JPS5813551B2 - Sinquinapiride (4,3-D) Pyrimidinedione - Google Patents
Sinquinapiride (4,3-D) PyrimidinedioneInfo
- Publication number
- JPS5813551B2 JPS5813551B2 JP50031583A JP3158375A JPS5813551B2 JP S5813551 B2 JPS5813551 B2 JP S5813551B2 JP 50031583 A JP50031583 A JP 50031583A JP 3158375 A JP3158375 A JP 3158375A JP S5813551 B2 JPS5813551 B2 JP S5813551B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- general formula
- substituted
- alkoxy group
- added
- 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
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 title 1
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- RRZBAIDZJRMVES-UHFFFAOYSA-N 1h-pyrido[4,3-d]pyrimidine-2,4-dione Chemical class C1=NC=C2C(=O)NC(=O)NC2=C1 RRZBAIDZJRMVES-UHFFFAOYSA-N 0.000 claims 1
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- -1 sodium alcoholate Chemical class 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 2
- YNBADRVTZLEFNH-UHFFFAOYSA-N methyl nicotinate Chemical compound COC(=O)C1=CC=CN=C1 YNBADRVTZLEFNH-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- NLBIKXOJCISNQP-UHFFFAOYSA-N 4-[3-(trifluoromethyl)anilino]pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=CC=C1NC1=CC=CC(C(F)(F)F)=C1 NLBIKXOJCISNQP-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
- 150000001298 alcohols Chemical class 0.000 description 1
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- MSZJEPVVQWJCIF-UHFFFAOYSA-N butylazanide Chemical compound CCCC[NH-] MSZJEPVVQWJCIF-UHFFFAOYSA-N 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- ZXOAHASJYIUCBG-UHFFFAOYSA-N n-ethylpyridine-3-carboxamide Chemical compound CCNC(=O)C1=CC=CN=C1 ZXOAHASJYIUCBG-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 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（１）
（式中、Ｒは（１）低級アルキル基、（２）ハロゲン原
子、低級シクロアルキル基、低級アルコキシ基又は置換
もしくは無置換のフエニル基で置換された低級アルキル
基、（３）アルケニル基又は（４）アルキニル基を意味
する）で表わされる新規なピリド〔４，３−ｄ〕ピリミ
ジンー２ ．４（ ＩＨ，３Ｈ）一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 (1) (wherein R is (1) a lower alkyl group, (2) a halogen atom, a lower cycloalkyl group, a lower alkoxy group, or a substituted or unsubstituted phenyl group). A novel pyrido[4,3-d]pyrimidine-2. The present invention relates to a method for producing a 4(IH,3H) monodione derivative.
更に詳しくは一般式（ＩＩ）
（式中、Ｘは（１）低級アルコキシ基、（２）低級アル
キルアミノ基、（３）ハロゲン原子、低級シクロアルキ
ル基、低級アルコキシ基又は置換もしくは無置換のフエ
．ニル基で置換された低級アルキルアミノ基、（４）ア
ルケニル基又はアルキニル基で置換されたアミン基を意
味する）で表わされる化合物に一般式（ＩＩＤ
（式中、Ｒは前記と同じ意味を有する）で表わされるイ
ソジアネート類を反応させ、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 general formula (II) (wherein, A lower alkylamino group substituted with a nyl group, (4) an alkenyl group or an amine group substituted with an alkynyl group) is added to a compound represented by the general formula (IID (wherein, R 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 isocyanates represented by the formula (I).
前記一般式（Ｉ） ， （ＩＩ）及び（Ｉ［Ｉ）におけ
るＸ及びＨに就いて更に詳細に説明すると，Ｘの低級ア
ルコキシ基はメトキシ、エトキシ等の低級アルコキシ基
を、Ｒ及びＸの低級アルキル基はメチル、エチル、ｎ一
プロビル、イソプロビル、ｎ−ブチル、イソブチル等の
低級アルキル基を、置換低級アルキル基はハロゲン原子
、低級シクロアルキル基、アルコキシ基、アリール基等
で置換された低級アルキル基を、不飽和アルキル基はア
リル等のアルケニル基及びプロパルギル等のアルキニル
基を表わす。To explain in more detail about X and H in the above general formulas (I), (II) and (I[I), the lower alkoxy group of X is a lower alkoxy group such as methoxy or ethoxy, and the lower alkoxy group of R and The alkyl group is a lower alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, etc., and the substituted lower alkyl group is a lower alkyl group substituted with a halogen atom, lower cycloalkyl group, alkoxy group, aryl group, etc. The unsaturated alkyl group represents an alkenyl group such as allyl and an alkynyl group such as propargyl.
本発明の出発原料である一般式（ＩＩ）で表わされる化
合物は４−（ｍ−１リフルオロメチルアニリノ）ニコチ
ン酸及びその反応性誘導体に、相当するアルコール類及
びアミン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 (II), which is the starting material of the present invention, can be obtained by reacting 4-(m-1-lifluoromethylanilino)nicotinic acid and its reactive derivatives with the corresponding alcohols and amines. Good yield is obtained.
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.
前記の反応式はテトラヒド口フラン、ジグリム、ジオキ
サン、ベンゼン、ジメチルホルムアミド等の不活性有機
溶媒中、ナトリウムアルコラート、，水素化ナトリウム
、水素化カリウム、ナトリウムアミド等の金属化合物の
存在下に、相当するインシアネートを反応させることに
よっておこなわれる。The above reaction formula corresponds to the reaction in the presence of metal compounds such as sodium alcoholate, sodium hydride, potassium hydride, sodium amide, etc. in an inert organic solvent such as tetrahydrofuran, diglyme, dioxane, benzene, dimethylformamide, etc. This is done by reacting incyanate.
反応温度は特に限定されず室温でも進行するが、好まし
くは使用する溶媒の沸点か又は沸点近くで行なうのがよ
い。The reaction temperature is not particularly limited and may proceed at room temperature, but it is preferably carried out at or near the boiling point of the solvent used.
反応生成物は減圧下に溶媒を留去し、残渣をメタノール
、エーテル等の有機溶媒で再結晶するか、又はカラムク
ロマト法により分離精製することによって純品を得るこ
とが出来る。A pure product can be obtained from the reaction product by distilling off the solvent under reduced pressure and recrystallizing the residue from an organic solvent such as methanol or ether, or by separating and purifying it by column chromatography.
本発明で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 in 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。EXAMPLES The present invention will be explained in more detail with reference to Examples below.
実施例゛ １
４−（ｍ− ト’Ｊフルオロメチルアニリノ）ニコチン
酸メチルエステル３．０ｇをテトラヒド口フラン２０ｍ
ｌに溶解し、約′５０％の水素化ナトリウム０．６ｇを
加え室温で１５分間攪拌した。Example 1 3.0 g of 4-(m-t'J fluoromethylanilino)nicotinic acid methyl ester was dissolved in 20 m of tetrahydrofuran.
0.6 g of about 50% sodium hydride was added, and the mixture was stirred at room temperature for 15 minutes.
次にアリルイソシアネート２．４ｇとテトラヒド口フラ
ン１０ＷＬｌの溶液を冷却下に加え室温で１時間、次に
還流下３時間反応させた。Next, a solution of 2.4 g of allyl isocyanate and 10 WL of tetrahydrofuran was added under cooling, and the mixture was reacted for 1 hour at room temperature and then for 3 hours under reflux.
反応終了後、減圧下に溶媒を留去し、残渣に水を加え析
出した結晶をエーテルより再結晶して、無色プリズム晶
の１−（ｍ一トリフルオロメチルフエニル）−３−７’
ｌＪルピリド（４．３−ｄ）ピリミジン−２，４（ Ｉ
Ｈ，３Ｈ）一ジオン２．５ｇを得た。After the reaction, the solvent was distilled off under reduced pressure, water was added to the residue, and the precipitated crystals were recrystallized from ether to give colorless prism crystals of 1-(m-trifluoromethylphenyl)-3-7'.
lJ Lupirido (4.3-d) Pyrimidine-2,4 (I
2.5 g of H,3H) monodione were 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.
？ 点 １８０〜１８１°Ｃ
元素分析値 ＣＩ７Ｆ■ｌＦ３Ｎ３０
理論値Ｃ：５８．７９ Ｈ：３．４９ Ｎ：１２１０実
測値Ｃ：５８．６７ Ｈ：３．４２ Ｎ：１２１３実施
例 ２
４ − （ ＋η一トリフルオロメチルアニリノ）ニコ
チン酸エチルアミド３１ｇをジグリム２０ｍｌに溶解後
、約５０％の水素化ナｌ− ＩＪウム１．Ｏｇを加え室
温で１５分間攪拌した。? Point 180-181°C Elemental analysis value CI7F■lF3N30 Theoretical value C: 58.79 H: 3.49 N: 1210 Actual value C: 58.67 H: 3.42 N: 1213 Example 2 4 - (+η- After dissolving 31 g of trifluoromethylanilino)nicotinic acid ethylamide in 20 ml of diglyme, approximately 50% sodium hydride was added. Og was added and the mixture was stirred at room temperature for 15 minutes.
次にエチルイソシアネート２１ｇとジグリム１０ｍｌの
溶液を冷却下に加え室温で１時間攪拌後、還流下に２時
間反応させた。Next, a solution of 21 g of ethyl isocyanate and 10 ml of diglyme was added under cooling, and after stirring at room temperature for 1 hour, the mixture was reacted under reflux for 2 hours.
反応終了後、減圧下に溶媒を留去し、残渣に水を加えエ
ーテルで抽出、脱水後濃縮すると、無色プリズム晶の１
−（ｍ一トリフルオロメチルフエニル）−３−エチルピ
リド（４．３−ｄ）ピリミジン−２．４（ＩＨ，３Ｈ）
一ジオン２．２ｇを得た。After the reaction, the solvent was distilled off under reduced pressure, water was added to the residue, extracted with ether, dehydrated, and concentrated to obtain colorless prism crystals.
-(m-trifluoromethylphenyl)-3-ethylpyrido(4.3-d)pyrimidine-2.4(IH,3H)
2.2 g of dione 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 １４４〜１４５°Ｃ 元素分析値 Ｃ１６Ｈｌ２Ｆ３Ｎ３０。Melting point 144-145°C Elemental analysis value C16Hl2F3N30.
理論値Ｃ：５７．３１ Ｈ：３．６１ Ｎ：１２．５３
実測値Ｃ：５７．２３ Ｈ：３．５７ Ｎ：１２４８実
施例 ３
４−（ｍ一トリフルオロメチルアニリノ）ニコチン酸一
〇一プチルアミド３．４ｇをテトラヒド口フラン２０ｍ
ｌに溶解し、ナトリウムアミド０．８ｇを加え室温で１
５分間攪拌した。Theoretical value C: 57.31 H: 3.61 N: 12.53
Actual value C: 57.23 H: 3.57 N: 1248 Example 3 3.4 g of 4-(m-trifluoromethylanilino)nicotinic acid 101 butylamide was added to 20 m of tetrahydrofuran.
1, add 0.8 g of sodium amide and stir at room temperature.
Stir for 5 minutes.
次にメチルイソシアネート１．７ｇとテトラヒド口フラ
ン１０ｍｌの溶液を冷却下に加え室温で３０分間攪拌後
、還流下に３時間反応させた。Next, a solution of 1.7 g of methyl isocyanate and 10 ml of tetrahydrofuran was added under cooling, and after stirring at room temperature for 30 minutes, the mixture was reacted under reflux for 3 hours.
反応終了後、減圧下に溶媒を留去し、残渣に水を加え析
出した結晶をメタノールとエーテルの混合溶媒より再結
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−メチルピリド［４，３−ｄ）ピリミ
ジン−２ ．４（ ＩＨ，３Ｈ）一ジオン２．１ｇを得
た。After the reaction, the solvent was distilled off under reduced pressure, water was added to the residue, and the precipitated crystals were recrystallized from a mixed solvent of methanol and ether to obtain colorless prismatic crystals of 1-(m-trifluoromethylphenyl)- 3-Methylpyrido[4,3-d)pyrimidine-2. 2.1 g of 4(IH,3H)-dione was obtained.
？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 the substance were as follows.
融 点 １７８〜１８０°Ｃ
元素分析値 Ｃ１，Ｈ１ｏＦ３Ｎ３０
理論値Ｃ：５６．０８ Ｈ：３．１４ Ｎ：１３．０８
実測値Ｃ：５６．０１ Ｈ：３１８ Ｎ：１３．１１実
施例 ４〜１１
実施例１〜３の方法に準じて次表に示す化合物を好収量
で得た。Melting point 178-180°C Elemental analysis value C1, H1oF3N30 Theoretical value C: 56.08 H: 3.14 N: 13.08
Actual value C: 56.01 H: 318 N: 13.11 Examples 4 to 11 According to the method of Examples 1 to 3, the compounds shown in the following table were obtained in good yields.
Claims (1)
キルアミノ基、（３）ハロゲン原子、低級シクロアルキ
ル基、低級アルコキシ基又は置換もしくは無置換のフエ
ニル基で置換された低級アルキルアミノ基、（４）アル
ケニル基又はアルキニル基で置換されたアミ７基を意味
する）で表わされる化合物に一般式 （式中、Ｒは（１）低級アルキル基、（２）ハロゲン原
子、低級シクロアルキル基、低級アルコキシ基又は置換
もしくは無置換アルコキシ基で置換された低級アルキル
基、（３）アルケニル基又は（４）アルキニル基を意味
する）で表わされる化合物を反応させるこちを特徴とす
る一般式 （式中、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（４．３−ｄ）ピリミジンジオン誘導体の製
造法。[Claims] 1 General formula (wherein X is (1) a lower alkoxy group, (2) a lower alkylamino group, (3) a halogen atom, a lower cycloalkyl group, a lower alkoxy group, or a substituted or unsubstituted A compound represented by the general formula (wherein R is (1) a lower alkyl group, (2) A compound represented by a halogen atom, a lower cycloalkyl group, a lower alkoxy group, a lower alkyl group substituted with a substituted or unsubstituted alkoxy group, (3) an alkenyl group, or (4) an alkynyl group) is reacted. A method for producing a novel pyrido(4.3-d)pyrimidinedione derivative represented by the general formula (wherein R has the same meaning as above) characterized by the following:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50031583A JPS5813551B2 (en) | 1975-03-15 | 1975-03-15 | Sinquinapiride (4,3-D) Pyrimidinedione |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50031583A JPS5813551B2 (en) | 1975-03-15 | 1975-03-15 | Sinquinapiride (4,3-D) Pyrimidinedione |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS51108091A JPS51108091A (en) | 1976-09-25 |
| JPS5813551B2 true JPS5813551B2 (en) | 1983-03-14 |
Family
ID=12335197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50031583A Expired JPS5813551B2 (en) | 1975-03-15 | 1975-03-15 | Sinquinapiride (4,3-D) Pyrimidinedione |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5813551B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4808618A (en) * | 1986-04-16 | 1989-02-28 | Nippon Zoki Pharmaceutical Co., Ltd. | Substituted 1,3-dialkylpyrido[4,3-d]pyrimidine-2,4-diones |
| MX7829A (en) * | 1986-08-21 | 1993-08-01 | Pfizer | QUINAZOLINDIONAS AND PIRIDOPIRIMINDIONAS AND THE PROCEDURE FOR THEIR PREPARATION |
-
1975
- 1975-03-15 JP JP50031583A patent/JPS5813551B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS51108091A (en) | 1976-09-25 |
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