JPH038354B2 - - Google Patents
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- JPH038354B2 JPH038354B2 JP16146082A JP16146082A JPH038354B2 JP H038354 B2 JPH038354 B2 JP H038354B2 JP 16146082 A JP16146082 A JP 16146082A JP 16146082 A JP16146082 A JP 16146082A JP H038354 B2 JPH038354 B2 JP H038354B2
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Description
本発明は、血小板凝集抑制作用を有し、式
（）
（式中、R1は水素又は低級アルキル基を、Ａ
環はピリジン環又はテトラハイドロピリジン環を
表わし、Ａ環がピリジン環の場合はR2は水素又
はハロゲンを表わし、Ａ環がテトラハイドロピリ
ジン環の場合はR2は水素を表わす）で表わされ
る四環性のイミダゾピリドキナゾリノン類化合物
及びその酸付加塩に関する。
本発明の化合物は、互変異性体の形でも存在し
うる。従つて本発明は、本明細書で示される式
（）の化合物に限定されるのではなく、その互
変異性体例えば次の式（ａ）及び（ｂ）
（式中、R1，R2及びＡは前記と同じ）で表わ
される互変異性体も本発明に包含される。
本発明の式（）の化合物はR1が低級アルキ
ルの場合はラセミ型又は光学活性型で存在しう
る。これらの全ての型が本発明の一部を構成しう
る。
本発明の式（）の化合物は四環式のイミダゾ
ピリドキナゾリン環系を有するものでその環系を
例示すると、例えば８，９，10，12−テトラヒド
ロイミダゾ〔２，１−ｂ〕ピリド〔２，３−ｆ〕
キナゾリン、８，９，10，12−テトラヒドロイミ
ダゾ〔２，１−ｂ〕ピリド〔３，４−ｆ〕キナゾ
リン、８，９，10，12−テトラヒドロイミダゾ
〔２，１−ｂ〕ピリド〔４，３−ｆ〕キナゾリン、
８，９，10，12−テトラヒドロイミダゾ〔２，１
−ｂ〕ピリド〔３，２−ｆ〕キナゾリン及びこれ
らのピリジン環が部分水素化されたテトラヒドロ
ピリジン環を有する環系が挙げられる。
本発明の化合物は適当な生理学的に無害の酸と
の塩として使用することができる。医薬として使
用可能な塩は、塩酸、臭化水素酸、硫酸、リン
酸、アルキルもしくはアリルスルホン酸、フマー
ル酸、マレイン酸、コハク酸又はクエン酸等当該
技術上通常用いられる酸との塩である。
本発明の化合物は血小板凝集抑制作用をもつこ
とから血管内血栓々塞症の治療と予防、短期局所
貧血の予防及び補綴装置（人工心臓、人工腎臓）
の使用時の血小板血栓の予防等に有用である。
次に本発明の式（）の化合物の血小板凝集抑
制作用を表１及び２に示す。
The present invention has an effect of inhibiting platelet aggregation, and has the formula () (In the formula, R 1 is hydrogen or a lower alkyl group,
The ring represents a pyridine ring or a tetrahydropyridine ring; when ring A is a pyridine ring, R 2 represents hydrogen or a halogen; when ring A is a tetrahydropyridine ring, R 2 represents hydrogen). This invention relates to cyclic imidazopyridoquinazolinone compounds and acid addition salts thereof. The compounds of the invention may also exist in tautomeric forms. Therefore, the present invention is not limited to compounds of formula () as shown herein, but also to tautomers thereof, such as the following formulas (a) and (b): The tautomer represented by (wherein R 1 , R 2 and A are the same as above) is also included in the present invention. The compounds of formula () of the present invention may exist in racemic or optically active form when R 1 is lower alkyl. All these types may form part of the invention. The compound of formula () of the present invention has a tetracyclic imidazopyridoquinazoline ring system, and examples of the ring system include, for example, 8,9,10,12-tetrahydroimidazo[2,1-b]pyrido[ 2,3-f]
Quinazoline, 8,9,10,12-tetrahydroimidazo[2,1-b]pyrido[3,4-f]quinazoline, 8,9,10,12-tetrahydroimidazo[2,1-b]pyrido[4, 3-f] Quinazoline,
8,9,10,12-tetrahydroimidazo[2,1
-b]pyrido[3,2-f]quinazoline and ring systems having a partially hydrogenated tetrahydropyridine ring. The compounds of the invention can be used as salts with suitable physiologically harmless acids. Pharmaceutically usable salts are salts with acids commonly used in the art such as hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, alkyl or allylsulfonic acid, fumaric acid, maleic acid, succinic acid or citric acid. . Since the compound of the present invention has a platelet aggregation inhibitory effect, it can be used for the treatment and prevention of intravascular thromboembolism, for the prevention of short-term local anemia, and for prosthetic devices (artificial heart, artificial kidney).
It is useful for preventing platelet thrombosis when using. Next, Tables 1 and 2 show the platelet aggregation inhibitory effects of the compound of formula () of the present invention.
【表】【table】
【表】
血小板凝集はボーンの比濁法〔Born，
Nature，194巻、927頁（1962）〕に従つて測定し
た。
ａ in vitroはラツトの多血小板血漿を用いてコ
ラーゲン及びADPによる凝集を50％抑制する
ときの濃度（μM）で表わす。
ｂ ex vivoはラツトに10mg／Kgを経口投与し、
コラーゲン及びADPによる凝集抑制率を１時
間後採血して測定した。
ｃ ex vivoの静脈内投与も同様にラツトを用い
て行い、投与後５，10，30及び60分後に採血し
てADP凝集に対する抑制率を測定した。
＊＊Ｐ＜0.01，＊Ｐ＜0.05を表わす。
本発明の化合物は、表１及び２から明らかなよ
うに、強い血小板凝集抑制作用を示し、抗血栓薬
としてすぐれている。さらに本発明の一部の化合
物の特に優れた特徴とするところは、水によく溶
解し水溶液の状態で非経口的に投与できるところ
であり、又静脈内投与も可能な点である。通常、
急性の血管内血栓栓塞症の患者の治療に際し、こ
の種の患者の多くでは、発作時経口的に薬剤を投
与することが極めて困難であり、このようなとき
には即効性が要求されている。即ち、緊急時の非
経口投与、特に静脈内投与可能な薬剤が重要な意
義をもつものである。従来、血小板凝集抑制作用
を報告され、静脈内投与が可能な薬剤は殆ど知ら
れていない。従つて、本発明の化合物が極めて優
れていることがわかる。
次に本発明の式（）の化合物の製造法につい
て述べる。
一般式（）
（式中、R1及びR2は前記と同じ。A′はピリジ
ン環を、R3は低級アルキル基を、Ｘはハロゲン
を示す）の化合物を低級アルコール、例えばメタ
ノール、エタノール等の溶媒中でアンモニアと封
管中100〜150℃に加熱しながら行うことによりＡ
がピリジン環である式（）の化合物が製造でき
る。
また、本発明の式（）の化合物でＡがピリジ
ン環を示す化合物もしくはＡがピリジン環でR2
がハロゲン原子である化合物は公知方法、例えば
パラジウム又は白金等の触媒とともに、低級アル
コール例えばメタノールもしくはエタノール、水
又はこれらの混合溶媒中接触還元することにより
Ａがテトラヒドロピリジン環で、R2が水素原子
である式（）の化合物に導くことができる。
式（）の化合物は次の反応式に従つて製造で
きる。
（式中、R1，R2，R3，A′及びＸは前記と同
じ）
本発明の式（）の化合物及びその互変異性体
とその酸付加塩は、それと適合しうる担体、例え
ば経口又は非経口投与に適した有機又は無機の不
活性担体である水、ゼラチン、アラビアゴム、乳
糖、でんぷん、ステアリン酸マグネシウム、タル
ク、植物性油又はポリアルキレングリコール等を
用いて錠剤、カプセル剤、散剤、液剤又は懸濁剤
等とすることができる。
本発明の化合物は、好ましくは経口又は静脈内
に投与されるが、成人の場合、その投与量は１日
１〜20mgで経口的に、又１日0.1〜10mgの投与量
で静脈内に投与すれば充分である。
以下、実施例で本発明を説明する。
実施例 １
８−クロロ−９，10−ジヒドロピリド〔２，３
−ｆ〕キナゾリン−９−酢酸エチル3.90ｇを10％
アンモニア−エタノール液50mlとともに封管中
120〜130℃で３時間加熱する。冷後析出した結晶
を濾取し、水洗した後乾燥すると８，９，10，12
−テトラヒドロイミダゾ〔２，１−ｂ〕ピリド
〔２，３−ｆ〕キナゾリン−９−オンが2.59ｇ得
られた。これをメタノールに懸濁し、濃塩酸を加
え塩酸塩とした。融点300℃以上。
IR νKBr naxcm-1：3290，3020，1800，1680，1620，
1590
1H−NMR（CF3COOH）δ：
4.75（ｓ，2H），5.62（ｓ，2H），7.88（ｄ，
1H），8.20（dd，1H），8.47（ｄ，1H），9.23
（ｄ，1H），9.26（ｄ，1H）
元素分析C13H10N4O・2HCl・H2Oとして
計算値 C47.43，H4.29，N17.02
分析値 C47.86，H4.43，N16.86
尚、原料物質８−クロロ−９，10−ジヒドロピ
リド〔２，３−ｆ〕キナゾリン−９−酢酸エチル
は以下のようにして製造した。
水酸化カリウム24.7ｇをジメチルホルムアミド
200mlに溶解した液に、氷冷下撹拌しながらシア
ン酢酸エチル49.8ｇを加える。これに７−ニトロ
キノリン25.6ｇをジメチルホルムアミド150mlに
溶解した液を加え、室温で11時間撹拌した。反応
液を氷水に注入し2N−塩酸でPH３〜４にすると
結晶が析出した。析出晶を濾取し、乾燥後シリカ
ゲル処理して精製すると７−エトキサリルアミノ
キノリン−８−カルボニトリル（融点197〜198
℃）が12.1ｇえられた。
このニトリル体11.1ｇをメタノール1000mlに熱
時溶解し、これに水酸化ナトリウム3.30ｇを水40
mlに溶解した液を撹拌しながら加え、室温で10分
間攪拌した。反応液を減圧濃縮し、析出した結晶
を濾取し、水及びアセトンで洗浄して、７−アミ
ノキノリン−８−カルボニトリル（融点245〜246
℃）が6.74ｇえられた。
このアミノニトリル体1.70ｇを尿素3.5ｇと混
和し、210〜230℃で２時間加熱する。冷後反応残
査をよくすりつぶし、水洗し、濾取した。これを
10％塩酸60mlに加え、１夜加熱還流撹拌する。冷
後反応液を水酸化ナトリウム液でPH７に中和する
と沈澱が析出した。析出物を濾取し、水及びメタ
ノールで洗うと７，８，９，10−テトラヒドロピ
リド〔２，３−ｆ〕キナゾリン−８，10−ジオン
（融点300℃以上）が2.12ｇえられた。
このジオン体5.62ｇをオキシ塩化リン240mlと
Ｎ，Ｎ−ジイソプロピルエチルアミン24.0mlの混
液に加え１夜加熱還流撹拌する。反応液を減圧乾
固し、残査を氷水に注入し2N−水酸化ナトリウ
ム水溶液でPH８〜９とする。不溶分を濾取し、こ
れを熱クロロホルムで数回抽出する。クロロホル
ム層を合し、水洗し、クロロホルムを減圧下留去
すると８，10−ジクロロピリド〔２，３−ｆ〕キ
ナゾリン（融点不明確）が4.29ｇえられた。
このジクロル体2.9ｇをクロロホルム350ml及び
エタノール230mlの混液に溶解し、氷冷下に水素
化ホウ素ナトリウム2.63ｇを少しづつ加える。反
応液を室温で１時間撹拌したのち減圧乾固する。
残査を水と処理して不溶分を濾取し水洗し乾燥す
ると８−クロロ−９，10−ジヒドロピリド〔２，
３−ｆ〕キナゾリン（融点80〜81℃）が2.10ｇえ
られた。
このモノクロル体3.10ｇを塩化メチレン300ml
に溶解し、ブロム酢酸エチル2.61ｇ及び沃化テト
ラブチルアンモニウム0.15ｇを加え、撹拌下に
10N−水酸化ナトリウム水溶液15mlを加え、室温
で１時間撹拌する。反応液を水洗し、溶媒を減圧
留去すると８−クロロ−９，10−ジヒドロピリド
〔２，３−ｆ〕キナゾリン−９−酢酸エチル（融
点149〜153℃〕が4.07ｇがえられた。
実施例 ２〜４
実施例１と同様にして実施例２〜４の化合物が
えられた。これらは表にして示す。尚、これらの
化合物の原料物質は、同様にして、実施例１に記
載した原料化合物の製造方法に準じて得ることが
できた。[Table] Platelet aggregation is determined using Born's nephelometric method [Born,
Nature, Vol. 194, p. 927 (1962)]. a In vitro is expressed as the concentration (μM) required to inhibit collagen and ADP aggregation by 50% using rat platelet-rich plasma. b Ex vivo, 10 mg/Kg was orally administered to rats.
Blood was collected 1 hour later and the rate of inhibition of aggregation by collagen and ADP was measured. c Ex vivo intravenous administration was similarly carried out using rats, and blood was collected at 5, 10, 30, and 60 minutes after administration to measure the inhibition rate against ADP aggregation. **Represents P<0.01, *P<0.05. As is clear from Tables 1 and 2, the compounds of the present invention exhibit strong platelet aggregation inhibiting effects and are excellent as antithrombotic agents. Furthermore, a particularly excellent feature of some of the compounds of the present invention is that they dissolve well in water and can be administered parenterally in the form of an aqueous solution, and can also be administered intravenously. usually,
When treating patients with acute intravascular thromboembolism, it is extremely difficult to orally administer drugs to many of these patients at the time of attack, and prompt action is required in such cases. That is, drugs that can be administered parenterally in an emergency, especially intravenously, are of great significance. Until now, there are almost no known drugs that have been reported to have an inhibitory effect on platelet aggregation and can be administered intravenously. Therefore, it can be seen that the compounds of the present invention are extremely superior. Next, a method for producing the compound of formula () of the present invention will be described. General formula () (In the formula, R 1 and R 2 are the same as above. A' is a pyridine ring, R 3 is a lower alkyl group, and X is a halogen) in a solvent such as a lower alcohol, such as methanol or ethanol. A by heating to 100-150℃ in a sealed tube with ammonia.
A compound of formula () in which is a pyridine ring can be produced. Further, in the compound of formula () of the present invention, A is a pyridine ring, or A is a pyridine ring and R 2
Compounds in which is a halogen atom can be prepared by catalytic reduction in a lower alcohol such as methanol or ethanol, water, or a mixed solvent thereof with a catalyst such as palladium or platinum using a known method, such that A is a tetrahydropyridine ring and R 2 is a hydrogen atom. This can lead to a compound of formula (). The compound of formula () can be produced according to the following reaction formula. (In the formula, R 1 , R 2 , R 3 , A' and Tablets, capsules, etc. are prepared using organic or inorganic inert carriers such as water, gelatin, gum arabic, lactose, starch, magnesium stearate, talc, vegetable oil, or polyalkylene glycol, which are suitable for oral or parenteral administration. It can be in the form of a powder, solution, suspension, or the like. The compounds of the invention are preferably administered orally or intravenously; in adults, the dosage is 1 to 20 mg per day orally and 0.1 to 10 mg per day intravenously. It is enough. The present invention will be explained below with reference to Examples. Example 1 8-chloro-9,10-dihydropyride [2,3
-f] Quinazoline-9-ethyl acetate 3.90g 10%
In a sealed tube with 50ml of ammonia-ethanol solution
Heat at 120-130℃ for 3 hours. After cooling, the precipitated crystals are collected by filtration, washed with water, and dried to give 8,9,10,12
2.59 g of -tetrahydroimidazo[2,1-b]pyrido[2,3-f]quinazolin-9-one was obtained. This was suspended in methanol and concentrated hydrochloric acid was added to make the hydrochloride. Melting point over 300℃. IR ν KBr nax cm -1 : 3290, 3020, 1800, 1680, 1620,
1590 1 H-NMR (CF 3 COOH) δ: 4.75 (s, 2H), 5.62 (s, 2H), 7.88 (d,
1H), 8.20 (dd, 1H), 8.47 (d, 1H), 9.23
(d, 1H), 9.26 (d, 1H) Elemental analysis C 13 H 10 N 4 O・2HCl・H 2 O Calculated value C47.43, H4.29, N17.02 Analysis value C47.86, H4.43 , N16.86 The raw material 8-chloro-9,10-dihydropyrido[2,3-f]quinazoline-9-ethyl acetate was produced as follows. 24.7g of potassium hydroxide in dimethylformamide
Add 49.8 g of ethyl cyanacetate to the 200 ml solution while stirring under ice cooling. A solution prepared by dissolving 25.6 g of 7-nitroquinoline in 150 ml of dimethylformamide was added to this, and the mixture was stirred at room temperature for 11 hours. The reaction solution was poured into ice water and the pH was adjusted to 3 to 4 with 2N hydrochloric acid to precipitate crystals. The precipitated crystals are collected by filtration, dried and purified by silica gel treatment to yield 7-ethoxarylaminoquinoline-8-carbonitrile (melting point 197-198
℃) was obtained. Dissolve 11.1 g of this nitrile in 1000 ml of methanol while hot, add 3.30 g of sodium hydroxide to 40 ml of water.
ml of the solution was added with stirring, and the mixture was stirred at room temperature for 10 minutes. The reaction solution was concentrated under reduced pressure, and the precipitated crystals were collected by filtration and washed with water and acetone to give 7-aminoquinoline-8-carbonitrile (melting point 245-246
℃) was obtained. 1.70 g of this aminonitrile compound is mixed with 3.5 g of urea and heated at 210 to 230°C for 2 hours. After cooling, the reaction residue was thoroughly ground, washed with water, and collected by filtration. this
Add to 60 ml of 10% hydrochloric acid, and stir and heat under reflux overnight. After cooling, the reaction solution was neutralized to pH 7 with sodium hydroxide solution, and a precipitate was deposited. The precipitate was collected by filtration and washed with water and methanol to obtain 2.12 g of 7,8,9,10-tetrahydropyrido[2,3-f]quinazoline-8,10-dione (melting point 300°C or higher). . 5.62 g of this dione was added to a mixed solution of 240 ml of phosphorus oxychloride and 24.0 ml of N,N-diisopropylethylamine, and the mixture was heated under reflux and stirred overnight. The reaction solution was dried under reduced pressure, the residue was poured into ice water, and the pH was adjusted to 8-9 with 2N aqueous sodium hydroxide solution. Insoluble matter is filtered and extracted several times with hot chloroform. The chloroform layers were combined, washed with water, and the chloroform was distilled off under reduced pressure to obtain 4.29 g of 8,10-dichloropyrido[2,3-f]quinazoline (melting point unclear). Dissolve 2.9 g of this dichloride in a mixture of 350 ml of chloroform and 230 ml of ethanol, and add 2.63 g of sodium borohydride little by little while cooling on ice. The reaction solution was stirred at room temperature for 1 hour and then dried under reduced pressure.
The residue is treated with water, the insoluble matter is filtered, washed with water and dried to give 8-chloro-9,10-dihydropyride [2,
3-f] 2.10 g of quinazoline (melting point 80-81°C) was obtained. Add 3.10g of this monochloride to 300ml of methylene chloride.
Add 2.61 g of ethyl bromoacetate and 0.15 g of tetrabutylammonium iodide, and stir.
Add 15 ml of 10N aqueous sodium hydroxide solution and stir at room temperature for 1 hour. The reaction solution was washed with water and the solvent was distilled off under reduced pressure to obtain 4.07 g of ethyl 8-chloro-9,10-dihydropyrido[2,3-f]quinazoline-9-acetate (melting point 149-153°C). Examples 2 to 4 The compounds of Examples 2 to 4 were obtained in the same manner as in Example 1.These are shown in a table.The raw materials for these compounds were the same as those described in Example 1. It could be obtained according to the method for producing the raw material compound.
【表】【table】
【表】
実施例 ５
８，９，10，12−テトラヒドロイミダゾ〔２，
１−ｂ〕ピリド〔２，３−ｆ〕キナゾリン−９−
オン1.19ｇをメタノール120ml及び10％塩酸24ml
の混液に懸濁し、これに酸化白金0.12ｇを加えて
常温及び常圧下に接触還元した。水素の吸収が止
んでから（４時間）接触を濾去して反応液を減圧
乾固する。残査をエタノールで洗うと１，２，
３，４，８，９，10，12−オクタヒドロイミダゾ
〔２，１−ｂ〕ピリド〔２，３−ｆ〕キナゾリン
−９−オン塩酸塩が1.52ｇえられた。融点280℃
以上。
IR νKBr naxcm-1：2930，2850，1780，1680，1630，
1590
1H−NMR（D2O）δ：
2.0〜2.3（ｍ，4H），2.95（ｍ，2H），3.60（ｍ，
2H），4.45（ｓ，2H），4.86（ｓ，2H），7.11
（ｄ，1H），7.38（ｄ，1H）
元素分析C13H14N4O・2HCl・2H2Oとして
計算値 C44.45，H5.74，N15.95
分析値 C44.24，H5.34，N15.88
実施例 ６〜７
実施例５と同様にして、実施例６〜７の化合物
を製造した。尚、これらの化合物の原料となつた
化合物は実施例６が実施例２の化合物、実施例７
の化合物は実施例３又は４の化合物である。結果
は表にして示す。[Table] Example 5 8,9,10,12-tetrahydroimidazo[2,
1-b]pyrido[2,3-f]quinazoline-9-
1.19 g of 120 ml of methanol and 24 ml of 10% hydrochloric acid
0.12 g of platinum oxide was added thereto, and catalytic reduction was carried out at room temperature and pressure. After hydrogen absorption has ceased (4 hours), the contact is removed by filtration and the reaction solution is dried under reduced pressure. When the residue is washed with ethanol, 1, 2,
1.52 g of 3,4,8,9,10,12-octahydroimidazo[2,1-b]pyrido[2,3-f]quinazolin-9-one hydrochloride was obtained. Melting point 280℃
that's all. IR ν KBr nax cm -1 :2930, 2850, 1780, 1680, 1630,
1590 1 H-NMR (D 2 O) δ: 2.0-2.3 (m, 4H), 2.95 (m, 2H), 3.60 (m,
2H), 4.45 (s, 2H), 4.86 (s, 2H), 7.11
(d, 1H), 7.38 (d, 1H) Elemental analysis C 13 H 14 N 4 O・2HCl・2H 2 O Calculated value C44.45, H5.74, N15.95 Analysis value C44.24, H5.34 , N15.88 Examples 6-7 Compounds of Examples 6-7 were produced in the same manner as in Example 5. In addition, the compounds used as raw materials for these compounds are the compound of Example 2 in Example 6, and the compound of Example 7 in Example 6.
The compound is the compound of Example 3 or 4. The results are shown in a table.
【表】【table】
Claims (1)
環はピリジン環又はテトラハイドロピリジン環を
表わし、Ａ環がピリジン環の場合はR2は水素又
はハロゲンを表わし、Ａ環がテトラハイドロピリ
ジン環の場合はR2は水素を表わす）の四環性イ
ミダゾピリドキナゾリン類化合物及びその酸付加
塩。 ２ １，２，３，４，８，９，10，12−オクタヒ
ドロイミダゾ［２，１−ｂ］ピリド［２，３−
ｆ］キナゾリン−９−オン及びその酸付加塩であ
る特許請求の範囲第１項記載の化合物。 ３ １，２，３，４，８，９，10，12−オクタヒ
ドロイミダゾ［２，１−ｂ］ピリド［３，２−
ｆ］キナゾリン−９−オン及びその酸付加塩であ
る特許請求の範囲第１項記載の化合物。[Claims] 1. General formula (In the formula, R 1 is hydrogen or a lower alkyl group,
The ring represents a pyridine ring or a tetrahydropyridine ring, when ring A is a pyridine ring, R 2 represents hydrogen or halogen, and when ring A is a tetrahydropyridine ring, R 2 represents hydrogen). Imidazopyridoquinazoline compounds and their acid addition salts. 2 1,2,3,4,8,9,10,12-octahydroimidazo[2,1-b]pyrido[2,3-
f] The compound according to claim 1, which is quinazolin-9-one and its acid addition salt. 3 1,2,3,4,8,9,10,12-octahydroimidazo[2,1-b]pyrido[3,2-
f] The compound according to claim 1, which is quinazolin-9-one and its acid addition salt.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16146082A JPS5951285A (en) | 1982-09-16 | 1982-09-16 | Imidazopyridoquinazolinone compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16146082A JPS5951285A (en) | 1982-09-16 | 1982-09-16 | Imidazopyridoquinazolinone compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5951285A JPS5951285A (en) | 1984-03-24 |
| JPH038354B2 true JPH038354B2 (en) | 1991-02-05 |
Family
ID=15735525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16146082A Granted JPS5951285A (en) | 1982-09-16 | 1982-09-16 | Imidazopyridoquinazolinone compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5951285A (en) |
-
1982
- 1982-09-16 JP JP16146082A patent/JPS5951285A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5951285A (en) | 1984-03-24 |
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