JPS60149585A - Pyrazolopyridine derivative - Google Patents
Pyrazolopyridine derivativeInfo
- Publication number
- JPS60149585A JPS60149585A JP21925784A JP21925784A JPS60149585A JP S60149585 A JPS60149585 A JP S60149585A JP 21925784 A JP21925784 A JP 21925784A JP 21925784 A JP21925784 A JP 21925784A JP S60149585 A JPS60149585 A JP S60149585A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- lower alkyl
- room temperature
- general formula
- 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.)
- Granted
Links
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
【発明の詳細な説明】 生業」Ｊ冴り１分貫一 本発明は新規なピラゾロピリジン誘導体に関する。[Detailed description of the invention] “Nursing” J Saekari 1 minute Kanichi The present invention relates to novel pyrazolopyridine derivatives.
従迷！Ｉ幻例
本発明のピラゾロピリジン誘導体は文献等に未載の新規
化合物である。Obedience! I. Phantom Example The pyrazolopyridine derivative of the present invention is a new compound that has not been described in any literature.
■が”しようとする問題点
本発明は後記するように医薬品として有用な化合物を提
供することを目的とする。(2) Problems to be Addressed As will be described later, the purpose of the present invention is to provide a compound useful as a pharmaceutical.
問題を解決するための平置
上記目的は下記一般式（１）で表されるピラゾロピリジ
ン誘導体により達成される。The above object is achieved by a pyrazolopyridine derivative represented by the following general formula (1).
（式中、Ｒは低級アルキル基、又は低級アルコキシカル
ボニルメチル基を、Ｒ１，Ｒ２及びＲ３は水素原子、又
は低級アルキル基を、Ｒ４は低級アルコキシ基を意味す
る。）
本発明の上記化合物は文献未載の新規化合物であって降
圧作用、抗アレルギー作用、消炎作用を有し医薬品とし
て有用である。(In the formula, R means a lower alkyl group or a lower alkoxycarbonylmethyl group, R1, R2 and R3 mean a hydrogen atom or a lower alkyl group, and R4 means a lower alkoxy group.) This is a new, unpublished compound that has antihypertensive, antiallergic, and antiinflammatory effects and is useful as a pharmaceutical.
本発明のピラゾロピリジン誘導体（１）は、一般式（２
）で示される化合物と、一般式（３）で示される化合物
とを反応させて、一般式（４）で示される化合物となし
、次いで塩基の存在下に閉環縮合させることによって製
造することができる。The pyrazolopyridine derivative (1) of the present invention has the general formula (2
) and a compound represented by general formula (3) to form a compound represented by general formula (4), and then ring-closing condensation in the presence of a base. .
１
（２）
（４）
Ｒ】
（１）
（式中、Ｒ，Ｒ１，Ｒ２，Ｒ３及びＲ４ば前記に同じで
あり、Ｘはハロゲン原子を意味する。）一般式（２）で
示される化合物と、一般式（３）で示される化合物との
反応は一般に不活性溶媒中で行われる。不活性溶媒とし
ては、例えばクロロホルム、ジクロルメタン、メタノー
ル、エタノール、ベンゼン、テトラヒドロフラン、ジメ
チルスルホキシド、Ｎ、Ｎ−ジメチルポルムアミド等が
用いられる。反応温度は通常、室温から５０°Ｃの間を
選択するのが好ましい。上記反応により、一般式（４）
で示される化合物が生成し、これは通常の分離手段によ
り単離可能である。1 (2) (4) R] (1) (In the formula, R, R1, R2, R3 and R4 are the same as above, and X means a halogen atom) Compound represented by general formula (2) The reaction between the compound and the compound represented by the general formula (3) is generally carried out in an inert solvent. Examples of inert solvents that can be used include chloroform, dichloromethane, methanol, ethanol, benzene, tetrahydrofuran, dimethyl sulfoxide, and N,N-dimethylpolamide. The reaction temperature is usually preferably selected between room temperature and 50°C. By the above reaction, general formula (4)
A compound of the formula is produced, which can be isolated by conventional separation means.
次ぎに一般式（４）で示される化合物を上記の不活性溶
媒中、塩基の存在下、室ｉ２Ａがら５ｏ″Ｃで閉環縮合
させることにより、本発明のピラゾロピリジン誘導体（
１）が生成する。塩基としては例えば炭酸カリウム、炭
酸ナトリウム、水酸化ナトリウム、水酸化カリウム、ナ
トリウムアミド。Next, the compound represented by the general formula (4) is subjected to ring-closing condensation at 5o''C from chamber i2A in the above-mentioned inert solvent in the presence of a base to obtain the pyrazolopyridine derivative of the present invention (
1) is generated. Examples of the base include potassium carbonate, sodium carbonate, sodium hydroxide, potassium hydroxide, and sodium amide.
カリウムアミド、水素化ナトリウム等の無機塩基、１，
５−ジアザビシクロ［５，１０１ウンデセン−５（ＤＢ
Ｕ） 、１．５−ジアザビシクロ［４，３−０］ノネン
−５（ＤＢＮ）等の有機塩基が用いられる。Inorganic bases such as potassium amide and sodium hydride, 1,
5-diazabicyclo[5,101 undecene-5 (DB
U), an organic base such as 1,5-diazabicyclo[4,3-0]nonene-5 (DBN) is used.
実施例
本反応によって得られる一般式（１）で示される代表的
化合物を表１に示す。Examples Table 1 shows representative compounds represented by the general formula (1) obtained by this reaction.
次に本発明の実施例を挙げて、更に具体的に説明する。Next, the present invention will be described in more detail with reference to Examples.
実施例 １
３−エトキシカルボニル−２−メチルチオピラゾロ［１
，５−ａ］ ピリジンの合成
１−（（メチルチオ）チオカルボニルイミノ）ピリジニ
ウムイリド ３６８ｍｇ （２ミリモル）を、クロロホ
ルム１０ｍ１に溶解し、エチルブロモアセテート ４０
０ｍｇ （２，４ミリモル）を加えて室温で一晩放置す
る。溶媒を留去して得たピリジニウム塩をエーテル（２
０ｍｌ）で洗浄する。この塩をクロロホルム５０ｍ１に
溶解し、無水炭酸カリウム ５ｇを加えて室温で一晩攪
拌する。無機物を濾去し、濾液を濃縮する。Example 1 3-ethoxycarbonyl-2-methylthiopyrazolo[1
, 5-a] Synthesis of pyridine 1-((Methylthio)thiocarbonylimino)pyridinium ylide 368 mg (2 mmol) was dissolved in chloroform 10 ml, and ethyl bromoacetate 40
Add 0 mg (2.4 mmol) and leave at room temperature overnight. The pyridinium salt obtained by distilling off the solvent was dissolved in ether (2
0ml). Dissolve this salt in 50 ml of chloroform, add 5 g of anhydrous potassium carbonate, and stir overnight at room temperature. Filter off the inorganics and concentrate the filtrate.
残渣をアルミナカラムを用いて精製した後、エタノール
から再結晶すると、３−エトキシカルボニル−２−メチ
ルチオピラゾ”［Ｒ５−ａ］ ピリジン（化合物番号１
）が得られた。After the residue was purified using an alumina column and recrystallized from ethanol, 3-ethoxycarbonyl-2-methylthiopyrazo"[R5-a]pyridine (compound number 1
)was gotten.
実施例 ２
実施例 １ と同様に操作して、表１中の化合物番号
２−９の化合物を合成した。Example 2 In the same manner as in Example 1, compound numbers in Table 1 were added.
Compound 2-9 was synthesized.
Claims (1)
ボニルメチル基を、Ｒ１，Ｒ２及びＲ３は水素原子、又
は低級アルキル基を、Ｒ４は低級アルコキシ基を意味す
る。）で示されるピラゾロピリジン誘導体。(1) General formula (wherein, R represents a lower alkyl group or a lower alkoxycarbonylmethyl group, R1, R2, and R3 represent a hydrogen atom or a lower alkyl group, and R4 represents a lower alkoxy group). Pyrazolopyridine derivative.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21925784A JPS60149585A (en) | 1984-10-17 | 1984-10-17 | Pyrazolopyridine derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21925784A JPS60149585A (en) | 1984-10-17 | 1984-10-17 | Pyrazolopyridine derivative |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58152052 Division |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60149585A true JPS60149585A (en) | 1985-08-07 |
| JPH0372225B2 JPH0372225B2 (en) | 1991-11-18 |
Family
ID=16732682
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21925784A Granted JPS60149585A (en) | 1984-10-17 | 1984-10-17 | Pyrazolopyridine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60149585A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9482475B2 (en) | 2009-11-27 | 2016-11-01 | Kabushiki Kaisha Toshiba | Heat exchanger |
-
1984
- 1984-10-17 JP JP21925784A patent/JPS60149585A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9482475B2 (en) | 2009-11-27 | 2016-11-01 | Kabushiki Kaisha Toshiba | Heat exchanger |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0372225B2 (en) | 1991-11-18 |
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