JPS629104B2 - - Google Patents
Info
- Publication number
- JPS629104B2 JPS629104B2 JP5506778A JP5506778A JPS629104B2 JP S629104 B2 JPS629104 B2 JP S629104B2 JP 5506778 A JP5506778 A JP 5506778A JP 5506778 A JP5506778 A JP 5506778A JP S629104 B2 JPS629104 B2 JP S629104B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- derivative represented
- formula
- halogenoacetanilide
- halogen atom
- 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
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
【発明の詳細な説明】
本発明は新規なハロゲノアセトアニリド誘導体
およびその製法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel halogenoacetanilide derivative and a method for producing the same.
さらに詳しくいえば、本発明は一般式〔〕
〔式中、Ｘ，ＹおよびＺは、ハロゲン原子を意
味し、Ｒはシクロプロピルメチル基をあらわ
す。〕
であらわされる新規なハロゲノアセトアニリド誘
導体およびその製法に関するものである。 More specifically, the present invention relates to the general formula [] [In the formula, X, Y and Z mean a halogen atom, and R represents a cyclopropylmethyl group. ] The present invention relates to a novel halogenoacetanilide derivative represented by and a method for producing the same.
前記一般式〔〕においてハロゲン原子として
は例えば、塩素、臭素、沃素、弗素などがあげら
れる。 In the general formula [], examples of the halogen atom include chlorine, bromine, iodine, and fluorine.
前記一般式〔〕であらわされるハロゲノアセ
トアニリド誘導体は文献未記載の新規化合物であ
つて、例えば抗菌作用を有し、医薬品として有用
なものである。 The halogenoacetanilide derivative represented by the above general formula [] is a new compound that has not been described in any literature, and has, for example, an antibacterial effect and is useful as a pharmaceutical.
本発明化合物〔〕は一般式〔〕
〔式中、Ｘ，ＹおよびＲは前記と同じ意味を有
する。〕
であらわされるアミノベンゾフエノン誘導体と一
般式〔〕
Ｚ−CH2COOH 〔〕
〔式中、Ｚは前記と同じ意味を有する。〕
であらわされる酢酸誘導体の反応性誘導体とを反
応させて得られる。反応は通常有機溶剤が使用さ
れ、例えばクロロホルム、ベンゼン、トルエン、
キシレン、クロルベンゼン、ジメチルホルムアミ
ド、ジメチルスルホキサイドなどの不活性溶剤も
しくはその混合物が用いられる。 The compound of the present invention [] has the general formula [] [In the formula, X, Y and R have the same meanings as above. ] An aminobenzophenone derivative represented by the general formula [] Z-CH 2 COOH [] [wherein Z has the same meaning as above. ] It is obtained by reacting an acetic acid derivative represented by the following with a reactive derivative. Organic solvents are usually used for the reaction, such as chloroform, benzene, toluene,
Inert solvents such as xylene, chlorobenzene, dimethylformamide, dimethyl sulfoxide or mixtures thereof are used.
一般式〔〕の反応性誘導体としては、例えば
酸無水物、酸ハロゲン化物などがあげられ、酸ハ
ロゲン化物としては酸クロリド、酸ブロミド、酸
ヨウジドなどがあげられる。反応温度は通常加熱
して行うが、室温または冷却によつて反応を調節
することもできる。 Examples of the reactive derivative of the general formula [] include acid anhydrides and acid halides, and examples of the acid halides include acid chloride, acid bromide, and acid iodide. The reaction temperature is usually carried out by heating, but the reaction can also be controlled at room temperature or by cooling.
本発明による一般式〔〕のハロゲノアセトア
ニリド誘導体は各種製剤形で、例えば錠剤、被覆
錠剤、顆粒剤、カプセル剤、坐剤、注射用剤等の
形態で種々の天然または合成担体、希釈剤、安定
剤、例えばブドウ糖、庶糖、乳糖、澱粉、滑石、
ステアリン酸マグネシウム、カゼイン、リン酸カ
ルシウム、メチルセルロース、エチルセルロー
ス、アラビアゴム、ポリアルキレングリコール、
トラガント、蒸留水と組合わせて経口、非経口的
または局所的方法により投与することができる。
人では１日約50mg〜５ｇで投与できる。 The halogenoacetanilide derivatives of the general formula [] according to the present invention can be prepared in various pharmaceutical forms, such as tablets, coated tablets, granules, capsules, suppositories, injections, etc., with various natural or synthetic carriers, diluents, stabilizers, etc. agents, such as glucose, sucrose, lactose, starch, talc,
Magnesium stearate, casein, calcium phosphate, methylcellulose, ethylcellulose, gum arabic, polyalkylene glycol,
Tragacanth can be administered by oral, parenteral or topical methods in combination with distilled water.
For humans, it can be administered at approximately 50 mg to 5 g per day.
次に実施例をあげて本発明を説明するが、これ
らはその一例であつて何らの限定を受けるもので
はない。 Next, the present invention will be explained with reference to examples, but these are merely examples and are not intended to be limiting in any way.
実施例 １
２−（シクロプロピルメチル）アミノ−５−ク
ロル−Ｏ−フルオルベンゾフエノン１ｇをクロロ
ホルム12mlに溶解し、ブロムアセチルブロミド
1.04ｇを加え2.5時間撹拌還流した。冷後氷水を
注加し、クロロホルム部を分液した。クロロホル
ム部を水洗し、無水芒硝で乾燥後クロロホルムを
留去した。ｎ−ヘキサンより結晶化して淡黄色結
晶として、Ｎ−（シクロプロピルメチル）−２−
（Ｏ−フルオルベンゾイル）−４−クロル−ブロム
アセトアニリドを得た。本品は融点74〜76.5℃で
あり、流動パラフイン中の赤外吸収スペクトルに
おいて1670cm-1にアミドおよび芳香族ケトンのカ
ルボニル基による強い吸収を示した。Example 1 1 g of 2-(cyclopropylmethyl)amino-5-chloro-O-fluorobenzophenone was dissolved in 12 ml of chloroform, and bromoacetyl bromide was dissolved.
1.04 g was added and the mixture was stirred and refluxed for 2.5 hours. After cooling, ice water was added to separate the chloroform portion. The chloroform portion was washed with water, dried over anhydrous sodium sulfate, and then the chloroform was distilled off. Crystallized from n-hexane as pale yellow crystals, N-(cyclopropylmethyl)-2-
(O-fluorobenzoyl)-4-chloro-bromoacetanilide was obtained. This product had a melting point of 74-76.5°C, and showed strong absorption at 1670 cm -1 due to the carbonyl group of the amide and aromatic ketone in the infrared absorption spectrum in liquid paraffin.
Claims (1)
味し、Ｒはシクロプロピルメチル基をあらわ
す。〕 であらわされるハロゲノアセトアニリド誘導体。 ２ 一般式 〔式中、ＸおよびＹは、ハロゲン原子を意味
し、Ｒはシクロプロピルメチル基をあらわす。〕 であらわされるアミノベンゾフエノン誘導体と一
般式 Ｚ−CH2COOH 〔式中、Ｚはハロゲン原子を意味する。〕 であらわされる酢酸誘導体の反応性誘導体とを反
応させることを特徴とする一般式 〔式中、Ｘ，Ｙ，ＺおよびＲは前記と同じ意味
を有する。〕 であらわされる新規なハロゲノアセトアニリド誘
導体の製法。[Claims] 1. General formula [In the formula, X, Y and Z mean a halogen atom, and R represents a cyclopropylmethyl group. ] A halogenoacetanilide derivative represented by 2 General formula [In the formula, X and Y mean a halogen atom, and R represents a cyclopropylmethyl group. ] An aminobenzophenone derivative represented by the general formula Z-CH 2 COOH [wherein Z means a halogen atom. ] A general formula characterized by reacting an acetic acid derivative with a reactive derivative represented by [In the formula, X, Y, Z and R have the same meanings as above. ] A method for producing a novel halogenoacetanilide derivative represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5506778A JPS54148750A (en) | 1978-05-09 | 1978-05-09 | Novel halogenoacetanilide derivative and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5506778A JPS54148750A (en) | 1978-05-09 | 1978-05-09 | Novel halogenoacetanilide derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54148750A JPS54148750A (en) | 1979-11-21 |
| JPS629104B2 true JPS629104B2 (en) | 1987-02-26 |
Family
ID=12988339
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5506778A Granted JPS54148750A (en) | 1978-05-09 | 1978-05-09 | Novel halogenoacetanilide derivative and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS54148750A (en) |
-
1978
- 1978-05-09 JP JP5506778A patent/JPS54148750A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54148750A (en) | 1979-11-21 |
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