JPS6247460B2 - - Google Patents
Info
- Publication number
- JPS6247460B2 JPS6247460B2 JP11003080A JP11003080A JPS6247460B2 JP S6247460 B2 JPS6247460 B2 JP S6247460B2 JP 11003080 A JP11003080 A JP 11003080A JP 11003080 A JP11003080 A JP 11003080A JP S6247460 B2 JPS6247460 B2 JP S6247460B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- methanol
- alkoxycarbonyl
- substituent
- 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
- -1 cyclohexyloxycarbonyl group Chemical group 0.000 claims description 27
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- KBUWQCXQODASRJ-UHFFFAOYSA-N 6-hydroxy-5-methyl-1h-pyridin-2-one Chemical compound CC1=CC=C(O)N=C1O KBUWQCXQODASRJ-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000007865 diluting Methods 0.000 description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- MGMQOCFXXSNULH-UHFFFAOYSA-N 5-ethyl-6-hydroxy-1h-pyridin-2-one Chemical compound CCC=1C=CC(=O)NC=1O MGMQOCFXXSNULH-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
Description
本発明はピラゾロアザキサンテノイソキノリノ
ン類に関するものである。
本発明の下記一般式〔〕
(式中、R1は水素原子、アルキル基、トリフルオ
ロメチル基、アルコキシカルボニル基、アルコキ
シカルボニルアルキル基、アラルキル基、または
フエニル基を表わし、R2は置換基を有していて
もよいアルコキシカルボニル基、シクロヘキシル
オキシカルボニル基、テトラヒドロフルフリルオ
キシカルボニル基、アリールオキシカルボニル
基、ベンジルオキシカルボニル基、アシル基、シ
アノ基または置換基を有していてもよいカルバモ
イル基を表わし、R3は低級アルキル基を表わ
す。)で示されるピラゾロアザキサンテノイソキ
ノリノン類はそれ自体新規な極めて強い螢光を有
する化合物であり、染料あるいは染料として価値
のあるものである。
本発明を詳細に説明するに、本発明の化合物は
たとえば、
一般式〔〕
(式中、R1およびR2は前示一般式〔〕における
と同一の意義を有し、Xはハロゲン原子を表わ
す。)で示されるジハロゲノベンゾピラゾロイソ
キノリノン類をN−メチル−2−ピロリドン、
N・N−ジメチルホルムアミド、キノリン等の反
応に不活性な有機溶媒中、所望により、炭酸ナト
リウム、炭酸カリウム、トリエチルアミン等の脱
酸剤の存在下に、下記一般式〔〕
(式中、R3は前示一般式〔〕におけると同一の
意義を有する。)で示されるピリドン類と100〜
200℃、好ましくは140〜160℃の温度条件下に反
応させることによつて製造される。
反応生成物は、場合により、メタノール、水等
で希釈することにより、容易に結晶として単離す
ることができる。
一般式〔〕および〔〕においてR1で表わ
さされる置換基としては、たとえば、水素原子;
メチル基、エチル基、プロピル基、ブチル基、ヘ
キシル基、オクチル基等のアルキル基;トリフル
オロメチル基;メトキシカルボニル基、エトキシ
カルボニル基、プロポキシカルボニル基、ブトキ
シカルボニル基等のアルコキシカルボニル基;メ
トキシカルボニルメチル基、エトキシカルボニル
メチル基、プロポキシカルボニルメチル基、ブト
キシカルボニルメチル基等のアルコキシカルボニ
ルアルキル基;フエニル基;ベンジル基、フエネ
チル基等のアラルキル基が挙げられ、R2として
は、メトキシカルボニル基、エトキシカルボニル
基、プロポキシカルボニル基、ブトキシカルボニ
ル基、ヘキシルオキシカルボニル基、オクチルオ
キシカルボニル基等のアルコキシカルボニル基;
メトキシエトキシカルボニル基、エトキシエトキ
シカルボニル基、プロポキシエトキシカルボニル
基、ブトキシエトキシカルボニル基、メトキシプ
ロポキシカルボニル基、メトキシエトキシエトキ
シカルボニル基、エトキシエトキシエトキシカル
ボニル基、プロポキシエトキシエトキシカルボニ
ル基、ブトキシエトキシエトキシカルボニル基、
ジメチルアミノエトキシカルボニル基、ジエチル
アミノエトキシカルボニル基等のアルコキシ基、
アルコキシアルコキシ基、アルキルアミノ基など
により置換されているアルコキシカルボニル基;
シクロヘキシルオキシカルボニル基;テトラヒド
ロフルフリルオキシカルボニル基;ベンジルオキ
シカルボニル基;トリルオキシカルボニル基、フ
エノキシカルボニル基等のアリ−ロキシカルボニ
ル基;アセチル基、ベンゾイル基、チエノイル基
等のアシル基;シアノ基;カルバモイル基;フエ
ニルカルバモイル基、メチルカルバモイル基、エ
チルカルバモイル基、プロピルカルバモイル基、
ブチルカルバモイル基、ジメチルカルバモイル
基、ジエチルカルバモイル基、モルホリノカルボ
ニル基等の置換カルバモイル基が挙げられる。
一般式〔〕および〔〕においてR3で表わ
される置換基としては、メチル基、エチル基、直
鎖状または分岐鎖状のプロピル基、ブチル基が挙
げられる。また一般式〔〕においてXで表わさ
れる置換基としては塩素原子、臭素原子が挙げら
れる。
以下に本発明を実施例によつて更に具体的に説
明する。
実施例 1
下記構造式
で示される化合物20.4gおよび3−シアノ−4−
メチル−6−ヒドロキシ−2−ピリドン7.5gを
N−メチルピロリドン150ml中、炭酸カリウム6.9
gの存在下に160℃で1時間加熱した。冷却後、
メタノールで希釈して析出物を取し、メタノー
ル、水で洗浄して乾燥することにより、下記構造
式
The present invention relates to pyrazoloazaxanthenoisoquinolinones. The following general formula of the present invention [] (In the formula, R 1 represents a hydrogen atom, an alkyl group, a trifluoromethyl group, an alkoxycarbonyl group, an alkoxycarbonylalkyl group, an aralkyl group, or a phenyl group, and R 2 represents an alkoxycarbonyl group that may have a substituent. R 3 represents a lower alkyl group, a cyclohexyloxycarbonyl group, a tetrahydrofurfuryloxycarbonyl group, an aryloxycarbonyl group, a benzyloxycarbonyl group, an acyl group, a cyano group, or a carbamoyl group which may have a substituent. The pyrazoloazaxanthenoisoquinolinones represented by the following formula are themselves novel compounds with extremely strong fluorescence, and are valuable as dyes or dyes. To explain the present invention in detail, the compound of the present invention has the general formula [] (In the formula, R 1 and R 2 have the same meanings as in the above general formula [], and X represents a halogen atom.) 2-pyrrolidone,
In an organic solvent inert to the reaction such as N/N-dimethylformamide or quinoline, optionally in the presence of a deoxidizing agent such as sodium carbonate, potassium carbonate or triethylamine, the following general formula [] (In the formula, R 3 has the same meaning as in the general formula []) and pyridones of 100 to
It is produced by reacting at a temperature of 200°C, preferably 140-160°C. The reaction product can be easily isolated as crystals by diluting it with methanol, water, etc., as the case may be. Examples of the substituent represented by R 1 in the general formulas [] and [] include a hydrogen atom;
Alkyl groups such as methyl group, ethyl group, propyl group, butyl group, hexyl group, octyl group; trifluoromethyl group; alkoxycarbonyl group such as methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, butoxycarbonyl group; methoxycarbonyl Examples include alkoxycarbonylalkyl groups such as methyl group, ethoxycarbonylmethyl group, propoxycarbonylmethyl group, butoxycarbonylmethyl group; phenyl group; aralkyl groups such as benzyl group and phenethyl group; R 2 is methoxycarbonyl group, ethoxy Alkoxycarbonyl groups such as carbonyl group, propoxycarbonyl group, butoxycarbonyl group, hexyloxycarbonyl group, octyloxycarbonyl group;
methoxyethoxycarbonyl group, ethoxyethoxycarbonyl group, propoxyethoxycarbonyl group, butoxyethoxycarbonyl group, methoxypropoxycarbonyl group, methoxyethoxyethoxycarbonyl group, ethoxyethoxyethoxycarbonyl group, propoxyethoxyethoxycarbonyl group, butoxyethoxyethoxycarbonyl group,
Alkoxy groups such as dimethylaminoethoxycarbonyl group and diethylaminoethoxycarbonyl group,
an alkoxycarbonyl group substituted with an alkoxyalkoxy group, an alkylamino group, etc.;
Cyclohexyloxycarbonyl group; Tetrahydrofurfuryloxycarbonyl group; Benzyloxycarbonyl group; Aryloxycarbonyl group such as tolyloxycarbonyl group and phenoxycarbonyl group; Acyl group such as acetyl group, benzoyl group, and thienoyl group; Cyano group ;Carbamoyl group; phenylcarbamoyl group, methylcarbamoyl group, ethylcarbamoyl group, propylcarbamoyl group,
Examples include substituted carbamoyl groups such as a butylcarbamoyl group, a dimethylcarbamoyl group, a diethylcarbamoyl group, and a morpholinocarbonyl group. Examples of the substituent represented by R 3 in the general formulas [] and [] include a methyl group, an ethyl group, a linear or branched propyl group, and a butyl group. Further, examples of the substituent represented by X in the general formula [] include a chlorine atom and a bromine atom. The present invention will be explained in more detail below using Examples. Example 1 Structural formula below 20.4g of the compound shown and 3-cyano-4-
7.5 g of methyl-6-hydroxy-2-pyridone in 150 ml of N-methylpyrrolidone, 6.9 g of potassium carbonate
The mixture was heated at 160° C. for 1 hour in the presence of g. After cooling,
By diluting with methanol to remove the precipitate, washing with methanol and water, and drying, the following structural formula is obtained.
【式】および[expression] and
【式】
で示される化合物(赤色結晶)12.5gを得た。更
にN・N−ジメチルホルムアミドにより再結晶精
製し融点320℃以上の赤色結晶を得た。
元素分析値12.5 g of a compound represented by the formula (red crystals) was obtained. Further recrystallization purification was performed using N.N-dimethylformamide to obtain red crystals with a melting point of 320°C or higher. Elemental analysis value
【表】
マススペクトルの親イオンピークm/e=484
本実施例で得られた化合物はN・N−ジメチルホ
ルムアミド溶液中、極めて強い赤色螢光を示し
た。
実施例 2
下記構造式
で示される化合物20.1gおよび3−シアノ−4−
エチル−6−ヒドロキシ−2−ピリドン8.2gを
キノリン150ml中で160℃、3時間加熱した。冷却
後メタノールで希釈して析出物を取し、メタノ
ール、水で洗浄して乾燥することにより、下記構
造式[Table] Parent ion peak of mass spectrum m/e = 484
The compound obtained in this example exhibited extremely strong red fluorescence in N·N-dimethylformamide solution. Example 2 Structural formula below 20.1g of the compound shown and 3-cyano-4-
8.2 g of ethyl-6-hydroxy-2-pyridone was heated in 150 ml of quinoline at 160°C for 3 hours. After cooling, dilute with methanol to remove the precipitate, wash with methanol and water, and dry to obtain the following structural formula.
【式】および[expression] and
【式】
で示される化合物(赤色結晶)11.3gを得た。更
にN・N−ジメチルホルムアミドで再結晶精製す
ることにより融点320℃以上の赤色結晶を得た。
元素分析値11.3 g of a compound represented by the formula (red crystals) was obtained. Further recrystallization purification with N.N-dimethylformamide gave red crystals with a melting point of 320°C or higher. Elemental analysis value
【表】
マススペクトルの親イオンピークm/e=494
本実施例で得られた化合物は、N・N−ジメチ
ルホルムアミド溶液中、極めて強い赤色螢光を示
した。
実施例 3
下記構造式
で示される化合物27.9gおよび3−シアノ−4−
メチル−6−ヒドロキシ−2−ピリドン7.5gを
N−メチルピロリドン150ml中、炭酸カリウム6.9
gの存在下に160℃で1時間加熱した。冷却後、
メタノールで希釈して析出物を取し、メタノー
ル、水で洗浄して乾燥することにより下記構造式[Table] Parent ion peak of mass spectrum m/e = 494 The compound obtained in this example exhibited extremely strong red fluorescence in N·N-dimethylformamide solution. Example 3 Structural formula below 27.9g of the compound shown and 3-cyano-4-
7.5 g of methyl-6-hydroxy-2-pyridone in 150 ml of N-methylpyrrolidone, 6.9 g of potassium carbonate
The mixture was heated at 160° C. for 1 hour in the presence of g. After cooling,
The following structural formula was obtained by diluting with methanol to remove the precipitate, washing with methanol and water, and drying.
【式】および[expression] and
【式】
で示される化合物(赤色結晶)16.2gを得た。更
に、N・N−ジメチルホルムアミドで再結晶精製
して融点320℃以上の赤色結晶を得た。
元素分析値16.2 g of the compound represented by the formula (red crystals) was obtained. Further, the product was purified by recrystallization with N.N-dimethylformamide to obtain red crystals with a melting point of 320°C or higher. Elemental analysis value
【表】
マススペクトルの親イオンピークm/e=546
本実施例で得られた化合物は、N・N−ジメチ
ルホルムアミド溶液中、極めて強い赤色螢光を示
した。
実施例 4
下記構造式
で示される化合物17.2gおよび3−シアノ−4−
メチル−6−ヒドロキシ−2−ピリドン7.5gを
N−メチルピロリドン150ml中、炭酸ナトリウム
5.3gの存在下に160℃で1時間加熱した。冷却
後、メタノールで希釈して析出物を取し、メタ
ノール、水で洗浄して乾燥することにより下記構
造式[Table] Mass spectrum parent ion peak m/e = 546 The compound obtained in this example exhibited extremely strong red fluorescence in an N.N-dimethylformamide solution. Example 4 Structural formula below 17.2g of the compound shown and 3-cyano-4-
Add 7.5 g of methyl-6-hydroxy-2-pyridone to 150 ml of N-methylpyrrolidone in sodium carbonate.
Heated at 160° C. for 1 hour in the presence of 5.3 g. After cooling, dilute with methanol to remove the precipitate, wash with methanol and water, and dry to obtain the following structural formula.
【式】および[expression] and
【式】
で示される化合物(赤色結晶)10.6gを得た。更
に、N・N−ジメチルホルムアミドで再結晶精製
して融点320℃以上の赤色結晶を得た。
元素分析値10.6 g of a compound represented by the formula (red crystals) was obtained. Further, the product was purified by recrystallization with N.N-dimethylformamide to obtain red crystals with a melting point of 320°C or higher. Elemental analysis value
【表】
マススペクトルの親イオンピークm/e=422
本実施例で得られた化合物はN・N−ジメチル
ホルムアミド溶液中、極めて強い赤色螢光を示し
た。
実施例 5
前記実施例に準じた方法により表−1に示す化
合物を得た。
各々の化合物はN・N−ジメチルホルムアミド
溶中、同表のとおり、極めて強い螢光性色調を示
した。[Table] Parent ion peak of mass spectrum m/e = 422 The compound obtained in this example exhibited extremely strong red fluorescence in N·N-dimethylformamide solution. Example 5 The compounds shown in Table 1 were obtained by a method similar to the above example. As shown in the same table, each compound exhibited an extremely strong fluorescent color tone when dissolved in N.N-dimethylformamide.
【表】【table】
【表】【table】
Claims (1)
ロメチル基、アルコキシカルボニル基、アルコキ
シカルボニルアルキル基、アラルキル基またはフ
エニル基を表わし、R2は置換基を有していても
よいアルコキシカルボニル基、シクロヘキシルオ
キシカルボニル基、テトラヒドロフルフリルオキ
シカルボニル基、アリールオキシカルボニル基、
ベンジルオキシカルボニル基、アシル基、シアノ
基または置換基を有していてもよいカルバモイル
基を表わし、R3は低級アルキル基を表わす。)で
示されるピラゾロアザキサンテノイソキノリノン
類。[Claims] 1 General formula [Formula] or [Formula] (wherein R 1 represents a hydrogen atom, an alkyl group, a trifluoromethyl group, an alkoxycarbonyl group, an alkoxycarbonylalkyl group, an aralkyl group, or a phenyl group; , R 2 is an alkoxycarbonyl group that may have a substituent, a cyclohexyloxycarbonyl group, a tetrahydrofurfuryloxycarbonyl group, an aryloxycarbonyl group,
It represents a benzyloxycarbonyl group, an acyl group, a cyano group, or a carbamoyl group which may have a substituent, and R 3 represents a lower alkyl group. ) pyrazoloazaxanthenoisoquinolinones.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11003080A JPS5734163A (en) | 1980-08-11 | 1980-08-11 | Pyrazoloazaxanthenoisoquinolinone |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11003080A JPS5734163A (en) | 1980-08-11 | 1980-08-11 | Pyrazoloazaxanthenoisoquinolinone |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5734163A JPS5734163A (en) | 1982-02-24 |
JPS6247460B2 true JPS6247460B2 (en) | 1987-10-08 |
Family
ID=14525324
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP11003080A Granted JPS5734163A (en) | 1980-08-11 | 1980-08-11 | Pyrazoloazaxanthenoisoquinolinone |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5734163A (en) |
-
1980
- 1980-08-11 JP JP11003080A patent/JPS5734163A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS5734163A (en) | 1982-02-24 |
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