JPS603079B2 - Method for producing imidazo[4,5-b]pyridine derivatives - Google Patents
Method for producing imidazo[4,5-b]pyridine derivativesInfo
- Publication number
- JPS603079B2 JPS603079B2 JP9360575A JP9360575A JPS603079B2 JP S603079 B2 JPS603079 B2 JP S603079B2 JP 9360575 A JP9360575 A JP 9360575A JP 9360575 A JP9360575 A JP 9360575A JP S603079 B2 JPS603079 B2 JP S603079B2
- Authority
- JP
- Japan
- Prior art keywords
- imidazo
- pyridine
- pyridine derivatives
- producing
- acid
- 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
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
【発明の詳細な説明】
本発明は、制癌作用を示し医薬として有効な新規ィミダ
ゾ〔４，５一ｂ〕ピリジン誘導体の製造方法に関するも
のである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing a novel imidazo[4,51b]pyridine derivative that exhibits anticancer activity and is effective as a pharmaceutical.
従来、制癌作用を有する化合物を製造することが試みら
れてきているが、得られた化合物に制競効果が期待し得
るものでなかったり、麓性が強くて医薬としては利用し
難いものが多い。In the past, attempts have been made to produce compounds with anticancer effects, but some of the resulting compounds are not expected to have an anticancer effect, or have strong anticancer properties that make them difficult to use as medicines. many.
また、湊性も低く、制競作用を有する化合物であっても
、その製造法が複雑であったり、製造された化合物が不
安定であったり、十分に精製し難いものであったりする
欠点を有しており、医薬として実用化するまでには解決
すべき問題点が多かつた。In addition, even if the compound has a low concentration property and has a competitive action, the manufacturing method is complicated, the manufactured compound is unstable, or it is difficult to purify sufficiently. However, there were many problems that needed to be solved before it could be put into practical use as a medicine.
従来、イミダゾ〔４，５一ｂ〕ピリジン誘導体としては
、いくつかの化合物が知られ、またその製造法について
も提案されている。Conventionally, several compounds have been known as imidazo[4,51b]pyridine derivatives, and methods for producing the same have also been proposed.
たとえば、２，３−ジアノー５ークロロピリジンとイソ
酪酸を反応せしめ、６ークロロー２−イソプロピルィミ
ダゾ〔４，５−ｂ〕ピリジンの製造方法は特公昭４５−
斑２７９により公知である。しかし、本発明によるイミ
ダゾ〔４，５−ｂ〕ピリジン誘導体は優れた制癌作用を
有する化合物で、従来は全く知られていなかった新規な
化合物である。For example, a method for producing 6-chloro-2-isopropylimidazo[4,5-b]pyridine by reacting 2,3-diano-5-chloropyridine with isobutyric acid was published in
It is known by the spot 279. However, the imidazo[4,5-b]pyridine derivative according to the present invention is a novel compound that has excellent anticancer activity and has not been previously known at all.
本発明は、副作用がより少なく、優れた薬理作用と安定
性を示す制癌剤を簡単な操作によって収薬良好でコスト
安価に得ることができる、新規なィミダゾ〔４，５−ｂ
〕ピリジン譲導体の製造方法を提供することを目的とす
るものである。The present invention provides a novel imidazo [4,5-b
] The object of the present invention is to provide a method for producing a pyridine derivative.
本発明により製造される新規ィミダゾ〔４．５一ｂ〕ピ
リジン誘導体は式
で示される化合物である。The novel imidazo[4.51b]pyridine derivatives prepared according to the present invention are compounds represented by the formula.
このィミダゾ〔４，５一ｂ〕ピリジン穣導体は、式
で示される２ーメチル−ＩＨ−イミダゾ〔４，５一ｂ〕
ピリジン誘導体を、式
で示されるアルデヒド類と反応させることから成る方法
で製造される。This imidazo[4,51b]pyridine conductor is a 2-methyl-IH-imidazo[4,51b] represented by the formula
It is prepared by a process consisting of reacting pyridine derivatives with aldehydes of the formula.
この反応は一般に２００ｑｏ〜３０ぴ○間の温度で行な
うことができる。This reaction can generally be carried out at a temperature of between 200 qo and 30 pi.
さらに、この反応は触媒を用いなくても行なわしめるこ
とができるが、酸などの滋媒を使用すれば反応を速める
ことができる。触媒として使用する場合の酸としては、
酢酸、ブロピオン酸等の有機酸、塩酸、硫酸等の無機酸
を用いる。前記した２−メチル−ＩＨ−ィミダゾ〔４，
５一ｂ〕ピリジン誘導体は、２，３−ジアセトアミドピ
リジン誘導体を２０び０〜３００℃に加熱して製造する
ことができ、また、２，３ージアミノピリジン誘導体に
酢酸を加え加熱環流することによっても製造されるもの
である。Furthermore, although this reaction can be carried out without the use of a catalyst, the reaction can be accelerated by using a nutrient medium such as an acid. As an acid when used as a catalyst,
Organic acids such as acetic acid and propionic acid, and inorganic acids such as hydrochloric acid and sulfuric acid are used. 2-Methyl-IH-imidazo [4,
51b] Pyridine derivatives can be produced by heating 2,3-diacetamidopyridine derivatives to 20 and 0 to 300°C, or by adding acetic acid to 2,3-diaminopyridine derivatives and heating and refluxing them. It is also manufactured by.
次に本発明を実施例により説明する。Next, the present invention will be explained by examples.
実施例
６−ブロモー２一（４−メトキシスチリル）一ＩＨ−ィ
ミダゾ〔４，５一ｂ〕ピリジンの製造方法。Example 6 - Method for producing bromo2-(4-methoxystyryl)-IH-imidazo[4,51b]pyridine.
６ーブロモ−２ーメチル−ＩＨーイミダゾ〔４，５一ｂ
〕ピリジン６５夕にＰ−メトキシベンズアルデヒド９．
８夕と酢酸１．８５夕を加え、２３ぴ○で９ひげ間反応
させた後、放冷し、次いでエーテルを加え析出した結晶
を炉別する。6-Bromo-2-methyl-IH-imidazo[4,51b
] Pyridine 65 and P-methoxybenzaldehyde 9.
After adding 8 liters of acetic acid and 1.85 liters of acetic acid and reacting for 9 hours at 23 psi, the mixture was allowed to cool, then ether was added and the precipitated crystals were separated by furnace.
得られた結晶をピリジンから再結晶し目的物６８夕を得
た。性状は次の遜りである。The obtained crystals were recrystallized from pyridine to obtain the desired product 68. The properties are as follows.
融点：３瓜ぴ０〜３０１℃
元素分析（％）：
○ Ｈ Ｎ
分析値 ５４．１２ ３．８０ １２．４１計算
値 ５４．５４ ３．６６ １２．７３本発明
により製造された化合物の動物試験。Melting point: 0 to 301°C Elemental analysis (%): ○ H N Analysis value 54.12 3.80 12.41 Calculated value 54.54 3.66 12.73 Animal testing of compounds produced according to the present invention .
試験方法：２５タマゥス（ｄｄＹ）に対してエールリツ
ヒ腫物細胞（３×１び）を皮下に与え１４日間観察する
。Test method: Ehrlichi tumor cells (3 x 1 cell) were given subcutaneously to 25 tamus (ddY) and observed for 14 days.
マウス１０匹を１グループとし、２グループに分けて、
それぞれ対照グループ、試験グループとする。試験グル
ープにはエールリッヒ腫湯細胞を接種後２蝿時間経過し
た後、毎日、マウスの体重ｌｋ９当り４０倣（４０柵／
ｋ９）の６−フロモー２−（４ーメトキシスチリル）一
ＩＨ−イミダド〔４，５−ｂ〕ピリジンを腹腔より投与
し、７日間経て、薬剤投与をやめ、以後１４日まで観察
を続ける。One group consists of 10 mice, and they are divided into two groups.
A control group and a test group, respectively. Two hours after inoculation with Ehrlich tumor cells, the test group was given 40 imitations per lk9 of the mouse's body weight (40 mice/kg) every day.
K9) 6-furomo2-(4-methoxystyryl)-IH-imidado[4,5-b]pyridine was administered intraperitoneally, and drug administration was stopped after 7 days, and observation was continued until day 14.
１４日間にマウスより腫湯をとり出し、その重量を測定
する。After 14 days, boils are removed from the mice and their weights are measured.
結果：
マウスよりとり出した平均腫湯重量は次の通りであった
。Results: The average weight of tumor fluid taken out from mice was as follows.
対照グループ：１．８０タ
試験グルーム：０．鬼夕
すなわち、試験グループの平均腫湯量量は対照グループ
の平均腫湯重量の３０％に減少し、７０％の制擬効果が
認められる。Control group: 1.80 ta Test groom: 0. In other words, the average volume of tumor in the test group was reduced to 30% of the average volume of tumor in the control group, indicating a 70% suppression effect.
また、試験グループの１０匹のマウスには１４日間の観
察期間中に死亡例は一例もなく、他の異常も認められな
かった。Furthermore, none of the 10 mice in the test group died during the 14-day observation period, and no other abnormalities were observed.
Claims (1)
〕ピリジン誘導体と、式 ▲数式、化学式、表等があります▼ で示されるアルテヒド類とを反応せしめることを特徴と
する、 式 ▲数式、化学式、表等があります▼ で表わされるイミダゾ（４，５−ｂ〕ピリジン誘導体の
製造方法。[Scope of Claims] 1 2-Methyl-1H-imidazo[4,5,-b
] Imidazo (4,5 -b] Method for producing a pyridine derivative.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9360575A JPS603079B2 (en) | 1975-07-31 | 1975-07-31 | Method for producing imidazo[4,5-b]pyridine derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9360575A JPS603079B2 (en) | 1975-07-31 | 1975-07-31 | Method for producing imidazo[4,5-b]pyridine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5217494A JPS5217494A (en) | 1977-02-09 |
| JPS603079B2 true JPS603079B2 (en) | 1985-01-25 |
Family
ID=14086949
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9360575A Expired JPS603079B2 (en) | 1975-07-31 | 1975-07-31 | Method for producing imidazo[4,5-b]pyridine derivatives |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS603079B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5319995B2 (en) * | 1972-09-14 | 1978-06-23 |
-
1975
- 1975-07-31 JP JP9360575A patent/JPS603079B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5217494A (en) | 1977-02-09 |
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