんしながら１２０
ｑＣ、２時間反応する。7-tert-butyl-3-cyano-1-azaxanthone Melting point 247-24900 Recrystallization solvent: acetonitol)
Example 27-Isopropyl-3-cyano-1-azaxanthone 0.8759 was added to 120% of a 50% aqueous sulfuric acid solution and 120% of acetic acid with stirring.
qC, react for 2 hours.
反応後、反応液に水を加え、析出する沈澱を炉取し、こ
れを水洗、乾燥した後、エタノールから再結晶、７−イ
ソプロピル−１ーアザキサントン−３−カルポン酸を０
．６２３タ得た。融点２５９−２６１００。同様にして
以下の化合物を得た。After the reaction, water was added to the reaction solution, the precipitate was collected in an oven, washed with water, dried, and then recrystallized from ethanol to remove 7-isopropyl-1-azaxanthone-3-carboxylic acid.
．． I got 623 ta. Melting point 259-26100. The following compounds were obtained in the same manner.
１−アザキサントン−３ーカルボン酸、融点２６７−２
６９ｑｏ（再結晶溶媒：酢酸エチル），７−ェチル−１
ーアザキサントンー３−カルボン酸，融点２３８一２３
９ｑｏ（再結晶溶媒：ジメチルホルムアミド）。1-azaxanthone-3-carboxylic acid, melting point 267-2
69qo (recrystallization solvent: ethyl acetate), 7-ethyl-1
-Azaxanthone-3-carboxylic acid, melting point 238-23
9qo (recrystallization solvent: dimethylformamide).
Claims (1)
ルキル基で置換されていてもよい〕で示される化合物に
、置換ホルムアミドの存在下にシアン酢酸ハロゲニドを
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、Ａ環は前記と同意義を表わす〕で示される３
−シアノ−１−アザキサントン誘導体の製造法。 ２ 一般式 ▲数式、化学式、表等があります▼ 〔式中、Ａ環はハロゲン原子または炭素数１〜６のア
ルキル基で置換されていてもよい〕で示される化合物に
置換ホルムアミドの存在下にシアン酢酸ハロゲニドを反
応させ、一般式 ▲数式、化学式、表等があります▼ 〔式中、Ａ環は前記と同意義を表わす〕で示される化
合物とし、これを加水分解す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、Ａ環は前
記と同意義を表わす〕で示される１−アザキサントン−
３−カルボン酸誘導体の製造法。[Claims] 1 A compound represented by the general formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, ring A may be substituted with a halogen atom or an alkyl group having 1 to 6 carbon atoms] , a general formula characterized by reacting cyanacetic acid halide in the presence of substituted formamide ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, ring A represents the same meaning as above] 3
-Production method of cyano-1-azaxanthone derivative. 2. In the presence of substituted formamide, a compound represented by the general formula ▲ includes mathematical formulas, chemical formulas, tables, etc. A general method characterized by reacting cyanacetic acid halide to form a compound represented by the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, ring A represents the same meaning as above], and hydrolyzing this 1-azaxanthone- represented by the formula ▲ Numerical formulas, chemical formulas, tables, etc. ▼ [In the formula, ring A represents the same meaning as above]
Method for producing 3-carboxylic acid derivative.
Priority Applications (23)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15389877A JPS6034555B2 (en) | 1977-12-20 | 1977-12-20 | Method for producing 1-azaxanthone derivative |
| AU33646/78A AU513456B2 (en) | 1977-03-08 | 1978-02-27 | l-Azaxanthone-3-carboxylic acids |
| CA297,785A CA1087188A (en) | 1977-03-08 | 1978-02-27 | 1-azaxanthone-3-carboxylic acids |
| US05/881,237 US4143042A (en) | 1977-03-08 | 1978-02-27 | 1-azaxanthone-3-carboxylic acids |
| DK092478A DK156661C (en) | 1977-03-08 | 1978-03-01 | ANALOGY PROCEDURE FOR THE PREPARATION OF 1-AZAXANTON-3-CARBOXYLIC ACIDS |
| AT149978A AT360535B (en) | 1977-03-08 | 1978-03-02 | METHOD FOR PRODUCING NEW 1-AZAXANTHON-3-CARBONIC ACIDS AND THEIR SALTS |
| GB3085079A GB1597025A (en) | 1977-03-08 | 1978-03-03 | 1-azaxanthone derivatives |
| GB8518/78A GB1597024A (en) | 1977-03-08 | 1978-03-03 | 1-azaxanthone-3-carboxylic acids |
| GR55623A GR64459B (en) | 1977-03-08 | 1978-03-06 | Method for the preparation of t-azaxanthono-3-carboxylic acids |
| SU782587760A SU812178A3 (en) | 1977-03-08 | 1978-03-06 | Method of preparing derivatives of 1-azaxanthon-3-carboxylic acid of their salts with aliphatic amines |
| BE185734A BE864647A (en) | 1977-03-08 | 1978-03-07 | 1-AZAXANTHONE-3-CARBOXYLIC ACID AND ITS DERIVATIVES |
| FR7806538A FR2383185B1 (en) | 1977-03-08 | 1978-03-07 | |
| NO780777A NO149737C (en) | 1977-03-08 | 1978-03-07 | ANALOGY PROCEDURE FOR THE PREPARATION OF THERAPEUTIC ACTIVE 1-AZAXANTHON-3-CARBOXYLIC ACIDS |
| IT20957/78A IT1109830B (en) | 1977-03-08 | 1978-03-07 | DERIVATIVES OF 1-AZAXANTONE-3-CARBOXYLIC ACID AND PROCEDURE FOR THEIR PREPARATION |
| HUTA001477 HU179595B (en) | 1977-03-08 | 1978-03-07 | Process for producing 1-azaxantone-3-carboxylic acid derivatives |
| CH248678A CH634322A5 (en) | 1977-03-08 | 1978-03-07 | 1-AZAXANTHON-3-CARBONIC ACIDS AND METHOD FOR THE PRODUCTION THEREOF. |
| DE19782809720 DE2809720A1 (en) | 1977-03-08 | 1978-03-07 | 1-AZAXANTHONE-3-CARBONIC ACIDS AND THE PROCESS FOR THEIR PRODUCTION |
| SE7802609A SE439309B (en) | 1977-03-08 | 1978-03-07 | ANALOGY PROCEDURE FOR PREPARATION OF 1-AZAXANTON-3-CARBOXYLIC ACID DERIVATIVES |
| NLAANVRAGE7802526,A NL188645C (en) | 1977-03-08 | 1978-03-08 | 1-AZAXANTHON-3-CARBONIC ACID COMPOUNDS AND PHARMACEUTICAL PREPARATIONS CONTAINING THESE COMPOUNDS. |
| ES468042A ES468042A1 (en) | 1977-03-08 | 1978-03-08 | 1-azaxanthone-3-carboxylic acids |
| US05/970,105 US4255576A (en) | 1977-03-08 | 1978-12-18 | 1-Azaxanthone derivatives |
| US06/177,580 US4299963A (en) | 1977-03-08 | 1980-08-13 | 1-Azaxanthone derivatives |
| HK279/84A HK27984A (en) | 1977-03-08 | 1984-03-22 | 1-azaxanthone-3-carboxylic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15389877A JPS6034555B2 (en) | 1977-12-20 | 1977-12-20 | Method for producing 1-azaxanthone derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5488298A JPS5488298A (en) | 1979-07-13 |
| JPS6034555B2 true JPS6034555B2 (en) | 1985-08-09 |
Family
ID=15572511
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15389877A Expired JPS6034555B2 (en) | 1977-03-08 | 1977-12-20 | Method for producing 1-azaxanthone derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6034555B2 (en) |
-
1977
- 1977-12-20 JP JP15389877A patent/JPS6034555B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5488298A (en) | 1979-07-13 |
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