JPS5827277B2 - Synquina 4-oxo-1 4-dihydropyrido (2 3-D) Pyrimidine - Google Patents
Synquina 4-oxo-1 4-dihydropyrido (2 3-D) PyrimidineInfo
- Publication number
- JPS5827277B2 JPS5827277B2 JP50069010A JP6901075A JPS5827277B2 JP S5827277 B2 JPS5827277 B2 JP S5827277B2 JP 50069010 A JP50069010 A JP 50069010A JP 6901075 A JP6901075 A JP 6901075A JP S5827277 B2 JPS5827277 B2 JP S5827277B2
- Authority
- JP
- Japan
- Prior art keywords
- dihydropyrido
- pyrimidine
- melting point
- oxo
- oxoto
- 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
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 150000003230 pyrimidines Chemical class 0.000 claims 1
- 238000002844 melting Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- 238000000921 elemental analysis Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- -1 orthoacetic acid ester Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 description 1
- HXKWWDAWOMOFHB-UHFFFAOYSA-N 2-anilinopyridine-3-carboxamide Chemical class NC(=O)C1=CC=CN=C1NC1=CC=CC=C1 HXKWWDAWOMOFHB-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
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はフェニル基、又はハロゲン原子、ニトロ
基、トリフルオロメチル基で置換されたフェニル基を、
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 is based on the general formula (I) (wherein R1 is a phenyl group, or a phenyl group substituted with a halogen atom, a nitro group, or a trifluoromethyl group,
R2 is a lower alkyl group or a lower alkyl group substituted with a halogen atom) .
更に詳しくは一般式（ｎ）
（式中、Ｒ１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（ｍ）
（Ｒ２ＣＯ）、０ （ｍ）
（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, the compound represented by the general formula (n) (wherein R1 has the same meaning as above) has the general formula (m) (R2CO), 0 (m) (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) by reacting an acid anhydride represented by the formula (I).
シ※
前記一般式（Ｉ）、（ＩＩ）及び（ｍ）におけるＲ１
及びＲ２に就いて更に具体的に説明すると、Ｒ１はフェ
ニル基又は塩素、臭素、弗素、沃素等ノハロゲン原子、
ニトロ基、トリフルオロメチル基及び等が任意の位置に
１〜２個置換したフェニル基を表わす。※
R1 in the general formulas (I), (II) and (m)
To explain more specifically about R2, R1 is a phenyl group or a halogen atom such as chlorine, bromine, fluorine, or iodine,
It represents a phenyl group substituted with 1 or 2 nitro groups, trifluoromethyl groups, etc. at arbitrary positions.
又、Ｒ２の低級アルキル基はメチル、エチル、プロピル
等を、ハロゲンで置換された低級アルキル基は塩素、臭
素、弗素、沃素等が１〜３個置換された低級アルキル基
を表わす。Further, the lower alkyl group of R2 represents methyl, ethyl, propyl, etc., and the lower alkyl group substituted with halogen represents a lower alkyl group substituted with 1 to 3 chlorine, bromine, fluorine, iodine, etc.
本発明の出発原料である前記一般式（ｎ）で表わされる
化合物は２−アニリノニコチン酸アミド誘導体にオルト
酢酸エステル類を反応させることによって収量よく得ら
れる。The compound represented by the general formula (n), which is the starting material of the present invention, can be obtained in good yield by reacting a 2-anilinonicotinic acid amide derivative with an orthoacetic acid 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テトラヒドロフラン、ジグリム、ア
−１＝）ン、クロロホルム、ベンゼン、トルエン、キレ
シン、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
ることも出来る。The reaction of the present invention is usually carried out in an organic solvent that does not participate in the reaction, such as tetrahydrofuran, diglyme, ar-1=)one, chloroform, benzene, toluene, chiresine, dimethylformamide, etc., but the compound represented by the general formula (III) When is a liquid, it can also be used as a solvent for the 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.
反応生成物は再結晶法又はクロマトグラフィー法等によ
り容易に分離することが出来る。The reaction product can be easily separated by recrystallization or chromatography.
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
有り、顕著な鎮痛作用、抗炎症作用及び中枢神経抑制作
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, and central nervous system depressing effect, and is an industrially useful compound as a pharmaceutical.
以下に実施例を示し本発明を更に具体的に説明するが、
本発明はもとよりこれらのみに限定されるものではない
。The present invention will be explained in more detail with reference to Examples below.
The present invention is not limited to these examples.
実施例 １
１−（ｍ−クロロフェニル）−２−メチル−４−オキソ
ート４−ジヒドロピリド〔２・３〜ｄ）ピリミジン２．
７ｉを無水酢酸１５ｍＡ中還流下５時間反応させた。Example 1 1-(m-chlorophenyl)-2-methyl-4-oxoto 4-dihydropyrido [2.3-d) Pyrimidine 2.
7i was reacted in acetic anhydride at 15 mA under reflux for 5 hours.
反応終了後、減圧下に溶媒を留去し残渣を酢酸エステル
より再結晶して、無色プリズム晶の１−（ｍ−クロロフ
ェニル） −２−７セトニルー４−オキノート４−ジヒ
ドロピリド〔２・３−ｄ〕ピリミジン２，８りを得た。After the reaction, the solvent was distilled off under reduced pressure and the residue was recrystallized from acetic acid ester to obtain colorless prismatic crystals of 1-(m-chlorophenyl)-2-7cetonyl-4-oquinote-4-dihydropyride [2.3-d ] Pyrimidine 2,8 was obtained.
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２３６〜２３７℃
元素分析値 Ｃ１６■、２ＣＩＮ３０２
理論値 Ｃ：６１．２５ Ｈ：３．８６Ｎ：１３．３
９
実測値 Ｃ：６１．０３ Ｈ：３．７２Ｎ：１３．２
１
実施例 ２
■−（ｍ−ヨードフェニル）−２−メチル−４オキノー
ト４−ジヒドロピリド〔２・３−ｄ）ピリミジン３．６
りと無水トリフルオロ酢酸１５ｍ１を封管中５０〜６０
℃で６時間反応させた。Melting point 236-237℃ Elemental analysis value C16■, 2CIN302 Theoretical value C: 61.25 H: 3.86 N: 13.3
9 Actual measurement value C: 61.03 H: 3.72 N: 13.2
1 Example 2 ■-(m-iodophenyl)-2-methyl-4oquinote 4-dihydropyrido[2.3-d)pyrimidine 3.6
15ml of trifluoroacetic anhydride in a sealed tube.
The reaction was carried out at ℃ for 6 hours.
反応終了後、過剰の無水トリフルオロ酢酸を留去し残渣
をメタノールより再結晶して、無色プリズム晶の１−（
ｍ−ヨードフェニル）−２−トリフルオロアセトニル−
４−オキソート４−ジヒドロピリド〔２・３−ｄ〕ピリ
ミジン３．２２を得た。After the reaction, excess trifluoroacetic anhydride was distilled off and the residue was recrystallized from methanol to obtain colorless prismatic crystals of 1-(
m-iodophenyl)-2-trifluoroacetonyl-
3.22 of 4-oxo-4-dihydropyrido[2.3-d]pyrimidine was obtained.
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２３４〜２３５℃
元素分析値 Ｃ１６Ｈ９Ｆ３■Ｎ３０２
理論値 Ｃ：４１．８５ Ｈ：１．９８Ｎ：９．Ｉ５
実測値 Ｃ：４１．７１ Ｈ：１．８９Ｎ：９．０４
実施例 ３
１−（ｍ−１１Ｊフルオロメチルフエニル）−２メチル
−４−オキソート４−ジヒドロピリド〔２・３−ｄ〕ピ
リミジン０．５ｆ、無水クロル酢酸１．３３Ｐをテトラ
ヒドロフラン３０ｍ１に溶解し２４時間還流した。Melting point 234-235°C Elemental analysis value C16H9F3■N302 Theoretical value C: 41.85 H: 1.98 N: 9. I5 Actual value C: 41.71 H: 1.89 N: 9.04 Example 3 1-(m-11J fluoromethylphenyl)-2methyl-4-oxoto 4-dihydropyrido[2.3-d]pyrimidine 0 .5f and 1.33 P of chloroacetic anhydride were dissolved in 30 ml of tetrahydrofuran and refluxed for 24 hours.
反応終了後、減圧下に溶媒を留去し残渣を酢酸エステル
に溶解し、シリカゲルを充填したカラムに吸着させ酢酸
エステルで展開し、第−溶出部の溶媒を留去し残渣にエ
ーテルを加えると、無色板状晶の１−（ｍ−トリフルオ
ロメチルフェニル）−２−モノロロアセトニルー４オキ
ソート４−ジヒドロピリド〔２・３−ｄ）ピリミジン０
．４１Ｐを得た。After the reaction is complete, the solvent is distilled off under reduced pressure, the residue is dissolved in acetate, adsorbed on a column packed with silica gel, and developed with acetate, the solvent in the first eluate is distilled off, and ether is added to the residue. , colorless plate-like 1-(m-trifluoromethylphenyl)-2-monoloroacetonyl-4oxoto-4-dihydropyrido[2.3-d)pyrimidine 0
．． Obtained 41P.
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１９６〜１９７℃
元素分析値 Ｃ１□Ｈ１１Ｃ１Ｆ３Ｎ３０２理論値 Ｃ
：５３．４９ Ｈ：２．９ＯＮ：１１．０１
実測値 Ｃ：５３．４２ Ｈ：２．８９Ｎ：１１．０
６
実施例１〜３の方法に準じて下記の化合物を合成した。Melting point 196-197℃ Elemental analysis value C1□H11C1F3N302 Theoretical value C
:53.49 H:2.9ON:11.01 Actual value C:53.42 H:2.89N:11.0
6 The following compounds were synthesized according to the methods of Examples 1 to 3.
１−フェニル−２−アセトニル−４−オキソ−１・４−
ジヒドロピリド〔２・３−ｄ〕ｌピリミジン 融点
２４６〜２４８℃
１−（ｐ−クロロフェニル）−２〜アセトニル４〜オキ
ソート４−ジヒドロピリド〔２・３ｄ〕ピリミジン
融 点 ２３７〜２３８℃１−（ｍ−フルオロフェニル
）−２−アセトニル−４−オキソート４−ジヒドロピリ
ド〔２・３−ｄ〕ｌピリミジン融 点 ２５６〜２５７
℃１−（ｐ−フルオロフェニル）−２−アセトニル−４
−オキソート４−ジヒドロピリド〔２・３−ｄ〕ｌピリ
ミジン融 点 ２１５〜２１６℃１−（３・４−ジクロ
ロフェニル）−２−７セトニルー４−オキソート４−ジ
ヒドロピリド〔２・３−ｄ〕ｌピリミジ
ン点２１９〜２２１℃
１−（ｍ−）１）フルオロメチルフェニル）−２アセト
ニル〜４−オキソート４−ジヒドロピリド〔２・３−ｄ
〕ｌピリミジ
ン点２６１〜２６３℃
１−（ｍ−二トロフェニル） −２−７セト＝＃−４−
オキソート４−ジヒドロピリド〔２・３−ｄ、ｌピリミ
ジン
融点２６４〜２６５℃
１−（ｍ−７”ロモフェニル）−２−７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
融点２４２〜２４３℃
１−フェニル−２−モノクロロアセトニルー４オキソ−
１・４−ジヒドロピリド〔２・３−ｄ、１ピリミジン
融 点 ２０５〜２０６℃１−フェニル−２−
４’Ｊフルオロアセトニル４−オキソ、−１・４−ジヒ
ドロピリド〔２・３ｄ〕ピリミジン 融 点 ２１
８〜２２０℃１−（ｍ−ト’）フルオロメチルフェニル
）−２トリフルオロアセトニル−４−オキソート４−ジ
ヒドロピリド〔２・３−ｄ〕ピリミジン融点２３１〜２
３２℃
１−（ｍ−フルオロフェニル）−２−モノクロロアセト
ニルー４−オキソート４−ジヒドロピリド〔２・３−ｄ
〕ｌピリミジ
ン点２５６〜２５７℃
１−（ｐ−フルオロフェニル）−２−モノクロロアセト
ニルー４−オキソート４−ジヒドロピリド〔２・３−ｄ
〕ｌピリミジ
ン点１９２〜１９３℃
１−（ｍ−１’ロロフエニル）−２−モノクロロアセト
ニルー４−オキソート４−ジヒドロピリド〔２・３−ｄ
〕ピリミジン
融点１９５〜１９７℃
１−（ｍ−クロロフェニル）−２−４！Ｊフルオロアセ
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
融点２２９〜２３０℃
１−（ｍ−フロモフェニル）−２−モノクロロアセトー
ル−４−オキソート４−ジヒドロピリド〔２・３−ｄ〕
ピリミジン
融点２０６〜２０７℃1-phenyl-2-acetonyl-4-oxo-1,4-
Dihydropyrido[2,3-d]lpyrimidine Melting point: 246-248°C 1-(p-chlorophenyl)-2-acetonyl 4-oxoto 4-dihydropyrido[2,3d]pyrimidine
Melting point: 237-238°C 1-(m-fluorophenyl)-2-acetonyl-4-oxoto-4-dihydropyrido[2.3-d]lpyrimidine Melting point: 256-257
°C1-(p-fluorophenyl)-2-acetonyl-4
-Oxoto4-dihydropyrido[2,3-d]lpyrimidine Melting point 215-216℃1-(3,4-dichlorophenyl)-2-7cetonyl-4-oxoto4-dihydropyrido[2,3-d]lpyrimidine Point 219-221°C 1-(m-)1)fluoromethylphenyl)-2acetonyl~4-oxoto4-dihydropyrido[2.3-d
[l-pyrimidine point 261-263℃ 1-(m-nitrophenyl)-2-7ceto=#-4-
Oxoto 4-dihydropyrido [2,3-d,l pyrimidine melting point 264-265°C 1-(m-7'' romophenyl)-2-7cetonyl 4-oxoto 4-dihydropyrido [2,3-d) pyrimidine melting point 242-243 °C 1-phenyl-2-monochloroacetonyl-4oxo-
1,4-dihydropyrido [2,3-d,1pyrimidine
Melting point 205-206℃ 1-phenyl-2-
4'J fluoroacetonyl 4-oxo, -1,4-dihydropyrido[2,3d]pyrimidine Melting point 21
8-220℃1-(m-t')fluoromethylphenyl)-2trifluoroacetonyl-4-oxoto4-dihydropyrido[2.3-d]pyrimidine Melting point 231-2
32°C 1-(m-fluorophenyl)-2-monochloroacetonyl-4-oxoto-4-dihydropyrido [2.3-d
[1-pyrimidine point 256-257°C 1-(p-fluorophenyl)-2-monochloroacetonyl-4-oxoto-4-dihydropyrido [2.3-d
[1-pyrimidine point 192-193°C 1-(m-1'rollophenyl)-2-monochloroacetonyl-4-oxoto-4-dihydropyrido [2.3-d
] Pyrimidine melting point 195-197°C 1-(m-chlorophenyl)-2-4! J Fluoroacetonyl-4-oxoto 4-dihydropyrido [2,3-
d] Pyrimidine Melting point 229-230°C 1-(m-furomophenyl)-2-monochloroacetol-4-oxoto 4-dihydropyride [2.3-d]
Pyrimidine melting point 206-207℃
Claims (1)
基、トリフルオロメチル基で置換されたフェニル基を意
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・・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−オキソート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 (in the formula, R1 means a phenyl group, or a phenyl group substituted with a halogen atom, a nitro group, or a trifluoromethyl group) has a compound represented by the general formula (in the formula, R2 means a lower alkyl group or a lower alkyl group substituted with a rogen atom) (wherein R1 and R2 have the same meanings as above) ) is a novel 4-oxo-4-dihydropyride [2
-3-d] Method for producing a pyrimidine derivative.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50069010A JPS5827277B2 (en) | 1975-06-05 | 1975-06-05 | Synquina 4-oxo-1 4-dihydropyrido (2 3-D) Pyrimidine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50069010A JPS5827277B2 (en) | 1975-06-05 | 1975-06-05 | Synquina 4-oxo-1 4-dihydropyrido (2 3-D) Pyrimidine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS527993A JPS527993A (en) | 1977-01-21 |
| JPS5827277B2 true JPS5827277B2 (en) | 1983-06-08 |
Family
ID=13390183
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50069010A Expired JPS5827277B2 (en) | 1975-06-05 | 1975-06-05 | Synquina 4-oxo-1 4-dihydropyrido (2 3-D) Pyrimidine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5827277B2 (en) |
-
1975
- 1975-06-05 JP JP50069010A patent/JPS5827277B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS527993A (en) | 1977-01-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0282502B1 (en) | Imidazole derivatives | |
| GB1588352A (en) | Indoleacetic acid ester derivatives | |
| JPS5827277B2 (en) | Synquina 4-oxo-1 4-dihydropyrido (2 3-D) Pyrimidine | |
| JPS60226878A (en) | 3-amino-1-(4,5,6,7-tetrahydrobenzothiazolyl)-2-pyrazolines and manufacture | |
| US3882119A (en) | Tetracyclic substituted phthalazine compounds | |
| JPS5827795B2 (en) | Synquina 4-oxo-1,4-dihydropyrido (2,3-D) Pyrimidine | |
| JPS5827278B2 (en) | Synquina 4-oxo-1,4-dihydropyrido (2,3-D) Pyrimidine | |
| JPS5833232B2 (en) | Sinquinapyridopyrimidinedione | |
| JPH04368375A (en) | Isoxazole derivative | |
| JPS5813550B2 (en) | Sinquinapiride (4,3-D) Pyrimidinedione | |
| JPS5920675B2 (en) | Method for producing a novel pyrimido[4,5-d]pyrimidine derivative | |
| EP0119091A2 (en) | 2,2-Diethoxypropionic acid derivatives | |
| CN107857729B (en) | A kind of synthetic method of the pyrazole compound of 4- iodate-N- arylation | |
| JPS5920674B2 (en) | Pyrido (2,3-D) Pyrimidine | |
| JPS5813547B2 (en) | Cinquinapiride (2,3-D) Pyrimidinedione | |
| JPH0625258A (en) | Thiazatetracycloundecadiene derivative | |
| JPS5813549B2 (en) | 2-oxo-1,2,3,4-tetrahydropyrido (2,3-D) pyrimidine | |
| JPS5826756B2 (en) | Synquina 4-Oxo-1 2 3 4- Tetrahydropyrido (2 3-D) Pyrimidine | |
| JPH0216311B2 (en) | ||
| JPS5813546B2 (en) | Sinquinapyridopyrimidinedione | |
| JP3655311B2 (en) | Method for producing phthalide compound | |
| JP2893906B2 (en) | Method for producing unsaturated ketone compound | |
| JPH0681744B2 (en) | Method for producing 2,4-dioxyquinoline derivative | |
| JPS5852995B2 (en) | Method for producing furfural derivatives | |
| JPS582953B2 (en) | How to use pyridopyrimidine dione |