JPS6026786B2 - Novel phthalazone derivatives - Google Patents
Novel phthalazone derivativesInfo
- Publication number
- JPS6026786B2 JPS6026786B2 JP5334276A JP5334276A JPS6026786B2 JP S6026786 B2 JPS6026786 B2 JP S6026786B2 JP 5334276 A JP5334276 A JP 5334276A JP 5334276 A JP5334276 A JP 5334276A JP S6026786 B2 JPS6026786 B2 JP S6026786B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- phthalazone
- novel
- compound
- dimethyl
- 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
Description
【発明の詳細な説明】
本発明は、一般式
（式中Ｒ，及びＲ２は低級アルキル基、Ｒ３は直鎖状も
しくは分岐状のアルキル基、Ｘはハロゲン原子を意味す
る）で表わされる新規なフタラゾン誘導体に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention provides a novel compound represented by the general formula (wherein R and R2 are lower alkyl groups, R3 is a linear or branched alkyl group, and X is a halogen atom). Relating to phthalazone derivatives.
式１の化合物は、一般式
（式中Ｒ，，Ｒ２及びＲ３は前記の意味を有する）で表
わされる化合物（ロ）にハロゲン化剤を作用させること
により製造される。The compound of formula 1 is produced by reacting a halogenating agent with a compound (b) represented by the general formula (in which R, , R2 and R3 have the above-mentioned meanings).
式ロの化合物は、特関昭５０−７０３８０号及び特関昭
４８一１２１２６０号明細書（特開昭５０−７０３７８
号公報）に記載の方法により製造できる。その例として
は７−ェトキシカルボニルー６，８ージメチルー４ーヒ
ドロキシメチル−１ーフタラゾン、７ープロポキシカル
ボニルー６，８−ジメチルー４ーヒドロキシメチル−１
ーフタラゾンなどがあげられる。式１の化合物を製造す
るに際しては、アルコール性水酸基をハロゲン化する際
用いられる一般の方法が用いられ、たとえば塩化チオニ
ルを式０の化合物に添加して５０〜１００００で加熱す
る。The compound of formula (B) is described in Tokokukan Sho 50-70380 and Tokoku Sho 48-121260 (Japanese Patent Laid-Open No. 50-70378).
It can be produced by the method described in the following publication. Examples include 7-ethoxycarbonyl-6,8-dimethyl-4-hydroxymethyl-1-phthalazone, 7-propoxycarbonyl-6,8-dimethyl-4-hydroxymethyl-1
- Examples include phtalazone. In producing the compound of formula 1, a general method used for halogenating an alcoholic hydroxyl group is used, for example, thionyl chloride is added to the compound of formula 0 and heated at 50 to 10,000.
反応生成物は常法により容易に単離精製できる。式１の
化合物は、新規化合物であって、循環系疾患に有用な化
合物、たとえば７ーェトキシカルボニル一６，８ージメ
チルー４ーアミノメチルー１ーフタラゾンなどを合成す
るための中間体として有用である。The reaction product can be easily isolated and purified by conventional methods. The compound of formula 1 is a novel compound and is useful as an intermediate for the synthesis of compounds useful for circulatory system diseases, such as 7-ethoxycarbonyl-6,8-dimethyl-4-aminomethyl-1-phthalazone.
実施例
７ーエトキシカルボニル一６，８ージメチルー４ークロ
ロメチルー１ーフタラゾン。Example 7 - Ethoxycarbonyl-6,8-dimethyl-4-chloromethyl-1-phthalazone.
この化合物は下記の方法により製造される。This compound is produced by the following method.
７ーエトキシカルボニル−６，８−ジメチル−４ーヒド
ロキシメチルー１ーフタラゾン３のこ塩化チオニル１０
の‘を滴下し、反応混合物を室温で３０分間燈拝したの
ち、７０〜８０ｑｏで１時間加熱する。7-Ethoxycarbonyl-6,8-dimethyl-4-hydroxymethyl-1-phthalazone 3 Thionyl chloride 10
was added dropwise, and the reaction mixture was heated at room temperature for 30 minutes, then heated at 70-80 qo for 1 hour.
次いで減圧下に過剰の塩化チオニルを留去し、残留物を
アセトンから再結晶すると、融点１８９〜１９１℃の結
晶３夕（理論量の９３．８％）が得られる。マススベク
トル：２９４（Ｍ＋）、２６５，２４９ＮＭＲスペクト
ル：（ＤＭＳＯ−な）６：１２．２５（ｓ、ＩＨ）、７
．６５（ｓ、ＩＨ）、４．８０（ｓ、が）、
４．４５（ｄ、１！ ７Ｈｚ、
ＩＨ）、４．２０（ｄ、１＝７
ＨＺ、ＩＨ）、２．６５（ ｓ、
９Ｈ）、２．３０（ｓ、母日）、
１．２５（ｔ、１ ＝７ＨＺ、
汎）Excess thionyl chloride is then distilled off under reduced pressure, and the residue is recrystallized from acetone to obtain crystalline solids (93.8% of theory) with a melting point of 189-191°C. Mass vector: 294 (M+), 265,249 NMR spectrum: (DMSO-) 6:12.25 (s, IH), 7
．． 65 (s, IH), 4.80 (s, ga), 4.45 (d, 1! 7Hz, IH), 4.20 (d, 1=7 Hz, IH), 2.65 (s, 9H ), 2.30 (s, mother's day), 1.25 (t, 1 = 7HZ, general)
Claims (1)
鎖状もしくは分岐状のアルキル基、Ｘはハロゲン原子を
意味する）で表わされるフタラゾン誘導体。[Claims] 1 General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R_1 and R_2 are lower alkyl groups, R_3 is a linear or branched alkyl group, and X means a halogen atom) A phthalazone derivative represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5334276A JPS6026786B2 (en) | 1976-05-12 | 1976-05-12 | Novel phthalazone derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5334276A JPS6026786B2 (en) | 1976-05-12 | 1976-05-12 | Novel phthalazone derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS52136185A JPS52136185A (en) | 1977-11-14 |
| JPS6026786B2 true JPS6026786B2 (en) | 1985-06-25 |
Family
ID=12940082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5334276A Expired JPS6026786B2 (en) | 1976-05-12 | 1976-05-12 | Novel phthalazone derivatives |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6026786B2 (en) |
-
1976
- 1976-05-12 JP JP5334276A patent/JPS6026786B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS52136185A (en) | 1977-11-14 |
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