JPS6051195A - 6-amino-7,8-thiazolopurine and its preparation - Google Patents
6-amino-7,8-thiazolopurine and its preparationInfo
- Publication number
- JPS6051195A JPS6051195A JP58158542A JP15854283A JPS6051195A JP S6051195 A JPS6051195 A JP S6051195A JP 58158542 A JP58158542 A JP 58158542A JP 15854283 A JP15854283 A JP 15854283A JP S6051195 A JPS6051195 A JP S6051195A
- Authority
- JP
- Japan
- Prior art keywords
- amino
- formula
- compound
- solvent
- thiazolopurine
- 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
Links
Landscapes
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、新規化合物である６−アミノ−７，８−チア
ソロプリンおよびその製造法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel compound, 6-amino-7,8-thiasolopurine, and a method for producing the same.
プリンは、ピリミジン６員環とイミダゾール５員環とが
４，５位の炭素原子を共有する網金環状化合物である。Purine is a mesh cyclic compound in which a 6-membered pyrimidine ring and a 5-membered imidazole ring share carbon atoms at the 4 and 5 positions.
本発明は更にその７，８位てチアゾリジン環を形成せし
めたものである。本発明化合物は式［■１：
で示される。このものは、例えば抗アレルキ′−剤とし
て有用である。In the present invention, a thiazolidine ring is further formed at the 7 and 8 positions. The compound of the present invention is represented by the formula [■1:]. This product is useful, for example, as an anti-allergy agent.
本発明によれば、式１ｌ：
！−−Ａ
で示される１、２−チアゾロ−４−アミノ−５−シアノ
イミタソールをホルムアミド（ＨＣＯＮＨ２）の存在下
に加温することにより、目的化合物開力（得られる。According to the invention, formula 1l: ! By heating 1,2-thiazolo-4-amino-5-cyanoimitasole represented by --A in the presence of formamide (HCONH2), the target compound (obtained).
反応は、ホルムアミド自身を溶媒とすることが望ましく
、温度１５０〜２００°Ｃの加温下に、５〜１０時間を
要して反応の完結をみる。The reaction preferably uses formamide itself as a solvent, and takes 5 to 10 hours to complete while heating at a temperature of 150 to 200°C.
生成するプリン誘導体１．１１は、難溶性であるので、
反応液を冷却して放置すれば結晶として容易に得られる
。Since the generated purine derivative 1.11 is poorly soluble,
If the reaction solution is cooled and allowed to stand, crystals can be easily obtained.
原料のイミダゾール化合物１月は、式叫で示されるＮ−
シアノイミノチアゾリジン
−ＣＮ
とクロルアセトニトリル（ＣＪ？ＣＨ２ＣＮ ） とを
、溶媒（例えは、ジメチルホルムアミド、ジメチルスル
ホキシド）中、塩基（例えばアルカリ金属水素化物、ア
ルカリ金属アルコキサイド）の存在下に反応させて、式
ｆｆｌ’Ｉ
−ＣＮ
で示される２−（Ｎ−シアノイミノ）−３−シアノメチ
ルチアゾリジンを得、これを溶媒（ジメチルホルムアミ
ド、ジメチルスルホキシド、低級アルコールなど）中、
触媒量の塩基（アルカリ金属水素化物、アルカリ金属ア
ルコキサイドなど）の存在下で閉環せしめることにより
得られる。 。The raw material imidazole compound is N-
Cyanoiminothiazolidine-CN and chloroacetonitrile (CJ?CH2CN) are reacted in a solvent (e.g. dimethylformamide, dimethyl sulfoxide) in the presence of a base (e.g. alkali metal hydride, alkali metal alkoxide) to form the formula 2-(N-cyanoimino)-3-cyanomethylthiazolidine represented by ffl'I -CN was obtained, and this was dissolved in a solvent (dimethylformamide, dimethylsulfoxide, lower alcohol, etc.).
It is obtained by ring closure in the presence of a catalytic amount of a base (alkali metal hydride, alkali metal alkoxide, etc.). .
実施例
ホルムアミド２０献に１，２−チアソロ−４−アミノ−
５−シアノイミダソール１．６６ｆ（１０ミリモル）を
加え、１６０°Ｃで５時間撹拌する。1,2-Thiasoro-4-amino- in Example Formamide 20
Add 1.66 f (10 mmol) of 5-cyanoimidazole and stir at 160°C for 5 hours.
室温に冷却してそのまま一夜放置する。生成した結晶を
Ｐ取し、メタノールで洗浄して６−アミノ−７，８−チ
アゾロプリンを得る。収量１．．２１ｙ（６２，７％）
。融点３００°Ｃ以上。Cool to room temperature and leave overnight. The generated crystals are collected and washed with methanol to obtain 6-amino-7,8-thiazolopurine. Yield 1. ．． 21y (62.7%)
. Melting point over 300°C.
元素分析値（Ｃ７Ｈ７Ｎ５Ｓ＝ １９８．２３１として
）計算値（％）：Ｃ４３５１、Ｈ３，６５、Ｎ３６．２
４、実測値（％）：Ｃ４３，４６、Ｈ３，６２、Ｎ３５
．９９゜参考例
１．２−チアソロ−４−アミノ−５−シアノイミダゾー
ルの製造：
［月 ジメチルホルムアミド
５０％ＮａＨ１．５０ｇ（３１．５ミリモル）を懸澗さ
せ、０〜５°Ｃに冷却し、Ｎ−シアノイミノチアゾリジ
ン４．０ ｙ（ ３ １．５ミリモル）を徐々に加える
。Elemental analysis value (as C7H7N5S = 198.231) Calculated value (%): C4351, H3,65, N36.2
4. Actual value (%): C43,46, H3,62, N35
．． 99° Reference Example 1. Production of 2-thiasolo-4-amino-5-cyanoimidazole: Suspend 1.50 g (31.5 mmol) of 50% NaH in dimethylformamide, cool to 0-5°C, 4.0 y (1.5 mmol) of N-cyanoiminothiazolidine are added slowly.
水素の発生が止んだら、クロロアセトニトリル２、８８
ｆ（３１．５ミリモル）を滴下する。ＤＭＦを減圧留去
し、残渣を２Ｎ水酸化ナトリウムと酢酸エチルで抽出し
、酢酸エチル相を乾燥後留去する。残渣をエーテルでデ
カンテーションしたのち、水を加えて粗結晶を得、酢酸
エチルから再結晶して２−（Ｎ−シアノイミノ）−３−
シアノメチルチアゾリジンを得る。１．１ｆ（２１．０
％）。融点１４５〜１４６°Ｃ。When hydrogen generation stops, add chloroacetonitrile 2,88
f (31.5 mmol) is added dropwise. DMF was distilled off under reduced pressure, the residue was extracted with 2N sodium hydroxide and ethyl acetate, and the ethyl acetate phase was dried and then distilled off. After decanting the residue with ether, water was added to obtain crude crystals, which were recrystallized from ethyl acetate to give 2-(N-cyanoimino)-3-
Cyanomethylthiazolidine is obtained. 1.1f (21.0
%). Melting point 145-146°C.
■］ 上記で得た２−（Ｎ−シアノイミノ）−３−シア
ノメチルチアゾリジン１．６６ｙ（ＩＯミリモル）をエ
タノール５０Ｍｔに溶かし、ついで金属ナトリウムを少
量溶解する。３０分間還流し、反応終了後冷却する。生
成した結晶を炉取し、エーテルで洗浄して１，２−チア
ゾロ−４−アミノ−５−シアノイミダゾールを得る。収
量１５１ｇ（９０．１％）。融点２１８〜２１９°Ｃ（
分解）。[2] 1.66y (IO mmol) of 2-(N-cyanoimino)-3-cyanomethylthiazolidine obtained above is dissolved in 50Mt of ethanol, and then a small amount of metallic sodium is dissolved. The mixture was refluxed for 30 minutes and cooled after the reaction was completed. The produced crystals are collected and washed with ether to obtain 1,2-thiazolo-4-amino-5-cyanoimidazole. Yield 151g (90.1%). Melting point 218-219°C (
Disassembly).
元素分析値（ Ｃ６Ｈ６Ｎ４Ｓ ＝ １ ６ ６． ２
０ ６として）計算値（％）：Ｃ４３．３６、Ｈ３．
６４、Ｎ’１３．７１、実測値（％）：Ｃ４２．２９、
Ｈ８．５８、Ｎ３２６９。Elemental analysis value (C6H6N4S = 1 6 6. 2
0 6) Calculated value (%): C43.36, H3.
64, N'13.71, actual value (%): C42.29,
H8.58, N3269.
Claims (2)
タソールをホルムアミドの存在下に加温することを特徴
とする６−アミノ−７，８−チアゾロプリンの製造法。(2) A method for producing 6-amino-7,8-thiazolopurine, which comprises heating 1.2-thiazolo-4-amino-5-soanoimitasole in the presence of formamide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58158542A JPS6051195A (en) | 1983-08-30 | 1983-08-30 | 6-amino-7,8-thiazolopurine and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58158542A JPS6051195A (en) | 1983-08-30 | 1983-08-30 | 6-amino-7,8-thiazolopurine and its preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6051195A true JPS6051195A (en) | 1985-03-22 |
Family
ID=15673978
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58158542A Pending JPS6051195A (en) | 1983-08-30 | 1983-08-30 | 6-amino-7,8-thiazolopurine and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6051195A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63307857A (en) * | 1987-06-09 | 1988-12-15 | Nippon Tokushu Noyaku Seizo Kk | Cyanoalkyl-heterocyclic compound and insecticide |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS516992A (en) * | 1974-07-03 | 1976-01-20 | Dainippon Pharmaceutical Co | JIHIDOROCHIAZOROADENIN JUDOTAINO SEIHO |
-
1983
- 1983-08-30 JP JP58158542A patent/JPS6051195A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS516992A (en) * | 1974-07-03 | 1976-01-20 | Dainippon Pharmaceutical Co | JIHIDOROCHIAZOROADENIN JUDOTAINO SEIHO |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63307857A (en) * | 1987-06-09 | 1988-12-15 | Nippon Tokushu Noyaku Seizo Kk | Cyanoalkyl-heterocyclic compound and insecticide |
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