JPS582950B2 - Sinquinapyridopyrimidinedione - Google Patents
SinquinapyridopyrimidinedioneInfo
- Publication number
- JPS582950B2 JPS582950B2 JP743784A JP378474A JPS582950B2 JP S582950 B2 JPS582950 B2 JP S582950B2 JP 743784 A JP743784 A JP 743784A JP 378474 A JP378474 A JP 378474A JP S582950 B2 JPS582950 B2 JP S582950B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- halogen atom
- general formula
- phenyl
- compound represented
- 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
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 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
- BJLUORNGPCXNHM-UHFFFAOYSA-N 1h-pyrido[3,2-d]pyrimidine-2,4-dione Chemical class C1=CN=C2C(=O)NC(=O)NC2=C1 BJLUORNGPCXNHM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- -1 alkyl halide carbonates Chemical class 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 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
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JQPYINKVAWEQDQ-UHFFFAOYSA-N 1h-pyrido[2,3-d]pyrimidine-2,4-dione Chemical compound C1=CC=C2C(=O)NC(=O)NC2=N1 JQPYINKVAWEQDQ-UHFFFAOYSA-N 0.000 description 1
- VYNIOQSDRVUSNY-UHFFFAOYSA-N 2-(2-hydroxyethyl)pyridine-3-carboxamide Chemical compound NC(=O)C1=CC=CN=C1CCO VYNIOQSDRVUSNY-UHFFFAOYSA-N 0.000 description 1
- XSBAKONFFCSERK-UHFFFAOYSA-N 2-aminopyridine-3-carbonyl chloride Chemical compound NC1=NC=CC=C1C(Cl)=O XSBAKONFFCSERK-UHFFFAOYSA-N 0.000 description 1
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004440 column chromatography 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 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、Ａは炭素数２〜３の直鎖又は有枝状のアルキレ
ン基を、Ｒはフエニル基、ハロゲン原子、低級アルキル
基、低級アルコキシ基、ニトロ基又はトリフルオロメチ
ル基で置換されたフエニル基、シクロヘキシル基又はベ
ンジル基を意味する）で表わされるピリドピリミジンジ
オ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 A is a linear or branched alkylene group having 2 to 3 carbon atoms, R is a phenyl group, a halogen atom, a lower alkyl group, The present invention relates to a method for producing a pyridopyrimidinedione derivative represented by a phenyl group, a cyclohexyl group, or a benzyl group substituted with a lower alkoxy group, a nitro group, or a trifluoromethyl group.
更に詳しくは一般式（ＩＩ）
（式中、Ａ及びＲ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）
ＸＣＯＹ （ＩＩＩ）
（式中、Ｘはハロゲン原子を、Ｙはハロゲ塔原子、アル
コキシ基及びアリールオキシ基を意味する）で表わされ
る化合物を反応させ、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 (II) (wherein A and R have the same meanings as above) is combined with the general formula (III) XCOY (III) (wherein, X represents a halogen atom, and Y represents a halogen The present invention relates to a method for producing a compound represented by the general formula (I) by reacting a compound represented by a column atom, an alkoxy group, or an aryloxy group.
前記一般式（Ｉ）及び（ＩＩ）におけるＲを更に詳細に
説明すると、Ｒフエニル基、又は塩素、臭素、弗素、沃
素等のハロゲン原子、メチル、エチル等の低級キシ基、
ニトロ基及びトリフルオロメチル基等を任意の位置に１
〜２個置換したフエニル基を、シクロヘキシル基又はベ
ンジル基を表わす。To explain R in the general formulas (I) and (II) in more detail, R phenyl group, or a halogen atom such as chlorine, bromine, fluorine, or iodine, or a lower oxy group such as methyl or ethyl;
Nitro group, trifluoromethyl group, etc. at any position 1
A phenyl group substituted with ~2 represents a cyclohexyl group or a benzyl group.
又、一般式（ＩＩＩ）で表わされる化合物は具体的には
クロロ炭酸エチル、クロロ炭酸フエニル等のハロゲノ炭
酸アルキル、ハロゲノ炭酸アリール及びホスゲン等を表
わす。Further, the compound represented by the general formula (III) specifically represents alkyl halide carbonates such as ethyl chlorocarbonate and phenyl chlorocarbonate, aryl halide carbonates, and phosgene.
本発明の出発原料である一般式（ＩＩ）の化合物は２−
アミノニコチン酸クロライドに相当するアルコールアミ
ン類を反応させることによって好収率で得られる。The compound of general formula (II) which is the starting material of the present invention is 2-
It can be obtained in good yield by reacting an alcohol amine corresponding to aminonicotinic acid chloride.
本発明の方法を反応式で示すと次の通りである。The reaction formula of the method of the present invention is as follows.
本反応は一般にテトラヒドロフラン、ジグリム、ベンゼ
ン、トルエン、クロロホルム等の有機溶媒中、水素化ナ
トリウム、ナトリウムアミド、カリウムアミド、ナトリ
ウムアルコラート等の金属化ご合物を使用して反応させ
ると好収率で目的化合物を得ることができる。This reaction is generally carried out in good yields when carried out using a metal compound such as sodium hydride, sodium amide, potassium amide, or sodium alcoholate in an organic solvent such as tetrahydrofuran, diglyme, benzene, toluene, or chloroform. compound can be obtained.
反応は一般に還流下２〜５時間加熱することによって行
なわれる。The reaction is generally carried out by heating under reflux for 2 to 5 hours.
生成した反応混合物は減圧下で溶媒を留去し残べ渣を有
機溶媒で再結晶するか、カラムクロマトで分離精製して
純品を得ることができる。A pure product can be obtained by distilling off the solvent from the generated reaction mixture under reduced pressure and recrystallizing the remaining residue from an organic solvent, or by separating and purifying it by column chromatography.
本発明で得られた目的化合物は顕著な鎮痛作用、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 target compound obtained in the present invention has pharmacological effects such as remarkable analgesic action, anti-inflammatory action, and central nervous system depressing action, and is an industrially useful compound as a pharmaceutical.
以下に本発明の実施例を示す。Examples of the present invention are shown below.
実施例 １
２−（ｍ−クロロアニリノ）−Ｎ−（２−ハイドロキシ
エチル）ニコチン酸アミド２．９ｇとテトラヒド口フラ
ン３０ｍｌの溶液に約５０％の水素化ナトリウム１．０
ｇを加え室温で３０分間攪拌後、水冷下にクロロ炭酸エ
チル３．２ｇとテトラヒドロフラン１０ｍｌの溶液を徐
々に滴下し室温で１時間次に還流下２時間反応させた。Example 1 About 50% sodium hydride 1.0 was added to a solution of 2.9 g of 2-(m-chloroanilino)-N-(2-hydroxyethyl)nicotinamide and 30 ml of tetrahydrofuran.
After stirring at room temperature for 30 minutes, a solution of 3.2 g of ethyl chlorocarbonate and 10 ml of tetrahydrofuran was gradually added dropwise under water cooling, and the mixture was reacted at room temperature for 1 hour and then under reflux for 2 hours.
反応終了後、減圧下に溶媒を留去し残渣をエーテルで抽
出し、これをアルミナを充填したカラムに吸着させ酢酸
エチルで展開し、流出液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−クロロフエニ
ル）−３−（２−ハイドロキシエチル）ピリド（２．３
−ｄ）ピリミジンー２，４（ＩＨ，３Ｈ）一ジオン２．
２ｇを得た。After the reaction, the solvent was distilled off under reduced pressure, the residue was extracted with ether, adsorbed on a column packed with alumina, developed with ethyl acetate, the effluent was distilled off, and the residue was recrystallized from methanol. Colorless prismatic crystals of 1-(m-chlorophenyl)-3-(2-hydroxyethyl)pyrido (2.3
-d) Pyrimidine-2,4(IH,3H)-dione2.
2g 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 １７６〜１７７℃
元素分析値 Ｃ１５Ｈ１２ＣｌＮ３０３
理論値Ｃ：５６．７０ Ｈ：３．８１ Ｎ：１３．２３
実測値Ｃ：５６．８１ Ｈ：３．９５ Ｎ：１３．１０
実施例 ２
２−（ｍ−トリフルオロメチルアニリノ） 一Ｎ−（２
−ハイドロキシエチル）ニコチン酸アミド３．３ｇとテ
トラヒドロフラン３０ｍｌの溶液に約５０％の水素化ナ
トリウム１．０ｇを加え室温で３０分間攪拌後、水冷下
クロロ炭酸フエニル４，７ｇとテトラヒド口フラン１０
ｍｌの溶液を徐々に滴下し室温で１時間、次に還流下４
時間加熱した。Melting point 176-177℃ Elemental analysis value C15H12ClN303 Theoretical value C: 56.70 H: 3.81 N: 13.23
Actual value C: 56.81 H: 3.95 N: 13.10
Example 2 2-(m-trifluoromethylanilino) 1N-(2
- To a solution of 3.3 g of (hydroxyethyl) nicotinic acid amide and 30 ml of tetrahydrofuran was added 1.0 g of about 50% sodium hydride, and after stirring at room temperature for 30 minutes, 4.7 g of phenyl chlorocarbonate and 10 g of tetrahydrofuran were added under water cooling.
ml of the solution was gradually added dropwise at room temperature for 1 hour, then under reflux for 4 hours.
heated for an hour.
反応終了後、減圧下に溶媒を留去し残渣をエーテルで抽
出しアルミナを充填したカラムに吸着させ酢酸エチルで
展開し、流出液を留去し残渣をエーテルと石油エーテル
で再結晶して、無色プリズム晶の１−（ｍ−トリフルオ
ロメチルフエニル）−３−（２−ハイドロキシエチル）
ピリド〔２，３−ｄ）ピリミジン−２，４（１Ｈ，３Ｈ
）−ジオン１．９ｇを得た。After the reaction, the solvent was distilled off under reduced pressure, the residue was extracted with ether, adsorbed on a column packed with alumina, developed with ethyl acetate, the effluent was distilled off, and the residue was recrystallized with ether and petroleum ether. Colorless prismatic crystals of 1-(m-trifluoromethylphenyl)-3-(2-hydroxyethyl)
Pyrido[2,3-d)pyrimidine-2,4(1H,3H
)-dione (1.9 g) 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 １４２〜１４３℃
元素分析値 Ｃ１６Ｈ１２Ｆ３Ｎ３Ｏ３
理論値Ｃ：５４．７０ Ｈ：３．４４ Ｎ：１１．９６
実測値Ｃ：５４．６８ Ｈ：３．４１ Ｎ：１１．８５
実施例 ３〜３４
実施例１〜２の方法に準じて次表に示す化合物を好収率
で得た。Melting point 142-143℃ Elemental analysis value C16H12F3N3O3 Theoretical value C: 54.70 H: 3.44 N: 11.96
Actual value C: 54.68 H: 3.41 N: 11.85
Examples 3-34 According to the method of Examples 1-2, the compounds shown in the following table were obtained in good yields.
Claims (1)
ン基を、Ｒは（１）フエニル基、（２）ハロゲン原子、
低級アルキル基、低級アルコキシ基、ニトロ基又はトリ
フルオロメチル基で置換されたフエニル基、（３）シク
ロヘキシル基、（４）ベンジル基茶意味する）で表わさ
れる化合物に一般式 ＸＣＯＹ （式中、Ｘはハロゲン原子を、Ｙはハロゲン原子、アル
コキシ基又はアリールオキシ基を意味する）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、Ａ及びＲは前記と同じ意味を有する）で表わさ
れる新規なピリドピリミジンジオン誘導体の製造法。[Scope of Claims] 1 General formula (wherein A is a linear or branched alkylene group having 2 to 3 carbon atoms, R is (1) a phenyl group, (2) a halogen atom,
A compound represented by a lower alkyl group, a lower alkoxy group, a phenyl group substituted with a nitro group or a trifluoromethyl group, (3) a cyclohexyl group, and (4) a benzyl group has the general formula is a halogen atom, and Y is a halogen atom, an alkoxy group or an aryloxy group) (wherein A and R have the same meanings as above). A method for producing the novel pyridopyrimidinedione derivatives.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP743784A JPS582950B2 (en) | 1973-12-22 | 1973-12-22 | Sinquinapyridopyrimidinedione |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP743784A JPS582950B2 (en) | 1973-12-22 | 1973-12-22 | Sinquinapyridopyrimidinedione |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5093996A JPS5093996A (en) | 1975-07-26 |
| JPS582950B2 true JPS582950B2 (en) | 1983-01-19 |
Family
ID=11566800
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP743784A Expired JPS582950B2 (en) | 1973-12-22 | 1973-12-22 | Sinquinapyridopyrimidinedione |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS582950B2 (en) |
-
1973
- 1973-12-22 JP JP743784A patent/JPS582950B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5093996A (en) | 1975-07-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US11542245B2 (en) | Preparative process | |
| US4251659A (en) | Polyfluorohydroxyisopropyl-heterocyclic compounds | |
| JPS582950B2 (en) | Sinquinapyridopyrimidinedione | |
| JPS5920676B2 (en) | Method for producing a novel pyrimido[4,5-d]pyrimidine derivative | |
| JP3564982B2 (en) | 4-Fluoro-3-oxocarboxylic acid ester and method for producing the same | |
| CA1055036A (en) | 3-amino-4-carbamyl-pyrrol derivatives and methods for their preparation | |
| JPS582947B2 (en) | Sinquinapyridopyrimidinedione | |
| JPS58429B2 (en) | Synquina 2-oxo-1,2,3,4-tetrahydropyride (2,3-D) Pyrimidine | |
| JPS5813551B2 (en) | Sinquinapiride (4,3-D) Pyrimidinedione | |
| JPS5813550B2 (en) | Sinquinapiride (4,3-D) Pyrimidinedione | |
| Kirschke et al. | Surprising reactions or special azoolefins-self-arylation, indole ring closure, mild chlorine substitution, and “tert. amino effect” | |
| JPS5920677B2 (en) | Method for producing a novel pyrimido[4,5-d]pyrimidinedione derivative | |
| JP2659587B2 (en) | 4-aziridinyl pyrimidine derivatives and their production | |
| JPS5813547B2 (en) | Cinquinapiride (2,3-D) Pyrimidinedione | |
| JPS5920675B2 (en) | Method for producing a novel pyrimido[4,5-d]pyrimidine derivative | |
| JPS5920674B2 (en) | Pyrido (2,3-D) Pyrimidine | |
| US4533732A (en) | 3-Propionylsalicylic acid derivatives and process for the preparation of the same | |
| JPS58432B2 (en) | Cinquinapiride -1,4- Diazepine | |
| US3683086A (en) | Derivatives of acetic acid for the alleviation of hyperlipemia | |
| JPS5813545B2 (en) | Sinquinapiride % 2 3 - D @ pyrimidinedione | |
| JPS5833232B2 (en) | Sinquinapyridopyrimidinedione | |
| JPH035466A (en) | Production of phenoxyethylaminopyrimidine derivative | |
| JPS5813548B2 (en) | Sinquinapyridopyrimidinedione | |
| JPS5830317B2 (en) | Cinquinapiride (2,3-D) Pyrimidinedione | |
| JPH0641066A (en) | Production of pyrrole derivative |