JPH0240672B2 - 55FUENIRUAMINOO11FUENIRUU1HHPIRAZORO * 3 * 44B * PIRAJINJUDOTAI - Google Patents
55FUENIRUAMINOO11FUENIRUU1HHPIRAZORO * 3 * 44B * PIRAJINJUDOTAIInfo
- Publication number
- JPH0240672B2 JPH0240672B2 JP6367582A JP6367582A JPH0240672B2 JP H0240672 B2 JPH0240672 B2 JP H0240672B2 JP 6367582 A JP6367582 A JP 6367582A JP 6367582 A JP6367582 A JP 6367582A JP H0240672 B2 JPH0240672 B2 JP H0240672B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- phenyl
- formula
- pyrazolo
- pyrazine
- 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 - Lifetime
Links
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- STGNILCSAZFXAH-UHFFFAOYSA-N n,1-diphenylpyrazolo[3,4-b]pyrazin-5-amine Chemical class C=1N=C2N(C=3C=CC=CC=3)N=CC2=NC=1NC1=CC=CC=C1 STGNILCSAZFXAH-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 10
- 230000000259 anti-tumor effect Effects 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QSXRUMZWAOWFCH-UHFFFAOYSA-N 5-chloro-1-phenylpyrazolo[3,4-b]pyrazine Chemical compound N1=CC2=NC(Cl)=CN=C2N1C1=CC=CC=C1 QSXRUMZWAOWFCH-UHFFFAOYSA-N 0.000 description 3
- 239000002246 antineoplastic agent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- ZKNORTOOYUPROW-UHFFFAOYSA-N 1-phenylpyrazolo[3,4-b]pyrazine Chemical class C12=NC=CN=C2C=NN1C1=CC=CC=C1 ZKNORTOOYUPROW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- -1 methoxy, ethoxy, propoxy, butoxy, pentyloxy Chemical group 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZVNYYNAAEVZNDW-UHFFFAOYSA-N 2-phenylpyrazol-3-amine Chemical compound NC1=CC=NN1C1=CC=CC=C1 ZVNYYNAAEVZNDW-UHFFFAOYSA-N 0.000 description 1
- NDWSQHPRNWYCAH-UHFFFAOYSA-N 2-phenylpyrazole-3,4-diamine Chemical compound NC1=C(N)C=NN1C1=CC=CC=C1 NDWSQHPRNWYCAH-UHFFFAOYSA-N 0.000 description 1
- GLKNSXRJKZBVGW-UHFFFAOYSA-N 4-nitroso-2-phenylpyrazol-3-amine;hydrochloride Chemical compound Cl.NC1=C(N=O)C=NN1C1=CC=CC=C1 GLKNSXRJKZBVGW-UHFFFAOYSA-N 0.000 description 1
- LGTJKUYVFSBOMC-UHFFFAOYSA-N 5-phenyl-1h-pyrazole-4-carboxylic acid Chemical compound C1=NNC(C=2C=CC=CC=2)=C1C(=O)O LGTJKUYVFSBOMC-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
本発明は、優れた抗腫瘍作用を有する下記式(1)
（但し、R1はフエニル基又はその水素原子の１
又は２以上をハロゲン原子、低級アルキル基、低
級アルコキシ基もしくはニトロ基により置換され
たフエニル基を示し、R2は水素原子又はメチル
基を示す。）
で示される新規５―フエニルアミノ―１―フエニ
ル―1H―ピラゾロ〔３，４―ｂ〕ピラジン誘導
体に関する。
従来より、抗腫瘍作用を有する種々の物質が開
発され、提案されているが、本発明者らも抗腫瘍
作用に優れ、抗腫瘍剤として好適に使用すること
ができる化合物につき鋭意研究を行なつているう
ち、５―クロロ―１―フエニル―1H―ピラゾロ
〔３，４―ｂ〕ピラジンをアニリン誘導体と反応
させる等の方法により、前記(1)式で示される新規
化合物５―フエニルアミノ―１―フエニル―1H
―ピラゾロ〔３，４―ｂ〕ピラジン誘導体が得ら
れると共に、これらの化合物が優れた抗腫瘍作用
を有し、抗腫瘍剤として効果的に使用され得るこ
とを知見し、本発明をなすに至つた。
以下、本発明につき更に詳しく説明する。
本発明に係る新規化合物５―フエニルアミノ―
１―フエニル―1H―ピラゾロ〔３，４―ｂ〕ピ
ラジン誘導体は、上述した(1)式、即ち
（但し、R1はフエニル基又はその水素原子の１
又は２以上をフツ素、塩素、臭素、ヨウ素といつ
たハロゲン原子、低級アルキル基、低級アルコキ
シ基もしくはニトロ基により置換されたフエニル
基を示し、R2は水素原子又はメチル基を示す。）
で示される化学構造式を有するものである。
ここで(1)式において、低級アルキル基として
は、メチル基、エチル基、プロピル基、イソプロ
ピル基、ブチル基、イソブチル基、ペンチル基、
イソペンチル基、ネオペンチル基等の炭素数１〜
６の直鎖又は分枝鎖のものが挙げられる。
また、低級アルコキシ基としては、メトキシ
基、エトキシ基、プロポキシ基、ブトキシ基、ペ
ンチルオキシ基、ヘキシルオキシ基等の炭素数１
〜６の直鎖又は分枝鎖のものが挙げられる。
なお、上述した(1)式に示す化学構造式を有する
本発明化合物を具体的に例示すると第１表に示す
通りである。
The present invention provides the following formula (1) having excellent antitumor effect: (However, R 1 is a phenyl group or one of its hydrogen atoms.
Or it represents a phenyl group in which two or more of them are substituted with a halogen atom, a lower alkyl group, a lower alkoxy group or a nitro group, and R 2 represents a hydrogen atom or a methyl group. ) A novel 5-phenylamino-1-phenyl-1H-pyrazolo[3,4-b]pyrazine derivative. Conventionally, various substances having antitumor effects have been developed and proposed, and the present inventors have also conducted intensive research on compounds that have excellent antitumor effects and can be suitably used as antitumor agents. Among them, a new compound 5-phenylamino-1- represented by the above formula (1) was created by a method such as reacting 5-chloro-1-phenyl-1H-pyrazolo[3,4-b]pyrazine with an aniline derivative. Phenyl-1H
-Pyrazolo[3,4-b]pyrazine derivatives were obtained, and it was discovered that these compounds have excellent antitumor effects and can be effectively used as antitumor agents, leading to the present invention. Ivy. The present invention will be explained in more detail below. Novel compound 5-phenylamino according to the present invention
The 1-phenyl-1H-pyrazolo[3,4-b]pyrazine derivative has the above-mentioned formula (1), i.e. (However, R 1 is a phenyl group or one of its hydrogen atoms.
or a phenyl group substituted with two or more halogen atoms such as fluorine, chlorine, bromine, and iodine, lower alkyl groups, lower alkoxy groups, or nitro groups, and R 2 represents a hydrogen atom or a methyl group. ) It has the chemical structural formula shown below. In formula (1), the lower alkyl group includes a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a pentyl group,
1 or more carbon atoms such as isopentyl group and neopentyl group
6 straight or branched chains. In addition, examples of lower alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentyloxy, and hexyloxy groups with a carbon number of 1.
~6 straight or branched chains. Specific examples of the compounds of the present invention having the chemical structural formula shown in formula (1) above are shown in Table 1.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】
前記(1)式の化合物は、５―ハロゲノ―１―フエ
ニル―1H―ピラゾロ〔３，４―ｂ〕ピラジン等
に対し、該当する置換もしくは未置換のフエニル
アミンを反応させることにより合成することがで
きる（下記反応式ａ参照）。
（但し、Ｘはハロゲン原子、−SO2R基、−NO2基
又は−CN基を示し（なお、Ｒは低級アルキル
基、フエニル基又はアルキルフエニル基を示す）、
R2は前記の意味を示す。）
なお、(2)式においてＸがクロル原子である５―
クロロ―１―フエニル―1H―ピラゾロ〔３，４
―ｂ〕ピラジン（式（2′））は、下記反応式ｂに
その一例を示すように、(3)式の５―アミノ―１―
フエニル―ピラゾール―４―カルボン酸を例えば
180℃に加熱して脱炭酸を行ない、(4)式の５―ア
ミノ―１―フエニル―ピラゾールを合成し、これ
を乾燥塩酸存在下エタノール中で亜硝酸アソアミ
ルと反応させて(5)式の５―アミノ―４―ニトロソ
―１―フエニル―ピラゾール塩酸塩を得た後、こ
れをパラジウム炭素を用いて接触還元することに
より(6)式の４，５―ジアミノ―１―フエニル―ピ
ラゾールを合成し、次いでこれを水中でグリオキ
シル酸と反応させて(7)式の４，５―ジヒドロ―１
―フエニル―1H―ピラゾロ〔３，４―ｂ〕ピラ
ジン―５―オンを合成し、最後にこれをオキシ塩
化リンと還流することにより得ることができる。
前記(1)式の化合物は、優れた抗腫瘍作用を有
し、癌化細胞の増殖を抑制するため、抗腫瘍剤と
して有効に使用される。
以下、本発明化合物(1)の製造例を具体的に示
す。
製造例 １〜11
５―クロロ―１―フエニル―1H―ピラゾロ
〔３，４―ｂ〕ピラジン1.36ｇ（６ミリモル）と
第１表に示すフエニルアミン25ミリモルとを封管
中220℃で３時間反応させた後、クロロホルムに
溶解する。これを2N塩酸30ml、次いで2N炭酸ナ
トリウム水溶液10ml、最後に水10mlで２回洗浄
し、無水硫酸ナトリウムで乾燥し、溶媒を減圧下
で留去する。残渣を第２表に示す再結晶溶媒で再
結晶し、第２表に示す通りの目的化合物を得た。
これら化合物の形状、収率を第２表に、融点、
IRを第３表に示す。[Table] The compound of formula (1) above is synthesized by reacting 5-halogeno-1-phenyl-1H-pyrazolo[3,4-b]pyrazine, etc. with the corresponding substituted or unsubstituted phenylamine. (See reaction formula a below). (However, X represents a halogen atom, -SO2R group, -NO2 group, or -CN group (R represents a lower alkyl group, phenyl group, or alkylphenyl group),
R 2 has the above meaning. ) In addition, in formula (2), 5-
Chloro-1-phenyl-1H-pyrazolo[3,4
-b] Pyrazine (formula (2')) is a 5-amino-1-
For example, phenyl-pyrazole-4-carboxylic acid
The 5-amino-1-phenyl-pyrazole of formula (4) was synthesized by heating to 180°C for decarboxylation, and this was reacted with asoamyl nitrite in ethanol in the presence of dry hydrochloric acid to obtain the formula (5). After obtaining 5-amino-4-nitroso-1-phenyl-pyrazole hydrochloride, it was catalytically reduced using palladium carbon to synthesize 4,5-diamino-1-phenyl-pyrazole of formula (6). Then, this was reacted with glyoxylic acid in water to obtain 4,5-dihydro-1 of formula (7).
-Phenyl-1H-pyrazolo[3,4-b]pyrazin-5-one can be synthesized and finally refluxed with phosphorus oxychloride. The compound of formula (1) has an excellent antitumor effect and suppresses the proliferation of cancerous cells, and is therefore effectively used as an antitumor agent. Hereinafter, a production example of the compound (1) of the present invention will be specifically shown. Production Examples 1 to 11 1.36 g (6 mmol) of 5-chloro-1-phenyl-1H-pyrazolo[3,4-b]pyrazine and 25 mmol of phenylamine shown in Table 1 were reacted at 220°C for 3 hours in a sealed tube. After that, dissolve it in chloroform. This is washed twice with 30 ml of 2N hydrochloric acid, then with 10 ml of a 2N aqueous sodium carbonate solution, and finally with 10 ml of water, dried over anhydrous sodium sulfate, and the solvent is distilled off under reduced pressure. The residue was recrystallized using the recrystallization solvent shown in Table 2 to obtain the target compounds shown in Table 2.
The shapes and yields of these compounds are shown in Table 2, melting points,
IR is shown in Table 3.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
Claims (1)
又は２以上をハロゲン原子、低級アルキル基、低
級アルコキシ基もしくはニトロ基により置換され
たフエニル基を示し、R2は水素原子又はメチル
基を示す。） で示される５―フエニルアミノ―１―フエニル―
1H―ピラゾロ〔３，４―ｂ〕ピラジン誘導体。[Claims] 1. The following formula (However, R 1 is a phenyl group or one of its hydrogen atoms.
Or it represents a phenyl group in which two or more of them are substituted with a halogen atom, a lower alkyl group, a lower alkoxy group or a nitro group, and R 2 represents a hydrogen atom or a methyl group. ) 5-phenylamino-1-phenyl-
1H-pyrazolo[3,4-b]pyrazine derivative.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6367582A JPH0240672B2 (en) | 1982-04-16 | 1982-04-16 | 55FUENIRUAMINOO11FUENIRUU1HHPIRAZORO * 3 * 44B * PIRAJINJUDOTAI |
| US06/428,016 US4460773A (en) | 1982-02-05 | 1982-09-29 | 1-Phenyl-1H-pyrazolo [3,4-b]pyrazine derivatives and process for preparing same |
| DE19823237243 DE3237243A1 (en) | 1982-02-05 | 1982-10-07 | 1-PHENYL-1H-PYRAZOLO (3,4-B) PYRAZINE DERIVATIVES AND METHOD FOR THE PRODUCTION THEREOF |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6367582A JPH0240672B2 (en) | 1982-04-16 | 1982-04-16 | 55FUENIRUAMINOO11FUENIRUU1HHPIRAZORO * 3 * 44B * PIRAJINJUDOTAI |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58180485A JPS58180485A (en) | 1983-10-21 |
| JPH0240672B2 true JPH0240672B2 (en) | 1990-09-12 |
Family
ID=13236164
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6367582A Expired - Lifetime JPH0240672B2 (en) | 1982-02-05 | 1982-04-16 | 55FUENIRUAMINOO11FUENIRUU1HHPIRAZORO * 3 * 44B * PIRAJINJUDOTAI |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0240672B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6317882A (en) * | 1986-07-09 | 1988-01-25 | Lion Corp | 5-substituted-1H-pyrazolo[3,4-b]pyrazine derivatives and antitumor agents containing the compounds |
-
1982
- 1982-04-16 JP JP6367582A patent/JPH0240672B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58180485A (en) | 1983-10-21 |
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