JPS5827795B2 - Synquina 4-oxo-1,4-dihydropyrido (2,3-D) Pyrimidine - Google Patents
Synquina 4-oxo-1,4-dihydropyrido (2,3-D) PyrimidineInfo
- Publication number
- JPS5827795B2 JPS5827795B2 JP50158395A JP15839575A JPS5827795B2 JP S5827795 B2 JPS5827795 B2 JP S5827795B2 JP 50158395 A JP50158395 A JP 50158395A JP 15839575 A JP15839575 A JP 15839575A JP S5827795 B2 JPS5827795 B2 JP S5827795B2
- Authority
- JP
- Japan
- Prior art keywords
- dihydropyrido
- pyrimidine
- oxo
- alkyl group
- 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.)
- 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】
本発明は一般式（Ｉ）
（式中、Ｒ１はアルキル基、ハロゲン原子で置換された
ベンジル基、又はアルケニル基を、Ｒ２は低級アルキル
基又はハロゲン原子で置換された低級アルキル基を意味
する）で表わされる新規な４−オキソ−１・４−ジヒド
ロピリド〔２・３−ｄ〕ピリミジン誘導体の製造法に関
するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to the general formula (I) (wherein R1 is an alkyl group, a benzyl group substituted with a halogen atom, or an alkenyl group, and R2 is a lower alkyl group or a halogen atom substituted The present invention relates to a method for producing a novel 4-oxo-1,4-dihydropyrido[2,3-d]pyrimidine derivative represented by a lower alkyl group.
更に詳しくは一般式（ＩＩ）
（式中、Ｒ２は前記と同じ意味を有する）で表わされる
化合物に一般式（ＩＩＩ）
（式中Ｒ２は前記と同じ意味を有する）で表わされる酸
無水物を反応させ前記一般式（Ｉ）で表わされる化合物
を製造する方法に関するものである。More specifically, an acid anhydride represented by general formula (III) (wherein R2 has the same meaning as above) is added to a compound represented by general formula (II) (wherein R2 has the same meaning as above). The present invention relates to a method for producing a compound represented by the general formula (I) through a reaction.
前記一般式（ｉＬ （ＩＩ）及び（ＩＩＩ）におけるＲ
１及びＲ２について更に詳しく説明すると、Ｒ１のアル
キル基はメチル、エチル、ｎ−プロピル、イソプロピル
、ｎ−ブチル等の低級アルキル基を、弗素、塩素、臭素
、沃素等のハロゲン原子で置換されたベンジル基を、又
アルケニル基はアリル、３−メチルアリル、３・３−ジ
メチルアリル等を表わす。R in the general formula (iL (II) and (III))
1 and R2 in more detail, the alkyl group of R1 is a benzyl group in which a lower alkyl group such as methyl, ethyl, n-propyl, isopropyl, or n-butyl is substituted with a halogen atom such as fluorine, chlorine, bromine, or iodine. The group and alkenyl group represent allyl, 3-methylallyl, 3,3-dimethylallyl, and the like.
Ｒ２の低級アルキル基はメチル、エチル、ｎ〜プロピル
、イソプロピル等を、又ハロゲン原子で置換された低級
アルキル基は弗素、塩素、臭素、沃素等で１〜３個置換
された低級アルキル基を表わす。The lower alkyl group of R2 represents methyl, ethyl, n-propyl, isopropyl, etc., and the lower alkyl group substituted with a halogen atom represents a lower alkyl group substituted with 1 to 3 fluorine, chlorine, bromine, iodine, etc. .
又、出発原料である一般式（ＩＩ）の化合物は２アミノ
ニコチン酸アミド誘導体にオルト酢酸エステルを反応さ
せることによって得られる。Further, the compound of general formula (II), which is a starting material, can be obtained by reacting a diaminonicotinamide derivative with orthoacetic ester.
本発明を反応式で示すと次の通りである。The reaction formula of the present invention is as follows.
本発明の反応は通常エーテル、テトラヒト０７ラン、シ
フリム、アセトン、クロロホルム、ベンゼン、トルエン
、キシレン、ジメチルホルムアミド等の反応に関与しな
い有機溶媒中で行なわれるが、一般式（ＩＩＩ）で表わ
される化合物が液体の場合はこれを溶媒に兼ねさせ反応
させることが出来る。The reaction of the present invention is usually carried out in an organic solvent that does not participate in the reaction, such as ether, tetrahydro7ran, sifrim, acetone, chloroform, benzene, toluene, xylene, dimethylformamide, etc. In the case of a liquid, it can also be used as a solvent for reaction.
反応温度は特に限定されないが通常溶媒の沸点付近で行
なわれることが多い。Although the reaction temperature is not particularly limited, it is usually carried out around the boiling point of the solvent.
又、一般式（ｍ）で表わされる化合物が低沸点の場合封
管中で行うのが有利である。Further, when the compound represented by the general formula (m) has a low boiling point, it is advantageous to carry out the reaction in a sealed tube.
尚、一般式（■）で表わされる化合物の反応性誘導体と
は酸無水物及び酸ハロゲン化物を意味する。Incidentally, the reactive derivative of the compound represented by the general formula (■) means an acid anhydride and an acid halide.
反応生成物は再結晶法又はカラムクロマト法等により容
易に分離することが出来る。The reaction product can be easily separated by recrystallization, column chromatography, or the like.
本発明により得られた化合物は文献未載の新規化合物で
あり、顕著な鎮痛作用、抗炎症作用、中枢神経抑制作用
及び鎮咳作用等の薬理作用を有し、医薬品として産業上
有用な化合物である。The compound obtained by the present invention is a new compound that has not been described in any literature, and has pharmacological effects such as remarkable analgesic effect, anti-inflammatory effect, central nervous system suppressive effect, and antitussive effect, and is an industrially useful compound as a pharmaceutical. .
又、医薬品の中間原料として有用である。It is also useful as an intermediate raw material for pharmaceuticals.
以下に実施例を示し本発明を説明するが、勿論、本発明
はこれらのみに限定されるものではない。The present invention will be explained below with reference to Examples, but of course the present invention is not limited to these examples.
実施例 １
１−エチル−２−メチル−４−オキソ−１・４ジヒドロ
ピリド〔２・３−ｄ〕ピリミジン１．５１を無水酢酸１
６．：ｌ’中、還流下２０時間反応させた。Example 1 1.51 1-ethyl-2-methyl-4-oxo-1,4 dihydropyrido[2,3-d]pyrimidine was dissolved in 1 acetic anhydride.
6. The mixture was reacted for 20 hours under reflux in 1'.
反応終了後、減圧下過剰の無水酢酸を留去し、得られた
結晶をアセトンとメタノールの混合溶媒より再結晶し、
淡黄色針状晶の１−エチル２−アセトニル−４−オキソ
ート４−ジヒドロピリド〔２・３−ｄ〕ピリミジン１．
４Ｐを得た。After the reaction, excess acetic anhydride was distilled off under reduced pressure, and the resulting crystals were recrystallized from a mixed solvent of acetone and methanol.
1-Ethyl 2-acetonyl-4-oxoto-4-dihydropyrido[2.3-d]pyrimidine in pale yellow needles 1.
I got 4P.
この物質の融点及び元素分析値は次の通りであった。The melting point and elemental analysis values of this substance were as follows.
融点 ２２５〜２２６℃
元素分析値 Ｃ１２Ｈ１３Ｎ３０２
理論値 Ｃ：６２．３２ Ｈ：５．６７Ｎ：１８．１
７
実測値 Ｃ：６２．２７ Ｈ：５．６３Ｎ：１８．１
９
実施例 ２
１−エチル−２−メチル−４−オキソ−１・４ジヒドロ
ピリド〔２・３−ｄ〕ピリミジン１．２グと無水トリフ
ルオロ酢酸６７グをベンゼン６ｍｌと混合し、封管中、
７０〜８０℃で２２時間反応させた。Melting point 225-226℃ Elemental analysis value C12H13N302 Theoretical value C: 62.32 H: 5.67 N: 18.1
7 Actual measurement value C: 62.27 H: 5.63 N: 18.1
9 Example 2 1.2 g of 1-ethyl-2-methyl-4-oxo-1.4 dihydropyrido[2.3-d]pyrimidine and 67 g of trifluoroacetic anhydride were mixed with 6 ml of benzene, and in a sealed tube,
It was made to react at 70-80 degreeC for 22 hours.
反応終了後、濃縮し析出した結晶を酢酸エチルエステル
より再結晶して、淡黄色プリスム晶の１−エチル−２−
１−リフルオロアセトニル４−オキソート４〜ジヒト狛
ピリド〔２・３ｄ〕ピリミジン１．５″？を得た。After the reaction was completed, the crystals precipitated by concentration were recrystallized from ethyl acetate to give pale yellow prism crystals of 1-ethyl-2-
1-Lifluoroacetonyl 4-oxoto 4-dihuman komapyrido[2.3d]pyrimidine 1.5''? was obtained.
この物質の融点及び元素分析値は次の通りである。The melting point and elemental analysis values of this substance are as follows.
融点 １８８〜１８９°Ｃ
元素分析値 Ｃｌ２ＨＩｏＦ３Ｎ３０２
理論値 Ｃ：５０．５３ Ｈ：３．５３Ｎ：１４．７
３
実測値 Ｃ：５０．３４ Ｈ：３．６２Ｎ：１４．８
２
以下実施例１〜２の方法に準じて下記の化合物を合成し
た。Melting point 188-189°C Elemental analysis value Cl2HIoF3N302 Theoretical value C: 50.53 H: 3.53 N: 14.7
3 Actual measurement value C: 50.34 H: 3.62 N: 14.8
2 The following compounds were synthesized according to the methods of Examples 1 and 2.
１−メチル−２−クロロアセトニル−４−オキソ−１・
４−ジヒドロ、ピリド（２・３−ｄ」ピリミジン
融 点 １６７〜１６９℃１−エチル−２−ク
ロロアセ）・ニル−４−オキソ−１・４−ジヒドロピリ
ド〔２・３−ｄ〕ピリミジン 融 点 １
６７〜１６８℃１−アリル−２−アセトニル−４−オキ
ソ−１・４−ジヒドロピリド〔２・３−ｄ〕ピリミジン
融点１２６〜１２７°Ｃ
１−アリル−２−クロロアセトニル−４オキソ−１・４
−ジヒドロピリド〔２・３−ｄ〕ピリミジン
融 点 １５５〜１５６℃１− （ｐ −−クロロ
ベンジル）−２−クロロアセトニル−４−オキソ−１・
４−ジヒドロピリド（，２・３−ｄ〕ピリミジン
融点１８１〜１８３℃０1-Methyl-2-chloroacetonyl-4-oxo-1.
4-dihydro,pyrido(2.3-d'pyrimidine)
Melting point: 167-169℃ 1-ethyl-2-chloroacetyl-4-oxo-1,4-dihydropyrido[2,3-d]pyrimidine Melting point 1
67-168°C 1-allyl-2-acetonyl-4-oxo-1,4-dihydropyrido[2,3-d]pyrimidine Melting point 126-127°C 1-allyl-2-chloroacetonyl-4oxo-1. 4
-dihydropyrido[2,3-d]pyrimidine
Melting point 155-156°C 1-(p--chlorobenzyl)-2-chloroacetonyl-4-oxo-1.
4-dihydropyrido(,2,3-d)pyrimidine Melting point 181-183℃0
Claims (1)
ベンジル基、又はアルケニル基を意味する）で表わされ
る化合物に一般式 （式中、Ｒ２は低級アルキル基又はハロゲン原子で置換
された低級アルキル基を意味する）で表わされる化合物
を反応させることを特徴とする一般式（式中、Ｒ１及び
Ｒ２は前記と同じ意味を有する）で表わされる新規な４
−オキソ＝１・４−ジヒドロピリド〔２・３−ｄ〕ピリ
ミジン誘導体の製造法。[Scope of Claims] 1 A compound represented by the general formula (wherein R1 means an alkyl group, a benzyl group substituted with a halogen atom, or an alkenyl group) is combined with a compound represented by the general formula (wherein R2 is a lower alkyl group). or a lower alkyl group substituted with a halogen atom).
-Production method of oxo=1,4-dihydropyrido[2,3-d]pyrimidine derivative.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50158395A JPS5827795B2 (en) | 1975-12-29 | 1975-12-29 | Synquina 4-oxo-1,4-dihydropyrido (2,3-D) Pyrimidine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50158395A JPS5827795B2 (en) | 1975-12-29 | 1975-12-29 | Synquina 4-oxo-1,4-dihydropyrido (2,3-D) Pyrimidine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5283496A JPS5283496A (en) | 1977-07-12 |
| JPS5827795B2 true JPS5827795B2 (en) | 1983-06-11 |
Family
ID=15670788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50158395A Expired JPS5827795B2 (en) | 1975-12-29 | 1975-12-29 | Synquina 4-oxo-1,4-dihydropyrido (2,3-D) Pyrimidine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5827795B2 (en) |
-
1975
- 1975-12-29 JP JP50158395A patent/JPS5827795B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5283496A (en) | 1977-07-12 |
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